#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/59/2225978.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_2225978
loop_
_publ_author_name
'Fun, Hoong-Kun'
'Hemamalini, Madhukar'
'Asiri, Abdullah M.'
'Khan, Salman A.'
_publ_section_title
;
 1-[(E)-(3,4-Dimethylisoxazol-5-yl)iminomethyl]-2-naphthol
;
_journal_coeditor_code           SJ2761
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1037
_journal_page_last               o1038
_journal_paper_doi               10.1107/S160053681001216X
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C16 H14 N2 O2'
_chemical_formula_moiety         'C16 H14 N2 O2'
_chemical_formula_sum            'C16 H14 N2 O2'
_chemical_formula_weight         266.29
_chemical_name_systematic
;
1-[(E)-(3,4-Dimethylisoxazol-5-yl)iminomethyl]-2-naphthol
;
_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                 117.377(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.5250(6)
_cell_length_b                   15.4643(12)
_cell_length_c                   12.3982(7)
_cell_measurement_reflns_used    3616
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      34.17
_cell_measurement_theta_min      2.63
_cell_volume                     1281.17(17)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type
;
Bruker APEX DUO CCD area-detector diffractometer
;
_diffrn_measurement_method       'φ and 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  0.0414
_diffrn_reflns_av_sigmaI/netI    0.0356
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16577
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.27
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.9956
_exptl_absorpt_correction_T_min  0.9303
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.79
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.451
_refine_diff_density_min         -0.226
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3704
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0457
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0698P)²+0.3682P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1201
_refine_ls_wR_factor_ref         0.1344
_reflns_number_gt                2843
_reflns_number_total             3704
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj2761.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 
;
_cod_original_cell_volume        1281.17(16)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2225978
_cod_database_fobs_code          2225978
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 0.20289(17) 1.11942(6) 0.64493(8) 0.0209(2) Uani d . 1 . .
O O2 0.24094(15) 0.97368(6) 0.30327(8) 0.0173(2) Uani d . 1 . .
N N1 0.24292(17) 1.04190(6) 0.47613(9) 0.0152(2) Uani d . 1 . .
N N2 0.21030(18) 0.99921(7) 0.18571(9) 0.0182(2) Uani d . 1 . .
C C1 0.2410(2) 1.04273(7) 0.70239(11) 0.0150(2) Uani d . 1 . .
C C2 0.2479(2) 1.04255(8) 0.81837(11) 0.0179(3) Uani d . 1 . .
C C3 0.2877(2) 0.96778(8) 0.88407(11) 0.0172(3) Uani d . 1 . .
C C4 0.3177(2) 0.88841(8) 0.83642(11) 0.0149(2) Uani d . 1 . .
C C5 0.3597(2) 0.81113(8) 0.90574(12) 0.0184(3) Uani d . 1 . .
C C6 0.3833(2) 0.73399(8) 0.85954(12) 0.0201(3) Uani d . 1 . .
C C7 0.3626(2) 0.73093(8) 0.74058(12) 0.0207(3) Uani d . 1 . .
C C8 0.3253(2) 0.80526(8) 0.67215(12) 0.0177(3) Uani d . 1 . .
C C9 0.30404(19) 0.88660(7) 0.71809(11) 0.0141(2) Uani d . 1 . .
C C10 0.26908(19) 0.96648(7) 0.65075(11) 0.0138(2) Uani d . 1 . .
C C11 0.2611(2) 0.96861(8) 0.53223(11) 0.0148(2) Uani d . 1 . .
C C12 0.2289(2) 1.04637(7) 0.36180(11) 0.0146(2) Uani d . 1 . .
C C13 0.1957(2) 1.11763(7) 0.29069(11) 0.0140(2) Uani d . 1 . .
C C14 0.18303(19) 1.08332(8) 0.18048(11) 0.0151(2) Uani d . 1 . .
C C15 0.1393(2) 1.13268(9) 0.06759(12) 0.0201(3) Uani d . 1 . .
C C16 0.1737(2) 1.20938(8) 0.31960(12) 0.0175(3) Uani d . 1 . .
H H2A 0.222(3) 1.0979(12) 0.8512(16) 0.029(5) Uiso d . 1 . .
H H3A 0.290(3) 0.9681(11) 0.9648(16) 0.024(4) Uiso d . 1 . .
H H5A 0.375(3) 0.8132(11) 0.9894(16) 0.027(4) Uiso d . 1 . .
H H6A 0.416(3) 0.6822(12) 0.9078(16) 0.027(4) Uiso d . 1 . .
H H7A 0.376(3) 0.6775(12) 0.7059(16) 0.029(5) Uiso d . 1 . .
H H8A 0.309(3) 0.8009(11) 0.5908(15) 0.022(4) Uiso d . 1 . .
H H11A 0.272(3) 0.9140(11) 0.4942(15) 0.026(4) Uiso d . 1 . .
H H15A 0.091(3) 1.0970(12) 0.0011(17) 0.032(5) Uiso d . 1 . .
H H15B 0.256(3) 1.1642(14) 0.0772(18) 0.043(6) Uiso d . 1 . .
H H15C 0.034(3) 1.1763(14) 0.0517(18) 0.043(6) Uiso d . 1 . .
H H16A 0.202(3) 1.2197(12) 0.4021(18) 0.036(5) Uiso d . 1 . .
H H16B 0.263(4) 1.2459(16) 0.302(2) 0.053(6) Uiso d . 1 . .
H H16C 0.041(4) 1.2329(14) 0.266(2) 0.047(6) Uiso d . 1 . .
H H1O1 0.207(4) 1.1091(15) 0.569(2) 0.055(7) Uiso 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 0.0016 '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 H1O1 . . 105.9(14) ?
C12 O2 N2 . . 107.29(9) ?
C11 N1 C12 . . 122.26(10) ?
C14 N2 O2 . . 105.86(9) ?
O1 C1 C10 . . 122.65(11) ?
O1 C1 C2 . . 116.06(10) ?
C10 C1 C2 . . 121.28(11) ?
C3 C2 C1 . . 120.22(11) ?
C3 C2 H2A . . 120.6(10) ?
C1 C2 H2A . . 119.2(10) ?
C2 C3 C4 . . 121.00(11) ?
C2 C3 H3A . . 119.7(10) ?
C4 C3 H3A . . 119.3(10) ?
C5 C4 C9 . . 119.85(11) ?
C5 C4 C3 . . 120.52(11) ?
C9 C4 C3 . . 119.63(11) ?
C6 C5 C4 . . 121.03(12) ?
C6 C5 H5A . . 119.4(10) ?
C4 C5 H5A . . 119.5(10) ?
C5 C6 C7 . . 119.55(12) ?
C5 C6 H6A . . 120.8(11) ?
C7 C6 H6A . . 119.7(11) ?
C8 C7 C6 . . 120.58(12) ?
C8 C7 H7A . . 118.5(11) ?
C6 C7 H7A . . 120.9(11) ?
C7 C8 C9 . . 121.36(12) ?
C7 C8 H8A . . 118.6(10) ?
C9 C8 H8A . . 120.0(10) ?
C8 C9 C4 . . 117.57(11) ?
C8 C9 C10 . . 123.34(11) ?
C4 C9 C10 . . 119.09(11) ?
C1 C10 C11 . . 120.06(10) ?
C1 C10 C9 . . 118.69(11) ?
C11 C10 C9 . . 121.25(10) ?
N1 C11 C10 . . 120.54(11) ?
N1 C11 H11A . . 120.0(10) ?
C10 C11 H11A . . 119.5(10) ?
C13 C12 O2 . . 111.11(10) ?
C13 C12 N1 . . 127.84(11) ?
O2 C12 N1 . . 121.01(10) ?
C12 C13 C14 . . 103.35(10) ?
C12 C13 C16 . . 128.48(11) ?
C14 C13 C16 . . 128.16(11) ?
N2 C14 C13 . . 112.37(11) ?
N2 C14 C15 . . 120.98(11) ?
C13 C14 C15 . . 126.63(11) ?
C14 C15 H15A . . 111.2(12) ?
C14 C15 H15B . . 110.3(12) ?
H15A C15 H15B . . 112.1(18) ?
C14 C15 H15C . . 110.3(12) ?
H15A C15 H15C . . 106.4(16) ?
H15B C15 H15C . . 106.3(18) ?
C13 C16 H16A . . 114.9(11) ?
C13 C16 H16B . . 109.5(14) ?
H16A C16 H16B . . 107.7(18) ?
C13 C16 H16C . . 112.3(13) ?
H16A C16 H16C . . 108.8(19) ?
H16B C16 H16C . . 102.8(19) ?
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 . 1.3448(14) ?
O1 H1O1 . 0.97(2) ?
O2 C12 . 1.3635(14) ?
O2 N2 . 1.4229(13) ?
N1 C11 . 1.3036(15) ?
N1 C12 . 1.3739(15) ?
N2 C14 . 1.3138(16) ?
C1 C10 . 1.4033(16) ?
C1 C2 . 1.4147(17) ?
C2 C3 . 1.3659(17) ?
C2 H2A . 1.004(19) ?
C3 C4 . 1.4245(17) ?
C3 H3A . 0.991(18) ?
C4 C5 . 1.4203(17) ?
C4 C9 . 1.4231(16) ?
C5 C6 . 1.3696(19) ?
C5 H5A . 0.990(18) ?
C6 C7 . 1.4108(19) ?
C6 H6A . 0.962(18) ?
C7 C8 . 1.3787(17) ?
C7 H7A . 0.957(19) ?
C8 C9 . 1.4198(16) ?
C8 H8A . 0.962(17) ?
C9 C10 . 1.4457(16) ?
C10 C11 . 1.4431(16) ?
C11 H11A . 0.989(18) ?
C12 C13 . 1.3607(16) ?
C13 C14 . 1.4274(16) ?
C13 C16 . 1.4912(16) ?
C14 C15 . 1.4920(17) ?
C15 H15A . 0.916(19) ?
C15 H15B . 0.96(2) ?
C15 H15C . 0.99(2) ?
C16 H16A . 0.96(2) ?
C16 H16B . 0.98(3) ?
C16 H16C . 0.98(2) ?
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
_geom_hbond_publ_flag
O1 H1O1 N1 . 0.97(2) 1.66(3) 2.5471(15) 150(2) yes
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
C12 O2 N2 C14 . . . . 0.20(14) ?
O1 C1 C2 C3 . . . . -179.34(12) ?
C10 C1 C2 C3 . . . . 1.7(2) ?
C1 C2 C3 C4 . . . . -1.7(2) ?
C2 C3 C4 C5 . . . . 179.74(13) ?
C2 C3 C4 C9 . . . . -0.7(2) ?
C9 C4 C5 C6 . . . . -1.5(2) ?
C3 C4 C5 C6 . . . . 178.15(13) ?
C4 C5 C6 C7 . . . . -0.9(2) ?
C5 C6 C7 C8 . . . . 2.1(2) ?
C6 C7 C8 C9 . . . . -0.8(2) ?
C7 C8 C9 C4 . . . . -1.5(2) ?
C7 C8 C9 C10 . . . . 178.66(13) ?
C5 C4 C9 C8 . . . . 2.64(19) ?
C3 C4 C9 C8 . . . . -176.96(12) ?
C5 C4 C9 C10 . . . . -177.54(12) ?
C3 C4 C9 C10 . . . . 2.85(19) ?
O1 C1 C10 C11 . . . . 1.1(2) ?
C2 C1 C10 C11 . . . . 179.96(13) ?
O1 C1 C10 C9 . . . . -178.36(12) ?
C2 C1 C10 C9 . . . . 0.5(2) ?
C8 C9 C10 C1 . . . . 177.05(13) ?
C4 C9 C10 C1 . . . . -2.75(19) ?
C8 C9 C10 C11 . . . . -2.4(2) ?
C4 C9 C10 C11 . . . . 177.78(12) ?
C12 N1 C11 C10 . . . . -178.04(12) ?
C1 C10 C11 N1 . . . . 5.2(2) ?
C9 C10 C11 N1 . . . . -175.36(12) ?
N2 O2 C12 C13 . . . . -1.01(15) ?
N2 O2 C12 N1 . . . . 176.88(12) ?
C11 N1 C12 C13 . . . . 175.02(14) ?
C11 N1 C12 O2 . . . . -2.5(2) ?
O2 C12 C13 C14 . . . . 1.33(15) ?
N1 C12 C13 C14 . . . . -176.38(13) ?
O2 C12 C13 C16 . . . . -179.77(13) ?
N1 C12 C13 C16 . . . . 2.5(2) ?
O2 N2 C14 C13 . . . . 0.64(15) ?
O2 N2 C14 C15 . . . . -177.96(12) ?
C12 C13 C14 N2 . . . . -1.23(16) ?
C16 C13 C14 N2 . . . . 179.86(13) ?
C12 C13 C14 C15 . . . . 177.28(13) ?
C16 C13 C14 C15 . . . . -1.6(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24744817
