#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/01/2230192.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_2230192
loop_
_publ_author_name
'Gündoğdu, Cevher'
'Alp, Serap'
'Ergün, Yavuz'
'Tercan, Barış'
'Hökelek, Tuncer'
_publ_section_title
;
 2-(Naphthalen-1-yl)-4-(naphthalen-1-ylmethylidene)-1,3-oxazol-5(4H)-one
;
_journal_coeditor_code           XU5196
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1258
_journal_page_last               o1259
_journal_paper_doi               10.1107/S1600536811015340
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C24 H15 N O2'
_chemical_formula_moiety         'C24 H15 N O2'
_chemical_formula_sum            'C24 H15 N O2'
_chemical_formula_weight         349.37
_chemical_name_systematic
;
2-(Naphthalen-1-yl)-4-(naphthalen-1-ylmethylidene)-1,3-oxazol-5(4H)-one
;
_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                 107.212(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.6927(5)
_cell_length_b                   6.0646(2)
_cell_length_c                   15.6262(5)
_cell_measurement_reflns_used    3844
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.78
_cell_measurement_theta_min      2.28
_cell_volume                     1692.11(9)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material
'WinGX (Farrugia, 1999) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD area-detector'
_diffrn_measurement_method       'φ and 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  0.0609
_diffrn_reflns_av_sigmaI/netI    0.0432
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            29257
_diffrn_reflns_theta_full        28.45
_diffrn_reflns_theta_max         28.45
_diffrn_reflns_theta_min         1.14
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9861
_exptl_absorpt_correction_T_min  0.9642
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.254
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         4260
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0780
_refine_ls_R_factor_gt           0.0439
_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)+(0.0712P)²+0.0940P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1098
_refine_ls_wR_factor_ref         0.1359
_reflns_number_gt                2911
_reflns_number_total             4260
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu5196.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2230192
_cod_database_fobs_code          2230192
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_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.44739(6) -0.05303(17) 1.11266(7) 0.0226(3) Uani d . 1 1 . .
O O2 0.51969(6) 0.2213(2) 1.08529(8) 0.0339(3) Uani d . 1 1 . .
N N1 0.33689(7) 0.0161(2) 1.00801(8) 0.0182(3) Uani d . 1 1 . .
C C1 0.30409(8) 0.4225(2) 0.88040(10) 0.0183(3) Uani d . 1 1 . .
C C2 0.24089(8) 0.2914(2) 0.85707(10) 0.0183(3) Uani d . 1 1 . .
H H2 0.2421 0.1521 0.8852 0.022 Uiso calc R 1 1 . .
C C3 0.17453(8) 0.3596(2) 0.79239(10) 0.0185(3) Uani d . 1 1 . .
C C4 0.11021(9) 0.2236(3) 0.76755(11) 0.0231(4) Uani d . 1 1 . .
H H4 0.1109 0.0848 0.7960 0.028 Uiso calc R 1 1 . .
C C5 0.04717(9) 0.2900(3) 0.70303(11) 0.0263(4) Uani d . 1 1 . .
H H5 0.0044 0.1969 0.6866 0.032 Uiso calc R 1 1 . .
C C6 0.04523(9) 0.4962(3) 0.66073(11) 0.0265(4) Uani d . 1 1 . .
H H6 0.0012 0.5407 0.6156 0.032 Uiso calc R 1 1 . .
C C7 0.10607(9) 0.6326(3) 0.68407(10) 0.0230(4) Uani d . 1 1 . .
H H7 0.1038 0.7716 0.6554 0.028 Uiso calc R 1 1 . .
C C8 0.17232(8) 0.5692(2) 0.75047(10) 0.0188(3) Uani d . 1 1 . .
C C9 0.23747(9) 0.7022(2) 0.77577(10) 0.0208(3) Uani d . 1 1 . .
H H9 0.2368 0.8431 0.7490 0.025 Uiso calc R 1 1 . .
C C10 0.30132(9) 0.6317(2) 0.83806(10) 0.0200(3) Uani d . 1 1 . .
H H10 0.3444 0.7234 0.8533 0.024 Uiso calc R 1 1 . .
C C11 0.37403(8) 0.3572(2) 0.94585(10) 0.0197(3) Uani d . 1 1 . .
H H11 0.4156 0.4516 0.9508 0.024 Uiso calc R 1 1 . .
C C12 0.38719(8) 0.1798(2) 1.00029(10) 0.0191(3) Uani d . 1 1 . .
C C13 0.45933(9) 0.1340(3) 1.06678(11) 0.0227(4) Uani d . 1 1 . .
C C14 0.37283(8) -0.1109(2) 1.07250(10) 0.0175(3) Uani d . 1 1 . .
C C15 0.34675(8) -0.3067(2) 1.10825(10) 0.0179(3) Uani d . 1 1 . .
C C16 0.39709(9) -0.4187(3) 1.17708(10) 0.0217(3) Uani d . 1 1 . .
H H16 0.4460 -0.3605 1.2022 0.026 Uiso calc R 1 1 . .
C C17 0.37753(9) -0.6171(3) 1.21081(10) 0.0229(4) Uani d . 1 1 . .
H H17 0.4126 -0.6898 1.2592 0.027 Uiso calc R 1 1 . .
C C18 0.30808(9) -0.7050(2) 1.17389(10) 0.0212(3) Uani d . 1 1 . .
H H18 0.2961 -0.8434 1.1947 0.025 Uiso calc R 1 1 . .
C C19 0.25329(9) -0.5932(2) 1.10494(10) 0.0192(3) Uani d . 1 1 . .
C C20 0.18039(9) -0.6812(3) 1.07013(10) 0.0227(4) Uani d . 1 1 . .
H H20 0.1690 -0.8202 1.0909 0.027 Uiso calc R 1 1 . .
C C21 0.12628(9) -0.5699(3) 1.00735(11) 0.0254(4) Uani d . 1 1 . .
H H21 0.0775 -0.6308 0.9846 0.031 Uiso calc R 1 1 . .
C C22 0.14316(9) -0.3641(3) 0.97648(11) 0.0238(4) Uani d . 1 1 . .
H H22 0.1052 -0.2854 0.9334 0.029 Uiso calc R 1 1 . .
C C23 0.21331(8) -0.2757(3) 1.00745(10) 0.0202(3) Uani d . 1 1 . .
H H23 0.2234 -0.1371 0.9852 0.024 Uiso calc R 1 1 . .
C C24 0.27132(8) -0.3873(2) 1.07232(10) 0.0172(3) Uani d . 1 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
C14 O1 C13 . . 105.32(11) ?
C14 N1 C12 . . 106.50(13) ?
C2 C1 C10 . . 118.66(14) ?
C2 C1 C11 . . 123.31(14) ?
C10 C1 C11 . . 118.03(13) ?
C1 C2 C3 . . 121.52(14) ?
C1 C2 H2 . . 119.2 ?
C3 C2 H2 . . 119.2 ?
C2 C3 C4 . . 121.43(14) ?
C2 C3 C8 . . 119.38(14) ?
C4 C3 C8 . . 119.18(14) ?
C3 C4 H4 . . 119.7 ?
C5 C4 C3 . . 120.55(15) ?
C5 C4 H4 . . 119.7 ?
C4 C5 C6 . . 120.32(15) ?
C4 C5 H5 . . 119.8 ?
C6 C5 H5 . . 119.8 ?
C5 C6 H6 . . 119.7 ?
C7 C6 C5 . . 120.53(15) ?
C7 C6 H6 . . 119.7 ?
C6 C7 C8 . . 120.72(15) ?
C6 C7 H7 . . 119.6 ?
C8 C7 H7 . . 119.6 ?
C7 C8 C3 . . 118.68(14) ?
C7 C8 C9 . . 122.97(14) ?
C9 C8 C3 . . 118.32(13) ?
C8 C9 H9 . . 119.4 ?
C10 C9 C8 . . 121.21(14) ?
C10 C9 H9 . . 119.4 ?
C1 C10 H10 . . 119.5 ?
C9 C10 C1 . . 120.91(14) ?
C9 C10 H10 . . 119.5 ?
C1 C11 H11 . . 115.9 ?
C12 C11 C1 . . 128.18(14) ?
C12 C11 H11 . . 115.9 ?
N1 C12 C13 . . 107.81(13) ?
C11 C12 N1 . . 128.32(14) ?
C11 C12 C13 . . 123.81(14) ?
O1 C13 C12 . . 105.36(12) ?
O2 C13 O1 . . 121.07(14) ?
O2 C13 C12 . . 133.56(15) ?
O1 C14 C15 . . 115.87(12) ?
N1 C14 O1 . . 114.99(13) ?
N1 C14 C15 . . 129.14(14) ?
C16 C15 C14 . . 118.16(14) ?
C16 C15 C24 . . 119.98(14) ?
C24 C15 C14 . . 121.84(13) ?
C15 C16 C17 . . 121.39(14) ?
C15 C16 H16 . . 119.3 ?
C17 C16 H16 . . 119.3 ?
C16 C17 H17 . . 120.1 ?
C18 C17 C16 . . 119.81(14) ?
C18 C17 H17 . . 120.1 ?
C17 C18 C19 . . 121.13(14) ?
C17 C18 H18 . . 119.4 ?
C19 C18 H18 . . 119.4 ?
C18 C19 C24 . . 119.71(14) ?
C20 C19 C18 . . 120.54(14) ?
C20 C19 C24 . . 119.73(14) ?
C19 C20 H20 . . 119.5 ?
C21 C20 C19 . . 121.06(15) ?
C21 C20 H20 . . 119.5 ?
C20 C21 C22 . . 119.51(15) ?
C20 C21 H21 . . 120.2 ?
C22 C21 H21 . . 120.2 ?
C21 C22 H22 . . 119.5 ?
C23 C22 C21 . . 121.06(15) ?
C23 C22 H22 . . 119.5 ?
C22 C23 C24 . . 121.11(14) ?
C22 C23 H23 . . 119.4 ?
C24 C23 H23 . . 119.4 ?
C19 C24 C15 . . 117.75(13) ?
C23 C24 C15 . . 124.75(14) ?
C23 C24 C19 . . 117.50(14) ?
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 C13 . 1.3949(18) ?
O1 C14 . 1.3935(17) ?
O2 C13 . 1.2015(18) ?
N1 C12 . 1.3971(18) ?
N1 C14 . 1.2880(18) ?
C1 C2 . 1.380(2) ?
C1 C10 . 1.424(2) ?
C2 C3 . 1.411(2) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.414(2) ?
C3 C8 . 1.425(2) ?
C4 C5 . 1.365(2) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.410(2) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.366(2) ?
C6 H6 . 0.9500 ?
C7 H7 . 0.9500 ?
C8 C7 . 1.413(2) ?
C9 C8 . 1.416(2) ?
C9 H9 . 0.9500 ?
C10 C9 . 1.367(2) ?
C10 H10 . 0.9500 ?
C11 C1 . 1.456(2) ?
C11 H11 . 0.9500 ?
C12 C11 . 1.348(2) ?
C12 C13 . 1.465(2) ?
C15 C14 . 1.456(2) ?
C15 C16 . 1.380(2) ?
C16 H16 . 0.9500 ?
C17 C16 . 1.404(2) ?
C17 H17 . 0.9500 ?
C18 C17 . 1.364(2) ?
C18 H18 . 0.9500 ?
C19 C18 . 1.420(2) ?
C20 C19 . 1.414(2) ?
C20 H20 . 0.9500 ?
C21 C20 . 1.361(2) ?
C21 C22 . 1.407(2) ?
C21 H21 . 0.9500 ?
C22 C23 . 1.366(2) ?
C22 H22 . 0.9500 ?
C23 C24 . 1.418(2) ?
C23 H23 . 0.9500 ?
C24 C15 . 1.440(2) ?
C24 C19 . 1.426(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
C2 H2 N1 . 0.95 2.34 3.0110(19) 127 yes
C10 H10 O2 3_667 0.95 2.46 3.324(2) 152 yes
C11 H11 O2 3_667 0.95 2.47 3.3601(18) 155 yes
C23 H23 N1 . 0.95 2.25 2.908(2) 126 yes
C9 H9 Cg4 4_554 0.95 2.87 3.543(2) 129 yes
C18 H18 Cg1 4_565 0.95 2.61 3.381(2) 139 yes
C20 H20 Cg2 4_565 0.95 2.75 3.450(2) 131 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
C14 O1 C13 O2 . . . . -178.58(15) ?
C14 O1 C13 C12 . . . . 1.12(15) ?
C13 O1 C14 N1 . . . . -0.25(17) ?
C13 O1 C14 C15 . . . . 179.03(12) ?
C14 N1 C12 C11 . . . . -175.61(16) ?
C14 N1 C12 C13 . . . . 1.47(16) ?
C12 N1 C14 O1 . . . . -0.79(17) ?
C12 N1 C14 C15 . . . . -179.96(15) ?
C10 C1 C2 C3 . . . . 0.4(2) ?
C11 C1 C2 C3 . . . . -179.11(13) ?
C2 C1 C10 C9 . . . . 0.2(2) ?
C11 C1 C10 C9 . . . . 179.72(14) ?
C1 C2 C3 C4 . . . . 178.99(14) ?
C1 C2 C3 C8 . . . . -0.4(2) ?
C2 C3 C4 C5 . . . . -178.21(14) ?
C8 C3 C4 C5 . . . . 1.2(2) ?
C2 C3 C8 C7 . . . . 178.33(14) ?
C2 C3 C8 C9 . . . . -0.1(2) ?
C4 C3 C8 C7 . . . . -1.1(2) ?
C4 C3 C8 C9 . . . . -179.54(13) ?
C3 C4 C5 C6 . . . . -0.5(2) ?
C4 C5 C6 C7 . . . . -0.4(2) ?
C3 C8 C7 C6 . . . . 0.2(2) ?
C5 C6 C7 C8 . . . . 0.5(2) ?
C9 C8 C7 C6 . . . . 178.61(14) ?
C10 C9 C8 C3 . . . . 0.7(2) ?
C10 C9 C8 C7 . . . . -177.68(14) ?
C1 C10 C9 C8 . . . . -0.7(2) ?
C12 C11 C1 C2 . . . . -8.0(3) ?
C12 C11 C1 C10 . . . . 172.50(15) ?
N1 C12 C11 C1 . . . . -0.7(3) ?
C13 C12 C11 C1 . . . . -177.33(14) ?
N1 C12 C13 O1 . . . . -1.62(16) ?
N1 C12 C13 O2 . . . . 178.04(18) ?
C11 C12 C13 O1 . . . . 175.62(14) ?
C11 C12 C13 O2 . . . . -4.7(3) ?
C16 C15 C14 O1 . . . . -0.7(2) ?
C16 C15 C14 N1 . . . . 178.50(15) ?
C24 C15 C14 O1 . . . . -179.11(12) ?
C24 C15 C14 N1 . . . . 0.1(2) ?
C14 C15 C16 C17 . . . . -175.58(14) ?
C24 C15 C16 C17 . . . . 2.9(2) ?
C18 C17 C16 C15 . . . . 1.6(2) ?
C19 C18 C17 C16 . . . . -3.6(2) ?
C20 C19 C18 C17 . . . . -177.05(14) ?
C24 C19 C18 C17 . . . . 1.2(2) ?
C21 C20 C19 C18 . . . . 176.55(14) ?
C21 C20 C19 C24 . . . . -1.7(2) ?
C22 C21 C20 C19 . . . . 0.1(2) ?
C20 C21 C22 C23 . . . . 1.0(2) ?
C21 C22 C23 C24 . . . . -0.5(2) ?
C22 C23 C24 C15 . . . . 179.71(13) ?
C22 C23 C24 C19 . . . . -1.0(2) ?
C19 C24 C15 C14 . . . . 173.26(13) ?
C19 C24 C15 C16 . . . . -5.2(2) ?
C23 C24 C15 C14 . . . . -7.5(2) ?
C23 C24 C15 C16 . . . . 174.11(14) ?
C15 C24 C19 C18 . . . . 3.2(2) ?
C15 C24 C19 C20 . . . . -178.59(13) ?
C23 C24 C19 C18 . . . . -176.15(13) ?
C23 C24 C19 C20 . . . . 2.1(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 17945732
