#------------------------------------------------------------------------------
#$Date: 2022-10-03 17:40:12 +0300 (Mon, 03 Oct 2022) $
#$Revision: 278324 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/14/2001470.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_2001470
loop_
_publ_author_name
'Yip, B.-C.'
'Fun, H.-K.'
'Teoh, S.-G.'
'Shawkataly, O. B.'
_publ_section_title
;
 Structure of 2-(1-naphthyl)-5-phenyl-1,3-oxazole (α-NPO)
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1532
_journal_page_last               1534
_journal_paper_doi               10.1107/S0108270193001192
_journal_volume                  49
_journal_year                    1993
_chemical_formula_sum            'C19 H13 N O'
_chemical_formula_weight         271.3
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_type_scat_source
' SHELXTL/PC (Siemens Crystallographic Research Systems, 1990)'
_cell_angle_alpha                90.0
_cell_angle_beta                 99.44(2)
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   15.722(3)
_cell_length_b                   3.9060(10)
_cell_length_c                   21.969(4)
_cell_measurement_reflns_used    50
_cell_measurement_temperature    298
_cell_measurement_theta_max      17.5
_cell_measurement_theta_min      2.5
_cell_volume                     1330.8(5)
_diffrn_measurement_device       'Siemens P4'
_diffrn_measurement_method       2θ/θ
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0123
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            3637
_diffrn_reflns_theta_max         22.5
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 200
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.076
_exptl_absorpt_correction_T_min  0.879
_exptl_absorpt_correction_type   analytical
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_meas      1.345
_exptl_crystal_description       Needles
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.13
_refine_diff_density_min         -0.15
_refine_ls_goodness_of_fit_obs   1.09
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     242
_refine_ls_number_reflns         1306
_refine_ls_R_factor_obs          0.0382
_refine_ls_shift/esd_max         0.046
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[σ²F + 0.0002F²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.0338
_reflns_number_observed          1306
_reflns_number_total             3058
_reflns_observed_criterion       F>4\s(F)
_cod_data_source_file            li1036.cif
_cod_data_source_block           li1036_structure_1_of_1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value '1/[\s^2^F + 0.0002F^2^]' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w = 1/[\s^2^F +
0.0002F^2^]'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_formula_sum        'C19 H13 N1 O1'
_cod_database_code               2001470
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x+1/2,-y+1/2,z+1/2
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
N .04500(10) .2499(6) .07800(10) .0480(10)
O .17020(10) -.0121(4) .10860(10) .0380(10)
C(1) .2390(2) .0692(8) -.04350(10) .0510(10)
C(2) .3088(2) .0023(9) -.07160(10) .0590(10)
C(3) .3826(2) -.1361(9) -.03850(10) .0590(10)
C(4) .3858(2) -.2126(9) .02280(10) .0560(10)
C(5) .3154(2) -.1468(8) .05150(10) .0450(10)
C(6) .2412(2) -.0010(7) .01880(10) .0360(10)
C(7) .1672(2) .0799(7) .04790(10) .0360(10)
C(8) .0919(2) .2373(8) .03010(10) .0470(10)
C(9) .09360(10) .0983(7) .12360(10) .0350(10)
C(10) .08060(10) .0293(7) .18690(10) .0330(10)
C(11) .1463(2) -.1258(7) .22680(10) .0390(10)
C(12) .1394(2) -.1948(8) .28790(10) .0430(10)
C(13) .0662(2) -.1160(8) .30980(10) .0440(10)
C(14) -.00390(10) .0421(7) .27150(10) .0370(10)
C(15) -.0800(2) .1253(8) .29440(10) .0460(10)
C(16) -.1472(2) .2783(8) .25800(10) .0490(10)
C(17) -.1416(2) .3528(8) .19670(10) .0490(10)
C(18) -.0698(2) .2780(8) .17240(10) .0430(10)
C(19) .00230(10) .1189(6) .20900(10) .0340(10)
H(1) .1866(16) .182(8) -.0668(11) ?
H(2) .3037(15) .063(7) -.1143(11) ?
H(3) .4342(14) -.186(6) -.0597(10) ?
H(4) .4380(15) -.333(7) .0442(10) ?
H(5) .3183(13) -.201(7) .0953(10) ?
H(8) .0716(14) .352(6) -.0091(10) ?
H(11) .1956(12) -.194(6) .2095(8) ?
H(12) .1883(13) -.307(6) .3144(9) ?
H(13) .0592(12) -.177(6) .3523(10) ?
H(15) -.0828(12) .083(6) .3391(9) ?
H(16) -.2007(13) .332(6) .2751(9) ?
H(17) -.1881(13) .470(6) .1702(10) ?
H(18) -.0642(12) .335(6) .1290(9) ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C(8) N C(9) 104.5(2) yes
C(2) C(1) C(6) 120.9(2) yes
C(6) C(1) H(1) 118.6(15) yes
C(1) C(2) H(2) 116.8(15) yes
C(2) C(3) C(4) 119.7(3) yes
C(4) C(3) H(3) 120.3(12) yes
C(3) C(4) H(4) 117.4(14) yes
C(4) C(5) C(6) 120.6(2) yes
C(6) C(5) H(5) 119.7(12) yes
C(1) C(6) C(7) 119.8(2) yes
O C(7) C(6) 117.8(2) yes
C(6) C(7) C(8) 135.2(2) yes
N C(8) H(8) 121.1(14) yes
N C(9) O 112.8(2) yes
O C(9) C(10) 115.9(2) yes
C(9) C(10) C(19) 122.5(2) yes
C(10) C(11) C(12) 122.0(2) yes
C(12) C(11) H(11) 121.8(11) yes
C(11) C(12) H(12) 118.7(13) yes
C(12) C(13) C(14) 121.0(2) yes
C(14) C(13) H(13) 118.0(12) yes
C(13) C(14) C(19) 119.6(2) yes
C(14) C(15) C(16) 121.1(2) yes
C(16) C(15) H(15) 119.6(11) yes
C(15) C(16) H(16) 119.7(11) yes
C(16) C(17) C(18) 121.5(2) yes
C(18) C(17) H(17) 117.3(13) yes
C(17) C(18) H(18) 122.5(12) yes
C(10) C(19) C(14) 118.2(2) yes
C(14) C(19) C(18) 117.6(2) yes
C(7) O C(9) 105.0(2) yes
C(2) C(1) H(1) 120.4(15) yes
C(1) C(2) C(3) 120.4(3) yes
C(3) C(2) H(2) 122.8(15) yes
C(2) C(3) H(3) 120.0(12) yes
C(3) C(4) C(5) 120.1(3) yes
C(5) C(4) H(4) 122.2(14) yes
C(4) C(5) H(5) 119.7(12) yes
C(1) C(6) C(5) 118.3(2) yes
C(5) C(6) C(7) 121.9(2) yes
O C(7) C(8) 107.0(2) yes
N C(8) C(7) 110.7(2) yes
C(7) C(8) H(8) 128.0(14) yes
N C(9) C(10) 131.3(2) yes
C(9) C(10) C(11) 118.5(2) yes
C(11) C(10) C(19) 119.0(2) yes
C(10) C(11) H(11) 116.1(11) yes
C(11) C(12) C(13) 120.2(2) yes
C(13) C(12) H(12) 121.0(13) yes
C(12) C(13) H(13) 121.0(12) yes
C(13) C(14) C(15) 120.9(2) yes
C(15) C(14) C(19) 119.4(2) yes
C(14) C(15) H(15) 119.2(11) yes
C(15) C(16) C(17) 119.7(3) yes
C(17) C(16) H(16) 120.6(11) yes
C(16) C(17) H(17) 121.1(13) yes
C(17) C(18) C(19) 120.6(2) yes
C(19) C(18) H(18) 116.9(12) yes
C(10) C(19) C(18) 124.2(2) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N C(8) 1.382(3) yes
O C(7) 1.375(3) yes
C(1) C(2) 1.370(4) yes
C(1) H(1) 1.00(3) yes
C(2) H(2) .96(2) yes
C(3) H(3) 1.02(2) yes
C(4) H(4) .99(2) yes
C(5) H(5) .98(2) yes
C(7) C(8) 1.333(4) yes
C(9) C(10) 1.463(3) yes
C(10) C(19) 1.438(3) yes
C(11) H(11) .96(2) yes
C(12) H(12) .99(2) yes
C(13) H(13) .99(2) yes
C(14) C(19) 1.425(3) yes
C(15) H(15) 1.00(2) yes
C(16) H(16) 1.00(2) yes
C(17) H(17) .97(2) yes
C(18) H(18) 1.00(2) yes
N C(9) 1.299(3) yes
O C(9) 1.370(3) yes
C(1) C(6) 1.389(3) yes
C(2) C(3) 1.375(4) yes
C(3) C(4) 1.374(4) yes
C(4) C(5) 1.384(4) yes
C(5) C(6) 1.388(3) yes
C(6) C(7) 1.451(4) yes
C(8) H(8) .98(2) yes
C(10) C(11) 1.381(3) yes
C(11) C(12) 1.389(4) yes
C(12) C(13) 1.353(4) yes
C(13) C(14) 1.414(3) yes
C(14) C(15) 1.409(4) yes
C(15) C(16) 1.354(4) yes
C(16) C(17) 1.395(4) yes
C(17) C(18) 1.357(4) yes
C(18) C(19) 1.420(3) yes
