#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/58/2015841.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_2015841
loop_
_publ_author_name
'Vratislav Langer'
'Eva Scholtzová'
'Dalma Gyepesová'
'Jozef Lustoň'
'Juraj Kronek'
_publ_section_title
;
 2-(2-Oxazolin-2-yl)benzene-1,4-diol: X-ray and density functional
 theory studies
;
_journal_coeditor_code           DN2121
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o187
_journal_page_last               o189
_journal_paper_doi               10.1107/S0108270107004131
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C9 H9 N O3'
_chemical_formula_moiety         'C9 H9 N O3'
_chemical_formula_sum            'C9 H9 N O3'
_chemical_formula_weight         179.17
_chemical_melting_point          389
_chemical_name_common
;
2-(2,5-dihydroxyphenyl)-2-oxazoline
;
_chemical_name_systematic
;
2-(2-Oxazolin-2-yl)benzene-1,4-diol
;
_space_group_IT_number           43
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'F 2 -2d'
_symmetry_space_group_name_H-M   'F d d 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   24.4297(3)
_cell_length_b                   31.7167(7)
_cell_length_c                   4.44090(10)
_cell_measurement_reflns_used    3265
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.42
_cell_measurement_theta_min      2.57
_cell_volume                     3440.94(12)
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2003)'
_computing_data_reduction        'SAINT and SADABS (Sheldrick, 2003)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2006)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker, 2003)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_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  0.0729
_diffrn_reflns_av_sigmaI/netI    0.0321
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            9919
_diffrn_reflns_theta_full        26.42
_diffrn_reflns_theta_max         26.42
_diffrn_reflns_theta_min         2.57
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.9958
_exptl_absorpt_correction_T_min  0.5126
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          1.00
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.176
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         1010
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0365
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.055P)²+2.545P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0879
_refine_ls_wR_factor_ref         0.0963
_reflns_number_gt                840
_reflns_number_total             1010
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn2121.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.

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.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2015841
_cod_database_fobs_code          2015841
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'
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
O O1 -0.13506(6) 0.06136(5) 0.5991(5) 0.0329(5) Uani d . 1
O O5 0.02876(7) 0.06893(6) 0.3460(5) 0.0382(5) Uani d . 1
H H5 0.0134 0.0532 0.4727 0.065(12) Uiso calc R 1
O O8 -0.11289(7) 0.19201(6) -0.0585(6) 0.0433(6) Uani d . 1
H H8 -0.1454 0.1875 -0.0050 0.056(11) Uiso calc R 1
N N1 -0.04979(8) 0.03503(6) 0.6357(6) 0.0330(6) Uani d . 1
C C1 -0.08141(9) 0.06343(7) 0.5294(6) 0.0250(6) Uani d . 1
C C2 -0.08311(11) 0.00695(8) 0.8252(7) 0.0342(7) Uani d . 1
H H2A -0.0707 0.0079 1.0374 0.045(9) Uiso calc R 1
H H2B -0.0812 -0.0225 0.7523 0.034(7) Uiso calc R 1
C C3 -0.14114(11) 0.02448(8) 0.7942(8) 0.0385(7) Uani d . 1
H H3A -0.1658 0.0034 0.7015 0.060(10) Uiso calc R 1
H H3B -0.1561 0.0327 0.9931 0.050(10) Uiso calc R 1
C C4 -0.06306(10) 0.09721(7) 0.3334(6) 0.0248(6) Uani d . 1
C C5 -0.00738(9) 0.09864(7) 0.2496(7) 0.0287(6) Uani d . 1
C C6 0.01071(10) 0.13077(7) 0.0664(7) 0.0340(7) Uani d . 1
H H6 0.0482 0.1318 0.0096 0.028(7) Uiso calc R 1
C C7 -0.02479(10) 0.16149(8) -0.0358(8) 0.0345(7) Uani d . 1
H H7 -0.0118 0.1834 -0.1631 0.031(7) Uiso calc R 1
C C8 -0.07983(10) 0.16025(7) 0.0484(7) 0.0304(6) Uani d . 1
C C9 -0.09858(10) 0.12836(7) 0.2298(7) 0.0275(6) Uani d . 1
H H9 -0.1361 0.1275 0.2853 0.025(7) Uiso calc R 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0230(9) 0.0299(9) 0.0459(12) 0.0017(7) 0.0112(9) 0.0110(10)
O5 0.0211(9) 0.0378(10) 0.0557(14) 0.0069(8) 0.0053(9) 0.0138(11)
O8 0.0261(10) 0.0389(10) 0.0650(17) 0.0037(8) 0.0027(10) 0.0225(11)
N1 0.0292(11) 0.0287(11) 0.0411(15) 0.0045(9) 0.0029(11) 0.0086(11)
C1 0.0204(11) 0.0264(12) 0.0283(15) 0.0003(9) 0.0045(11) -0.0032(12)
C2 0.0375(15) 0.0275(12) 0.0376(17) 0.0008(11) 0.0080(14) 0.0043(14)
C3 0.0376(15) 0.0319(14) 0.0460(19) -0.0023(12) 0.0113(14) 0.0124(15)
C4 0.0208(11) 0.0243(11) 0.0293(14) -0.0003(9) 0.0039(10) -0.0026(12)
C5 0.0198(12) 0.0284(13) 0.0380(17) 0.0008(10) 0.0015(12) -0.0014(13)
C6 0.0189(11) 0.0380(14) 0.0450(18) -0.0011(11) 0.0049(13) 0.0070(15)
C7 0.0286(13) 0.0333(13) 0.0414(17) -0.0053(11) 0.0042(13) 0.0105(13)
C8 0.0234(12) 0.0293(12) 0.0385(17) 0.0000(10) -0.0016(12) 0.0052(13)
C9 0.0193(11) 0.0291(12) 0.0342(16) -0.0011(10) 0.0018(11) 0.0005(12)
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
C1 O1 C3 105.88(18)
C5 O5 H5 109.5
C8 O8 H8 109.5
C1 N1 C2 107.7(2)
N1 C1 O1 117.9(2)
N1 C1 C4 123.7(2)
O1 C1 C4 118.3(2)
N1 C2 C3 104.0(2)
N1 C2 H2A 111.0
C3 C2 H2A 111.0
N1 C2 H2B 111.0
C3 C2 H2B 111.0
H2A C2 H2B 109.0
O1 C3 C2 104.5(2)
O1 C3 H3A 110.9
C2 C3 H3A 110.9
O1 C3 H3B 110.9
C2 C3 H3B 110.9
H3A C3 H3B 108.9
C9 C4 C5 119.4(2)
C9 C4 C1 121.9(2)
C5 C4 C1 118.7(2)
O5 C5 C6 119.4(2)
O5 C5 C4 121.4(2)
C6 C5 C4 119.3(2)
C5 C6 C7 121.0(2)
C5 C6 H6 119.5
C7 C6 H6 119.5
C8 C7 C6 119.8(2)
C8 C7 H7 120.1
C6 C7 H7 120.1
C9 C8 O8 123.1(2)
C9 C8 C7 120.0(2)
O8 C8 C7 116.9(2)
C8 C9 C4 120.6(2)
C8 C9 H9 119.7
C4 C9 H9 119.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 1.348(3) y
N1 C1 1.277(3) y
C1 C4 1.451(3) y
O1 C3 1.463(3) ?
O5 C5 1.361(3) y
O5 H5 0.8400 ?
O8 C8 1.375(3) y
O8 H8 0.8400 ?
N1 C2 1.471(3) ?
C2 C3 1.529(4) ?
C2 H2A 0.9900 ?
C2 H2B 0.9900 ?
C3 H3A 0.9900 ?
C3 H3B 0.9900 ?
C4 C9 1.393(3) ?
C4 C5 1.411(3) ?
C5 C6 1.377(3) ?
C6 C7 1.381(4) ?
C6 H6 0.9500 ?
C7 C8 1.396(3) ?
C7 H7 0.9500 ?
C8 C9 1.372(4) ?
C9 H9 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
_geom_torsion_publ_flag
C2 N1 C1 O1 -1.9(4) y
C2 N1 C1 C4 179.4(2) ?
C3 O1 C1 N1 0.7(3) y
C3 O1 C1 C4 179.5(2) ?
C1 N1 C2 C3 2.2(3) y
C1 O1 C3 C2 0.7(3) y
N1 C2 C3 O1 -1.7(3) y
N1 C1 C4 C9 -178.0(3) y
O1 C1 C4 C9 3.4(4) y
N1 C1 C4 C5 1.2(4) y
O1 C1 C4 C5 -177.5(3) y
C9 C4 C5 O5 179.9(2) ?
C1 C4 C5 O5 0.7(4) ?
C9 C4 C5 C6 -0.1(4) ?
C1 C4 C5 C6 -179.3(2) ?
O5 C5 C6 C7 180.0(3) ?
C4 C5 C6 C7 0.0(4) ?
C5 C6 C7 C8 0.4(4) ?
C6 C7 C8 C9 -0.6(4) ?
C6 C7 C8 O8 179.3(3) ?
O8 C8 C9 C4 -179.5(3) ?
C7 C8 C9 C4 0.5(4) ?
C5 C4 C9 C8 -0.1(4) ?
C1 C4 C9 C8 179.0(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21133261
