#------------------------------------------------------------------------------
#$Date: 2025-08-19 23:06:29 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301812 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/68/4026840.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4026840
loop_
_publ_author_name
'Weihua Chen'
'Eric B. Twum'
'Linlin Li'
'Brian D. Wright'
'Peter L. Rinaldi'
'Yi Pang'
_publ_section_title
;
 Rotational Energy Barrier of 2-(2',6'-Dihydroxyphenyl)benzoxazole: A Case
 Study by NMR
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              285
_journal_page_last               290
_journal_paper_doi               10.1021/jo201890f
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C13 H9 N O3'
_chemical_formula_sum            'C13 H9 N O3'
_chemical_formula_weight         227.21
_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                 101.652(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.301(10)
_cell_length_b                   4.863(3)
_cell_length_c                   13.818(8)
_cell_measurement_reflns_used    1951
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.25
_cell_measurement_theta_min      2.55
_cell_volume                     1072.8(11)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0979
_diffrn_reflns_av_sigmaI/netI    0.0894
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6934
_diffrn_reflns_theta_full        26.28
_diffrn_reflns_theta_max         26.28
_diffrn_reflns_theta_min         2.55
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.9960
_exptl_absorpt_correction_T_min  0.1907
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_description       Rod
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.89
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.890
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2099
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.890
_refine_ls_R_factor_all          0.1100
_refine_ls_R_factor_gt           0.0679
_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)+(0.1075P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1644
_refine_ls_wR_factor_ref         0.1784
_reflns_number_gt                1214
_reflns_number_total             2099
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo201890f_si_002.cif
_cod_data_source_block           bw
_cod_original_cell_volume        1072.7(11)
_cod_original_sg_symbol_H-M      'P 1 21/c 1 '
_cod_database_code               4026840
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_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.25002(12) 0.5685(4) 0.26584(14) 0.0330(5) Uani 1 1 d .
O2 O 0.13308(12) 0.9597(4) 0.20000(14) 0.0382(6) Uani 1 1 d .
H2 H 0.1716 0.8503 0.1941 0.057 Uiso 1 1 calc R
O3 O 0.22505(13) 0.7746(4) 0.55739(14) 0.0422(6) Uani 1 1 d .
H3 H 0.2586 0.6678 0.5376 0.063 Uiso 1 1 calc R
N1 N 0.29434(14) 0.4860(4) 0.43135(17) 0.0319(6) Uani 1 1 d .
C1 C 0.17637(17) 0.9064(6) 0.4775(2) 0.0332(7) Uani 1 1 d .
C2 C 0.11906(18) 1.1050(6) 0.4970(2) 0.0387(8) Uani 1 1 d .
H2A H 0.1141 1.1429 0.5630 0.046 Uiso 1 1 calc R
C3 C 0.06920(18) 1.2467(6) 0.4177(2) 0.0393(8) Uani 1 1 d .
H3A H 0.0302 1.3800 0.4307 0.047 Uiso 1 1 calc R
C4 C 0.07591(17) 1.1950(6) 0.3200(2) 0.0358(7) Uani 1 1 d .
H4 H 0.0423 1.2956 0.2676 0.043 Uiso 1 1 calc R
C5 C 0.13213(17) 0.9948(5) 0.2988(2) 0.0310(7) Uani 1 1 d .
C6 C 0.18385(17) 0.8452(5) 0.37805(19) 0.0293(7) Uani 1 1 d .
C7 C 0.24334(17) 0.6304(5) 0.36277(19) 0.0304(7) Uani 1 1 d .
C8 C 0.31216(17) 0.3624(5) 0.2767(2) 0.0319(7) Uani 1 1 d .
C9 C 0.34190(18) 0.2256(6) 0.2018(2) 0.0370(7) Uani 1 1 d .
H9 H 0.3223 0.2659 0.1338 0.044 Uiso 1 1 calc R
C10 C 0.40322(19) 0.0233(6) 0.2346(2) 0.0411(8) Uani 1 1 d .
H10 H 0.4261 -0.0769 0.1873 0.049 Uiso 1 1 calc R
C11 C 0.43160(18) -0.0341(6) 0.3368(3) 0.0420(8) Uani 1 1 d .
H11 H 0.4728 -0.1724 0.3561 0.050 Uiso 1 1 calc R
C12 C 0.40030(19) 0.1084(6) 0.4100(2) 0.0402(8) Uani 1 1 d .
H12 H 0.4196 0.0696 0.4782 0.048 Uiso 1 1 calc R
C13 C 0.33911(18) 0.3110(6) 0.3782(2) 0.0337(7) Uani 1 1 d .
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
C7 O1 C8 104.1(2)
C7 N1 C13 105.2(2)
O3 C1 C2 117.5(3)
O3 C1 C6 121.6(2)
C2 C1 C6 120.9(3)
C3 C2 C1 119.3(3)
C4 C3 C2 121.2(3)
C3 C4 C5 120.4(3)
O2 C5 C4 115.4(2)
O2 C5 C6 124.7(2)
C4 C5 C6 119.9(3)
C1 C6 C5 118.3(2)
C1 C6 C7 118.1(2)
C5 C6 C7 123.6(2)
N1 C7 O1 114.3(2)
N1 C7 C6 127.6(2)
O1 C7 C6 118.2(2)
C9 C8 C13 124.7(3)
C9 C8 O1 127.5(3)
C13 C8 O1 107.8(2)
C8 C9 C10 115.1(3)
C9 C10 C11 121.5(3)
C12 C11 C10 121.7(3)
C11 C12 C13 117.3(3)
C8 C13 C12 119.6(3)
C8 C13 N1 108.7(2)
C12 C13 N1 131.7(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C7 1.398(3)
O1 C8 1.411(3)
O2 C5 1.380(3)
O3 C1 1.380(3)
N1 C7 1.328(3)
N1 C13 1.418(4)
C1 C2 1.407(4)
C1 C6 1.435(4)
C2 C3 1.406(4)
C3 C4 1.399(4)
C4 C5 1.407(4)
C5 C6 1.437(4)
C6 C7 1.469(4)
C8 C9 1.397(4)
C8 C13 1.405(4)
C9 C10 1.410(4)
C10 C11 1.423(5)
C11 C12 1.403(4)
C12 C13 1.408(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659441
2 PubChem 136802412
