#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/14/2211425.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_2211425
loop_
_publ_author_name
'Ding, Wei-Lin'
'Shen, Yong-Mei'
'Xing, Zhi-Tao'
'Wang, Pin-Liang'
'Wang, Hai-Bo'
_publ_section_title
;
 2-[3-(4-Chlorophenyl)-1,2,4-oxadiazol-5-yl]phenol
;
_journal_coeditor_code           HB2194
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o5592
_journal_page_last               o5593
_journal_paper_doi               10.1107/S1600536806047052
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C14 H9 Cl N2 O2'
_chemical_formula_moiety         'C14 H9 Cl N2 O2'
_chemical_formula_sum            'C14 H9 Cl N2 O2'
_chemical_formula_weight         272.68
_chemical_name_systematic
;
2-[3-(4-Chlorophenyl)-1,2,4-oxadiazol-5-yl]phenol
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 97.98(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.3900(13)
_cell_length_b                   5.0380(10)
_cell_length_c                   19.255(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12
_cell_measurement_theta_min      9
_cell_volume                     613.9(2)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'SHELXTL (Siemens, 1996)'
_computing_publication_material  'PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_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  0.0460
_diffrn_reflns_av_sigmaI/netI    0.0565
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            1466
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         1.07
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.309
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_correction_T_min  0.913
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.229
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         1343
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0909
_refine_ls_R_factor_gt           0.0529
_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)+(0.0624P)²+0.1265P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1180
_refine_ls_wR_factor_ref         0.1397
_reflns_number_gt                904
_reflns_number_total             1343
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb2194.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2211425
_cod_database_fobs_code          2211425
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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
Cl Cl 0.9006(3) -0.4011(4) 0.04725(8) 0.0737(5) Uani d . 1
C C6 0.5783(8) 0.9310(12) 0.3471(3) 0.0498(13) Uani d . 1
O O1 0.9467(6) 0.8104(11) 0.3699(3) 0.0774(15) Uani d . 1
O O2 0.3393(6) 0.6909(9) 0.2622(2) 0.0629(12) Uani d . 1
N N1 0.3522(7) 0.4873(11) 0.2124(3) 0.0628(15) Uani d . 1
N N2 0.6734(6) 0.5767(12) 0.2703(2) 0.0480(11) Uani d . 1
C C1 0.4186(9) 1.0959(17) 0.3644(3) 0.0630(16) Uani d . 1
H H1B 0.2820 1.0776 0.3409 0.076 Uiso calc R 1
C C2 0.4606(11) 1.2861(15) 0.4160(3) 0.0724(19) Uani d . 1
H H2B 0.3531 1.3961 0.4271 0.087 Uiso calc R 1
C C3 0.6621(12) 1.3119(17) 0.4509(3) 0.076(2) Uani d . 1
H H3A 0.6905 1.4393 0.4859 0.091 Uiso calc R 1
C C4 0.8199(11) 1.1538(15) 0.4349(3) 0.070(2) Uani d . 1
H H4A 0.9559 1.1765 0.4584 0.084 Uiso calc R 1
C C5 0.7819(9) 0.9577(14) 0.3838(3) 0.0593(16) Uani d . 1
C C7 0.5387(8) 0.7289(13) 0.2950(3) 0.0496(14) Uani d . 1
C C8 0.5527(8) 0.4313(12) 0.2198(3) 0.0491(14) Uani d . 1
C C9 0.6360(8) 0.2240(12) 0.1771(3) 0.0478(13) Uani d . 1
C C10 0.8482(8) 0.1519(13) 0.1918(3) 0.0579(18) Uani d . 1
H H10A 0.9360 0.2336 0.2281 0.070 Uiso calc R 1
C C11 0.9271(9) -0.0437(14) 0.1515(3) 0.0612(16) Uani d . 1
H H11A 1.0673 -0.0973 0.1615 0.073 Uiso calc R 1
C C12 0.7985(10) -0.1555(12) 0.0977(3) 0.0557(15) Uani d . 1
C C13 0.5886(9) -0.0883(15) 0.0814(3) 0.0637(18) Uani d . 1
H H13A 0.5022 -0.1712 0.0450 0.076 Uiso calc R 1
C C14 0.5106(8) 0.1086(17) 0.1217(3) 0.0591(15) Uani d . 1
H H14A 0.3708 0.1628 0.1108 0.071 Uiso calc R 1
H H 0.903(9) 0.678(15) 0.327(3) 0.089 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'
Cl Cl 0.1484 0.1585 '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 C6 C5 119.0(6)
C1 C6 C7 122.0(5)
C5 C6 C7 119.0(5)
C5 O1 H 112(3)
C7 O2 N1 106.2(4)
C8 N1 O2 103.4(4)
C7 N2 C8 103.9(4)
C2 C1 C6 120.7(6)
C2 C1 H1B 119.6
C6 C1 H1B 119.6
C3 C2 C1 119.6(7)
C3 C2 H2B 120.2
C1 C2 H2B 120.2
C4 C3 C2 120.6(7)
C4 C3 H3A 119.7
C2 C3 H3A 119.7
C3 C4 C5 121.1(6)
C3 C4 H4A 119.4
C5 C4 H4A 119.4
O1 C5 C4 117.9(6)
O1 C5 C6 123.1(6)
C4 C5 C6 118.9(6)
N2 C7 O2 112.1(5)
N2 C7 C6 128.3(5)
O2 C7 C6 119.5(5)
N1 C8 N2 114.3(5)
N1 C8 C9 121.3(5)
N2 C8 C9 124.4(5)
C14 C9 C10 119.6(6)
C14 C9 C8 121.1(5)
C10 C9 C8 119.2(5)
C11 C10 C9 119.3(5)
C11 C10 H10A 120.4
C9 C10 H10A 120.4
C12 C11 C10 119.6(6)
C12 C11 H11A 120.2
C10 C11 H11A 120.2
C11 C12 C13 122.7(6)
C11 C12 Cl 119.0(5)
C13 C12 Cl 118.3(5)
C12 C13 C14 117.5(6)
C12 C13 H13A 121.3
C14 C13 H13A 121.3
C9 C14 C13 121.3(5)
C9 C14 H14A 119.4
C13 C14 H14A 119.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl C12 1.754(6)
C6 C1 1.392(8)
C6 C5 1.398(8)
C6 C7 1.428(8)
O1 C5 1.345(7)
O1 H 1.06(7)
O2 C7 1.355(6)
O2 N1 1.415(6)
N1 C8 1.300(7)
N2 C7 1.292(7)
N2 C8 1.367(7)
C1 C2 1.379(10)
C1 H1B 0.9300
C2 C3 1.374(9)
C2 H2B 0.9300
C3 C4 1.354(10)
C3 H3A 0.9300
C4 C5 1.391(9)
C4 H4A 0.9300
C8 C9 1.474(8)
C9 C14 1.372(8)
C9 C10 1.394(7)
C10 C11 1.392(8)
C10 H10A 0.9300
C11 C12 1.353(8)
C11 H11A 0.9300
C12 C13 1.376(8)
C13 C14 1.393(9)
C13 H13A 0.9300
C14 H14A 0.9300
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O1 H N2 1.06(7) 1.78(6) 2.680(6) 139(5)
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
C7 O2 N1 C8 -1.1(5)
C5 C6 C1 C2 1.1(9)
C7 C6 C1 C2 178.7(5)
C6 C1 C2 C3 -0.4(10)
C1 C2 C3 C4 0.4(11)
C2 C3 C4 C5 -1.3(11)
C3 C4 C5 O1 179.2(6)
C3 C4 C5 C6 2.1(9)
C1 C6 C5 O1 -178.9(6)
C7 C6 C5 O1 3.5(9)
C1 C6 C5 C4 -2.0(8)
C7 C6 C5 C4 -179.6(5)
C8 N2 C7 O2 -1.0(6)
C8 N2 C7 C6 -177.0(5)
N1 O2 C7 N2 1.3(6)
N1 O2 C7 C6 177.8(4)
C1 C6 C7 N2 174.3(6)
C5 C6 C7 N2 -8.1(8)
C1 C6 C7 O2 -1.5(8)
C5 C6 C7 O2 176.1(5)
O2 N1 C8 N2 0.6(6)
O2 N1 C8 C9 179.7(4)
C7 N2 C8 N1 0.2(7)
C7 N2 C8 C9 -178.9(5)
N1 C8 C9 C14 9.0(8)
N2 C8 C9 C14 -172.0(6)
N1 C8 C9 C10 -173.5(6)
N2 C8 C9 C10 5.5(8)
C14 C9 C10 C11 -2.4(9)
C8 C9 C10 C11 -180.0(5)
C9 C10 C11 C12 1.8(9)
C10 C11 C12 C13 -1.5(9)
C10 C11 C12 Cl 179.8(4)
C11 C12 C13 C14 1.8(9)
Cl C12 C13 C14 -179.5(5)
C10 C9 C14 C13 2.8(10)
C8 C9 C14 C13 -179.7(6)
C12 C13 C14 C9 -2.4(9)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21125930
