#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/94/2209468.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_2209468
loop_
_publ_author_name
'Yan, Xiao-Chen'
'Wang, Hai-Bo'
'Liu, Zhi-Qian'
_publ_section_title
;
 [3-(2-Chlorophenyl)-1,2,4-oxadiazol-5-yl]methanol
;
_journal_coeditor_code           DN2034
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3007
_journal_page_last               o3008
_journal_paper_doi               10.1107/S1600536806018952
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C9 H7 Cl N2 O2'
_chemical_formula_moiety         'C9 H7 Cl N2 O2'
_chemical_formula_sum            'C9 H7 Cl N2 O2'
_chemical_formula_weight         210.62
_chemical_name_systematic
;
[3-(2-Chlorophenyl)-1,2,4-oxadiazol-5-yl]methanol
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 106.76(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.4280(15)
_cell_length_b                   14.202(3)
_cell_length_c                   8.8050(18)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      14
_cell_measurement_theta_min      10
_cell_volume                     889.4(3)
_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
;
ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows
(Farrugia, 1997) and PLATON (Spek, 2003)'
;
_computing_publication_material  SHELXS97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0172
_diffrn_reflns_av_sigmaI/netI    0.0288
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            1874
_diffrn_reflns_theta_full        25.97
_diffrn_reflns_theta_max         25.97
_diffrn_reflns_theta_min         2.81
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.400
_exptl_absorpt_correction_T_max  0.8893
_exptl_absorpt_correction_T_min  0.8563
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.442
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1739
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0488
_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)+(0.0683P)²+0.2802P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1237
_refine_ls_wR_factor_ref         0.1321
_reflns_number_gt                1399
_reflns_number_total             1739
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn2034.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 'Monoclinic' changed to 'monoclinic'
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_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2209468
_cod_database_fobs_code          2209468
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
Cl Cl 0.98974(10) 0.60467(5) 1.25390(8) 0.0505(3) Uani d . 1
O O1 0.6049(3) 0.60845(13) 0.4271(2) 0.0545(5) Uani d . 1
H H1 0.5542 0.5615 0.3792 0.082 Uiso calc R 1
O O2 0.6763(3) 0.68865(12) 0.7876(2) 0.0504(5) Uani d . 1
N N1 0.6071(3) 0.53892(14) 0.7618(2) 0.0355(5) Uani d . 1
N N2 0.7568(3) 0.64753(16) 0.9380(3) 0.0496(6) Uani d . 1
C C1 0.4965(4) 0.6430(2) 0.5231(3) 0.0491(7) Uani d . 1
H H1A 0.3721 0.6151 0.4903 0.059 Uiso calc R 1
H H1B 0.4830 0.7108 0.5110 0.059 Uiso calc R 1
C C2 0.5909(3) 0.61933(16) 0.6925(3) 0.0367(6) Uani d . 1
C C3 0.7127(3) 0.55880(16) 0.9152(3) 0.0332(5) Uani d . 1
C C4 0.7651(3) 0.48467(16) 1.0370(3) 0.0339(5) Uani d . 1
C C5 0.8854(3) 0.49710(17) 1.1898(3) 0.0372(6) Uani d . 1
C C6 0.9279(4) 0.4228(2) 1.2959(3) 0.0490(7) Uani d . 1
H H6 1.0089 0.4320 1.3972 0.059 Uiso calc R 1
C C7 0.8501(4) 0.3348(2) 1.2514(3) 0.0521(7) Uani d . 1
H H7 0.8782 0.2850 1.3231 0.063 Uiso calc R 1
C C8 0.7319(4) 0.32103(19) 1.1022(3) 0.0491(7) Uani d . 1
H H8 0.6795 0.2620 1.0723 0.059 Uiso calc R 1
C C9 0.6905(4) 0.39446(16) 0.9965(3) 0.0415(6) Uani d . 1
H H9 0.6107 0.3840 0.8951 0.050 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
Cl 0.0496(4) 0.0528(4) 0.0428(4) -0.0063(3) 0.0033(3) -0.0091(3)
O1 0.0591(13) 0.0546(12) 0.0489(11) -0.0123(9) 0.0142(10) -0.0076(9)
O2 0.0523(11) 0.0358(10) 0.0516(11) -0.0051(8) -0.0030(9) 0.0062(8)
N1 0.0316(10) 0.0360(11) 0.0364(10) 0.0018(8) 0.0058(8) -0.0010(8)
N2 0.0519(13) 0.0403(12) 0.0449(12) -0.0060(10) -0.0046(10) 0.0033(10)
C1 0.0449(14) 0.0478(15) 0.0473(15) 0.0044(12) 0.0019(12) 0.0054(12)
C2 0.0279(11) 0.0368(13) 0.0437(13) 0.0010(10) 0.0076(10) -0.0005(10)
C3 0.0237(10) 0.0341(12) 0.0414(13) -0.0002(9) 0.0086(9) -0.0028(10)
C4 0.0265(11) 0.0373(12) 0.0387(12) 0.0031(9) 0.0108(9) 0.0013(10)
C5 0.0311(12) 0.0442(14) 0.0386(12) 0.0023(10) 0.0137(10) -0.0031(10)
C6 0.0464(15) 0.0591(17) 0.0397(14) 0.0096(13) 0.0095(12) 0.0051(13)
C7 0.0560(17) 0.0478(16) 0.0547(16) 0.0142(13) 0.0195(14) 0.0150(13)
C8 0.0487(15) 0.0389(14) 0.0602(17) 0.0020(12) 0.0167(13) 0.0053(12)
C9 0.0379(13) 0.0397(13) 0.0447(14) 0.0011(11) 0.0085(11) -0.0005(11)
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 O1 H1 109.5
C2 O2 N2 106.30(18)
C2 N1 C3 103.40(19)
C3 N2 O2 103.63(19)
O1 C1 C2 109.6(2)
O1 C1 H1A 109.8
C2 C1 H1A 109.8
O1 C1 H1B 109.8
C2 C1 H1B 109.8
H1A C1 H1B 108.2
N1 C2 O2 113.4(2)
N1 C2 C1 128.9(2)
O2 C2 C1 117.6(2)
N2 C3 N1 113.3(2)
N2 C3 C4 125.2(2)
N1 C3 C4 121.5(2)
C5 C4 C9 117.2(2)
C5 C4 C3 125.0(2)
C9 C4 C3 117.8(2)
C6 C5 C4 120.9(2)
C6 C5 Cl 117.3(2)
C4 C5 Cl 121.85(19)
C5 C6 C7 120.1(2)
C5 C6 H6 120.0
C7 C6 H6 120.0
C8 C7 C6 120.0(2)
C8 C7 H7 120.0
C6 C7 H7 120.0
C7 C8 C9 120.0(3)
C7 C8 H8 120.0
C9 C8 H8 120.0
C8 C9 C4 121.8(2)
C8 C9 H9 119.1
C4 C9 H9 119.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl C5 1.732(3)
O1 C1 1.413(4)
O1 H1 0.8200
O2 C2 1.329(3)
O2 N2 1.413(3)
N1 C2 1.284(3)
N1 C3 1.382(3)
N2 C3 1.303(3)
C1 C2 1.492(3)
C1 H1A 0.9700
C1 H1B 0.9700
C3 C4 1.473(3)
C4 C5 1.395(3)
C4 C9 1.400(3)
C5 C6 1.384(4)
C6 C7 1.386(4)
C6 H6 0.9300
C7 C8 1.368(4)
C7 H7 0.9300
C8 C9 1.372(3)
C8 H8 0.9300
C9 H9 0.9300
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
O1 H1 N1 3_666 0.82 2.04 2.849(3) 169.9
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 13667957
