#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/05/2210573.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_2210573
loop_
_publ_author_name
'Yan, Xiao-Chen'
'Wang, Hai-Bo'
'Liu, Zhi-Qian'
_publ_section_title
;
 [3-(4-Chlorophenyl)-1,2,4-oxadiazol-5-yl]methanol
;
_journal_coeditor_code           DN2054
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4226
_journal_page_last               o4227
_journal_paper_doi               10.1107/S1600536806024433
_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-(4-Chlorophenyl)-1,2,4-oxadiazol-5-yl]methanol
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 127.56(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   27.789(2)
_cell_length_b                   4.0141(5)
_cell_length_c                   21.4570(15)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      11
_cell_measurement_theta_min      9
_cell_volume                     1897.3(8)
_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) 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 0.990
_diffrn_measured_fraction_theta_max 0.990
_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  0.0531
_diffrn_reflns_av_sigmaI/netI    0.0623
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1746
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         1.85
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.375
_exptl_absorpt_correction_T_max  0.9634
_exptl_absorpt_correction_T_min  0.9287
_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             864
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.144
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.987
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         1746
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.987
_refine_ls_R_factor_all          0.1531
_refine_ls_R_factor_gt           0.0659
_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)+(0.03P)²+2P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1163
_refine_ls_wR_factor_ref         0.1486
_reflns_number_gt                698
_reflns_number_total             1746
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn2054.cif
_cod_data_source_block           I
_cod_original_cell_volume        1897.4(8)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2210573
_cod_database_fobs_code          2210573
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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 0.22383(7) 0.3303(5) -0.19207(10) 0.1168(7) Uani d . 1
O O1 0.57455(16) 0.0814(12) 0.1728(2) 0.0933(13) Uani d . 1
O O2 0.5716(2) -0.4789(12) 0.3012(3) 0.0991(15) Uani d . 1
N N1 0.5237(2) 0.1959(14) 0.0977(3) 0.0951(16) Uani d . 1
N N2 0.49330(19) -0.1140(12) 0.1556(3) 0.0796(13) Uani d . 1
C C1 0.2970(3) 0.2514(17) -0.1106(4) 0.0929(19) Uani d . 1
C C2 0.3450(3) 0.3529(17) -0.1091(3) 0.0952(19) Uani d . 1
H H2C 0.3379 0.4602 -0.1524 0.114 Uiso calc R 1
C C3 0.4039(2) 0.2945(17) -0.0428(3) 0.0897(18) Uani d . 1
H H3A 0.4363 0.3658 -0.0415 0.108 Uiso calc R 1
C C4 0.4150(3) 0.1310(17) 0.0217(3) 0.0827(16) Uani d . 1
C C5 0.3658(3) 0.0226(17) 0.0182(3) 0.097(2) Uani d . 1
H H5A 0.3725 -0.0919 0.0605 0.116 Uiso calc R 1
C C6 0.3070(3) 0.0846(18) -0.0481(4) 0.099(2) Uani d . 1
H H6A 0.2743 0.0127 -0.0500 0.119 Uiso calc R 1
C C7 0.4782(2) 0.0707(15) 0.0919(3) 0.0774(15) Uani d . 1
C C8 0.5516(3) -0.0955(16) 0.2024(3) 0.0843(17) Uani d . 1
C C9 0.5970(2) -0.2373(16) 0.2818(3) 0.0908(18) Uani d . 1
H H9A 0.6298 -0.3369 0.2840 0.109 Uiso calc R 1
H H9B 0.6140 -0.0593 0.3204 0.109 Uiso calc R 1
H H 0.555(3) -0.368(17) 0.316(3) 0.109 Uiso d . 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 0.0821(10) 0.1361(15) 0.1023(12) 0.0064(12) 0.0408(9) 0.0006(13)
O1 0.067(2) 0.129(4) 0.082(3) 0.001(3) 0.045(2) 0.002(3)
O2 0.097(3) 0.101(4) 0.107(3) 0.006(3) 0.066(3) 0.005(3)
N1 0.084(3) 0.118(4) 0.087(3) -0.010(3) 0.054(3) -0.001(3)
N2 0.071(3) 0.082(3) 0.085(3) -0.006(3) 0.047(3) -0.007(3)
C1 0.080(4) 0.104(5) 0.090(4) 0.001(4) 0.049(4) -0.005(4)
C2 0.088(4) 0.114(5) 0.082(4) 0.002(4) 0.051(4) -0.001(4)
C3 0.074(4) 0.110(5) 0.085(4) -0.005(4) 0.048(3) -0.006(4)
C4 0.079(4) 0.094(4) 0.074(4) -0.001(3) 0.046(3) -0.002(3)
C5 0.090(4) 0.124(6) 0.080(4) -0.010(4) 0.053(4) 0.002(4)
C6 0.074(4) 0.116(6) 0.099(5) -0.013(4) 0.049(4) -0.006(4)
C7 0.078(4) 0.085(4) 0.082(4) -0.009(3) 0.055(3) -0.006(3)
C8 0.082(4) 0.088(4) 0.091(4) 0.000(4) 0.057(4) -0.002(4)
C9 0.082(4) 0.095(5) 0.093(4) 0.005(4) 0.052(4) 0.001(4)
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
C8 O1 N1 106.0(4)
C9 O2 H 104(5)
C7 N1 O1 102.8(5)
C8 N2 C7 102.7(5)
C6 C1 C2 120.5(6)
C6 C1 Cl 119.6(5)
C2 C1 Cl 119.8(5)
C1 C2 C3 119.7(6)
C1 C2 H2C 120.2
C3 C2 H2C 120.2
C4 C3 C2 120.6(6)
C4 C3 H3A 119.7
C2 C3 H3A 119.7
C3 C4 C5 118.7(5)
C3 C4 C7 119.8(5)
C5 C4 C7 121.5(6)
C6 C5 C4 120.3(6)
C6 C5 H5A 119.9
C4 C5 H5A 119.9
C1 C6 C5 120.1(6)
C1 C6 H6A 120.0
C5 C6 H6A 120.0
N1 C7 N2 115.2(5)
N1 C7 C4 121.3(6)
N2 C7 C4 123.5(5)
N2 C8 O1 113.4(5)
N2 C8 C9 131.2(6)
O1 C8 C9 115.5(5)
O2 C9 C8 112.1(5)
O2 C9 H9A 109.2
C8 C9 H9A 109.2
O2 C9 H9B 109.2
C8 C9 H9B 109.2
H9A C9 H9B 107.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl C1 1.720(6)
O1 C8 1.344(6)
O1 N1 1.424(5)
O2 C9 1.403(7)
O2 H 0.83(6)
N1 C7 1.293(6)
N2 C8 1.287(6)
N2 C7 1.377(6)
C1 C6 1.368(8)
C1 C2 1.375(7)
C2 C3 1.386(7)
C2 H2C 0.9300
C3 C4 1.386(7)
C3 H3A 0.9300
C4 C5 1.391(7)
C4 C7 1.479(7)
C5 C6 1.386(7)
C5 H5A 0.9300
C6 H6A 0.9300
C8 C9 1.483(7)
C9 H9A 0.9700
C9 H9B 0.9700
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
_geom_hbond_publ_flag
O2 H N2 2_655 0.83(8) 2.05(9) 2.880(9) 175(8) yes
C9 H9B O2 1_565 0.9700 2.5300 3.209(8) 127.00 yes
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
C8 O1 N1 C7 -1.0(6)
C6 C1 C2 C3 -2.0(10)
Cl C1 C2 C3 178.8(5)
C1 C2 C3 C4 0.8(10)
C2 C3 C4 C5 0.8(10)
C2 C3 C4 C7 179.9(6)
C3 C4 C5 C6 -1.4(10)
C7 C4 C5 C6 179.5(6)
C2 C1 C6 C5 1.4(10)
Cl C1 C6 C5 -179.4(5)
C4 C5 C6 C1 0.3(10)
O1 N1 C7 N2 0.5(7)
O1 N1 C7 C4 179.4(5)
C8 N2 C7 N1 0.3(7)
C8 N2 C7 C4 -178.7(6)
C3 C4 C7 N1 6.9(9)
C5 C4 C7 N1 -174.1(6)
C3 C4 C7 N2 -174.3(6)
C5 C4 C7 N2 4.8(9)
C7 N2 C8 O1 -1.0(7)
C7 N2 C8 C9 179.7(6)
N1 O1 C8 N2 1.3(7)
N1 O1 C8 C9 -179.2(5)
N2 C8 C9 O2 13.2(9)
O1 C8 C9 O2 -166.1(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2044094
