#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/91/2239126.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_2239126
loop_
_publ_author_name
'Arunakumar, D. B.'
'Nivedita, R. Desai'
'Sreenivasa, S.'
'Madan Kumar, S.'
'Lokanath, N. K.'
'Suchetan, P. A.'
_publ_section_title
;
 (1Z)-1-(1-Benzofuran-2-yl)ethanone oxime
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o40
_journal_paper_doi               10.1107/S1600536813033102
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C10 H9 N O2'
_chemical_formula_moiety         'C10 H9 N O2'
_chemical_formula_sum            'C10 H9 N O2'
_chemical_formula_weight         175.18
_chemical_melting_point          473
_chemical_name_systematic
;
(1Z)-1-(1-Benzofuran-2-yl)ethanone oxime
;
_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                 96.178(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.5727(12)
_cell_length_b                   4.7303(8)
_cell_length_c                   18.756(2)
_cell_measurement_reflns_used    1331
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      64.6
_cell_measurement_theta_min      4.7
_cell_volume                     844.4(2)
_computing_cell_refinement       'APEX2 and SAINT-Plus (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker, 2009)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.932
_diffrn_measured_fraction_theta_max 0.932
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_av_sigmaI/netI    0.0236
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       2
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            2478
_diffrn_reflns_theta_full        64.60
_diffrn_reflns_theta_max         64.60
_diffrn_reflns_theta_min         4.65
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.799
_exptl_absorpt_correction_T_max  0.839
_exptl_absorpt_correction_T_min  0.772
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.398
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         1333
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0652
_refine_ls_R_factor_gt           0.0621
_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)+(0.1028P)²+0.2023P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1431
_refine_ls_wR_factor_ref         0.1464
_reflns_number_gt                1199
_reflns_number_total             1333
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb7169sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2239126
_cod_database_fobs_code          2239126
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_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
_atom_site_symmetry_multiplicity
C C1 1.04643(18) 0.3538(4) 0.41182(10) 0.0348(5) Uani d . 1 1
C C2 1.06183(18) 0.5553(4) 0.35964(10) 0.0354(5) Uani d . 1 1
C C3 1.1963(2) 0.6670(5) 0.35443(12) 0.0458(6) Uani d . 1 1
H H3 1.2109 0.8023 0.3200 0.055 Uiso calc R 1 1
C C4 1.3051(2) 0.5706(5) 0.40151(12) 0.0464(6) Uani d . 1 1
H H4 1.3950 0.6408 0.3985 0.056 Uiso calc R 1 1
C C5 1.2848(2) 0.3703(5) 0.45370(12) 0.0473(6) Uani d . 1 1
H H5 1.3612 0.3125 0.4851 0.057 Uiso calc R 1 1
C C6 1.1547(2) 0.2556(5) 0.46007(12) 0.0464(6) Uani d . 1 1
H H6 1.1406 0.1206 0.4946 0.056 Uiso calc R 1 1
C C7 0.92452(19) 0.5946(4) 0.32240(10) 0.0377(5) Uani d . 1 1
H H7 0.9003 0.7176 0.2844 0.045 Uiso calc R 1 1
C C8 0.83702(18) 0.4191(4) 0.35294(9) 0.0318(5) Uani d . 1 1
C C9 0.68805(17) 0.3508(4) 0.34237(9) 0.0312(5) Uani d . 1 1
C C10 0.63408(19) 0.1283(5) 0.38897(11) 0.0402(5) Uani d . 1 1
H H10A 0.5356 0.0996 0.3752 0.060 Uiso calc R 1 1
H H10B 0.6482 0.1879 0.4381 0.060 Uiso calc R 1 1
H H10C 0.6838 -0.0453 0.3835 0.060 Uiso calc R 1 1
N N1 0.59615(15) 0.4690(3) 0.29671(8) 0.0351(4) Uani d . 1 1
O O1 0.90954(12) 0.2666(3) 0.40845(7) 0.0375(4) Uani d . 1 1
O O2 0.65313(13) 0.6771(3) 0.25538(7) 0.0417(4) Uani d . 1 1
H H2 0.5897 0.7764 0.2361 0.063 Uiso calc R 1 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
O1 C1 C6 125.18(18)
O1 C1 C2 110.42(15)
C6 C1 C2 124.40(17)
C1 C2 C3 118.42(17)
C1 C2 C7 105.77(16)
C3 C2 C7 135.81(19)
C4 C3 C2 118.0(2)
C4 C3 H3 121.0
C2 C3 H3 121.0
C3 C4 C5 121.75(18)
C3 C4 H4 119.1
C5 C4 H4 119.1
C6 C5 C4 121.77(19)
C6 C5 H5 119.1
C4 C5 H5 119.1
C5 C6 C1 115.7(2)
C5 C6 H6 122.2
C1 C6 H6 122.2
C8 C7 C2 106.98(17)
C8 C7 H7 126.5
C2 C7 H7 126.5
C7 C8 O1 110.76(15)
C7 C8 C9 136.28(17)
O1 C8 C9 112.96(15)
N1 C9 C8 125.71(18)
N1 C9 C10 116.12(15)
C8 C9 C10 118.16(15)
C9 C10 H10A 109.5
C9 C10 H10B 109.5
H10A C10 H10B 109.5
C9 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C9 N1 O2 113.26(14)
C1 O1 C8 106.06(14)
N1 O2 H2 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.369(2)
C1 C6 1.381(3)
C1 C2 1.385(3)
C2 C3 1.404(3)
C2 C7 1.433(3)
C3 C4 1.370(3)
C3 H3 0.9300
C4 C5 1.391(3)
C4 H4 0.9300
C5 C6 1.375(3)
C5 H5 0.9300
C6 H6 0.9300
C7 C8 1.350(3)
C7 H7 0.9300
C8 O1 1.390(2)
C8 C9 1.455(2)
C9 N1 1.288(2)
C9 C10 1.495(3)
C10 H10A 0.9600
C10 H10B 0.9600
C10 H10C 0.9600
N1 O2 1.400(2)
O2 H2 0.8200
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
O2 H2 N1 2_655 0.82 2.03 2.838(2) 166
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
O1 C1 C2 C3 -179.18(17)
C6 C1 C2 C3 0.6(3)
O1 C1 C2 C7 0.5(2)
C6 C1 C2 C7 -179.7(2)
C1 C2 C3 C4 -0.1(3)
C7 C2 C3 C4 -179.7(2)
C2 C3 C4 C5 -0.6(3)
C3 C4 C5 C6 1.0(4)
C4 C5 C6 C1 -0.5(3)
O1 C1 C6 C5 179.47(19)
C2 C1 C6 C5 -0.3(3)
C1 C2 C7 C8 -0.3(2)
C3 C2 C7 C8 179.2(2)
C2 C7 C8 O1 0.1(2)
C2 C7 C8 C9 -179.9(2)
C7 C8 C9 N1 -3.0(4)
O1 C8 C9 N1 177.02(16)
C7 C8 C9 C10 178.2(2)
O1 C8 C9 C10 -1.7(2)
C8 C9 N1 O2 0.6(3)
C10 C9 N1 O2 179.33(15)
C6 C1 O1 C8 179.8(2)
C2 C1 O1 C8 -0.4(2)
C7 C8 O1 C1 0.2(2)
C9 C8 O1 C1 -179.84(14)
