#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/26/2202651.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_2202651
loop_
_publ_author_name
'Marilyn M. Olmstead'
'Javad J. Sahbari'
_publ_section_title
;
 Acetylacetone dioxime
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1648
_journal_page_last               o1649
_journal_paper_doi               10.1107/S1600536803021731
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C5 H10 N2 O2'
_chemical_formula_moiety         'C5 H10 N2 O2'
_chemical_formula_sum            'C5 H10 N2 O2'
_chemical_formula_weight         130.15
_chemical_name_common            'acetylacetone dioxime'
_chemical_name_systematic
;
 pentane-2,4-dione dioxime
;
_space_group_IT_number           118
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P -4 -2n'
_symmetry_space_group_name_H-M   'P -4 n 2'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.852(2)
_cell_length_b                   10.852(2)
_cell_length_c                   5.9751(15)
_cell_measurement_reflns_used    48
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      27.0
_cell_measurement_theta_min      8.1
_cell_volume                     703.7(3)
_computing_cell_refinement       P3-PC
_computing_data_collection       'P3-PC (Siemens, 1991)'
_computing_data_reduction        'XDISK (Siemens, 1991)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1994)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      130(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Syntex P2₁'
_diffrn_measurement_method       2θ-ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_sigmaI/netI    0.0188
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            777
_diffrn_reflns_theta_full        66.82
_diffrn_reflns_theta_max         66.82
_diffrn_reflns_theta_min         5.77
_diffrn_standards_decay_%        <0.1
_diffrn_standards_interval_count 198
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.802
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.125
_refine_diff_density_min         -0.113
_refine_ls_extinction_coef       0.025(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     63
_refine_ls_number_reflns         598
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.121
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0279
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0428P)²+0.1006P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0769
_refine_ls_wR_factor_ref         0.0783
_reflns_number_gt                577
_reflns_number_total             598
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fl6064.cif
_cod_data_source_block           I
_cod_database_code               2202651
_cod_database_fobs_code          2202651
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'y, -x, -z'
'-y, x, -z'
'x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'y+1/2, x+1/2, -z+1/2'
'-y+1/2, -x+1/2, -z+1/2'
loop_
_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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1 0.33898(10) 0.40570(10) 0.2077(2) 0.0345(4) Uani d . 1 . . O
H1 0.390(2) 0.383(2) 0.076(5) 0.057(7) Uiso d . 1 . . H
N1 0.31472(12) 0.52870(11) 0.1520(3) 0.0288(4) Uani d . 1 . . N
C1 0.24110(13) 0.58023(13) 0.2909(3) 0.0288(4) Uani d . 1 . . C
C2 0.18573(18) 0.51634(19) 0.4866(3) 0.0393(5) Uani d . 1 . . C
H2A 0.122(2) 0.565(2) 0.557(5) 0.065(8) Uiso d . 1 . . H
H2B 0.149(2) 0.436(2) 0.447(4) 0.052(7) Uiso d . 1 . . H
H2C 0.248(2) 0.496(3) 0.597(5) 0.069(8) Uiso d . 1 . . H
C3 0.21494(15) 0.71494(15) 0.2500 0.0372(6) Uani d S 1 . . C
H3 0.263(2) 0.744(2) 0.121(3) 0.049(6) Uiso d . 1 . . H
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
O1 0.0378(7) 0.0213(6) 0.0445(7) 0.0055(4) 0.0048(6) 0.0006(5)
N1 0.0238(6) 0.0206(7) 0.0420(8) 0.0000(5) 0.0015(6) -0.0002(5)
C1 0.0204(7) 0.0269(8) 0.0392(10) -0.0009(6) -0.0003(6) -0.0053(7)
C2 0.0398(10) 0.0452(11) 0.0329(10) 0.0068(9) 0.0045(8) -0.0008(9)
C3 0.0247(7) 0.0247(7) 0.0622(18) -0.0002(8) 0.0055(8) -0.0055(8)
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 O1 H1 . . 99.1(14) y
C1 N1 O1 . . 112.30(13) y
N1 C1 C2 . . 123.95(13) y
N1 C1 C3 . . 115.81(13) y
C2 C1 C3 . . 120.21(13) y
C1 C2 H2A . . 112.2(15) ?
C1 C2 H2B . . 112.8(14) ?
H2A C2 H2B . . 107(2) ?
C1 C2 H2C . . 111.2(15) ?
H2A C2 H2C . . 109(2) ?
H2B C2 H2C . . 104(2) ?
C1 C3 C1 . 7_455 113.00(18) y
C1 C3 H3 . . 109.7(14) ?
C1 C3 H3 7_455 . 109.3(14) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 N1 . 1.4007(16) y
O1 H1 . 0.99(3) y
N1 C1 . 1.281(2) y
C1 C2 . 1.486(3) y
C1 C3 . 1.5090(18) y
C2 H2A . 0.97(2) ?
C2 H2B . 0.99(2) ?
C2 H2C . 0.97(3) ?
C3 H3 . 0.98(2) y
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 4_655 0.99(3) 1.78(3) 2.767(2) 170(2)
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_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
H1 O1 N1 C1 . 175.6(14) y
O1 N1 C1 C2 . -1.1(2) y
O1 N1 C1 C3 . 177.05(13) y
N1 C1 C3 C1 7_455 119.77(15) y
C2 C1 C3 C1 7_455 -62.04(13) y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 7847962
