#------------------------------------------------------------------------------
#$Date: 2018-01-26 09:44:00 +0200 (Fri, 26 Jan 2018) $
#$Revision: 205693 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/81/2108187.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_2108187
loop_
_publ_author_name
'Truong, Khai-Nghi'
'Merkens, Carina'
'Meven, Martin'
'Faßbänder, Björn'
'Dronskowski, Richard'
'Englert, Ulli'
_publ_section_title
;
 Phase transition and proton ordering at 50K in
 3-(pyridin-4-yl)pentane-2,4-dione
;
_journal_coeditor_code           HW5050SUP1
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              1172
_journal_page_last               1178
_journal_paper_doi               10.1107/S2052520617015591
_journal_volume                  73
_journal_year                    2017
_chemical_formula_moiety         'C10 H11 N O2'
_chemical_formula_sum            'C10 H11 N O2'
_chemical_formula_weight         177.20
_chemical_name_common            'compound 1alpha'
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 99.548(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.0366(4)
_cell_length_b                   13.2899(5)
_cell_length_c                   6.3763(2)
_cell_measurement_temperature    100.0(10)
_cell_volume                     922.29(6)
_computing_data_collection       PRON2010
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.0(10)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.687
_diffrn_measurement_device_type  'closed Eulerian cradle HEiDi'
_diffrn_measurement_method       'rocking scan'
_diffrn_radiation_source         'FRM II'
_diffrn_radiation_type           neutrons
_diffrn_radiation_wavelength     0.793
_diffrn_reflns_av_R_equivalents  0.0967
_diffrn_reflns_av_unetI/netI     0.0965
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.687
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            1688
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.687
_diffrn_reflns_theta_full        28.411
_diffrn_reflns_theta_max         35.598
_diffrn_reflns_theta_min         2.699
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.001
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_description       prism
_exptl_crystal_F_000             18
_exptl_crystal_size_max          4.4
_exptl_crystal_size_mid          4.3
_exptl_crystal_size_min          3.3
_refine_diff_density_max         0.135
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       2.0(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     114
_refine_ls_number_reflns         1055
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.1260
_refine_ls_R_factor_gt           0.0815
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1000P)²+0.4000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1867
_refine_ls_wR_factor_ref         0.2208
_reflns_Friedel_coverage         0.000
_reflns_number_gt                718
_reflns_number_total             1055
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hw5050sup1.cif
_cod_data_source_block           100k
_cod_database_code               2108187
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_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_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.1125(4) 1.0523(3) 0.7871(6) 0.0261(8) Uani 1 1 d . . . . .
H1O H 1.018(3) 1.0743(10) 0.759(9) 0.037(6) Uani 0.5 1 d . U P . .
N1 N 1.000000 0.5766(2) 0.750000 0.0258(7) Uani 1 2 d S T P . .
C2 C 1.0367(3) 0.6292(2) 0.5918(5) 0.0252(7) Uani 1 1 d . . . . .
H2 H 1.0648(9) 0.5853(6) 0.4665(12) 0.049(2) Uani 1 1 d . . . . .
C3 C 1.0385(3) 0.7340(2) 0.5855(5) 0.0234(7) Uani 1 1 d . . . . .
H3 H 1.0708(8) 0.7727(5) 0.4548(11) 0.0443(18) Uani 1 1 d . . . . .
C4 C 1.000000 0.7890(3) 0.750000 0.0172(8) Uani 1 2 d S T P . .
C7 C 1.2345(3) 0.9042(3) 0.8345(6) 0.0304(8) Uani 1 1 d . . . . .
H7A H 1.232(2) 0.848(2) 0.953(4) 0.071(7) Uiso 0.53(4) 1 d . . P A 1
H7B H 1.2488(17) 0.8589(16) 0.693(3) 0.056(6) Uiso 0.53(4) 1 d . . P A 1
H7C H 1.306(2) 0.9568(19) 0.883(5) 0.066(6) Uiso 0.53(4) 1 d . . P A 1
H7D H 1.2380(18) 0.8294(16) 0.782(3) 0.051(6) Uiso 0.47(4) 1 d . . P A 2
H7E H 1.262(2) 0.8971(19) 1.006(4) 0.059(6) Uiso 0.47(4) 1 d . . P A 2
H7F H 1.3073(18) 0.9511(16) 0.789(4) 0.050(5) Uiso 0.47(4) 1 d . . P A 2
C8 C 1.1111(3) 0.9549(2) 0.7874(5) 0.0214(6) Uani 1 1 d . . . . .
C9 C 1.000000 0.9012(3) 0.750000 0.0206(8) Uani 1 2 d S T P . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0000 0.0000 '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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0000 0.0000 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C8 O1 H1O 105.3(9) . .
C2 N1 C2 117.3(3) 2_756 .
N1 C2 C3 123.3(3) . .
N1 C2 H2 115.8(5) . .
C3 C2 H2 120.9(5) . .
C2 C3 C4 119.5(3) . .
C2 C3 H3 120.1(5) . .
C4 C3 H3 120.4(5) . .
C3 C4 C3 117.1(4) 2_756 .
C3 C4 C9 121.45(18) 2_756 .
C3 C4 C9 121.45(18) . .
C8 C7 H7A 109.2(13) . .
C8 C7 H7B 108.9(10) . .
H7A C7 H7B 102.5(18) . .
C8 C7 H7C 111.6(13) . .
H7A C7 H7C 111(2) . .
H7B C7 H7C 113.1(18) . .
C8 C7 H7D 116.1(11) . .
C8 C7 H7E 109.1(12) . .
H7D C7 H7E 102.8(18) . .
C8 C7 H7F 111.9(11) . .
H7D C7 H7F 112.7(17) . .
H7E C7 H7F 102.9(17) . .
O1 C8 C9 121.2(3) . .
O1 C8 C7 116.0(3) . .
C9 C8 C7 122.8(3) . .
C8 C9 C8 118.9(4) . 2_756
C8 C9 C4 120.53(19) . .
C8 C9 C4 120.53(19) 2_756 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C8 1.294(5) .
O1 H1O 1.07(3) .
N1 C2 1.344(4) 2_756
N1 C2 1.344(4) .
C2 C3 1.393(4) .
C2 H2 1.076(7) .
C3 C4 1.401(4) .
C3 H3 1.088(7) .
C4 C9 1.491(6) .
C7 C8 1.504(5) .
C7 H7A 1.07(3) .
C7 H7B 1.12(2) .
C7 H7C 1.06(3) .
C7 H7D 1.05(2) .
C7 H7E 1.09(2) .
C7 H7F 1.09(2) .
C8 C9 1.404(4) .
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
_geom_hbond_site_symmetry_A
O1 H1O O1 1.07(3) 1.45(3) 2.450(8) 152.3(12) 2_756
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C2 N1 C2 C3 0.1(2) 2_756 .
N1 C2 C3 C4 -0.3(5) . .
C2 C3 C4 C3 0.1(2) . 2_756
C2 C3 C4 C9 -179.9(2) . .
O1 C8 C9 C8 -0.3(3) . 2_756
C7 C8 C9 C8 178.4(3) . 2_756
O1 C8 C9 C4 179.7(3) . .
C7 C8 C9 C4 -1.6(3) . .
C3 C4 C9 C8 108.8(2) 2_756 .
C3 C4 C9 C8 -71.2(2) . .
C3 C4 C9 C8 -71.2(2) 2_756 2_756
C3 C4 C9 C8 108.8(2) . 2_756

_cod_database_fobs_code 2108187
