#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/84/2238479.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_2238479
loop_
_publ_author_name
'Hachuła, Barbara'
'Polasz, Anna'
'Dzida, Marzena'
'Nowak, Maria'
'Kusz, Joachim'
_publ_section_title
;
 Levulinic acid
;
_journal_coeditor_code           FF2114
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1406
_journal_paper_doi               10.1107/S1600536813021090
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C5 H8 O3'
_chemical_formula_moiety         'C5 H8 O3'
_chemical_formula_sum            'C5 H8 O3'
_chemical_formula_weight         116.11
_chemical_melting_point_gt       303
_chemical_melting_point_lt       306
_chemical_name_common            'Levulinic acid'
_chemical_name_systematic
;
4-Oxopentanoic acid
;
_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                 99.112(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.8761(2)
_cell_length_b                   12.1025(4)
_cell_length_c                   9.8220(3)
_cell_measurement_reflns_used    6623
_cell_measurement_temperature    100.0(10)
_cell_measurement_theta_max      34.5069
_cell_measurement_theta_min      3.3704
_cell_volume                     572.31(4)
_computing_cell_refinement
;
CrysAlis RED (Oxford Diffraction, 2006)
;
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction, 2006)
;
_computing_data_reduction
;
CrysAlis RED (Oxford Diffraction, 2006)
;
_computing_molecular_graphics
;
Mercury (Macrae et al., 2006)
;
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0(10)
_diffrn_detector_area_resol_mean 16.0328
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur diffractometer with a Sapphire3 detector
;
_diffrn_measurement_method       'ω scan'
_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  0.0339
_diffrn_reflns_av_sigmaI/netI    0.0157
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7178
_diffrn_reflns_theta_full        25.06
_diffrn_reflns_theta_max         25.06
_diffrn_reflns_theta_min         3.37
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58528
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2006)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       polyhedron
_exptl_crystal_F_000             248
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.242
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     77
_refine_ls_number_reflns         1013
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0400
_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)+(0.0797P)²+0.1280P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1103
_refine_ls_wR_factor_ref         0.1136
_reflns_number_gt                902
_reflns_number_total             1013
_reflns_threshold_expression     I>2sigma(I)
_iucr_refine_instructions_details
;
TITL Flch13_hb8 in P21/c
CELL  0.71073   4.8761  12.1025   9.8220   90.000   99.112   90.000
ZERR     4.00   0.0002   0.0004   0.0003    0.000    0.003    0.000
LATT   1
SYMM  - X, 1/2 + Y, 1/2 - Z
SFAC  C    H    O
UNIT  20   32   12
MERG   2
shel 999 0.839
eqiv $1 x-1, -y+1/2, z+1/2
htab o1 o3_$1
FMAP   2
PLAN   10
SIZE     0.16   0.21   0.44
ACTA
MPLA 8 C1 C2 C3 C4 C5 O1 O2 O3
htab
BOND
BOND   $H
CONF
L.S.  10
TEMP  -173.00
WGHT    0.079700    0.128000
FVAR       6.31857
O1    3    0.419392    0.169881    1.051788    11.00000    0.02531    0.01865 =
         0.01370    0.00057    0.00926   -0.00115
O2    3    0.393035    0.353835    1.064488    11.00000    0.04347    0.02043 =
         0.02749   -0.00159    0.02305    0.00099
O3    3    1.058945    0.318395    0.733237    11.00000    0.02399    0.02176 =
         0.01483    0.00012    0.00722    0.00250
C1    1    0.483554    0.272384    1.016882    11.00000    0.01999    0.01874 =
         0.00881    0.00035    0.00202   -0.00024
C2    1    0.678237    0.273590    0.911774    11.00000    0.02021    0.01869 =
         0.01116   -0.00086    0.00502    0.00171
AFIX  23
H2A   2    0.593163    0.232253    0.828756    11.00000   -1.20000
H2B   2    0.853739    0.236084    0.950528    11.00000   -1.20000
AFIX   0
C3    1    0.741075    0.390980    0.871130    11.00000    0.02184    0.01833 =
         0.01183   -0.00149    0.00597   -0.00023
AFIX  23
H3A   2    0.564120    0.427638    0.832820    11.00000   -1.20000
H3B   2    0.822144    0.431895    0.955212    11.00000   -1.20000
AFIX   0
C4    1    0.936431    0.399499    0.767332    11.00000    0.01835    0.02066 =
         0.00917   -0.00155    0.00014   -0.00002
C5    1    0.972210    0.512134    0.708567    11.00000    0.03344    0.02242 =
         0.01945    0.00362    0.01248    0.00081
AFIX 137
H5A   2    1.139396    0.512965    0.664807    11.00000   -1.50000
H5B   2    0.990855    0.567099    0.782730    11.00000   -1.50000
H5C   2    0.809734    0.529866    0.639803    11.00000   -1.50000
AFIX   0
H1    2    0.310875    0.176555    1.107882    11.00000   -1.50000
HKLF 4
REM  Flch13_hb8 in P21/c
REM R1 =  0.0400 for    902 Fo > 4sig(Fo)  and  0.0447 for all   1013 data
REM     77 parameters refined using      0 restraints
END
WGHT      0.0792      0.1280
REM Highest difference peak  0.232,  deepest hole -0.242,  1-sigma level  0.057
Q1    1   0.7008  0.3352  0.8858  11.00000  0.05    0.23
Q2    1   0.6034  0.1338  1.0590  11.00000  0.05    0.23
Q3    1   1.2561  0.3234  0.7531  11.00000  0.05    0.21
Q4    1   0.5922  0.3633  1.0878  11.00000  0.05    0.21
Q5    1   0.8334  0.3992  0.8247  11.00000  0.05    0.20
Q6    1   0.9486  0.4588  0.7338  11.00000  0.05    0.19
Q7    1   0.7587  0.2111  0.9012  11.00000  0.05    0.18
Q8    1   0.8505  0.5788  0.7433  11.00000  0.05    0.18
Q9    1   0.5692  0.2732  0.9580  11.00000  0.05    0.18
Q10   1   0.2002  0.1659  1.0100  11.00000  0.05    0.18
;
_cod_data_source_file            ff2114.cif
_cod_data_source_block           I
_cod_original_cell_volume        572.31(3)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2238479
_cod_database_fobs_code          2238479
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
O O1 0.4194(2) 0.16988(8) 1.05179(10) 0.0186(3) Uani d . 1 1
O O2 0.3930(2) 0.35384(9) 1.06449(12) 0.0286(4) Uani d . 1 1
O O3 1.0589(2) 0.31839(8) 0.73324(10) 0.0197(3) Uani d . 1 1
C C1 0.4836(3) 0.27238(11) 1.01688(14) 0.0159(4) Uani d . 1 1
C C2 0.6782(3) 0.27359(12) 0.91177(14) 0.0164(4) Uani d . 1 1
H H2A 0.5932 0.2323 0.8288 0.020 Uiso calc R 1 1
H H2B 0.8537 0.2361 0.9505 0.020 Uiso calc R 1 1
C C3 0.7411(3) 0.39098(12) 0.87113(14) 0.0170(4) Uani d . 1 1
H H3A 0.5641 0.4276 0.8328 0.020 Uiso calc R 1 1
H H3B 0.8221 0.4319 0.9552 0.020 Uiso calc R 1 1
C C4 0.9364(3) 0.39950(11) 0.76733(13) 0.0163(4) Uani d . 1 1
C C5 0.9722(3) 0.51213(13) 0.70857(16) 0.0242(4) Uani d . 1 1
H H5A 1.1394 0.5130 0.6648 0.036 Uiso calc R 1 1
H H5B 0.9909 0.5671 0.7827 0.036 Uiso calc R 1 1
H H5C 0.8097 0.5299 0.6398 0.036 Uiso calc R 1 1
H H1 0.311(4) 0.1766(16) 1.108(2) 0.036 Uiso d . 1 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
O1 0.0253(6) 0.0186(6) 0.0137(5) -0.0011(4) 0.0093(4) 0.0006(4)
O2 0.0435(7) 0.0204(6) 0.0275(7) 0.0010(5) 0.0231(5) -0.0016(5)
O3 0.0240(6) 0.0218(6) 0.0148(5) 0.0025(4) 0.0072(4) 0.0001(4)
C1 0.0200(7) 0.0187(7) 0.0088(7) -0.0002(6) 0.0020(5) 0.0003(5)
C2 0.0202(7) 0.0187(8) 0.0112(7) 0.0017(5) 0.0050(5) -0.0009(5)
C3 0.0218(7) 0.0183(8) 0.0118(7) -0.0002(5) 0.0060(6) -0.0015(5)
C4 0.0183(7) 0.0207(8) 0.0092(7) 0.0000(5) 0.0001(5) -0.0016(6)
C5 0.0334(8) 0.0224(8) 0.0195(8) 0.0008(6) 0.0125(6) 0.0036(6)
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'
O O 0.0106 0.0060 '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 106.3(14)
O2 C1 O1 123.01(13)
O2 C1 C2 124.51(13)
O1 C1 C2 112.48(12)
C1 C2 C3 111.32(12)
C1 C2 H2A 109.4
C3 C2 H2A 109.4
C1 C2 H2B 109.4
C3 C2 H2B 109.4
H2A C2 H2B 108.0
C4 C3 C2 114.68(12)
C4 C3 H3A 108.6
C2 C3 H3A 108.6
C4 C3 H3B 108.6
C2 C3 H3B 108.6
H3A C3 H3B 107.6
O3 C4 C5 122.14(13)
O3 C4 C3 121.30(12)
C5 C4 C3 116.57(12)
C4 C5 H5A 109.5
C4 C5 H5B 109.5
H5A C5 H5B 109.5
C4 C5 H5C 109.5
H5A C5 H5C 109.5
H5B C5 H5C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.3373(17)
O1 H1 0.83(2)
O2 C1 1.2044(17)
O3 C4 1.2231(17)
C1 C2 1.5092(19)
C2 C3 1.520(2)
C2 H2A 0.9900
C2 H2B 0.9900
C3 C4 1.5050(19)
C3 H3A 0.9900
C3 H3B 0.9900
C4 C5 1.501(2)
C5 H5A 0.9800
C5 H5B 0.9800
C5 H5C 0.9800
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 O3 4_466 0.83(2) 1.87(2) 2.6977(13) 176(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
O2 C1 C2 C3 -1.2(2)
O1 C1 C2 C3 178.42(10)
C1 C2 C3 C4 179.46(11)
C2 C3 C4 O3 -8.66(18)
C2 C3 C4 C5 171.36(11)
