#------------------------------------------------------------------------------
#$Date: 2017-09-28 10:21:31 +0200 (jue 28 de sep de 2017) $
#$Revision: 201404 $
#$URL: svn://www.crystallography.net/cod/cif/2/31/01/2310129.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_2310129
loop_
_publ_author_name
'Nassour, Ayoub'
'Kubicki, Maciej'
'Wright, Jonathan'
'Borowiak, Teresa'
'Dutkiewicz, Grzegorz'
'Lecomte, Claude'
'Jelsch, Christian'
_publ_section_title
;
 Charge-density analysis using multipolar atom and spherical charge
 models: 2-methyl-1,3-cyclopentanedione, a compound displaying a
 resonance-assisted hydrogen bond.
;
_journal_coden_ASTM              ACSBDA
_journal_coeditor_code           PI5017
_journal_issue                   2
_journal_name_full
;
 Acta Crystallographica, Section B: Structural Science, Crystal
 Engineering and Materials
;
_journal_page_first              197
_journal_page_last               211
_journal_paper_doi               10.1107/S2052520613031375
_journal_volume                  70
_journal_year                    2014
_chemical_formula_moiety         'C6 H8 O2'
_chemical_formula_sum            'C6 H8 O2'
_chemical_formula_weight         112.128
_chemical_name_common            2-methyl-1,3-cyclopentanedione
_chemical_name_systematic        2-methyl-1,3-cyclopentanedione
_space_group_IT_number           12
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2y'
_symmetry_space_group_name_H-M   'C 1 2/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           MoPro12
_cell_angle_alpha                90.00
_cell_angle_beta                 93.69(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.402(3)
_cell_length_b                   6.470(2)
_cell_length_c                   6.321(2)
_cell_measurement_temperature    100
_cell_volume                     506.2(3)
_computing_molecular_graphics    MoproViewer
_computing_structure_refinement  'MoPro (J. Appl. Cryst. 2005, 38, 38-54)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'Huber, ID11/ESRF'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.21784
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_av_sigmaI/netI    0.00714
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            258713
_diffrn_reflns_theta_full        19.02
_diffrn_reflns_theta_max         19.29
_diffrn_reflns_theta_min         0.99
_exptl_absorpt_coefficient_mu    0.001
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             240
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.55
_refine_diff_density_min         -0.36
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         7434
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      1.330
_refine_ls_R_factor_all          0.0346
_refine_ls_R_factor_gt           0.0341
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'calc w =1/[93.*σ²(Fo²)]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0303
_refine_ls_wR_factor_ref         0.0307
_reflns_number_gt                7319
_reflns_number_total             7435
_reflns_threshold_expression     >2.0sigma(I)
_iucr_refine_instructions_details
;
;
_cod_data_source_file            pi5017sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     -c_2y
_cod_original_sg_symbol_H-M      C2/m
_cod_database_code               2310129
_cod_database_fobs_code          2310129
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'-x, -y, -z'
'x, -y, z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'
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_occupancy
_atom_site_symmetry_multiplicity
O O1 0.30499(2) 0. 1.06772(3) 0.0162(2) Uani d 1 2
O O3 0.178900(10) 0. 0.36827(2) 0.0129(2) Uani d 1 2
C C1 0.302450(10) 0. 0.87585(2) 0.0109(2) Uani d 1 2
C C2 0.2102210(10) 0. 0.73478(2) 0.0100(2) Uani d 1 2
C C3 0.2433330(10) 0. 0.53737(2) 0.0095(2) Uani d 1 2
C C4 0.3615180(10) 0. 0.52858(2) 0.0110(2) Uani d 1 2
C C5 0.401380(10) 0. 0.75687(2) 0.0144(2) Uani d 1 2
C C21 0.100080(10) 0. 0.80244(2) 0.0142(2) Uani d 1 2
H H3 0.22210 0. 0.23608 0.02464 Uani d 1 2
H H4 0.38786 0.13621 0.44339 0.02701 Uani d 1 1
H H5 0.45004 0.13600 0.79766 0.03256 Uani d 1 1
H H21A 0.04227 0. 0.67142 0.03257 Uani d 1 2
H H21B 0.08455 0.13300 0.89305 0.03115 Uani 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 0.0156(6) 0.0253(6) 0.0078(6) 0. 0.00156(5) 0.
O3 0.0117(6) 0.0178(6) 0.0091(6) 0. -0.000006(4) 0.
C1 0.0109(6) 0.0143(6) 0.0077(6) 0. 0.00152(4) 0.
C2 0.0094(6) 0.0122(6) 0.0085(6) 0. 0.00215(4) 0.
C3 0.0096(6) 0.0111(6) 0.0080(6) 0. 0.00136(4) 0.
C4 0.0101(6) 0.0140(6) 0.0091(6) 0. 0.00234(4) 0.
C5 0.0099(6) 0.0235(6) 0.0099(6) 0. 0.00083(4) 0.
C21 0.0108(6) 0.0180(6) 0.0142(6) 0. 0.00403(5) 0.
H3 0.0230 0.0353 0.0158 0. 0.0024 0.
H4 0.0263 0.0262 0.0291 -0.0049 0.0058 0.0074
H5 0.0295 0.0412 0.0265 -0.0138 -0.0023 -0.0041
H21A 0.0217 0.0492 0.0262 0. -0.0030 0.
H21B 0.0339 0.0293 0.0314 0.0036 0.0117 -0.0056
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C -0.0015 0.0001 'Su & Coppens. Acta. Cryst. (1997) A53, 749-762. '
H H 0.0000 0.0000 'Su & Coppens. Acta. Cryst. (1997) A53, 749-762. '
O O -0.0023 0.0004 'Su & Coppens. Acta. Cryst. (1997) A53, 749-762. '
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 C1 C2 127.12(6)
O1 C1 C5 122.68(5)
O3 C3 C2 124.09(3)
O3 C3 C4 122.23(4)
C1 C2 C3 107.80(4)
C1 C2 C21 123.65(3)
C1 C5 C4 104.90(4)
C1 C5 H5 110.2
C2 C3 C4 113.68(2)
C2 C1 C5 110.21(4)
C2 C21 H21B 111.4
C2 C21 H21A 111.7
C3 O3 H3 110.3
C3 C2 C21 128.55(4)
C3 C4 C5 103.42(4)
C3 C4 H4 110.4
C4 C5 H5 111.9
C5 C4 H4 112.6
H21A C21 H21B 106.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.2112(4)
O3 C3 1.2927(4)
O3 H3 1.021
C1 C2 1.4043(4)
C1 C5 1.4798(4)
C2 C3 1.3385(4)
C2 C21 1.4574(4)
C3 C4 1.4704(4)
C4 C5 1.4950(5)
C4 H4 1.094
C5 H5 1.088
C21 H21B 1.058
C21 H21A 1.060
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
O3 H3 O1 1_554 1.021 1.526 2.5370(6) 169.4
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 180.
O1 C1 C2 C21 0.
O1 C1 C5 C4 180.
O1 C1 C5 H5 -59.4
O3 C3 C2 C1 180.
O3 C3 C2 C21 0.
O3 C3 C4 C5 180.
O3 C3 C4 H4 59.3
C1 C2 C3 C4 0.
C1 C2 C21 H21B 60.9
C1 C2 C21 H21A 180.
C1 C5 C4 C3 0.
C1 C5 C4 H4 119.2
C2 C3 O3 H3 180.
C2 C3 C4 C5 0.
C2 C3 C4 H4 -120.7
C2 C1 C5 C4 0.
C2 C1 C5 H5 120.6
C3 C2 C1 C5 0.
C3 C2 C21 H21B -119.1
C3 C2 C21 H21A 0.
C3 C4 C5 H5 -119.4
C4 C3 O3 H3 0.
C4 C3 C2 C21 180.
C5 C1 C2 C21 180.
H4 C4 C5 H5 -0.2
