#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/24/2202427.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_2202427
loop_
_publ_author_name
'Loguard S. Rojas'
'Belkis M. Ramírez'
'Asiloé J. Mora'
'Gerzon E. Delgado'
'Graciela Díaz de Delgado'
_publ_section_title
;
 Redetermination of potassium benzilate
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m647
_journal_page_last               m651
_journal_paper_doi               10.1107/S1600536803015915
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'K 1+, C14 H11 O3 1-'
_chemical_formula_moiety         'K 1+, C14 H11 O3 1-'
_chemical_formula_structural     'K 1+, C14 H11 O3 1-'
_chemical_formula_sum            'C14 H11 K O3'
_chemical_formula_weight         266.33
_chemical_name_common            'Potassium Benzilate'
_chemical_name_systematic
'Potassium α--Hydroxy--α--phenylbenzeneacetate'
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 111.4740(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.1283(15)
_cell_length_b                   9.0230(10)
_cell_length_c                   10.3639(11)
_cell_measurement_reflns_used    3427
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.54
_cell_measurement_theta_min      1.55
_cell_volume                     1229.5(2)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1998)'
_computing_publication_material
;
SHELXL97 and PLATON (Spek, 1990)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 0.70
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.919
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_sigmaI/netI    0.0364
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            15415
_diffrn_reflns_reduction_process SAINT
_diffrn_reflns_theta_full        26.5
_diffrn_reflns_theta_max         28.54
_diffrn_reflns_theta_min         1.55
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.428
_exptl_absorpt_correction_T_max  0.8796
_exptl_absorpt_correction_T_min  0.7572
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_meas      1.428
_exptl_crystal_density_method    'neutral buoyancy in CHCl~3~/C~4~H~10~O'
_exptl_crystal_description       plate
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.460
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2864
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0426
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0698P)²+0.0399P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1130
_refine_ls_wR_factor_ref         0.1195
_reflns_number_gt                2213
_reflns_number_total             2864
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cf6267.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_geom_bond_publ_flag' value 'Yes' changed to 'yes' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (24 times).

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_geom_bond_publ_flag' value 'Yes' changed to 'yes' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (24
times).

'_geom_angle_publ_flag' value 'Yes' changed to 'yes'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (27
times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2202427
_cod_database_fobs_code          2202427
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_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
K 0.03541(3) 0.03185(5) 0.81633(4) 0.04358(16) Uani d . 1 . . K
O1 -0.14873(10) 0.39938(15) 1.06378(13) 0.0367(3) Uani d . 1 . . O
H1 -0.1388(19) 0.329(3) 1.108(3) 0.058(7) Uiso d . 1 . . H
O2 -0.07919(10) 0.28955(14) 0.79362(12) 0.0382(3) Uani d . 1 . . O
O3 -0.07120(10) 0.15646(15) 0.97690(14) 0.0462(3) Uani d . 1 . . O
C1 -0.10511(13) 0.26085(17) 0.89388(17) 0.0300(4) Uani d . 1 . . C
C2 -0.18665(12) 0.36011(18) 0.91996(17) 0.0294(4) Uani d . 1 . . C
C3 -0.28622(13) 0.27359(19) 0.88436(18) 0.0347(4) Uani d . 1 . . C
C4 -0.30634(16) 0.1473(2) 0.8034(2) 0.0532(5) Uani d . 1 . . C
H4 -0.2586 0.1129 0.7682 0.064 Uiso calc R 1 . . H
C5 -0.3969(2) 0.0714(3) 0.7741(3) 0.0743(8) Uani d . 1 . . C
H5 -0.4096 -0.0132 0.7191 0.089 Uiso calc R 1 . . H
C6 -0.46796(18) 0.1198(4) 0.8253(3) 0.0751(8) Uani d . 1 . . C
H6 -0.5287 0.0682 0.8051 0.090 Uiso calc R 1 . . H
C7 -0.44947(17) 0.2439(3) 0.9061(3) 0.0657(7) Uani d . 1 . . C
H7 -0.4974 0.2762 0.9418 0.079 Uiso calc R 1 . . H
C8 -0.35905(15) 0.3222(2) 0.9352(2) 0.0486(5) Uani d . 1 . . C
H8 -0.3474 0.4076 0.9890 0.058 Uiso calc R 1 . . H
C9 -0.20387(12) 0.50445(18) 0.83704(17) 0.0301(4) Uani d . 1 . . C
C10 -0.15691(14) 0.6350(2) 0.8976(2) 0.0388(4) Uani d . 1 . . C
H10 -0.1150 0.6359 0.9908 0.047 Uiso calc R 1 . . H
C11 -0.17182(17) 0.7646(2) 0.8206(2) 0.0479(5) Uani d . 1 . . C
H11 -0.1405 0.8517 0.8630 0.057 Uiso calc R 1 . . H
C12 -0.23233(17) 0.7654(2) 0.6825(2) 0.0483(5) Uani d . 1 . . C
H12 -0.2423 0.8526 0.6315 0.058 Uiso calc R 1 . . H
C13 -0.27835(15) 0.6355(2) 0.6199(2) 0.0480(5) Uani d . 1 . . C
H13 -0.3185 0.6349 0.5260 0.058 Uiso calc R 1 . . H
C14 -0.26491(14) 0.5057(2) 0.69657(19) 0.0389(4) Uani d . 1 . . C
H14 -0.2969 0.4190 0.6539 0.047 Uiso calc R 1 . . H
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'
K K 0.2009 0.2494 '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
O3 K O2 3_557 2_546 79.14(4) ?
O3 K O2 3_557 . 122.55(4) ?
O2 K O2 2_546 . 150.761(19) ?
O3 K O3 3_557 . 76.40(4) ?
O2 K O3 2_546 . 146.61(4) ?
O2 K O3 . . 46.18(4) yes
O3 K O3 3_557 1 76.40(4) ?
O2 K O3 2_546 1 146.61(4) ?
O2 K O3 . 1 46.18(4) ?
O3 K O1 3_557 4_565 133.57(4) ?
O2 K O1 2_546 4_565 93.44(4) ?
O2 K O1 . 4_565 57.60(4) ?
O3 K O1 . 4_565 87.31(4) ?
O3 K O1 1 4_565 87.31(4) ?
C2 O1 K . 4_566 146.43(10) ?
C1 O2 K . 2_556 135.80(11) ?
C1 O2 K . . 95.43(10) ?
K O2 K 2_556 . 120.35(4) ?
C1 O3 K . 3_557 163.56(11) ?
C1 O3 K . . 92.68(10) ?
K O3 K 3_557 . 103.60(4) ?
O3 C1 O2 1 . 125.11(16) ?
O3 C1 O2 . . 125.11(16) yes
O3 C1 C2 1 . 115.85(14) ?
O3 C1 C2 . . 115.85(14) yes
O2 C1 C2 . . 119.05(14) yes
O1 C2 C9 1 . 107.22(13) yes
O1 C2 C9 . . 107.22(13) yes
O1 C2 C3 1 . 109.74(13) ?
O1 C2 C3 . . 109.74(13) yes
C9 C2 C3 . . 110.83(13) yes
O1 C2 C1 1 . 107.70(13) ?
O1 C2 C1 . . 107.70(13) yes
C9 C2 C1 . . 111.55(13) yes
C3 C2 C1 . . 109.71(13) yes
C4 C3 C8 . . 118.35(18) yes
C4 C3 C2 . . 122.24(16) yes
C8 C3 C2 . . 119.41(17) yes
C3 C4 C5 . . 120.6(2) yes
C6 C5 C4 . . 120.6(3) yes
C7 C6 C5 . . 119.8(2) yes
C6 C7 C8 . . 120.2(2) yes
C3 C8 C7 . . 120.4(2) yes
C10 C9 C14 . . 118.48(16) yes
C10 C9 C2 . . 121.22(15) yes
C14 C9 C2 . . 120.26(15) yes
C9 C10 C11 . . 120.63(17) yes
C12 C11 C10 . . 120.66(18) yes
C11 C12 C13 . . 119.43(18) yes
C12 C13 C14 . . 120.31(18) yes
C13 C14 C9 . . 120.48(18) yes
C2 O1 H1 . . 109.2(19) ?
K O1 H1 4_566 . 75.1(18) yes
C3 C4 H4 . . 119.7 ?
C5 C4 H4 . . 119.7 ?
C6 C5 H5 . . 119.7 ?
C4 C5 H5 . . 119.7 ?
C7 C6 H6 . . 120.1 ?
C5 C6 H6 . . 120.1 ?
C6 C7 H7 . . 119.9 ?
C8 C7 H7 . . 119.9 ?
C3 C8 H8 . . 119.8 ?
C7 C8 H8 . . 119.8 ?
C9 C10 H10 . . 119.7 ?
C11 C10 H10 . . 119.7 ?
C12 C11 H11 . . 119.7 ?
C10 C11 H11 . . 119.7 ?
C11 C12 H12 . . 120.3 ?
C13 C12 H12 . . 120.3 ?
C12 C13 H13 . . 119.8 ?
C14 C13 H13 . . 119.8 ?
C13 C14 H14 . . 119.8 ?
C9 C14 H14 . . 119.8 ?
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
K O2 . 2.7937(13) yes
K O3 . 2.8525(13) yes
K O1 4_565 3.0031(14) yes
K O3 3_557 2.6347(13) yes
K O2 2_546 2.6414(13) yes
O1 C2 . 1.432(2) yes
O2 C1 . 1.249(2) yes
O2 K 2_556 2.6414(13) ?
O3 C1 . 1.247(2) yes
O3 K 3_557 2.6347(13) ?
C1 C2 . 1.559(2) yes
C2 C9 . 1.530(2) yes
C2 C3 . 1.531(2) yes
C3 C4 . 1.382(3) yes
C3 C8 . 1.388(3) yes
C4 C5 . 1.384(3) yes
C5 C6 . 1.366(4) yes
C6 C7 . 1.365(4) yes
C7 C8 . 1.393(3) yes
C9 C10 . 1.385(2) yes
C9 C14 . 1.394(2) yes
C10 C11 . 1.387(3) yes
C11 C12 . 1.373(3) yes
C12 C13 . 1.382(3) yes
C13 C14 . 1.388(3) yes
O1 H1 . 0.77(2) yes
C4 H4 . 0.930 ?
C4 H4 . 0.930 ?
C5 H5 . 0.930 ?
C6 H6 . 0.930 ?
C7 H7 . 0.930 ?
C8 H8 . 0.930 ?
C10 H10 . 0.930 ?
C11 H11 . 0.930 ?
C12 H12 . 0.930 ?
C13 H13 . 0.930 ?
C13 H13 . 0.930 ?
C14 H14 . 0.930 ?
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
_geom_hbond_publ_flag
O1 H1 O2 4_566 0.77(2) 2.09(2) 2.7986(18) 154(2) yes
O1 H1 O3 1 0.77(2) 2.47(3) 2.7454(18) 103(2) yes
C10 H10 O1 1 0.93 2.37 2.712(2) 101 yes
