#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/67/2016730.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_2016730
loop_
_publ_author_name
'Bakowicz, Julia'
'Turowska-Tyrk, Ilona'
_publ_section_title
;
 rac-3-Benzoyl-2-methylpropionic acid and its organic salts:
 possibilities of Yang photocyclization in crystals
;
_journal_coeditor_code           SK3242
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o437
_journal_page_last               o440
_journal_paper_doi               10.1107/S0108270108021380
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C5 H6 N + , H+ , 2C11 H11 O3 -'
_chemical_formula_moiety         'C5 H6 N + , H+ , 2C11 H11 O3 -'
_chemical_formula_sum            'C27 H29 N O6'
_chemical_formula_weight         463.51
_chemical_name_systematic
;
pyridinium [hydrogen bis(rac-3-benzoyl-2-methylpropionate)]
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.34(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   25.759(6)
_cell_length_b                   10.172(2)
_cell_length_c                   9.776(2)
_cell_measurement_reflns_used    1115
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      18.93
_cell_measurement_theta_min      2.95
_cell_volume                     2545.8(9)
_computing_cell_refinement       'CrysAlisCCD (Oxford Diffraction, 2003)'
_computing_data_collection       'CrysAlisCCD (Oxford Diffraction, 2003)'
_computing_data_reduction        'CrysAlisRED (Oxford Diffraction, 2003)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      299(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Kuma KM4 CCD'
_diffrn_measurement_method       ω
_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  0.0401
_diffrn_reflns_av_sigmaI/netI    0.0350
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6670
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.61
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.209
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.205
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2199
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.145
_refine_ls_R_factor_all          0.0850
_refine_ls_R_factor_gt           0.0628
_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)+(0.1206P)²+0.2239P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1920
_refine_ls_wR_factor_ref         0.2103
_reflns_number_gt                1454
_reflns_number_total             2199
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sk3242.cif
_cod_data_source_block           III
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2016730
_cod_database_fobs_code          2016730
loop_
_symmetry_equiv_pos_as_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_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
C C1 0.06840(9) 0.4104(2) 0.1105(3) 0.0666(7) Uani d . 1
C C2 0.10296(9) 0.4036(3) 0.2455(3) 0.0678(7) Uani d . 1
H H2 0.1011 0.4883 0.2925 0.081 Uiso calc R 1
C C3 0.08289(12) 0.2977(3) 0.3353(3) 0.0901(9) Uani d . 1
H H3A 0.1049 0.2933 0.4212 0.135 Uiso calc R 1
H H3B 0.0833 0.2144 0.2893 0.135 Uiso calc R 1
H H3C 0.0478 0.3184 0.3525 0.135 Uiso calc R 1
C C4 0.15940(9) 0.3771(3) 0.2249(3) 0.0703(7) Uani d . 1
H H4A 0.1787 0.3609 0.3142 0.084 Uiso calc R 1
H H4B 0.1609 0.2975 0.1709 0.084 Uiso calc R 1
C C5 0.18602(10) 0.4843(3) 0.1557(3) 0.0704(7) Uani d . 1
C C6 0.23955(9) 0.4621(3) 0.1171(2) 0.0667(7) Uani d . 1
C C7 0.26233(11) 0.5590(3) 0.0451(3) 0.0890(9) Uani d . 1
H H7 0.2446 0.6375 0.0248 0.107 Uiso calc R 1
C C8 0.31145(13) 0.5401(4) 0.0029(3) 0.1031(11) Uani d . 1
H H8 0.3265 0.6058 -0.0458 0.124 Uiso calc R 1
C C9 0.33768(12) 0.4251(4) 0.0327(3) 0.1006(10) Uani d . 1
H H9 0.3704 0.4124 0.0032 0.121 Uiso calc R 1
C C10 0.31636(11) 0.3299(3) 0.1048(3) 0.0877(9) Uani d . 1
H H10 0.3347 0.2524 0.1260 0.105 Uiso calc R 1
C C11 0.26728(10) 0.3474(3) 0.1471(3) 0.0779(8) Uani d . 1
H H11 0.2528 0.2811 0.1962 0.093 Uiso calc R 1
O O1 0.03023(7) 0.49029(17) 0.10689(17) 0.0788(6) Uani d . 1
H HO1 0.0000 0.5000 0.0000 0.18(2) Uiso d S 1
O O2 0.07553(8) 0.3375(2) 0.01525(19) 0.1040(8) Uani d . 1
O O3 0.16416(8) 0.5889(2) 0.1291(3) 0.1052(8) Uani d . 1
N N1 0.0000 0.7117(3) 0.2500 0.0989(12) Uani d SD 1
H H1 0.0000 0.6271 0.2500 0.119 Uiso calc SR 1
C C12 0.04013(11) 0.7802(3) 0.2005(4) 0.1218(14) Uani d D 1
H H12 0.0676 0.7340 0.1691 0.146 Uiso calc R 1
C C13 0.04039(15) 0.9176(3) 0.1963(5) 0.153(2) Uani d D 1
H H13 0.0670 0.9617 0.1584 0.184 Uiso calc R 1
C C14 0.0000 0.9898(4) 0.2500 0.1227(19) Uani d SD 1
H H14 0.0000 1.0812 0.2500 0.147 Uiso calc SR 1
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'
N N 0.0061 0.0033 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
O2 C1 O1 . . 123.2(2)
O2 C1 C2 . . 121.0(2)
O1 C1 C2 . . 115.7(2)
C1 C2 C4 . . 112.0(2)
C1 C2 C3 . . 109.5(2)
C4 C2 C3 . . 110.1(2)
C1 C2 H2 . . 108.4
C4 C2 H2 . . 108.4
C3 C2 H2 . . 108.4
C2 C3 H3A . . 109.5
C2 C3 H3B . . 109.5
H3A C3 H3B . . 109.5
C2 C3 H3C . . 109.5
H3A C3 H3C . . 109.5
H3B C3 H3C . . 109.5
C5 C4 C2 . . 115.3(2)
C5 C4 H4A . . 108.5
C2 C4 H4A . . 108.5
C5 C4 H4B . . 108.5
C2 C4 H4B . . 108.5
H4A C4 H4B . . 107.5
O3 C5 C6 . . 119.9(2)
O3 C5 C4 . . 120.7(2)
C6 C5 C4 . . 119.4(2)
C7 C6 C11 . . 118.2(2)
C7 C6 C5 . . 118.7(2)
C11 C6 C5 . . 123.2(2)
C6 C7 C8 . . 120.4(3)
C6 C7 H7 . . 119.8
C8 C7 H7 . . 119.8
C9 C8 C7 . . 120.1(3)
C9 C8 H8 . . 120.0
C7 C8 H8 . . 120.0
C10 C9 C8 . . 120.4(3)
C10 C9 H9 . . 119.8
C8 C9 H9 . . 119.8
C9 C10 C11 . . 120.1(3)
C9 C10 H10 . . 120.0
C11 C10 H10 . . 120.0
C6 C11 C10 . . 120.9(3)
C6 C11 H11 . . 119.6
C10 C11 H11 . . 119.6
C1 O1 HO1 . . 119
C12 N1 C12 . 6_556 119.2(3)
C12 N1 H1 . . 120.4
C12 N1 H1 6_556 . 120.4
N1 C12 C13 . . 121.5(2)
N1 C12 H12 . . 119.3
C13 C12 H12 . . 119.3
C12 C13 C14 . . 120.0(3)
C12 C13 H13 . . 120.0
C14 C13 H13 . . 120.0
C13 C14 C13 6_556 . 117.8(3)
C13 C14 H14 6_556 . 121.1
C13 C14 H14 . . 121.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 O2 . 1.220(3)
C1 O1 . 1.273(3)
C1 C2 . 1.509(4)
C2 C4 . 1.514(3)
C2 C3 . 1.517(4)
C2 H2 . 0.9800
C3 H3A . 0.9600
C3 H3B . 0.9600
C3 H3C . 0.9600
C4 C5 . 1.490(4)
C4 H4A . 0.9700
C4 H4B . 0.9700
C5 O3 . 1.219(3)
C5 C6 . 1.486(4)
C6 C7 . 1.380(4)
C6 C11 . 1.382(4)
C7 C8 . 1.387(4)
C7 H7 . 0.9300
C8 C9 . 1.366(4)
C8 H8 . 0.9300
C9 C10 . 1.349(4)
C9 H9 . 0.9300
C10 C11 . 1.384(4)
C10 H10 . 0.9300
C11 H11 . 0.9300
O1 HO1 . 1.24
N1 C12 . 1.378(3)
N1 C12 6_556 1.378(3)
N1 H1 . 0.8600
C12 C13 . 1.399(3)
C12 H12 . 0.9300
C13 C14 . 1.420(3)
C13 H13 . 0.9300
C14 C13 6_556 1.420(3)
C14 H14 . 0.9300
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_1
_geom_torsion_site_symmetry_4
_geom_torsion
O2 C1 C2 C4 . . 37.5(3)
O1 C1 C2 C4 . . -146.6(2)
O2 C1 C2 C3 . . -84.9(3)
O1 C1 C2 C3 . . 90.9(3)
C1 C2 C4 C5 . . 66.5(3)
C3 C2 C4 C5 . . -171.4(2)
C2 C4 C5 O3 . . 5.7(4)
C2 C4 C5 C6 . . -173.4(2)
O3 C5 C6 C7 . . -3.3(4)
C4 C5 C6 C7 . . 175.8(2)
O3 C5 C6 C11 . . 178.3(3)
C4 C5 C6 C11 . . -2.6(4)
C11 C6 C7 C8 . . 0.8(4)
C5 C6 C7 C8 . . -177.6(3)
C6 C7 C8 C9 . . -0.1(5)
C7 C8 C9 C10 . . -0.8(5)
C8 C9 C10 C11 . . 1.0(5)
C7 C6 C11 C10 . . -0.6(4)
C5 C6 C11 C10 . . 177.8(2)
C9 C10 C11 C6 . . -0.3(4)
C12 N1 C12 C13 6_556 . -1.6(4)
N1 C12 C13 C14 . . 3.1(7)
C12 C13 C14 C13 . 6_556 -1.5(4)
