#------------------------------------------------------------------------------
#$Date: 2008-03-30 12:21:05 +0200 (Sun, 30 Mar 2008) $
#$Revision: 321 $
#$URL: svn://www.crystallography.net/cod/cif/2/2100616.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_2100616
loop_
_publ_author_name
'V. Bertolasi'
'L. Pretto'
'G. Gilli'
'P. Gilli'
_publ_section_title
;
\p-Bond cooperativity and anticooperativity effects in
resonance-assisted hydrogen bonds (RAHBs)
;
_journal_coeditor_code           DE5027
_journal_date_accepted           2006-06-01
_journal_date_recd_electronic    2006-02-08
_journal_issue                   4
_journal_name_full               'Acta Crystallographica, Section B'
_journal_page_first              850
_journal_page_last               863
_journal_paper_category          FA
_journal_volume                  62
_journal_year                    2006
_chemical_formula_moiety         'C16 H13 Cl O3'
_chemical_formula_sum            'C16 H13 Cl O3'
_chemical_formula_weight         288.71
_chemical_name_systematic
;
(2Z)-1-(2-hydroxy-4-methyl-5-chlorophenyl)-3-phenyl-1,3-propanedione enol
;
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 104.777(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.1470(10)
_cell_length_b                   5.3300(3)
_cell_length_c                   18.618(2)
_cell_measurement_reflns_used    5414
_cell_measurement_temperature    295
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.98
_cell_volume                     1357.4(2)
_computing_cell_refinement       'Denzo-SMN (Otwinowski & Minor (1997)'
_computing_data_collection       'Kappa CCD server software (1997)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor (1997)'
_computing_molecular_graphics    'ORTEP III (Burnett & Johnson, 1996)'
_computing_publication_material
;
SHELXL-97 (Sheldrick, 1997), PARST (Nardelli, 1995)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      295
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       '\f scans and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.049
_diffrn_reflns_av_sigmaI/netI    0.0706
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            5414
_diffrn_reflns_theta_full        27.52
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         2.98
_exptl_absorpt_coefficient_mu    0.285
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.420
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         3078
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.122
_refine_ls_R_factor_all          0.0836
_refine_ls_R_factor_gt           0.0554
_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/[\s^2^(Fo^2^)+(0.0652P)^2^+0.3211P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1327
_refine_ls_wR_factor_ref         0.1602
_reflns_number_gt                2210
_reflns_number_total             3078
_reflns_threshold_expression     I>2sigma(I)
_[local]_cod_data_source_file    de5027.cif
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
Cl Cl1 0.61718(5) 1.08215(13) -0.01326(4) 0.0684(3) Uani d 1
O O1 0.93055(14) 0.2348(3) -0.00791(10) 0.0619(5) Uani d 1
O O2 0.97198(16) -0.0121(4) 0.11356(12) 0.0701(6) Uani d 1
O O3 0.88526(17) 0.4733(4) -0.13311(11) 0.0742(6) Uani d 1
C C1 0.87488(17) 0.3740(4) 0.01827(13) 0.0496(5) Uani d 1
C C2 0.86620(18) 0.3339(5) 0.09237(13) 0.0525(6) Uani d 1
C C3 0.91447(17) 0.1488(4) 0.13671(13) 0.0478(5) Uani d 1
C C4 0.90833(17) 0.1060(4) 0.21409(13) 0.0477(5) Uani d 1
C C5 0.8559(2) 0.2670(5) 0.24816(14) 0.0583(6) Uani d 1
C C6 0.8546(2) 0.2320(6) 0.32156(15) 0.0651(7) Uani d 1
C C7 0.9040(2) 0.0365(5) 0.36132(16) 0.0657(7) Uani d 1
C C8 0.9540(3) -0.1277(6) 0.32795(17) 0.0714(8) Uani d 1
C C9 0.9570(2) -0.0946(5) 0.25450(16) 0.0630(7) Uani d 1
C C10 0.81909(17) 0.5727(4) -0.02872(12) 0.0469(5) Uani d 1
C C11 0.82638(19) 0.6124(4) -0.10230(13) 0.0533(6) Uani d 1
C C12 0.7710(2) 0.7987(5) -0.14550(14) 0.0601(7) Uani d 1
C C13 0.70543(18) 0.9469(4) -0.12148(13) 0.0511(5) Uani d 1
C C14 0.69912(17) 0.9060(4) -0.04817(12) 0.0470(5) Uani d 1
C C15 0.75375(17) 0.7275(4) -0.00388(13) 0.0490(5) Uani d 1
C C16 0.6451(3) 1.1397(6) -0.17072(18) 0.0655(7) Uani d 1
H H20 0.970(3) 0.029(8) 0.066(3) 0.116(14) Uiso d 1
H H30 0.918(3) 0.348(7) -0.097(2) 0.106(12) Uiso d 1
H H2 0.824(2) 0.447(5) 0.1082(17) 0.071(8) Uiso d 1
H H5 0.822(2) 0.412(5) 0.2217(16) 0.061(7) Uiso d 1
H H6 0.823(2) 0.355(5) 0.3434(16) 0.063(7) Uiso d 1
H H7 0.902(2) 0.006(6) 0.412(2) 0.087(9) Uiso d 1
H H8 0.989(3) -0.258(7) 0.353(2) 0.096(11) Uiso d 1
H H9 0.992(3) -0.193(7) 0.232(2) 0.096(11) Uiso d 1
H H12 0.775(2) 0.821(6) -0.1995(19) 0.083(9) Uiso d 1
H H15 0.7471(19) 0.709(5) 0.0439(15) 0.057(7) Uiso d 1
H H16A 0.662(3) 1.298(8) -0.159(2) 0.107(13) Uiso d 1
H H16B 0.639(3) 1.101(7) -0.224(2) 0.101(12) Uiso d 1
H H16C 0.580(4) 1.131(8) -0.174(3) 0.129(16) Uiso d 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
Cl1 0.0731(5) 0.0813(5) 0.0611(4) 0.0264(3) 0.0361(3) 0.0065(3)
O1 0.0718(11) 0.0657(10) 0.0576(10) 0.0195(8) 0.0338(9) 0.0007(8)
O2 0.0905(14) 0.0646(11) 0.0653(12) 0.0278(10) 0.0386(11) 0.0069(9)
O3 0.0953(15) 0.0863(13) 0.0574(11) 0.0309(11) 0.0496(11) 0.0083(10)
C1 0.0497(13) 0.0547(13) 0.0498(13) 0.0020(10) 0.0227(10) -0.0021(10)
C2 0.0570(14) 0.0581(13) 0.0481(13) 0.0102(11) 0.0240(11) 0.0011(10)
C3 0.0502(13) 0.0470(11) 0.0504(12) 0.0011(9) 0.0205(10) -0.0033(9)
C4 0.0504(13) 0.0441(11) 0.0504(12) -0.0019(9) 0.0162(10) 0.0015(9)
C5 0.0689(16) 0.0581(14) 0.0537(14) 0.0094(12) 0.0261(12) 0.0094(11)
C6 0.0801(18) 0.0679(16) 0.0570(15) 0.0047(14) 0.0351(14) 0.0067(12)
C7 0.0805(19) 0.0699(16) 0.0517(15) -0.0064(14) 0.0263(14) 0.0115(12)
C8 0.085(2) 0.0637(17) 0.0657(17) 0.0110(14) 0.0203(15) 0.0198(14)
C9 0.0760(18) 0.0542(14) 0.0621(16) 0.0096(12) 0.0236(14) 0.0061(12)
C10 0.0511(13) 0.0543(12) 0.0414(11) 0.0022(9) 0.0226(10) -0.0003(9)
C11 0.0606(14) 0.0607(14) 0.0480(13) 0.0060(11) 0.0310(11) 0.0006(10)
C12 0.0741(17) 0.0687(15) 0.0484(14) 0.0072(13) 0.0360(13) 0.0069(11)
C13 0.0561(14) 0.0549(13) 0.0472(12) -0.0010(10) 0.0220(11) 0.0055(10)
C14 0.0484(12) 0.0545(12) 0.0441(12) 0.0015(9) 0.0229(10) -0.0004(9)
C15 0.0530(13) 0.0590(13) 0.0419(12) 0.0023(10) 0.0247(10) 0.0012(10)
C16 0.076(2) 0.0671(18) 0.0581(17) 0.0100(14) 0.0259(15) 0.0143(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C14 1.741(2)
O1 C1 1.267(3)
O2 C3 1.327(3)
O2 H20 0.91(4)
O3 C11 1.348(3)
O3 H30 0.98(4)
C1 C2 1.432(3)
C1 C10 1.469(3)
C2 C3 1.354(3)
C2 H2 0.95(3)
C3 C4 1.483(3)
C4 C9 1.385(3)
C4 C5 1.389(3)
C5 C6 1.384(4)
C5 H5 0.97(3)
C6 C7 1.363(4)
C6 H6 0.94(3)
C7 C8 1.370(4)
C7 H7 0.97(4)
C8 C9 1.390(4)
C8 H8 0.90(4)
C9 H9 0.90(4)
C10 C15 1.402(3)
C10 C11 1.416(3)
C11 C12 1.387(4)
C12 C13 1.377(3)
C12 H12 1.03(3)
C13 C14 1.407(3)
C13 C16 1.492(4)
C14 C15 1.363(3)
C15 H15 0.92(3)
C16 H16A 0.89(4)
C16 H16B 0.99(4)
C16 H16C 0.91(5)
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C3 O2 H20 107(3)
C11 O3 H30 109(2)
O1 C1 C2 119.8(2)
O1 C1 C10 119.1(2)
C2 C1 C10 121.1(2)
C3 C2 C1 122.8(2)
C3 C2 H2 122.4(18)
C1 C2 H2 114.8(18)
O2 C3 C2 121.9(2)
O2 C3 C4 114.1(2)
C2 C3 C4 124.0(2)
C9 C4 C5 118.6(2)
C9 C4 C3 120.2(2)
C5 C4 C3 121.3(2)
C6 C5 C4 120.7(2)
C6 C5 H5 118.8(17)
C4 C5 H5 120.5(17)
C7 C6 C5 120.4(3)
C7 C6 H6 122.1(17)
C5 C6 H6 117.4(17)
C6 C7 C8 119.6(3)
C6 C7 H7 122(2)
C8 C7 H7 119(2)
C7 C8 C9 120.9(3)
C7 C8 H8 122(2)
C9 C8 H8 117(2)
C4 C9 C8 119.8(3)
C4 C9 H9 117(2)
C8 C9 H9 123(2)
C15 C10 C11 116.6(2)
C15 C10 C1 121.79(19)
C11 C10 C1 121.6(2)
O3 C11 C12 117.8(2)
O3 C11 C10 122.3(2)
C12 C11 C10 119.9(2)
C13 C12 C11 123.3(2)
C13 C12 H12 117.6(18)
C11 C12 H12 118.9(18)
C12 C13 C14 116.2(2)
C12 C13 C16 121.5(2)
C14 C13 C16 122.3(2)
C15 C14 C13 121.9(2)
C15 C14 Cl1 118.64(16)
C13 C14 Cl1 119.44(18)
C14 C15 C10 122.1(2)
C14 C15 H15 118.5(16)
C10 C15 H15 119.4(16)
C13 C16 H16A 115(3)
C13 C16 H16B 111(2)
H16A C16 H16B 114(3)
C13 C16 H16C 115(3)
H16A C16 H16C 106(4)
H16B C16 H16C 95(3)