#------------------------------------------------------------------------------
#$Date: 2016-03-25 14:55:39 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179906 $
#$URL: svn://www.crystallography.net/cod/cif/7/02/02/7020253.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7020253
loop_
_publ_author_name
'Lombardo, Giuseppe M.'
'Portalone, Gustavo'
'Chiacchio, Ugo'
'Rescifina, Antonio'
'Punzo, Francesco'
_publ_section_title
;
 Potassium caffeate/caffeic acid co-crystal: the rat race between the
 catecholic and carboxylic moieties in an atypical co-crystal.
;
_journal_issue                   47
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              14337
_journal_page_last               14344
_journal_paper_doi               10.1039/c2dt31092a
_journal_volume                  41
_journal_year                    2012
_chemical_formula_moiety         'C18 H15 K O8, H2 O'
_chemical_formula_sum            'C18 H17 K O9'
_chemical_formula_weight         416.42
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                114.473(8)
_cell_angle_beta                 108.182(7)
_cell_angle_gamma                95.313(7)
_cell_formula_units_Z            2
_cell_length_a                   9.7482(7)
_cell_length_b                   10.2754(9)
_cell_length_c                   10.5529(9)
_cell_measurement_reflns_used    3521
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.8089
_cell_measurement_theta_min      3.0259
_cell_volume                     883.45(16)
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2006)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2006)'
_computing_data_reduction        'CrysAlis RED '
_computing_molecular_graphics    'WinGX (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 16.0696
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur S CCD'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_sigmaI/netI    0.0451
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6402
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         3.05
_exptl_absorpt_coefficient_mu    0.353
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86268
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tablets
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3084
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0751
_refine_ls_R_factor_gt           0.0508
_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)+(0.0657P)²+0.2078P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1121
_refine_ls_wR_factor_ref         0.1209
_reflns_number_gt                2348
_reflns_number_total             3084
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c2dt31092a.txt
_cod_data_source_block           kcaff3
_cod_database_code               7020253
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
K1 K 0.20164(7) -0.16093(7) 0.17274(8) 0.0405(2) Uani 1 1 d .
O1 O 0.5352(2) -1.0548(2) -0.3280(2) 0.0470(6) Uani 1 1 d .
O2 O 0.3569(2) -1.1957(2) -0.5550(2) 0.0417(6) Uani 1 1 d .
H21 H 0.419(5) -1.249(5) -0.571(5) 0.088(15) Uiso 1 1 d .
O3 O 0.3124(2) -0.3961(2) 0.0920(2) 0.0397(6) Uani 1 1 d .
H31 H 0.380(4) -0.408(4) 0.153(4) 0.054(11) Uiso 1 1 d .
O4 O 0.0458(2) -0.4182(2) -0.0887(2) 0.0332(5) Uani 1 1 d .
H4 H -0.038(4) -0.430(4) -0.151(4) 0.050(11) Uiso 1 1 d .
C1 C 0.4120(3) -1.0789(3) -0.4192(3) 0.0278(7) Uani 1 1 d .
C2 C 0.3067(3) -0.9855(3) -0.3979(3) 0.0320(7) Uani 1 1 d .
H2 H 0.2153 -1.0113 -0.4766 0.038 Uiso 1 1 calc R
C3 C 0.3404(3) -0.8662(3) -0.2691(3) 0.0315(7) Uani 1 1 d .
H3 H 0.4313 -0.8485 -0.1933 0.038 Uiso 1 1 calc R
C4 C 0.2536(3) -0.7567(3) -0.2286(3) 0.0279(6) Uani 1 1 d .
C5 C 0.3202(3) -0.6324(3) -0.0871(3) 0.0289(6) Uani 1 1 d .
H5 H 0.4143 -0.6237 -0.0216 0.035 Uiso 1 1 calc R
C6 C 0.2484(3) -0.5221(3) -0.0428(3) 0.0251(6) Uani 1 1 d .
C7 C 0.1067(3) -0.5340(3) -0.1399(3) 0.0247(6) Uani 1 1 d .
C8 C 0.0390(3) -0.6577(3) -0.2785(3) 0.0296(7) Uani 1 1 d .
H8 H -0.0561 -0.6674 -0.3429 0.035 Uiso 1 1 calc R
C9 C 0.1125(3) -0.7688(3) -0.3231(3) 0.0315(7) Uani 1 1 d .
H9 H 0.0659 -0.8518 -0.4172 0.038 Uiso 1 1 calc R
O1A O -0.2891(2) 0.6497(2) 0.5103(2) 0.0357(5) Uani 1 1 d .
O2A O -0.5146(2) 0.5923(2) 0.3354(2) 0.0326(5) Uani 1 1 d .
O3A O 0.1114(2) 0.0788(2) 0.2986(2) 0.0384(6) Uani 1 1 d .
H3A1 H 0.171(4) 0.159(4) 0.366(4) 0.054(11) Uiso 1 1 d .
O4A O -0.0734(2) -0.1348(2) 0.0351(2) 0.0302(5) Uani 1 1 d .
H4A H -0.132(3) -0.190(3) -0.042(3) 0.031(9) Uiso 1 1 d .
C1A C -0.3922(3) 0.5628(3) 0.3873(3) 0.0232(6) Uani 1 1 d .
C2A C -0.3749(3) 0.4159(3) 0.2944(3) 0.0327(7) Uani 1 1 d .
H2A H -0.4563 0.3488 0.2079 0.039 Uiso 1 1 calc R
C3A C -0.2497(3) 0.3761(3) 0.3286(3) 0.0285(6) Uani 1 1 d .
H3A H -0.1732 0.4450 0.4188 0.034 Uiso 1 1 calc R
C4A C -0.2129(3) 0.2386(3) 0.2451(3) 0.0268(6) Uani 1 1 d .
C5A C -0.0718(3) 0.2222(3) 0.3095(3) 0.0277(6) Uani 1 1 d .
H5A H -0.0063 0.2974 0.4033 0.033 Uiso 1 1 calc R
C6A C -0.0258(3) 0.0983(3) 0.2391(3) 0.0254(6) Uani 1 1 d .
C7A C -0.1252(3) -0.0154(3) 0.0983(3) 0.0238(6) Uani 1 1 d .
C8A C -0.2645(3) 0.0000(3) 0.0323(3) 0.0283(6) Uani 1 1 d .
H8A H -0.3298 -0.0744 -0.0620 0.034 Uiso 1 1 calc R
C9A C -0.3084(3) 0.1255(3) 0.1051(3) 0.0305(7) Uani 1 1 d .
H9A H -0.4032 0.1339 0.0594 0.037 Uiso 1 1 calc R
O5 O -0.2198(3) -0.3844(3) -0.2370(3) 0.0376(6) Uani 1 1 d .
H51 H -0.288(4) -0.438(4) -0.254(4) 0.061(14) Uiso 1 1 d .
H52 H -0.235(4) -0.377(4) -0.321(5) 0.069(14) Uiso 1 1 d .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O3A K1 O3 170.60(8) . .
O3A K1 O4A 58.47(6) . .
O3 K1 O4A 128.59(6) . .
O3A K1 O1 78.31(6) . 2_645
O3 K1 O1 98.51(7) . 2_645
O4A K1 O1 127.12(7) . 2_645
O3A K1 O4 128.97(7) . .
O3 K1 O4 58.09(6) . .
O4A K1 O4 70.62(6) . .
O1 K1 O4 143.46(7) 2_645 .
O3A K1 O2 99.76(7) . 1_566
O3 K1 O2 70.84(7) . 1_566
O4A K1 O2 136.58(7) . 1_566
O1 K1 O2 75.08(7) 2_645 1_566
O4 K1 O2 115.79(6) . 1_566
O3A K1 C8A 82.91(7) . 2
O3 K1 C8A 104.23(7) . 2
O4A K1 C8A 77.16(7) . 2
O1 K1 C8A 68.04(7) 2_645 2
O4 K1 C8A 89.56(7) . 2
O2 K1 C8A 141.70(7) 1_566 2
C1 O1 K1 138.3(2) . 2_645
C1 O2 K1 119.94(18) . 1_544
C1 O2 H21 113(3) . .
K1 O2 H21 110(3) 1_544 .
C6 O3 K1 125.19(17) . .
C6 O3 H31 111(3) . .
K1 O3 H31 123(3) . .
C7 O4 K1 122.65(16) . .
C7 O4 H4 112(2) . .
K1 O4 H4 125(2) . .
O1 C1 O2 122.2(3) . .
O1 C1 C2 125.9(2) . .
O2 C1 C2 111.9(2) . .
C3 C2 C1 120.7(3) . .
C3 C2 H2 119.6 . .
C1 C2 H2 119.6 . .
C2 C3 C4 128.6(3) . .
C2 C3 H3 115.7 . .
C4 C3 H3 115.7 . .
C9 C4 C5 118.6(2) . .
C9 C4 C3 124.0(2) . .
C5 C4 C3 117.3(2) . .
C6 C5 C4 120.9(3) . .
C6 C5 H5 119.5 . .
C4 C5 H5 119.5 . .
O3 C6 C5 122.7(2) . .
O3 C6 C7 117.1(2) . .
C5 C6 C7 120.2(2) . .
O4 C7 C8 124.5(2) . .
O4 C7 C6 116.2(2) . .
C8 C7 C6 119.3(2) . .
C7 C8 C9 120.3(3) . .
C7 C8 H8 119.8 . .
C9 C8 H8 119.8 . .
C4 C9 C8 120.7(2) . .
C4 C9 H9 119.7 . .
C8 C9 H9 119.7 . .
C6A O3A K1 125.01(16) . .
C6A O3A H3A1 111(2) . .
K1 O3A H3A1 122(2) . .
C7A O4A K1 123.15(16) . .
C7A O4A H4A 110(2) . .
K1 O4A H4A 127(2) . .
O1A C1A O2A 123.5(2) . .
O1A C1A C2A 119.6(2) . .
O2A C1A C2A 116.9(2) . .
C3A C2A C1A 123.1(3) . .
C3A C2A H2A 118.5 . .
C1A C2A H2A 118.5 . .
C2A C3A C4A 129.5(3) . .
C2A C3A H3A 115.2 . .
C4A C3A H3A 115.2 . .
C9A C4A C5A 117.9(2) . .
C9A C4A C3A 124.3(2) . .
C5A C4A C3A 117.9(2) . .
C6A C5A C4A 122.3(2) . .
C6A C5A H5A 118.9 . .
C4A C5A H5A 118.9 . .
O3A C6A C5A 123.9(2) . .
O3A C6A C7A 117.4(2) . .
C5A C6A C7A 118.8(2) . .
O4A C7A C8A 124.5(2) . .
O4A C7A C6A 115.9(2) . .
C8A C7A C6A 119.6(2) . .
C7A C8A C9A 120.7(2) . .
C7A C8A K1 102.07(17) . 2
C9A C8A K1 85.17(18) . 2
C7A C8A H8A 119.7 . .
C9A C8A H8A 119.7 . .
K1 C8A H8A 82.7 2 .
C4A C9A C8A 120.8(2) . .
C4A C9A H9A 119.6 . .
C8A C9A H9A 119.6 . .
H51 O5 H52 105(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
K1 O3A 2.650(2) .
K1 O3 2.661(2) .
K1 O4A 2.720(2) .
K1 O1 2.737(2) 2_645
K1 O4 2.740(2) .
K1 O2 2.985(2) 1_566
K1 C8A 3.376(3) 2
O1 C1 1.207(3) .
O1 K1 2.737(2) 2_645
O2 C1 1.326(3) .
O2 K1 2.985(2) 1_544
O2 H21 0.86(5) .
O3 C6 1.364(3) .
O3 H31 0.82(4) .
O4 C7 1.363(3) .
O4 H4 0.83(4) .
C1 C2 1.474(4) .
C2 C3 1.313(4) .
C2 H2 0.9300 .
C3 C4 1.473(4) .
C3 H3 0.9300 .
C4 C9 1.383(4) .
C4 C5 1.394(4) .
C5 C6 1.380(4) .
C5 H5 0.9300 .
C6 C7 1.398(4) .
C7 C8 1.376(4) .
C8 C9 1.398(4) .
C8 H8 0.9300 .
C9 H9 0.9300 .
O1A C1A 1.246(3) .
O2A C1A 1.269(3) .
O3A C6A 1.362(3) .
O3A H3A1 0.83(4) .
O4A C7A 1.361(3) .
O4A H4A 0.76(3) .
C1A C2A 1.480(4) .
C2A C3A 1.314(4) .
C2A H2A 0.9300 .
C3A C4A 1.470(4) .
C3A H3A 0.9300 .
C4A C9A 1.385(4) .
C4A C5A 1.391(4) .
C5A C6A 1.380(4) .
C5A H5A 0.9300 .
C6A C7A 1.402(3) .
C7A C8A 1.377(4) .
C8A C9A 1.387(4) .
C8A K1 3.376(3) 2
C8A H8A 0.9300 .
C9A H9A 0.9300 .
O5 H51 0.74(4) .
O5 H52 0.88(4) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H21 O2A 0.86(5) 1.82(5) 2.641(3) 158(4) 1_634
O3 H31 O2A 0.82(4) 1.88(4) 2.655(3) 157(4) 1_645
O4 H4 O5 0.83(4) 1.93(4) 2.713(3) 158(3) .
O3A H3A1 O1A 0.83(4) 1.85(4) 2.667(3) 169(4) 2_566
O4A H4A O5 0.76(3) 2.03(3) 2.742(3) 155(3) .
O5 H51 O2A 0.74(4) 2.06(4) 2.795(3) 171(4) 2_455
O5 H52 O1A 0.88(4) 1.84(5) 2.718(3) 172(4) 1_544
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
O4A K1 O3 C6 11.4(3) . .
O1 K1 O3 C6 -142.8(2) 2_645 .
O4 K1 O3 C6 6.9(2) . .
O2 K1 O3 C6 146.3(2) 1_566 .
C8A K1 O3 C6 -73.4(2) 2 .
O3A K1 O4 C7 -179.55(19) . .
O3 K1 O4 C7 -7.18(19) . .
O4A K1 O4 C7 176.5(2) . .
O1 K1 O4 C7 49.6(3) 2_645 .
O2 K1 O4 C7 -50.3(2) 1_566 .
C8A K1 O4 C7 99.9(2) 2 .
K1 O1 C1 O2 119.2(3) 2_645 .
K1 O1 C1 C2 -59.7(5) 2_645 .
K1 O2 C1 O1 -134.7(3) 1_544 .
K1 O2 C1 C2 44.3(3) 1_544 .
O1 C1 C2 C3 -2.5(5) . .
O2 C1 C2 C3 178.5(3) . .
C1 C2 C3 C4 177.3(3) . .
C2 C3 C4 C9 3.9(5) . .
C2 C3 C4 C5 -174.8(3) . .
C9 C4 C5 C6 -1.2(4) . .
C3 C4 C5 C6 177.6(3) . .
K1 O3 C6 C5 171.0(2) . .
K1 O3 C6 C7 -6.5(4) . .
C4 C5 C6 O3 -177.2(3) . .
C4 C5 C6 C7 0.2(4) . .
K1 O4 C7 C8 -172.0(2) . .
K1 O4 C7 C6 7.3(3) . .
O3 C6 C7 O4 -0.7(4) . .
C5 C6 C7 O4 -178.3(3) . .
O3 C6 C7 C8 178.6(3) . .
C5 C6 C7 C8 1.0(4) . .
O4 C7 C8 C9 178.0(3) . .
C6 C7 C8 C9 -1.3(4) . .
C5 C4 C9 C8 0.9(4) . .
C3 C4 C9 C8 -177.8(3) . .
C7 C8 C9 C4 0.3(4) . .
O4A K1 O3A C6A 2.0(2) . .
O1 K1 O3A C6A 150.3(2) 2_645 .
O4 K1 O3A C6A -2.4(3) . .
O2 K1 O3A C6A -137.3(2) 1_566 .
C8A K1 O3A C6A 81.3(2) 2 .
O3A K1 O4A C7A -2.01(19) . .
O3 K1 O4A C7A 170.40(18) . .
O1 K1 O4A C7A -42.3(2) 2_645 .
O4 K1 O4A C7A 174.4(2) . .
O2 K1 O4A C7A 67.0(2) 1_566 .
C8A K1 O4A C7A -91.5(2) 2 .
O1A C1A C2A C3A -6.1(5) . .
O2A C1A C2A C3A 174.2(3) . .
C1A C2A C3A C4A -176.8(3) . .
C2A C3A C4A C9A 3.4(5) . .
C2A C3A C4A C5A -178.0(3) . .
C9A C4A C5A C6A -0.3(4) . .
C3A C4A C5A C6A -179.0(3) . .
K1 O3A C6A C5A 177.7(2) . .
K1 O3A C6A C7A -2.0(4) . .
C4A C5A C6A O3A 179.8(3) . .
C4A C5A C6A C7A -0.5(4) . .
K1 O4A C7A C8A -179.1(2) . .
K1 O4A C7A C6A 1.9(3) . .
O3A C6A C7A O4A 0.0(4) . .
C5A C6A C7A O4A -179.7(3) . .
O3A C6A C7A C8A -179.0(3) . .
C5A C6A C7A C8A 1.3(4) . .
O4A C7A C8A C9A 179.8(3) . .
C6A C7A C8A C9A -1.3(4) . .
O4A C7A C8A K1 -88.7(3) . 2
C6A C7A C8A K1 90.2(3) . 2
C5A C4A C9A C8A 0.3(4) . .
C3A C4A C9A C8A 178.9(3) . .
C7A C8A C9A C4A 0.5(4) . .
K1 C8A C9A C4A -100.7(3) 2 .
