Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2002

data_[Co(C5H4COOH)(C5H4COO)][HCOOH]
_database_code_CSD                  191329

_journal_coden_Cambridge      182

loop_
_publ_author_name
'Dario Braga'
'Roberto Gobetto'
'Fabrizia Grepioni'
'Lucia Maini'
'Amdir Masic'
'Michele Mazzotti'
'Katia Rubini'

_publ_contact_author_name     	'Dario Braga'  
_publ_contact_author_address 
;
University of Bologna
Dipartimento di Chimica G. Ciamicia
Via Selmi 2
Bologna
40126
ITALY
;

_publ_contact_author_email DBRAGA@CIAM.UNIBO.IT

_publ_requested_journal       'Chemical Communications'


_publ_section_title		
;
Supramolecular Gas-Solid Reaction Between Formic Acid
Vapours and Solid  [CoIII(h5-C5H4COOH)(h5-C5H4COO)]
;


_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
'C13 H11 Co O6' 
_chemical_formula_weight          322.15 

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' 
'Co'  'Co'   0.3494   0.9721 
'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' 

_symmetry_cell_setting            Monoclinic 
_symmetry_space_group_name_H-M    P2(1)/c 

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' 

_cell_length_a                    7.555(3) 
_cell_length_b                    8.937(3) 
_cell_length_c                    17.822(6) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  90.842(10) 
_cell_angle_gamma                 90.00 
_cell_volume                      1203.2(7) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     223(2) 
_cell_measurement_reflns_used     ? 
_cell_measurement_theta_min       ? 
_cell_measurement_theta_max       ? 

_exptl_crystal_description        prism 
_exptl_crystal_colour             yellow 
_exptl_crystal_size_max           0.22 
_exptl_crystal_size_mid           0.18 
_exptl_crystal_size_min           0.18 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.778 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              656 
_exptl_absorpt_coefficient_mu     1.450 
_exptl_absorpt_correction_type    Bruker-Smart 
_exptl_absorpt_correction_T_min   0.4125
_exptl_absorpt_correction_T_max   1.0000
_exptl_absorpt_process_details    ? 

_exptl_special_details 
; 
? 
; 

_diffrn_ambient_temperature       223(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'fine-focus sealed tube' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   ? 
_diffrn_measurement_method        ? 
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             9197 
_diffrn_reflns_av_R_equivalents   0.1029 
_diffrn_reflns_av_sigmaI/netI     0.0898 
_diffrn_reflns_limit_h_min        -10 
_diffrn_reflns_limit_h_max        10 
_diffrn_reflns_limit_k_min        -11 
_diffrn_reflns_limit_k_max        12 
_diffrn_reflns_limit_l_min        -23 
_diffrn_reflns_limit_l_max        25 
_diffrn_reflns_theta_min          2.29 
_diffrn_reflns_theta_max          29.99 
_reflns_number_total              3511 
_reflns_number_gt                 2748 
_reflns_threshold_expression      >2sigma(I) 

_computing_data_collection        ? 
_computing_cell_refinement        ? 
_computing_data_reduction         ? 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     ? 
_computing_publication_material   ? 

_refine_special_details 
; 
Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and 
goodness of fit S are based on F^2^, conventional R-factors R are based 
on F, with F set to zero for negative F^2^. The threshold expression of 
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is 
not relevant to the choice of reflections for refinement.  R-factors based 
on F^2^ are statistically about twice as large as those based on F, and R- 
factors based on ALL data will be even larger. 
; 

_refine_ls_structure_factor_coef  Fsqd  
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme       calc  
_refine_ls_weighting_details 
'calc w=1/[\s^2^(Fo^2^)+(0.0740P)^2^+3.2109P] where P=(Fo^2^+2Fc^2^)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     mixed 
_refine_ls_extinction_method      SHELXL 
_refine_ls_extinction_coef        0.0001(9) 
_refine_ls_extinction_expression 
'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' 
_refine_ls_number_reflns          3511 
_refine_ls_number_parameters      176 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0847 
_refine_ls_R_factor_gt            0.0591 
_refine_ls_wR_factor_ref          0.1551 
_refine_ls_wR_factor_gt           0.1330 
_refine_ls_goodness_of_fit_ref    0.995 
_refine_ls_restrained_S_all       0.995 
_refine_ls_shift/su_max           0.003 
_refine_ls_shift/su_mean          0.000 

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 
_atom_site_disorder_assembly 
_atom_site_disorder_group 
Co1 Co 0.21731(5) 0.65306(4) 0.14969(2) 0.01488(15) Uani 1 1 d . . . 
C1 C 0.1146(3) 0.8212(2) 0.21315(10) 0.0192(6) Uani 1 1 d G . . 
H1 H 0.1688 0.8672 0.2543 0.023 Uiso 1 1 calc R . . 
C2 C 0.0031(3) 0.6935(2) 0.21538(11) 0.0229(7) Uani 1 1 d G . . 
H2 H -0.0286 0.6411 0.2582 0.027 Uiso 1 1 calc R . . 
C3 C -0.0516(3) 0.6597(2) 0.14070(13) 0.0249(7) Uani 1 1 d G . . 
H3 H -0.1253 0.5814 0.1260 0.030 Uiso 1 1 calc R . . 
C4 C 0.0263(3) 0.7666(3) 0.09232(9) 0.0200(6) Uani 1 1 d G . . 
H4 H 0.0124 0.7706 0.0404 0.024 Uiso 1 1 calc R . . 
C5 C 0.1290(3) 0.8664(2) 0.13710(11) 0.0170(6) Uani 1 1 d G . . 
C6 C 0.2307(4) 0.9976(3) 0.11027(18) 0.0180(6) Uani 1 1 d . . . 
O1 O 0.2875(4) 1.0914(3) 0.15322(14) 0.0239(5) Uani 1 1 d . . . 
O2 O 0.2445(4) 0.9989(3) 0.03731(15) 0.0257(6) Uani 1 1 d . . . 
C7 C 0.4612(3) 0.5956(3) 0.19033(10) 0.0203(6) Uani 1 1 d G . . 
H7 H 0.5204 0.6392 0.2309 0.024 Uiso 1 1 calc R . . 
C8 C 0.3450(3) 0.4710(2) 0.19349(10) 0.0233(7) Uani 1 1 d G . . 
H8 H 0.3146 0.4186 0.2365 0.028 Uiso 1 1 calc R . . 
C9 C 0.2831(3) 0.4405(2) 0.11944(12) 0.0226(7) Uani 1 1 d G . . 
H9 H 0.2052 0.3645 0.1054 0.027 Uiso 1 1 calc R . . 
C10 C 0.3612(3) 0.5462(3) 0.07051(9) 0.0197(6) Uani 1 1 d G . . 
H10 H 0.3433 0.5517 0.0188 0.024 Uiso 1 1 calc R . . 
C11 C 0.4712(3) 0.6421(2) 0.11432(11) 0.0171(6) Uani 1 1 d G . . 
C12 C 0.5742(4) 0.7739(3) 0.08562(18) 0.0179(6) Uani 1 1 d . . . 
O3 O 0.6212(4) 0.8676(3) 0.13345(15) 0.0246(5) Uani 1 1 d . . . 
O4 O 0.6055(3) 0.7739(3) 0.01711(14) 0.0238(5) Uani 1 1 d . . . 
H200 H 0.302(8) 1.044(8) 0.024(4) 0.049(19) Uiso 1 1 d . . . 
H500 H 0.750(9) 1.028(9) 0.126(4) 0.07(2) Uiso 1 1 d . . . 
C13 C 0.7332(6) 1.2157(4) 0.1001(2) 0.0288(8) Uani 1 1 d . . . 
H113 H 0.614(7) 1.194(7) 0.083(3) 0.037(13) Uiso 1 1 d . . . 
O5 O 0.8153(4) 1.0994(3) 0.12767(18) 0.0324(6) Uani 1 1 d . . . 
O6 O 0.8015(6) 1.3366(4) 0.0967(2) 0.0494(10) Uani 1 1 d . . . 

loop_ 
_atom_site_aniso_label 
_atom_site_aniso_U_11 
_atom_site_aniso_U_22 
_atom_site_aniso_U_33 
_atom_site_aniso_U_23 
_atom_site_aniso_U_13 
_atom_site_aniso_U_12 
Co1 0.0186(2) 0.0075(2) 0.0186(2) 0.00114(14) -0.00040(14) 0.00022(15) 
C1 0.0249(15) 0.0103(13) 0.0224(14) 0.0002(10) 0.0044(11) 0.0045(11) 
C2 0.0221(15) 0.0159(14) 0.0308(17) 0.0055(12) 0.0080(12) 0.0014(12) 
C3 0.0201(15) 0.0152(14) 0.0395(19) 0.0042(13) 0.0002(13) 0.0000(12) 
C4 0.0188(14) 0.0133(13) 0.0276(16) 0.0035(11) -0.0052(11) 0.0004(11) 
C5 0.0207(14) 0.0093(13) 0.0211(14) 0.0011(10) 0.0008(11) 0.0023(11) 
C6 0.0198(14) 0.0106(13) 0.0236(14) 0.0011(10) -0.0001(11) 0.0022(11) 
O1 0.0336(13) 0.0121(11) 0.0257(12) -0.0016(9) -0.0039(10) -0.0031(10) 
O2 0.0378(15) 0.0167(12) 0.0228(12) 0.0009(9) 0.0031(10) -0.0089(11) 
C7 0.0231(15) 0.0181(14) 0.0196(14) 0.0037(11) -0.0021(11) 0.0050(12) 
C8 0.0308(17) 0.0118(13) 0.0275(16) 0.0088(12) 0.0027(13) 0.0067(12) 
C9 0.0301(17) 0.0063(12) 0.0317(17) -0.0008(11) 0.0051(13) 0.0007(12) 
C10 0.0267(15) 0.0133(13) 0.0191(14) -0.0011(11) 0.0016(11) 0.0020(12) 
C11 0.0207(14) 0.0102(12) 0.0204(14) 0.0012(10) -0.0008(11) 0.0039(11) 
C12 0.0175(13) 0.0110(13) 0.0250(14) 0.0024(11) -0.0028(11) 0.0014(11) 
O3 0.0294(12) 0.0179(12) 0.0263(12) -0.0033(9) -0.0030(9) -0.0040(10) 
O4 0.0301(12) 0.0175(11) 0.0239(11) 0.0023(9) 0.0018(9) -0.0040(10) 
C13 0.039(2) 0.0207(17) 0.0260(16) -0.0006(13) -0.0090(15) -0.0038(15) 
O5 0.0356(15) 0.0205(13) 0.0406(15) 0.0042(11) -0.0134(12) -0.0069(12) 
O6 0.081(3) 0.0231(15) 0.0435(18) 0.0023(13) -0.0198(17) -0.0218(16) 

_geom_special_details 
; 
All esds (except the esd in the dihedral angle between two l.s. planes) 
are estimated using the full covariance matrix.  The cell esds are taken 
into account individually in the estimation of esds in distances, angles 
and torsion angles; correlations between esds in cell parameters are only 
used when they are defined by crystal symmetry.  An approximate (isotropic) 
treatment of cell esds is used for estimating esds involving l.s. planes. 
; 

loop_ 
_geom_bond_atom_site_label_1 
_geom_bond_atom_site_label_2 
_geom_bond_distance 
_geom_bond_site_symmetry_2 
_geom_bond_publ_flag 
Co1 C4 2.029(2) . ? 
Co1 C11 2.031(2) . ? 
Co1 C10 2.032(2) . ? 
Co1 C5 2.032(2) . ? 
Co1 C7 2.036(2) . ? 
Co1 C3 2.036(2) . ? 
Co1 C9 2.039(2) . ? 
Co1 C8 2.041(2) . ? 
Co1 C1 2.041(2) . ? 
Co1 C2 2.044(2) . ? 
C1 C2 1.4200 . ? 
C1 C5 1.4200 . ? 
C1 H1 0.9300 . ? 
C2 C3 1.4200 . ? 
C2 H2 0.9300 . ? 
C3 C4 1.4200 . ? 
C3 H3 0.9300 . ? 
C4 C5 1.4200 . ? 
C4 H4 0.9300 . ? 
C5 C6 1.485(4) . ? 
C6 O1 1.209(4) . ? 
C6 O2 1.306(4) . ? 
O2 H200 0.64(7) . ? 
C7 C8 1.4200 . ? 
C7 C11 1.4200 . ? 
C7 H7 0.9300 . ? 
C8 C9 1.4200 . ? 
C8 H8 0.9300 . ? 
C9 C10 1.4200 . ? 
C9 H9 0.9300 . ? 
C10 C11 1.4200 . ? 
C10 H10 0.9300 . ? 
C11 C12 1.505(4) . ? 
C12 O3 1.243(4) . ? 
C12 O4 1.247(4) . ? 
O3 H500 1.74(8) . ? 
C13 O6 1.199(5) . ? 
C13 O5 1.303(5) . ? 
C13 H113 0.97(5) . ? 
O5 H500 0.81(7) . ? 

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 
_geom_angle_publ_flag 
C4 Co1 C11 122.42(9) . . ? 
C4 Co1 C10 105.60(8) . . ? 
C11 Co1 C10 40.9 . . ? 
C4 Co1 C5 40.9 . . ? 
C11 Co1 C5 108.74(8) . . ? 
C10 Co1 C5 122.85(8) . . ? 
C4 Co1 C7 159.89(9) . . ? 
C11 Co1 C7 40.9 . . ? 
C10 Co1 C7 68.78(5) . . ? 
C5 Co1 C7 124.76(9) . . ? 
C4 Co1 C3 40.9 . . ? 
C11 Co1 C3 157.37(9) . . ? 
C10 Co1 C3 120.15(9) . . ? 
C5 Co1 C3 68.78(5) . . ? 
C7 Co1 C3 158.77(9) . . ? 
C4 Co1 C9 120.50(9) . . ? 
C11 Co1 C9 68.76(5) . . ? 
C10 Co1 C9 40.8 . . ? 
C5 Co1 C9 157.91(9) . . ? 
C7 Co1 C9 68.66(5) . . ? 
C3 Co1 C9 104.69(8) . . ? 
C4 Co1 C8 156.99(9) . . ? 
C11 Co1 C8 68.71(5) . . ? 
C10 Co1 C8 68.68(5) . . ? 
C5 Co1 C8 160.60(9) . . ? 
C7 Co1 C8 40.8 . . ? 
C3 Co1 C8 121.25(9) . . ? 
C9 Co1 C8 40.7 . . ? 
C4 Co1 C1 68.74(5) . . ? 
C11 Co1 C1 125.17(9) . . ? 
C10 Co1 C1 160.45(9) . . ? 
C5 Co1 C1 40.8 . . ? 
C7 Co1 C1 109.75(8) . . ? 
C3 Co1 C1 68.60(5) . . ? 
C9 Co1 C1 158.29(9) . . ? 
C8 Co1 C1 123.81(9) . . ? 
C4 Co1 C2 68.69(6) . . ? 
C11 Co1 C2 161.13(9) . . ? 
C10 Co1 C2 156.50(9) . . ? 
C5 Co1 C2 68.63(5) . . ? 
C7 Co1 C2 124.14(9) . . ? 
C3 Co1 C2 40.7 . . ? 
C9 Co1 C2 120.98(9) . . ? 
C8 Co1 C2 107.20(8) . . ? 
C1 Co1 C2 40.7 . . ? 
C2 C1 C5 108.0 . . ? 
C2 C1 Co1 69.76(9) . . ? 
C5 C1 Co1 69.25(9) . . ? 
C2 C1 H1 126.0 . . ? 
C5 C1 H1 126.0 . . ? 
Co1 C1 H1 126.6 . . ? 
C3 C2 C1 108.0 . . ? 
C3 C2 Co1 69.35(9) . . ? 
C1 C2 Co1 69.56(9) . . ? 
C3 C2 H2 126.0 . . ? 
C1 C2 H2 126.0 . . ? 
Co1 C2 H2 126.7 . . ? 
C2 C3 C4 108.0 . . ? 
C2 C3 Co1 69.92(9) . . ? 
C4 C3 Co1 69.28(9) . . ? 
C2 C3 H3 126.0 . . ? 
C4 C3 H3 126.0 . . ? 
Co1 C3 H3 126.4 . . ? 
C5 C4 C3 108.0 . . ? 
C5 C4 Co1 69.64(9) . . ? 
C3 C4 Co1 69.83(9) . . ? 
C5 C4 H4 126.0 . . ? 
C3 C4 H4 126.0 . . ? 
Co1 C4 H4 126.1 . . ? 
C4 C5 C1 108.0 . . ? 
C4 C5 C6 126.60(19) . . ? 
C1 C5 C6 125.38(19) . . ? 
C4 C5 Co1 69.42(9) . . ? 
C1 C5 Co1 69.94(9) . . ? 
C6 C5 Co1 127.28(18) . . ? 
O1 C6 O2 126.2(3) . . ? 
O1 C6 C5 121.6(3) . . ? 
O2 C6 C5 112.1(3) . . ? 
C6 O2 H200 115(6) . . ? 
C8 C7 C11 108.0 . . ? 
C8 C7 Co1 69.80(9) . . ? 
C11 C7 Co1 69.36(9) . . ? 
C8 C7 H7 126.0 . . ? 
C11 C7 H7 126.0 . . ? 
Co1 C7 H7 126.4 . . ? 
C9 C8 C7 108.0 . . ? 
C9 C8 Co1 69.55(9) . . ? 
C7 C8 Co1 69.43(9) . . ? 
C9 C8 H8 126.0 . . ? 
C7 C8 H8 126.0 . . ? 
Co1 C8 H8 126.6 . . ? 
C10 C9 C8 108.0 . . ? 
C10 C9 Co1 69.35(9) . . ? 
C8 C9 Co1 69.71(9) . . ? 
C10 C9 H9 126.0 . . ? 
C8 C9 H9 126.0 . . ? 
Co1 C9 H9 126.5 . . ? 
C11 C10 C9 108.0 . . ? 
C11 C10 Co1 69.48(9) . . ? 
C9 C10 Co1 69.82(9) . . ? 
C11 C10 H10 126.0 . . ? 
C9 C10 H10 126.0 . . ? 
Co1 C10 H10 126.3 . . ? 
C10 C11 C7 108.0 . . ? 
C10 C11 C12 125.93(19) . . ? 
C7 C11 C12 126.02(19) . . ? 
C10 C11 Co1 69.61(9) . . ? 
C7 C11 Co1 69.76(9) . . ? 
C12 C11 Co1 124.28(18) . . ? 
O3 C12 O4 127.9(3) . . ? 
O3 C12 C11 116.0(3) . . ? 
O4 C12 C11 116.0(3) . . ? 
C12 O3 H500 131(2) . . ? 
O6 C13 O5 122.3(4) . . ? 
O6 C13 H113 124(3) . . ? 
O5 C13 H113 113(3) . . ? 
C13 O5 H500 109(5) . . ? 

_diffrn_measured_fraction_theta_max    0.998 
_diffrn_reflns_theta_full              29.99 
_diffrn_measured_fraction_theta_full   0.998 
_refine_diff_density_max    1.142 
_refine_diff_density_min   -1.066 
_refine_diff_density_rms    0.163