#------------------------------------------------------------------------------ #$Date: 2014-07-11 19:04:56 +0300 (Fri, 11 Jul 2014) $ #$Revision: 120072 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/22/84/2228469.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_2228469 loop_ _publ_author_name 'Zhu, Li-Cai' _publ_section_title ; 3,4-Dihydroxybenzoic acid pyridine monosolvate ; _journal_coeditor_code NC2201 _journal_issue 12 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o3225 _journal_volume 66 _journal_year 2010 _chemical_formula_iupac 'C7 H6 O4, C5 H5 N' _chemical_formula_moiety 'C7 H6 O4, C5 H5 N' _chemical_formula_sum 'C12 H11 N O4' _chemical_formula_weight 233.22 _chemical_name_systematic ; 3,4-Dihydroxybenzoic acid pyridine monosolvate ; _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 _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 108.0420(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 11.9907(11) _cell_length_b 9.1400(8) _cell_length_c 10.3541(9) _cell_measurement_reflns_used 1420 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 25.35 _cell_measurement_theta_min 2.86 _cell_volume 1078.96(17) _computing_cell_refinement 'SAINT (Bruker, 2004)' _computing_data_collection 'APEX2 (Bruker, 2004)' _computing_data_reduction 'SAINT (Bruker, 2004)' _computing_molecular_graphics 'XP in SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXL97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker APEXII area-detector' _diffrn_measurement_method 'f and \w scan' _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 0.0278 _diffrn_reflns_av_sigmaI/netI 0.0309 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 5415 _diffrn_reflns_theta_full 25.20 _diffrn_reflns_theta_max 25.20 _diffrn_reflns_theta_min 1.79 _exptl_absorpt_coefficient_mu 0.109 _exptl_absorpt_correction_type none _exptl_crystal_colour Colorless _exptl_crystal_density_diffrn 1.436 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 488 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.26 _refine_diff_density_max 0.192 _refine_diff_density_min -0.199 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 157 _refine_ls_number_reflns 1939 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.051 _refine_ls_R_factor_all 0.0533 _refine_ls_R_factor_gt 0.0388 _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^)+(0.0507P)^2^+0.1871P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0977 _refine_ls_wR_factor_ref 0.1069 _reflns_number_gt 1484 _reflns_number_total 1939 _reflns_threshold_expression I>2sigma(I) _[local]_cod_data_source_file nc2201.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_database_code 2228469 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_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 _atom_site_disorder_assembly _atom_site_disorder_group C C1 0.10603(14) 0.03303(18) 0.32574(17) 0.0312(4) Uani d . 1 . . H H1 0.0994 -0.0100 0.2423 0.037 Uiso calc R 1 . . C C2 0.02226(14) 0.13119(18) 0.33621(16) 0.0298(4) Uani d . 1 . . C C3 0.03141(15) 0.19523(18) 0.46141(17) 0.0325(4) Uani d . 1 . . C C4 0.12446(16) 0.1597(2) 0.57352(17) 0.0386(4) Uani d . 1 . . H H4 0.1305 0.2020 0.6571 0.046 Uiso calc R 1 . . C C5 0.20928(15) 0.0613(2) 0.56300(17) 0.0377(4) Uani d . 1 . . H H5 0.2719 0.0382 0.6392 0.045 Uiso calc R 1 . . C C6 0.20063(14) -0.00256(18) 0.43869(16) 0.0307(4) Uani d . 1 . . C C7 0.28879(14) -0.11003(19) 0.42301(17) 0.0329(4) Uani d . 1 . . C C8 0.50997(17) 0.6408(2) 0.35399(19) 0.0449(5) Uani d . 1 . . H H8 0.4397 0.6633 0.2877 0.054 Uiso calc R 1 . . C C9 0.58295(18) 0.5384(2) 0.3254(2) 0.0503(5) Uani d . 1 . . H H9 0.5626 0.4930 0.2408 0.060 Uiso calc R 1 . . C C10 0.68609(18) 0.5041(2) 0.4233(2) 0.0500(5) Uani d . 1 . . H H10 0.7361 0.4339 0.4067 0.060 Uiso calc R 1 . . C C11 0.71475(17) 0.5750(2) 0.5466(2) 0.0496(5) Uani d . 1 . . H H11 0.7847 0.5545 0.6142 0.060 Uiso calc R 1 . . C C12 0.63792(17) 0.6765(2) 0.56739(19) 0.0455(5) Uani d . 1 . . H H12 0.6573 0.7247 0.6505 0.055 Uiso calc R 1 . . O O1 -0.06869(10) 0.16177(13) 0.22200(11) 0.0382(3) Uani d . 1 . . H H1A -0.1153 0.2163 0.2415 0.057 Uiso calc R 1 . . O O2 -0.05466(11) 0.29250(14) 0.46347(12) 0.0425(3) Uani d . 1 . . H H2 -0.0526 0.3074 0.5423 0.064 Uiso calc R 1 . . O O3 0.38824(10) -0.10876(15) 0.51991(13) 0.0486(4) Uani d . 1 . . H H3 0.4329 -0.1683 0.5030 0.073 Uiso calc R 1 . . O O4 0.26885(10) -0.19100(13) 0.32362(12) 0.0384(3) Uani d . 1 . . N N1 0.53651(13) 0.70907(16) 0.47356(15) 0.0406(4) Uani 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 C1 0.0317(9) 0.0346(9) 0.0286(9) -0.0025(8) 0.0110(7) -0.0007(7) C2 0.0274(9) 0.0338(9) 0.0265(8) -0.0004(7) 0.0060(7) 0.0050(7) C3 0.0339(9) 0.0334(9) 0.0329(9) 0.0022(8) 0.0140(8) 0.0023(7) C4 0.0411(10) 0.0464(10) 0.0272(9) 0.0039(9) 0.0089(8) -0.0040(8) C5 0.0326(10) 0.0453(10) 0.0309(9) 0.0041(8) 0.0039(8) 0.0002(8) C6 0.0278(9) 0.0340(9) 0.0299(9) -0.0015(7) 0.0086(7) 0.0016(7) C7 0.0287(9) 0.0366(9) 0.0323(9) -0.0012(8) 0.0081(8) 0.0032(7) C8 0.0391(11) 0.0522(12) 0.0403(11) 0.0056(9) 0.0075(9) -0.0002(9) C9 0.0507(12) 0.0546(12) 0.0460(11) 0.0056(10) 0.0158(10) -0.0064(10) C10 0.0480(12) 0.0494(12) 0.0568(13) 0.0128(10) 0.0225(11) 0.0041(10) C11 0.0397(11) 0.0587(13) 0.0477(12) 0.0116(10) 0.0093(9) 0.0084(10) C12 0.0424(11) 0.0538(12) 0.0376(10) 0.0046(10) 0.0087(9) -0.0006(9) O1 0.0351(7) 0.0481(8) 0.0290(6) 0.0102(6) 0.0065(6) 0.0007(5) O2 0.0464(8) 0.0500(8) 0.0311(7) 0.0165(6) 0.0122(6) 0.0008(6) O3 0.0322(7) 0.0618(9) 0.0437(8) 0.0133(7) 0.0001(6) -0.0137(6) O4 0.0309(7) 0.0457(7) 0.0363(7) 0.0017(6) 0.0072(5) -0.0079(6) N1 0.0361(9) 0.0441(9) 0.0409(9) 0.0054(7) 0.0109(7) 0.0005(7) 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 _geom_angle_publ_flag C2 C1 C6 . . 120.72(15) ? C2 C1 H1 . . 119.6 ? C6 C1 H1 . . 119.6 ? O1 C2 C1 . . 118.14(14) ? O1 C2 C3 . . 122.02(15) ? C1 C2 C3 . . 119.83(15) ? O2 C3 C4 . . 123.97(15) ? O2 C3 C2 . . 116.41(15) ? C4 C3 C2 . . 119.62(15) ? C3 C4 C5 . . 120.62(16) ? C3 C4 H4 . . 119.7 ? C5 C4 H4 . . 119.7 ? C4 C5 C6 . . 119.97(16) ? C4 C5 H5 . . 120.0 ? C6 C5 H5 . . 120.0 ? C5 C6 C1 . . 119.23(15) ? C5 C6 C7 . . 121.82(15) ? C1 C6 C7 . . 118.94(15) ? O4 C7 O3 . . 123.08(16) ? O4 C7 C6 . . 121.87(15) ? O3 C7 C6 . . 115.02(15) ? N1 C8 C9 . . 122.25(18) ? N1 C8 H8 . . 118.9 ? C9 C8 H8 . . 118.9 ? C10 C9 C8 . . 118.97(19) ? C10 C9 H9 . . 120.5 ? C8 C9 H9 . . 120.5 ? C9 C10 C11 . . 119.18(19) ? C9 C10 H10 . . 120.4 ? C11 C10 H10 . . 120.4 ? C12 C11 C10 . . 118.50(19) ? C12 C11 H11 . . 120.7 ? C10 C11 H11 . . 120.7 ? N1 C12 C11 . . 122.82(18) ? N1 C12 H12 . . 118.6 ? C11 C12 H12 . . 118.6 ? C2 O1 H1A . . 109.5 ? C3 O2 H2 . . 109.5 ? C7 O3 H3 . . 109.5 ? C8 N1 C12 . . 118.25(16) ? 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 C1 C2 . 1.376(2) ? C1 C6 . 1.392(2) ? C1 H1 . 0.9300 ? C2 O1 . 1.3664(18) ? C2 C3 . 1.395(2) ? C3 O2 . 1.367(2) ? C3 C4 . 1.377(2) ? C4 C5 . 1.387(2) ? C4 H4 . 0.9300 ? C5 C6 . 1.388(2) ? C5 H5 . 0.9300 ? C6 C7 . 1.488(2) ? C7 O4 . 1.2294(19) ? C7 O3 . 1.299(2) ? C8 N1 . 1.334(2) ? C8 C9 . 1.375(3) ? C8 H8 . 0.9300 ? C9 C10 . 1.371(3) ? C9 H9 . 0.9300 ? C10 C11 . 1.377(3) ? C10 H10 . 0.9300 ? C11 C12 . 1.371(3) ? C11 H11 . 0.9300 ? C12 N1 . 1.334(2) ? C12 H12 . 0.9300 ? O1 H1A . 0.8200 ? O2 H2 . 0.8200 ? O3 H3 . 0.8200 ? 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 O1 H1A O4 2 0.82 1.95 2.6631(17) 145.4 O2 H2 O1 4_566 0.82 1.95 2.7654(16) 172.9 O3 H3 N1 1_545 0.82 1.77 2.5869(19) 176.5 _cod_database_fobs_code 2228469 _journal_paper_doi 10.1107/S1600536810047082