#------------------------------------------------------------------------------ #$Date: 2010-01-30 15:59:17 +0200 (Sat, 30 Jan 2010) $ #$Revision: 966 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2214055.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_2214055 _space_group_IT_number 14 _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _[local]_cod_cif_authors_sg_H-M 'P 21/c' loop_ _publ_author_name 'Mazurek, Jaroslaw' 'Dova, Eva' 'Helmond, Rosaline' _publ_section_title ; 3,4-Dihydroxybenzoic acid acetonitrile solvate at 120 K ; _journal_coeditor_code BH2117 _journal_issue 7 _journal_name_full 'Acta Crystallographica, Section E' _journal_page_first o3289 _journal_page_last o3289 _journal_volume 63 _journal_year 2007 _chemical_formula_iupac 'C7 H6 O4, C2 H3 N' _chemical_formula_moiety 'C7 H6 O4, C2 H3 N' _chemical_formula_sum 'C9 H9 N O4' _chemical_formula_weight 195.17 _chemical_name_systematic '3,4-Dihydroxybenozic acid acetonitile solvate' _symmetry_cell_setting monoclinic _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 99.4790(14) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 6.3792(6) _cell_length_b 10.4941(8) _cell_length_c 13.7634(12) _cell_measurement_reflns_used 2242 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 34.97 _cell_measurement_theta_min 0.998 _cell_volume 908.80(14) _computing_cell_refinement 'HKL (Otwinowski & Minor, 1997)' _computing_data_collection 'KappaCCD Server Software (Nonius, 1997)' _computing_data_reduction ; DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997) ; _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _diffrn_ambient_temperature 120(2) _diffrn_measured_fraction_theta_full 0.989 _diffrn_measured_fraction_theta_max 0.989 _diffrn_measurement_device 'Nonius KappaCCD' _diffrn_measurement_method CCD _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0261 _diffrn_reflns_av_sigmaI/netI 0.0310 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 9774 _diffrn_reflns_theta_full 34.97 _diffrn_reflns_theta_max 34.97 _diffrn_reflns_theta_min 3.57 _exptl_absorpt_coefficient_mu 0.114 _exptl_absorpt_correction_type none _exptl_crystal_colour Colourless _exptl_crystal_density_diffrn 1.427 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Parallelepiped _exptl_crystal_F_000 408 _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _refine_diff_density_max 0.488 _refine_diff_density_min -0.374 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 152 _refine_ls_number_reflns 3948 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.054 _refine_ls_R_factor_all 0.0511 _refine_ls_R_factor_gt 0.0447 _refine_ls_shift/su_max 0.025 _refine_ls_shift/su_mean 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0745P)^2^+0.1499P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1250 _refine_ls_wR_factor_ref 0.1308 _reflns_number_gt 3466 _reflns_number_total 3948 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file bh2117.cif 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_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_ _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 O O1 -0.25161(9) 1.05508(6) 0.06328(5) 0.02453(13) Uani d . 1 H H1 -0.381(4) 1.080(2) 0.0265(17) 0.073(6) Uiso d . 1 C C2 -0.24757(11) 0.93132(7) 0.07528(5) 0.01851(13) Uani d . 1 O O3 -0.39826(10) 0.86069(6) 0.04151(5) 0.02659(14) Uani d . 1 C C4 -0.04961(10) 0.87984(7) 0.13234(5) 0.01694(13) Uani d . 1 C C5 0.12150(11) 0.96085(7) 0.16568(5) 0.01803(13) Uani d . 1 H H5 0.113(2) 1.0546(14) 0.1515(10) 0.030(3) Uiso d . 1 C C6 0.30668(11) 0.91081(7) 0.21885(5) 0.01761(13) Uani d . 1 O O7 0.48099(9) 0.98127(6) 0.25608(5) 0.02552(14) Uani d . 1 H H7 0.464(3) 1.059(2) 0.2347(13) 0.052(5) Uiso d . 1 C C8 0.32202(10) 0.77978(7) 0.23852(5) 0.01706(13) Uani d . 1 O O9 0.50348(9) 0.72937(5) 0.29073(5) 0.02233(13) Uani d . 1 H H9 0.596(3) 0.7824(19) 0.3070(14) 0.056(5) Uiso d . 1 C C10 0.15149(11) 0.69939(7) 0.20561(6) 0.01884(13) Uani d . 1 H H10 0.1655(19) 0.6080(12) 0.2212(9) 0.023(3) Uiso d . 1 C C11 -0.03439(11) 0.74969(7) 0.15260(5) 0.01867(13) Uani d . 1 H H11 -0.155(2) 0.6970(14) 0.1283(10) 0.030(3) Uiso d . 1 N N12 0.88052(13) 0.84338(8) 0.38793(6) 0.02975(16) Uani d . 1 C C13 1.05256(13) 0.86299(8) 0.42443(6) 0.02431(15) Uani d . 1 C C14 1.26991(13) 0.89099(10) 0.47069(7) 0.02865(18) Uani d . 1 H H14A 1.3432 0.9365 0.4239 0.043 Uiso calc R 1 H H14B 1.3448 0.8111 0.4902 0.043 Uiso calc R 1 H H14C 1.2680 0.9442 0.5291 0.043 Uiso calc R 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 O1 0.0197(2) 0.0181(3) 0.0325(3) 0.00133(19) -0.0057(2) 0.0037(2) C2 0.0154(3) 0.0175(3) 0.0212(3) 0.0009(2) -0.0013(2) -0.0003(2) O3 0.0183(3) 0.0207(3) 0.0363(3) -0.00038(19) -0.0086(2) -0.0010(2) C4 0.0134(3) 0.0165(3) 0.0196(3) 0.0007(2) -0.0014(2) -0.0001(2) C5 0.0147(3) 0.0148(3) 0.0232(3) 0.0003(2) -0.0010(2) 0.0014(2) C6 0.0135(3) 0.0138(3) 0.0241(3) -0.00094(19) -0.0012(2) 0.0004(2) O7 0.0162(2) 0.0147(2) 0.0414(3) -0.00371(18) -0.0077(2) 0.0035(2) C8 0.0130(2) 0.0140(3) 0.0227(3) 0.00081(19) -0.0012(2) 0.0000(2) O9 0.0148(2) 0.0150(2) 0.0338(3) 0.00113(17) -0.00611(19) 0.00066(19) C10 0.0158(3) 0.0135(3) 0.0257(3) -0.0006(2) -0.0012(2) -0.0003(2) C11 0.0151(3) 0.0157(3) 0.0237(3) -0.0012(2) -0.0014(2) -0.0011(2) N12 0.0237(3) 0.0309(4) 0.0329(4) 0.0007(3) -0.0004(3) -0.0005(3) C13 0.0226(3) 0.0236(3) 0.0258(3) 0.0024(3) 0.0012(3) -0.0013(3) C14 0.0204(3) 0.0325(4) 0.0312(4) 0.0012(3) -0.0013(3) -0.0052(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C2 1.3089(9) O1 H1 0.93(2) C2 O3 1.2419(9) C2 C4 1.4753(10) C4 C11 1.3942(10) C4 C5 1.3999(10) C5 C6 1.3864(10) C5 H5 1.003(14) C6 O7 1.3631(9) C6 C8 1.4017(10) O7 H7 0.87(2) C8 O9 1.3646(8) C8 C10 1.3922(10) O9 H9 0.82(2) C10 C11 1.3900(10) C10 H10 0.983(13) C11 H11 0.960(14) N12 C13 1.1478(12) C13 C14 1.4572(12) C14 H14A 0.9800 C14 H14B 0.9800 C14 H14C 0.9800 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C2 O1 H1 110.1(14) O3 C2 O1 123.16(7) O3 C2 C4 121.51(7) O1 C2 C4 115.33(6) C11 C4 C5 120.30(6) C11 C4 C2 119.37(6) C5 C4 C2 120.33(6) C6 C5 C4 119.58(6) C6 C5 H5 119.2(8) C4 C5 H5 121.2(8) O7 C6 C5 124.35(6) O7 C6 C8 115.65(6) C5 C6 C8 119.99(6) C6 O7 H7 109.3(12) O9 C8 C10 119.08(6) O9 C8 C6 120.54(6) C10 C8 C6 120.37(6) C8 O9 H9 113.2(13) C11 C10 C8 119.60(6) C11 C10 H10 121.6(7) C8 C10 H10 118.8(7) C10 C11 C4 120.16(6) C10 C11 H11 121.9(9) C4 C11 H11 118.0(9) N12 C13 C14 178.69(10) C13 C14 H14A 109.5 C13 C14 H14B 109.5 H14A C14 H14B 109.5 C13 C14 H14C 109.5 H14A C14 H14C 109.5 H14B C14 H14C 109.5 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 _geom_hbond_publ_flag O1 H1 O3 3_475 0.93(2) 1.68(2) 2.6056(9) 174(2) yes O7 H7 O9 2_655 0.87(2) 1.84(2) 2.6878(8) 164.8(17) yes O9 H9 N12 . 0.82(2) 2.07(2) 2.8189(10) 153.0(18) yes _cod_database_code 2214055