#------------------------------------------------------------------------------ #$Date: 2013-12-29 13:49:26 +0200 (Sun, 29 Dec 2013) $ #$Revision: 91935 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/50/64/4506453.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_4506453 loop_ _publ_author_name 'Thakuria, Ranjit' 'Cherukuvada, Suryanarayan' 'Nangia, Ashwini' _publ_section_title ; Crystal Structures of Pyrogallol, Its Hydrate, and Stable MultipleZ′ Cocrystals with N-Heterocycles Containing Metastable Conformers of Pyrogallol ; _journal_issue 8 _journal_name_full 'Crystal Growth & Design' _journal_page_first 3944 _journal_volume 12 _journal_year 2012 _chemical_formula_moiety 'C6 H6 O3' _chemical_formula_sum 'C6 H6 O3' _chemical_formula_weight 126.11 _chemical_name_systematic ; pyrogallol ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 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 115.4840(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 12.1144(11) _cell_length_b 3.7765(3) _cell_length_c 13.1365(12) _cell_measurement_reflns_used 6034 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 26.12 _cell_measurement_theta_min 2.38 _cell_volume 542.52(8) _computing_cell_refinement 'Bruker SMART' _computing_data_collection 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _diffrn_ambient_temperature 100(2) _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _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 0.0234 _diffrn_reflns_av_sigmaI/netI 0.0168 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 5197 _diffrn_reflns_theta_full 26.03 _diffrn_reflns_theta_max 26.03 _diffrn_reflns_theta_min 1.91 _exptl_absorpt_coefficient_mu 0.126 _exptl_absorpt_correction_T_max 0.9851 _exptl_absorpt_correction_T_min 0.9574 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Bruker AXS SADABS program' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.544 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 264 _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.12 _refine_diff_density_max 0.270 _refine_diff_density_min -0.156 _refine_diff_density_rms 0.046 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 94 _refine_ls_number_reflns 1075 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.064 _refine_ls_R_factor_all 0.0392 _refine_ls_R_factor_gt 0.0372 _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^)+(0.0536P)^2^+0.3047P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0981 _refine_ls_wR_factor_ref 0.0998 _reflns_number_gt 1019 _reflns_number_total 1075 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file cg3003367_si_002.cif _[local]_cod_data_source_block Pyrogallol_guestfree _[local]_cod_cif_authors_sg_H-M 'P2(1)/n ' _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26. Automatic conversion script Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius ; _cod_database_code 4506453 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_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 C1 C 0.10470(12) 0.9533(4) 0.83510(12) 0.0167(3) Uani 1 1 d . C2 C 0.06179(12) 0.9188(4) 0.71909(12) 0.0165(3) Uani 1 1 d . C3 C -0.05175(13) 0.7657(4) 0.65688(12) 0.0180(3) Uani 1 1 d . C4 C -0.12231(13) 0.6479(4) 0.70987(12) 0.0192(3) Uani 1 1 d . H4 H -0.2007 0.5476 0.6670 0.023 Uiso 1 1 calc R C5 C -0.07712(13) 0.6780(4) 0.82584(13) 0.0200(3) Uani 1 1 d . H5 H -0.1244 0.5936 0.8626 0.024 Uiso 1 1 calc R C6 C 0.03613(13) 0.8297(4) 0.88900(12) 0.0194(3) Uani 1 1 d . H6 H 0.0664 0.8486 0.9686 0.023 Uiso 1 1 calc R H1 H 0.2399(19) 1.207(6) 0.8524(18) 0.037(6) Uiso 1 1 d . H2 H 0.093(2) 1.076(6) 0.599(2) 0.047(6) Uiso 1 1 d . H3 H -0.155(2) 0.628(6) 0.5084(19) 0.043(6) Uiso 1 1 d . O1 O 0.21586(9) 1.1117(3) 0.89780(8) 0.0190(3) Uani 1 1 d . O2 O 0.13553(9) 1.0370(3) 0.67041(8) 0.0190(3) Uani 1 1 d . O3 O -0.08691(10) 0.7427(3) 0.54288(8) 0.0234(3) 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 C1 0.0135(6) 0.0165(7) 0.0172(7) 0.0001(5) 0.0039(5) 0.0040(5) C2 0.0161(7) 0.0159(7) 0.0185(7) 0.0025(5) 0.0085(6) 0.0032(5) C3 0.0184(7) 0.0179(7) 0.0158(7) 0.0011(5) 0.0055(6) 0.0025(6) C4 0.0151(7) 0.0174(7) 0.0237(7) 0.0015(6) 0.0070(6) 0.0003(5) C5 0.0212(7) 0.0183(7) 0.0257(8) 0.0046(6) 0.0148(6) 0.0034(6) C6 0.0211(7) 0.0203(7) 0.0173(7) 0.0017(5) 0.0088(6) 0.0056(6) O1 0.0156(5) 0.0256(6) 0.0139(5) 0.0010(4) 0.0046(4) 0.0000(4) O2 0.0156(5) 0.0273(6) 0.0137(5) 0.0023(4) 0.0058(4) -0.0010(4) O3 0.0186(6) 0.0334(7) 0.0150(5) -0.0017(5) 0.0041(4) -0.0077(5) 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle O1 C1 C6 119.23(13) O1 C1 C2 120.36(13) C6 C1 C2 120.41(13) O2 C2 C3 122.54(13) O2 C2 C1 117.89(12) C3 C2 C1 119.57(13) O3 C3 C4 123.94(13) O3 C3 C2 115.63(13) C4 C3 C2 120.43(13) C5 C4 C3 119.24(13) C4 C5 C6 120.93(13) C1 C6 C5 119.39(13) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 O1 1.3766(17) C1 C6 1.384(2) C1 C2 1.388(2) C2 O2 1.3775(17) C2 C3 1.388(2) C3 O3 1.3721(17) C3 C4 1.387(2) C4 C5 1.384(2) C5 C6 1.385(2) _journal_paper_doi 10.1021/cg3003367