#============================================================================== data_global #============================================================================== # 0. AUDIT DETAILS _audit_creation_date 'Mar 26 10:47:19 2012' _audit_creation_method 'PLATON option' _audit_update_record ; ; #=============================================================================== # 1. SUBMISSION DETAILS _publ_contact_author_name ; Prof. Tayur N. Guru Row ; _publ_contact_author_address ; Solid State and Structural Chemistry Unit Indian Institute of Science C.V.Raman Avenue Bangalore 560 012 Karnataka India ; _publ_contact_author_email ssctng@sscu.iisc.ernet.in _publ_contact_author_fax '+31 30 2533940' _publ_contact_author_phone '+31 30 2532538' _publ_requested_journal 'Crystal Growth and Design' # Publication choise FI, CI or EI for Inorganic # FM, CM or EM for Metal-organic # FO, CO or EO for Organic _publ_requested_category ? _publ_requested_coeditor_name ? _publ_contact_letter # Include date of submission ; Date of submission ? Please consider this CIF submission for publication as a Regular Structural Paper in Acta Crystallographica C. ; #=============================================================================== # 2. PROCESSING SUMMARY (JOURNAL OFFICE ONLY) _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_date_printers_first ? _journal_date_printers_final ? _journal_date_proofs_out ? _journal_date_proofs_in ? _journal_coeditor_name ? _journal_coeditor_code ? _journal_coeditor_notes ; ; _journal_techeditor_code ? _journal_techeditor_notes ; ; _journal_coden_ASTM ? _journal_name_full ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? #=============================================================================== # 3. TITLE AND AUTHOR LIST _publ_section_title ; Title (type here to add) ; _publ_section_title_footnote . # The loop structure below should contain the names and adresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_address _publ_author_footnote _publ_author_email 'Row, Tayur N. Guru' ; Solid State and Structural Chemistry Unit Indian Institute of Science C.V.Raman Avenue Bangalore 560 012 Karnataka India ; ; # author related footnote ; . 'Kaur, Ramanpreet' ; Solid State and Structural Chemistry Unit Indian Institute of Science C.V.raman Avenue Bangalore 560 012 Karnataka India ; . . #=============================================================================== # 4. TEXT _publ_section_synopsis ; ? ; _publ_section_abstract ; ? ; # Insert blank lines between paragraphs _publ_section_comment ; ; _publ_section_exptl_prep ; ? ; _publ_section_exptl_refinement ; ? ; # Insert blank lines between references _publ_section_references ; Allen, F.H. (2002). Acta Cryst. B58, 380-388. Altomare, A., Burla, M.C., Camalli, M., Cascarano, G.L., Giacovazzo, C. Guagliardi, A., Moliterni, A.G.G., Polidori, G. & Spagna, R. (1999) J. Appl. Cryst. 32, 115-119. Beurskens, P.T., Beurskens, G., de Gelder, R., Garc\'ia-Granda, S., Gould, R.O., Israel, R. & Smits, J.M.M. (1999) The DIRDIF99 Program System, Technical Report of the Crystallography Laboratory, University of Nijmegen, The Netherlands. Boer, J.L. de & Duisenberg, A.J.M. (1984). Acta Cryst. A40, C-410. Boeyens, J.C.A. (1978). J.Cryst.Mol.Struct. 8, 317-320. Cremer, D. & Pople, J.A. (1975). J. Am. Chem. Soc. 97, 1354-1358. Duisenberg, A.J.M. (1992). J. Appl. Cryst. 25, 92-96. Duisenberg, A.J.M., Kroon-Batenburg, L.M.J. & Schreurs, A.M.M. (2003). J. Appl. Cryst. 36, 220-229. Enraf-Nonius (1989). CAD-4 Software. Version 5. Enraf-Nonius, Delft, The Netherlands. Flack, H.D. (1983). Acta Cryst. A39, 876-881. Hooft, R.W.W. (1998). Collect Software, Nonius B.V., Delft, The Netherlands. LePage, Y. (1987). J. Appl. Cryst. 20, 264-269. Mackay, A.L. (1984). Acta Cryst. A40, 165-166. Meulenaer, J. de & Tompa, H. (1965). Acta Cryst. 19, 1014-1018. North, A.C.T., Phillips, D.C. & Mathews, F.S. (1968). Acta Cryst. A24, 351-359. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C.W. Carter & R.M. Sweet, pp. 307-326. London: Academic Press. Sheldrick, G.M. (1986). SHELXS86. University of G\"ottingen, Germany. Sheldrick, G.M. (1993). SHELXL93. University of G\"ottingen, Germany. Sheldrick, G.M. (1997). SHELXS97. University of G\"ottingen, Germany. Sheldrick, G.M. (1997). SHELXL97. University of G\"ottingen, Germany. Sluis, P. van der & Spek, A.L. (1990). Acta Cryst. A46, 194-201. Spek, A.L. (1987). Acta Cryst. C43, 1233-1235. Spek, A.L. (1988). J. Appl. Cryst. 21, 578-579. Spek, A.L. (1994). Am. Crystallogr. Assoc.-Abstracts, 22, 66. Spek, A.L. (1997). HELENA, Program for Datareduction, Utrecht University, The Netherlands. Spek, A.L. (2003). J. Appl. Cryst. 36, 7-13. Wilson, A.J.C. (1992). Ed. International Tables for Crystallography, Volume C, Kluwer Academic Publishers, Dordrecht, The Netherlands. ; _publ_section_acknowledgements ; ; _publ_section_figure_captions ; View of the title compound with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level. ; #=============================================================================== data_final #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ; _chemical_name_common 'gallic acid monohydrate acetamide' _chemical_melting_point ? _chemical_formula_moiety 'C7 H6 O5, C2 H5 N O' # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_structural ? _chemical_formula_sum 'C9 H11 N O6' _chemical_formula_iupac ? _chemical_formula_weight 229.19 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 '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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 21/n' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 1/2-x,1/2+y,1/2-z 3 -x,-y,-z 4 1/2+x,1/2-y,1/2+z _cell_length_a 4.2630(2) _cell_length_b 22.5002(10) _cell_length_c 10.0489(3) _cell_angle_alpha 90 _cell_angle_beta 92.868(3) _cell_angle_gamma 90 _cell_volume 962.67(7) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 5890 _cell_measurement_theta_min 2.7 _cell_measurement_theta_max 25.0 _cell_special_details ; ; _exptl_crystal_description 'needle' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.581 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 480 _exptl_absorpt_coefficient_mu 0.135 _exptl_crystal_density_meas_temp ? # Permitted for _exptl_absorpt_correction_type : # analytical 'analytical from crystal shape' # Example: de Meulenaer&Tompa: ABST # cylinder 'cylindrical' # gaussian 'Gaussian from crystal shape' # Example: PLATON/ABSG # integration 'integration from crystal shape' # multi-scan 'symmetry-related measurements' # Example: SADABS, MULABS # none 'no absorption corr. applied' # numerical 'numerical from crystal shape' # psi-scan 'psi-scan corrections' # Example: PLATON/ABSP # refdelf 'refined from delta-F' # Example: SHELXA, # sphere 'spherical' # Example: PLATON/ABSS _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_process_details 'CrysAlis RED (Oxford Diffraction,2009)' _exptl_absorpt_correction_T_min 0.9709 _exptl_absorpt_correction_T_max 0.9761 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 110(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_probe 'x-ray' _diffrn_radiation_type 'MoK\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator 'graphite' _diffrn_measurement_device_type 'Oxford Xcalibur,Eos(Nova) CCD detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? # number of measured reflections (redundant set) _diffrn_reflns_number 5890 _diffrn_reflns_av_R_equivalents 0.0364 _diffrn_reflns_av_sigmaI/netI 0.0353 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.72 _diffrn_reflns_theta_max 24.99 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 1682 # number of observed reflections (> n sig(I)) _reflns_number_gt 1418 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'WinGX (Farrugia, 1999)' #=============================================================================== # 8. REFINEMENT DATA _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^)+(0.0491P)^2^+0.1682P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1682 _refine_ls_number_parameters 178 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0453 _refine_ls_R_factor_gt 0.0364 _refine_ls_wR_factor_ref 0.0991 _refine_ls_wR_factor_gt 0.0915 _refine_ls_goodness_of_fit_ref 1.090 _refine_ls_restrained_S_all 1.090 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.177 _refine_diff_density_min -0.268 _refine_diff_density_rms 0.052 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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 O3 O 0.3738(3) 0.17974(6) 0.63174(11) 0.0155(3) Uani 1 1 d . . . O4 O 0.6272(3) 0.24655(5) 0.83644(12) 0.0146(3) Uani 1 1 d . . . O2 O -0.3038(3) 0.02843(6) 0.85198(11) 0.0183(3) Uani 1 1 d . . . O5 O 0.4510(3) 0.22821(6) 1.09397(11) 0.0163(3) Uani 1 1 d . . . O1 O -0.2778(3) 0.05227(6) 1.06836(11) 0.0184(3) Uani 1 1 d . . . C2 C 0.0077(3) 0.11084(8) 0.91827(15) 0.0138(4) Uani 1 1 d . . . O6 O 0.4687(3) 0.07912(6) 0.51520(12) 0.0267(4) Uani 1 1 d . . . C5 C 0.4170(4) 0.20267(8) 0.85996(15) 0.0130(4) Uani 1 1 d . . . C7 C 0.0826(4) 0.12104(8) 0.78657(16) 0.0136(4) Uani 1 1 d . . . C6 C 0.2868(4) 0.16652(7) 0.75827(16) 0.0127(4) Uani 1 1 d . . . C3 C 0.1310(4) 0.14775(8) 1.01987(16) 0.0141(4) Uani 1 1 d . . . C4 C 0.3330(4) 0.19334(8) 0.99081(15) 0.0132(4) Uani 1 1 d . . . C1 C -0.2026(4) 0.06207(8) 0.95387(16) 0.0139(4) Uani 1 1 d . . . N1 N 0.7434(4) 0.02982(8) 0.36633(15) 0.0212(4) Uani 1 1 d . . . C8 C 0.7291(5) 0.13698(9) 0.35511(19) 0.0271(5) Uani 1 1 d . . . H8A H 0.6260 0.1699 0.3993 0.041 Uiso 1 1 calc R . . H8B H 0.6630 0.1366 0.2603 0.041 Uiso 1 1 calc R . . H8C H 0.9575 0.1420 0.3648 0.041 Uiso 1 1 calc R . . C9 C 0.6392(4) 0.07974(8) 0.41731(16) 0.0171(4) Uani 1 1 d . . . H3 H 0.075(4) 0.1424(8) 1.1116(19) 0.014(4) Uiso 1 1 d . . . H7 H -0.005(4) 0.0980(9) 0.7152(19) 0.019(5) Uiso 1 1 d . . . H1A H 0.677(4) -0.0053(10) 0.401(2) 0.023(5) Uiso 1 1 d . . . H1B H 0.852(5) 0.0322(10) 0.296(2) 0.034(6) Uiso 1 1 d . . . H2O H -0.442(7) -0.0001(13) 0.884(3) 0.062(8) Uiso 1 1 d . . . H4O H 0.687(5) 0.2449(11) 0.757(3) 0.044(7) Uiso 1 1 d . . . H5O H 0.577(6) 0.2547(11) 1.069(2) 0.040(7) Uiso 1 1 d . . . H3O H 0.404(6) 0.1447(12) 0.585(3) 0.052(7) Uiso 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 O3 0.0222(6) 0.0139(7) 0.0108(6) 0.0002(5) 0.0040(4) 0.0003(5) O4 0.0165(6) 0.0138(7) 0.0137(6) 0.0007(5) 0.0040(4) -0.0020(5) O2 0.0207(7) 0.0176(7) 0.0165(6) -0.0011(5) 0.0005(5) -0.0056(5) O5 0.0194(7) 0.0168(7) 0.0129(6) -0.0023(5) 0.0017(5) -0.0050(5) O1 0.0197(7) 0.0196(8) 0.0159(6) 0.0029(5) 0.0019(5) -0.0041(5) C2 0.0093(8) 0.0150(10) 0.0170(8) 0.0017(7) 0.0013(6) 0.0033(7) O6 0.0441(8) 0.0163(8) 0.0212(7) -0.0010(5) 0.0168(6) -0.0031(6) C5 0.0114(8) 0.0113(9) 0.0164(8) 0.0010(7) 0.0014(6) 0.0031(7) C7 0.0135(8) 0.0131(9) 0.0143(8) -0.0018(7) -0.0001(6) 0.0031(7) C6 0.0129(8) 0.0125(9) 0.0129(8) 0.0026(7) 0.0027(6) 0.0055(7) C3 0.0122(8) 0.0162(10) 0.0142(9) 0.0016(7) 0.0020(6) 0.0030(7) C4 0.0117(8) 0.0131(10) 0.0146(8) -0.0014(7) -0.0004(6) 0.0035(7) C1 0.0121(8) 0.0134(10) 0.0162(8) 0.0004(7) 0.0000(6) 0.0035(7) N1 0.0312(9) 0.0158(10) 0.0173(8) -0.0011(7) 0.0089(6) -0.0046(7) C8 0.0405(11) 0.0174(11) 0.0247(10) -0.0008(8) 0.0145(8) -0.0029(9) C9 0.0199(9) 0.0181(10) 0.0132(8) -0.0013(7) -0.0009(6) -0.0030(8) #=============================================================================== # 10. MOLECULAR GEOMETRY _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 O3 C6 1.375(2) . ? O3 H3O 0.93(3) . ? O4 C5 1.362(2) . ? O4 H4O 0.85(3) . ? O2 C1 1.328(2) . ? O2 H2O 0.94(3) . ? O5 C4 1.375(2) . ? O5 H5O 0.85(3) . ? O1 C1 1.230(2) . ? C2 C7 1.396(2) . ? C2 C3 1.398(2) . ? C2 C1 1.472(2) . ? O6 C9 1.252(2) . ? C5 C4 1.396(2) . ? C5 C6 1.399(2) . ? C7 C6 1.382(2) . ? C7 H7 0.95(2) . ? C3 C4 1.380(3) . ? C3 H3 0.971(19) . ? N1 C9 1.321(2) . ? N1 H1A 0.91(2) . ? N1 H1B 0.86(2) . ? C8 C9 1.490(3) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? 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 C6 O3 H3O 109.7(16) . . ? C5 O4 H4O 111.2(16) . . ? C1 O2 H2O 108.1(17) . . ? C4 O5 H5O 112.7(16) . . ? C7 C2 C3 119.94(16) . . ? C7 C2 C1 121.60(15) . . ? C3 C2 C1 118.46(15) . . ? O4 C5 C4 118.32(14) . . ? O4 C5 C6 122.35(14) . . ? C4 C5 C6 119.32(16) . . ? C6 C7 C2 119.55(15) . . ? C6 C7 H7 118.6(11) . . ? C2 C7 H7 121.9(11) . . ? O3 C6 C7 123.52(15) . . ? O3 C6 C5 115.74(15) . . ? C7 C6 C5 120.73(15) . . ? C4 C3 C2 120.19(15) . . ? C4 C3 H3 118.6(11) . . ? C2 C3 H3 121.2(11) . . ? O5 C4 C3 118.24(14) . . ? O5 C4 C5 121.53(15) . . ? C3 C4 C5 120.22(15) . . ? O1 C1 O2 121.95(16) . . ? O1 C1 C2 123.47(15) . . ? O2 C1 C2 114.57(14) . . ? C9 N1 H1A 118.2(13) . . ? C9 N1 H1B 117.9(15) . . ? H1A N1 H1B 123(2) . . ? C9 C8 H8A 109.5 . . ? C9 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C9 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? O6 C9 N1 121.00(17) . . ? O6 C9 C8 120.72(16) . . ? N1 C9 C8 118.28(16) . . ? 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_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 C2 C7 C6 2.1(2) . . . . ? C1 C2 C7 C6 -178.52(15) . . . . ? C2 C7 C6 O3 179.98(14) . . . . ? C2 C7 C6 C5 -0.5(2) . . . . ? O4 C5 C6 O3 -2.8(2) . . . . ? C4 C5 C6 O3 178.06(14) . . . . ? O4 C5 C6 C7 177.69(14) . . . . ? C4 C5 C6 C7 -1.5(2) . . . . ? C7 C2 C3 C4 -1.6(2) . . . . ? C1 C2 C3 C4 178.93(14) . . . . ? C2 C3 C4 O5 -179.41(14) . . . . ? C2 C3 C4 C5 -0.4(2) . . . . ? O4 C5 C4 O5 1.7(2) . . . . ? C6 C5 C4 O5 -179.07(14) . . . . ? O4 C5 C4 C3 -177.28(14) . . . . ? C6 C5 C4 C3 1.9(2) . . . . ? C7 C2 C1 O1 -178.84(15) . . . . ? C3 C2 C1 O1 0.6(2) . . . . ? C7 C2 C1 O2 1.9(2) . . . . ? C3 C2 C1 O2 -178.65(14) . . . . ? #===END