# Copyright The Royal Society of Chemistry, 1999 # CCDC Number: 188/159 # CIF-file generated for C14H11NO3 CP389 #============================================================================== data_global #============================================================================== # 0. AUDIT DETAILS _audit_creation_date 1998-07-06 _audit_creation_method 'PLATON option' _audit_update_record ; ? ; #=============================================================================== # 1. SUBMISSION DETAILS # Name and address of author for correspondence _publ_contact_author_name ; Drs. A. Meetsma ; _publ_contact_author_address ; Crystal Structure Center, Chemical Physics, Materials Science Center, Groningen University, Nijenborgh 4, NL-9747 AG Groningen, The Netherlands. ; _publ_contact_author_email A.Meetsma@fwn.rug.nl _publ_contact_author_fax '+31 50 3634441' _publ_contact_author_phone '+31 50 3634368' _publ_requested_journal 'J. Chem.Soc., Perkin Trans. 2' # Publication choice FI FM FO CI CM CO AD _publ_requested_category ? _publ_requested_coeditor_name ? _publ_contact_letter # Include date of submission ; Date of first submission : 1998-07-06 Date of second submission : 1998-12-03 (Now included with a low temperatue (130 K) structure) Consider this CIF submission for depostion of the Xray-structure of a manuscript to be submitted to : J. Chem.Soc., Perkin Trans. 2 Your paper code :: 8105506h Perkin2 (Our Code : CP389) Title of manuscript :: Hydrogen bonding properties of N-(2-carboxyphenyl)salicylidenimine Authors : Alette G.J. Ligtenbarg, Ronald Hage, Auke Meetsma, Ben L. Feringa ; #=============================================================================== # 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 ; ? ; _publ_section_title_footnote ; ? ; # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_address 'Meetsma, Auke' ; Crystal Structure Center, Chemical Physics, Materials Science Center, Groningen University, Nijenborgh 4, NL-9747 AG Groningen, The Netherlands. ; #=============================================================================== # 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 ; Boer, J.L. de & Duisenberg, A.J.M. (1984). Acta Cryst. A40, C-410. Duisenberg, A.J.M. (1992). J. Appl. Cryst. 25, 92-96. Enraf-Nonius (1994). CAD4-UNIX Software. Version 5.1 Utrecht modified version October 1994. Enraf-Nonius, Delft, Scientific Instuments Division, Delft, The Netherlands. International Tables for Crystallography (1983). Vol. A. Space-group symmetry, edited by T. Hahn. Dordrecht: Reidel. (Present distributor Kluwer Academic Publishers, Dordrecht). International Tables for Crystallography (1992). Vol. C. Edited by A.J.C Wilson, Kluwer Academic Publishers, Dordrecht, The Netherlands. Le Page, Y. (1987). J. Appl. Cryst. 20, 264-269. Le Page, Y. (1988). J. Appl. Cryst. 21, 983-984. Meetsma, A. (1996). Extended version of the program PLUTO. Groningen University, The Netherlands. (unpublished). Motherwell, W.D.S & Clegg, W. (1978). PLUTO. Program for plotting molecular and crystal structures. Univ. of Cambridge, England. (unpublished). Sheldrick, G.M. SHELXS86. Program for Crystal Structure solution. University of G\\"ottingen, Germany, 1986. Sheldrick, G.M. SHELXS93. Program for Crystal Structure solution. University of G\\"ottingen, Germany, 1993. Spek, A.L. (1990). Acta Cryst. A46, C-34. Spek, A.L. (1997). HELENA, Program for Datareduction, Utrecht University, The Netherlands. Spek, A.L. (1994). Am. Crystallogr. Assoc.-Abstracts, 22, 66. ; _publ_section_figure_captions ; ? ; _publ_section_acknowledgements ; ? ; #=============================================================================== data_c14h11no #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H11 N O3' _chemical_formula_structural ? # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_sum 'C14 H11 N O3' _chemical_formula_weight 241.25 _chemical_compound_source 'by syntheses' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C .0033 .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 '-I 2ya' _symmetry_space_group_name_H-M 'I 2/a' loop_ _symmetry_equiv_pos_as_xyz x,y,z 1/2-x,y,-z -x,-y,-z 1/2+x,-y,z 1/2+x,1/2+y,1/2+z -x,1/2+y,1/2-z 1/2-x,1/2-y,1/2-z x,1/2-y,1/2+z _cell_length_a 14.840(1) _cell_length_b 6.813(1) _cell_length_c 22.680(1) _cell_angle_alpha 90 _cell_angle_beta 97.796(6) _cell_angle_gamma 90 _cell_volume 2271.9(4) _cell_formula_units_Z 8 _cell_measurement_temperature 295 _cell_measurement_reflns_used 22 _cell_measurement_theta_min 17.14 _cell_measurement_theta_max 20.82 _cell_special_details ; Unit cell parameters (Duisenberg, 1992) and orientation matrix were determined from a least-squares treatment of SET4 (de Boer & Duisenberg, 1984) setting. Reduced cell calculations did not indicate any higher metric lattice symmetry and examination of the final atomic coordinates of the structure did not yield extra symmetry elements (Spek, 1988; Le Page 1987, 1988) ; _exptl_crystal_description 'block-shaped' _exptl_crystal_colour 'orange-red' _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.5 _exptl_crystal_size_rad ? _exptl_crystal_density_meas 'Not Measured' _exptl_crystal_density_diffrn 1.411 _exptl_crystal_density_method ? _exptl_crystal_F_000 1008 _exptl_absorpt_coefficient_mu .10 _exptl_crystal_density_meas_temp 295 _exptl_absorpt_correction_type ? _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ? ; _diffrn_ambient_temperature 295 _diffrn_radiation_wavelength .71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'fine focus sealed Philips Mo tube ' _diffrn_radiation_monochromator 'perpendicular mounted graphite' _diffrn_radiation_detector ; scintillation NaI crystal with photomultiplier ; _diffrn_measurement_device_type ; Enraf Nonius CAD-4F diffractometer ; _diffrn_measurement_method '\w/2\q' _diffrn_special_details ; Enraf-Nonius CAD-4F diffractometer. Graphite-monochromated Mo K\a radiation, \w/2\q scan, \D\w = (0.85 + 0.34 tg \q)\%. ; _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 180 _diffrn_standards_decay_% 8.6 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -4 0 0 -4 -4 0 -2 0 6 # number of measured reflections (redundant set) _diffrn_reflns_number 2484 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0120 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 26.98 _diffrn_reflns_reduction_process ; Intensity data were corrected for Lorentz and polarization effects, scale variation, but not for absorption and reduced to F~o~^2^ ; # number of unique reflections _reflns_number_total 2484 _reflns_number_gt 1966 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4-UNIX Software Version 5.1, 1994' _computing_cell_refinement 'SET4 (de Boer & Duisenberg, 1984)' _computing_data_reduction 'HELENA (Spek, 1993)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ; PLUTO (Meetsma, 1997) ORTEP (Burnett et al., 1996) PLATON (Spek, 1994, 1996) ; _computing_publication_material 'PLATON (Spek, 1990)' #=============================================================================== # 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 w=1/[\s^2^(Fo^2^)+(0.0777P)^2^+0.2129P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment isotropic _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0055(9) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2484 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0500 _refine_ls_R_factor_gt 0.0388 _refine_ls_wR_factor_ref 0.1154 _refine_ls_wR_factor_gt 0.1102 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max .220 _refine_diff_density_min -.179 _refine_diff_density_rms .042 #=============================================================================== # 9. ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv O1 Uani .12921(6) .78696(15) -.01568(4) 1.000 .0454(3) O2 Uani .26694(6) .80769(17) .09099(4) 1.000 .0527(3) O3 Uani .34029(7) 1.0562(2) .13964(5) 1.000 .0674(4) N1 Uani .08849(7) .83251(15) .09386(4) 1.000 .0350(3) C1 Uani .04320(8) .74689(18) -.03407(5) 1.000 .0356(3) C2 Uani .01094(10) .6974(2) -.09332(6) 1.000 .0443(4) C3 Uani -.07955(11) .6571(2) -.10989(6) 1.000 .0492(4) C4 Uani -.14186(10) .6656(2) -.06934(7) 1.000 .0514(4) C5 Uani -.11250(9) .7167(2) -.01185(6) 1.000 .0453(4) C6 Uani -.01997(8) .75670(18) .00749(5) 1.000 .0357(3) C7 Uani .00554(8) .80782(18) .06811(5) 1.000 .0364(3) C8 Uani .11521(8) .88493(18) .15454(5) 1.000 .0355(3) C9 Uani .05234(9) .8893(2) .19481(6) 1.000 .0480(4) C10 Uani .07955(11) .9493(3) .25240(6) 1.000 .0577(5) C11 Uani .16761(12) 1.0044(3) .27080(6) 1.000 .0591(5) C12 Uani .22986(11) 1.0010(2) .23076(6) 1.000 .0502(5) C13 Uani .20539(8) .94030(19) .17252(5) 1.000 .0381(4) C14 Uani .27762(8) .9385(2) .13150(5) 1.000 .0415(4) H1 Uiso .1731(14) .803(3) -.0516(8) 1.000 .086(6) H1' Uiso .1388(12) .818(2) .0709(8) 1.000 .061(5) H2 Uiso .0558(11) .692(2) -.1217(7) 1.000 .054(4) H3 Uiso -.1024(13) .620(3) -.1514(9) 1.000 .070(5) H4 Uiso -.2032(14) .641(3) -.0813(9) 1.000 .074(5) H5 Uiso -.1544(11) .725(2) .0199(8) 1.000 .057(4) H7 Uiso -.0442(10) .826(2) .0914(7) 1.000 .050(4) H9 Uiso -.0072(13) .851(3) .1826(8) 1.000 .061(5) H10 Uiso .0332(12) .945(3) .2810(8) 1.000 .071(5) H11 Uiso .1876(13) 1.046(3) .3090(10) 1.000 .079(6) H12 Uiso .2884(13) 1.034(3) .2420(8) 1.000 .065(5) 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 O1 .0334(5) .0687(6) .0352(5) -.0002(4) .0081(3) -.0067(4) O2 .0361(5) .0801(7) .0439(5) -.0143(5) .0130(4) -.0059(5) O3 .0428(6) .0910(9) .0713(7) -.0196(6) .0184(5) -.0223(6) N1 .0309(5) .0411(6) .0339(5) .0019(4) .0077(4) -.0003(4) C1 .0352(6) .0364(6) .0348(6) .0034(5) .0037(5) -.0016(5) C2 .0482(8) .0457(7) .0385(7) -.0004(5) .0044(6) -.0017(6) C3 .0542(8) .0474(8) .0426(7) -.0019(6) -.0055(6) -.0035(6) C4 .0390(7) .0545(8) .0573(8) .0014(7) -.0062(6) -.0066(6) C5 .0347(7) .0511(8) .0499(7) .0039(6) .0047(6) -.0038(6) C6 .0330(6) .0362(6) .0379(6) .0037(5) .0048(5) -.0020(5) C7 .0321(6) .0396(6) .0388(6) .0043(5) .0091(5) -.0006(5) C8 .0349(6) .0400(6) .0321(6) .0040(5) .0065(5) .0023(5) C9 .0389(7) .0680(9) .0389(7) .0074(6) .0117(6) .0016(6) C10 .0540(8) .0843(11) .0381(7) .0034(7) .0178(6) .0073(8) C11 .0648(10) .0800(11) .0330(7) -.0078(7) .0086(6) .0028(9) C12 .0452(8) .0640(9) .0406(7) -.0042(6) .0024(6) -.0023(7) C13 .0366(6) .0419(7) .0364(6) .0011(5) .0071(5) .0019(5) C14 .0296(6) .0573(8) .0374(6) -.0002(6) .0036(5) -.0013(5) #=============================================================================== # 10. MOLECULAR GEOMETRY _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All esds are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.3165(15) . . yes O2 C14 1.2744(16) . . yes O3 C14 1.2229(18) . . yes O1 H1 1.115(19) . . no N1 C7 1.2999(16) . . yes N1 C8 1.4250(15) . . yes N1 H1' .972(18) . . no C1 C2 1.4050(18) . . no C1 C6 1.4183(17) . . no C2 C3 1.372(2) . . no C3 C4 1.391(2) . . no C4 C5 1.363(2) . . no C5 C6 1.4102(18) . . no C6 C7 1.4190(16) . . no C8 C13 1.3970(17) . . no C8 C9 1.3917(18) . . no C9 C10 1.376(2) . . no C10 C11 1.369(2) . . no C11 C12 1.381(2) . . no C12 C13 1.3847(18) . . no C13 C14 1.5117(17) . . no C2 H2 .987(16) . . no C3 H3 .99(2) . . no C4 H4 .93(2) . . no C5 H5 1.015(17) . . no C7 H7 .972(15) . . no C9 H9 .927(19) . . no C10 H10 1.008(18) . . no C11 H11 .92(2) . . no C12 H12 .900(19) . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 H1 115.2(10) . . . no C7 N1 C8 126.07(10) . . . yes C7 N1 H1' 119.7(11) . . . no C8 N1 H1' 114.2(11) . . . no O1 C1 C2 122.87(11) . . . yes O1 C1 C6 118.65(10) . . . yes C2 C1 C6 118.47(11) . . . no C1 C2 C3 120.25(13) . . . no C2 C3 C4 121.61(13) . . . no C3 C4 C5 119.23(14) . . . no C4 C5 C6 121.23(12) . . . no C1 C6 C5 119.19(11) . . . no C1 C6 C7 122.82(11) . . . no C5 C6 C7 117.99(11) . . . no N1 C7 C6 125.38(11) . . . yes C9 C8 C13 120.24(11) . . . no N1 C8 C13 118.66(10) . . . yes N1 C8 C9 121.04(11) . . . yes C8 C9 C10 119.53(13) . . . no C9 C10 C11 121.05(14) . . . no C10 C11 C12 119.41(13) . . . no C11 C12 C13 121.34(14) . . . no C12 C13 C14 118.25(11) . . . no C8 C13 C12 118.42(12) . . . no C8 C13 C14 123.32(10) . . . no O2 C14 O3 125.81(12) . . . yes O2 C14 C13 114.84(11) . . . yes O3 C14 C13 119.34(11) . . . yes C1 C2 H2 117.4(9) . . . no C3 C2 H2 122.4(9) . . . no C2 C3 H3 120.5(11) . . . no C4 C3 H3 117.8(11) . . . no C3 C4 H4 120.8(13) . . . no C5 C4 H4 119.9(13) . . . no C4 C5 H5 123.1(10) . . . no C6 C5 H5 115.7(10) . . . no N1 C7 H7 118.8(9) . . . no C6 C7 H7 115.8(9) . . . no C8 C9 H9 119.6(11) . . . no C10 C9 H9 120.8(11) . . . no C9 C10 H10 117.7(11) . . . no C11 C10 H10 121.2(10) . . . no C10 C11 H11 122.9(12) . . . no C12 C11 H11 117.7(12) . . . no C11 C12 H12 121.0(12) . . . no C13 C12 H12 117.6(12) . . . no 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 C7 N1 C8 C13 -168.51(12) . . . . no C7 N1 C8 C9 8.80(19) . . . . no C8 N1 C7 C6 179.61(11) . . . . no C2 C1 C6 C5 .00(18) . . . . no C2 C1 C6 C7 -179.16(12) . . . . no O1 C1 C2 C3 -179.98(12) . . . . no C6 C1 C2 C3 -.90(19) . . . . no O1 C1 C6 C5 179.15(12) . . . . no O1 C1 C6 C7 -.03(18) . . . . no C1 C2 C3 C4 .6(2) . . . . no C2 C3 C4 C5 .5(2) . . . . no C3 C4 C5 C6 -1.4(2) . . . . no C4 C5 C6 C1 1.2(2) . . . . no C4 C5 C6 C7 -179.62(12) . . . . no C1 C6 C7 N1 -7.0(2) . . . . no C5 C6 C7 N1 173.85(12) . . . . no N1 C8 C13 C12 176.65(11) . . . . no N1 C8 C9 C10 -177.01(14) . . . . no C13 C8 C9 C10 .3(2) . . . . no C9 C8 C13 C14 179.69(12) . . . . no N1 C8 C13 C14 -2.97(18) . . . . no C9 C8 C13 C12 -.68(19) . . . . no C8 C9 C10 C11 -.2(3) . . . . no C9 C10 C11 C12 .5(3) . . . . no C10 C11 C12 C13 -.9(3) . . . . no C11 C12 C13 C8 1.0(2) . . . . no C11 C12 C13 C14 -179.33(14) . . . . no C8 C13 C14 O2 -30.90(18) . . . . no C8 C13 C14 O3 149.99(13) . . . . no C12 C13 C14 O2 149.48(12) . . . . no C12 C13 C14 O3 -29.63(19) . . . . no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O1 O2 2.9511(13) . . no O1 N1 2.6535(13) . . no O1 O2 2.4549(13) . 2_555 no O1 C14 3.2959(16) . 2_555 no O2 C1 3.2808(16) . 2_555 no O2 O1 2.9511(13) . . no O2 N1 2.6632(14) . . no O2 C2 3.3742(18) . 2_555 no O2 O1 2.4549(13) . 2_555 no O3 C9 3.2462(18) . 4_575 no O3 C7 3.2532(17) . 4_575 no O1 H1' 1.961(18) . . no O2 H1 1.34(2) . 2_555 no O2 H1' 1.896(18) . . no O2 H2 2.744(16) . 2_555 no O3 H1 2.626(19) . 2_555 no O3 H12 2.548(18) . . no O3 H7 2.300(15) . 4_575 no O3 H9 2.423(19) . 4_575 no N1 O1 2.6535(13) . . no N1 O2 2.6632(14) . . no N1 C3 3.3600(18) . 3_565 no C1 C6 3.5086(18) . 3_565 no C1 O2 3.2807(16) . 2_555 no C1 C5 3.4391(19) . 3_565 no C1 C6 3.4608(18) . 3_575 no C1 C7 3.1893(18) . 3_575 no C2 C7 3.5032(19) . 3_565 no C2 O2 3.3742(18) . 2_555 no C2 C7 3.4333(19) . 3_575 no C2 C8 3.5812(19) . 3_575 no C3 C13 3.508(2) . 3_575 no C3 C8 3.3008(19) . 3_575 no C3 N1 3.3600(18) . 3_565 no C3 C7 3.4431(19) . 3_565 no C4 C14 3.543(2) . 3_575 no C5 C1 3.4391(19) . 3_565 no C6 C1 3.4608(18) . 3_575 no C6 C1 3.5086(18) . 3_565 no C6 C6 3.3929(18) . 3_575 no C6 C7 3.4479(18) . 3_575 no C6 C6 3.5715(18) . 3_565 no C7 C2 3.4333(19) . 3_575 no C7 C2 3.5032(19) . 3_565 no C7 O3 3.2532(17) . 4_475 no C7 C1 3.1893(18) . 3_575 no C7 C6 3.4479(18) . 3_575 no C7 C3 3.4431(19) . 3_565 no C8 C2 3.5812(19) . 3_575 no C8 C3 3.3008(19) . 3_575 no C9 O3 3.2462(18) . 4_475 no C12 C12 3.534(2) . 7_575 no C12 C12 3.560(2) . 7_565 no C13 C3 3.508(2) . 3_575 no C14 O1 3.2959(16) . 2_555 no C14 C4 3.543(2) . 3_575 no C1 H1' 2.646(18) . . no C2 H10 3.071(18) . 8_564 no C7 H9 2.645(18) . . no C9 H7 2.613(16) . . no C10 H2 3.079(16) . 8_565 no C14 H1' 2.457(18) . . no C14 H1 2.243(19) . 2_555 no C14 H2 3.022(16) . 2_555 no H1 H2 2.32(3) . . no H1 O2 1.34(2) . 2_555 no H1 O3 2.626(19) . 2_555 no H1 C14 2.243(19) . 2_555 no H1' O1 1.961(18) . . no H1' O2 1.896(18) . . no H1' C1 2.646(18) . . no H1' C14 2.457(18) . . no H2 H1 2.32(3) . . no H2 O2 2.744(16) . 2_555 no H2 C14 3.022(16) . 2_555 no H2 C10 3.079(16) . 8_564 no H2 H10 2.38(2) . 8_564 no H5 H7 2.25(2) . . no H7 C9 2.613(16) . . no H7 H5 2.25(2) . . no H7 H9 2.07(2) . . no H7 O3 2.300(15) . 4_475 no H9 C7 2.645(18) . . no H9 H7 2.07(2) . . no H9 O3 2.423(19) . 4_475 no H10 C2 3.071(18) . 8_565 no H10 H2 2.38(2) . 8_565 no H12 O3 2.548(18) . . no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # O1 H1 O2 1.115(19) 1.34(2) 2.4549(13) 173.1(19) 2_555 yes N1 H1' O1 .972(18) 1.961(18) 2.6535(13) 126.2(14) . yes N1 H1' O2 .972(18) 1.896(18) 2.6632(14) 133.9(15) . yes C7 H7 O3 .972(15) 2.300(15) 3.2532(17) 166.6(12) 4_475 yes C9 H9 O3 .927(19) 2.423(19) 3.2462(18) 147.9(17) 4_475 yes # End of Crystallographic Information File # === END # CIF-file generated for C14H11NO3 CP389B data_c14h11no2 #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H11 N O3' _chemical_formula_structural ? # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_sum 'C14 H11 N O3' _chemical_formula_weight 241.25 _chemical_compound_source 'by syntheses' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C .0033 .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 '-I 2ya' _symmetry_space_group_name_H-M 'I 2/a' loop_ _symmetry_equiv_pos_as_xyz x,y,z 1/2-x,y,-z -x,-y,-z 1/2+x,-y,z 1/2+x,1/2+y,1/2+z -x,1/2+y,1/2-z 1/2-x,1/2-y,1/2-z x,1/2-y,1/2+z _cell_length_a 14.831(1) _cell_length_b 6.718(1) _cell_length_c 22.660(5) _cell_angle_alpha 90 _cell_angle_beta 97.610(5) _cell_angle_gamma 90 _cell_volume 2237.8(6) _cell_formula_units_Z 8 _cell_measurement_temperature 130 _cell_measurement_reflns_used 22 _cell_measurement_theta_min 16.63 _cell_measurement_theta_max 21.46 _cell_special_details ; Unit cell parameters (Duisenberg, 1992) and orientation matrix were determined from a least-squares treatment of SET4 (de Boer & Duisenberg, 1984) setting. Reduced cell calculations did not indicate any higher metric lattice symmetry and examination of the final atomic coordinates of the structure did not yield extra symmetry elements (Spek, 1988; Le Page 1987, 1988) ; _exptl_crystal_description 'block-shaped' _exptl_crystal_colour 'oranje-red' _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_size_rad ? _exptl_crystal_density_meas 'Not Measured' _exptl_crystal_density_diffrn 1.432 _exptl_crystal_density_method ? _exptl_crystal_F_000 1008 _exptl_absorpt_coefficient_mu .10 _exptl_crystal_density_meas_temp ? _exptl_absorpt_correction_type ' none' _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ? ; _diffrn_ambient_temperature 130 _diffrn_radiation_wavelength .71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'fine focus sealed Philips Mo tube ' _diffrn_radiation_monochromator 'perpendicular mounted graphite' _diffrn_radiation_detector ; scintillation NaI crystal with photomultiplier ; _diffrn_measurement_device_type ; Enraf Nonius CAD-4F diffractometer ; _diffrn_measurement_method '\w/2\q' _diffrn_special_details ; Crystal into the cold nitrogen stream of the low-temperature unit (Bolhuis, 1971), on an Enraf-Nonius CAD-4F diffractometer. Graphite-monochromated Mo K\a radiation, \w/2\q scan, \D\w = (0.80 + 0.34 tg \q)\%. ; _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 180 _diffrn_standards_decay_% 0.2 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -3 2 -1 4 0 -2 -2 -1 -3 # number of measured reflections (redundant set) _diffrn_reflns_number 2484 _diffrn_reflns_av_R_equivalents 0.0061 _diffrn_reflns_av_sigmaI/netI 0.0186 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.55 _diffrn_reflns_theta_max 26.00 _diffrn_reflns_reduction_process ; Intensity data were corrected for Lorentz and polarization effects, scale variation, but not for absorption and reduced to F~o~^2^ ; # number of unique reflections _reflns_number_total 2192 _reflns_number_gt 1783 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4-UNIX Software Version 5.1, 1994' _computing_cell_refinement 'SET4 (de Boer & Duisenberg, 1984)' _computing_data_reduction 'HELENA (Spek, 1993)' _computing_structure_solution ; The coordinates of the room-temperature structure were used as starting positions of the refinement ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; PLUTO (Meetsma, 1997) ORTEP (Burnett et al., 1996) PLATON (Spek, 1994, 1996) ; _computing_publication_material 'PLATON (Spek, 1990)' #=============================================================================== # 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 w=1/[\s^2^(Fo^2^)+(0.0636P)^2^+0.3190P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment isotropic _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2192 _refine_ls_number_parameters 207 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0482 _refine_ls_R_factor_gt 0.0359 _refine_ls_wR_factor_ref 0.1001 _refine_ls_wR_factor_gt 0.0951 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max .214 _refine_diff_density_min -.256 _refine_diff_density_rms .049 #=============================================================================== # 9. ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv O1 Uani .12980(6) .78538(15) -.01551(4) 1.000 .0248(3) O2 Uani .26662(6) .80206(15) .09128(4) 1.000 .0280(3) O3 Uani .33983(7) 1.05781(17) .13936(5) 1.000 .0346(3) N1 Uani .08788(8) .83165(16) .09402(5) 1.000 .0200(3) C1 Uani .04360(9) .74642(18) -.03433(6) 1.000 .0202(4) C2 Uani .01177(10) .6979(2) -.09385(6) 1.000 .0247(4) C3 Uani -.07892(10) .6580(2) -.11074(6) 1.000 .0268(4) C4 Uani -.14234(10) .6674(2) -.07030(6) 1.000 .0280(4) C5 Uani -.11313(10) .7184(2) -.01226(6) 1.000 .0251(4) C6 Uani -.02015(9) .75678(19) .00711(6) 1.000 .0202(4) C7 Uani .00482(9) .80837(19) .06808(6) 1.000 .0208(4) C8 Uani .11423(9) .88418(19) .15485(5) 1.000 .0198(4) C9 Uani .05096(10) .8894(2) .19506(6) 1.000 .0265(4) C10 Uani .07777(10) .9499(2) .25296(6) 1.000 .0313(5) C11 Uani .16672(11) 1.0065(2) .27150(6) 1.000 .0313(5) C12 Uani .22920(10) 1.0016(2) .23128(6) 1.000 .0275(4) C13 Uani .20474(9) .9394(2) .17287(6) 1.000 .0215(4) C14 Uani .27718(9) .9368(2) .13160(6) 1.000 .0234(4) H1 Uiso .1731(14) .801(3) -.0511(9) 1.000 .067(7) H1' Uiso .1348(12) .813(3) .0699(8) 1.000 .041(5) H2 Uiso .0572(11) .695(2) -.1231(7) 1.000 .031(4) H3 Uiso -.1012(11) .620(2) -.1522(7) 1.000 .033(4) H4 Uiso -.2039(13) .637(3) -.0824(8) 1.000 .042(5) H5 Uiso -.1556(12) .725(3) .0185(8) 1.000 .037(4) H7 Uiso -.0467(11) .826(2) .0917(7) 1.000 .036(4) H9 Uiso -.0093(13) .855(3) .1822(8) 1.000 .041(5) H10 Uiso .0309(11) .952(3) .2805(7) 1.000 .035(4) H11 Uiso .1864(11) 1.053(2) .3110(8) 1.000 .035(4) H12 Uiso .2899(12) 1.039(2) .2435(7) 1.000 .032(4) 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 O1 .0184(5) .0354(6) .0209(5) .0005(4) .0034(4) -.0034(4) O2 .0206(5) .0399(6) .0243(5) -.0068(4) .0061(4) -.0026(4) O3 .0228(5) .0445(7) .0376(6) -.0085(5) .0084(4) -.0102(5) N1 .0178(6) .0226(6) .0198(5) .0016(5) .0035(4) .0004(5) C1 .0197(7) .0179(6) .0225(6) .0030(5) .0007(5) -.0010(5) C2 .0269(7) .0239(7) .0232(7) -.0003(5) .0026(6) -.0001(6) C3 .0310(8) .0236(7) .0241(7) -.0010(6) -.0031(6) -.0012(6) C4 .0227(7) .0277(8) .0319(8) .0009(6) -.0026(6) -.0035(6) C5 .0208(7) .0260(7) .0286(7) .0038(6) .0031(6) -.0017(6) C6 .0202(7) .0182(6) .0224(6) .0021(5) .0033(5) -.0001(5) C7 .0189(6) .0202(7) .0235(7) .0041(5) .0038(5) .0007(5) C8 .0209(7) .0202(6) .0185(6) .0032(5) .0030(5) .0013(5) C9 .0219(7) .0341(8) .0239(7) .0040(6) .0045(6) .0005(6) C10 .0300(8) .0422(9) .0230(7) .0030(6) .0087(6) .0041(7) C11 .0360(9) .0383(8) .0192(7) -.0034(6) .0027(6) .0019(7) C12 .0245(7) .0323(8) .0247(7) -.0015(6) .0000(6) -.0007(6) C13 .0205(7) .0223(7) .0219(6) .0018(5) .0041(5) .0015(5) C14 .0167(6) .0314(7) .0219(6) .0012(6) .0013(5) .0002(6) #=============================================================================== # 10. MOLECULAR GEOMETRY _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All esds are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.3192(16) . . yes O2 C14 1.2809(17) . . yes O3 C14 1.2296(18) . . yes O1 H1 1.10(2) . . no N1 C7 1.3022(18) . . yes N1 C8 1.4264(16) . . yes N1 H1' .948(18) . . no C1 C2 1.4070(19) . . no C1 C6 1.4198(19) . . no C2 C3 1.375(2) . . no C3 C4 1.399(2) . . no C4 C5 1.3725(19) . . no C5 C6 1.414(2) . . no C6 C7 1.4250(19) . . no C8 C13 1.4004(19) . . no C8 C9 1.3923(19) . . no C9 C10 1.3808(19) . . no C10 C11 1.384(2) . . no C11 C12 1.383(2) . . no C12 C13 1.3896(19) . . no C13 C14 1.5150(19) . . no C2 H2 1.006(16) . . no C3 H3 .987(16) . . no C4 H4 .940(19) . . no C5 H5 1.000(18) . . no C7 H7 .996(16) . . no C9 H9 .932(19) . . no C10 H10 .994(16) . . no C11 H11 .956(18) . . no C12 H12 .940(18) . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 H1 114.6(11) . . . no C7 N1 C8 125.99(12) . . . yes C7 N1 H1' 116.5(11) . . . no C8 N1 H1' 117.5(11) . . . no O1 C1 C2 122.93(12) . . . yes O1 C1 C6 118.57(12) . . . yes C2 C1 C6 118.50(12) . . . no C1 C2 C3 120.24(13) . . . no C2 C3 C4 121.78(13) . . . no C3 C4 C5 118.99(14) . . . no C4 C5 C6 120.92(13) . . . no C1 C6 C5 119.55(12) . . . no C1 C6 C7 122.88(12) . . . no C5 C6 C7 117.56(12) . . . no N1 C7 C6 125.15(12) . . . yes C9 C8 C13 120.37(11) . . . no N1 C8 C13 118.47(11) . . . yes N1 C8 C9 121.10(12) . . . yes C8 C9 C10 119.67(13) . . . no C9 C10 C11 120.82(13) . . . no C10 C11 C12 119.23(13) . . . no C11 C12 C13 121.43(13) . . . no C12 C13 C14 118.32(12) . . . no C8 C13 C12 118.47(12) . . . no C8 C13 C14 123.21(12) . . . no O2 C14 O3 126.01(13) . . . yes O2 C14 C13 114.75(11) . . . yes O3 C14 C13 119.23(12) . . . yes C1 C2 H2 117.8(9) . . . no C3 C2 H2 121.9(9) . . . no C2 C3 H3 120.5(10) . . . no C4 C3 H3 117.8(10) . . . no C3 C4 H4 120.7(11) . . . no C5 C4 H4 120.3(11) . . . no C4 C5 H5 122.1(10) . . . no C6 C5 H5 117.0(10) . . . no N1 C7 H7 119.4(9) . . . no C6 C7 H7 115.5(9) . . . no C8 C9 H9 119.4(11) . . . no C10 C9 H9 120.9(11) . . . no C9 C10 H10 117.6(10) . . . no C11 C10 H10 121.6(10) . . . no C10 C11 H11 122.3(10) . . . no C12 C11 H11 118.4(10) . . . no C11 C12 H12 119.9(10) . . . no C13 C12 H12 118.7(10) . . . no 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 C7 N1 C8 C13 -168.22(13) . . . . no C7 N1 C8 C9 9.0(2) . . . . no C8 N1 C7 C6 179.67(12) . . . . no C2 C1 C6 C5 .03(18) . . . . no C2 C1 C6 C7 -178.76(12) . . . . no O1 C1 C2 C3 179.75(15) . . . . no C6 C1 C2 C3 -1.22(19) . . . . no O1 C1 C6 C5 179.10(12) . . . . no O1 C1 C6 C7 .3(2) . . . . no C1 C2 C3 C4 1.1(2) . . . . no C2 C3 C4 C5 .2(2) . . . . no C3 C4 C5 C6 -1.4(2) . . . . no C4 C5 C6 C1 1.3(2) . . . . no C4 C5 C6 C7 -179.85(12) . . . . no C1 C6 C7 N1 -7.3(2) . . . . no C5 C6 C7 N1 173.91(13) . . . . no N1 C8 C13 C12 176.34(12) . . . . no N1 C8 C9 C10 -176.95(12) . . . . no C13 C8 C9 C10 .2(2) . . . . no C9 C8 C13 C14 179.83(13) . . . . no N1 C8 C13 C14 -2.98(19) . . . . no C9 C8 C13 C12 -.8(2) . . . . no C8 C9 C10 C11 .3(2) . . . . no C9 C10 C11 C12 -.1(2) . . . . no C10 C11 C12 C13 -.6(2) . . . . no C11 C12 C13 C8 1.1(2) . . . . no C11 C12 C13 C14 -179.58(12) . . . . no C8 C13 C14 O2 -31.70(19) . . . . no C8 C13 C14 O3 149.09(14) . . . . no C12 C13 C14 O2 148.98(13) . . . . no C12 C13 C14 O3 -30.23(19) . . . . no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O1 O2 2.9471(14) . . no O1 N1 2.6555(16) . . no O1 C5 3.4075(18) . 3_575 no O1 O2 2.4534(14) . 2_555 no O1 C14 3.2893(18) . 2_555 no O2 O1 2.4534(14) . 2_555 no O2 O1 2.9471(14) . . no O2 N1 2.6672(16) . . no O2 C2 3.3533(19) . 2_555 no O2 C1 3.2694(18) . 2_555 no O3 C9 3.237(2) . 4_575 no O3 C7 3.2329(19) . 4_575 no O1 H1' 1.936(18) . . no O2 H1 1.36(2) . 2_555 no O2 H1' 1.952(18) . . no O2 H2 2.714(16) . 2_555 no O3 H1 2.63(2) . 2_555 no O3 H12 2.568(16) . . no O3 H7 2.256(16) . 4_575 no O3 H9 2.391(19) . 4_575 no O3 H11 2.893(14) . 7_575 no N1 O1 2.6555(16) . . no N1 O2 2.6672(16) . . no N1 C3 3.3159(19) . 3_565 no C1 C6 3.4621(19) . 3_565 no C1 O2 3.2694(18) . 2_555 no C1 C5 3.412(2) . 3_565 no C1 C6 3.4201(19) . 3_575 no C1 C7 3.1465(19) . 3_575 no C2 C7 3.465(2) . 3_565 no C2 O2 3.3533(19) . 2_555 no C2 C7 3.382(2) . 3_575 no C2 C8 3.550(2) . 3_575 no C3 C13 3.476(2) . 3_575 no C3 C8 3.255(2) . 3_575 no C3 N1 3.3159(19) . 3_565 no C3 C7 3.417(2) . 3_565 no C4 C14 3.502(2) . 3_575 no C4 C13 3.559(2) . 3_575 no C5 C1 3.412(2) . 3_565 no C5 O1 3.4075(18) . 3_575 no C6 C1 3.4201(19) . 3_575 no C6 C6 3.345(2) . 3_575 no C6 C1 3.4621(19) . 3_565 no C6 C7 3.405(2) . 3_575 no C6 C6 3.524(2) . 3_565 no C7 O3 3.2329(19) . 4_475 no C7 C1 3.1465(19) . 3_575 no C7 C2 3.382(2) . 3_575 no C7 C3 3.417(2) . 3_565 no C7 C2 3.465(2) . 3_565 no C7 C6 3.405(2) . 3_575 no C8 C2 3.550(2) . 3_575 no C8 C3 3.255(2) . 3_575 no C9 O3 3.237(2) . 4_475 no C12 C12 3.520(2) . 7_565 no C12 C12 3.479(2) . 7_575 no C13 C4 3.559(2) . 3_575 no C13 C3 3.476(2) . 3_575 no C14 O1 3.2893(18) . 2_555 no C14 C4 3.502(2) . 3_575 no C1 H1' 2.600(18) . . no C2 H10 3.068(16) . 8_564 no C7 H9 2.641(18) . . no C9 H7 2.620(16) . . no C10 H2 3.026(16) . 8_565 no C14 H1' 2.515(18) . . no C14 H1 2.25(2) . 2_555 no C14 H2 2.972(16) . 2_555 no H1 H2 2.32(3) . . no H1 O2 1.36(2) . 2_555 no H1 O3 2.63(2) . 2_555 no H1 C14 2.25(2) . 2_555 no H1' O1 1.936(18) . . no H1' O2 1.952(18) . . no H1' C1 2.600(18) . . no H1' C14 2.515(18) . . no H2 H1 2.32(3) . . no H2 O2 2.714(16) . 2_555 no H2 C14 2.972(16) . 2_555 no H2 C10 3.026(16) . 8_564 no H2 H10 2.38(2) . 8_564 no H5 H7 2.26(2) . . no H7 C9 2.620(16) . . no H7 H5 2.26(2) . . no H7 H9 2.06(2) . . no H7 O3 2.256(16) . 4_475 no H9 C7 2.641(18) . . no H9 H7 2.06(2) . . no H9 O3 2.391(19) . 4_475 no H10 C2 3.068(16) . 8_565 no H10 H2 2.38(2) . 8_565 no H11 O3 2.893(14) . 7_575 no H12 O3 2.568(16) . . no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # O1 H1 O2 1.10(2) 1.36(2) 2.4534(14) 172.7(19) 2_555 yes N1 H1' O1 .948(18) 1.936(18) 2.6555(16) 130.9(15) . yes N1 H1' O2 .948(18) 1.952(18) 2.6672(16) 130.5(15) . yes C7 H7 O3 .996(16) 2.256(16) 3.2329(19) 166.4(11) 4_475 yes C9 H9 O3 .932(19) 2.391(19) 3.237(2) 150.9(17) 4_475 yes # End of Crystallographic Information File