# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Claramunt, Rosa' _publ_contact_author_email rclaramunt@ccia.uned.es _publ_section_title ; An extraordinary fast proton transfer in the solid state between two indazolinone tautomers ; loop_ _publ_author_name R.Claramunt M.Peez-Torralba C.Lopez C.Perez-Medina E.Pinilla ; M.R.Torres ; I.Alkorta J.Elguero # Attachment '- compound6.cif' data_C7H4F2N2O_compound6 _database_code_depnum_ccdc_archive 'CCDC 778538' #TrackingRef '- compound6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H4 F2 N2 O' _chemical_formula_weight 170.12 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 9.0766(7) _cell_length_b 11.6167(9) _cell_length_c 12.4603(10) _cell_angle_alpha 90.00 _cell_angle_beta 103.471(2) _cell_angle_gamma 90.00 _cell_volume 1277.67(17) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.769 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 0.161 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4493 _diffrn_reflns_av_R_equivalents 0.0380 _diffrn_reflns_av_sigmaI/netI 0.0286 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.90 _diffrn_reflns_theta_max 24.99 _reflns_number_total 1083 _reflns_number_gt 850 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0421P)^2^+0.3173P] 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 1083 _refine_ls_number_parameters 117 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0438 _refine_ls_R_factor_gt 0.0315 _refine_ls_wR_factor_ref 0.0825 _refine_ls_wR_factor_gt 0.0763 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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 C3 C 0.30671(18) 0.70958(14) 0.29602(13) 0.0298(4) Uani 1 1 d . . . C4 C 0.09166(18) 0.64633(14) 0.39144(13) 0.0320(4) Uani 1 1 d . . . C5 C -0.0183(2) 0.68609(15) 0.43974(14) 0.0367(5) Uani 1 1 d . . . H5 H -0.0794 0.6360 0.4683 0.044 Uiso 1 1 calc R . . C6 C -0.03528(19) 0.80542(16) 0.44463(14) 0.0362(5) Uani 1 1 d . . . C7 C 0.04936(19) 0.88436(15) 0.40519(13) 0.0348(4) Uani 1 1 d . . . H7 H 0.0331 0.9631 0.4095 0.042 Uiso 1 1 calc R . . C3A C 0.18425(18) 0.72128(14) 0.34932(12) 0.0282(4) Uani 1 1 d . . . C7A C 0.16210(18) 0.83968(14) 0.35794(12) 0.0286(4) Uani 1 1 d . . . F4 F 0.11247(12) 0.53152(9) 0.38272(9) 0.0537(4) Uani 1 1 d . . . F6 F -0.14432(12) 0.84410(10) 0.49331(9) 0.0563(4) Uani 1 1 d . . . N1 N 0.26953(16) 0.89515(12) 0.31655(12) 0.0357(4) Uani 1 1 d . . . N2 N 0.35168(17) 0.81373(12) 0.27368(12) 0.0343(4) Uani 1 1 d . . . O1 O 0.36807(13) 0.61437(10) 0.27208(10) 0.0404(4) Uani 1 1 d . . . H1 H 0.254(3) 0.9645(19) 0.2866(19) 0.080 Uiso 1 1 d . . . H2A H 0.436(5) 0.835(4) 0.251(4) 0.080 Uiso 0.50 1 d P . . H2B H 0.5000 0.621(3) 0.2500 0.080 Uiso 1 2 d S . . 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 C3 0.0284(9) 0.0265(10) 0.0348(9) -0.0001(7) 0.0081(8) -0.0002(7) C4 0.0315(10) 0.0247(10) 0.0390(10) 0.0017(7) 0.0069(8) -0.0013(7) C5 0.0334(10) 0.0378(12) 0.0411(10) 0.0038(8) 0.0133(8) -0.0052(8) C6 0.0287(10) 0.0459(12) 0.0361(10) -0.0036(8) 0.0116(8) 0.0032(8) C7 0.0358(10) 0.0280(10) 0.0408(10) -0.0009(8) 0.0092(8) 0.0052(8) C3A 0.0264(9) 0.0267(10) 0.0304(9) 0.0005(7) 0.0044(7) 0.0000(7) C7A 0.0274(9) 0.0270(9) 0.0302(9) 0.0028(7) 0.0042(7) 0.0003(7) F4 0.0587(7) 0.0271(7) 0.0842(8) 0.0024(5) 0.0348(6) -0.0040(5) F6 0.0475(7) 0.0579(8) 0.0751(8) -0.0104(6) 0.0377(6) 0.0014(6) N1 0.0354(9) 0.0248(9) 0.0501(9) 0.0060(7) 0.0165(7) 0.0027(7) N2 0.0354(8) 0.0261(9) 0.0451(9) 0.0016(6) 0.0168(7) 0.0002(6) O1 0.0375(7) 0.0265(7) 0.0633(8) -0.0052(6) 0.0241(6) -0.0004(5) _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 C3 O1 1.304(2) . ? C3 N2 1.327(2) . ? C3 C3A 1.428(2) . ? C4 F4 1.3549(19) . ? C4 C5 1.360(2) . ? C4 C3A 1.395(2) . ? C5 C6 1.398(2) . ? C5 H5 0.9300 . ? C6 F6 1.3524(19) . ? C6 C7 1.360(2) . ? C7 C7A 1.394(2) . ? C7 H7 0.9300 . ? C3A C7A 1.398(2) . ? C7A N1 1.366(2) . ? N1 N2 1.3862(19) . ? N1 H1 0.89(2) . ? N2 H2A 0.91(4) . ? O1 H2B 1.292(2) . ? 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 O1 C3 N2 123.84(15) . . ? O1 C3 C3A 127.41(15) . . ? N2 C3 C3A 108.75(14) . . ? F4 C4 C5 120.00(15) . . ? F4 C4 C3A 118.48(14) . . ? C5 C4 C3A 121.52(16) . . ? C4 C5 C6 117.13(16) . . ? C4 C5 H5 121.4 . . ? C6 C5 H5 121.4 . . ? F6 C6 C7 118.17(16) . . ? F6 C6 C5 116.68(15) . . ? C7 C6 C5 125.14(15) . . ? C6 C7 C7A 115.70(16) . . ? C6 C7 H7 122.2 . . ? C7A C7 H7 122.2 . . ? C7A C3A C4 118.38(15) . . ? C7A C3A C3 105.72(14) . . ? C4 C3A C3 135.90(15) . . ? N1 C7A C3A 107.88(14) . . ? N1 C7A C7 129.97(16) . . ? C3A C7A C7 122.12(15) . . ? C7A N1 N2 108.60(13) . . ? C7A N1 H1 122.2(16) . . ? N2 N1 H1 120.3(16) . . ? C3 N2 N1 108.78(14) . . ? C3 N2 H2A 129(3) . . ? N1 N2 H2A 120(3) . . ? C3 O1 H2B 117.6(14) . . ? 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 F4 C4 C5 C6 -179.07(14) . . . . ? C3A C4 C5 C6 0.5(3) . . . . ? C4 C5 C6 F6 -179.67(15) . . . . ? C4 C5 C6 C7 -0.1(3) . . . . ? F6 C6 C7 C7A 178.72(15) . . . . ? C5 C6 C7 C7A -0.8(3) . . . . ? F4 C4 C3A C7A 179.70(14) . . . . ? C5 C4 C3A C7A 0.1(2) . . . . ? F4 C4 C3A C3 -1.0(3) . . . . ? C5 C4 C3A C3 179.49(17) . . . . ? O1 C3 C3A C7A 178.96(15) . . . . ? N2 C3 C3A C7A -0.78(19) . . . . ? O1 C3 C3A C4 -0.4(3) . . . . ? N2 C3 C3A C4 179.82(18) . . . . ? C4 C3A C7A N1 177.04(15) . . . . ? C3 C3A C7A N1 -2.48(18) . . . . ? C4 C3A C7A C7 -1.2(2) . . . . ? C3 C3A C7A C7 179.30(14) . . . . ? C6 C7 C7A N1 -176.32(16) . . . . ? C6 C7 C7A C3A 1.5(2) . . . . ? C3A C7A N1 N2 4.77(18) . . . . ? C7 C7A N1 N2 -177.20(16) . . . . ? O1 C3 N2 N1 -176.04(15) . . . . ? C3A C3 N2 N1 3.71(19) . . . . ? C7A N1 N2 C3 -5.34(18) . . . . ? 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 O1 H2B O1 1.292(2) 1.292(2) 2.579(2) 173(3) 2_655 N1 H1 O1 0.89(2) 2.10(2) 2.9363(18) 157(2) 4 N2 H2A N2 0.91(4) 2.04(4) 2.888(3) 155(4) 2_655 _diffrn_measured_fraction_theta_max 0.961 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.961 _refine_diff_density_max 0.155 _refine_diff_density_min -0.225 _refine_diff_density_rms 0.041 #========================================================================END