# Electronic Supplementary Material (ESI) for Green Chemistry # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_sa1777 _database_code_depnum_ccdc_archive 'CCDC 874309' #TrackingRef '10472_web_deposit_cif_file_0_HaoChen_1333337298.sa1777.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7 F4 N3 O2, C6 H7 I N' _chemical_formula_sum 'C13 H7 F4 I N4 O2' _chemical_formula_weight 454.13 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.2406(14) _cell_length_b 6.3111(11) _cell_length_c 16.211(3) _cell_angle_alpha 90.00 _cell_angle_beta 98.719(7) _cell_angle_gamma 90.00 _cell_volume 732.2(2) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2945 _cell_measurement_theta_min 1.27 _cell_measurement_theta_max 27.49 _exptl_crystal_description platelet _exptl_crystal_colour colorless _exptl_crystal_size_max 0.49 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.060 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 436 _exptl_absorpt_coefficient_mu 2.249 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4054 _exptl_absorpt_correction_T_max 0.8406 _exptl_absorpt_process_details 'CrystalClear (Rigaku Inc., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Saturn724+ CCD' _diffrn_measurement_method '\w scans at fixed \c = 45\%' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5741 _diffrn_reflns_av_R_equivalents 0.0264 _diffrn_reflns_av_sigmaI/netI 0.0293 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.85 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3087 _reflns_number_gt 3048 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Olex2 ver 1.1' _computing_publication_material 'SHELX97 (Sheldrick, 2008)' _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^)+(0.0252P)^2^+0.7610P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.018(18) _refine_ls_number_reflns 3087 _refine_ls_number_parameters 217 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0265 _refine_ls_R_factor_gt 0.0261 _refine_ls_wR_factor_ref 0.0621 _refine_ls_wR_factor_gt 0.0618 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _refine_ls_shift/su_max 0.000 _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 I1 I 0.12250(3) 1.08770(5) 0.070083(14) 0.04023(9) Uani 1 1 d . . . F1 F 0.5666(3) 1.2323(3) 0.29599(14) 0.0274(4) Uani 1 1 d . . . F2 F 0.6413(3) 0.9716(3) 0.42512(12) 0.0263(4) Uani 1 1 d . . . F3 F 0.8616(3) 0.4605(3) 0.25062(14) 0.0265(4) Uani 1 1 d . . . F4 F 0.7757(3) 0.7171(4) 0.12080(13) 0.0296(5) Uani 1 1 d . . . O1 O 0.6505(3) 0.5151(4) 0.45233(15) 0.0245(5) Uani 1 1 d . . . O2 O 0.9498(3) 0.4777(4) 0.43614(17) 0.0311(6) Uani 1 1 d . . . N1 N 0.6225(4) 1.1343(5) 0.14103(19) 0.0288(8) Uani 1 1 d . . . N2 N 0.6166(3) 1.0808(13) 0.06671(17) 0.0294(6) Uani 1 1 d . . . N3 N 0.6016(5) 1.0602(9) -0.00261(19) 0.0409(10) Uani 1 1 d . . . N4 N 0.2832(4) 0.6951(5) 0.43123(17) 0.0215(6) Uani 1 1 d . . . H4A H 0.3830 0.6173 0.4209 0.026 Uiso 1 1 d R . . H4C H 0.3008 0.7958 0.4719 0.026 Uiso 1 1 d R . . H4B H 0.1834 0.6150 0.4398 0.026 Uiso 1 1 d R . . C1 C 0.6696(4) 0.9844(5) 0.2041(2) 0.0201(6) Uani 1 1 d . . . C2 C 0.6402(4) 1.0424(5) 0.2843(2) 0.0204(7) Uani 1 1 d . . . C3 C 0.6812(4) 0.9054(5) 0.3507(2) 0.0195(6) Uani 1 1 d . . . C4 C 0.7555(4) 0.7052(5) 0.3435(2) 0.0195(6) Uani 1 1 d . . . C5 C 0.7887(4) 0.6509(5) 0.2638(2) 0.0206(7) Uani 1 1 d . . . C6 C 0.7440(4) 0.7834(5) 0.1962(2) 0.0205(6) Uani 1 1 d . . . C7 C 0.7911(4) 0.5529(5) 0.4171(2) 0.0202(7) Uani 1 1 d . . . C8 C 0.1765(4) 0.9534(6) 0.1897(2) 0.0241(7) Uani 1 1 d . . . C9 C 0.1417(4) 1.0738(8) 0.2569(2) 0.0253(6) Uani 1 1 d . . . H9 H 0.0937 1.2135 0.2485 0.030 Uiso 1 1 calc R . . C10 C 0.1774(4) 0.9894(6) 0.3372(2) 0.0226(6) Uani 1 1 d . . . H10 H 0.1548 1.0707 0.3839 0.027 Uiso 1 1 calc R . . C11 C 0.2462(4) 0.7855(5) 0.3476(2) 0.0200(6) Uani 1 1 d . . . C12 C 0.2789(4) 0.6638(5) 0.2803(2) 0.0214(6) Uani 1 1 d . . . H12 H 0.3252 0.5234 0.2889 0.026 Uiso 1 1 calc R . . C13 C 0.2438(4) 0.7479(6) 0.2003(2) 0.0235(7) Uani 1 1 d . . . H13 H 0.2656 0.6660 0.1536 0.028 Uiso 1 1 calc R . . 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 I1 0.03016(11) 0.05865(17) 0.02955(12) 0.02047(14) -0.00298(8) -0.00783(14) F1 0.0277(10) 0.0159(9) 0.0398(12) -0.0014(9) 0.0095(9) 0.0035(8) F2 0.0305(10) 0.0271(11) 0.0222(10) -0.0058(8) 0.0073(8) -0.0006(8) F3 0.0289(10) 0.0172(10) 0.0359(12) -0.0036(9) 0.0127(9) 0.0046(8) F4 0.0365(11) 0.0321(11) 0.0221(10) -0.0072(9) 0.0103(9) -0.0003(9) O1 0.0209(10) 0.0295(13) 0.0241(11) 0.0059(10) 0.0063(9) 0.0017(8) O2 0.0192(11) 0.0346(14) 0.0396(15) 0.0130(13) 0.0045(11) 0.0004(10) N1 0.0361(15) 0.025(2) 0.0244(14) 0.0033(13) 0.0024(11) -0.0001(12) N2 0.0240(11) 0.0364(16) 0.0275(14) 0.0092(16) 0.0026(9) 0.0003(15) N3 0.0401(16) 0.057(3) 0.0258(15) 0.005(2) 0.0060(12) 0.009(2) N4 0.0205(12) 0.0231(14) 0.0213(13) 0.0014(12) 0.0038(10) -0.0015(11) C1 0.0185(14) 0.0217(16) 0.0204(16) 0.0014(13) 0.0039(12) -0.0030(12) C2 0.0190(13) 0.0181(19) 0.0244(15) -0.0052(12) 0.0041(11) -0.0019(11) C3 0.0175(14) 0.0227(16) 0.0195(15) -0.0048(13) 0.0064(12) -0.0024(11) C4 0.0147(13) 0.0221(16) 0.0220(16) 0.0002(13) 0.0042(11) -0.0027(11) C5 0.0187(14) 0.0151(16) 0.0285(17) -0.0027(12) 0.0058(12) -0.0009(10) C6 0.0208(14) 0.0215(16) 0.0201(16) -0.0061(13) 0.0065(12) -0.0033(12) C7 0.0212(13) 0.0172(19) 0.0219(14) -0.0016(13) 0.0024(10) -0.0025(12) C8 0.0195(14) 0.0292(18) 0.0224(16) 0.0095(14) -0.0009(12) -0.0035(13) C9 0.0202(12) 0.0216(16) 0.0328(16) 0.0080(19) -0.0004(11) 0.0006(16) C10 0.0214(15) 0.0190(15) 0.0272(17) -0.0040(13) 0.0037(12) 0.0007(12) C11 0.0159(13) 0.0222(16) 0.0214(15) 0.0016(13) 0.0011(11) -0.0027(11) C12 0.0199(14) 0.0171(14) 0.0270(16) -0.0008(13) 0.0032(12) 0.0009(11) C13 0.0221(15) 0.0265(17) 0.0222(16) -0.0027(14) 0.0046(13) -0.0025(13) _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 I1 C8 2.098(3) . ? F1 C2 1.337(4) . ? F2 C3 1.349(4) . ? F3 C5 1.343(4) . ? F4 C6 1.344(4) . ? O1 C7 1.263(4) . ? O2 C7 1.239(4) . ? N1 N2 1.246(4) . ? N1 C1 1.396(4) . ? N2 N3 1.120(4) . ? N4 C11 1.458(4) . ? N4 H4A 0.9100 . ? N4 H4C 0.9100 . ? N4 H4B 0.9100 . ? C1 C6 1.392(5) . ? C1 C2 1.398(4) . ? C2 C3 1.377(5) . ? C3 C4 1.385(5) . ? C4 C5 1.392(5) . ? C4 C7 1.524(5) . ? C5 C6 1.377(5) . ? C8 C9 1.383(5) . ? C8 C13 1.387(5) . ? C9 C10 1.393(5) . ? C9 H9 0.9500 . ? C10 C11 1.381(5) . ? C10 H10 0.9500 . ? C11 C12 1.382(5) . ? C12 C13 1.389(5) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? 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 N2 N1 C1 119.5(5) . . ? N3 N2 N1 170.3(8) . . ? C11 N4 H4A 94.5 . . ? C11 N4 H4C 112.7 . . ? H4A N4 H4C 118.8 . . ? C11 N4 H4B 108.7 . . ? H4A N4 H4B 113.5 . . ? H4C N4 H4B 107.8 . . ? C6 C1 N1 127.3(3) . . ? C6 C1 C2 116.0(3) . . ? N1 C1 C2 116.7(3) . . ? F1 C2 C3 119.7(3) . . ? F1 C2 C1 119.1(3) . . ? C3 C2 C1 121.2(3) . . ? F2 C3 C2 117.0(3) . . ? F2 C3 C4 119.8(3) . . ? C2 C3 C4 123.2(3) . . ? C3 C4 C5 115.2(3) . . ? C3 C4 C7 122.1(3) . . ? C5 C4 C7 122.6(3) . . ? F3 C5 C6 117.9(3) . . ? F3 C5 C4 119.7(3) . . ? C6 C5 C4 122.4(3) . . ? F4 C6 C5 118.9(3) . . ? F4 C6 C1 119.2(3) . . ? C5 C6 C1 121.9(3) . . ? O2 C7 O1 126.6(3) . . ? O2 C7 C4 118.5(3) . . ? O1 C7 C4 114.9(3) . . ? C9 C8 C13 121.2(3) . . ? C9 C8 I1 118.4(3) . . ? C13 C8 I1 120.3(3) . . ? C8 C9 C10 119.7(4) . . ? C8 C9 H9 120.1 . . ? C10 C9 H9 120.1 . . ? C11 C10 C9 118.9(3) . . ? C11 C10 H10 120.6 . . ? C9 C10 H10 120.6 . . ? C10 C11 C12 121.6(3) . . ? C10 C11 N4 119.3(3) . . ? C12 C11 N4 119.1(3) . . ? C11 C12 C13 119.7(3) . . ? C11 C12 H12 120.2 . . ? C13 C12 H12 120.2 . . ? C8 C13 C12 118.9(3) . . ? C8 C13 H13 120.5 . . ? C12 C13 H13 120.5 . . ? 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 C1 N1 N2 N3 173(3) . . . . ? N2 N1 C1 C6 12.0(5) . . . . ? N2 N1 C1 C2 -168.4(3) . . . . ? C6 C1 C2 F1 -179.1(3) . . . . ? N1 C1 C2 F1 1.3(4) . . . . ? C6 C1 C2 C3 -0.8(4) . . . . ? N1 C1 C2 C3 179.6(3) . . . . ? F1 C2 C3 F2 0.9(4) . . . . ? C1 C2 C3 F2 -177.4(3) . . . . ? F1 C2 C3 C4 179.2(3) . . . . ? C1 C2 C3 C4 0.9(5) . . . . ? F2 C3 C4 C5 179.0(3) . . . . ? C2 C3 C4 C5 0.7(5) . . . . ? F2 C3 C4 C7 1.2(4) . . . . ? C2 C3 C4 C7 -177.1(3) . . . . ? C3 C4 C5 F3 179.6(3) . . . . ? C7 C4 C5 F3 -2.6(4) . . . . ? C3 C4 C5 C6 -2.4(5) . . . . ? C7 C4 C5 C6 175.3(3) . . . . ? F3 C5 C6 F4 -0.2(4) . . . . ? C4 C5 C6 F4 -178.2(3) . . . . ? F3 C5 C6 C1 -179.3(3) . . . . ? C4 C5 C6 C1 2.7(5) . . . . ? N1 C1 C6 F4 -0.6(5) . . . . ? C2 C1 C6 F4 179.9(3) . . . . ? N1 C1 C6 C5 178.6(3) . . . . ? C2 C1 C6 C5 -1.0(5) . . . . ? C3 C4 C7 O2 -125.5(4) . . . . ? C5 C4 C7 O2 56.9(5) . . . . ? C3 C4 C7 O1 55.1(4) . . . . ? C5 C4 C7 O1 -122.5(3) . . . . ? C13 C8 C9 C10 1.0(5) . . . . ? I1 C8 C9 C10 -179.6(2) . . . . ? C8 C9 C10 C11 -0.4(5) . . . . ? C9 C10 C11 C12 -0.5(5) . . . . ? C9 C10 C11 N4 -179.7(3) . . . . ? C10 C11 C12 C13 0.6(5) . . . . ? N4 C11 C12 C13 179.8(3) . . . . ? C9 C8 C13 C12 -0.9(5) . . . . ? I1 C8 C13 C12 179.7(2) . . . . ? C11 C12 C13 C8 0.1(5) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.868 _refine_diff_density_min -0.520 _refine_diff_density_rms 0.078 data_a _database_code_depnum_ccdc_archive 'CCDC 874310' #TrackingRef '10473_web_deposit_cif_file_1_HaoChen_1333337298.a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7 H F4 N3 O2, C8 H9 N O' _chemical_formula_sum 'C15 H10 F4 N4 O3' _chemical_formula_weight 370.27 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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.7206(11) _cell_length_b 10.897(2) _cell_length_c 12.306(3) _cell_angle_alpha 86.60(3) _cell_angle_beta 84.86(3) _cell_angle_gamma 80.87(3) _cell_volume 753.5(3) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 323 _cell_measurement_theta_min 1.8949 _cell_measurement_theta_max 27.4507 _exptl_crystal_description block _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.632 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 376 _exptl_absorpt_coefficient_mu 0.149 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6893 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'CrystalClear (Rigaku Inc., 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator Confocal _diffrn_measurement_device_type 'MM007HF + CCD (Saturn724+)' _diffrn_measurement_method '\w scans at fixed \c = 45\%' _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6742 _diffrn_reflns_av_R_equivalents 0.0400 _diffrn_reflns_av_sigmaI/netI 0.0415 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 27.52 _reflns_number_total 3423 _reflns_number_gt 3011 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _computing_structure_solution 'SHELX-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELX-97 (Sheldrick, 2008)' _computing_molecular_graphics ; Mercury: visualization and analysis of crystal structures, C. F. Macrae, P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor, M. Towler and J. van de Streek, J. Appl. Cryst., 39, 453-457, 2006. ; _computing_publication_material 'SHELX-97 (Sheldrick, 2008)' _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^)+(0.0676P)^2^+0.2017P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3423 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0604 _refine_ls_R_factor_gt 0.0532 _refine_ls_wR_factor_ref 0.1360 _refine_ls_wR_factor_gt 0.1303 _refine_ls_goodness_of_fit_ref 1.098 _refine_ls_restrained_S_all 1.098 _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 F1 F 0.91299(19) 0.83508(9) 0.34562(9) 0.0372(3) Uani 1 1 d . . . F2 F 1.08125(17) 0.64025(9) 0.22971(8) 0.0349(3) Uani 1 1 d . . . F3 F 0.40391(17) 0.45624(9) 0.35446(9) 0.0370(3) Uani 1 1 d . . . F4 F 0.23700(17) 0.65284(9) 0.46876(9) 0.0373(3) Uani 1 1 d . . . O1 O 0.8141(2) 0.32305(11) 0.25853(11) 0.0420(3) Uani 1 1 d . . . O2 O 0.9552(2) 0.45104(11) 0.13014(10) 0.0382(3) Uani 1 1 d . . . H2 H 1.0013 0.3838 0.0992 0.046 Uiso 1 1 d R . . O3 O 0.8917(2) 0.73991(10) -0.01916(10) 0.0335(3) Uani 1 1 d . . . N1 N 0.4988(3) 0.86150(13) 0.46507(12) 0.0369(4) Uani 1 1 d . . . N2 N 0.3042(3) 0.87434(13) 0.52174(12) 0.0344(3) Uani 1 1 d . . . N3 N 0.1391(3) 0.90222(15) 0.57553(15) 0.0464(4) Uani 1 1 d . . . N4 N 0.3873(3) 1.18249(13) 0.26962(12) 0.0350(3) Uani 1 1 d . . . H4B H 0.4808 1.2373 0.2667 0.042 Uiso 1 1 d R . . H4A H 0.2432 1.1996 0.2974 0.042 Uiso 1 1 d R . . C1 C 0.5684(3) 0.75169(14) 0.40929(13) 0.0268(3) Uani 1 1 d . . . C2 C 0.4465(3) 0.65095(14) 0.40957(13) 0.0272(3) Uani 1 1 d . . . C3 C 0.5354(3) 0.54837(14) 0.35031(13) 0.0269(3) Uani 1 1 d . . . C4 C 0.7497(3) 0.53942(13) 0.28614(13) 0.0254(3) Uani 1 1 d . . . C5 C 0.8699(3) 0.64075(14) 0.28640(13) 0.0260(3) Uani 1 1 d . . . C6 C 0.7843(3) 0.74260(14) 0.34680(13) 0.0270(3) Uani 1 1 d . . . C7 C 0.8438(3) 0.42583(14) 0.22330(14) 0.0277(3) Uani 1 1 d . . . C8 C 0.5218(3) 0.66641(15) 0.01053(15) 0.0340(4) Uani 1 1 d . . . H8C H 0.3762 0.7115 -0.0180 0.051 Uiso 1 1 calc R . . H8B H 0.4823 0.6242 0.0807 0.051 Uiso 1 1 calc R . . H8A H 0.5987 0.6047 -0.0414 0.051 Uiso 1 1 calc R . . C9 C 0.6875(3) 0.75641(14) 0.02617(13) 0.0253(3) Uani 1 1 d . . . C10 C 0.6085(3) 0.86300(13) 0.09325(12) 0.0234(3) Uani 1 1 d . . . C11 C 0.3824(3) 0.88410(14) 0.14933(13) 0.0265(3) Uani 1 1 d . . . H11 H 0.2772 0.8254 0.1463 0.032 Uiso 1 1 calc R . . C12 C 0.3106(3) 0.98817(15) 0.20856(13) 0.0279(3) Uani 1 1 d . . . H12 H 0.1576 0.9998 0.2469 0.033 Uiso 1 1 calc R . . C13 C 0.4606(3) 1.07750(14) 0.21310(13) 0.0255(3) Uani 1 1 d . . . C14 C 0.6883(3) 1.05632(14) 0.15880(13) 0.0262(3) Uani 1 1 d . . . H14 H 0.7940 1.1147 0.1623 0.031 Uiso 1 1 calc R . . C15 C 0.7589(3) 0.95130(14) 0.10063(13) 0.0251(3) Uani 1 1 d . . . H15 H 0.9139 0.9382 0.0644 0.030 Uiso 1 1 calc R . . 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 F1 0.0474(6) 0.0269(5) 0.0404(6) -0.0081(4) 0.0022(5) -0.0158(4) F2 0.0310(5) 0.0334(5) 0.0407(6) -0.0086(4) 0.0082(4) -0.0101(4) F3 0.0329(5) 0.0306(5) 0.0494(6) -0.0113(4) 0.0059(4) -0.0128(4) F4 0.0311(5) 0.0389(5) 0.0408(6) -0.0107(4) 0.0089(4) -0.0051(4) O1 0.0516(8) 0.0228(6) 0.0501(8) -0.0086(5) 0.0111(6) -0.0074(5) O2 0.0487(7) 0.0268(6) 0.0368(7) -0.0112(5) 0.0116(6) -0.0035(5) O3 0.0306(6) 0.0310(6) 0.0387(7) -0.0136(5) 0.0060(5) -0.0047(5) N1 0.0459(8) 0.0297(7) 0.0345(8) -0.0132(6) 0.0056(7) -0.0047(6) N2 0.0458(8) 0.0251(7) 0.0303(7) -0.0061(6) -0.0027(6) 0.0018(6) N3 0.0507(10) 0.0360(8) 0.0477(10) -0.0138(7) 0.0090(8) 0.0048(7) N4 0.0335(7) 0.0310(7) 0.0405(8) -0.0143(6) 0.0022(6) -0.0032(6) C1 0.0353(8) 0.0212(7) 0.0231(8) -0.0052(6) -0.0038(6) 0.0001(6) C2 0.0264(7) 0.0285(7) 0.0254(8) -0.0041(6) 0.0019(6) -0.0010(6) C3 0.0281(7) 0.0237(7) 0.0305(8) -0.0044(6) -0.0033(6) -0.0068(6) C4 0.0288(7) 0.0213(7) 0.0260(8) -0.0049(6) -0.0021(6) -0.0024(6) C5 0.0278(7) 0.0255(7) 0.0247(8) -0.0022(6) -0.0005(6) -0.0041(6) C6 0.0340(8) 0.0215(7) 0.0271(8) -0.0026(6) -0.0039(6) -0.0079(6) C7 0.0263(7) 0.0241(7) 0.0327(8) -0.0073(6) -0.0010(6) -0.0022(6) C8 0.0349(8) 0.0275(8) 0.0416(10) -0.0100(7) -0.0010(7) -0.0086(7) C9 0.0276(7) 0.0235(7) 0.0244(8) -0.0016(6) -0.0032(6) -0.0023(6) C10 0.0246(7) 0.0231(7) 0.0224(7) -0.0021(6) -0.0022(6) -0.0034(5) C11 0.0231(7) 0.0272(7) 0.0304(8) -0.0027(6) -0.0004(6) -0.0075(6) C12 0.0236(7) 0.0296(8) 0.0295(8) -0.0039(6) 0.0029(6) -0.0035(6) C13 0.0278(7) 0.0255(7) 0.0223(7) -0.0039(6) -0.0027(6) 0.0002(6) C14 0.0250(7) 0.0252(7) 0.0296(8) -0.0035(6) -0.0028(6) -0.0064(6) C15 0.0217(7) 0.0267(7) 0.0269(8) -0.0031(6) 0.0002(6) -0.0041(6) _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 F1 C6 1.3376(17) . ? F2 C5 1.3402(18) . ? F3 C3 1.3429(17) . ? F4 C2 1.3436(18) . ? O1 C7 1.209(2) . ? O2 C7 1.297(2) . ? O2 H2 0.8399 . ? O3 C9 1.2395(19) . ? N1 N2 1.252(2) . ? N1 C1 1.400(2) . ? N2 N3 1.115(2) . ? N4 C13 1.363(2) . ? N4 H4B 0.8600 . ? N4 H4A 0.8600 . ? C1 C6 1.388(2) . ? C1 C2 1.390(2) . ? C2 C3 1.375(2) . ? C3 C4 1.390(2) . ? C4 C5 1.391(2) . ? C4 C7 1.499(2) . ? C5 C6 1.373(2) . ? C8 C9 1.499(2) . ? C8 H8C 0.9800 . ? C8 H8B 0.9800 . ? C8 H8A 0.9800 . ? C9 C10 1.454(2) . ? C10 C15 1.400(2) . ? C10 C11 1.402(2) . ? C11 C12 1.372(2) . ? C11 H11 0.9500 . ? C12 C13 1.402(2) . ? C12 H12 0.9500 . ? C13 C14 1.402(2) . ? C14 C15 1.372(2) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? 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 C7 O2 H2 107.9 . . ? N2 N1 C1 118.30(14) . . ? N3 N2 N1 169.73(18) . . ? C13 N4 H4B 117.9 . . ? C13 N4 H4A 120.9 . . ? H4B N4 H4A 120.3 . . ? C6 C1 C2 116.49(14) . . ? C6 C1 N1 116.03(14) . . ? C2 C1 N1 127.48(15) . . ? F4 C2 C3 118.72(14) . . ? F4 C2 C1 119.81(13) . . ? C3 C2 C1 121.47(14) . . ? F3 C3 C2 117.27(14) . . ? F3 C3 C4 120.32(14) . . ? C2 C3 C4 122.39(14) . . ? C3 C4 C5 115.63(14) . . ? C3 C4 C7 121.27(14) . . ? C5 C4 C7 123.08(14) . . ? F2 C5 C6 117.10(14) . . ? F2 C5 C4 120.51(14) . . ? C6 C5 C4 122.35(14) . . ? F1 C6 C5 119.06(14) . . ? F1 C6 C1 119.29(14) . . ? C5 C6 C1 121.65(14) . . ? O1 C7 O2 125.40(15) . . ? O1 C7 C4 121.59(15) . . ? O2 C7 C4 113.01(13) . . ? C9 C8 H8C 109.5 . . ? C9 C8 H8B 109.5 . . ? H8C C8 H8B 109.5 . . ? C9 C8 H8A 109.5 . . ? H8C C8 H8A 109.5 . . ? H8B C8 H8A 109.5 . . ? O3 C9 C10 120.22(14) . . ? O3 C9 C8 119.55(14) . . ? C10 C9 C8 120.23(13) . . ? C15 C10 C11 117.66(14) . . ? C15 C10 C9 119.62(13) . . ? C11 C10 C9 122.70(14) . . ? C12 C11 C10 121.11(14) . . ? C12 C11 H11 119.4 . . ? C10 C11 H11 119.4 . . ? C11 C12 C13 120.72(14) . . ? C11 C12 H12 119.6 . . ? C13 C12 H12 119.6 . . ? N4 C13 C14 120.57(14) . . ? N4 C13 C12 120.82(14) . . ? C14 C13 C12 118.62(14) . . ? C15 C14 C13 120.09(14) . . ? C15 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? C14 C15 C10 121.78(14) . . ? C14 C15 H15 119.1 . . ? C10 C15 H15 119.1 . . ? 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 C1 N1 N2 N3 -180(1) . . . . ? N2 N1 C1 C6 179.38(16) . . . . ? N2 N1 C1 C2 -0.8(3) . . . . ? C6 C1 C2 F4 179.58(14) . . . . ? N1 C1 C2 F4 -0.2(3) . . . . ? C6 C1 C2 C3 -0.4(2) . . . . ? N1 C1 C2 C3 179.75(16) . . . . ? F4 C2 C3 F3 0.8(2) . . . . ? C1 C2 C3 F3 -179.18(14) . . . . ? F4 C2 C3 C4 179.38(15) . . . . ? C1 C2 C3 C4 -0.6(3) . . . . ? F3 C3 C4 C5 179.04(14) . . . . ? C2 C3 C4 C5 0.5(2) . . . . ? F3 C3 C4 C7 -2.2(2) . . . . ? C2 C3 C4 C7 179.32(15) . . . . ? C3 C4 C5 F2 178.15(14) . . . . ? C7 C4 C5 F2 -0.6(2) . . . . ? C3 C4 C5 C6 0.6(2) . . . . ? C7 C4 C5 C6 -178.15(15) . . . . ? F2 C5 C6 F1 0.4(2) . . . . ? C4 C5 C6 F1 178.03(14) . . . . ? F2 C5 C6 C1 -179.32(14) . . . . ? C4 C5 C6 C1 -1.7(3) . . . . ? C2 C1 C6 F1 -178.19(14) . . . . ? N1 C1 C6 F1 1.7(2) . . . . ? C2 C1 C6 C5 1.6(2) . . . . ? N1 C1 C6 C5 -178.60(15) . . . . ? C3 C4 C7 O1 -34.8(2) . . . . ? C5 C4 C7 O1 143.86(18) . . . . ? C3 C4 C7 O2 144.81(16) . . . . ? C5 C4 C7 O2 -36.5(2) . . . . ? O3 C9 C10 C15 4.2(2) . . . . ? C8 C9 C10 C15 -175.28(15) . . . . ? O3 C9 C10 C11 -177.85(15) . . . . ? C8 C9 C10 C11 2.7(2) . . . . ? C15 C10 C11 C12 0.5(2) . . . . ? C9 C10 C11 C12 -177.51(15) . . . . ? C10 C11 C12 C13 1.1(3) . . . . ? C11 C12 C13 N4 178.32(15) . . . . ? C11 C12 C13 C14 -2.1(2) . . . . ? N4 C13 C14 C15 -178.92(15) . . . . ? C12 C13 C14 C15 1.5(2) . . . . ? C13 C14 C15 C10 0.1(2) . . . . ? C11 C10 C15 C14 -1.1(2) . . . . ? C9 C10 C15 C14 176.97(15) . . . . ? 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 O2 H2 O3 0.84 1.72 2.5509(17) 171.3 2_765 N4 H4B O1 0.86 2.24 3.071(2) 161.0 1_565 _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.314 _refine_diff_density_min -0.254 _refine_diff_density_rms 0.059