# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email ola.wendt@organic.lu.se loop_ _publ_author_name C.-J.Wallentin E.Orentas M.Johnson 'N. Bathori' E.Butkus O.F.Wendt K.Warnmark L.Ohrstrom _publ_contact_author_name O.F.Wendt data_compound2 _database_code_depnum_ccdc_archive 'CCDC 768528' #TrackingRef 'cif.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H8 O2' _chemical_formula_sum 'C9 H8 O2' _chemical_formula_weight 148.16 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 6.8088(3) _cell_length_b 7.4891(4) _cell_length_c 14.8396(8) _cell_angle_alpha 90.00 _cell_angle_beta 100.854(5) _cell_angle_gamma 90.00 _cell_volume 743.16(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2465 _cell_measurement_theta_min 2.7088 _cell_measurement_theta_max 33.0171 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.324 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 312 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_T_min 0.86049 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET) (compiled Aug 28 2006,13:05:05) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Xcalibur 3' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean 16.1829 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 7381 _diffrn_reflns_av_R_equivalents 0.0175 _diffrn_reflns_av_sigmaI/netI 0.0341 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.80 _diffrn_reflns_theta_max 33.09 _reflns_number_total 2627 _reflns_number_gt 1366 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET) (compiled Aug 28 2006,13:05:05) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET) (compiled Aug 28 2006,13:05:05) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET) (compiled Aug 28 2006,13:05:05) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0665P)^2^+0.0000P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2627 _refine_ls_number_parameters 100 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0860 _refine_ls_R_factor_gt 0.0412 _refine_ls_wR_factor_ref 0.1337 _refine_ls_wR_factor_gt 0.1199 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _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 O1 O 0.59248(12) 0.26746(12) 0.04561(6) 0.0725(3) Uani 1 1 d . . . O2 O 0.02841(15) 0.16930(16) 0.29355(6) 0.0910(3) Uani 1 1 d . . . C3 C 0.49715(15) 0.09000(14) 0.22993(7) 0.0516(3) Uani 1 1 d . . . H3 H 0.6323 0.0891 0.2563 0.062 Uiso 1 1 calc R . . C4 C 0.43737(14) 0.05408(14) 0.12905(7) 0.0489(3) Uani 1 1 d . . . H4 H 0.5301 -0.0324 0.1104 0.059 Uiso 1 1 calc R . . C5 C 0.44456(15) 0.22636(14) 0.07626(7) 0.0502(3) Uani 1 1 d . . . C6 C 0.10486(16) 0.29107(17) 0.09762(8) 0.0600(3) Uani 1 1 d . . . H6 H -0.0026 0.3696 0.0917 0.072 Uiso 1 1 calc R . . C7 C 0.15056(17) 0.13619(16) 0.24554(8) 0.0590(3) Uani 1 1 d . . . C8 C 0.08867(15) 0.11330(18) 0.14235(8) 0.0577(3) Uani 1 1 d . . . H8 H -0.0500 0.0713 0.1276 0.069 Uiso 1 1 calc R . . C9 C 0.26675(17) 0.34041(16) 0.06626(7) 0.0575(3) Uani 1 1 d . . . H9 H 0.2674 0.4503 0.0371 0.069 Uiso 1 1 calc R . . C10 C 0.36556(17) 0.12289(15) 0.28281(7) 0.0558(3) Uani 1 1 d . . . H10 H 0.4105 0.1381 0.3455 0.067 Uiso 1 1 calc R . . C11 C 0.22486(16) -0.02207(16) 0.10848(8) 0.0559(3) Uani 1 1 d . . . H11A H 0.1826 -0.0415 0.0431 0.067 Uiso 1 1 calc R . . H11B H 0.2200 -0.1352 0.1398 0.067 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 O1 0.0603(5) 0.0832(6) 0.0828(6) 0.0088(4) 0.0362(5) -0.0019(4) O2 0.0816(7) 0.1227(9) 0.0810(6) -0.0003(6) 0.0465(5) 0.0191(6) C3 0.0445(5) 0.0511(6) 0.0566(7) 0.0053(5) 0.0027(5) 0.0021(4) C4 0.0417(5) 0.0511(6) 0.0559(6) -0.0039(4) 0.0144(4) 0.0050(4) C5 0.0452(6) 0.0614(7) 0.0458(6) -0.0028(5) 0.0129(4) -0.0025(5) C6 0.0437(6) 0.0768(8) 0.0569(7) 0.0046(6) 0.0025(5) 0.0153(5) C7 0.0580(7) 0.0638(7) 0.0606(7) 0.0030(5) 0.0249(5) 0.0044(5) C8 0.0342(5) 0.0780(8) 0.0618(7) -0.0018(5) 0.0114(5) -0.0043(5) C9 0.0584(7) 0.0622(7) 0.0510(6) 0.0094(5) 0.0080(5) 0.0087(5) C10 0.0640(7) 0.0571(6) 0.0453(6) 0.0027(5) 0.0076(5) 0.0015(5) C11 0.0516(6) 0.0592(7) 0.0578(6) -0.0097(5) 0.0125(5) -0.0093(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 O1 C5 1.2200(12) . ? O2 C7 1.2181(12) . ? C3 C10 1.3207(14) . ? C3 C4 1.4998(14) . ? C3 H3 0.9300 . ? C4 C5 1.5150(15) . ? C4 C11 1.5316(14) . ? C4 H4 0.9800 . ? C5 C9 1.4662(15) . ? C6 C9 1.3272(16) . ? C6 C8 1.5009(17) . ? C6 H6 0.9300 . ? C7 C10 1.4676(17) . ? C7 C8 1.5194(15) . ? C8 C11 1.5218(16) . ? C8 H8 0.9800 . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? 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 C10 C3 C4 122.66(9) . . ? C10 C3 H3 118.7 . . ? C4 C3 H3 118.7 . . ? C3 C4 C5 109.53(8) . . ? C3 C4 C11 109.53(8) . . ? C5 C4 C11 109.59(8) . . ? C3 C4 H4 109.4 . . ? C5 C4 H4 109.4 . . ? C11 C4 H4 109.4 . . ? O1 C5 C9 122.63(11) . . ? O1 C5 C4 121.13(10) . . ? C9 C5 C4 116.23(9) . . ? C9 C6 C8 122.49(10) . . ? C9 C6 H6 118.8 . . ? C8 C6 H6 118.8 . . ? O2 C7 C10 122.40(11) . . ? O2 C7 C8 121.47(10) . . ? C10 C7 C8 116.10(9) . . ? C6 C8 C11 110.17(9) . . ? C6 C8 C7 108.43(10) . . ? C11 C8 C7 109.72(9) . . ? C6 C8 H8 109.5 . . ? C11 C8 H8 109.5 . . ? C7 C8 H8 109.5 . . ? C6 C9 C5 121.79(11) . . ? C6 C9 H9 119.1 . . ? C5 C9 H9 119.1 . . ? C3 C10 C7 121.93(10) . . ? C3 C10 H10 119.0 . . ? C7 C10 H10 119.0 . . ? C8 C11 C4 107.32(9) . . ? C8 C11 H11A 110.3 . . ? C4 C11 H11A 110.3 . . ? C8 C11 H11B 110.3 . . ? C4 C11 H11B 110.3 . . ? H11A C11 H11B 108.5 . . ? _diffrn_measured_fraction_theta_max 0.928 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.183 _refine_diff_density_min -0.117 _refine_diff_density_rms 0.027 #===END data_compound1 _database_code_depnum_ccdc_archive 'CCDC 768529' #TrackingRef 'cif.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H12 O2' _chemical_formula_weight 152.19 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.2834(7) _cell_length_b 8.5265(5) _cell_length_c 9.8621(7) _cell_angle_alpha 90.00 _cell_angle_beta 93.062(6) _cell_angle_gamma 90.00 _cell_volume 779.52(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 790 _cell_measurement_theta_min 2.1914 _cell_measurement_theta_max 33.0455 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.288 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 324 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_T_min 0.94553 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET) (compiled Aug 28 2006,13:05:05) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Xcalibur 3' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean 16.1829 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4831 _diffrn_reflns_av_R_equivalents 0.0692 _diffrn_reflns_av_sigmaI/netI 0.1149 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.94 _diffrn_reflns_theta_max 25.02 _reflns_number_total 1373 _reflns_number_gt 619 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET) (compiled Aug 28 2006,13:05:05) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET) (compiled Aug 28 2006,13:05:05) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET) (compiled Aug 28 2006,13:05:05) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0150P)^2^+0.0000P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1373 _refine_ls_number_parameters 102 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1235 _refine_ls_R_factor_gt 0.0394 _refine_ls_wR_factor_ref 0.0633 _refine_ls_wR_factor_gt 0.0528 _refine_ls_goodness_of_fit_ref 0.890 _refine_ls_restrained_S_all 0.890 _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 O1 O 1.10854(18) 0.06297(17) 0.35780(15) 0.0514(5) Uani 1 1 d . . . H1 H 1.1327 0.0814 0.4374 0.062 Uiso 1 1 calc R . . O2 O 0.64585(16) 0.38526(18) 0.13595(17) 0.0544(5) Uani 1 1 d . . . H2 H 0.5732 0.4370 0.1481 0.065 Uiso 1 1 calc R . . C3 C 0.7769(3) 0.3505(2) 0.3534(2) 0.0405(6) Uani 1 1 d . . . H3 H 0.6928 0.3228 0.3945 0.049 Uiso 1 1 calc R . . C4 C 0.7642(2) 0.4431(3) 0.2235(2) 0.0436(7) Uani 1 1 d . . . H4 H 0.7447 0.5528 0.2459 0.052 Uiso 1 1 calc R . . C5 C 0.9322(2) 0.2776(3) 0.0913(2) 0.0443(7) Uani 1 1 d . . . H5 H 0.8827 0.2488 0.0107 0.053 Uiso 1 1 calc R . . C6 C 1.0245(2) 0.1774(3) 0.1488(2) 0.0461(7) Uani 1 1 d . . . H6 H 1.0391 0.0827 0.1048 0.055 Uiso 1 1 calc R . . C7 C 1.1078(2) 0.2066(3) 0.2810(2) 0.0456(7) Uani 1 1 d . . . H7 H 1.2075 0.2321 0.2615 0.055 Uiso 1 1 calc R . . C8 C 0.9019(3) 0.3066(2) 0.4119(2) 0.0419(6) Uani 1 1 d . . . H8 H 0.9014 0.2491 0.4920 0.050 Uiso 1 1 calc R . . C9 C 0.9032(2) 0.4365(3) 0.1501(2) 0.0436(7) Uani 1 1 d . . . H9 H 0.8987 0.5140 0.0766 0.052 Uiso 1 1 calc R . . C10 C 1.0446(2) 0.3453(3) 0.3552(2) 0.0442(7) Uani 1 1 d . . . H10 H 1.1124 0.3773 0.4296 0.053 Uiso 1 1 calc R . . C11 C 1.0263(2) 0.4805(3) 0.2530(2) 0.0487(7) Uani 1 1 d . . . H11A H 1.0032 0.5769 0.2995 0.058 Uiso 1 1 calc R . . H11B H 1.1149 0.4964 0.2069 0.058 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 O1 0.0532(12) 0.0531(11) 0.0470(11) 0.0078(9) -0.0051(10) 0.0057(9) O2 0.0429(11) 0.0610(12) 0.0579(12) -0.0076(9) -0.0098(10) 0.0072(9) C3 0.0473(18) 0.0387(16) 0.0366(17) -0.0014(13) 0.0137(13) -0.0022(13) C4 0.0460(18) 0.0386(16) 0.0459(18) -0.0005(14) 0.0007(14) 0.0041(13) C5 0.0467(18) 0.0513(18) 0.0354(16) -0.0034(14) 0.0071(13) -0.0036(14) C6 0.0455(18) 0.0525(19) 0.0409(18) -0.0084(14) 0.0071(14) 0.0021(14) C7 0.0361(16) 0.0535(17) 0.0476(18) -0.0002(15) 0.0050(13) 0.0007(13) C8 0.0534(18) 0.0394(16) 0.0326(16) -0.0066(12) -0.0007(14) -0.0008(14) C9 0.0498(18) 0.0366(16) 0.0446(16) 0.0106(13) 0.0065(14) 0.0001(13) C10 0.0408(18) 0.0459(17) 0.0448(18) -0.0094(14) -0.0080(13) -0.0035(14) C11 0.0490(19) 0.0416(16) 0.0557(18) 0.0009(14) 0.0038(14) -0.0070(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 O1 C7 1.440(2) . ? O1 H1 0.8200 . ? O2 C4 1.447(2) . ? O2 H2 0.8200 . ? C3 C8 1.322(3) . ? C3 C4 1.504(3) . ? C3 H3 0.9300 . ? C4 C9 1.514(3) . ? C4 H4 0.9800 . ? C5 C6 1.317(3) . ? C5 C9 1.503(3) . ? C5 H5 0.9300 . ? C6 C7 1.500(3) . ? C6 H6 0.9300 . ? C7 C10 1.524(3) . ? C7 H7 0.9800 . ? C8 C10 1.502(3) . ? C8 H8 0.9300 . ? C9 C11 1.534(3) . ? C9 H9 0.9800 . ? C10 C11 1.535(3) . ? C10 H10 0.9800 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? 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 O1 H1 109.5 . . ? C4 O2 H2 109.5 . . ? C8 C3 C4 123.2(2) . . ? C8 C3 H3 118.4 . . ? C4 C3 H3 118.4 . . ? O2 C4 C3 110.60(19) . . ? O2 C4 C9 109.93(19) . . ? C3 C4 C9 110.9(2) . . ? O2 C4 H4 108.4 . . ? C3 C4 H4 108.4 . . ? C9 C4 H4 108.4 . . ? C6 C5 C9 123.0(2) . . ? C6 C5 H5 118.5 . . ? C9 C5 H5 118.5 . . ? C5 C6 C7 124.0(2) . . ? C5 C6 H6 118.0 . . ? C7 C6 H6 118.0 . . ? O1 C7 C6 107.7(2) . . ? O1 C7 C10 113.49(19) . . ? C6 C7 C10 110.6(2) . . ? O1 C7 H7 108.3 . . ? C6 C7 H7 108.3 . . ? C10 C7 H7 108.3 . . ? C3 C8 C10 123.1(2) . . ? C3 C8 H8 118.5 . . ? C10 C8 H8 118.5 . . ? C5 C9 C4 113.14(18) . . ? C5 C9 C11 109.48(19) . . ? C4 C9 C11 107.35(19) . . ? C5 C9 H9 108.9 . . ? C4 C9 H9 108.9 . . ? C11 C9 H9 108.9 . . ? C8 C10 C7 112.24(18) . . ? C8 C10 C11 109.91(19) . . ? C7 C10 C11 107.42(19) . . ? C8 C10 H10 109.1 . . ? C7 C10 H10 109.1 . . ? C11 C10 H10 109.1 . . ? C9 C11 C10 107.63(17) . . ? C9 C11 H11A 110.2 . . ? C10 C11 H11A 110.2 . . ? C9 C11 H11B 110.2 . . ? C10 C11 H11B 110.2 . . ? H11A C11 H11B 108.5 . . ? 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 C8 C3 C4 O2 139.1(2) . . . . ? C8 C3 C4 C9 16.8(3) . . . . ? C9 C5 C6 C7 2.1(4) . . . . ? C5 C6 C7 O1 138.7(2) . . . . ? C5 C6 C7 C10 14.1(3) . . . . ? C4 C3 C8 C10 0.3(3) . . . . ? C6 C5 C9 C4 -101.7(3) . . . . ? C6 C5 C9 C11 18.0(3) . . . . ? O2 C4 C9 C5 -52.6(3) . . . . ? C3 C4 C9 C5 70.1(3) . . . . ? O2 C4 C9 C11 -173.46(18) . . . . ? C3 C4 C9 C11 -50.8(2) . . . . ? C3 C8 C10 C7 -101.5(3) . . . . ? C3 C8 C10 C11 18.0(3) . . . . ? O1 C7 C10 C8 -49.3(3) . . . . ? C6 C7 C10 C8 71.9(3) . . . . ? O1 C7 C10 C11 -170.22(17) . . . . ? C6 C7 C10 C11 -49.0(2) . . . . ? C5 C9 C11 C10 -53.0(2) . . . . ? C4 C9 C11 C10 70.1(2) . . . . ? C8 C10 C11 C9 -52.1(2) . . . . ? C7 C10 C11 C9 70.3(2) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.122 _refine_diff_density_min -0.142 _refine_diff_density_rms 0.033 #===END data_compound3 _database_code_depnum_ccdc_archive 'CCDC 768530' #TrackingRef 'cif.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H6 Br2 O2' _chemical_formula_sum 'C9 H6 Br2 O2' _chemical_formula_weight 305.96 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.3618(7) _cell_length_b 6.6849(5) _cell_length_c 14.6052(11) _cell_angle_alpha 90.00 _cell_angle_beta 107.353(7) _cell_angle_gamma 90.00 _cell_volume 965.62(12) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 894 _cell_measurement_theta_min 2.1344 _cell_measurement_theta_max 33.0452 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.105 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 8.356 _exptl_absorpt_correction_T_min 0.46789 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET) (compiled Aug 28 2006,13:05:05) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Xcalibur 3' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean 16.1829 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5869 _diffrn_reflns_av_R_equivalents 0.0502 _diffrn_reflns_av_sigmaI/netI 0.0901 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 25.02 _reflns_number_total 1678 _reflns_number_gt 592 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET) (compiled Aug 28 2006,13:05:05) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET) (compiled Aug 28 2006,13:05:05) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET) (compiled Aug 28 2006,13:05:05) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1616P)^2^+0.0000P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1678 _refine_ls_number_parameters 118 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1657 _refine_ls_R_factor_gt 0.0710 _refine_ls_wR_factor_ref 0.2735 _refine_ls_wR_factor_gt 0.2302 _refine_ls_goodness_of_fit_ref 0.873 _refine_ls_restrained_S_all 0.873 _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 Br1 Br 0.65082(14) 0.7317(3) 0.19330(13) 0.1369(10) Uani 1 1 d . . . Br2 Br 0.01810(15) 0.7965(3) 0.17957(13) 0.1225(9) Uani 1 1 d . . . C2 C 0.1356(11) 0.7682(18) 0.1016(10) 0.076(3) Uani 1 1 d . . . C3 C 0.4706(11) 0.7348(19) 0.1111(9) 0.079(4) Uani 1 1 d . . . C5 C 0.2379(16) 0.7240(19) -0.0466(10) 0.098(4) Uani 1 1 d . . . H5A H 0.2970 0.7162 -0.0869 0.117 Uiso 1 1 calc R . . H5B H 0.1450 0.7187 -0.0874 0.117 Uiso 1 1 calc R . . O21 O 0.1218(9) 0.4159(15) 0.1086(8) 0.124(4) Uani 1 1 d . . . C11 C 0.2655(15) 0.555(2) 0.0225(11) 0.102(4) Uani 1 1 d . . . H11 H 0.2516 0.4293 -0.0138 0.122 Uiso 1 1 calc R . . C12 C 0.4118(14) 0.923(2) 0.0809(11) 0.106(5) Uani 1 1 d . . . C13 C 0.2621(17) 0.912(2) 0.0087(14) 0.131(6) Uani 1 1 d . . . H13 H 0.2460 1.0268 -0.0352 0.157 Uiso 1 1 calc R . . C15 C 0.4032(13) 0.560(2) 0.0840(9) 0.095(4) Uani 1 1 d . . . H15 H 0.4472 0.4403 0.1058 0.114 Uiso 1 1 calc R . . O20 O 0.4732(10) 1.0789(17) 0.0962(10) 0.159(5) Uani 1 1 d . . . C1 C 0.1672(12) 0.561(2) 0.0815(9) 0.090(4) Uani 1 1 d . . . C4 C 0.1804(14) 0.927(2) 0.0688(11) 0.107(5) Uani 1 1 d . . . H4 H 0.1572 1.0528 0.0859 0.128 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 Br1 0.0671(11) 0.229(2) 0.1118(15) 0.0056(11) 0.0230(9) 0.0103(10) Br2 0.0764(11) 0.1745(18) 0.1184(15) -0.0136(10) 0.0319(9) 0.0128(9) C2 0.054(7) 0.078(9) 0.091(9) 0.006(7) 0.015(6) 0.008(6) C3 0.053(7) 0.104(10) 0.093(10) -0.023(8) 0.041(6) -0.013(7) C5 0.109(11) 0.095(10) 0.084(10) -0.014(8) 0.019(8) -0.008(8) O21 0.102(7) 0.088(6) 0.197(10) 0.040(7) 0.069(7) 0.001(5) C11 0.094(11) 0.082(9) 0.127(12) -0.042(9) 0.027(10) -0.019(8) C12 0.079(10) 0.067(9) 0.160(14) -0.032(9) 0.016(9) 0.011(8) C13 0.111(13) 0.097(11) 0.178(17) 0.050(12) 0.032(13) 0.021(10) C15 0.078(10) 0.115(11) 0.100(11) 0.002(8) 0.039(8) 0.008(8) O20 0.114(8) 0.102(7) 0.274(15) -0.072(9) 0.078(9) -0.027(7) C1 0.074(9) 0.105(12) 0.094(10) 0.009(8) 0.028(7) -0.007(8) C4 0.105(12) 0.092(11) 0.133(14) 0.000(9) 0.050(10) 0.003(9) _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 Br1 C3 1.895(12) . ? Br2 C2 1.908(14) . ? C2 C4 1.305(17) . ? C2 C1 1.473(17) . ? C3 C15 1.357(15) . ? C3 C12 1.410(17) . ? C5 C13 1.48(2) . ? C5 C11 1.487(18) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? O21 C1 1.196(14) . ? C11 C15 1.442(17) . ? C11 C1 1.517(17) . ? C11 H11 0.9800 . ? C12 O20 1.206(15) . ? C12 C13 1.60(2) . ? C13 C4 1.393(19) . ? C13 H13 0.9800 . ? C15 H15 0.9300 . ? C4 H4 0.9300 . ? 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 C4 C2 C1 124.5(13) . . ? C4 C2 Br2 119.9(11) . . ? C1 C2 Br2 115.6(10) . . ? C15 C3 C12 122.6(13) . . ? C15 C3 Br1 120.0(10) . . ? C12 C3 Br1 117.4(10) . . ? C13 C5 C11 108.1(13) . . ? C13 C5 H5A 110.1 . . ? C11 C5 H5A 110.1 . . ? C13 C5 H5B 110.1 . . ? C11 C5 H5B 110.1 . . ? H5A C5 H5B 108.4 . . ? C15 C11 C5 110.9(12) . . ? C15 C11 C1 110.7(12) . . ? C5 C11 C1 109.8(12) . . ? C15 C11 H11 108.4 . . ? C5 C11 H11 108.4 . . ? C1 C11 H11 108.4 . . ? O20 C12 C3 123.9(14) . . ? O20 C12 C13 121.1(14) . . ? C3 C12 C13 114.3(12) . . ? C4 C13 C5 111.6(14) . . ? C4 C13 C12 103.5(16) . . ? C5 C13 C12 111.9(12) . . ? C4 C13 H13 109.9 . . ? C5 C13 H13 109.9 . . ? C12 C13 H13 109.9 . . ? C3 C15 C11 122.1(13) . . ? C3 C15 H15 119.0 . . ? C11 C15 H15 119.0 . . ? O21 C1 C2 124.3(13) . . ? O21 C1 C11 124.2(13) . . ? C2 C1 C11 111.5(12) . . ? C2 C4 C13 121.6(14) . . ? C2 C4 H4 119.2 . . ? C13 C4 H4 119.2 . . ? 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 C13 C5 C11 C15 -59.6(17) . . . . ? C13 C5 C11 C1 63.0(15) . . . . ? C15 C3 C12 O20 -172.6(14) . . . . ? Br1 C3 C12 O20 7.9(19) . . . . ? C15 C3 C12 C13 -3(2) . . . . ? Br1 C3 C12 C13 177.7(11) . . . . ? C11 C5 C13 C4 -58.7(17) . . . . ? C11 C5 C13 C12 56.8(19) . . . . ? O20 C12 C13 C4 -96.1(17) . . . . ? C3 C12 C13 C4 93.7(15) . . . . ? O20 C12 C13 C5 143.6(15) . . . . ? C3 C12 C13 C5 -27(2) . . . . ? C12 C3 C15 C11 0(2) . . . . ? Br1 C3 C15 C11 179.2(11) . . . . ? C5 C11 C15 C3 32.3(18) . . . . ? C1 C11 C15 C3 -89.9(15) . . . . ? C4 C2 C1 O21 -177.0(14) . . . . ? Br2 C2 C1 O21 1.9(16) . . . . ? C4 C2 C1 C11 3.4(18) . . . . ? Br2 C2 C1 C11 -177.7(9) . . . . ? C15 C11 C1 O21 -92.2(16) . . . . ? C5 C11 C1 O21 145.0(13) . . . . ? C15 C11 C1 C2 87.4(14) . . . . ? C5 C11 C1 C2 -35.4(14) . . . . ? C1 C2 C4 C13 1(2) . . . . ? Br2 C2 C4 C13 -177.5(12) . . . . ? C5 C13 C4 C2 27(2) . . . . ? C12 C13 C4 C2 -93.7(17) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.908 _refine_diff_density_min -0.848 _refine_diff_density_rms 0.113 #===END data_compound4 _database_code_depnum_ccdc_archive 'CCDC 768531' #TrackingRef 'cif.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H10 N2' _chemical_formula_weight 170.21 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_space_group_name_H-M 'P 21 21 2' _symmetry_cell_setting orthorhombic loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/2, y+1/2, -z' 'x+1/2, -y+1/2, -z' _cell_length_a 7.3655(5) _cell_length_b 11.7786(9) _cell_length_c 5.5546(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 481.89(6) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 859 _cell_measurement_theta_min 3.2589 _cell_measurement_theta_max 32.9688 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.173 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 180 _exptl_absorpt_coefficient_mu 0.071 _exptl_absorpt_correction_T_min 0.80547 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET) (compiled Aug 28 2006,13:05:05) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Xcalibur 3' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean 16.1829 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3059 _diffrn_reflns_av_R_equivalents 0.0238 _diffrn_reflns_av_sigmaI/netI 0.0304 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 2 _diffrn_reflns_theta_min 3.26 _diffrn_reflns_theta_max 25.02 _reflns_number_total 519 _reflns_number_gt 285 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET) (compiled Aug 28 2006,13:05:05) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET) (compiled Aug 28 2006,13:05:05) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET) (compiled Aug 28 2006,13:05:05) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0387P)^2^+0.0000P] 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 riding _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 10(10) _refine_ls_number_reflns 519 _refine_ls_number_parameters 60 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0544 _refine_ls_R_factor_gt 0.0310 _refine_ls_wR_factor_ref 0.0727 _refine_ls_wR_factor_gt 0.0667 _refine_ls_goodness_of_fit_ref 0.918 _refine_ls_restrained_S_all 0.918 _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 C1 C 0.0638(3) 0.8723(2) 0.1486(4) 0.0734(7) Uani 1 1 d . . . C2 C 0.2105(3) 0.9321(2) 0.2011(4) 0.0783(7) Uani 1 1 d . . . H2 H 0.2952 0.9016 0.3071 0.094 Uiso 1 1 calc R . . C3 C 0.0314(3) 0.7667(2) 0.2731(5) 0.0941(8) Uani 1 1 d . . . C4 C -0.0771(3) 0.90768(19) -0.0301(4) 0.0845(7) Uani 1 1 d . . . H4 H -0.1116 0.8421 -0.1287 0.101 Uiso 1 1 calc R . . C5 C 0.2450(3) 1.04613(19) 0.0973(4) 0.0947(8) Uani 1 1 d . . . H5A H 0.3446 1.0415 -0.0164 0.114 Uiso 1 1 calc R . . H5B H 0.2802 1.0979 0.2248 0.114 Uiso 1 1 calc R . . C6 C 0.0000 1.0000 -0.1915(6) 0.0965(12) Uani 1 2 d S . . H6A H 0.0947 0.9691 -0.2936 0.116 Uiso 0.50 1 calc PR . . H6B H -0.0947 1.0309 -0.2936 0.116 Uiso 0.50 1 calc PR . . N7 N 0.0030(3) 0.6837(2) 0.3706(4) 0.1350(11) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0697(15) 0.0803(17) 0.0701(15) -0.0016(13) 0.0157(14) 0.0115(14) C2 0.0575(14) 0.0976(17) 0.0797(14) 0.0104(15) 0.0027(13) 0.0221(14) C3 0.0916(18) 0.0894(18) 0.1013(19) 0.0058(17) 0.0315(16) 0.0213(16) C4 0.0855(18) 0.0910(19) 0.0770(14) -0.0213(14) -0.0115(15) 0.0036(14) C5 0.0580(14) 0.1118(18) 0.114(2) 0.0158(16) 0.0068(16) 0.0039(14) C6 0.111(3) 0.123(3) 0.0554(18) 0.000 0.000 0.025(2) N7 0.139(2) 0.1042(17) 0.162(2) 0.0327(17) 0.0577(19) 0.0145(15) _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 C1 C2 1.323(3) . ? C1 C3 1.442(3) . ? C1 C4 1.496(3) . ? C2 C5 1.483(3) . ? C2 H2 0.9300 . ? C3 N7 1.137(3) . ? C4 C6 1.520(3) . ? C4 C5 1.525(3) 2_575 ? C4 H4 0.9800 . ? C5 C4 1.525(3) 2_575 ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C4 1.520(3) 2_575 ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? 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 C2 C1 C3 119.3(2) . . ? C2 C1 C4 124.4(2) . . ? C3 C1 C4 116.3(2) . . ? C1 C2 C5 122.5(2) . . ? C1 C2 H2 118.8 . . ? C5 C2 H2 118.8 . . ? N7 C3 C1 178.9(3) . . ? C1 C4 C6 109.4(2) . . ? C1 C4 C5 110.73(18) . 2_575 ? C6 C4 C5 108.77(18) . 2_575 ? C1 C4 H4 109.3 . . ? C6 C4 H4 109.3 . . ? C5 C4 H4 109.3 2_575 . ? C2 C5 C4 111.39(18) . 2_575 ? C2 C5 H5A 109.4 . . ? C4 C5 H5A 109.4 2_575 . ? C2 C5 H5B 109.4 . . ? C4 C5 H5B 109.4 2_575 . ? H5A C5 H5B 108.0 . . ? C4 C6 C4 107.7(2) 2_575 . ? C4 C6 H6A 110.2 2_575 . ? C4 C6 H6A 110.2 . . ? C4 C6 H6B 110.2 2_575 . ? C4 C6 H6B 110.2 . . ? H6A C6 H6B 108.5 . . ? 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 C3 C1 C2 C5 -174.4(2) . . . . ? C4 C1 C2 C5 4.0(3) . . . . ? C2 C1 C3 N7 155(14) . . . . ? C4 C1 C3 N7 -24(14) . . . . ? C2 C1 C4 C6 17.1(3) . . . . ? C3 C1 C4 C6 -164.38(18) . . . . ? C2 C1 C4 C5 -102.7(3) . . . 2_575 ? C3 C1 C4 C5 75.8(2) . . . 2_575 ? C1 C2 C5 C4 11.4(3) . . . 2_575 ? C1 C4 C6 C4 -52.08(12) . . . 2_575 ? C5 C4 C6 C4 68.97(14) 2_575 . . 2_575 ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.056 _refine_diff_density_min -0.087 _refine_diff_density_rms 0.020 #===END