# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full J.Mater.Chem. _journal_coden_cambridge 1145 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Ren-Gen Xiong' _publ_contact_author_email xiongrg@seu.edu.cn loop_ _publ_author_name 'Ren-Gen Xiong.' 'Yi Zhang.' K.Awaga data_1 _database_code_depnum_ccdc_archive 'CCDC 865148' #TrackingRef '- 383k.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H11 Cl N O4' _chemical_formula_sum 'C9 H11 Cl N O4' _chemical_formula_weight 232.64 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' Cl Cl 0.1484 0.1585 '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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/m ' _symmetry_space_group_name_Hall '-P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x, -y, -z' 'x, -y-1/2, z' _cell_length_a 8.9084(18) _cell_length_b 7.2253(18) _cell_length_c 9.172(3) _cell_angle_alpha 90.00 _cell_angle_beta 95.55(3) _cell_angle_gamma 90.00 _cell_volume 587.6(3) _cell_formula_units_Z 2 _cell_measurement_temperature 383(2) _cell_measurement_reflns_used 2394 _cell_measurement_theta_min 3.275 _cell_measurement_theta_max 27.785 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.2000 _exptl_crystal_size_mid 0.2000 _exptl_crystal_size_min 0.2000 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.315 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 242 _exptl_absorpt_coefficient_mu 0.319 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.938 _exptl_absorpt_correction_T_max 0.938 _exptl_absorpt_process_details 'CrystalClear (Rigaku, 2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 383(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 'Rigaku SCXmini diffractometer' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 13.6612 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 4349 _diffrn_reflns_av_R_equivalents 0.0241 _diffrn_reflns_av_sigmaI/netI 0.0208 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.04 _diffrn_reflns_theta_max 24.49 _reflns_number_total 1066 _reflns_number_gt 760 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku, 2005)' _computing_cell_refinement 'CrystalClear (Rigaku, 2005)' _computing_data_reduction 'CrystalClear (Rigaku, 2005)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'diamond (Brandenburg & Putz, 2005)' _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^)+(0.2000P)^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 contr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1066 _refine_ls_number_parameters 115 _refine_ls_number_restraints 40 _refine_ls_R_factor_all 0.0806 _refine_ls_R_factor_gt 0.0630 _refine_ls_wR_factor_ref 0.2401 _refine_ls_wR_factor_gt 0.2130 _refine_ls_goodness_of_fit_ref 0.970 _refine_ls_restrained_S_all 0.961 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.001 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 N1 N 0.6640(4) 0.7500 0.1691(3) 0.1091(10) Uani 1 2 d S . . H1A H 0.6999 0.6978 0.1182 0.164 Uiso 1 1 d R . . H1B H 0.5572 0.7500 0.1497 0.164 Uiso 1 2 d SR . . C1 C 0.7013(4) 0.7500 0.3280(4) 0.0873(9) Uani 1 2 d S . . C2 C 0.5838(4) 0.7500 0.4163(4) 0.0959(10) Uani 1 2 d S . . C3 C 0.6223(4) 0.7500 0.5654(5) 0.1035(11) Uani 1 2 d S . . H3A H 0.5459 0.7500 0.6277 0.124 Uiso 1 2 calc SR . . C4 C 0.7721(5) 0.7500 0.6264(4) 0.0986(10) Uani 1 2 d S . . C5 C 0.8828(4) 0.7500 0.5332(4) 0.1028(11) Uani 1 2 d S . . H5A H 0.9829 0.7500 0.5728 0.123 Uiso 1 2 calc SR . . C6 C 0.8519(4) 0.7500 0.3819(4) 0.0932(10) Uani 1 2 d S . . C7 C 0.4195(5) 0.7500 0.3556(6) 0.1368(18) Uani 1 2 d S . . H7A H 0.3548 0.7500 0.4335 0.205 Uiso 1 2 d SR . . H7B H 0.4001 0.8585 0.2963 0.205 Uiso 0.50 1 d PR . . C8 C 0.8087(7) 0.7500 0.7903(5) 0.1401(18) Uani 1 2 d S . . H8A H 0.9160 0.7500 0.8146 0.210 Uiso 1 2 d SR . . H8B H 0.7660 0.8585 0.8304 0.210 Uiso 0.50 1 d PR . . C9 C 0.9773(5) 0.7500 0.2812(6) 0.1344(16) Uani 1 2 d S . . H9A H 1.0730 0.7500 0.3391 0.202 Uiso 1 2 d SR . . H9B H 0.9693 0.6415 0.2205 0.202 Uiso 0.50 1 d PR . . Cl1 Cl 0.70593(10) 0.2500 0.09900(11) 0.1022(4) Uani 1 2 d S . . O1 O 0.5699(6) 0.3463(8) 0.0814(8) 0.199(3) Uani 0.50 1 d P . . O3 O 0.7363(8) 0.2500 0.2522(6) 0.186(4) Uani 0.64 2 d SPU . . O2 O 0.714(3) 0.2500 -0.057(2) 0.303(14) Uani 0.30 2 d SPU . . O4 O 0.8156(8) 0.1238(13) 0.0868(14) 0.217(5) Uani 0.35 1 d PU . . O3' O 0.735(3) 0.1439(17) 0.2038(19) 0.192(8) Uani 0.18 1 d PU . . O1' O 0.7273(15) 0.0994(7) 0.0264(8) 0.240(4) Uani 0.50 1 d PU . . 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 N1 0.138(2) 0.0841(17) 0.100(2) 0.000 -0.0120(18) 0.000 C1 0.0925(19) 0.0611(15) 0.105(2) 0.000 -0.0083(17) 0.000 C2 0.0890(19) 0.0769(18) 0.118(3) 0.000 -0.0092(19) 0.000 C3 0.099(2) 0.093(2) 0.120(3) 0.000 0.020(2) 0.000 C4 0.105(2) 0.090(2) 0.099(2) 0.000 -0.0009(18) 0.000 C5 0.093(2) 0.096(2) 0.115(3) 0.000 -0.012(2) 0.000 C6 0.090(2) 0.0796(18) 0.109(3) 0.000 0.0103(17) 0.000 C7 0.086(2) 0.133(4) 0.185(5) 0.000 -0.019(3) 0.000 C8 0.162(4) 0.152(4) 0.102(3) 0.000 -0.011(3) 0.000 C9 0.106(3) 0.150(4) 0.150(4) 0.000 0.026(3) 0.000 Cl1 0.1030(7) 0.0763(6) 0.1226(8) 0.000 -0.0134(5) 0.000 O1 0.144(4) 0.160(5) 0.275(6) -0.001(4) -0.065(4) 0.032(3) O3 0.170(5) 0.283(11) 0.102(4) 0.000 -0.011(4) 0.000 O2 0.35(3) 0.45(4) 0.123(10) 0.000 0.085(14) 0.000 O4 0.116(4) 0.192(7) 0.332(13) -0.089(8) -0.030(6) 0.081(4) O3' 0.33(2) 0.069(6) 0.159(10) 0.067(7) -0.051(12) 0.007(9) O1' 0.491(13) 0.076(3) 0.173(5) -0.036(3) 0.131(7) -0.011(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 N1 C1 1.463(5) . ? N1 H1A 0.7015 . ? N1 H1B 0.9509 . ? C1 C2 1.384(5) . ? C1 C6 1.384(5) . ? C2 C3 1.378(5) . ? C2 C7 1.514(5) . ? C3 C4 1.396(6) . ? C3 H3A 0.9300 . ? C4 C5 1.366(6) . ? C4 C8 1.507(6) . ? C5 C6 1.389(5) . ? C5 H5A 0.9300 . ? C6 C9 1.517(6) . ? C7 H7A 0.9601 . ? C7 H7B 0.9600 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9601 . ? Cl1 O3' 1.237(13) 4_565 ? Cl1 O3' 1.237(13) . ? Cl1 O1' 1.299(6) . ? Cl1 O1' 1.299(6) 4_565 ? Cl1 O4 1.349(7) 4_565 ? Cl1 O4 1.349(7) . ? Cl1 O1 1.393(5) 4_565 ? Cl1 O1 1.393(5) . ? Cl1 O3 1.405(6) . ? Cl1 O2 1.443(18) . ? O1 O1 1.392(12) 4_565 ? O1 O1' 1.585(12) 4_565 ? O1 O3' 1.76(2) 4_565 ? O3 O3' 0.886(16) . ? O3 O3' 0.886(16) 4_565 ? O2 O1' 1.331(11) 4_565 ? O2 O1' 1.331(11) . ? O2 O4 1.78(2) 4_565 ? O2 O4 1.78(2) . ? O4 O1' 0.934(13) . ? O4 O3' 1.36(2) . ? O3' O3' 1.53(2) 4_565 ? O3' O1' 1.65(2) . ? O3' O1 1.76(2) 4_565 ? O1' O1 1.585(12) 4_565 ? 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 C1 N1 H1A 126.1 . . ? C1 N1 H1B 108.3 . . ? H1A N1 H1B 112.8 . . ? C2 C1 C6 123.6(3) . . ? C2 C1 N1 118.1(3) . . ? C6 C1 N1 118.3(3) . . ? C1 C2 C3 116.8(3) . . ? C1 C2 C7 123.0(4) . . ? C3 C2 C7 120.3(4) . . ? C2 C3 C4 122.3(4) . . ? C2 C3 H3A 118.8 . . ? C4 C3 H3A 118.8 . . ? C5 C4 C3 118.0(4) . . ? C5 C4 C8 121.6(4) . . ? C3 C4 C8 120.4(4) . . ? C4 C5 C6 122.7(4) . . ? C4 C5 H5A 118.7 . . ? C6 C5 H5A 118.7 . . ? C1 C6 C5 116.6(3) . . ? C1 C6 C9 121.9(4) . . ? C5 C6 C9 121.5(4) . . ? C2 C7 H7A 110.8 . . ? C2 C7 H7B 108.8 . . ? H7A C7 H7B 109.5 . . ? C4 C8 H8A 110.3 . . ? C4 C8 H8B 109.1 . . ? H8A C8 H8B 109.5 . . ? C6 C9 H9A 109.3 . . ? C6 C9 H9B 109.6 . . ? H9A C9 H9B 109.5 . . ? O3' Cl1 O3' 76.6(15) 4_565 . ? O3' Cl1 O1' 152.5(10) 4_565 . ? O3' Cl1 O1' 81.3(9) . . ? O3' Cl1 O1' 81.3(9) 4_565 4_565 ? O3' Cl1 O1' 152.5(10) . 4_565 ? O1' Cl1 O1' 113.7(6) . 4_565 ? O3' Cl1 O4 63.1(11) 4_565 4_565 ? O3' Cl1 O4 112.6(11) . 4_565 ? O1' Cl1 O4 112.3(7) . 4_565 ? O1' Cl1 O4 41.3(6) 4_565 4_565 ? O3' Cl1 O4 112.6(11) 4_565 . ? O3' Cl1 O4 63.1(11) . . ? O1' Cl1 O4 41.3(6) . . ? O1' Cl1 O4 112.3(7) 4_565 . ? O4 Cl1 O4 85.0(8) 4_565 . ? O3' Cl1 O1 120.9(12) 4_565 4_565 ? O3' Cl1 O1 83.9(11) . 4_565 ? O1' Cl1 O1 72.0(6) . 4_565 ? O1' Cl1 O1 121.9(6) 4_565 4_565 ? O4 Cl1 O1 163.1(5) 4_565 4_565 ? O4 Cl1 O1 106.4(5) . 4_565 ? O3' Cl1 O1 83.9(11) 4_565 . ? O3' Cl1 O1 120.9(12) . . ? O1' Cl1 O1 121.9(6) . . ? O1' Cl1 O1 72.0(6) 4_565 . ? O4 Cl1 O1 106.4(5) 4_565 . ? O4 Cl1 O1 163.1(5) . . ? O1 Cl1 O1 59.9(5) 4_565 . ? O3' Cl1 O3 38.5(8) 4_565 . ? O3' Cl1 O3 38.5(8) . . ? O1' Cl1 O3 119.3(4) . . ? O1' Cl1 O3 119.3(4) 4_565 . ? O4 Cl1 O3 90.7(6) 4_565 . ? O4 Cl1 O3 90.7(6) . . ? O1 Cl1 O3 101.4(4) 4_565 . ? O1 Cl1 O3 101.4(4) . . ? O3' Cl1 O2 138.2(10) 4_565 . ? O3' Cl1 O2 138.2(10) . . ? O1' Cl1 O2 57.8(4) . . ? O1' Cl1 O2 57.8(4) 4_565 . ? O4 Cl1 O2 79.2(10) 4_565 . ? O4 Cl1 O2 79.2(10) . . ? O1 Cl1 O2 90.5(10) 4_565 . ? O1 Cl1 O2 90.5(10) . . ? O3 Cl1 O2 166.3(12) . . ? O1 O1 Cl1 60.0(2) 4_565 . ? O1 O1 O1' 104.3(3) 4_565 4_565 ? Cl1 O1 O1' 51.2(3) . 4_565 ? O1 O1 O3' 92.3(4) 4_565 4_565 ? Cl1 O1 O3' 44.3(5) . 4_565 ? O1' O1 O3' 58.9(8) 4_565 4_565 ? O3' O3 O3' 120(2) . 4_565 ? O3' O3 Cl1 60.4(10) . . ? O3' O3 Cl1 60.4(10) 4_565 . ? O1' O2 O1' 109.7(14) 4_565 . ? O1' O2 Cl1 55.7(7) 4_565 . ? O1' O2 Cl1 55.7(7) . . ? O1' O2 O4 30.8(8) 4_565 4_565 ? O1' O2 O4 88.7(12) . 4_565 ? Cl1 O2 O4 48.1(7) . 4_565 ? O1' O2 O4 88.7(12) 4_565 . ? O1' O2 O4 30.8(8) . . ? Cl1 O2 O4 48.1(7) . . ? O4 O2 O4 61.6(10) 4_565 . ? O1' O4 Cl1 66.5(6) . . ? O1' O4 O3' 90.5(13) . . ? Cl1 O4 O3' 54.4(7) . . ? O1' O4 O2 46.9(9) . . ? Cl1 O4 O2 52.7(7) . . ? O3' O4 O2 105.2(11) . . ? O3 O3' Cl1 81.0(9) . . ? O3 O3' O4 120.5(19) . . ? Cl1 O3' O4 62.5(9) . . ? O3 O3' O3' 30.0(11) . 4_565 ? Cl1 O3' O3' 51.7(8) . 4_565 ? O4 O3' O3' 96.1(6) . 4_565 ? O3 O3' O1' 131.2(12) . . ? Cl1 O3' O1' 51.0(7) . . ? O4 O3' O1' 34.4(7) . . ? O3' O3' O1' 101.2(4) 4_565 . ? O3 O3' O1 104.7(17) . 4_565 ? Cl1 O3' O1 51.8(7) . 4_565 ? O4 O3' O1 88.5(10) . 4_565 ? O3' O3' O1 87.7(4) 4_565 4_565 ? O1' O3' O1 55.1(7) . 4_565 ? O4 O1' Cl1 72.2(7) . . ? O4 O1' O2 102.3(15) . . ? Cl1 O1' O2 66.5(7) . . ? O4 O1' O1 119.0(10) . 4_565 ? Cl1 O1' O1 56.7(4) . 4_565 ? O2 O1' O1 87.0(13) . 4_565 ? O4 O1' O3' 55.1(11) . . ? Cl1 O1' O3' 47.7(5) . . ? O2 O1' O3' 113.7(8) . . ? O1 O1' O3' 65.9(9) 4_565 . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 24.49 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.239 _refine_diff_density_min -0.222 _refine_diff_density_rms 0.045 # Attachment '- RT.cif' data_2 _database_code_depnum_ccdc_archive 'CCDC 865149' #TrackingRef '- RT.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H14 N Cl O4' _chemical_formula_sum 'C9 H14 Cl N O4' _chemical_formula_weight 235.66 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' Cl Cl 0.1484 0.1585 '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 _symmetry_space_group_name_Hall '-P1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.1581(14) _cell_length_b 8.5937(17) _cell_length_c 9.0642(18) _cell_angle_alpha 88.74(3) _cell_angle_beta 79.19(3) _cell_angle_gamma 87.02(3) _cell_volume 546.90(19) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2394 _cell_measurement_theta_min 3.275 _cell_measurement_theta_max 27.785 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.2000 _exptl_crystal_size_mid 0.2000 _exptl_crystal_size_min 0.2000 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.431 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 248 _exptl_absorpt_coefficient_mu 0.344 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.934 _exptl_absorpt_correction_T_max 0.934 _exptl_absorpt_process_details 'CrystalClear (Rigaku, 2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Rigaku SCXmini diffractometer' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 13.6612 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 5745 _diffrn_reflns_av_R_equivalents 0.0320 _diffrn_reflns_av_sigmaI/netI 0.0403 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.28 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2506 _reflns_number_gt 1903 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku, 2005)' _computing_cell_refinement 'CrystalClear (Rigaku, 2005)' _computing_data_reduction 'CrystalClear (Rigaku, 2005)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'diamond (Brandenburg & Putz, 2005)' _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^)+(0.1168P)^2^+0.3680P] 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 contr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.12(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2506 _refine_ls_number_parameters 140 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.0979 _refine_ls_R_factor_gt 0.0790 _refine_ls_wR_factor_ref 0.2151 _refine_ls_wR_factor_gt 0.2001 _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_restrained_S_all 1.359 _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 Cl1 Cl 0.22851(14) 0.31825(12) 0.08293(12) 0.0473(4) Uani 1 1 d U . . C1 C 0.7272(5) 0.3034(5) 0.3230(5) 0.0412(9) Uani 1 1 d . . . N1 N 0.7106(5) 0.3526(4) 0.1709(4) 0.0491(9) Uani 1 1 d . . . H1A H 0.7138 0.4559 0.1631 0.074 Uiso 1 1 calc R . . H1B H 0.6009 0.3227 0.1508 0.074 Uiso 1 1 calc R . . H1C H 0.8069 0.3094 0.1058 0.074 Uiso 1 1 calc R . . C5 C 0.7701(6) 0.3609(5) 0.5660(5) 0.0461(10) Uani 1 1 d . . . H5A H 0.7855 0.4329 0.6374 0.055 Uiso 1 1 calc R . . C6 C 0.7490(5) 0.4136(5) 0.4253(5) 0.0415(9) Uani 1 1 d . . . O4 O 0.1332(6) 0.4666(4) 0.1136(4) 0.0673(10) Uani 1 1 d . . . O3 O 0.0962(5) 0.2129(4) 0.0524(4) 0.0686(10) Uani 1 1 d . . . C2 C 0.7249(6) 0.1453(5) 0.3559(5) 0.0453(10) Uani 1 1 d . . . C4 C 0.7691(6) 0.2043(5) 0.6048(5) 0.0487(10) Uani 1 1 d . . . C3 C 0.7461(6) 0.0994(5) 0.4974(5) 0.0505(10) Uani 1 1 d . . . H3A H 0.7450 -0.0062 0.5221 0.061 Uiso 1 1 calc R . . O2 O 0.3067(7) 0.2682(5) 0.2078(6) 0.0908(14) Uani 1 1 d . . . C9 C 0.7498(7) 0.5856(5) 0.3891(6) 0.0540(11) Uani 1 1 d . . . H9A H 0.7754 0.6412 0.4733 0.081 Uiso 1 1 calc R . . H9B H 0.6279 0.6208 0.3682 0.081 Uiso 1 1 calc R . . H9C H 0.8468 0.6043 0.3028 0.081 Uiso 1 1 calc R . . O1 O 0.3763(5) 0.3356(4) -0.0437(5) 0.0696(7) Uani 1 1 d U . . C7 C 0.7009(8) 0.0279(5) 0.2405(6) 0.0611(13) Uani 1 1 d . . . H7A H 0.6945 -0.0743 0.2857 0.092 Uiso 1 1 calc R . . H7B H 0.8074 0.0295 0.1585 0.092 Uiso 1 1 calc R . . H7C H 0.5855 0.0536 0.2039 0.092 Uiso 1 1 calc R . . C8 C 0.7927(8) 0.1515(7) 0.7590(6) 0.0673(14) Uani 1 1 d . . . H8A H 0.8440 0.0459 0.7554 0.101 Uiso 1 1 calc R . . H8B H 0.6712 0.1573 0.8254 0.101 Uiso 1 1 calc R . . H8C H 0.8781 0.2175 0.7951 0.101 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 Cl1 0.0371(6) 0.0497(6) 0.0570(7) 0.0013(4) -0.0132(4) -0.0038(4) C1 0.0290(18) 0.044(2) 0.050(2) 0.0011(17) -0.0057(16) -0.0064(15) N1 0.0396(18) 0.057(2) 0.053(2) 0.0031(16) -0.0125(16) -0.0097(16) C5 0.037(2) 0.048(2) 0.055(2) -0.0067(18) -0.0098(18) -0.0045(17) C6 0.0290(18) 0.0381(19) 0.057(2) 0.0003(17) -0.0060(16) -0.0046(14) O4 0.071(2) 0.056(2) 0.075(2) -0.0049(17) -0.0171(19) 0.0082(17) O3 0.057(2) 0.068(2) 0.085(3) -0.0139(18) -0.0177(19) -0.0160(17) C2 0.040(2) 0.038(2) 0.058(2) -0.0041(17) -0.0072(18) -0.0054(16) C4 0.036(2) 0.054(2) 0.055(3) 0.007(2) -0.0082(18) -0.0028(18) C3 0.046(2) 0.039(2) 0.066(3) 0.0036(19) -0.008(2) -0.0046(17) O2 0.093(3) 0.085(3) 0.110(3) 0.022(2) -0.063(3) -0.004(2) C9 0.048(2) 0.041(2) 0.073(3) 0.001(2) -0.009(2) -0.0037(18) O1 0.0527(12) 0.0675(12) 0.0816(13) 0.0019(11) 0.0050(11) -0.0019(11) C7 0.064(3) 0.045(2) 0.076(3) -0.013(2) -0.015(3) -0.008(2) C8 0.068(3) 0.075(3) 0.063(3) 0.016(3) -0.022(3) -0.010(3) _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 Cl1 O2 1.403(4) . ? Cl1 O3 1.411(3) . ? Cl1 O1 1.419(4) . ? Cl1 O4 1.422(4) . ? C1 C6 1.375(6) . ? C1 C2 1.385(6) . ? C1 N1 1.458(5) . ? N1 H1A 0.8900 . ? N1 H1B 0.8900 . ? N1 H1C 0.8900 . ? C5 C6 1.376(6) . ? C5 C4 1.383(6) . ? C5 H5A 0.9300 . ? C6 C9 1.507(6) . ? C2 C3 1.367(6) . ? C2 C7 1.508(6) . ? C4 C3 1.379(7) . ? C4 C8 1.497(6) . ? C3 H3A 0.9300 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? 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 O2 Cl1 O3 111.0(3) . . ? O2 Cl1 O1 109.7(3) . . ? O3 Cl1 O1 110.6(2) . . ? O2 Cl1 O4 109.0(3) . . ? O3 Cl1 O4 108.7(2) . . ? O1 Cl1 O4 107.8(2) . . ? C6 C1 C2 123.1(4) . . ? C6 C1 N1 119.3(4) . . ? C2 C1 N1 117.6(4) . . ? C1 N1 H1A 109.5 . . ? C1 N1 H1B 109.5 . . ? H1A N1 H1B 109.5 . . ? C1 N1 H1C 109.5 . . ? H1A N1 H1C 109.5 . . ? H1B N1 H1C 109.5 . . ? C6 C5 C4 122.2(4) . . ? C6 C5 H5A 118.9 . . ? C4 C5 H5A 118.9 . . ? C1 C6 C5 117.1(4) . . ? C1 C6 C9 122.8(4) . . ? C5 C6 C9 120.1(4) . . ? C3 C2 C1 117.3(4) . . ? C3 C2 C7 121.1(4) . . ? C1 C2 C7 121.5(4) . . ? C3 C4 C5 118.0(4) . . ? C3 C4 C8 121.4(4) . . ? C5 C4 C8 120.6(4) . . ? C2 C3 C4 122.2(4) . . ? C2 C3 H3A 118.9 . . ? C4 C3 H3A 118.9 . . ? C6 C9 H9A 109.5 . . ? C6 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C6 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C2 C7 H7A 109.5 . . ? C2 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C2 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C4 C8 H8A 109.5 . . ? C4 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C4 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? 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 N1 H1A O1 0.89 2.20 2.976(5) 144.9 2_665 N1 H1C O3 0.89 2.16 2.969(5) 150.5 1_655 N1 H1B O2 0.89 2.15 2.974(6) 154.4 . _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.850 _refine_diff_density_min -1.036 _refine_diff_density_rms 0.273