# Electronic Supplementary Material (ESI) for Organic & Biomolecular 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_q98a _database_code_depnum_ccdc_archive 'CCDC 892953' #TrackingRef '12742_web_deposit_cif_file_0_QiqiangWang_1342798116.q98a_cmpd A.cif' _audit_creation_method SHELXTL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H14 Cl N O' _chemical_formula_weight 151.63 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' _cell_length_a 8.2735(3) _cell_length_b 9.7455(4) _cell_length_c 9.7543(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 786.48(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7971 _cell_measurement_theta_min 5.35 _cell_measurement_theta_max 68.92 _exptl_crystal_description 'Irregular chunk' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.281 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 328 _exptl_absorpt_coefficient_mu 3.695 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.817 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Bruker MicroStar microfocus rotating anode' _diffrn_radiation_monochromator 'Helios multilayer optics' _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 8137 _diffrn_reflns_av_R_equivalents 0.0223 _diffrn_reflns_av_sigmaI/netI 0.0137 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _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 6.42 _diffrn_reflns_theta_max 69.35 _reflns_number_total 1438 _reflns_number_gt 1438 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections except those that were flagged by the user for bring in the beamstop. 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^)+(0.0230P)^2^+0.1025P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0016(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(11) _refine_ls_number_reflns 1438 _refine_ls_number_parameters 140 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0154 _refine_ls_R_factor_gt 0.0154 _refine_ls_wR_factor_ref 0.0418 _refine_ls_wR_factor_gt 0.0418 _refine_ls_goodness_of_fit_ref 1.154 _refine_ls_restrained_S_all 1.154 _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 O O 0.52276(11) 0.61485(8) 0.33614(8) 0.02294(19) Uani 1 1 d . . . N N 0.45878(11) 0.42635(8) 0.56146(9) 0.0135(2) Uani 1 1 d . . . C1 C 0.54853(14) 0.47044(12) 0.31995(11) 0.0193(2) Uani 1 1 d . . . H1A H 0.6640(16) 0.4513(13) 0.3377(13) 0.014(3) Uiso 1 1 d . . . H1B H 0.5294(16) 0.4463(13) 0.2291(13) 0.019(3) Uiso 1 1 d . . . C2 C 0.43660(14) 0.38914(12) 0.41125(10) 0.0160(2) Uani 1 1 d . . . H2A H 0.3262(17) 0.4096(14) 0.3915(12) 0.015(3) Uiso 1 1 d . . . H2B H 0.4554(16) 0.2888(13) 0.4042(13) 0.017(3) Uiso 1 1 d . . . C3 C 0.44467(15) 0.58095(11) 0.57325(12) 0.0187(3) Uani 1 1 d . . . H3A H 0.3341(17) 0.6012(13) 0.5520(14) 0.017(3) Uiso 1 1 d . . . H3B H 0.4719(16) 0.6003(13) 0.6644(13) 0.019(3) Uiso 1 1 d . . . C4 C 0.55731(16) 0.65320(12) 0.47494(12) 0.0223(3) Uani 1 1 d . . . H4A H 0.6718(18) 0.6330(13) 0.4964(12) 0.017(3) Uiso 1 1 d . . . H4B H 0.5355(17) 0.7468(14) 0.4822(14) 0.023(3) Uiso 1 1 d . . . C5 C 0.61838(13) 0.37576(12) 0.61537(12) 0.0156(2) Uani 1 1 d . . . H5A H 0.7055(16) 0.4158(13) 0.5645(14) 0.016(3) Uiso 1 1 d . . . H5B H 0.6175(16) 0.2789(14) 0.6052(13) 0.018(3) Uiso 1 1 d . . . H5C H 0.6289(16) 0.4027(14) 0.7107(14) 0.016(3) Uiso 1 1 d . . . C6 C 0.32728(14) 0.36047(12) 0.64426(11) 0.0176(2) Uani 1 1 d . . . H6A H 0.3393(16) 0.2592(14) 0.6355(13) 0.016(3) Uiso 1 1 d . . . H6B H 0.3424(18) 0.3851(15) 0.7382(15) 0.024(4) Uiso 1 1 d . . . H6C H 0.2225(17) 0.3920(13) 0.6090(13) 0.017(3) Uiso 1 1 d . . . Cl Cl 0.49069(3) 0.01727(2) 0.55444(2) 0.01515(9) 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 O 0.0314(5) 0.0174(4) 0.0200(4) 0.0048(3) -0.0010(4) 0.0003(4) N 0.0142(5) 0.0128(4) 0.0136(4) -0.0011(3) -0.0012(4) 0.0003(3) C1 0.0227(6) 0.0194(6) 0.0159(5) -0.0002(4) 0.0001(4) 0.0019(4) C2 0.0172(5) 0.0175(5) 0.0133(5) -0.0028(4) -0.0016(4) -0.0002(4) C3 0.0235(6) 0.0117(5) 0.0210(6) -0.0027(4) -0.0012(5) 0.0031(4) C4 0.0284(7) 0.0144(5) 0.0241(6) 0.0001(4) -0.0016(5) -0.0003(4) C5 0.0133(5) 0.0168(5) 0.0167(5) -0.0007(4) -0.0004(4) 0.0007(4) C6 0.0148(5) 0.0218(6) 0.0163(6) -0.0004(4) 0.0005(4) -0.0011(5) Cl 0.01541(13) 0.01581(13) 0.01423(13) 0.00052(8) -0.00022(9) 0.00015(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 O C1 1.4321(14) . ? O C4 1.4334(14) . ? N C6 1.4993(14) . ? N C5 1.5044(14) . ? N C3 1.5155(12) . ? N C2 1.5205(12) . ? C1 C2 1.5094(16) . ? C1 H1A 0.988(13) . ? C1 H1B 0.930(13) . ? C2 H2A 0.954(14) . ? C2 H2B 0.992(13) . ? C3 C4 1.5112(18) . ? C3 H3A 0.959(14) . ? C3 H3B 0.936(13) . ? C4 H4A 0.990(15) . ? C4 H4B 0.932(14) . ? C5 H5A 0.958(14) . ? C5 H5B 0.949(14) . ? C5 H5C 0.970(14) . ? C6 H6A 0.995(13) . ? C6 H6B 0.956(14) . ? C6 H6C 0.982(14) . ? 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 O C4 109.31(8) . . ? C6 N C5 107.96(8) . . ? C6 N C3 109.20(9) . . ? C5 N C3 111.52(8) . . ? C6 N C2 109.23(8) . . ? C5 N C2 111.38(9) . . ? C3 N C2 107.51(8) . . ? O C1 C2 111.06(9) . . ? O C1 H1A 108.1(7) . . ? C2 C1 H1A 113.0(8) . . ? O C1 H1B 109.1(8) . . ? C2 C1 H1B 109.0(8) . . ? H1A C1 H1B 106.5(11) . . ? C1 C2 N 111.68(9) . . ? C1 C2 H2A 111.0(8) . . ? N C2 H2A 105.1(7) . . ? C1 C2 H2B 112.3(8) . . ? N C2 H2B 106.4(7) . . ? H2A C2 H2B 110.0(11) . . ? C4 C3 N 111.57(10) . . ? C4 C3 H3A 110.8(8) . . ? N C3 H3A 105.2(8) . . ? C4 C3 H3B 111.1(8) . . ? N C3 H3B 104.7(8) . . ? H3A C3 H3B 113.1(12) . . ? O C4 C3 110.79(10) . . ? O C4 H4A 109.8(7) . . ? C3 C4 H4A 111.3(7) . . ? O C4 H4B 106.8(9) . . ? C3 C4 H4B 106.8(9) . . ? H4A C4 H4B 111.3(12) . . ? N C5 H5A 110.2(8) . . ? N C5 H5B 106.4(8) . . ? H5A C5 H5B 110.9(11) . . ? N C5 H5C 109.0(8) . . ? H5A C5 H5C 108.6(11) . . ? H5B C5 H5C 111.7(11) . . ? N C6 H6A 107.8(8) . . ? N C6 H6B 108.3(9) . . ? H6A C6 H6B 108.6(11) . . ? N C6 H6C 108.5(8) . . ? H6A C6 H6C 111.6(11) . . ? H6B C6 H6C 111.8(12) . . ? 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 C4 O C1 C2 61.74(12) . . . . ? O C1 C2 N -58.33(12) . . . . ? C6 N C2 C1 170.77(9) . . . . ? C5 N C2 C1 -70.07(11) . . . . ? C3 N C2 C1 52.38(12) . . . . ? C6 N C3 C4 -171.18(9) . . . . ? C5 N C3 C4 69.59(12) . . . . ? C2 N C3 C4 -52.78(12) . . . . ? C1 O C4 C3 -62.06(12) . . . . ? N C3 C4 O 59.14(13) . . . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 69.35 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.161 _refine_diff_density_min -0.135 _refine_diff_density_rms 0.032 data_q27b _database_code_depnum_ccdc_archive 'CCDC 892954' #TrackingRef 'web_deposit_cif_file_1_QiqiangWang_1342798116.q27b_cmpd B.cif' _audit_creation_method SHELXTL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H28 Cl2 N2 O2' _chemical_formula_weight 279.24 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M Cc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 21.0466(7) _cell_length_b 5.8427(2) _cell_length_c 12.7574(4) _cell_angle_alpha 90.00 _cell_angle_beta 104.3700(10) _cell_angle_gamma 90.00 _cell_volume 1519.68(9) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4648 _cell_measurement_theta_min 4.34 _cell_measurement_theta_max 68.96 _exptl_crystal_description 'Thin plate' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.221 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 3.777 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.791 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Bruker MicroSTAR microfocus rotating anode' _diffrn_radiation_monochromator 'Helios multilayer x-ray optics' _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 4835 _diffrn_reflns_av_R_equivalents 0.0227 _diffrn_reflns_av_sigmaI/netI 0.0372 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 4.34 _diffrn_reflns_theta_max 69.06 _reflns_number_total 2177 _reflns_number_gt 2167 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections except those that were flagged by the user for being in the beamstop. 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^)+(0.0369P)^2^+0.0473P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _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 0.041(10) _refine_ls_number_reflns 2177 _refine_ls_number_parameters 257 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0240 _refine_ls_R_factor_gt 0.0239 _refine_ls_wR_factor_ref 0.0586 _refine_ls_wR_factor_gt 0.0585 _refine_ls_goodness_of_fit_ref 1.096 _refine_ls_restrained_S_all 1.095 _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 Cl1 Cl 0.375350(18) 0.56701(6) 0.38452(3) 0.02220(11) Uani 1 1 d . . . Cl2 Cl 0.62085(2) 0.27023(7) 0.61467(3) 0.02391(11) Uani 1 1 d . . . O O 0.31635(7) 0.0795(2) 0.60493(11) 0.0247(3) Uani 1 1 d . . . N1 N 0.20669(7) 0.3386(3) 0.43581(11) 0.0200(3) Uani 1 1 d . . . N2 N 0.45886(7) -0.0695(2) 0.65011(12) 0.0186(3) Uani 1 1 d . . . C1 C 0.24689(9) 0.4046(3) 0.54735(14) 0.0220(4) Uani 1 1 d . . . H1A H 0.2825(11) 0.473(4) 0.5343(17) 0.017(5) Uiso 1 1 d . . . H1B H 0.2229(11) 0.519(4) 0.5745(18) 0.021(5) Uiso 1 1 d . . . C2 C 0.26505(10) 0.2131(4) 0.62884(15) 0.0247(4) Uani 1 1 d . . . H2A H 0.2791(13) 0.284(4) 0.696(2) 0.029(6) Uiso 1 1 d . . . H2B H 0.2260(13) 0.109(5) 0.632(2) 0.034(7) Uiso 1 1 d . . . C3 C 0.34509(9) -0.0742(3) 0.68970(15) 0.0217(3) Uani 1 1 d . . . H3A H 0.3566(11) -0.011(4) 0.750(2) 0.023(5) Uiso 1 1 d . . . H3B H 0.3172(14) -0.178(5) 0.704(2) 0.034(6) Uiso 1 1 d . . . C4 C 0.39979(9) -0.2069(3) 0.66114(14) 0.0203(3) Uani 1 1 d . . . H4A H 0.4170(10) -0.313(4) 0.7156(18) 0.017(5) Uiso 1 1 d . . . H4B H 0.3831(12) -0.279(4) 0.596(2) 0.023(5) Uiso 1 1 d . . . C5 C 0.14177(9) 0.2405(3) 0.44021(16) 0.0259(4) Uani 1 1 d . . . H5A H 0.1225(12) 0.352(4) 0.4773(19) 0.026(5) Uiso 1 1 d . . . H5B H 0.1493(12) 0.112(4) 0.487(2) 0.026(5) Uiso 1 1 d . . . H5C H 0.1203(12) 0.205(4) 0.372(2) 0.023(5) Uiso 1 1 d . . . C6 C 0.19461(10) 0.5524(3) 0.36844(17) 0.0249(4) Uani 1 1 d . . . H6A H 0.1705(12) 0.514(5) 0.299(2) 0.024(6) Uiso 1 1 d . . . H6B H 0.2344(13) 0.622(4) 0.368(2) 0.030(6) Uiso 1 1 d . . . H6C H 0.1726(12) 0.659(5) 0.401(2) 0.025(5) Uiso 1 1 d . . . C7 C 0.24260(9) 0.1712(3) 0.38194(15) 0.0229(4) Uani 1 1 d . . . H7A H 0.2515(11) 0.041(4) 0.4238(18) 0.013(5) Uiso 1 1 d . . . H7B H 0.2188(13) 0.156(4) 0.310(2) 0.026(6) Uiso 1 1 d . . . H7C H 0.2825(14) 0.229(4) 0.381(2) 0.021(5) Uiso 1 1 d . . . C8 C 0.48465(9) 0.0806(3) 0.74658(16) 0.0242(4) Uani 1 1 d . . . H8B H 0.4933(11) -0.009(4) 0.803(2) 0.017(5) Uiso 1 1 d . . . H8C H 0.5224(13) 0.147(5) 0.736(2) 0.030(6) Uiso 1 1 d . . . H8A H 0.4497(13) 0.184(4) 0.749(2) 0.030(6) Uiso 1 1 d . . . C9 C 0.44371(9) 0.0752(3) 0.54940(16) 0.0251(4) Uani 1 1 d . . . H9A H 0.4239(14) -0.022(5) 0.490(2) 0.032(6) Uiso 1 1 d . . . H9B H 0.4155(14) 0.190(5) 0.554(2) 0.031(6) Uiso 1 1 d . . . H9C H 0.4863(12) 0.145(4) 0.5478(19) 0.029(6) Uiso 1 1 d . . . C10 C 0.51124(10) -0.2376(3) 0.64096(16) 0.0239(4) Uani 1 1 d . . . H10A H 0.4959(13) -0.332(5) 0.585(2) 0.031(6) Uiso 1 1 d . . . H10B H 0.5234(11) -0.330(4) 0.702(2) 0.022(5) Uiso 1 1 d . . . H10C H 0.5479(13) -0.161(5) 0.6303(19) 0.029(6) Uiso 1 1 d . . . O1W O 0.52158(8) 0.4259(3) 0.39091(13) 0.0306(3) Uani 1 1 d . . . H1W1 H 0.4807(14) 0.480(5) 0.398(2) 0.033(6) Uiso 1 1 d . . . H1W2 H 0.5419(16) 0.396(5) 0.448(3) 0.038(8) Uiso 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 Cl1 0.0220(2) 0.0249(2) 0.0189(2) 0.00033(13) 0.00350(14) -0.00292(13) Cl2 0.01927(19) 0.0270(2) 0.0252(2) 0.00551(16) 0.00488(14) 0.00102(14) O 0.0214(7) 0.0348(7) 0.0192(7) 0.0015(4) 0.0075(5) 0.0054(5) N1 0.0187(7) 0.0203(8) 0.0208(7) -0.0013(5) 0.0046(6) -0.0036(5) N2 0.0185(8) 0.0199(7) 0.0170(7) -0.0010(5) 0.0036(6) -0.0022(5) C1 0.0148(8) 0.0272(9) 0.0243(9) -0.0089(7) 0.0052(7) -0.0033(6) C2 0.0179(9) 0.0386(10) 0.0172(9) -0.0047(7) 0.0036(7) 0.0006(7) C3 0.0211(9) 0.0281(9) 0.0154(9) -0.0004(6) 0.0037(7) -0.0044(6) C4 0.0217(9) 0.0213(8) 0.0174(8) -0.0003(7) 0.0041(6) -0.0044(6) C5 0.0190(9) 0.0314(10) 0.0253(10) 0.0052(7) 0.0016(8) -0.0069(6) C6 0.0261(10) 0.0216(9) 0.0282(10) 0.0024(7) 0.0090(8) -0.0017(7) C7 0.0261(10) 0.0207(10) 0.0214(10) -0.0033(7) 0.0047(7) -0.0013(7) C8 0.0218(10) 0.0258(9) 0.0245(10) -0.0068(7) 0.0049(7) -0.0041(7) C9 0.0230(10) 0.0264(9) 0.0259(10) 0.0068(7) 0.0058(8) -0.0030(7) C10 0.0238(9) 0.0253(9) 0.0234(10) -0.0011(7) 0.0075(8) 0.0030(7) O1W 0.0242(8) 0.0465(9) 0.0205(8) 0.0006(5) 0.0043(6) -0.0052(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 O C3 1.420(2) . ? O C2 1.426(2) . ? N1 C5 1.495(2) . ? N1 C6 1.502(2) . ? N1 C7 1.502(2) . ? N1 C1 1.514(2) . ? N2 C8 1.499(2) . ? N2 C10 1.503(2) . ? N2 C9 1.504(2) . ? N2 C4 1.516(2) . ? C1 C2 1.510(3) . ? C1 H1A 0.90(2) . ? C1 H1B 0.95(2) . ? C2 H2A 0.93(3) . ? C2 H2B 1.03(3) . ? C3 C4 1.506(2) . ? C3 H3A 0.83(3) . ? C3 H3B 0.89(3) . ? C4 H4A 0.93(2) . ? C4 H4B 0.92(3) . ? C5 H5A 0.95(3) . ? C5 H5B 0.95(3) . ? C5 H5C 0.90(3) . ? C6 H6A 0.93(3) . ? C6 H6B 0.93(3) . ? C6 H6C 0.94(3) . ? C7 H7A 0.92(2) . ? C7 H7B 0.93(3) . ? C7 H7C 0.91(3) . ? C8 H8B 0.87(3) . ? C8 H8C 0.92(3) . ? C8 H8A 0.96(3) . ? C9 H9A 0.95(3) . ? C9 H9B 0.91(3) . ? C9 H9C 0.99(3) . ? C10 H10A 0.90(3) . ? C10 H10B 0.93(3) . ? C10 H10C 0.93(3) . ? O1W H1W1 0.94(3) . ? O1W H1W2 0.77(4) . ? 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 C3 O C2 112.67(14) . . ? C5 N1 C6 108.28(14) . . ? C5 N1 C7 109.63(14) . . ? C6 N1 C7 108.20(13) . . ? C5 N1 C1 111.41(14) . . ? C6 N1 C1 107.56(14) . . ? C7 N1 C1 111.62(13) . . ? C8 N2 C10 108.86(14) . . ? C8 N2 C9 109.23(13) . . ? C10 N2 C9 107.76(14) . . ? C8 N2 C4 111.83(14) . . ? C10 N2 C4 107.18(13) . . ? C9 N2 C4 111.84(13) . . ? C2 C1 N1 116.44(15) . . ? C2 C1 H1A 112.0(14) . . ? N1 C1 H1A 103.6(14) . . ? C2 C1 H1B 109.6(14) . . ? N1 C1 H1B 107.3(14) . . ? H1A C1 H1B 107(2) . . ? O C2 C1 109.52(15) . . ? O C2 H2A 110.8(17) . . ? C1 C2 H2A 105.7(16) . . ? O C2 H2B 109.8(15) . . ? C1 C2 H2B 113.5(15) . . ? H2A C2 H2B 107(2) . . ? O C3 C4 110.36(15) . . ? O C3 H3A 113.2(17) . . ? C4 C3 H3A 112.8(16) . . ? O C3 H3B 114.0(18) . . ? C4 C3 H3B 106.3(19) . . ? H3A C3 H3B 100(2) . . ? C3 C4 N2 116.34(14) . . ? C3 C4 H4A 109.9(13) . . ? N2 C4 H4A 104.2(13) . . ? C3 C4 H4B 108.1(15) . . ? N2 C4 H4B 107.4(16) . . ? H4A C4 H4B 110.9(19) . . ? N1 C5 H5A 105.2(15) . . ? N1 C5 H5B 108.4(15) . . ? H5A C5 H5B 105(2) . . ? N1 C5 H5C 107.2(15) . . ? H5A C5 H5C 118(2) . . ? H5B C5 H5C 113.1(19) . . ? N1 C6 H6A 108.7(16) . . ? N1 C6 H6B 110.0(16) . . ? H6A C6 H6B 112(2) . . ? N1 C6 H6C 109.4(15) . . ? H6A C6 H6C 112(2) . . ? H6B C6 H6C 105(2) . . ? N1 C7 H7A 109.0(13) . . ? N1 C7 H7B 107.6(15) . . ? H7A C7 H7B 118.2(19) . . ? N1 C7 H7C 109.6(14) . . ? H7A C7 H7C 105(2) . . ? H7B C7 H7C 107(2) . . ? N2 C8 H8B 106.7(15) . . ? N2 C8 H8C 105.9(16) . . ? H8B C8 H8C 111(2) . . ? N2 C8 H8A 105.7(16) . . ? H8B C8 H8A 111(2) . . ? H8C C8 H8A 116(2) . . ? N2 C9 H9A 107.4(17) . . ? N2 C9 H9B 111.5(16) . . ? H9A C9 H9B 109(2) . . ? N2 C9 H9C 104.3(14) . . ? H9A C9 H9C 117(2) . . ? H9B C9 H9C 108(2) . . ? N2 C10 H10A 109.8(17) . . ? N2 C10 H10B 111.6(14) . . ? H10A C10 H10B 106(2) . . ? N2 C10 H10C 110.4(16) . . ? H10A C10 H10C 109(2) . . ? H10B C10 H10C 109.7(19) . . ? H1W1 O1W H1W2 107(3) . . ? 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 C5 N1 C1 C2 61.74(19) . . . . ? C6 N1 C1 C2 -179.73(15) . . . . ? C7 N1 C1 C2 -61.19(19) . . . . ? C3 O C2 C1 168.05(14) . . . . ? N1 C1 C2 O 75.38(19) . . . . ? C2 O C3 C4 -178.78(14) . . . . ? O C3 C4 N2 64.95(19) . . . . ? C8 N2 C4 C3 51.12(19) . . . . ? C10 N2 C4 C3 170.34(15) . . . . ? C9 N2 C4 C3 -71.76(19) . . . . ? 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 O1W H1W1 Cl1 0.94(3) 2.24(3) 3.1675(17) 169(2) . O1W H1W2 Cl2 0.77(4) 2.46(4) 3.2220(17) 170(3) . _diffrn_measured_fraction_theta_max 0.933 _diffrn_reflns_theta_full 69.06 _diffrn_measured_fraction_theta_full 0.933 _refine_diff_density_max 0.272 _refine_diff_density_min -0.147 _refine_diff_density_rms 0.045