Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2007 ####################################################################### # # 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__nishii12 _database_code_depnum_ccdc_archive 'CCDC 646350' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C14 H17 Cl2 N O ' _chemical_formula_moiety 'C14 H17 Cl2 N O ' _chemical_formula_weight 286.20 _chemical_melting_point 381-382K _chemical_absolute_configuration rmad #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21 1' _symmetry_space_group_name_Hall 'P 2yb' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,1/2+Y,-Z #------------------------------------------------------------------------------ _cell_length_a 9.82(3) _cell_length_b 9.82(3) _cell_length_c 16.09(3) _cell_angle_alpha 90.0000 _cell_angle_beta 101.08(16) _cell_angle_gamma 90.0000 _cell_volume 1522(7) _cell_formula_units_Z 4 _cell_measurement_reflns_used 20 _cell_measurement_theta_min 10.1 _cell_measurement_theta_max 12.0 _cell_measurement_temperature 296.1 #------------------------------------------------------------------------------ _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.68 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.06 _exptl_crystal_density_diffrn 1.249 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 600.00 _exptl_absorpt_coefficient_mu 0.415 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North, Phillips & Mathews, 1968)' _exptl_absorpt_correction_T_min 0.864 _exptl_absorpt_correction_T_max 0.975 #============================================================================== # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71069 _diffrn_measurement_device_type 'Rigaku AFC5S' _diffrn_measurement_method \w-2\q _diffrn_reflns_number 3825 _diffrn_reflns_av_R_equivalents 0.062 _diffrn_reflns_theta_max 27.48 _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.977 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% 0.00 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 3608 _reflns_number_gt 1277 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0601 _refine_ls_wR_factor_ref 0.2149 _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 3608 _refine_ls_number_parameters 332 _refine_ls_goodness_of_fit_ref 0.955 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0923P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_shift/su_max 0.0000 _refine_diff_density_max 0.27 _refine_diff_density_min -0.24 _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 -0.09(16) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; N N 0.006 0.003 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.011 0.006 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; Cl Cl 0.148 0.159 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 Cl(1) Cl 0.3552(4) 0.5094(3) 0.3244(2) 0.1235(14) Uani 1.00 1 d . . . Cl(2) Cl 0.5963(3) 0.6355(3) 0.42184(18) 0.0883(9) Uani 1.00 1 d . . . Cl(3) Cl 0.3762(3) 0.3065(3) -0.0027(2) 0.1029(11) Uani 1.00 1 d . . . Cl(4) Cl 0.6443(3) 0.4225(3) 0.05779(19) 0.0924(9) Uani 1.00 1 d . . . O(1) O 0.6479(7) 0.9189(7) 0.2730(4) 0.083(2) Uani 1.00 1 d . . . O(2) O 0.6396(7) 0.4249(6) 0.2450(3) 0.0707(19) Uani 1.00 1 d . . . N(1) N 0.7177(8) 0.7087(7) 0.2511(4) 0.058(2) Uani 1.00 1 d . . . H(1N) H 0.6939 0.6249 0.2418 0.070 Uiso 1.00 1 c R . . N(2) N 0.6612(7) 0.2148(7) 0.2973(4) 0.057(2) Uani 1.00 1 d . . . H(2N) H 0.6425 0.1299 0.2882 0.069 Uiso 1.00 1 c R . . C(1) C 0.4624(10) 0.6560(11) 0.3381(6) 0.069(2) Uani 1.00 1 d . . . C(2) C 0.3943(10) 0.7931(11) 0.3215(7) 0.073(3) Uani 1.00 1 d . . . H(1) H 0.2945 0.7876 0.2988 0.087 Uiso 1.00 1 c R . . C(3) C 0.4829(9) 0.7369(10) 0.2614(6) 0.062(2) Uani 1.00 1 d . . . C(4) C 0.4330(13) 0.9078(11) 0.3822(8) 0.101(4) Uani 1.00 1 d . . . H(2) H 0.3751 0.9061 0.4239 0.121 Uiso 1.00 1 c R . . H(3) H 0.4205 0.9927 0.3520 0.121 Uiso 1.00 1 c R . . H(4) H 0.5284 0.8986 0.4096 0.121 Uiso 1.00 1 c R . . C(5) C 0.4134(11) 0.6940(14) 0.1747(7) 0.095(3) Uani 1.00 1 d . . . H(5) H 0.4695 0.6272 0.1535 0.113 Uiso 1.00 1 c R . . H(6) H 0.4015 0.7718 0.1378 0.113 Uiso 1.00 1 c R . . H(7) H 0.3243 0.6554 0.1769 0.113 Uiso 1.00 1 c R . . C(6) C 0.6246(10) 0.7976(10) 0.2627(5) 0.056(2) Uani 1.00 1 d . . . C(7) C 0.8645(8) 0.7495(9) 0.2537(6) 0.060(2) Uani 1.00 1 d . . . H(8) H 0.8640 0.8447 0.2353 0.072 Uiso 1.00 1 c R . . C(8) C 0.9432(11) 0.7434(14) 0.3423(7) 0.100(4) Uani 1.00 1 d . . . H(9) H 0.9322 0.8277 0.3705 0.120 Uiso 1.00 1 c R . . H(10) H 1.0397 0.7286 0.3421 0.120 Uiso 1.00 1 c R . . H(11) H 0.9084 0.6699 0.3717 0.120 Uiso 1.00 1 c R . . C(9) C 0.9295(9) 0.6660(10) 0.1929(6) 0.062(2) Uani 1.00 1 d . . . C(10) C 0.9601(11) 0.5320(12) 0.2053(7) 0.087(3) Uani 1.00 1 d . . . H(12) H 0.9409 0.4869 0.2525 0.105 Uiso 1.00 1 c R . . C(11) C 1.0218(13) 0.4617(15) 0.1449(12) 0.130(6) Uani 1.00 1 d . . . H(13) H 1.0442 0.3700 0.1531 0.156 Uiso 1.00 1 c R . . C(12) C 1.0487(19) 0.526(3) 0.0754(11) 0.158(9) Uani 1.00 1 d . . . H(14) H 1.0875 0.4784 0.0358 0.189 Uiso 1.00 1 c R . . C(13) C 1.019(2) 0.661(3) 0.0634(11) 0.158(8) Uani 1.00 1 d . . . H(15) H 1.0402 0.7081 0.0172 0.189 Uiso 1.00 1 c R . . C(14) C 0.9582(13) 0.7243(16) 0.1202(8) 0.110(4) Uani 1.00 1 d . . . H(16) H 0.9332 0.8150 0.1100 0.132 Uiso 1.00 1 c R . . C(15) C 0.5269(10) 0.2932(11) 0.0745(6) 0.070(2) Uani 1.00 1 d . . . C(16) C 0.5831(10) 0.1554(11) 0.0978(6) 0.072(2) Uani 1.00 1 d . . . H(17) H 0.5231 0.0804 0.0727 0.087 Uiso 1.00 1 c R . . C(17) C 0.5228(9) 0.2432(9) 0.1614(6) 0.059(2) Uani 1.00 1 d . . . C(18) C 0.7366(10) 0.1250(13) 0.1115(6) 0.088(3) Uani 1.00 1 d . . . H(18) H 0.7599 0.0942 0.0593 0.105 Uiso 1.00 1 c R . . H(19) H 0.7594 0.0554 0.1538 0.105 Uiso 1.00 1 c R . . H(20) H 0.7882 0.2062 0.1300 0.105 Uiso 1.00 1 c R . . C(19) C 0.3800(10) 0.1985(11) 0.1773(7) 0.078(3) Uani 1.00 1 d . . . H(21) H 0.3280 0.2773 0.1880 0.094 Uiso 1.00 1 c R . . H(22) H 0.3920 0.1390 0.2255 0.094 Uiso 1.00 1 c R . . H(23) H 0.3307 0.1513 0.1284 0.094 Uiso 1.00 1 c R . . C(20) C 0.6140(8) 0.3041(10) 0.2371(5) 0.048(2) Uani 1.00 1 d . . . C(21) C 0.7438(11) 0.2555(9) 0.3783(6) 0.074(3) Uani 1.00 1 d . . . H(24) H 0.7226 0.3509 0.3883 0.088 Uiso 1.00 1 c R . . C(22) C 0.7074(11) 0.1707(14) 0.4495(7) 0.098(4) Uani 1.00 1 d . . . H(25) H 0.6111 0.1832 0.4516 0.118 Uiso 1.00 1 c R . . H(26) H 0.7634 0.1988 0.5024 0.118 Uiso 1.00 1 c R . . H(27) H 0.7245 0.0763 0.4399 0.118 Uiso 1.00 1 c R . . C(23) C 0.8999(10) 0.2443(10) 0.3786(6) 0.061(2) Uani 1.00 1 d . . . C(24) C 0.9534(11) 0.1413(13) 0.3363(8) 0.092(3) Uani 1.00 1 d . . . H(28) H 0.8939 0.0786 0.3045 0.110 Uiso 1.00 1 c R . . C(25) C 1.0930(14) 0.1308(15) 0.3408(9) 0.119(4) Uani 1.00 1 d . . . H(29) H 1.1290 0.0593 0.3137 0.143 Uiso 1.00 1 c R . . C(26) C 1.1781(13) 0.2233(17) 0.3841(9) 0.107(4) Uani 1.00 1 d . . . H(30) H 1.2725 0.2182 0.3837 0.128 Uiso 1.00 1 c R . . C(27) C 1.1322(14) 0.3220(16) 0.4275(8) 0.108(4) Uani 1.00 1 d . . . H(31) H 1.1953 0.3817 0.4591 0.130 Uiso 1.00 1 c R . . C(28) C 0.9925(13) 0.3376(11) 0.4267(6) 0.083(3) Uani 1.00 1 d . . . H(32) H 0.9602 0.4074 0.4568 0.100 Uiso 1.00 1 c 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Cl(1) 0.123(2) 0.088(2) 0.183(3) -0.056(2) 0.086(2) -0.040(2) Cl(2) 0.116(2) 0.0768(19) 0.0785(18) 0.0110(19) 0.0345(17) 0.0085(16) Cl(3) 0.101(2) 0.100(2) 0.091(2) 0.011(2) -0.0237(16) 0.0031(19) Cl(4) 0.107(2) 0.0795(19) 0.0885(19) -0.0142(19) 0.0127(16) 0.0213(18) O(1) 0.094(5) 0.027(3) 0.138(6) 0.000(4) 0.047(4) 0.005(4) O(2) 0.103(5) 0.029(3) 0.078(4) -0.009(3) 0.012(3) -0.008(3) N(1) 0.075(5) 0.030(4) 0.072(5) -0.000(4) 0.023(4) -0.001(3) N(2) 0.075(5) 0.030(3) 0.060(4) 0.007(4) -0.005(4) -0.007(3) C(1) 0.071(6) 0.059(6) 0.085(7) -0.015(6) 0.035(5) -0.020(6) C(2) 0.057(6) 0.062(6) 0.106(8) 0.005(5) 0.032(5) -0.004(6) C(3) 0.058(6) 0.057(6) 0.074(6) 0.007(5) 0.021(5) -0.001(5) C(4) 0.124(9) 0.052(6) 0.150(11) 0.003(7) 0.088(8) -0.015(8) C(5) 0.065(7) 0.126(11) 0.091(8) -0.012(7) 0.014(6) 0.001(8) C(6) 0.064(6) 0.037(5) 0.071(6) -0.002(5) 0.026(4) -0.004(5) C(7) 0.053(5) 0.052(5) 0.083(7) -0.010(5) 0.032(5) -0.003(5) C(8) 0.078(7) 0.139(12) 0.088(9) -0.017(8) 0.030(7) -0.034(8) C(9) 0.042(5) 0.064(6) 0.079(6) 0.005(5) 0.011(4) 0.016(5) C(10) 0.080(7) 0.076(8) 0.111(9) 0.016(6) 0.030(6) 0.007(7) C(11) 0.082(9) 0.099(12) 0.213(18) -0.007(8) 0.038(11) -0.067(12) C(12) 0.102(12) 0.29(3) 0.082(11) -0.041(19) 0.026(9) -0.031(17) C(13) 0.154(16) 0.23(2) 0.105(12) 0.060(17) 0.070(11) 0.036(16) C(14) 0.107(9) 0.134(11) 0.096(8) 0.046(9) 0.035(8) 0.032(9) C(15) 0.069(6) 0.060(6) 0.080(7) 0.003(6) 0.011(5) -0.002(5) C(16) 0.077(7) 0.059(6) 0.081(7) -0.004(6) 0.013(5) -0.016(6) C(17) 0.063(6) 0.042(5) 0.073(6) 0.006(5) 0.017(5) -0.004(5) C(18) 0.094(8) 0.085(8) 0.090(7) 0.025(7) 0.030(6) -0.004(6) C(19) 0.059(6) 0.072(7) 0.101(8) -0.002(5) 0.007(5) -0.020(6) C(20) 0.048(5) 0.034(5) 0.060(5) 0.001(4) 0.003(4) -0.008(5) C(21) 0.120(9) 0.038(5) 0.061(6) 0.006(6) 0.015(6) -0.012(4) C(22) 0.083(7) 0.121(11) 0.093(7) -0.009(8) 0.025(6) 0.004(8) C(23) 0.066(6) 0.046(5) 0.068(6) 0.004(5) 0.004(5) 0.009(5) C(24) 0.061(7) 0.072(7) 0.134(10) -0.005(7) -0.005(7) -0.019(8) C(25) 0.082(9) 0.096(10) 0.167(13) -0.000(9) -0.004(9) -0.046(10) C(26) 0.085(9) 0.115(11) 0.118(11) -0.001(10) 0.015(8) 0.003(10) C(27) 0.084(10) 0.108(12) 0.125(11) -0.048(9) 0.001(8) -0.019(9) C(28) 0.105(9) 0.072(8) 0.069(6) -0.042(7) 0.005(6) -0.001(5) #============================================================================== _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'CrystalStructure (Rigaku & RAC 2007)' _computing_structure_solution 'SIR97 (Altomare, 1999)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_publication_material 'CrystalStructure (Rigaku & RAC 2007)' _computing_molecular_graphics 'ORTEP (Johnson, 1976)' #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 Cl(1) C(1) 1.771(11) yes . . Cl(2) C(1) 1.704(9) yes . . Cl(3) C(15) 1.744(9) yes . . Cl(4) C(15) 1.770(11) yes . . O(1) C(6) 1.217(12) yes . . O(2) C(20) 1.214(11) yes . . N(1) C(6) 1.304(12) yes . . N(1) C(7) 1.489(11) yes . . N(2) C(20) 1.322(11) yes . . N(2) C(21) 1.452(11) yes . . C(1) C(2) 1.504(15) yes . . C(1) C(3) 1.513(14) yes . . C(2) C(3) 1.523(15) yes . . C(2) C(4) 1.491(16) yes . . C(3) C(5) 1.492(14) yes . . C(3) C(6) 1.510(13) yes . . C(7) C(8) 1.486(13) yes . . C(7) C(9) 1.510(14) yes . . C(9) C(10) 1.355(16) yes . . C(9) C(14) 1.378(18) yes . . C(10) C(11) 1.42(2) yes . . C(11) C(12) 1.35(3) yes . . C(12) C(13) 1.36(4) yes . . C(13) C(14) 1.34(2) yes . . C(15) C(16) 1.482(15) yes . . C(15) C(17) 1.490(14) yes . . C(16) C(17) 1.540(15) yes . . C(16) C(18) 1.511(15) yes . . C(17) C(19) 1.537(14) yes . . C(17) C(20) 1.491(12) yes . . C(21) C(22) 1.515(16) yes . . C(21) C(23) 1.536(15) yes . . C(23) C(24) 1.378(16) yes . . C(23) C(28) 1.412(14) yes . . C(24) C(25) 1.363(18) yes . . C(25) C(26) 1.34(2) yes . . C(26) C(27) 1.32(2) yes . . C(27) C(28) 1.378(19) yes . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C(6) N(1) C(7) 121.2(7) yes . . . C(20) N(2) C(21) 122.1(7) yes . . . Cl(1) C(1) Cl(2) 110.6(5) yes . . . Cl(1) C(1) C(2) 118.1(7) yes . . . Cl(1) C(1) C(3) 119.6(6) yes . . . Cl(2) C(1) C(2) 119.7(7) yes . . . Cl(2) C(1) C(3) 120.2(7) yes . . . C(2) C(1) C(3) 60.6(7) yes . . . C(1) C(2) C(3) 60.0(7) yes . . . C(1) C(2) C(4) 120.7(8) yes . . . C(3) C(2) C(4) 125.7(9) yes . . . C(1) C(3) C(2) 59.4(7) yes . . . C(1) C(3) C(5) 120.4(9) yes . . . C(1) C(3) C(6) 117.6(7) yes . . . C(2) C(3) C(5) 118.8(8) yes . . . C(2) C(3) C(6) 119.1(8) yes . . . C(5) C(3) C(6) 112.3(8) yes . . . O(1) C(6) N(1) 123.8(9) yes . . . O(1) C(6) C(3) 122.5(9) yes . . . N(1) C(6) C(3) 113.8(8) yes . . . N(1) C(7) C(8) 109.8(8) yes . . . N(1) C(7) C(9) 111.3(7) yes . . . C(8) C(7) C(9) 113.2(8) yes . . . C(7) C(9) C(10) 122.7(10) yes . . . C(7) C(9) C(14) 120.4(10) yes . . . C(10) C(9) C(14) 116.9(11) yes . . . C(9) C(10) C(11) 118.9(12) yes . . . C(10) C(11) C(12) 120.9(17) yes . . . C(11) C(12) C(13) 120(2) yes . . . C(12) C(13) C(14) 118(2) yes . . . C(9) C(14) C(13) 125.5(17) yes . . . Cl(3) C(15) Cl(4) 109.1(5) yes . . . Cl(3) C(15) C(16) 118.2(7) yes . . . Cl(3) C(15) C(17) 121.4(7) yes . . . Cl(4) C(15) C(16) 118.1(7) yes . . . Cl(4) C(15) C(17) 121.0(6) yes . . . C(16) C(15) C(17) 62.4(6) yes . . . C(15) C(16) C(17) 59.0(6) yes . . . C(15) C(16) C(18) 122.0(9) yes . . . C(17) C(16) C(18) 120.9(8) yes . . . C(15) C(17) C(16) 58.5(6) yes . . . C(15) C(17) C(19) 116.1(7) yes . . . C(15) C(17) C(20) 120.9(8) yes . . . C(16) C(17) C(19) 115.5(8) yes . . . C(16) C(17) C(20) 121.3(8) yes . . . C(19) C(17) C(20) 113.7(8) yes . . . O(2) C(20) N(2) 122.3(7) yes . . . O(2) C(20) C(17) 123.9(7) yes . . . N(2) C(20) C(17) 113.8(8) yes . . . N(2) C(21) C(22) 110.8(8) yes . . . N(2) C(21) C(23) 111.6(8) yes . . . C(22) C(21) C(23) 109.8(8) yes . . . C(21) C(23) C(24) 121.7(8) yes . . . C(21) C(23) C(28) 119.5(9) yes . . . C(24) C(23) C(28) 118.7(10) yes . . . C(23) C(24) C(25) 120.3(11) yes . . . C(24) C(25) C(26) 119.9(14) yes . . . C(25) C(26) C(27) 122.1(13) yes . . . C(26) C(27) C(28) 121.0(12) yes . . . C(23) C(28) C(27) 118.0(11) yes . . . loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _geom_hbond_site_symmetry_A _geom_hbond_distance_DA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_angle_DHA _geom_hbond_publ_flag N(1) H(1N) O(2) . . . 2.885(9) 0.860 2.037 168.6 no N(2) H(2N) O(1) . . 1_545 2.931(10) 0.860 2.088 166.4 no #==END========================================================================= _chemical_name_common ; 'N-((1S, 3S)-2,2-dichloro-1,3-dimethylcyclopropanecarbonyl)- (1S)-1-phenylethylam ;