Supplementary Material (ESI) for Perkin Transactions This journal is © The Royal society of Chemistry 2001 data_my05sad _database_code_CSD 163023 _journal_coden_Cambridge 188 _publ_requested_journal 'Perkin Transactions 2' loop_ _publ_author_name 'Liao, Fen-Ling' 'Rashidi-Ranjbar, Parviz' 'Taghvaei-Ganjali, Saeed' 'Wang, Sue-Lein' _publ_contact_author_name 'Dr Parviz Rashidi-Ranjbar' _publ_contact_author_address ; Dr Parviz Rashidi-Ranjbar Department of Chemistry, Faculty of Science University of Tehran Tehran IRAN ; _publ_contact_author_email 'RANJBAR@KHAYAM.UT.AC.IR' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H16 Cl N O' _chemical_formula_weight 285.76 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/n 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 5.6162(4) _cell_length_b 13.3544(10) _cell_length_c 18.6704(14) _cell_angle_alpha 90.00 _cell_angle_beta 95.74 _cell_angle_gamma 90.00 _cell_volume 1393.27(18) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2686 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 25 _exptl_crystal_description Columnar _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.362 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 600 _exptl_absorpt_coefficient_mu 0.269 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6688 _exptl_absorpt_correction_T_max 0.9562 _exptl_absorpt_process_details ? _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7837 _diffrn_reflns_av_R_equivalents 0.0601 _diffrn_reflns_av_sigmaI/netI 0.0890 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 28.03 _reflns_number_total 3029 _reflns_number_gt 1733 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0417P)^2^+1.0009P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3029 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1344 _refine_ls_R_factor_gt 0.0663 _refine_ls_wR_factor_ref 0.1480 _refine_ls_wR_factor_gt 0.1206 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _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 0.10758(17) 0.81250(7) 0.03433(5) 0.0517(3) Uani 1 1 d . . . O1 O -0.6804(4) 0.56982(16) 0.03682(12) 0.0424(6) Uani 1 1 d . . . N1 N -0.2024(5) 0.62809(19) 0.01317(13) 0.0367(7) Uani 1 1 d . . . C1 C -0.1562(5) 0.8088(2) -0.02385(16) 0.0344(7) Uani 1 1 d . . . C2 C -0.2415(6) 0.8927(2) -0.05465(17) 0.0367(8) Uani 1 1 d . . . C3 C -0.4548(6) 0.8964(2) -0.10632(16) 0.0358(8) Uani 1 1 d . . . C4 C -0.5981(7) 0.9820(2) -0.10487(18) 0.0433(9) Uani 1 1 d . . . C5 C -0.8087(7) 0.9916(3) -0.1497(2) 0.0520(10) Uani 1 1 d . . . C6 C -0.8806(6) 0.9146(3) -0.1977(2) 0.0514(10) Uani 1 1 d . . . C7 C -0.7359(6) 0.8315(3) -0.20194(18) 0.0458(9) Uani 1 1 d . . . C8 C -0.5194(6) 0.8203(2) -0.15760(16) 0.0356(8) Uani 1 1 d . . . C9 C -0.3599(6) 0.7359(2) -0.17124(17) 0.0361(8) Uani 1 1 d . . . C10 C -0.3294(6) 0.7101(3) -0.24306(17) 0.0449(9) Uani 1 1 d . . . C11 C -0.1734(7) 0.6345(3) -0.25862(19) 0.0506(10) Uani 1 1 d . . . C12 C -0.0446(7) 0.5831(3) -0.2042(2) 0.0503(10) Uani 1 1 d . . . C13 C -0.0720(6) 0.6061(2) -0.13241(18) 0.0411(8) Uani 1 1 d . . . C14 C -0.2301(6) 0.6807(2) -0.11598(16) 0.0330(7) Uani 1 1 d . . . C15 C -0.2733(6) 0.7063(2) -0.03896(16) 0.0335(7) Uani 1 1 d . . . C16 C -0.3026(6) 0.6445(3) 0.08249(17) 0.0421(9) Uani 1 1 d . . . C17 C -0.4974(6) 0.5694(3) 0.09512(18) 0.0445(9) Uani 1 1 d . . . H1 H -0.7209 0.5006 0.0270 0.080 Uiso 1 1 d . . . H1A H -0.0293 0.6312 0.0142 0.080 Uiso 1 1 d . . . H2A H -0.1240 0.9606 -0.0411 0.080 Uiso 1 1 d . . . H4A H -0.5446 1.0466 -0.0639 0.080 Uiso 1 1 d . . . H5A H -0.9196 1.0527 -0.1393 0.080 Uiso 1 1 d . . . H6A H -1.0513 0.9232 -0.2244 0.080 Uiso 1 1 d . . . H7A H -0.8026 0.7730 -0.2397 0.080 Uiso 1 1 d . . . H10A H -0.4465 0.7531 -0.2858 0.080 Uiso 1 1 d . . . H11A H -0.1537 0.6230 -0.3136 0.080 Uiso 1 1 d . . . H12A H 0.0759 0.5261 -0.2175 0.080 Uiso 1 1 d . . . H13A H 0.0395 0.5581 -0.0943 0.080 Uiso 1 1 d . . . H15A H -0.4582 0.7192 -0.0365 0.080 Uiso 1 1 d . . . H16A H -0.3448 0.7164 0.0953 0.080 Uiso 1 1 d . . . H16B H -0.1660 0.6401 0.1261 0.080 Uiso 1 1 d . . . H17A H -0.5694 0.5928 0.1421 0.080 Uiso 1 1 d . . . H17B H -0.3935 0.5003 0.1002 0.080 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 0.0478(5) 0.0436(5) 0.0609(6) -0.0054(5) -0.0080(4) -0.0050(4) O1 0.0365(13) 0.0375(13) 0.0518(14) 0.0025(11) -0.0022(11) -0.0004(11) N1 0.0396(16) 0.0330(15) 0.0383(15) 0.0000(13) 0.0074(13) -0.0020(13) C1 0.0354(18) 0.0343(18) 0.0337(17) -0.0040(15) 0.0038(14) -0.0022(16) C2 0.041(2) 0.0344(18) 0.0356(18) -0.0027(15) 0.0094(15) -0.0052(15) C3 0.042(2) 0.0314(18) 0.0353(18) 0.0063(15) 0.0125(15) -0.0008(15) C4 0.052(2) 0.038(2) 0.042(2) 0.0100(16) 0.0173(17) 0.0079(18) C5 0.056(3) 0.053(2) 0.050(2) 0.015(2) 0.021(2) 0.016(2) C6 0.039(2) 0.066(3) 0.051(2) 0.016(2) 0.0089(18) 0.0093(19) C7 0.041(2) 0.056(2) 0.041(2) 0.0071(18) 0.0035(16) -0.0012(18) C8 0.0388(19) 0.0359(18) 0.0327(17) 0.0037(15) 0.0058(14) -0.0037(16) C9 0.0377(19) 0.0341(18) 0.0365(19) -0.0048(15) 0.0034(15) -0.0052(15) C10 0.049(2) 0.048(2) 0.037(2) -0.0050(17) 0.0017(16) -0.0023(18) C11 0.060(3) 0.053(2) 0.039(2) -0.0135(18) 0.0085(18) -0.001(2) C12 0.052(2) 0.046(2) 0.054(2) -0.0088(19) 0.0145(19) 0.0039(19) C13 0.047(2) 0.0317(18) 0.045(2) -0.0032(16) 0.0100(17) 0.0004(16) C14 0.0374(18) 0.0269(16) 0.0352(18) -0.0039(14) 0.0056(14) -0.0054(15) C15 0.0388(18) 0.0294(17) 0.0318(17) -0.0024(14) 0.0011(14) 0.0024(14) C16 0.048(2) 0.046(2) 0.0327(18) -0.0076(16) 0.0063(16) -0.0088(17) C17 0.044(2) 0.055(2) 0.0340(19) 0.0024(17) 0.0021(16) -0.0054(18) _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 C1 1.748(3) . ? O1 C17 1.421(4) . ? N1 C15 1.456(4) . ? N1 C16 1.478(4) . ? C1 C2 1.327(4) . ? C1 C15 1.532(4) . ? C2 C3 1.462(5) . ? C3 C4 1.401(4) . ? C3 C8 1.418(4) . ? C4 C5 1.385(5) . ? C5 C6 1.397(5) . ? C6 C7 1.383(5) . ? C7 C8 1.409(4) . ? C8 C9 1.477(4) . ? C9 C14 1.410(4) . ? C9 C10 1.412(4) . ? C10 C11 1.386(5) . ? C11 C12 1.372(5) . ? C12 C13 1.398(5) . ? C13 C14 1.389(4) . ? C14 C15 1.521(4) . ? C16 C17 1.520(5) . ? 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 C15 N1 C16 112.1(2) . . ? C2 C1 C15 123.0(3) . . ? C2 C1 Cl1 119.5(3) . . ? C15 C1 Cl1 117.5(2) . . ? C1 C2 C3 123.4(3) . . ? C4 C3 C8 119.3(3) . . ? C4 C3 C2 116.7(3) . . ? C8 C3 C2 124.0(3) . . ? C5 C4 C3 121.4(3) . . ? C4 C5 C6 119.6(3) . . ? C7 C6 C5 119.6(3) . . ? C6 C7 C8 122.0(3) . . ? C7 C8 C3 117.9(3) . . ? C7 C8 C9 118.8(3) . . ? C3 C8 C9 123.0(3) . . ? C14 C9 C10 117.6(3) . . ? C14 C9 C8 123.4(3) . . ? C10 C9 C8 118.9(3) . . ? C11 C10 C9 121.1(3) . . ? C12 C11 C10 120.5(3) . . ? C11 C12 C13 119.9(3) . . ? C14 C13 C12 120.3(3) . . ? C13 C14 C9 120.6(3) . . ? C13 C14 C15 122.4(3) . . ? C9 C14 C15 117.0(3) . . ? N1 C15 C14 114.3(2) . . ? N1 C15 C1 115.7(3) . . ? C14 C15 C1 105.6(2) . . ? N1 C16 C17 112.4(3) . . ? O1 C17 C16 110.8(3) . . ? _diffrn_measured_fraction_theta_max 0.896 _diffrn_reflns_theta_full 28.03 _diffrn_measured_fraction_theta_full 0.896 _refine_diff_density_max 0.245 _refine_diff_density_min -0.258 _refine_diff_density_rms 0.056