# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'RSC Advances' _journal_coden_cambridge 1500 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Manojit Pal' _publ_contact_author_email manojitpal@rediffmail.com _publ_author_name 'Manojit Pal' # Attachment '- CCTD_1_019_A.cif' data_cctd_1_019_a _database_code_depnum_ccdc_archive 'CCDC 867480' #TrackingRef '- CCTD_1_019_A.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H17 Cl2 N O' _chemical_formula_weight 357.07 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)/c ' 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 12.536(2) _cell_length_b 7.7673(11) _cell_length_c 18.601(3) _cell_angle_alpha 90.00 _cell_angle_beta 104.154(4) _cell_angle_gamma 90.00 _cell_volume 1756.2(5) _cell_formula_units_Z 4 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 6399 _cell_measurement_theta_min 2.58 _cell_measurement_theta_max 28.25 _exptl_crystal_description plate _exptl_crystal_colour translucent _exptl_crystal_size_max 0.01 _exptl_crystal_size_mid 0.006 _exptl_crystal_size_min 0.004 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.355 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 0.376 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.998 _exptl_absorpt_correction_T_max 0.999 _exptl_absorpt_process_details 'Multiscan absorption correction' _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 18148 _diffrn_reflns_av_R_equivalents 0.0643 _diffrn_reflns_av_sigmaI/netI 0.0622 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 28.28 _reflns_number_total 4357 _reflns_number_gt 2443 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0472P)^2^+0.5829P] 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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0030(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4357 _refine_ls_number_parameters 220 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1043 _refine_ls_R_factor_gt 0.0474 _refine_ls_wR_factor_ref 0.1360 _refine_ls_wR_factor_gt 0.1094 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.015 _refine_ls_shift/su_max 0.009 _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 C15 C 0.36759(18) 0.1967(3) 0.11518(13) 0.0415(6) Uani 1 1 d . . . C20 C 0.44692(18) 0.0830(3) 0.15436(13) 0.0421(6) Uani 1 1 d . . . C19 C 0.44690(19) 0.0228(3) 0.22446(13) 0.0467(6) Uani 1 1 d . . . H19 H 0.5009 -0.0529 0.2493 0.056 Uiso 1 1 calc R . . C18 C 0.3645(2) 0.0785(3) 0.25646(14) 0.0469(6) Uani 1 1 d . . . C17 C 0.2854(2) 0.1928(3) 0.22032(14) 0.0513(6) Uani 1 1 d . . . H17 H 0.2309 0.2305 0.2427 0.062 Uiso 1 1 calc R . . C16 C 0.2877(2) 0.2508(3) 0.15051(14) 0.0490(6) Uani 1 1 d . . . H16 H 0.2342 0.3284 0.1264 0.059 Uiso 1 1 calc R . . C14 C 0.3703(2) 0.2529(3) 0.03777(14) 0.0527(7) Uani 1 1 d . . . H14A H 0.4380 0.3159 0.0405 0.063 Uiso 1 1 calc R . . H14B H 0.3719 0.1510 0.0079 0.063 Uiso 1 1 calc R . . C10 C 0.1855(2) 0.2961(3) -0.04843(13) 0.0462(6) Uani 1 1 d . . . H10 H 0.1714 0.1803 -0.0595 0.055 Uiso 1 1 calc R . . C7 C 0.11816(19) 0.4290(3) -0.07773(12) 0.0392(5) Uani 1 1 d . . . C8 C 0.17307(19) 0.5833(3) -0.04531(13) 0.0400(5) Uani 1 1 d . . . C9 C 0.2718(2) 0.5350(3) 0.00230(13) 0.0435(6) Uani 1 1 d . . . C1 C 0.01561(19) 0.4096(3) -0.13721(13) 0.0420(6) Uani 1 1 d . . . C2 C -0.0676(2) 0.3003(4) -0.12832(16) 0.0574(7) Uani 1 1 d . . . H2 H -0.0600 0.2405 -0.0840 0.069 Uiso 1 1 calc R . . C3 C -0.1621(2) 0.2792(4) -0.1848(2) 0.0759(10) Uani 1 1 d . . . H3 H -0.2168 0.2040 -0.1784 0.091 Uiso 1 1 calc R . . C12 C 0.1335(2) 0.7611(3) -0.05360(14) 0.0520(6) Uani 1 1 d . . . C4 C -0.1752(3) 0.3688(5) -0.2499(2) 0.0823(11) Uani 1 1 d . . . H4 H -0.2394 0.3565 -0.2871 0.099 Uiso 1 1 calc R . . C5 C -0.0933(3) 0.4766(4) -0.25991(16) 0.0724(9) Uani 1 1 d . . . H5 H -0.1018 0.5367 -0.3042 0.087 Uiso 1 1 calc R . . C6 C 0.0017(2) 0.4960(3) -0.20411(14) 0.0553(7) Uani 1 1 d . . . H6 H 0.0573 0.5680 -0.2116 0.066 Uiso 1 1 calc R . . C11 C 0.3585(2) 0.6410(4) 0.05247(16) 0.0636(8) Uani 1 1 d . . . H11A H 0.3885 0.5782 0.0973 0.095 Uiso 1 1 calc R . . H11B H 0.3267 0.7466 0.0641 0.095 Uiso 1 1 calc R . . H11C H 0.4160 0.6662 0.0282 0.095 Uiso 1 1 calc R . . C13 C 0.0120(2) 0.7961(4) -0.07898(16) 0.0636(8) Uani 1 1 d . . . H13A H -0.0040 0.9062 -0.0607 0.095 Uiso 1 1 calc R . . H13B H -0.0278 0.7081 -0.0602 0.095 Uiso 1 1 calc R . . H13C H -0.0097 0.7962 -0.1322 0.095 Uiso 1 1 calc R . . Cl1 Cl 0.55084(5) 0.01204(9) 0.11416(4) 0.0620(2) Uani 1 1 d . . . Cl2 Cl 0.35896(6) 0.00011(10) 0.34313(4) 0.0681(2) Uani 1 1 d . . . N1 N 0.27808(16) 0.3602(3) 0.00037(11) 0.0445(5) Uani 1 1 d . . . O1 O 0.19680(19) 0.8824(2) -0.03775(14) 0.0875(8) 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 C15 0.0385(12) 0.0414(14) 0.0414(13) -0.0019(10) 0.0036(10) 0.0034(10) C20 0.0337(12) 0.0438(14) 0.0465(14) -0.0075(11) 0.0051(10) 0.0039(10) C19 0.0414(13) 0.0478(15) 0.0453(14) 0.0010(11) -0.0002(11) 0.0053(11) C18 0.0457(14) 0.0486(15) 0.0439(14) 0.0017(11) 0.0060(11) -0.0042(11) C17 0.0449(14) 0.0585(17) 0.0524(16) 0.0014(12) 0.0153(12) 0.0051(12) C16 0.0434(14) 0.0499(16) 0.0520(15) 0.0057(12) 0.0087(11) 0.0129(11) C14 0.0502(15) 0.0567(17) 0.0494(15) 0.0049(12) 0.0090(12) 0.0146(12) C10 0.0561(15) 0.0368(14) 0.0434(14) -0.0001(10) 0.0079(12) -0.0014(11) C7 0.0463(13) 0.0361(13) 0.0348(12) 0.0028(10) 0.0090(10) -0.0005(10) C8 0.0466(14) 0.0324(13) 0.0407(13) 0.0013(10) 0.0102(10) -0.0029(10) C9 0.0456(14) 0.0445(15) 0.0400(13) -0.0012(10) 0.0097(10) -0.0020(11) C1 0.0463(14) 0.0372(14) 0.0391(13) -0.0027(10) 0.0038(10) 0.0034(10) C2 0.0539(16) 0.0573(17) 0.0593(17) -0.0084(13) 0.0102(13) -0.0105(13) C3 0.0503(17) 0.077(2) 0.095(3) -0.0288(19) 0.0066(17) -0.0099(15) C12 0.0680(17) 0.0384(15) 0.0470(15) 0.0009(11) 0.0091(12) -0.0012(13) C4 0.069(2) 0.079(2) 0.077(2) -0.0276(19) -0.0237(18) 0.0219(19) C5 0.092(2) 0.063(2) 0.0490(17) -0.0047(14) -0.0079(16) 0.0211(18) C6 0.0704(18) 0.0477(16) 0.0432(14) 0.0021(12) 0.0052(13) 0.0026(13) C11 0.0552(17) 0.0633(18) 0.0649(19) -0.0087(15) 0.0005(14) -0.0104(14) C13 0.0725(19) 0.0530(17) 0.0616(18) -0.0011(13) 0.0092(15) 0.0196(14) Cl1 0.0477(4) 0.0794(5) 0.0569(4) -0.0093(3) 0.0092(3) 0.0224(3) Cl2 0.0669(5) 0.0855(6) 0.0512(4) 0.0152(4) 0.0129(3) -0.0009(4) N1 0.0473(12) 0.0429(12) 0.0399(11) 0.0032(9) 0.0044(9) 0.0060(9) O1 0.0933(16) 0.0363(12) 0.116(2) 0.0015(11) -0.0061(14) -0.0107(11) _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 C15 C16 1.391(3) . ? C15 C20 1.395(3) . ? C15 C14 1.513(3) . ? C20 C19 1.385(3) . ? C20 Cl1 1.743(2) . ? C19 C18 1.381(4) . ? C18 C17 1.378(3) . ? C18 Cl2 1.741(3) . ? C17 C16 1.381(3) . ? C14 N1 1.456(3) . ? C10 C7 1.361(3) . ? C10 N1 1.379(3) . ? C7 C8 1.439(3) . ? C7 C1 1.484(3) . ? C8 C9 1.386(3) . ? C8 C12 1.463(3) . ? C9 N1 1.361(3) . ? C9 C11 1.495(3) . ? C1 C2 1.386(3) . ? C1 C6 1.386(3) . ? C2 C3 1.387(4) . ? C3 C4 1.371(5) . ? C12 O1 1.221(3) . ? C12 C13 1.504(4) . ? C4 C5 1.372(5) . ? C5 C6 1.384(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 C16 C15 C20 116.7(2) . . ? C16 C15 C14 123.3(2) . . ? C20 C15 C14 120.1(2) . . ? C19 C20 C15 122.8(2) . . ? C19 C20 Cl1 118.01(18) . . ? C15 C20 Cl1 119.22(19) . . ? C18 C19 C20 118.2(2) . . ? C17 C18 C19 121.1(2) . . ? C17 C18 Cl2 119.3(2) . . ? C19 C18 Cl2 119.54(19) . . ? C18 C17 C16 119.4(2) . . ? C17 C16 C15 121.9(2) . . ? N1 C14 C15 114.8(2) . . ? C7 C10 N1 109.2(2) . . ? C10 C7 C8 106.1(2) . . ? C10 C7 C1 124.1(2) . . ? C8 C7 C1 129.4(2) . . ? C9 C8 C7 107.6(2) . . ? C9 C8 C12 123.4(2) . . ? C7 C8 C12 128.8(2) . . ? N1 C9 C8 107.6(2) . . ? N1 C9 C11 121.9(2) . . ? C8 C9 C11 130.5(2) . . ? C2 C1 C6 118.1(2) . . ? C2 C1 C7 120.9(2) . . ? C6 C1 C7 121.0(2) . . ? C1 C2 C3 120.7(3) . . ? C4 C3 C2 120.3(3) . . ? O1 C12 C8 121.3(2) . . ? O1 C12 C13 119.0(2) . . ? C8 C12 C13 119.7(2) . . ? C3 C4 C5 119.8(3) . . ? C4 C5 C6 120.0(3) . . ? C5 C6 C1 121.1(3) . . ? C9 N1 C10 109.42(19) . . ? C9 N1 C14 127.1(2) . . ? C10 N1 C14 123.3(2) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.237 _refine_diff_density_min -0.234 _refine_diff_density_rms 0.046