# Electronic Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2011 data_global _journal_name_full 'New J.Chem.' _journal_coden_cambridge 0440 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'K. C. Majumdar' _publ_contact_author_email kcm_ku@yahoo.co.in _publ_author_name K.Majumdar data_kcm _database_code_depnum_ccdc_archive 'CCDC 808360' #TrackingRef 'kcm.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H7.50 Cl0.50 N O2' _chemical_formula_weight 155.37 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 ? _symmetry_space_group_name_H-M ? 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' '-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 10.989(4) _cell_length_b 11.905(4) _cell_length_c 23.737(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3105.6(17) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 0.665 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.131 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 38174 _diffrn_reflns_av_R_equivalents 0.0441 _diffrn_reflns_av_sigmaI/netI 0.0179 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 23.95 _reflns_number_total 2353 _reflns_number_gt 2019 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0660P)^2^+2.2203P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2353 _refine_ls_number_parameters 219 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0486 _refine_ls_R_factor_gt 0.0413 _refine_ls_wR_factor_ref 0.1195 _refine_ls_wR_factor_gt 0.1134 _refine_ls_goodness_of_fit_ref 0.994 _refine_ls_restrained_S_all 0.994 _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 C15 C -0.0274(3) 0.4669(2) 0.08799(16) 0.0773(10) Uani 1 1 d . . . H15A H 0.0333 0.4158 0.1018 0.116 Uiso 1 1 calc R . . H15B H -0.0562 0.4416 0.0520 0.116 Uiso 1 1 calc R . . H15C H -0.0941 0.4698 0.1141 0.116 Uiso 1 1 calc R . . C16 C 0.3275(2) 0.7087(2) 0.10505(13) 0.0592(7) Uani 1 1 d . . . H16A H 0.3521 0.7840 0.0962 0.089 Uiso 1 1 calc R . . H16B H 0.3770 0.6565 0.0844 0.089 Uiso 1 1 calc R . . H16C H 0.3373 0.6958 0.1447 0.089 Uiso 1 1 calc R . . O8 O 0.15531(16) 0.73926(16) -0.00483(7) 0.0480(5) Uani 1 1 d . . . H9 H -0.107(3) 0.978(3) 0.1405(13) 0.075(9) Uiso 1 1 d . . . H8B H -0.199(2) 0.934(2) 0.0434(10) 0.054(7) Uiso 1 1 d . . . H8A H -0.080(2) 1.007(3) 0.0361(12) 0.067(8) Uiso 1 1 d . . . H13 H 0.1817(19) 0.842(2) 0.0575(8) 0.028(5) Uiso 1 1 d . . . H8 H 0.212(3) 0.766(3) -0.0172(13) 0.071(11) Uiso 1 1 d . . . Cl1 Cl 0.15978(7) 0.71411(6) 0.35205(3) 0.0664(3) Uani 1 1 d . . . O2 O -0.14886(14) 0.64671(14) 0.04759(7) 0.0485(4) Uani 1 1 d . . . N2 N 0.19998(16) 0.69308(15) 0.08959(8) 0.0394(5) Uani 1 1 d . . . O1 O -0.04881(15) 0.85019(13) 0.02504(6) 0.0478(4) Uani 1 1 d . . . N1 N 0.02606(16) 0.57948(15) 0.08209(8) 0.0426(5) Uani 1 1 d . . . C13 C 0.14448(19) 0.77294(19) 0.05147(9) 0.0362(5) Uani 1 1 d . . . O3 O 0.20079(16) 0.51403(15) 0.12101(10) 0.0714(6) Uani 1 1 d . . . C10 C 0.00989(19) 0.78138(17) 0.06542(8) 0.0337(5) Uani 1 1 d . . . C7 C -0.01618(19) 0.83852(18) 0.12189(9) 0.0381(5) Uani 1 1 d . . . C11 C -0.04510(19) 0.66429(18) 0.06320(8) 0.0344(5) Uani 1 1 d . . . C4 C 0.0309(2) 0.80217(18) 0.17758(9) 0.0396(5) Uani 1 1 d . . . C5 C -0.0154(2) 0.7101(2) 0.20557(10) 0.0521(7) Uani 1 1 d . . . H5 H -0.0747 0.6663 0.1883 0.063 Uiso 1 1 calc R . . C12 C 0.1491(2) 0.59253(19) 0.09905(10) 0.0434(6) Uani 1 1 d . . . C1 C 0.1118(2) 0.7462(2) 0.28405(10) 0.0477(6) Uani 1 1 d . . . C6 C 0.0247(2) 0.6817(2) 0.25884(10) 0.0544(7) Uani 1 1 d . . . H6 H -0.0073 0.6195 0.2773 0.065 Uiso 1 1 calc R . . C3 C 0.1197(3) 0.8650(2) 0.20403(10) 0.0544(7) Uani 1 1 d . . . H3 H 0.1527 0.9270 0.1857 0.065 Uiso 1 1 calc R . . C9 C -0.0849(2) 0.9265(2) 0.11207(12) 0.0512(6) Uani 1 1 d . . . C2 C 0.1601(3) 0.8372(2) 0.25718(11) 0.0594(7) Uani 1 1 d . . . H2 H 0.2199 0.8802 0.2746 0.071 Uiso 1 1 calc R . . C8 C -0.1125(3) 0.9406(2) 0.05180(12) 0.0540(7) 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 0.0595(17) 0.0379(14) 0.134(3) 0.0145(17) -0.0230(18) -0.0108(13) C16 0.0348(13) 0.0737(19) 0.0689(18) 0.0043(14) -0.0111(12) -0.0076(12) O8 0.0434(10) 0.0630(11) 0.0376(9) -0.0017(8) 0.0093(8) -0.0099(9) Cl1 0.0841(5) 0.0712(5) 0.0440(4) 0.0081(3) -0.0139(3) -0.0104(4) O2 0.0325(9) 0.0527(10) 0.0602(11) 0.0025(8) -0.0103(7) -0.0021(7) N2 0.0282(9) 0.0433(11) 0.0467(11) 0.0026(9) -0.0056(8) -0.0022(8) O1 0.0548(10) 0.0457(9) 0.0429(9) 0.0127(7) -0.0032(7) 0.0126(8) N1 0.0345(10) 0.0306(10) 0.0626(12) 0.0047(9) -0.0095(9) -0.0019(8) C13 0.0374(12) 0.0358(13) 0.0353(12) 0.0016(9) 0.0012(9) -0.0065(10) O3 0.0548(11) 0.0516(11) 0.1078(16) 0.0246(11) -0.0263(11) 0.0079(9) C10 0.0351(11) 0.0354(12) 0.0307(11) 0.0069(9) -0.0030(9) 0.0024(9) C7 0.0406(12) 0.0336(12) 0.0402(12) 0.0018(9) 0.0057(10) -0.0021(10) C11 0.0311(12) 0.0396(12) 0.0326(11) 0.0003(9) -0.0006(9) 0.0013(10) C4 0.0453(13) 0.0382(12) 0.0354(12) -0.0024(10) 0.0073(10) -0.0026(10) C5 0.0578(15) 0.0527(15) 0.0459(14) 0.0033(12) -0.0046(12) -0.0192(12) C12 0.0363(12) 0.0405(13) 0.0535(14) 0.0021(11) -0.0076(10) 0.0046(11) C1 0.0552(15) 0.0536(14) 0.0343(12) 0.0007(11) -0.0001(11) -0.0059(13) C6 0.0677(17) 0.0519(14) 0.0435(14) 0.0112(12) 0.0005(12) -0.0166(13) C3 0.0681(16) 0.0505(15) 0.0445(14) 0.0047(12) 0.0039(12) -0.0222(13) C9 0.0569(15) 0.0397(14) 0.0570(16) -0.0016(12) 0.0106(12) 0.0030(12) C2 0.0673(18) 0.0644(17) 0.0466(15) 0.0002(13) -0.0088(12) -0.0262(14) C8 0.0506(16) 0.0425(15) 0.0690(18) 0.0119(13) 0.0035(13) 0.0104(13) _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 N1 1.470(3) . ? C16 N2 1.461(3) . ? O8 C13 1.400(3) . ? Cl1 C1 1.741(2) . ? O2 C11 1.217(3) . ? N2 C12 1.340(3) . ? N2 C13 1.447(3) . ? O1 C10 1.416(2) . ? O1 C8 1.432(3) . ? N1 C11 1.354(3) . ? N1 C12 1.420(3) . ? C13 C10 1.519(3) . ? O3 C12 1.211(3) . ? C10 C11 1.520(3) . ? C10 C7 1.530(3) . ? C7 C9 1.313(3) . ? C7 C4 1.484(3) . ? C4 C5 1.379(3) . ? C4 C3 1.381(3) . ? C5 C6 1.381(4) . ? C1 C2 1.365(4) . ? C1 C6 1.365(4) . ? C3 C2 1.378(4) . ? C9 C8 1.472(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 C12 N2 C13 121.06(18) . . ? C12 N2 C16 118.1(2) . . ? C13 N2 C16 118.54(19) . . ? C10 O1 C8 110.92(17) . . ? C11 N1 C12 124.25(18) . . ? C11 N1 C15 118.74(19) . . ? C12 N1 C15 116.96(19) . . ? O8 C13 N2 111.89(19) . . ? O8 C13 C10 108.05(18) . . ? N2 C13 C10 108.51(17) . . ? O1 C10 C11 109.01(17) . . ? O1 C10 C13 109.52(17) . . ? C11 C10 C13 108.59(17) . . ? O1 C10 C7 104.50(17) . . ? C11 C10 C7 111.32(17) . . ? C13 C10 C7 113.75(18) . . ? C9 C7 C4 126.3(2) . . ? C9 C7 C10 107.9(2) . . ? C4 C7 C10 125.84(19) . . ? O2 C11 N1 120.9(2) . . ? O2 C11 C10 122.73(19) . . ? N1 C11 C10 116.28(18) . . ? C5 C4 C3 118.2(2) . . ? C5 C4 C7 122.2(2) . . ? C3 C4 C7 119.6(2) . . ? C6 C5 C4 121.2(2) . . ? O3 C12 N2 124.5(2) . . ? O3 C12 N1 118.9(2) . . ? N2 C12 N1 116.58(19) . . ? C2 C1 C6 121.0(2) . . ? C2 C1 Cl1 119.31(19) . . ? C6 C1 Cl1 119.71(19) . . ? C1 C6 C5 119.2(2) . . ? C2 C3 C4 120.9(2) . . ? C7 C9 C8 112.5(2) . . ? C1 C2 C3 119.5(2) . . ? O1 C8 C9 104.2(2) . . ? _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 23.95 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 0.370 _refine_diff_density_min -0.402 _refine_diff_density_rms 0.043