# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_coden_Cambridge 182 _publ_contact_author_name 'Irishi Namboothiri' _publ_contact_author_address ; Irishi N. N. Namboothiri Department of Chemistry Indian Institute of Technology Bombay Powai Mumbai 400 076 India ; _publ_contact_author_phone '+91 22 2576 7196' _publ_contact_author_fax '+91 22 2576 7152' _publ_contact_author_email irishi@chem.iitb.ac.in _publ_requested_journal 'Chemical Communications' # 2. TITLE AND AUTHOR LIST _publ_section_title ; The Morita-Baylis-Hillman adducts of conjugated nitroalkenes with other activated alkenes: synthesis and anticancer activity studies ; loop_ _publ_author_name _publ_author_address 'Irishi N. N. Namboothiri' ; Department of Chemistry Indian Institute of Technology Bombay Powai Mumbai 400 076 India ; 'Mamta Dadwal' ; Department of Chemistry Indian Institute of Technology Bombay Powai Mumbai 400 076 India ; 'Renu Mohan' ; School of Biosciences and Bioengineering Indian Institute of Technology Bombay Powai Mumbai 400 076 India ; 'Dulal Panda' ; School of Biosciences and Bioengineering Indian Institute of Technology Bombay Powai Mumbai 400 076 India ; 'Shaik M. Mobin' ; National Single Crystal X-ray Diffraction Faciltiy Indian Institute of Technology Bombay Powai Mumbai 400 076 India ; #============================================================================== data_iin19a _database_code_depnum_ccdc_archive 'CCDC 283074' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H13 N O3' _chemical_formula_weight 219.23 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' O O 0.0106 0.0060 '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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.2530(10) _cell_length_b 7.9810(7) _cell_length_c 10.7050(9) _cell_angle_alpha 106.198(7) _cell_angle_beta 104.883(9) _cell_angle_gamma 97.193(9) _cell_volume 562.02(10) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 6.4400 _cell_measurement_theta_max 15.6400 _exptl_crystal_description Block _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.295 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 232 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type Psi-scan _exptl_absorpt_correction_T_min 0.9680 _exptl_absorpt_correction_T_max 0.9770 _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 'Nonius MACH3' _diffrn_measurement_method \w/q-scan _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 3600 _diffrn_standards_decay_% <3% _diffrn_reflns_number 2153 _diffrn_reflns_av_R_equivalents 0.0171 _diffrn_reflns_av_sigmaI/netI 0.0473 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 24.96 _reflns_number_total 1982 _reflns_number_gt 1254 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Argus (Nonius, MACH3 software)' _computing_cell_refinement 'Argus (Nonius, MACH3 software)' _computing_data_reduction 'Maxus (Nonius software)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Ortep _computing_publication_material Shelx97 _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 w=1/[\s^2^(Fo^2^)+(0.0567P)^2^+0.0844P] 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 riding-model _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1982 _refine_ls_number_parameters 146 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1038 _refine_ls_R_factor_gt 0.0453 _refine_ls_wR_factor_ref 0.1201 _refine_ls_wR_factor_gt 0.1010 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.012 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.0711(3) 0.5555(3) 0.69263(19) 0.0771(6) Uani 1 d . . . O2 O 0.2757(3) 0.6116(3) 0.89119(19) 0.0774(6) Uani 1 d . . . O3 O 0.8410(3) 0.9954(2) 1.10224(17) 0.0741(6) Uani 1 d . . . N1 N 0.2341(3) 0.6173(3) 0.7740(2) 0.0550(5) Uani 1 d . . . C1 C 1.0206(3) 0.7704(3) 1.1117(2) 0.0580(6) Uani 1 d . . . H1A H 1.0957 0.8536 1.1997 0.070 Uiso 1 calc R . . H1B H 1.1026 0.7499 1.0538 0.070 Uiso 1 calc R . . H1C H 0.9698 0.6598 1.1220 0.070 Uiso 1 calc R . . C2 C 0.8570(3) 0.8445(3) 1.0496(2) 0.0464(5) Uani 1 d . . . C3 C 0.7101(3) 0.7230(3) 0.9179(2) 0.0506(6) Uani 1 d . . . H3A H 0.6417 0.6238 0.9355 0.061 Uiso 1 calc R . . H3B H 0.7785 0.6747 0.8538 0.061 Uiso 1 calc R . . C4 C 0.5615(3) 0.8175(3) 0.8532(2) 0.0476(6) Uani 1 d . . . H4A H 0.5104 0.8824 0.9232 0.057 Uiso 1 calc R . . H4B H 0.6295 0.9049 0.8242 0.057 Uiso 1 calc R . . C5 C 0.3933(3) 0.7027(3) 0.7344(2) 0.0422(5) Uani 1 d . . . C6 C 0.3606(3) 0.6707(3) 0.6010(2) 0.0434(5) Uani 1 d . . . H6 H 0.2378 0.6032 0.5457 0.052 Uiso 1 calc R . . C7 C 0.4903(3) 0.7266(3) 0.5292(2) 0.0414(5) Uani 1 d . . . C8 C 0.6936(3) 0.7691(3) 0.5810(2) 0.0515(6) Uani 1 d . . . H8 H 0.7542 0.7643 0.6674 0.062 Uiso 1 calc R . . C9 C 0.8053(3) 0.8178(3) 0.5056(3) 0.0617(7) Uani 1 d . . . H9 H 0.9407 0.8455 0.5414 0.074 Uiso 1 calc R . . C10 C 0.7183(4) 0.8259(3) 0.3778(3) 0.0663(7) Uani 1 d . . . H10 H 0.7943 0.8617 0.3281 0.080 Uiso 1 calc R . . C11 C 0.5192(4) 0.7812(3) 0.3241(2) 0.0650(7) Uani 1 d . . . H11 H 0.4599 0.7847 0.2371 0.078 Uiso 1 calc R . . C12 C 0.4069(3) 0.7312(3) 0.3986(2) 0.0554(6) Uani 1 d . . . H12 H 0.2718 0.6998 0.3605 0.066 Uiso 1 calc 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_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0447(10) 0.0962(14) 0.0839(13) 0.0267(11) 0.0206(10) -0.0035(9) O2 0.0802(13) 0.1000(15) 0.0654(12) 0.0385(11) 0.0355(10) 0.0121(11) O3 0.0799(13) 0.0608(12) 0.0582(11) -0.0006(9) 0.0018(9) 0.0179(9) N1 0.0511(13) 0.0579(13) 0.0607(13) 0.0189(10) 0.0262(11) 0.0102(10) C1 0.0481(14) 0.0661(16) 0.0557(15) 0.0224(12) 0.0085(12) 0.0066(12) C2 0.0489(13) 0.0524(14) 0.0394(12) 0.0158(10) 0.0167(10) 0.0065(11) C3 0.0526(13) 0.0485(13) 0.0460(13) 0.0117(10) 0.0108(10) 0.0117(11) C4 0.0523(13) 0.0432(13) 0.0435(12) 0.0090(10) 0.0138(10) 0.0099(10) C5 0.0378(12) 0.0408(12) 0.0491(13) 0.0133(10) 0.0162(10) 0.0089(9) C6 0.0359(11) 0.0438(12) 0.0461(13) 0.0121(10) 0.0091(10) 0.0056(9) C7 0.0389(12) 0.0384(12) 0.0433(12) 0.0103(9) 0.0109(10) 0.0061(9) C8 0.0429(13) 0.0599(15) 0.0486(13) 0.0159(11) 0.0123(11) 0.0072(11) C9 0.0442(14) 0.0692(16) 0.0684(17) 0.0180(13) 0.0217(13) 0.0012(12) C10 0.0750(18) 0.0663(17) 0.0678(17) 0.0248(13) 0.0386(15) 0.0085(14) C11 0.0748(19) 0.0760(17) 0.0524(15) 0.0325(13) 0.0196(13) 0.0183(14) C12 0.0497(14) 0.0645(15) 0.0509(15) 0.0219(12) 0.0107(12) 0.0114(12) _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 O1 N1 1.219(2) . ? O2 N1 1.228(2) . ? O3 C2 1.213(3) . ? N1 C5 1.481(3) . ? C1 C2 1.480(3) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.507(3) . ? C3 C4 1.524(3) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.490(3) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.329(3) . ? C6 C7 1.461(3) . ? C6 H6 0.9300 . ? C7 C12 1.387(3) . ? C7 C8 1.395(3) . ? C8 C9 1.375(3) . ? C8 H8 0.9300 . ? C9 C10 1.375(3) . ? C9 H9 0.9300 . ? C10 C11 1.368(4) . ? C10 H10 0.9300 . ? C11 C12 1.374(3) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? 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 O1 N1 O2 122.6(2) . . ? O1 N1 C5 120.72(19) . . ? O2 N1 C5 116.70(19) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O3 C2 C1 121.8(2) . . ? O3 C2 C3 121.5(2) . . ? C1 C2 C3 116.8(2) . . ? C2 C3 C4 112.86(18) . . ? C2 C3 H3A 109.0 . . ? C4 C3 H3A 109.0 . . ? C2 C3 H3B 109.0 . . ? C4 C3 H3B 109.0 . . ? H3A C3 H3B 107.8 . . ? C5 C4 C3 116.65(17) . . ? C5 C4 H4A 108.1 . . ? C3 C4 H4A 108.1 . . ? C5 C4 H4B 108.1 . . ? C3 C4 H4B 108.1 . . ? H4A C4 H4B 107.3 . . ? C6 C5 N1 115.70(19) . . ? C6 C5 C4 130.8(2) . . ? N1 C5 C4 113.46(18) . . ? C5 C6 C7 129.1(2) . . ? C5 C6 H6 115.4 . . ? C7 C6 H6 115.4 . . ? C12 C7 C8 117.5(2) . . ? C12 C7 C6 118.02(19) . . ? C8 C7 C6 124.38(19) . . ? C9 C8 C7 120.7(2) . . ? C9 C8 H8 119.6 . . ? C7 C8 H8 119.6 . . ? C8 C9 C10 120.4(2) . . ? C8 C9 H9 119.8 . . ? C10 C9 H9 119.8 . . ? C11 C10 C9 119.7(2) . . ? C11 C10 H10 120.1 . . ? C9 C10 H10 120.1 . . ? C10 C11 C12 120.1(2) . . ? C10 C11 H11 120.0 . . ? C12 C11 H11 120.0 . . ? C11 C12 C7 121.5(2) . . ? C11 C12 H12 119.3 . . ? C7 C12 H12 119.3 . . ? 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 O3 C2 C3 C4 7.2(3) . . . . ? C1 C2 C3 C4 -173.17(19) . . . . ? C2 C3 C4 C5 -171.11(18) . . . . ? O1 N1 C5 C6 -15.1(3) . . . . ? O2 N1 C5 C6 164.5(2) . . . . ? O1 N1 C5 C4 162.5(2) . . . . ? O2 N1 C5 C4 -17.9(3) . . . . ? C3 C4 C5 C6 -100.9(3) . . . . ? C3 C4 C5 N1 82.0(2) . . . . ? N1 C5 C6 C7 -176.49(19) . . . . ? C4 C5 C6 C7 6.4(4) . . . . ? C5 C6 C7 C12 -158.4(2) . . . . ? C5 C6 C7 C8 24.3(4) . . . . ? C12 C7 C8 C9 1.6(3) . . . . ? C6 C7 C8 C9 178.9(2) . . . . ? C7 C8 C9 C10 0.2(4) . . . . ? C8 C9 C10 C11 -1.5(4) . . . . ? C9 C10 C11 C12 1.1(4) . . . . ? C10 C11 C12 C7 0.8(4) . . . . ? C8 C7 C12 C11 -2.0(3) . . . . ? C6 C7 C12 C11 -179.6(2) . . . . ? 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 C1 H1B O2 0.96 2.49 3.430(3) 164.7 1_655 C1 H1C O2 0.96 2.57 3.491(3) 160.3 2_667 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.96 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.142 _refine_diff_density_min -0.226 _refine_diff_density_rms 0.041