# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2011 data_publication_text _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _publ_contact_author_name B.Sridhar _publ_contact_author_address ;Laboratory of X-ray Crystallography Indian Institute of Chemical Technology Hyderabad- 500 007 India ; _publ_contact_author_email sshiya@yahoo.com _publ_contact_author_phone 09104027193118 _publ_contact_author_fax 09104027193118 loop_ _publ_author_name _publ_author_address 'Venkata Subba Reddy Basireddy' ;Organic Chemistry Division Indian Institute of Chemical Technology Hyderabad- 500 007 India ; 'Prashant Borkar' ;Organic Chemistry Division Indian Institute of Chemical Technology Hyderabad- 500 007 India ; 'Jhillu Yadav' ;Organic Chemistry Division Indian Institute of Chemical Technology Hyderabad- 500 007 India ; 'Purushotham Pothula' ;Laboratory of X-ray Crystallography Indian Institute of Chemical Technology Hyderabad- 500 007 India ; 'Ajit Kunwar' '' 'Sridhar, B.' '' 'Ren Gre' '' data_aj73 _database_code_depnum_ccdc_archive 'CCDC 833511' #TrackingRef '6215_web_deposit_cif_file_0_B.Sridhar_1310204300.aj73f.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ;(4R,4aR,10bS)-4-(4-methoxyphenyl)-2,4,4a,5,6,10b-hexahydro-1H- benzo[f]isochromene ; _chemical_name_common ? _chemical_formula_moiety 'C20 H22 O2' _chemical_formula_sum 'C20 H22 O2' _chemical_melting_point ? _exptl_crystal_description block _exptl_crystal_colour colorless _diffrn_ambient_temperature 294(2) _chemical_formula_weight 294.38 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_int_tables_number 14 _chemical_absolute_configuration ? _symmetry_space_group_name_Hall '-P 2ybc' 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 18.554(4) _cell_length_b 6.2560(15) _cell_length_c 13.851(3) _cell_angle_alpha 90.00 _cell_angle_beta 100.778(4) _cell_angle_gamma 90.00 _cell_volume 1579.4(7) _cell_formula_units_Z 4 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 2544 _cell_measurement_theta_min 2.23 _cell_measurement_theta_max 23.78 _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.238 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD Area Detector' _diffrn_measurement_device 'Bruker SMART APEX CCD area-detector' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12095 _diffrn_reflns_av_R_equivalents 0.0371 _diffrn_reflns_av_sigmaI/netI 0.0390 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.12 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2784 _reflns_number_gt 2030 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SAINT (Bruker, 2001)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL/PC (Sheldrick, 1990)' _computing_publication_material SHELXL97 _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^)+(0.0393P)^2^+0.2762P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2784 _refine_ls_number_parameters 200 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0798 _refine_ls_R_factor_gt 0.0554 _refine_ls_wR_factor_ref 0.1233 _refine_ls_wR_factor_gt 0.1105 _refine_ls_goodness_of_fit_ref 1.120 _refine_ls_restrained_S_all 1.120 _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 C1 C 0.38795(12) 1.0984(3) 0.52518(16) 0.0591(6) Uani 1 1 d . . . C2 C 0.44984(14) 1.2275(4) 0.53492(19) 0.0736(7) Uani 1 1 d . . . H2 H 0.4706 1.2537 0.4799 0.088 Uiso 1 1 calc R . . C3 C 0.48127(14) 1.3173(4) 0.6227(2) 0.0763(7) Uani 1 1 d . . . H3 H 0.5226 1.4033 0.6268 0.092 Uiso 1 1 calc R . . C4 C 0.45177(14) 1.2802(4) 0.70465(19) 0.0729(7) Uani 1 1 d . . . H4 H 0.4728 1.3403 0.7647 0.088 Uiso 1 1 calc R . . C5 C 0.39088(14) 1.1534(4) 0.69698(17) 0.0649(6) Uani 1 1 d . . . H5 H 0.3710 1.1284 0.7528 0.078 Uiso 1 1 calc R . . C6 C 0.35768(12) 1.0606(3) 0.60848(15) 0.0548(6) Uani 1 1 d . . . C7 C 0.29251(12) 0.9146(3) 0.60507(14) 0.0555(6) Uani 1 1 d . . . H7 H 0.2578 0.9868 0.6395 0.067 Uiso 1 1 calc R . . C8 C 0.31574(13) 0.7065(4) 0.65987(16) 0.0642(6) Uani 1 1 d . . . H8A H 0.3542 0.6390 0.6319 0.077 Uiso 1 1 calc R . . H8B H 0.3353 0.7378 0.7284 0.077 Uiso 1 1 calc R . . C9 C 0.25218(13) 0.5564(4) 0.65322(17) 0.0715(7) Uani 1 1 d . . . H9A H 0.2684 0.4249 0.6876 0.086 Uiso 1 1 calc R . . H9B H 0.2150 0.6203 0.6849 0.086 Uiso 1 1 calc R . . C10 C 0.19215(12) 0.6960(3) 0.50161(16) 0.0595(6) Uani 1 1 d . . . H10 H 0.1550 0.7567 0.5356 0.071 Uiso 1 1 calc R . . C11 C 0.25201(11) 0.8653(3) 0.50091(15) 0.0542(5) Uani 1 1 d . . . H11 H 0.2272 0.9971 0.4749 0.065 Uiso 1 1 calc R . . C12 C 0.30671(12) 0.8108(4) 0.43575(15) 0.0604(6) Uani 1 1 d . . . H12A H 0.2808 0.7693 0.3710 0.073 Uiso 1 1 calc R . . H12B H 0.3370 0.6916 0.4636 0.073 Uiso 1 1 calc R . . C13 C 0.35471(13) 1.0040(4) 0.42722(16) 0.0687(7) Uani 1 1 d . . . H13A H 0.3938 0.9622 0.3933 0.082 Uiso 1 1 calc R . . H13B H 0.3255 1.1123 0.3878 0.082 Uiso 1 1 calc R . . C14 C 0.15466(11) 0.6305(3) 0.40038(17) 0.0576(6) Uani 1 1 d . . . C15 C 0.10456(12) 0.7644(4) 0.34339(19) 0.0657(6) Uani 1 1 d . . . H15 H 0.0927 0.8937 0.3696 0.079 Uiso 1 1 calc R . . C16 C 0.07204(12) 0.7112(4) 0.24932(19) 0.0681(7) Uani 1 1 d . . . H16 H 0.0385 0.8041 0.2126 0.082 Uiso 1 1 calc R . . C17 C 0.08889(11) 0.5198(4) 0.20873(18) 0.0595(6) Uani 1 1 d . . . C18 C 0.13741(13) 0.3832(4) 0.26420(19) 0.0679(7) Uani 1 1 d . . . H18 H 0.1485 0.2526 0.2384 0.082 Uiso 1 1 calc R . . C19 C 0.16991(13) 0.4399(4) 0.35873(19) 0.0683(7) Uani 1 1 d . . . H19 H 0.2032 0.3463 0.3954 0.082 Uiso 1 1 calc R . . C20 C 0.06836(16) 0.2867(4) 0.0695(2) 0.0909(9) Uani 1 1 d . . . H20A H 0.1200 0.2742 0.0703 0.136 Uiso 1 1 calc R . . H20B H 0.0422 0.2838 0.0027 0.136 Uiso 1 1 calc R . . H20C H 0.0525 0.1696 0.1052 0.136 Uiso 1 1 calc R . . O1 O 0.22118(8) 0.5092(2) 0.55345(12) 0.0679(5) Uani 1 1 d . . . O2 O 0.05401(8) 0.4824(3) 0.11408(13) 0.0751(5) 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 C1 0.0656(15) 0.0580(13) 0.0558(14) 0.0082(11) 0.0164(11) 0.0051(11) C2 0.0789(17) 0.0738(17) 0.0725(17) 0.0086(13) 0.0251(14) -0.0095(14) C3 0.0758(17) 0.0665(16) 0.0853(19) 0.0023(14) 0.0118(15) -0.0080(13) C4 0.0817(18) 0.0622(15) 0.0712(17) -0.0044(12) 0.0049(14) 0.0044(14) C5 0.0786(17) 0.0628(14) 0.0544(15) 0.0037(11) 0.0157(12) 0.0136(13) C6 0.0596(14) 0.0511(12) 0.0566(14) 0.0096(10) 0.0181(11) 0.0139(10) C7 0.0601(14) 0.0600(13) 0.0514(13) 0.0056(10) 0.0231(11) 0.0144(11) C8 0.0704(15) 0.0722(15) 0.0532(13) 0.0178(11) 0.0200(11) 0.0064(12) C9 0.0797(18) 0.0735(16) 0.0661(17) 0.0260(13) 0.0259(13) 0.0084(13) C10 0.0578(14) 0.0592(13) 0.0655(15) 0.0107(11) 0.0218(12) 0.0121(11) C11 0.0566(13) 0.0488(12) 0.0600(14) 0.0138(10) 0.0182(11) 0.0114(10) C12 0.0627(14) 0.0707(15) 0.0508(13) 0.0043(11) 0.0180(11) 0.0008(12) C13 0.0733(16) 0.0820(17) 0.0556(14) 0.0090(12) 0.0243(12) -0.0070(13) C14 0.0486(13) 0.0525(13) 0.0758(16) 0.0111(11) 0.0219(11) 0.0069(10) C15 0.0543(14) 0.0589(14) 0.0844(18) 0.0003(12) 0.0139(13) 0.0120(11) C16 0.0510(14) 0.0621(15) 0.0889(19) 0.0117(13) 0.0072(13) 0.0133(11) C17 0.0465(13) 0.0605(14) 0.0728(16) 0.0069(12) 0.0141(12) -0.0022(11) C18 0.0684(16) 0.0521(13) 0.0843(18) 0.0028(12) 0.0169(14) 0.0094(12) C19 0.0673(16) 0.0592(15) 0.0771(17) 0.0153(13) 0.0104(13) 0.0161(12) C20 0.096(2) 0.089(2) 0.086(2) -0.0141(16) 0.0128(16) 0.0075(16) O1 0.0728(10) 0.0599(9) 0.0723(11) 0.0199(8) 0.0174(8) 0.0046(8) O2 0.0650(11) 0.0740(11) 0.0837(12) -0.0001(9) 0.0070(9) 0.0041(9) _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 C1 C2 1.390(3) . ? C1 C6 1.394(3) . ? C1 C13 1.502(3) . ? C2 C3 1.367(3) . ? C2 H2 0.9300 . ? C3 C4 1.369(3) . ? C3 H3 0.9300 . ? C4 C5 1.368(3) . ? C4 H4 0.9300 . ? C5 C6 1.392(3) . ? C5 H5 0.9300 . ? C6 C7 1.509(3) . ? C7 C8 1.528(3) . ? C7 C11 1.528(3) . ? C7 H7 0.9800 . ? C8 C9 1.497(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 O1 1.425(3) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 O1 1.424(2) . ? C10 C14 1.501(3) . ? C10 C11 1.536(3) . ? C10 H10 0.9800 . ? C11 C12 1.518(3) . ? C11 H11 0.9800 . ? C12 C13 1.519(3) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C19 1.377(3) . ? C14 C15 1.383(3) . ? C15 C16 1.371(3) . ? C15 H15 0.9300 . ? C16 C17 1.383(3) . ? C16 H16 0.9300 . ? C17 C18 1.369(3) . ? C17 O2 1.369(3) . ? C18 C19 1.382(3) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 O2 1.419(3) . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? 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 C2 C1 C6 118.1(2) . . ? C2 C1 C13 120.6(2) . . ? C6 C1 C13 121.3(2) . . ? C3 C2 C1 122.2(2) . . ? C3 C2 H2 118.9 . . ? C1 C2 H2 118.9 . . ? C2 C3 C4 119.9(2) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C5 C4 C3 119.1(2) . . ? C5 C4 H4 120.5 . . ? C3 C4 H4 120.5 . . ? C4 C5 C6 122.2(2) . . ? C4 C5 H5 118.9 . . ? C6 C5 H5 118.9 . . ? C5 C6 C1 118.5(2) . . ? C5 C6 C7 120.00(19) . . ? C1 C6 C7 121.4(2) . . ? C6 C7 C8 110.51(17) . . ? C6 C7 C11 113.66(17) . . ? C8 C7 C11 109.87(18) . . ? C6 C7 H7 107.5 . . ? C8 C7 H7 107.5 . . ? C11 C7 H7 107.5 . . ? C9 C8 C7 110.98(18) . . ? C9 C8 H8A 109.4 . . ? C7 C8 H8A 109.4 . . ? C9 C8 H8B 109.4 . . ? C7 C8 H8B 109.4 . . ? H8A C8 H8B 108.0 . . ? O1 C9 C8 111.11(17) . . ? O1 C9 H9A 109.4 . . ? C8 C9 H9A 109.4 . . ? O1 C9 H9B 109.4 . . ? C8 C9 H9B 109.4 . . ? H9A C9 H9B 108.0 . . ? O1 C10 C14 108.21(18) . . ? O1 C10 C11 111.30(17) . . ? C14 C10 C11 113.06(17) . . ? O1 C10 H10 108.0 . . ? C14 C10 H10 108.0 . . ? C11 C10 H10 108.0 . . ? C12 C11 C7 109.96(17) . . ? C12 C11 C10 114.44(18) . . ? C7 C11 C10 111.21(17) . . ? C12 C11 H11 106.9 . . ? C7 C11 H11 106.9 . . ? C10 C11 H11 106.9 . . ? C11 C12 C13 109.56(18) . . ? C11 C12 H12A 109.8 . . ? C13 C12 H12A 109.8 . . ? C11 C12 H12B 109.8 . . ? C13 C12 H12B 109.8 . . ? H12A C12 H12B 108.2 . . ? C1 C13 C12 112.97(18) . . ? C1 C13 H13A 109.0 . . ? C12 C13 H13A 109.0 . . ? C1 C13 H13B 109.0 . . ? C12 C13 H13B 109.0 . . ? H13A C13 H13B 107.8 . . ? C19 C14 C15 117.0(2) . . ? C19 C14 C10 122.2(2) . . ? C15 C14 C10 120.8(2) . . ? C16 C15 C14 121.7(2) . . ? C16 C15 H15 119.2 . . ? C14 C15 H15 119.2 . . ? C15 C16 C17 120.3(2) . . ? C15 C16 H16 119.9 . . ? C17 C16 H16 119.9 . . ? C18 C17 O2 125.0(2) . . ? C18 C17 C16 119.2(2) . . ? O2 C17 C16 115.8(2) . . ? C17 C18 C19 119.7(2) . . ? C17 C18 H18 120.1 . . ? C19 C18 H18 120.1 . . ? C14 C19 C18 122.2(2) . . ? C14 C19 H19 118.9 . . ? C18 C19 H19 118.9 . . ? O2 C20 H20A 109.5 . . ? O2 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O2 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C10 O1 C9 111.40(17) . . ? C17 O2 C20 118.10(19) . . ? 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 C6 C1 C2 C3 -0.1(3) . . . . ? C13 C1 C2 C3 179.6(2) . . . . ? C1 C2 C3 C4 0.2(4) . . . . ? C2 C3 C4 C5 -0.1(4) . . . . ? C3 C4 C5 C6 -0.1(3) . . . . ? C4 C5 C6 C1 0.2(3) . . . . ? C4 C5 C6 C7 177.4(2) . . . . ? C2 C1 C6 C5 -0.1(3) . . . . ? C13 C1 C6 C5 -179.7(2) . . . . ? C2 C1 C6 C7 -177.31(19) . . . . ? C13 C1 C6 C7 3.1(3) . . . . ? C5 C6 C7 C8 -68.7(2) . . . . ? C1 C6 C7 C8 108.4(2) . . . . ? C5 C6 C7 C11 167.23(18) . . . . ? C1 C6 C7 C11 -15.6(3) . . . . ? C6 C7 C8 C9 -177.50(18) . . . . ? C11 C7 C8 C9 -51.3(2) . . . . ? C7 C8 C9 O1 58.2(2) . . . . ? C6 C7 C11 C12 45.5(2) . . . . ? C8 C7 C11 C12 -78.9(2) . . . . ? C6 C7 C11 C10 173.30(16) . . . . ? C8 C7 C11 C10 48.9(2) . . . . ? O1 C10 C11 C12 71.7(2) . . . . ? C14 C10 C11 C12 -50.4(2) . . . . ? O1 C10 C11 C7 -53.7(2) . . . . ? C14 C10 C11 C7 -175.72(16) . . . . ? C7 C11 C12 C13 -63.6(2) . . . . ? C10 C11 C12 C13 170.37(17) . . . . ? C2 C1 C13 C12 159.5(2) . . . . ? C6 C1 C13 C12 -20.9(3) . . . . ? C11 C12 C13 C1 50.8(3) . . . . ? O1 C10 C14 C19 -20.4(3) . . . . ? C11 C10 C14 C19 103.4(2) . . . . ? O1 C10 C14 C15 161.81(19) . . . . ? C11 C10 C14 C15 -74.4(2) . . . . ? C19 C14 C15 C16 -0.7(3) . . . . ? C10 C14 C15 C16 177.3(2) . . . . ? C14 C15 C16 C17 -0.1(4) . . . . ? C15 C16 C17 C18 1.1(3) . . . . ? C15 C16 C17 O2 -179.4(2) . . . . ? O2 C17 C18 C19 179.2(2) . . . . ? C16 C17 C18 C19 -1.4(3) . . . . ? C15 C14 C19 C18 0.4(3) . . . . ? C10 C14 C19 C18 -177.5(2) . . . . ? C17 C18 C19 C14 0.7(4) . . . . ? C14 C10 O1 C9 -174.94(17) . . . . ? C11 C10 O1 C9 60.2(2) . . . . ? C8 C9 O1 C10 -62.9(2) . . . . ? C18 C17 O2 C20 0.5(3) . . . . ? C16 C17 O2 C20 -178.9(2) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.136 _refine_diff_density_min -0.122 _refine_diff_density_rms 0.027