# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2003 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 loop_ _publ_author_name 'Pierre Grandclaudon' 'Elena Bacu' 'A. Couture' 'Guy Nowogrocki' 'Dalila Samson-Belei' _publ_contact_author_name 'Dr Pierre Grandclaudon' _publ_contact_author_address ; Laboratoire de Chimie Organique Physique, associe a l'enscl, UMR 8009 Universitie des Sciences et Technologies de Lille 1, Villeneuve d'Ascq Cedex F-59655 FRANCE ; _publ_contact_author_email PIERRE.GRANDCLAUDON@UNIV-LILLE1.FR _publ_section_title ; Benzoindolizine derivatives of N-acylphenothiazine. Synthesis and characterizaton. ; data_grandbtm=_1a _database_code_CSD 205735 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,2-Di(methoxycarbonyl)-1,10b-dihydropyrolo[2,1-a]isoquinolin-3-yl- (10H-phenothiazin-10-yl)-1-methanone ; _chemical_name_common ; 1,2-Di(methoxycarbonyl)-1,10b-dihydropyrolo(2,1-a)isoquinolin- 3-yl-(10H-phenothiazin-10-yl)-1-methanone ; _chemical_melting_point 186-187C _chemical_formula_moiety ? _chemical_formula_sum 'C29 H22 N2 O5 S' _chemical_formula_weight 510.55 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 37.608(6) _cell_length_b 8.6937(14) _cell_length_c 15.053(3) _cell_angle_alpha 90.00 _cell_angle_beta 99.163(3) _cell_angle_gamma 90.00 _cell_volume 4858.8(14) _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 'irregular prism' _exptl_crystal_colour yellow _exptl_crystal_size_max .45 _exptl_crystal_size_mid .25 _exptl_crystal_size_min .13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.396 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2128 _exptl_absorpt_coefficient_mu 0.178 _exptl_absorpt_correction_type none _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 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14845 _diffrn_reflns_av_R_equivalents 0.0430 _diffrn_reflns_av_sigmaI/netI 0.0415 _diffrn_reflns_limit_h_min -44 _diffrn_reflns_limit_h_max 44 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.11 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4155 _reflns_number_gt 3206 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _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^)+(0.0769P)^2^+0.0000P] 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 4155 _refine_ls_number_parameters 416 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0611 _refine_ls_R_factor_gt 0.0459 _refine_ls_wR_factor_ref 0.1295 _refine_ls_wR_factor_gt 0.1219 _refine_ls_goodness_of_fit_ref 1.121 _refine_ls_restrained_S_all 1.121 _refine_ls_shift/su_max 0.014 _refine_ls_shift/su_mean 0.001 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 0.17163(6) 0.8668(3) 0.80538(14) 0.0216(5) Uani 1 1 d . . . C2 C 0.13174(6) 0.8752(2) 0.76861(15) 0.0223(5) Uani 1 1 d . . . C3 C 0.12573(6) 0.8197(2) 0.68388(15) 0.0220(5) Uani 1 1 d . . . N4 N 0.15678(5) 0.7646(2) 0.65835(12) 0.0217(4) Uani 1 1 d . . . C5 C 0.16257(6) 0.6913(3) 0.58033(16) 0.0248(5) Uani 1 1 d . . . C6 C 0.19615(6) 0.6535(3) 0.56981(16) 0.0255(5) Uani 1 1 d . . . C7 C 0.22720(6) 0.7074(3) 0.63271(14) 0.0225(5) Uani 1 1 d . . . C8 C 0.26210(6) 0.7076(3) 0.61190(17) 0.0263(5) Uani 1 1 d . . . C9 C 0.29015(6) 0.7721(3) 0.67048(16) 0.0277(6) Uani 1 1 d . . . C10 C 0.28428(6) 0.8393(3) 0.75029(17) 0.0270(5) Uani 1 1 d . . . C11 C 0.24960(6) 0.8394(3) 0.77213(16) 0.0241(5) Uani 1 1 d . . . C12 C 0.22139(6) 0.7722(3) 0.71498(15) 0.0224(5) Uani 1 1 d . . . C13 C 0.18450(6) 0.7522(3) 0.73945(14) 0.0222(5) Uani 1 1 d . . . O14 O 0.08099(4) 0.95131(18) 0.58547(11) 0.0297(4) Uani 1 1 d . . . C15 C 0.09142(6) 0.8275(3) 0.61651(15) 0.0222(5) Uani 1 1 d . . . N16 N 0.07444(5) 0.6908(2) 0.59186(12) 0.0209(4) Uani 1 1 d . . . C17 C 0.08828(5) 0.5451(2) 0.62706(14) 0.0206(5) Uani 1 1 d . . . C18 C 0.09569(6) 0.5167(3) 0.71852(15) 0.0229(5) Uani 1 1 d . . . C19 C 0.11109(6) 0.3781(3) 0.74966(16) 0.0252(5) Uani 1 1 d . . . C20 C 0.11790(6) 0.2662(3) 0.68869(16) 0.0265(5) Uani 1 1 d . . . C21 C 0.10883(6) 0.2912(3) 0.59730(16) 0.0239(5) Uani 1 1 d . . . C22 C 0.09418(6) 0.4312(3) 0.56573(15) 0.0218(5) Uani 1 1 d . . . S23 S 0.082843(15) 0.46324(7) 0.44924(4) 0.02543(19) Uani 1 1 d . . . C24 C 0.04530(6) 0.5861(3) 0.44999(15) 0.0236(5) Uani 1 1 d . . . C25 C 0.01684(6) 0.5816(3) 0.37836(16) 0.0278(6) Uani 1 1 d . . . C26 C -0.01177(6) 0.6820(3) 0.37688(17) 0.0303(6) Uani 1 1 d . . . C27 C -0.01295(6) 0.7824(3) 0.44801(17) 0.0288(6) Uani 1 1 d . . . C28 C 0.01497(6) 0.7842(3) 0.52014(17) 0.0253(5) Uani 1 1 d . . . C29 C 0.04430(6) 0.6878(3) 0.52007(15) 0.0225(5) Uani 1 1 d . . . C30 C 0.17865(6) 0.8078(3) 0.90139(16) 0.0270(5) Uani 1 1 d . . . O31 O 0.16712(5) 0.6889(2) 0.92553(11) 0.0401(5) Uani 1 1 d . . . O32 O 0.19984(5) 0.9037(2) 0.95480(11) 0.0361(4) Uani 1 1 d . . . C33 C 0.20722(10) 0.8595(4) 1.04863(19) 0.0495(8) Uani 1 1 d . . . H17 H 0.2147(8) 0.747(4) 1.052(2) 0.059 Uiso 1 1 d . . . H18 H 0.1848(9) 0.860(4) 1.074(2) 0.059 Uiso 1 1 d . . . H19 H 0.2255(9) 0.931(4) 1.073(2) 0.059 Uiso 1 1 d . . . C34 C 0.10748(6) 0.9484(3) 0.82213(16) 0.0278(6) Uani 1 1 d . . . O35 O 0.11751(5) 1.0212(2) 0.88930(12) 0.0413(5) Uani 1 1 d . . . O36 O 0.07239(4) 0.9251(2) 0.78786(11) 0.0342(4) Uani 1 1 d . . . C37 C 0.04767(8) 0.9999(4) 0.8387(2) 0.0463(8) Uani 1 1 d . . . H20 H 0.0238(9) 0.963(3) 0.812(2) 0.056 Uiso 1 1 d . . . H21 H 0.0534(8) 0.969(3) 0.901(2) 0.056 Uiso 1 1 d . . . H22 H 0.0505(8) 1.116(4) 0.8339(19) 0.056 Uiso 1 1 d . . . H1 H 0.1824(6) 0.969(3) 0.8001(14) 0.016(5) Uiso 1 1 d . . . H2 H 0.1425(7) 0.674(3) 0.5358(17) 0.039(7) Uiso 1 1 d . . . H3 H 0.2002(6) 0.601(3) 0.5157(16) 0.025(6) Uiso 1 1 d . . . H4 H 0.2667(7) 0.659(3) 0.5559(18) 0.045(8) Uiso 1 1 d . . . H5 H 0.3138(9) 0.767(3) 0.656(2) 0.059(9) Uiso 1 1 d . . . H6 H 0.3043(7) 0.884(3) 0.7922(17) 0.035(7) Uiso 1 1 d . . . H7 H 0.2460(6) 0.893(3) 0.8260(16) 0.024(6) Uiso 1 1 d . . . H8 H 0.1817(6) 0.646(3) 0.7649(16) 0.033(7) Uiso 1 1 d . . . H9 H 0.0906(6) 0.595(3) 0.7588(15) 0.016(5) Uiso 1 1 d . . . H10 H 0.1169(7) 0.356(3) 0.8164(17) 0.035(7) Uiso 1 1 d . . . H11 H 0.1283(6) 0.170(3) 0.7074(16) 0.030(7) Uiso 1 1 d . . . H12 H 0.1130(6) 0.219(3) 0.5542(17) 0.030(7) Uiso 1 1 d . . . H13 H 0.0171(6) 0.509(3) 0.3322(15) 0.018(6) Uiso 1 1 d . . . H14 H -0.0327(7) 0.674(3) 0.3218(18) 0.041(7) Uiso 1 1 d . . . H15 H -0.0331(6) 0.853(3) 0.4463(14) 0.023(6) Uiso 1 1 d . . . H16 H 0.0132(6) 0.855(3) 0.5676(16) 0.026(6) 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 C1 0.0217(12) 0.0243(13) 0.0198(12) -0.0001(10) 0.0059(9) -0.0007(10) C2 0.0222(12) 0.0209(12) 0.0242(12) 0.0015(9) 0.0052(10) 0.0010(10) C3 0.0190(12) 0.0192(12) 0.0283(13) 0.0029(10) 0.0051(10) -0.0006(9) N4 0.0188(10) 0.0260(10) 0.0202(10) -0.0009(8) 0.0023(8) -0.0018(8) C5 0.0248(13) 0.0283(13) 0.0215(12) -0.0038(10) 0.0043(10) -0.0030(10) C6 0.0261(13) 0.0274(13) 0.0241(13) -0.0043(10) 0.0072(10) -0.0036(10) C7 0.0223(12) 0.0229(12) 0.0223(12) 0.0053(9) 0.0032(10) 0.0012(10) C8 0.0256(13) 0.0271(13) 0.0272(13) 0.0055(11) 0.0070(11) 0.0041(10) C9 0.0190(12) 0.0332(14) 0.0311(14) 0.0102(11) 0.0046(11) 0.0017(10) C10 0.0220(12) 0.0292(13) 0.0281(13) 0.0047(11) -0.0015(11) -0.0021(10) C11 0.0244(12) 0.0245(12) 0.0227(12) 0.0016(10) 0.0015(10) -0.0016(10) C12 0.0216(12) 0.0223(12) 0.0229(12) 0.0058(9) 0.0022(10) 0.0029(9) C13 0.0216(12) 0.0237(12) 0.0212(12) 0.0001(10) 0.0029(10) -0.0018(10) O14 0.0252(9) 0.0243(9) 0.0376(10) 0.0041(7) -0.0006(7) 0.0019(7) C15 0.0190(12) 0.0246(13) 0.0240(12) 0.0008(10) 0.0067(10) -0.0002(10) N16 0.0181(9) 0.0208(10) 0.0228(10) 0.0012(8) 0.0004(8) 0.0008(8) C17 0.0157(11) 0.0219(12) 0.0244(12) 0.0013(9) 0.0041(9) -0.0017(9) C18 0.0181(11) 0.0256(12) 0.0257(12) -0.0014(10) 0.0052(10) -0.0013(10) C19 0.0222(12) 0.0295(13) 0.0226(13) 0.0026(10) -0.0001(10) -0.0018(10) C20 0.0231(12) 0.0250(13) 0.0313(14) 0.0046(11) 0.0034(10) 0.0017(11) C21 0.0189(12) 0.0247(12) 0.0287(13) -0.0025(11) 0.0062(10) -0.0007(10) C22 0.0173(11) 0.0253(12) 0.0232(12) 0.0021(10) 0.0041(9) -0.0015(9) S23 0.0251(3) 0.0302(4) 0.0209(3) 0.0001(2) 0.0033(2) 0.0025(2) C24 0.0201(12) 0.0253(12) 0.0257(12) 0.0057(10) 0.0043(9) -0.0019(10) C25 0.0275(13) 0.0290(13) 0.0257(13) 0.0017(11) 0.0007(10) -0.0058(11) C26 0.0232(13) 0.0346(14) 0.0311(14) 0.0108(11) -0.0022(11) -0.0082(11) C27 0.0195(12) 0.0273(13) 0.0391(15) 0.0096(12) 0.0031(11) -0.0019(11) C28 0.0230(12) 0.0241(13) 0.0291(13) 0.0037(11) 0.0049(10) -0.0002(10) C29 0.0196(11) 0.0234(12) 0.0238(12) 0.0045(10) 0.0017(9) -0.0021(9) C30 0.0243(12) 0.0314(14) 0.0258(13) -0.0019(11) 0.0052(10) -0.0004(11) O31 0.0511(12) 0.0384(11) 0.0305(10) 0.0057(8) 0.0059(9) -0.0122(9) O32 0.0418(10) 0.0429(10) 0.0223(9) 0.0011(8) 0.0014(8) -0.0111(9) C33 0.062(2) 0.063(2) 0.0217(14) 0.0017(14) 0.0023(14) -0.0184(18) C34 0.0233(13) 0.0314(13) 0.0291(13) 0.0045(11) 0.0053(10) 0.0006(10) O35 0.0351(10) 0.0573(12) 0.0320(10) -0.0172(9) 0.0068(8) 0.0024(9) O36 0.0257(9) 0.0429(10) 0.0356(10) -0.0071(8) 0.0099(7) 0.0039(8) C37 0.0289(15) 0.069(2) 0.0426(17) -0.0095(16) 0.0105(14) 0.0114(15) _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 1.516(3) . ? C1 C30 1.517(3) . ? C1 C13 1.538(3) . ? C2 C3 1.349(3) . ? C2 C34 1.456(3) . ? C3 N4 1.372(3) . ? C3 C15 1.511(3) . ? N4 C5 1.384(3) . ? N4 C13 1.478(3) . ? C5 C6 1.338(3) . ? C6 C7 1.459(3) . ? C7 C8 1.397(3) . ? C7 C12 1.409(3) . ? C8 C9 1.382(3) . ? C9 C10 1.385(4) . ? C10 C11 1.395(3) . ? C11 C12 1.384(3) . ? C12 C13 1.501(3) . ? O14 C15 1.213(3) . ? C15 N16 1.372(3) . ? N16 C29 1.436(3) . ? N16 C17 1.438(3) . ? C17 C18 1.383(3) . ? C17 C22 1.396(3) . ? C18 C19 1.385(3) . ? C19 C20 1.389(3) . ? C20 C21 1.381(3) . ? C21 C22 1.388(3) . ? C22 S23 1.760(2) . ? S23 C24 1.772(2) . ? C24 C29 1.381(3) . ? C24 C25 1.394(3) . ? C25 C26 1.383(4) . ? C26 C27 1.387(4) . ? C27 C28 1.385(3) . ? C28 C29 1.386(3) . ? C30 O31 1.199(3) . ? C30 O32 1.332(3) . ? O32 C33 1.447(3) . ? C34 O35 1.202(3) . ? C34 O36 1.353(3) . ? O36 C37 1.449(3) . ? 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 C30 112.10(18) . . ? C2 C1 C13 100.99(17) . . ? C30 C1 C13 111.77(19) . . ? C3 C2 C34 130.9(2) . . ? C3 C2 C1 109.57(19) . . ? C34 C2 C1 119.34(19) . . ? C2 C3 N4 111.59(19) . . ? C2 C3 C15 128.0(2) . . ? N4 C3 C15 120.11(19) . . ? C3 N4 C5 130.87(19) . . ? C3 N4 C13 108.30(17) . . ? C5 N4 C13 118.81(18) . . ? C6 C5 N4 119.5(2) . . ? C5 C6 C7 121.2(2) . . ? C8 C7 C12 118.7(2) . . ? C8 C7 C6 122.6(2) . . ? C12 C7 C6 118.6(2) . . ? C9 C8 C7 120.4(2) . . ? C8 C9 C10 120.9(2) . . ? C9 C10 C11 119.3(2) . . ? C12 C11 C10 120.4(2) . . ? C11 C12 C7 120.3(2) . . ? C11 C12 C13 122.9(2) . . ? C7 C12 C13 116.6(2) . . ? N4 C13 C12 110.29(17) . . ? N4 C13 C1 103.45(17) . . ? C12 C13 C1 118.77(19) . . ? O14 C15 N16 123.8(2) . . ? O14 C15 C3 119.2(2) . . ? N16 C15 C3 116.99(19) . . ? C15 N16 C29 119.79(18) . . ? C15 N16 C17 122.52(18) . . ? C29 N16 C17 117.21(17) . . ? C18 C17 C22 120.2(2) . . ? C18 C17 N16 121.9(2) . . ? C22 C17 N16 117.88(19) . . ? C17 C18 C19 120.0(2) . . ? C18 C19 C20 119.8(2) . . ? C21 C20 C19 120.4(2) . . ? C20 C21 C22 120.0(2) . . ? C21 C22 C17 119.5(2) . . ? C21 C22 S23 119.99(18) . . ? C17 C22 S23 120.53(17) . . ? C22 S23 C24 98.97(10) . . ? C29 C24 C25 119.9(2) . . ? C29 C24 S23 120.62(17) . . ? C25 C24 S23 119.51(19) . . ? C26 C25 C24 119.6(2) . . ? C25 C26 C27 120.3(2) . . ? C28 C27 C26 119.9(2) . . ? C27 C28 C29 119.8(2) . . ? C24 C29 C28 120.4(2) . . ? C24 C29 N16 118.16(19) . . ? C28 C29 N16 121.4(2) . . ? O31 C30 O32 124.6(2) . . ? O31 C30 C1 124.3(2) . . ? O32 C30 C1 111.1(2) . . ? C30 O32 C33 115.2(2) . . ? O35 C34 O36 123.8(2) . . ? O35 C34 C2 123.7(2) . . ? O36 C34 C2 112.5(2) . . ? C34 O36 C37 113.6(2) . . ? _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.972 _refine_diff_density_max 0.449 _refine_diff_density_min -0.303 _refine_diff_density_rms 0.057 data_grandprm=_2c _database_code_CSD 205736 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-ethoxycarbonyl-2,3-dihydropyrolo[2,1-a]isoquinolin-3-yl- (10H-phenothiazin-10-yl)-1-methanone ; _chemical_name_common ; 1-ethoxycarbonyl-2,3-dihydropyrolo(2,1-a)isoquinolin-3-yl- (10H-phenothiazin-10-yl)-1-methanone ; _chemical_melting_point 203-204C _chemical_formula_moiety ? _chemical_formula_sum 'C28 H22 N2 O3 S' _chemical_formula_weight 466.54 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 20.180(4) _cell_length_b 18.259(4) _cell_length_c 14.878(3) _cell_angle_alpha 90.00 _cell_angle_beta 125.498(3) _cell_angle_gamma 90.00 _cell_volume 4463.0(15) _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 'irregular prism' _exptl_crystal_colour yellow _exptl_crystal_size_max .4 _exptl_crystal_size_mid .3 _exptl_crystal_size_min .15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.389 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1952 _exptl_absorpt_coefficient_mu 0.180 _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 13018 _diffrn_reflns_av_R_equivalents 0.0406 _diffrn_reflns_av_sigmaI/netI 0.0417 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.04 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3713 _reflns_number_gt 2757 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0796P)^2^+1.9291P] 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 3713 _refine_ls_number_parameters 390 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0705 _refine_ls_R_factor_gt 0.0501 _refine_ls_wR_factor_ref 0.1394 _refine_ls_wR_factor_gt 0.1291 _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_restrained_S_all 1.089 _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 C1 C 0.32784(16) 0.05531(14) 0.7909(2) 0.0270(6) Uani 1 1 d . . . C2 C 0.30337(18) 0.08436(14) 0.6797(2) 0.0275(6) Uani 1 1 d . . . C3 C 0.30208(16) 0.01522(14) 0.6211(2) 0.0259(6) Uani 1 1 d . . . N4 N 0.35742(13) -0.03309(11) 0.71334(17) 0.0267(5) Uani 1 1 d . . . C5 C 0.38240(17) -0.09878(15) 0.6989(2) 0.0330(6) Uani 1 1 d . . . C6 C 0.42066(18) -0.14730(15) 0.7815(2) 0.0362(7) Uani 1 1 d . . . C7 C 0.43520(16) -0.13005(15) 0.8859(2) 0.0327(6) Uani 1 1 d . . . C8 C 0.47664(18) -0.17955(17) 0.9751(2) 0.0400(7) Uani 1 1 d . . . C9 C 0.49248(18) -0.16211(18) 1.0749(3) 0.0418(8) Uani 1 1 d . . . C10 C 0.46981(18) -0.09499(18) 1.0906(2) 0.0411(8) Uani 1 1 d . . . C11 C 0.42854(17) -0.04507(17) 1.0056(2) 0.0344(7) Uani 1 1 d . . . C12 C 0.40938(16) -0.06235(14) 0.9016(2) 0.0283(6) Uani 1 1 d . . . C13 C 0.36415(15) -0.01197(14) 0.8082(2) 0.0257(6) Uani 1 1 d . . . O14 O 0.20384(11) -0.07498(10) 0.58878(15) 0.0343(5) Uani 1 1 d . . . C15 C 0.21709(16) -0.02030(14) 0.5555(2) 0.0266(6) Uani 1 1 d . . . N16 N 0.15594(13) 0.01583(11) 0.46116(17) 0.0259(5) Uani 1 1 d . . . C17 C 0.07267(16) -0.00277(15) 0.4145(2) 0.0300(6) Uani 1 1 d . . . C18 C 0.04444(18) -0.07378(17) 0.3847(2) 0.0352(7) Uani 1 1 d . . . C19 C -0.0354(2) -0.0894(2) 0.3462(2) 0.0439(8) Uani 1 1 d . . . C20 C -0.0863(2) -0.0343(2) 0.3356(2) 0.0444(8) Uani 1 1 d . . . C21 C -0.05940(18) 0.03684(19) 0.3621(2) 0.0404(8) Uani 1 1 d . . . C22 C 0.02094(17) 0.05307(16) 0.4028(2) 0.0349(7) Uani 1 1 d . . . S23 S 0.05804(5) 0.14271(4) 0.44479(6) 0.0372(2) Uani 1 1 d . . . C24 C 0.12682(16) 0.14426(14) 0.4079(2) 0.0293(6) Uani 1 1 d . . . C25 C 0.13938(18) 0.20784(16) 0.3686(2) 0.0362(7) Uani 1 1 d . . . C26 C 0.19303(18) 0.20823(16) 0.3402(2) 0.0363(7) Uani 1 1 d . . . C27 C 0.23304(17) 0.14494(15) 0.3473(2) 0.0315(6) Uani 1 1 d . . . C28 C 0.22063(17) 0.08074(16) 0.3857(2) 0.0291(6) Uani 1 1 d . . . C29 C 0.16949(15) 0.08055(14) 0.41926(19) 0.0268(6) Uani 1 1 d . . . C30 C 0.31174(17) 0.09812(14) 0.8566(2) 0.0332(6) Uani 1 1 d . . . O31 O 0.31841(13) 0.08113(10) 0.94139(16) 0.0398(5) Uani 1 1 d . . . O32 O 0.28136(14) 0.16481(10) 0.80882(17) 0.0453(6) Uani 1 1 d . . . C33 C 0.2545(3) 0.21256(19) 0.8607(3) 0.0558(10) Uani 1 1 d . . . H18 H 0.219(2) 0.192(2) 0.882(3) 0.067 Uiso 1 1 d . . . H19 H 0.208(2) 0.2473(19) 0.797(3) 0.067 Uiso 1 1 d . . . C34 C 0.3240(3) 0.2524(2) 0.9530(4) 0.0594(10) Uani 1 1 d . . . H20 H 0.348(2) 0.278(2) 0.920(3) 0.071 Uiso 1 1 d . . . H21 H 0.366(2) 0.212(2) 1.019(3) 0.071 Uiso 1 1 d . . . H22 H 0.297(2) 0.291(2) 0.977(3) 0.071 Uiso 1 1 d . . . H1 H 0.2540(18) 0.1059(15) 0.641(2) 0.029(7) Uiso 1 1 d . . . H2 H 0.3437(15) 0.1213(14) 0.687(2) 0.023(6) Uiso 1 1 d . . . H3 H 0.3193(15) 0.0198(13) 0.573(2) 0.023(6) Uiso 1 1 d . . . H4 H 0.3713(17) -0.1076(15) 0.622(2) 0.040(8) Uiso 1 1 d . . . H5 H 0.4430(17) -0.1958(15) 0.775(2) 0.039(8) Uiso 1 1 d . . . H6 H 0.495(2) -0.2262(19) 0.961(3) 0.063(10) Uiso 1 1 d . . . H7 H 0.522(2) -0.1975(18) 1.132(3) 0.056(10) Uiso 1 1 d . . . H8 H 0.4801(18) -0.0786(16) 1.158(3) 0.046(9) Uiso 1 1 d . . . H9 H 0.4164(16) 0.0032(16) 1.023(2) 0.028(7) Uiso 1 1 d . . . H10 H 0.0789(15) -0.1118(14) 0.394(2) 0.021(7) Uiso 1 1 d . . . H11 H -0.0535(16) -0.1377(15) 0.325(2) 0.026(7) Uiso 1 1 d . . . H12 H -0.143(2) -0.0459(18) 0.308(3) 0.065(10) Uiso 1 1 d . . . H13 H -0.0953(18) 0.0757(16) 0.356(2) 0.037(8) Uiso 1 1 d . . . H14 H 0.1127(18) 0.2502(17) 0.363(2) 0.046(9) Uiso 1 1 d . . . H15 H 0.2022(17) 0.2532(16) 0.314(2) 0.043(8) Uiso 1 1 d . . . H16 H 0.2689(18) 0.1447(15) 0.324(2) 0.040(8) Uiso 1 1 d . . . H17 H 0.2469(16) 0.0375(15) 0.393(2) 0.023(7) 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 C1 0.0321(15) 0.0284(14) 0.0239(14) -0.0016(11) 0.0181(12) -0.0043(11) C2 0.0320(16) 0.0270(14) 0.0247(14) 0.0015(11) 0.0172(13) 0.0004(13) C3 0.0302(15) 0.0281(14) 0.0222(13) 0.0025(10) 0.0167(12) 0.0023(11) N4 0.0299(12) 0.0303(12) 0.0232(11) 0.0022(9) 0.0174(10) 0.0027(9) C5 0.0396(17) 0.0334(16) 0.0356(16) 0.0007(12) 0.0273(14) 0.0017(13) C6 0.0404(17) 0.0323(16) 0.0408(17) 0.0058(13) 0.0263(15) 0.0072(13) C7 0.0272(15) 0.0346(16) 0.0339(15) 0.0090(12) 0.0163(13) 0.0019(12) C8 0.0352(17) 0.0404(18) 0.0418(18) 0.0108(14) 0.0209(15) 0.0014(13) C9 0.0316(16) 0.0470(19) 0.0348(17) 0.0161(15) 0.0124(14) -0.0022(14) C10 0.0373(17) 0.054(2) 0.0262(16) 0.0015(14) 0.0153(14) -0.0111(15) C11 0.0284(15) 0.0442(18) 0.0268(15) 0.0027(13) 0.0137(13) -0.0063(13) C12 0.0263(14) 0.0322(15) 0.0265(14) 0.0033(11) 0.0153(12) -0.0052(11) C13 0.0250(14) 0.0293(14) 0.0228(13) -0.0001(11) 0.0139(12) -0.0054(11) O14 0.0379(11) 0.0332(11) 0.0310(10) 0.0042(8) 0.0195(9) -0.0032(8) C15 0.0343(15) 0.0280(14) 0.0241(13) -0.0022(11) 0.0208(12) 0.0005(11) N16 0.0284(12) 0.0291(12) 0.0233(11) 0.0022(9) 0.0167(10) 0.0005(9) C17 0.0318(15) 0.0430(17) 0.0181(13) 0.0016(11) 0.0161(12) -0.0036(12) C18 0.0373(17) 0.0461(18) 0.0236(15) -0.0017(13) 0.0184(14) -0.0057(15) C19 0.051(2) 0.058(2) 0.0239(15) -0.0027(14) 0.0219(15) -0.0188(17) C20 0.0315(17) 0.077(3) 0.0244(15) 0.0085(15) 0.0157(14) -0.0063(16) C21 0.0321(17) 0.065(2) 0.0287(16) 0.0116(15) 0.0201(14) 0.0018(16) C22 0.0363(16) 0.0529(18) 0.0211(14) 0.0075(12) 0.0199(13) 0.0033(13) S23 0.0442(5) 0.0419(4) 0.0382(4) 0.0082(3) 0.0312(4) 0.0098(3) C24 0.0355(15) 0.0337(15) 0.0228(13) 0.0026(11) 0.0192(13) 0.0040(12) C25 0.0457(18) 0.0329(16) 0.0370(16) 0.0075(13) 0.0279(15) 0.0104(14) C26 0.0448(18) 0.0332(16) 0.0388(16) 0.0071(13) 0.0289(15) 0.0015(13) C27 0.0321(15) 0.0378(16) 0.0295(15) 0.0040(12) 0.0207(13) -0.0011(12) C28 0.0308(15) 0.0323(16) 0.0260(14) 0.0006(12) 0.0174(12) 0.0019(12) C29 0.0283(14) 0.0348(15) 0.0174(13) 0.0007(10) 0.0132(11) -0.0019(11) C30 0.0443(17) 0.0284(15) 0.0318(15) 0.0005(12) 0.0248(14) -0.0026(12) O31 0.0636(14) 0.0354(11) 0.0355(11) -0.0005(9) 0.0374(11) -0.0037(10) O32 0.0762(16) 0.0336(11) 0.0443(12) 0.0063(9) 0.0454(12) 0.0145(10) C33 0.093(3) 0.0379(19) 0.052(2) -0.0035(16) 0.051(2) 0.0094(19) C34 0.080(3) 0.047(2) 0.072(3) -0.0031(19) 0.056(2) -0.0016(19) _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 C13 1.376(4) . ? C1 C30 1.428(4) . ? C1 C2 1.521(3) . ? C2 C3 1.526(4) . ? C3 N4 1.459(3) . ? C3 C15 1.540(4) . ? N4 C5 1.365(3) . ? N4 C13 1.391(3) . ? C5 C6 1.337(4) . ? C6 C7 1.439(4) . ? C7 C8 1.410(4) . ? C7 C12 1.412(4) . ? C8 C9 1.362(4) . ? C9 C10 1.375(5) . ? C10 C11 1.379(4) . ? C11 C12 1.396(4) . ? C12 C13 1.462(4) . ? O14 C15 1.211(3) . ? C15 N16 1.385(3) . ? N16 C29 1.435(3) . ? N16 C17 1.438(3) . ? C17 C18 1.382(4) . ? C17 C22 1.396(4) . ? C18 C19 1.390(4) . ? C19 C20 1.381(5) . ? C20 C21 1.374(5) . ? C21 C22 1.394(4) . ? C22 S23 1.757(3) . ? S23 C24 1.764(3) . ? C24 C25 1.388(4) . ? C24 C29 1.398(4) . ? C25 C26 1.372(4) . ? C26 C27 1.378(4) . ? C27 C28 1.390(4) . ? C28 C29 1.383(3) . ? C30 O31 1.228(3) . ? C30 O32 1.363(3) . ? O32 C33 1.461(4) . ? C33 C34 1.464(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 C13 C1 C30 132.0(2) . . ? C13 C1 C2 108.4(2) . . ? C30 C1 C2 119.6(2) . . ? C1 C2 C3 102.7(2) . . ? N4 C3 C2 102.3(2) . . ? N4 C3 C15 107.7(2) . . ? C2 C3 C15 110.7(2) . . ? C5 N4 C13 125.1(2) . . ? C5 N4 C3 122.3(2) . . ? C13 N4 C3 110.9(2) . . ? C6 C5 N4 120.4(3) . . ? C5 C6 C7 119.6(3) . . ? C8 C7 C12 118.7(3) . . ? C8 C7 C6 120.9(3) . . ? C12 C7 C6 120.4(2) . . ? C9 C8 C7 120.8(3) . . ? C8 C9 C10 120.2(3) . . ? C9 C10 C11 121.1(3) . . ? C10 C11 C12 119.9(3) . . ? C11 C12 C7 119.3(2) . . ? C11 C12 C13 122.0(2) . . ? C7 C12 C13 118.7(2) . . ? C1 C13 N4 109.3(2) . . ? C1 C13 C12 135.2(2) . . ? N4 C13 C12 115.4(2) . . ? O14 C15 N16 121.9(2) . . ? O14 C15 C3 121.2(2) . . ? N16 C15 C3 116.8(2) . . ? C15 N16 C29 123.4(2) . . ? C15 N16 C17 118.7(2) . . ? C29 N16 C17 116.7(2) . . ? C18 C17 C22 120.4(3) . . ? C18 C17 N16 121.7(3) . . ? C22 C17 N16 117.9(2) . . ? C17 C18 C19 119.2(3) . . ? C20 C19 C18 120.3(3) . . ? C21 C20 C19 120.8(3) . . ? C20 C21 C22 119.5(3) . . ? C21 C22 C17 119.7(3) . . ? C21 C22 S23 120.0(2) . . ? C17 C22 S23 120.2(2) . . ? C22 S23 C24 98.87(13) . . ? C25 C24 C29 119.8(2) . . ? C25 C24 S23 120.9(2) . . ? C29 C24 S23 119.32(19) . . ? C26 C25 C24 120.3(3) . . ? C25 C26 C27 120.3(3) . . ? C26 C27 C28 120.1(3) . . ? C29 C28 C27 120.1(3) . . ? C28 C29 C24 119.4(2) . . ? C28 C29 N16 122.0(2) . . ? C24 C29 N16 118.6(2) . . ? O31 C30 O32 120.6(2) . . ? O31 C30 C1 129.2(2) . . ? O32 C30 C1 110.1(2) . . ? C30 O32 C33 116.7(2) . . ? O32 C33 C34 110.2(3) . . ? _diffrn_measured_fraction_theta_max 0.946 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.946 _refine_diff_density_max 0.489 _refine_diff_density_min -0.284 _refine_diff_density_rms 0.061