# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2001 data_global # *** Added by check_cif _database_code_CSD 170402 _audit_creation_method 'maXus + CRYSTALS_ver_12-03-99' _journal_coden_Cambridge 440 _publ_requested_journal 'New Journal of Chemistry' loop_ _publ_author_name 'Banwell, M.' 'Bray, Andrew W.' 'Edwards, Alison J.' 'Wong, David J.' _publ_contact_author_name 'Prof M Banwell' _publ_contact_author_address ; The Research School of Chemistry Australian National University Canberra ACT 0200 AUSTRALIA ; _publ_contact_author_email 'MGB@RSC.ANU.EDU.AU' _publ_section_title ; Total synthesis of the putative structure of the marine alkaloid haliclorensin ; _publ_section_abstract ; We present the crystal and molecular structure of ; _publ_section_comment ; The study of the titled structure was undertaken to establish its three dimensional structure. Geometries are tabulated below. ; _publ_section_synopsis ; ; _publ_section_exptl_prep ; ; _publ_section_exptl_refinement ; ; _publ_section_figure_captions ; ; _publ_section_acknowledgements ; ; _chemical_compound_source 'Local laboratory' _exptl_crystal_description 'hexagonal plate' _exptl_crystal_colour 'Colourless' _cell_measurement_temperature 200 _refine_ls_hydrogen_treatment 'noref' # Submission details _publ_requested_journal 'Acta Crystallographica Section C ' _diffrn_measurement_device 'KappaCCD' _computing_data_collection 'KappaCCD' _computing_data_reduction 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 loop_ _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_wavelength_id all _diffrn_orient_matrix_type 'X=UH' _diffrn_orient_matrix_UB_11 -0.08279 _diffrn_orient_matrix_UB_12 -0.01265 _diffrn_orient_matrix_UB_13 0.08308 _diffrn_orient_matrix_UB_21 0.00638 _diffrn_orient_matrix_UB_22 0.06116 _diffrn_orient_matrix_UB_23 0.01567 _diffrn_orient_matrix_UB_31 -0.07475 _diffrn_orient_matrix_UB_32 0.01932 _diffrn_orient_matrix_UB_33 -0.04497 _cell_formula_units_Z 4 _exptl_crystal_density_diffrn 1.127 _exptl_crystal_density_method 'not measured' _exptl_special_details ; ? ; _chemical_formula_weight 259.393 _diffrn_radiation_type ' MoK\a' loop_ _symmetry_equiv_pos_as_xyz '+X,+Y,+Z' '-X,-Y,-Z' '-X+ 1/2,+Y+ 1/2,-Z' '+X+ 1/2,-Y+ 1/2,+Z' _symmetry_space_group_name_H-M 'P 21/a ' _symmetry_cell_setting 'Monoclinic' _chemical_formula_moiety 'C17 H25 N O ' _chemical_formula_sum 'C17 H25 N O ' _chemical_name_systematic ; ? ; _cell_length_a 8.6690(2) _cell_length_b 15.7588(3) _cell_length_c 11.4462(2) _cell_angle_alpha 90.00 _cell_angle_beta 102.0894(11) _cell_angle_gamma 90.00 _cell_volume 1529.02(5) _diffrn_reflns_number 26911 _diffrn_reflns_theta_max 27.51 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_full 27.51 _cell_measurement_reflns_used 14996 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 27.485 _diffrn_measurement_method 'CCD' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' # Absorption correction loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 0 1 0.005 0 0 -1 0.012 0 -1 0 0.150 0 1 0 0.140 -1 -2 0 0.190 1 4 0 0.120 1 -1 0 0.180 -1 1 0 0.240 _exptl_absorpt_correction_type 'integration' _exptl_absorpt_correction_T_min 0.975 _exptl_absorpt_correction_T_max 0.999 _exptl_absorpt_process_details ; Gaussian integration (Coppens, 1970) ; _diffrn_reflns_av_R_equivalents 0.072 _exptl_absorpt_coefficient_mu 0.069 _exptl_crystal_F_000 568 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0020 0.0020 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International_Tables_Vol_IV_Table_2.2B' 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7997 0.0030 'International_Tables_Vol_IV_Table_2.2B' 'N ' 0.0040 0.0030 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International_Tables_Vol_IV_Table_2.2B' 'O ' 0.0080 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International_Tables_Vol_IV_Table_2.2B' # Refinement statistics _reflns_d_resolution_low 1.85 _reflns_d_resolution_high 0.62 _reflns_limit_h_min -11 _reflns_limit_h_max 11 _reflns_limit_k_min 0 _reflns_limit_k_max 20 _reflns_limit_l_min 0 _reflns_limit_l_max 14 _reflns_number_total 3513 _reflns_number_gt 1892 _refine_diff_density_min -0.14 _refine_diff_density_max 0.14 _reflns_threshold_expression >3.00\s(I) _refine_ls_number_reflns 1892 _refine_ls_number_parameters 173 _refine_ls_R_factor_gt 0.0372 _refine_ls_wR_factor_ref 0.0395 _refine_ls_goodness_of_fit_ref 1.0364 _refine_ls_shift/su_max 0.000273 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Chebychev polynomial with 4 parameters, Carruthers & Watkin , 1979, 0.416 -.123 0.102 -.184 ; _refine_ls_extinction_coef 431.8(313) _refine_ls_extinction_method 'Larson 1970 Crystallographic Computing eq 22' _atom_sites_solution_primary direct _atom_sites_solution_hydrogens geom _computing_structure_solution 'SIR92 (Giacovazzo et al, 1992)' _computing_structure_refinement ; CRYSTALS Issue 10 (Watkin, Prout, Carruthers & Betteridge, 1996) ; _computing_publication_material ; CRYSTALS Issue 10 (Watkin, Prout, Carruthers & Betteridge, 1996) maXus(Mackay et al., 1999) ; _computing_molecular_graphics ; CAMERON (Watkin, Prout & Pearce, 1996) ; _publ_section_references ; Mackay, S., Gilmore, C. J.,Edwards, C., Stewart, N. & Shankland, K. (1999). maXus Computer Program for the Solution and Refinement of Crystal Structures. Nonius, The Netherlands, MacScience, Japan & The University of Glasgow. Johnson, C. K. (1976). ORTEP-II. A Fortran Thermal-Ellipsoid Plot Program. Report ORNL-5138. Oak Ridge National Laboratory, Oak Ridge, Tennessee, USA. Otwinowski, Z. and Minor, W, (1997). In Methods in Enzymology, 276, edited by C.W. Carter, Jr. & R.M. Sweet pp. 307-326, New York:Academic Press. Altomare, A., Cascarano, G., Giacovazzo G., Guagliardi A., Burla M.C., Polidori, G. & Camalli, M. (1994) SIR92 - a program for automatic solution of crystal structures by direct methods. J. Appl. Cryst. (27), 435-435 Carruthers, J.R. and Watkin, D.J. (1979), Acta Cryst, A35, 698-699 Larson, A.C. (1970), Crystallographic Computing, Ed Ahmed, F.R., Munksgaard, Copenhagen, 291-294 Watkin, D.J., Prout, C.K. Carruthers, J.R. & Betteridge, P.W. (1996) CRYSTALS Issue 10. Chemical Crystallography Laboratory, OXFORD, UK. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996) CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. Coppens, P. (1970). In Crystallographic Computing, edited by F.R. Ahmed, S.R.Hall & C.P.Huber, pp 255-270. Copenhagen: Munksgaard. ; loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type O1 0.56688(13) 0.37972(7) 0.4813(1) 0.0497 1.0000 Uani N1 0.82270(14) 0.36671(7) 0.4699(1) 0.0373 1.0000 Uani C2 0.68173(17) 0.40768(9) 0.44589(12) 0.0393 1.0000 Uani C3 0.66354(18) 0.4907(1) 0.37694(14) 0.0436 1.0000 Uani C4 0.52485(19) 0.48889(11) 0.26926(16) 0.0512 1.0000 Uani C5 0.5219(2) 0.41738(12) 0.17917(15) 0.0543 1.0000 Uani C6 0.6403(2) 0.42241(13) 0.09698(15) 0.0605 1.0000 Uani C7 0.8146(2) 0.41430(11) 0.15496(14) 0.0483 1.0000 Uani C8 0.8584(2) 0.3306(1) 0.22149(13) 0.0453 1.0000 Uani C9 0.99962(17) 0.3347(1) 0.32655(13) 0.0401 1.0000 Uani C10 0.96618(16) 0.38952(9) 0.42935(13) 0.0380 1.0000 Uani C11 0.83787(19) 0.29013(9) 0.54517(13) 0.0413 1.0000 Uani C21 0.92196(17) 0.3080(1) 0.67250(12) 0.0403 1.0000 Uani C31 1.0381(2) 0.25379(12) 0.73077(15) 0.0567 1.0000 Uani C41 1.1153(3) 0.26988(16) 0.84799(17) 0.0752 1.0000 Uani C51 1.0742(3) 0.33958(15) 0.90715(16) 0.0717 1.0000 Uani C61 0.9579(3) 0.39339(12) 0.85050(16) 0.0618 1.0000 Uani C71 0.8822(2) 0.3784(1) 0.73330(14) 0.0500 1.0000 Uani C91 1.1484(2) 0.36819(11) 0.29078(16) 0.0524 1.0000 Uani H31 0.64632(18) 0.5375(1) 0.43176(14) 0.0511 1.0000 Uiso H32 0.76252(18) 0.5018(1) 0.34761(14) 0.0511 1.0000 Uiso H41 0.52473(19) 0.54388(11) 0.22563(16) 0.0593 1.0000 Uiso H42 0.42613(19) 0.48426(11) 0.30100(16) 0.0593 1.0000 Uiso H51 0.5422(2) 0.36304(12) 0.22492(15) 0.0608 1.0000 Uiso H52 0.4138(2) 0.41599(12) 0.12712(15) 0.0608 1.0000 Uiso H61 0.6252(2) 0.47856(13) 0.05545(15) 0.0693 1.0000 Uiso H62 0.6140(2) 0.37585(13) 0.03673(15) 0.0693 1.0000 Uiso H71 0.8434(2) 0.46189(11) 0.21324(14) 0.0559 1.0000 Uiso H72 0.8770(2) 0.41914(11) 0.09100(14) 0.0559 1.0000 Uiso H81 0.8828(2) 0.2882(1) 0.16293(13) 0.0526 1.0000 Uiso H82 0.7649(2) 0.3110(1) 0.25264(13) 0.0526 1.0000 Uiso H91 1.01791(17) 0.2746(1) 0.35401(13) 0.0473 1.0000 Uiso H101 1.05751(16) 0.38383(9) 0.49858(13) 0.0437 1.0000 Uiso H102 0.95662(16) 0.44992(9) 0.40202(13) 0.0437 1.0000 Uiso H111 0.89869(19) 0.24633(9) 0.51047(13) 0.0477 1.0000 Uiso H112 0.73001(19) 0.26793(9) 0.54586(13) 0.0477 1.0000 Uiso H311 1.0671(2) 0.20271(12) 0.68816(15) 0.0667 1.0000 Uiso H411 1.2002(3) 0.23072(16) 0.88921(17) 0.0870 1.0000 Uiso H511 1.1290(3) 0.35114(15) 0.99154(16) 0.0822 1.0000 Uiso H611 0.9276(3) 0.44364(12) 0.89413(16) 0.0723 1.0000 Uiso H711 0.7987(2) 0.4184(1) 0.69218(14) 0.0580 1.0000 Uiso H911 1.2369(2) 0.36952(11) 0.36257(16) 0.0637 1.0000 Uiso H912 1.1285(2) 0.42684(11) 0.25769(16) 0.0637 1.0000 Uiso H913 1.1772(2) 0.33018(11) 0.22872(16) 0.0637 1.0000 Uiso 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 0.0459(6) 0.0540(7) 0.0537(7) 0.0040(5) 0.0208(5) 0.0021(5) N1 0.0414(7) 0.0367(7) 0.0350(6) -0.0001(5) 0.0111(5) 0.0017(5) C2 0.0410(8) 0.0430(8) 0.0350(7) -0.0062(6) 0.0108(6) 0.0002(7) C3 0.0442(8) 0.0383(8) 0.0504(9) -0.0027(7) 0.0146(7) 0.0045(6) C4 0.0430(8) 0.0504(9) 0.060(1) 0.0092(8) 0.0101(7) 0.0078(7) C5 0.0438(9) 0.0646(11) 0.0500(9) 0.0073(8) -0.0007(7) -0.0011(8) C6 0.0637(11) 0.0752(13) 0.0396(8) 0.0063(8) 0.0042(8) 0.0067(9) C7 0.0561(9) 0.0541(9) 0.0369(7) 0.0080(7) 0.0148(7) 0.0055(8) C8 0.058(1) 0.0415(8) 0.0379(8) -0.0025(6) 0.0124(7) 0.0028(7) C9 0.0459(8) 0.0365(7) 0.0405(8) 0.0031(6) 0.0149(6) 0.0062(6) C10 0.0366(7) 0.0393(8) 0.0383(7) -0.0001(6) 0.0078(6) 0.0009(6) C11 0.0481(8) 0.0378(8) 0.0391(8) 0.0011(6) 0.0119(6) -0.0007(6) C21 0.0443(8) 0.0418(8) 0.0374(7) 0.0037(7) 0.0148(6) -0.0010(7) C31 0.063(1) 0.0652(11) 0.0445(9) 0.0084(8) 0.0165(8) 0.0145(9) C41 0.0761(14) 0.1011(17) 0.046(1) 0.0175(11) 0.0073(9) 0.0209(12) C51 0.0835(14) 0.0921(15) 0.0362(9) 0.001(1) 0.0048(9) -0.0093(12) C61 0.0895(14) 0.0568(11) 0.0398(8) -0.0024(8) 0.0154(9) -0.009(1) C71 0.0666(11) 0.0436(8) 0.0404(8) 0.0005(7) 0.0129(7) 0.0016(8) C91 0.0496(9) 0.0541(9) 0.059(1) 0.0119(8) 0.0229(8) 0.0120(8) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 . C2 . 1.2324(17) yes N1 . C2 . 1.3584(19) yes N1 . C10 . 1.4609(18) yes N1 . C11 . 1.4723(18) yes C2 . C3 . 1.519(2) yes C3 . C4 . 1.531(2) yes C3 . H31 . 1.000 no C3 . H32 . 1.000 no C4 . C5 . 1.524(3) yes C4 . H41 . 1.000 no C4 . H42 . 1.000 no C5 . C6 . 1.533(2) yes C5 . H51 . 1.000 no C5 . H52 . 1.000 no C6 . C7 . 1.523(2) yes C6 . H61 . 1.000 no C6 . H62 . 1.000 no C7 . C8 . 1.531(2) yes C7 . H71 . 1.000 no C7 . H72 . 1.000 no C8 . C9 . 1.527(2) yes C8 . H81 . 1.000 no C8 . H82 . 1.000 no C9 . C10 . 1.5354(19) yes C9 . C91 . 1.527(2) yes C9 . H91 . 1.000 no C10 . H101 . 1.000 no C10 . H102 . 1.000 no C11 . C21 . 1.513(2) yes C11 . H111 . 1.000 no C11 . H112 . 1.000 no C21 . C31 . 1.381(2) yes C21 . C71 . 1.390(2) yes C31 . C41 . 1.391(3) yes C31 . H311 . 1.000 no C41 . C51 . 1.376(3) yes C41 . H411 . 1.000 no C51 . C61 . 1.372(3) yes C51 . H511 . 1.000 no C61 . C71 . 1.385(2) yes C61 . H611 . 1.000 no C71 . H711 . 1.000 no C91 . H911 . 1.000 no C91 . H912 . 1.000 no C91 . H913 . 1.000 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . N1 . C10 . 127.47(12) yes C2 . N1 . C11 . 118.33(12) yes C10 . N1 . C11 . 114.20(12) yes O1 . C2 . N1 . 121.19(14) yes O1 . C2 . C3 . 118.41(13) yes N1 . C2 . C3 . 120.38(12) yes C2 . C3 . C4 . 112.38(13) yes C2 . C3 . H31 . 108.82(7) no C4 . C3 . H31 . 108.88(8) no C2 . C3 . H32 . 108.76(8) no C4 . C3 . H32 . 108.49(9) no H31 . C3 . H32 . 109.467 no C3 . C4 . C5 . 117.23(13) yes C3 . C4 . H41 . 107.72(9) no C5 . C4 . H41 . 107.75(9) no C3 . C4 . H42 . 107.23(9) no C5 . C4 . H42 . 107.29(9) no H41 . C4 . H42 . 109.467 no C4 . C5 . C6 . 117.28(15) yes C4 . C5 . H51 . 107.63(9) no C6 . C5 . H51 . 107.4(1) no C4 . C5 . H52 . 107.48(9) no C6 . C5 . H52 . 107.46(9) no H51 . C5 . H52 . 109.467 no C5 . C6 . C7 . 117.33(14) yes C5 . C6 . H61 . 107.4(1) no C7 . C6 . H61 . 107.5(1) no C5 . C6 . H62 . 107.5(1) no C7 . C6 . H62 . 107.5(1) no H61 . C6 . H62 . 109.467 no C6 . C7 . C8 . 114.14(15) yes C6 . C7 . H71 . 108.3(1) no C8 . C7 . H71 . 108.26(9) no C6 . C7 . H72 . 108.29(9) no C8 . C7 . H72 . 108.32(8) no H71 . C7 . H72 . 109.467 no C7 . C8 . C9 . 115.42(13) yes C7 . C8 . H81 . 107.93(8) no C9 . C8 . H81 . 108.01(8) no C7 . C8 . H82 . 107.97(9) no C9 . C8 . H82 . 107.95(8) no H81 . C8 . H82 . 109.467 no C8 . C9 . C10 . 112.24(12) yes C8 . C9 . C91 . 112.73(13) yes C10 . C9 . C91 . 108.47(13) yes C8 . C9 . H91 . 104.79(8) no C10 . C9 . H91 . 109.57(8) no C91 . C9 . H91 . 108.93(8) no N1 . C10 . C9 . 114.53(12) yes N1 . C10 . H101 . 108.15(8) no C9 . C10 . H101 . 108.16(8) no N1 . C10 . H102 . 108.26(7) no C9 . C10 . H102 . 108.21(8) no H101 . C10 . H102 . 109.467 no N1 . C11 . C21 . 112.13(12) yes N1 . C11 . H111 . 108.87(7) no C21 . C11 . H111 . 108.87(8) no N1 . C11 . H112 . 108.80(8) no C21 . C11 . H112 . 108.68(8) no H111 . C11 . H112 . 109.467 no C11 . C21 . C31 . 120.35(14) yes C11 . C21 . C71 . 120.71(14) yes C31 . C21 . C71 . 118.94(15) yes C21 . C31 . C41 . 120.50(17) yes C21 . C31 . H311 . 119.6(1) no C41 . C31 . H311 . 119.87(12) no C31 . C41 . C51 . 119.89(19) yes C31 . C41 . H411 . 120.02(12) no C51 . C41 . H411 . 120.09(12) no C41 . C51 . C61 . 120.08(17) yes C41 . C51 . H511 . 120.07(12) no C61 . C51 . H511 . 119.85(12) no C51 . C61 . C71 . 120.30(18) yes C51 . C61 . H611 . 119.80(12) no C71 . C61 . H611 . 119.89(11) no C21 . C71 . C61 . 120.28(16) yes C21 . C71 . H711 . 119.87(9) no C61 . C71 . H711 . 119.85(11) no C9 . C91 . H911 . 109.43(9) no C9 . C91 . H912 . 109.44(8) no H911 . C91 . H912 . 109.476 no C9 . C91 . H913 . 109.54(9) no H911 . C91 . H913 . 109.476 no H912 . C91 . H913 . 109.476 no