#------------------------------------------------------------------------------ #$Date: 2015-04-02 12:22:18 +0100 (Thu, 02 Apr 2015) $ #$Revision: 134621 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/65/2006578.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2006578 loop_ _publ_author_name 'Zukerman-Schpector, J.' 'Castellano, E.E.' 'Ceschi, Marco Antonio' 'Brocksom, Timothy John' 'Wikaira, Jan L.' _publ_section_title ; Intermediates in the Synthesis of Daphniphyllum Alkaloids. I. A Tetracyclic Oxygen Analogue ; _journal_issue 10 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1482 _journal_page_last 1483 _journal_paper_doi 10.1107/S0108270197005222 _journal_volume 53 _journal_year 1997 _chemical_formula_moiety 'C20 H25 Br1 O4' _chemical_formula_sum 'C20 H25 Br O4' _chemical_formula_weight 409.319 _space_group_IT_number 4 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 1' _audit_creation_method 'manual editing of SHELXL93.CIF' _cell_angle_alpha 90 _cell_angle_beta 94.400(10) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 7.9210(9) _cell_length_b 10.6680(10) _cell_length_c 10.7280(10) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 19.35 _cell_measurement_theta_min 9.54 _cell_volume 903.86(16) _computing_cell_refinement 'CAD-4 Software' _computing_data_collection 'CAD-4 Software (Enraf-Nonius, 1989)' _computing_data_reduction 'MolEN (Fair, 1990)' _computing_molecular_graphics 'ZORTEP (Zsolnai, 1995)' _computing_publication_material SHELXL93 _computing_structure_refinement 'SHELXL93 (Sheldrick, 1993)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1985)' _diffrn_measurement_device 'Enraf-Nonius CAD4' _diffrn_measurement_method \w/-2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.023 _diffrn_reflns_av_sigmaI/netI 0.0609 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 2402 _diffrn_reflns_theta_max 27.97 _diffrn_standards_decay_% 0.8 _diffrn_standards_interval_time 60 _diffrn_standards_number 2 _exptl_absorpt_coefficient_mu 2.296 _exptl_absorpt_correction_T_max 0.661 _exptl_absorpt_correction_T_min 0.584 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details '(PLATON; Spek, 1990)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.5040 _exptl_crystal_density_method 'not measured' _exptl_crystal_description irregular _exptl_crystal_F_000 424.0 _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.393 _refine_diff_density_min -0.775 _refine_ls_abs_structure_details 'Flack (1983)' _refine_ls_abs_structure_Flack 0.00(2) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 1.077 _refine_ls_goodness_of_fit_ref 1.159 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 230 _refine_ls_number_reflns 2288 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.077 _refine_ls_restrained_S_obs 1.159 _refine_ls_R_factor_all 0.092 _refine_ls_R_factor_gt 0.042 _refine_ls_shift/su_max 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0376P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.117 _refine_ls_wR_factor_ref 0.098 _reflns_number_gt 1473 _reflns_number_total 2288 _reflns_threshold_expression 'F^2^ > 2\sF^2^' _[local]_cod_data_source_file fg1310.cif _[local]_cod_data_source_block default _[local]_cod_cif_authors_sg_H-M 'P 21' _[local]_cod_chemical_formula_sum_orig 'C20 H25 Br1 O4' _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. '_exptl_absorpt_correction_type' value 'Gaussian' changed to 'gaussian' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w = 1/[\s^2^(Fo^2^)+(0.0376P)^2^] where P = (Fo^2^+2Fc^2^)/3' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 1/[\s^2^(Fo^2^)+(0.0376P)^2^] where P = (Fo^2^+2Fc^2^)/3'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_database_code 2006578 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Br .0724(5) .0734(5) .0353(3) .0179(5) -.0014(3) -.0159(4) O1 .065(3) .028(2) .034(2) .000(2) -.008(2) -.004(2) O2 .028(2) .037(3) .063(3) .002(2) .009(2) .005(2) O3 .091(4) .060(3) .027(2) .021(3) -.008(2) -.005(2) O4 .053(3) .032(2) .041(2) .000(2) .009(2) -.011(2) C1 .031(3) .026(3) .027(2) .002(2) .001(2) .004(2) C2 .046(3) .033(3) .022(2) .008(3) .002(2) -.003(2) C3 .040(3) .031(3) .033(2) -.002(3) -.018(2) .005(3) C4 .026(3) .033(3) .041(3) -.004(3) -.010(2) .007(3) C5 .024(2) .028(4) .035(2) -.002(2) -.001(2) .001(2) C6 .028(3) .035(3) .036(3) -.008(3) -.005(2) .003(3) C7 .039(3) .025(3) .037(3) -.005(3) .000(3) .003(2) C8 .036(3) .027(3) .027(3) .005(3) .003(2) .000(2) C9 .032(3) .033(3) .025(2) .000(2) -.005(2) -.005(2) C10 .025(3) .025(3) .028(2) -.003(2) -.002(2) .004(2) C11 .027(3) .026(3) .029(2) -.004(2) .000(2) -.004(2) C12 .040(3) .030(3) .038(3) -.012(3) .002(3) -.001(3) C13 .036(4) .044(4) .058(4) -.009(3) .009(3) .013(3) C14 .033(4) .057(4) .040(3) .001(3) .008(3) .007(3) C15 .030(3) .052(4) .058(4) -.005(3) .011(3) .004(3) C16 .030(3) .034(3) .033(3) -.001(3) .003(2) -.006(3) C17 .080(6) .056(5) .051(4) .001(4) .019(4) -.029(4) C18 .037(3) .037(4) .037(3) .006(3) .001(2) .011(3) C19 .080(6) .049(5) .076(5) .006(4) -.015(4) .022(4) C20 .064(5) .072(6) .040(3) .017(4) -.013(3) .011(4) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_group _atom_site_type_symbol Br .21492(9) -.00004(8) .76167(5) .0606(3) Uani d . 1 . Br O1 .0353(6) -.1236(4) 1.0275(4) .0431(11) Uani d . 1 . O O2 .4424(5) -.0346(4) 1.1974(4) .0421(11) Uani d . 1 . O O3 .2500(7) .0770(5) 1.4382(4) .0596(14) Uani d . 1 . O O4 .1255(5) .2422(4) 1.3458(4) .0417(10) Uani d . 1 . O C1 .2663(7) .1210(6) .9943(5) .0280(12) Uani d . 1 . C C2 .1609(8) .0483(5) .9249(5) .0336(14) Uani d . 1 . C C3 -.0022(7) -.0052(7) .9637(4) .0360(13) Uani d . 1 . C H3 -.0795(7) -.0200(7) .8894(4) .043 Uiso calc R 1 . H C4 -.0892(7) .0745(6) 1.0557(5) .0342(13) Uani d . 1 . C H4A -.2110(7) .0634(6) 1.0459(5) .041 Uiso calc R 1 . H H4B -.0628(7) .1626(6) 1.0458(5) .041 Uiso calc R 1 . H C5 -.0150(6) .0244(6) 1.1835(5) .0288(12) Uani d . 1 . C C6 -.0223(7) -.1160(6) 1.1512(5) .0335(13) Uani d . 1 . C H6 -.1403(7) -.1442(6) 1.1486(5) .040 Uiso calc R 1 . H C7 .0837(7) -.1998(6) 1.2363(5) .0339(13) Uani d . 1 . C H7 .0410(7) -.2762(6) 1.2611(5) .041 Uiso calc R 1 . H C8 .2388(7) -.1651(6) 1.2764(5) .0299(12) Uani d . 1 . C C9 .2989(7) -.0446(5) 1.2280(5) .0303(13) Uani d . 1 . C C10 .1753(7) .0682(5) 1.2161(5) .0263(11) Uani d . 1 . C C11 .2356(7) .1688(5) 1.1245(5) .0274(11) Uani d . 1 . C H11 .1456(7) .2318(5) 1.1140(5) .033 Uiso calc R 1 . H C12 .4022(7) .2400(6) 1.1671(5) .0361(14) Uani d . 1 . C H12A .3788(7) .3118(6) 1.2186(5) .043 Uiso calc R 1 . H H12B .4815(7) .1852(6) 1.2139(5) .043 Uiso calc R 1 . H C13 .4718(8) .2816(7) 1.0451(6) .046(2) Uani d . 1 . C H13A .4187(8) .3589(7) 1.0150(6) .055 Uiso calc R 1 . H H13B .5933(8) .2942(7) 1.0561(6) .055 Uiso calc R 1 . H C14 .4287(8) .1753(7) .9554(6) .043(2) Uani d . 1 . C H14A .4143(8) .2060(7) .8701(6) .052 Uiso calc R 1 . H H14B .5177(8) .1126(7) .9608(6) .052 Uiso calc R 1 . H C15 -.1368(8) .0519(7) 1.2864(6) .046(2) Uani d . 1 . C H15A -.154(5) .1407(7) 1.292(3) .069 Uiso calc R 1 . H H15B -.088(3) .021(4) 1.3652(11) .069 Uiso calc R 1 . H H15C -.243(2) .011(4) 1.266(3) .069 Uiso calc R 1 . H C16 .1890(7) .1270(6) 1.3463(5) .0320(13) Uani d . 1 . C C17 .1283(10) .3057(8) 1.4651(7) .062(2) Uani d . 1 . C H17A .094(7) .3912(16) 1.4522(8) .093 Uiso calc R 1 . H H17B .2409(19) .303(5) 1.505(3) .093 Uiso calc R 1 . H H17C .052(6) .265(3) 1.517(2) .093 Uiso calc R 1 . H C18 .3645(8) -.2456(6) 1.3559(5) .0372(14) Uani d . 1 . C H18 .4752(8) -.2356(6) 1.3220(5) .045 Uiso calc R 1 . H C19 .3226(11) -.3836(8) 1.3516(8) .070(2) Uani d . 1 . C H19A .413(3) -.4299(9) 1.395(5) .104 Uiso calc R 1 . H H19B .309(7) -.4110(14) 1.2662(9) .104 Uiso calc R 1 . H H19C .219(4) -.3978(10) 1.391(5) .104 Uiso calc R 1 . H C20 .3830(10) -.2009(8) 1.4914(6) .060(2) Uani d . 1 . C H20A .428(7) -.117(2) 1.4947(8) .090 Uiso calc R 1 . H H20B .458(6) -.256(3) 1.5397(13) .090 Uiso calc R 1 . H H20C .2741(15) -.201(5) 1.5250(18) .090 Uiso calc R 1 . H loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Br Br -0.2901 2.4595 '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' 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C6 O1 C3 108.5(4) yes C16 O4 C17 116.7(5) no C2 C1 C14 125.9(5) yes C2 C1 C11 124.9(5) yes C14 C1 C11 109.1(5) yes C1 C2 C3 125.9(5) yes C1 C2 Br 119.9(4) yes C3 C2 Br 114.2(4) yes O1 C3 C2 108.1(4) no O1 C3 C4 105.6(4) no C2 C3 C4 114.4(5) no C3 C4 C5 102.9(4) no C6 C5 C4 97.6(4) no C6 C5 C15 109.3(5) no C4 C5 C15 110.6(5) no C6 C5 C10 110.7(5) no C4 C5 C10 112.5(4) no C15 C5 C10 114.8(4) no O1 C6 C7 109.1(5) no O1 C6 C5 104.7(5) no C7 C6 C5 115.9(5) no C8 C7 C6 119.9(5) no C7 C8 C9 116.4(5) yes C7 C8 C18 125.1(6) yes C9 C8 C18 118.2(5) yes O2 C9 C8 120.4(5) no O2 C9 C10 120.6(5) no C8 C9 C10 119.1(5) no C16 C10 C9 104.1(4) no C16 C10 C11 106.9(5) no C9 C10 C11 111.4(4) no C16 C10 C5 108.7(4) no C9 C10 C5 111.8(5) no C11 C10 C5 113.3(4) no C1 C11 C10 115.3(5) no C1 C11 C12 103.9(4) no C10 C11 C12 116.4(4) no C13 C12 C11 104.1(5) no C14 C13 C12 104.5(6) no C1 C14 C13 105.7(5) no O3 C16 O4 123.3(5) no O3 C16 C10 124.7(6) no O4 C16 C10 112.1(5) no C19 C18 C8 113.5(6) no C19 C18 C20 109.8(6) no C8 C18 C20 111.6(5) no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Br C2 1.906(5) yes O1 C6 1.439(7) yes O1 C3 1.457(8) yes O2 C9 1.212(7) yes O3 C16 1.190(7) no O4 C16 1.327(8) no O4 C17 1.446(8) no C1 C2 1.325(8) yes C1 C14 1.499(8) yes C1 C11 1.523(7) yes C2 C3 1.500(8) yes C3 C4 1.508(9) no C4 C5 1.545(7) no C5 C6 1.538(9) no C5 C15 1.549(8) no C5 C10 1.591(7) no C6 C7 1.489(8) no C7 C8 1.323(8) yes C8 C9 1.479(8) yes C8 C18 1.524(8) yes C9 C10 1.551(8) no C10 C16 1.528(8) no C10 C11 1.555(8) no C11 C12 1.561(7) no C12 C13 1.525(9) no C13 C14 1.509(10) no C18 C19 1.510(10) no C18 C20 1.526(9) no