#------------------------------------------------------------------------------ #$Date: 2025-08-19 07:12:48 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301798 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/10/2011091.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_2011091 loop_ _publ_author_name 'Ruggiero, Silvana Guilardi' 'Gambardella, Maria Teresa do Prado' 'Branco, Marcelo Cardoso' 'Demuner, Antonio Jacinto' 'Barbosa, Luis Claudio A.' 'Pil\'o-Veloso, Dorila' _publ_section_title ; 21\a-Fluoro-7-norvouacapane-17\b,21\a-lactone ; _journal_issue 7 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 868 _journal_page_last 869 _journal_paper_doi 10.1107/S0108270100004790 _journal_volume 56 _journal_year 2000 _chemical_formula_moiety 'C20 H25 F O3' _chemical_formula_sum 'C20 H25 F O3' _chemical_formula_weight 332.40 _chemical_name_systematic ; 21\a-fluoro-7-norvouacapane-17\b,21\a-lactone ; _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' _cell_angle_alpha 90.00 _cell_angle_beta 101.690(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 9.4400(10) _cell_length_b 9.3660(10) _cell_length_c 9.7410(10) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 18.31 _cell_measurement_theta_min 10.31 _cell_volume 843.39(16) _computing_cell_refinement 'CAD-4 Software' _computing_data_collection 'CAD-4 Software (Enraf Nonius, 1989)' _computing_data_reduction 'SDP (Fair, 1990)' _computing_molecular_graphics 'ORTEPIII (Burnett & Johnson, 1996)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1990)' _diffrn_measurement_device_type 'Enraf-Nonius CAD-4' _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 .71073 _diffrn_reflns_av_R_equivalents .031 _diffrn_reflns_av_sigmaI/netI .022 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 1920 _diffrn_reflns_theta_max 26.29 _diffrn_reflns_theta_min 2.74 _diffrn_standards_decay_% 1 _diffrn_standards_interval_time 120 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .094 _exptl_absorpt_correction_T_max .993 _exptl_absorpt_correction_T_min .961 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North et al., 1968)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.309 _exptl_crystal_density_meas ? _exptl_crystal_density_method none _exptl_crystal_description plate _exptl_crystal_F_000 356 _exptl_crystal_size_max .45 _exptl_crystal_size_mid .40 _exptl_crystal_size_min .08 _refine_diff_density_max .14 _refine_diff_density_min -.19 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -.6(12) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.111 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 218 _refine_ls_number_reflns 1813 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.111 _refine_ls_R_factor_all .048 _refine_ls_R_factor_gt .035 _refine_ls_shift/su_max .000 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0491P)^2^+0.1231P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .097 _reflns_number_gt 1571 _reflns_number_total 1813 _reflns_threshold_expression I>2\s(I) _cod_data_source_file da1124.cif _cod_data_source_block III _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w = 1/[\s^2^(Fo^2^)+(0.0491P)^2^+0.1231P] 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^)+(0.0491P)^2^+0.1231P] where P=(Fo^2^+2Fc^2^)/3'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_cell_volume 843.4(2) _cod_original_sg_symbol_H-M 'P 21' _cod_database_code 2011091 _cod_database_fobs_code 2011091 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol F .90740(17) .2733(2) .65624(19) .0620(5) Uani d . 1 . . F O1 .8964(2) -.3908(2) .7621(2) .0574(6) Uani d . 1 . . O O2 .7468(2) .0673(3) .9568(2) .0634(6) Uani d . 1 . . O O3 .8758(2) .2340(2) .8779(2) .0552(5) Uani d . 1 . . O C1 1.3326(3) -.0233(3) .5930(3) .0474(6) Uani d . 1 . . C H11 1.2616 -.0167 .5060 .057 Uiso calc R 1 . . H H12 1.3728 -.1190 .5998 .057 Uiso calc R 1 . . H C2 1.4535(3) .0857(4) .5916(3) .0546(7) Uani d . 1 . . C H21 1.5288 .0725 .6745 .066 Uiso calc R 1 . . H H22 1.4956 .0691 .5101 .066 Uiso calc R 1 . . H C3 1.3974(3) .2385(3) .5882(3) .0523(7) Uani d . 1 . . C H31 1.3318 .2538 .4990 .063 Uiso calc R 1 . . H H32 1.4786 .3028 .5921 .063 Uiso calc R 1 . . H C4 1.3186(3) .2792(3) .7064(3) .0413(6) Uani d . 1 . . C C5 1.2049(3) .1618(3) .7090(2) .0336(5) Uani d . 1 . . C H51 1.1390 .1690 .6175 .040 Uiso calc R 1 . . H C6 1.1046(3) .1656(3) .8168(2) .0350(5) Uani d . 1 . . C H61 1.1649 .1832 .9096 .042 Uiso calc R 1 . . H C8 1.0472(2) .0123(3) .8146(2) .0335(5) Uani d . 1 . . C H81 1.0831 -.0300 .9071 .040 Uiso calc R 1 . . H C9 1.1124(3) -.0711(3) .7075(2) .0357(5) Uani d . 1 . . C H91 1.0538 -.0493 .6148 .043 Uiso calc R 1 . . H C10 1.2590(2) .0040(3) .7170(2) .0355(5) Uani d . 1 . . C C11 1.0972(3) -.2314(3) .7314(3) .0477(6) Uani d . 1 . . C H111 1.1096 -.2847 .6493 .057 Uiso calc R 1 . . H H112 1.1697 -.2630 .8110 .057 Uiso calc R 1 . . H C12 .9489(3) -.2542(3) .7589(3) .0447(6) Uani d . 1 . . C C13 .8498(3) -.1591(3) .7835(3) .0409(6) Uani d . 1 . . C C14 .8819(2) -.0014(3) .7811(3) .0373(5) Uani d . 1 . . C H141 .8466 .0336 .6855 .045 Uiso calc R 1 . . H C15 .7268(3) -.2401(4) .8025(3) .0485(7) Uani d . 1 . . C H151 .6405 -.2044 .8206 .058 Uiso calc R 1 . . H C16 .7606(4) -.3776(4) .7893(3) .0565(8) Uani d . 1 . . C H161 .6998 -.4538 .7976 .068 Uiso calc R 1 . . H C17 .8255(3) .0949(3) .8791(3) .0458(6) Uani d . 1 . . C C18 1.2420(4) .4220(4) .6681(4) .0596(8) Uani d . 1 . . C H181 1.3115 .4925 .6541 .089 Uiso calc R 1 . . H H182 1.1961 .4518 .7427 .089 Uiso calc R 1 . . H H183 1.1703 .4112 .5834 .089 Uiso calc R 1 . . H C19 1.4264(3) .3014(4) .8455(3) .0549(7) Uani d . 1 . . C H191 1.4836 .3850 .8390 .082 Uiso calc R 1 . . H H192 1.4886 .2197 .8646 .082 Uiso calc R 1 . . H H193 1.3745 .3135 .9199 .082 Uiso calc R 1 . . H C20 1.3605(3) -.0374(3) .8550(3) .0483(7) Uani d . 1 . . C H201 1.3228 -.0008 .9325 .072 Uiso calc R 1 . . H H202 1.4548 .0022 .8573 .072 Uiso calc R 1 . . H H203 1.3675 -.1395 .8617 .072 Uiso calc R 1 . . H C21 .9790(3) .2700(3) .7957(3) .0474(6) Uani d . 1 . . C H211 1.0169 .3656 .8226 .057 Uiso calc R 1 . . H 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 F .0583(10) .0536(11) .0704(10) .0184(9) .0041(8) .0180(9) O1 .0713(15) .0360(12) .0676(13) -.0094(10) .0203(11) .0007(9) O2 .0562(12) .0694(16) .0733(14) -.0052(11) .0341(10) -.0162(12) O3 .0521(11) .0424(11) .0768(14) .0061(9) .0265(10) -.0139(10) C1 .0484(14) .0462(16) .0520(15) .0017(13) .0205(11) -.0066(13) C2 .0578(17) .0576(18) .0563(16) -.0043(15) .0302(13) -.0097(15) C3 .0607(17) .0528(18) .0484(15) -.0126(14) .0226(13) -.0025(13) C4 .0485(13) .0370(14) .0410(12) -.0040(12) .0150(10) -.0025(11) C5 .0371(12) .0322(12) .0309(11) .0015(10) .0055(9) -.0008(10) C6 .0386(12) .0327(12) .0334(11) .0039(10) .0063(9) -.0001(10) C8 .0353(11) .0332(12) .0313(10) .0055(10) .0049(9) .0004(9) C9 .0381(12) .0313(13) .0382(12) .0055(10) .0089(10) .0008(10) C10 .0394(12) .0349(13) .0332(11) .0077(11) .0100(9) .0010(10) C11 .0498(14) .0315(14) .0648(16) .0057(12) .0186(12) -.0007(13) C12 .0536(15) .0293(14) .0509(15) -.0039(11) .0102(12) .0011(11) C13 .0419(13) .0413(15) .0383(13) -.0013(11) .0057(10) -.0019(11) C14 .0361(12) .0362(14) .0384(12) .0031(10) .0048(9) .0002(11) C15 .0479(14) .0551(18) .0428(13) -.0101(13) .0098(11) -.0010(13) C16 .0637(19) .056(2) .0518(15) -.0189(15) .0167(14) .0010(14) C17 .0353(12) .0496(17) .0527(14) .0060(12) .0091(11) -.0072(13) C18 .071(2) .0365(16) .074(2) -.0020(15) .0216(16) .0073(15) C19 .0509(15) .061(2) .0534(15) -.0170(15) .0117(12) -.0140(14) C20 .0361(12) .0551(17) .0530(14) .0100(12) .0071(10) .0110(13) C21 .0488(14) .0342(14) .0605(16) .0059(13) .0142(12) -.0015(13) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source F F .0171 .0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 3 2 -4 2 4 -2 6 -2 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 C16 O1 C12 106.1(2) no C17 O3 C21 120.2(2) yes C10 C1 C2 110.6(2) no C3 C2 C1 111.7(2) no C2 C3 C4 115.8(2) no C18 C4 C19 107.0(2) no C18 C4 C3 108.1(2) no C19 C4 C3 111.0(2) no C18 C4 C5 109.4(2) no C19 C4 C5 114.9(2) no C3 C4 C5 106.2(2) no C4 C5 C6 121.2(2) yes C4 C5 C10 117.0(2) yes C6 C5 C10 103.10(19) yes C21 C6 C8 109.7(2) yes C21 C6 C5 119.4(2) yes C8 C6 C5 103.42(19) yes C9 C8 C14 110.21(19) yes C9 C8 C6 107.32(19) yes C14 C8 C6 114.99(19) yes C8 C9 C11 109.5(2) yes C8 C9 C10 101.96(19) yes C11 C9 C10 123.4(2) yes C1 C10 C20 110.3(2) no C1 C10 C9 115.0(2) yes C20 C10 C9 109.3(2) no C1 C10 C5 108.4(2) yes C20 C10 C5 115.0(2) no C9 C10 C5 98.53(18) no C12 C11 C9 106.7(2) no C13 C12 O1 110.2(2) no C13 C12 C11 130.3(3) no O1 C12 C11 119.5(2) no C12 C13 C15 106.4(3) no C12 C13 C14 119.7(2) no C15 C13 C14 133.8(3) no C17 C14 C13 119.0(2) yes C17 C14 C8 107.1(2) yes C13 C14 C8 106.1(2) yes C16 C15 C13 106.4(3) no C15 C16 O1 110.9(3) no O2 C17 O3 117.9(3) yes O2 C17 C14 128.7(3) yes O3 C17 C14 113.3(2) yes F C21 O3 107.6(2) yes F C21 C6 111.0(2) yes O3 C21 C6 112.1(2) yes loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag F C21 . 1.390(3) yes O1 C16 . 1.366(4) no O1 C12 . 1.375(3) no O2 C17 . 1.192(3) yes O3 C17 . 1.387(4) yes O3 C21 . 1.421(3) yes C1 C10 . 1.532(3) no C1 C2 . 1.533(4) no C2 C3 . 1.524(5) no C3 C4 . 1.540(3) no C4 C18 . 1.530(4) no C4 C19 . 1.536(4) no C4 C5 . 1.540(4) no C5 C6 . 1.550(3) yes C5 C10 . 1.560(3) yes C6 C21 . 1.518(3) yes C6 C8 . 1.533(4) yes C8 C9 . 1.528(3) yes C8 C14 . 1.533(3) yes C9 C11 . 1.531(4) yes C9 C10 . 1.539(3) yes C10 C20 . 1.535(3) no C11 C12 . 1.493(4) no C12 C13 . 1.347(4) no C13 C15 . 1.430(4) no C13 C14 . 1.509(4) yes C14 C17 . 1.488(4) yes C15 C16 . 1.338(5) no 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_publ_flag C10 C1 C2 C3 -56.4(3) no C1 C2 C3 C4 55.4(3) no C2 C3 C4 C18 -167.6(3) no C2 C3 C4 C19 75.3(3) no C2 C3 C4 C5 -50.3(3) no C18 C4 C5 C6 -64.3(3) no C19 C4 C5 C6 56.1(3) no C3 C4 C5 C6 179.3(2) no C18 C4 C5 C10 168.3(2) no C19 C4 C5 C10 -71.3(3) no C3 C4 C5 C10 51.9(3) no C4 C5 C6 C21 75.3(3) no C10 C5 C6 C21 -151.3(2) no C4 C5 C6 C8 -162.5(2) no C10 C5 C6 C8 -29.1(2) no C21 C6 C8 C9 127.5(2) no C5 C6 C8 C9 -.9(2) no C21 C6 C8 C14 4.5(3) no C5 C6 C8 C14 -123.85(19) no C14 C8 C9 C11 -71.1(3) no C6 C8 C9 C11 163.0(2) no C14 C8 C9 C10 156.75(19) no C6 C8 C9 C10 30.9(2) no C2 C1 C10 C20 -71.4(3) no C2 C1 C10 C9 164.4(2) no C2 C1 C10 C5 55.3(3) no C8 C9 C10 C1 -162.5(2) no C11 C9 C10 C1 74.3(3) no C8 C9 C10 C20 72.9(2) no C11 C9 C10 C20 -50.4(3) no C8 C9 C10 C5 -47.5(2) no C11 C9 C10 C5 -170.8(2) no C4 C5 C10 C1 -56.6(3) no C6 C5 C10 C1 167.69(19) no C4 C5 C10 C20 67.4(3) no C6 C5 C10 C20 -68.4(2) no C4 C5 C10 C9 -176.55(19) no C6 C5 C10 C9 47.7(2) no C8 C9 C11 C12 42.3(3) no C10 C9 C11 C12 162.1(2) no C16 O1 C12 C13 .1(3) no C16 O1 C12 C11 179.9(3) no C9 C11 C12 C13 -10.6(4) no C9 C11 C12 O1 169.7(2) no O1 C12 C13 C15 -.4(3) no C11 C12 C13 C15 179.9(3) no O1 C12 C13 C14 -178.3(2) no C11 C12 C13 C14 2.0(4) no C12 C13 C14 C17 -145.5(3) no C15 C13 C14 C17 37.2(4) no C12 C13 C14 C8 -24.8(3) no C15 C13 C14 C8 157.9(3) no C9 C8 C14 C17 -173.8(2) no C6 C8 C14 C17 -52.3(3) no C9 C8 C14 C13 58.2(2) no C6 C8 C14 C13 179.6(2) no C12 C13 C15 C16 .5(3) no C14 C13 C15 C16 178.0(3) no C13 C15 C16 O1 -.4(3) no C12 O1 C16 C15 .2(3) no C21 O3 C17 O2 174.9(2) no C21 O3 C17 C14 -4.1(4) no C13 C14 C17 O2 -5.8(4) no C8 C14 C17 O2 -125.9(3) no C13 C14 C17 O3 173.1(2) no C8 C14 C17 O3 53.0(3) no C17 O3 C21 F 74.3(3) no C17 O3 C21 C6 -48.0(3) no C8 C6 C21 F -75.9(3) no C5 C6 C21 F 43.1(3) no C8 C6 C21 O3 44.5(3) no C5 C6 C21 O3 163.5(2) no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 8981796 2 PubChem 10806491