#------------------------------------------------------------------------------ #$Date: 2025-08-19 07:12:48 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301798 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/13/2011357.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_2011357 loop_ _publ_author_name 'Meyers, Cal Y.' 'Lutfi, Hisham G.' 'Robinson, Paul D.' _publ_section_title ; sp-9-Acetylfluorene, the initial acetylation product of 9-fluorenyllithium ; _journal_issue 9 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first e418 _journal_page_last e419 _journal_paper_doi 10.1107/S0108270100011124 _journal_volume 56 _journal_year 2000 _chemical_formula_moiety 'C15 H12 O' _chemical_formula_sum 'C15 H12 O' _chemical_formula_weight 208.25 _chemical_melting_point 347.5(5) _chemical_name_systematic ; sp-9-Acetylfluorene ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _cell_angle_alpha 90.00 _cell_angle_beta 98.19(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 11.253(4) _cell_length_b 5.740(6) _cell_length_c 17.782(6) _cell_measurement_reflns_used 23 _cell_measurement_temperature 296 _cell_measurement_theta_max 8.1 _cell_measurement_theta_min 2.3 _cell_volume 1136.9(13) _computing_cell_refinement 'MSC/AFC Diffractometer Control Software' _computing_data_collection ; MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1996) ; _computing_data_reduction ; PROCESS in TEXSAN (Molecular Structure Corporation, 1997) ; _computing_publication_material ; TEXSAN, SHELXL97, and PLATON (Spek, 2000) ; _computing_structure_refinement 'LS in TEXSAN and SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 296 _diffrn_measured_fraction_theta_full .982 _diffrn_measured_fraction_theta_max .982 _diffrn_measurement_device_type 'Rigaku AFC-5S' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71069 _diffrn_reflns_av_R_equivalents .043 _diffrn_reflns_av_sigmaI/netI .058 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 2109 _diffrn_reflns_theta_full 25.16 _diffrn_reflns_theta_max 25.16 _diffrn_reflns_theta_min 2.02 _diffrn_standards_decay_% -.3 _diffrn_standards_interval_count 100 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .075 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.217 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 440 _exptl_crystal_size_max .49 _exptl_crystal_size_mid .43 _exptl_crystal_size_min .38 _refine_diff_density_max .16 _refine_diff_density_min -.20 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 146 _refine_ls_number_reflns 2001 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.008 _refine_ls_R_factor_all .134 _refine_ls_R_factor_gt .045 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0747P)^2^+0.0629P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .156 _reflns_number_gt 981 _reflns_number_total 2001 _reflns_threshold_expression I>2\s(I) _cod_data_source_file qa0375.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '347-348' was changed to '347.5(5)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_chemical_melting_point' value '347-348' was changed to '347.5(5)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2011357 _cod_database_fobs_code 2011357 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' 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 O1 -.0753(2) .5733(4) .41839(14) .0854(8) Uani d . 1 . . O C1 .2326(2) .2426(5) .43818(16) .0592(7) Uani d . 1 . . C C2 .3244(2) .0839(6) .45510(18) .0666(9) Uani d . 1 . . C C3 .3341(2) -.1050(6) .40848(19) .0707(9) Uani d . 1 . . C C4 .2529(2) -.1404(5) .34437(18) .0616(8) Uani d . 1 . . C C4a .1596(2) .0179(5) .32713(15) .0484(7) Uani d . 1 . . C C4b .0617(2) .0272(5) .26332(15) .0516(7) Uani d . 1 . . C C5 .0321(3) -.1187(6) .20109(17) .0695(9) Uani d . 1 . . C C6 -.0669(3) -.0666(7) .14903(19) .0833(11) Uani d . 1 . . C C7 -.1356(3) .1277(7) .1581(2) .0848(11) Uani d . 1 . . C C8 -.1075(3) .2762(6) .21952(18) .0714(9) Uani d . 1 . . C C8a -.0075(2) .2243(5) .27152(15) .0520(7) Uani d . 1 . . C C9 .0418(2) .3560(5) .34278(15) .0529(7) Uani d . 1 . . C C9a .1500(2) .2089(4) .37388(15) .0471(7) Uani d . 1 . . C C10 -.0491(2) .3829(5) .39785(16) .0549(7) Uani d . 1 . . C C11 -.1065(3) .1687(5) .4228(2) .0787(10) Uani d . 1 . . C H1 .2263 .3703 .4696 .071 Uiso calc R 1 . . H H2 .3804 .1045 .4984 .080 Uiso calc R 1 . . H H3 .3968 -.2101 .4207 .085 Uiso calc R 1 . . H H4 .2601 -.2679 .3131 .074 Uiso calc R 1 . . H H5 .0785 -.2495 .1947 .083 Uiso calc R 1 . . H H6 -.0876 -.1634 .1073 .100 Uiso calc R 1 . . H H7 -.2022 .1596 .1223 .102 Uiso calc R 1 . . H H8 -.1543 .4065 .2256 .086 Uiso calc R 1 . . H H9 .0690 .5104 .3289 .063 Uiso calc R 1 . . H H11a -.1145 .1819 .4757 .118 Uiso calc R 1 . . H H11b -.0576 .0360 .4154 .118 Uiso calc R 1 . . H H11c -.1844 .1499 .3936 .118 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 O1 .0847(16) .0616(15) .111(2) .0168(12) .0192(13) -.0204(13) C1 .0522(15) .0620(18) .0636(18) -.0020(14) .0089(14) -.0074(16) C2 .0440(15) .084(2) .069(2) .0035(16) .0007(14) .0016(19) C3 .0448(16) .077(2) .092(2) .0120(16) .0142(17) .007(2) C4 .0510(15) .0536(17) .085(2) .0035(15) .0253(15) -.0064(17) C4a .0401(13) .0483(15) .0591(15) -.0063(12) .0157(12) -.0017(14) C4b .0483(15) .0531(16) .0555(17) -.0133(13) .0148(13) -.0047(14) C5 .0676(19) .075(2) .068(2) -.0221(17) .0188(16) -.0143(18) C6 .080(2) .105(3) .064(2) -.035(2) .0062(19) -.013(2) C7 .061(2) .119(3) .069(2) -.025(2) -.0055(17) .013(2) C8 .0575(18) .081(2) .073(2) -.0030(17) .0011(16) .0119(19) C8a .0464(14) .0549(17) .0545(16) -.0099(13) .0063(13) .0052(14) C9 .0494(15) .0388(14) .0703(18) .0005(12) .0080(13) .0036(14) C9a .0398(14) .0455(15) .0569(16) -.0016(11) .0096(12) .0016(13) C10 .0454(14) .0515(17) .0647(18) .0086(14) -.0022(13) -.0056(15) C11 .068(2) .073(2) .101(3) .0048(18) .0351(18) .008(2) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 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' O O .0106 .0060 '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 -1 0 -1 -1 1 1 -2 0 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 C2 C1 C9a 118.9(3) no C1 C2 C3 120.6(3) no C4 C3 C2 121.1(3) no C3 C4 C4a 118.7(3) no C4 C4a C9a 120.4(3) no C4 C4a C4b 131.0(3) no C9a C4a C4b 108.7(2) no C5 C4b C8a 119.9(3) no C5 C4b C4a 131.5(3) no C8a C4b C4a 108.6(2) no C6 C5 C4b 118.9(3) no C5 C6 C7 120.7(3) no C6 C7 C8 121.4(3) no C8a C8 C7 117.8(3) no C8 C8a C4b 121.3(3) no C8 C8a C9 128.3(3) no C4b C8a C9 110.5(2) no C8a C9 C9a 101.9(2) no C8a C9 C10 113.0(2) no C9a C9 C10 113.5(2) no C1 C9a C4a 120.4(2) no C1 C9a C9 129.3(3) no C4a C9a C9 110.4(2) no O1 C10 C11 121.7(3) no O1 C10 C9 120.3(3) no C11 C10 C9 118.0(2) no C2 C1 H1 120.5 no C9a C1 H1 120.5 no C1 C2 H2 119.7 no C3 C2 H2 119.7 no C4 C3 H3 119.5 no C2 C3 H3 119.5 no C3 C4 H4 120.7 no C4a C4 H4 120.7 no C6 C5 H5 120.5 no C4b C5 H5 120.5 no C5 C6 H6 119.6 no C7 C6 H6 119.6 no C6 C7 H7 119.3 no C8 C7 H7 119.3 no C8a C8 H8 121.1 no C7 C8 H8 121.1 no C8a C9 H9 109.4 no C9a C9 H9 109.4 no C10 C9 H9 109.4 no C10 C11 H11a 109.5 no C10 C11 H11b 109.5 no H11a C11 H11b 109.5 no C10 C11 H11c 109.5 no H11a C11 H11c 109.5 no H11b C11 H11c 109.5 no 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 O1 C10 . 1.202(3) no C1 C2 . 1.378(4) no C1 C9a . 1.381(4) no C2 C3 . 1.379(4) no C3 C4 . 1.371(4) no C4 C4a . 1.389(4) no C4a C9a . 1.389(4) no C4a C4b . 1.466(4) no C4b C5 . 1.390(4) no C4b C8a . 1.393(4) no C5 C6 . 1.376(4) no C6 C7 . 1.380(5) no C7 C8 . 1.386(4) no C8 C8a . 1.383(4) no C8a C9 . 1.512(4) no C9 C9a . 1.519(3) no C9 C10 . 1.521(4) no C10 C11 . 1.486(4) no C1 H1 . .9300 no C2 H2 . .9300 no C3 H3 . .9300 no C4 H4 . .9300 no C5 H5 . .9300 no C6 H6 . .9300 no C7 H7 . .9300 no C8 H8 . .9300 no C9 H9 . .9800 no C11 H11a . .9600 no C11 H11b . .9600 no C11 H11c . .9600 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 C9a C1 C2 C3 .3(4) no C1 C2 C3 C4 -.1(4) no C2 C3 C4 C4a -.2(4) no C3 C4 C4a C9a .5(4) no C3 C4 C4a C4b 179.3(3) no C4 C4a C4b C5 .2(5) no C9a C4a C4b C5 179.1(3) no C4 C4a C4b C8a -179.0(3) no C9a C4a C4b C8a .0(3) no C8a C4b C5 C6 -.9(4) no C4a C4b C5 C6 179.9(3) no C4b C5 C6 C7 .2(5) no C5 C6 C7 C8 .1(5) no C6 C7 C8 C8a .3(5) no C7 C8 C8a C4b -1.1(4) no C7 C8 C8a C9 -179.7(3) no C5 C4b C8a C8 1.4(4) no C4a C4b C8a C8 -179.3(2) no C5 C4b C8a C9 -179.7(2) no C4a C4b C8a C9 -.4(3) no C8 C8a C9 C9a 179.5(3) no C4b C8a C9 C9a .7(3) no C8 C8a C9 C10 57.3(4) no C4b C8a C9 C10 -121.5(2) no C2 C1 C9a C4a .0(4) no C2 C1 C9a C9 -179.9(3) no C4 C4a C9a C1 -.3(4) no C4b C4a C9a C1 -179.4(2) no C4 C4a C9a C9 179.6(2) no C4b C4a C9a C9 .5(3) no C8a C9 C9a C1 179.2(3) no C10 C9 C9a C1 -59.0(4) no C8a C9 C9a C4a -.7(3) no C10 C9 C9a C4a 121.1(2) no C8a C9 C10 O1 -123.2(3) no C9a C9 C10 O1 121.4(3) no C8a C9 C10 C11 54.7(3) no C9a C9 C10 C11 -60.7(3) no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 9531164 2 PubChem 11356237