#------------------------------------------------------------------------------ #$Date: 2011-06-22 00:12:38 +0300 (Wed, 22 Jun 2011) $ #$Revision: 21260 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/7151771.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7151771 loop_ _publ_author_name 'Chen, Ko-Wei' 'Syu, Siang-en' 'Jang, Yeong-Jiunn' 'Lin, Wenwei' _publ_section_title ; A facile approach to highly functional trisubstituted furans via intramolecular Wittig reactions. ; _journal_issue 7 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 2098 _journal_page_last 2106 _journal_volume 9 _journal_year 2011 _chemical_formula_moiety 'C23 H14 Br N O' _chemical_formula_sum 'C23 H14 Br N O' _chemical_formula_weight 400.26 _chemical_name_systematic ; ? ; _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' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 111.158(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 8.4569(2) _cell_length_b 21.6536(7) _cell_length_c 10.4183(3) _cell_measurement_reflns_used 0 _cell_measurement_temperature 200(2) _cell_measurement_theta_max 0 _cell_measurement_theta_min 0 _cell_volume 1779.21(9) _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _diffrn_ambient_temperature 200(2) _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _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 0.0301 _diffrn_reflns_av_sigmaI/netI 0.0324 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 10771 _diffrn_reflns_theta_full 25.01 _diffrn_reflns_theta_max 25.01 _diffrn_reflns_theta_min 2.30 _exptl_absorpt_coefficient_mu 2.321 _exptl_absorpt_correction_T_max 0.6414 _exptl_absorpt_correction_T_min 0.4570 _exptl_absorpt_correction_type multi-scan _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.494 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 808 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.21 _refine_diff_density_max 0.252 _refine_diff_density_min -0.334 _refine_diff_density_rms 0.046 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_hydrogen_treatment fixed _refine_ls_matrix_type full _refine_ls_number_parameters 235 _refine_ls_number_reflns 3133 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.029 _refine_ls_R_factor_all 0.0402 _refine_ls_R_factor_gt 0.0285 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0292P)^2^+0.5894P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0627 _refine_ls_wR_factor_ref 0.0666 _reflns_number_gt 2576 _reflns_number_total 3133 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file c0ob00912a.txt _[local]_cod_data_source_block a11023 _[local]_cod_cif_authors_sg_H-M 'P 21/n' _cod_database_code 7151771 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_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 Br1 Br -0.27852(3) 0.019229(12) 0.52292(3) 0.04554(10) Uani 1 1 d . . . C1 C -0.1432(3) 0.08450(10) 0.4955(2) 0.0306(5) Uani 1 1 d . . . C2 C -0.2006(3) 0.11247(11) 0.3669(2) 0.0365(5) Uani 1 1 d . . . H2 H -0.3018 0.0984 0.2973 0.044 Uiso 1 1 calc R . . C3 C -0.1102(3) 0.16068(11) 0.3408(3) 0.0400(6) Uani 1 1 d . . . H3 H -0.1480 0.1797 0.2527 0.048 Uiso 1 1 calc R . . C4 C 0.0359(3) 0.18114(11) 0.4435(3) 0.0386(6) Uani 1 1 d . . . H4 H 0.0986 0.2143 0.4257 0.046 Uiso 1 1 calc R . . C5 C 0.0910(3) 0.15379(10) 0.5714(2) 0.0343(5) Uani 1 1 d . . . H5 H 0.1906 0.1689 0.6412 0.041 Uiso 1 1 calc R . . C6 C 0.0031(3) 0.10404(10) 0.6009(2) 0.0284(5) Uani 1 1 d . . . C7 C 0.0717(3) 0.07609(10) 0.7382(2) 0.0287(5) Uani 1 1 d . . . C8 C 0.0935(3) 0.01817(10) 0.7892(2) 0.0306(5) Uani 1 1 d . . . H8 H 0.0504 -0.0185 0.7385 0.037 Uiso 1 1 calc R . . C9 C 0.1927(3) 0.02171(10) 0.9328(2) 0.0276(5) Uani 1 1 d . . . C10 C 0.2224(3) 0.08316(10) 0.9621(2) 0.0289(5) Uani 1 1 d . . . C11 C 0.2993(3) 0.12070(10) 1.0868(2) 0.0302(5) Uani 1 1 d . . . C12 C 0.3666(3) 0.17850(11) 1.0792(3) 0.0412(6) Uani 1 1 d . . . H12 H 0.3671 0.1932 0.9935 0.049 Uiso 1 1 calc R . . C13 C 0.4330(3) 0.21476(12) 1.1958(3) 0.0491(7) Uani 1 1 d . . . H13 H 0.4779 0.2543 1.1892 0.059 Uiso 1 1 calc R . . C14 C 0.4345(3) 0.19411(11) 1.3213(3) 0.0440(6) Uani 1 1 d . . . H14 H 0.4815 0.2190 1.4013 0.053 Uiso 1 1 calc R . . C15 C 0.3672(3) 0.13689(11) 1.3296(2) 0.0378(6) Uani 1 1 d . . . H15 H 0.3675 0.1224 1.4158 0.045 Uiso 1 1 calc R . . C16 C 0.2992(3) 0.10054(10) 1.2138(2) 0.0319(5) Uani 1 1 d . . . H16 H 0.2519 0.0614 1.2207 0.038 Uiso 1 1 calc R . . C17 C 0.2580(3) -0.03213(10) 1.0236(2) 0.0274(5) Uani 1 1 d . . . C18 C 0.4165(3) -0.03119(10) 1.1300(2) 0.0311(5) Uani 1 1 d . . . H18 H 0.4839 0.0051 1.1453 0.037 Uiso 1 1 calc R . . C19 C 0.4766(3) -0.08185(10) 1.2128(2) 0.0314(5) Uani 1 1 d . . . H19 H 0.5839 -0.0801 1.2854 0.038 Uiso 1 1 calc R . . C20 C 0.3804(3) -0.13559(10) 1.1904(2) 0.0295(5) Uani 1 1 d . . . C21 C 0.4461(3) -0.18858(11) 1.2783(2) 0.0343(5) Uani 1 1 d . . . C22 C 0.2236(3) -0.13821(10) 1.0827(2) 0.0336(5) Uani 1 1 d . . . H22 H 0.1580 -0.1750 1.0661 0.040 Uiso 1 1 calc R . . C23 C 0.1645(3) -0.08701(10) 1.0005(2) 0.0319(5) Uani 1 1 d . . . H23 H 0.0582 -0.0891 0.9267 0.038 Uiso 1 1 calc R . . N1 N 0.5015(3) -0.22990(10) 1.3476(2) 0.0463(5) Uani 1 1 d . . . O1 O 0.15074(18) 0.11704(7) 0.84335(15) 0.0304(3) Uani 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 Br1 0.04487(16) 0.04520(17) 0.03955(17) 0.00438(12) 0.00680(12) -0.01376(12) C1 0.0350(12) 0.0283(12) 0.0304(13) -0.0001(10) 0.0141(11) 0.0013(10) C2 0.0405(13) 0.0369(13) 0.0298(14) 0.0002(11) 0.0099(11) 0.0040(11) C3 0.0509(16) 0.0397(14) 0.0321(14) 0.0085(11) 0.0185(13) 0.0090(12) C4 0.0412(14) 0.0341(13) 0.0450(16) 0.0090(12) 0.0208(13) 0.0034(11) C5 0.0320(13) 0.0321(13) 0.0385(14) 0.0032(11) 0.0123(11) 0.0021(10) C6 0.0315(12) 0.0271(11) 0.0280(13) 0.0001(10) 0.0124(10) 0.0054(9) C7 0.0286(11) 0.0310(12) 0.0268(12) -0.0025(10) 0.0103(10) -0.0005(9) C8 0.0302(12) 0.0286(12) 0.0328(13) -0.0024(10) 0.0112(10) 0.0009(10) C9 0.0249(11) 0.0301(12) 0.0285(13) 0.0015(10) 0.0103(10) 0.0006(9) C10 0.0275(11) 0.0321(13) 0.0286(13) 0.0033(10) 0.0121(10) 0.0003(9) C11 0.0309(12) 0.0314(12) 0.0288(13) -0.0022(10) 0.0112(11) -0.0010(10) C12 0.0567(16) 0.0374(14) 0.0320(14) -0.0019(11) 0.0189(12) -0.0097(12) C13 0.0670(18) 0.0321(14) 0.0474(17) -0.0044(12) 0.0198(15) -0.0122(13) C14 0.0533(16) 0.0386(14) 0.0360(15) -0.0105(12) 0.0112(13) 0.0014(12) C15 0.0425(14) 0.0407(14) 0.0308(14) 0.0007(11) 0.0141(12) 0.0075(11) C16 0.0336(12) 0.0314(12) 0.0315(13) 0.0003(10) 0.0126(11) 0.0012(10) C17 0.0279(12) 0.0284(12) 0.0294(12) -0.0007(9) 0.0147(11) 0.0011(9) C18 0.0267(12) 0.0281(12) 0.0367(14) -0.0051(10) 0.0091(11) -0.0026(9) C19 0.0266(11) 0.0308(13) 0.0312(13) -0.0059(10) 0.0038(10) 0.0007(10) C20 0.0323(12) 0.0289(12) 0.0257(12) -0.0016(10) 0.0085(10) 0.0029(9) C21 0.0388(13) 0.0314(13) 0.0302(14) -0.0053(11) 0.0093(11) -0.0004(11) C22 0.0327(13) 0.0305(13) 0.0346(14) -0.0008(11) 0.0085(11) -0.0068(10) C23 0.0255(11) 0.0365(13) 0.0277(13) -0.0012(10) 0.0024(10) -0.0027(10) N1 0.0599(14) 0.0354(12) 0.0346(13) -0.0003(11) 0.0064(11) 0.0048(11) O1 0.0350(8) 0.0279(8) 0.0280(9) 0.0004(7) 0.0110(7) 0.0000(7) 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 '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' 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 C6 122.1(2) . . ? C2 C1 Br1 116.67(17) . . ? C6 C1 Br1 121.25(16) . . ? C3 C2 C1 119.7(2) . . ? C3 C2 H2 120.1 . . ? C1 C2 H2 120.1 . . ? C2 C3 C4 119.6(2) . . ? C2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? C5 C4 C3 120.5(2) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C4 C5 C6 121.4(2) . . ? C4 C5 H5 119.3 . . ? C6 C5 H5 119.3 . . ? C1 C6 C5 116.8(2) . . ? C1 C6 C7 124.79(19) . . ? C5 C6 C7 118.4(2) . . ? C8 C7 O1 109.08(19) . . ? C8 C7 C6 135.9(2) . . ? O1 C7 C6 114.63(18) . . ? C7 C8 C9 107.9(2) . . ? C7 C8 H8 126.0 . . ? C9 C8 H8 126.0 . . ? C10 C9 C8 106.06(19) . . ? C10 C9 C17 129.0(2) . . ? C8 C9 C17 124.81(19) . . ? C9 C10 O1 109.40(19) . . ? C9 C10 C11 136.2(2) . . ? O1 C10 C11 114.22(18) . . ? C12 C11 C16 118.5(2) . . ? C12 C11 C10 120.5(2) . . ? C16 C11 C10 120.93(19) . . ? C13 C12 C11 120.4(2) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C14 C13 C12 120.7(2) . . ? C14 C13 H13 119.6 . . ? C12 C13 H13 119.6 . . ? C13 C14 C15 119.2(2) . . ? C13 C14 H14 120.4 . . ? C15 C14 H14 120.4 . . ? C16 C15 C14 120.6(2) . . ? C16 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? C15 C16 C11 120.6(2) . . ? C15 C16 H16 119.7 . . ? C11 C16 H16 119.7 . . ? C18 C17 C23 118.0(2) . . ? C18 C17 C9 121.75(19) . . ? C23 C17 C9 120.2(2) . . ? C19 C18 C17 121.2(2) . . ? C19 C18 H18 119.4 . . ? C17 C18 H18 119.4 . . ? C18 C19 C20 120.1(2) . . ? C18 C19 H19 120.0 . . ? C20 C19 H19 120.0 . . ? C19 C20 C22 119.8(2) . . ? C19 C20 C21 119.3(2) . . ? C22 C20 C21 120.9(2) . . ? N1 C21 C20 178.4(3) . . ? C23 C22 C20 119.5(2) . . ? C23 C22 H22 120.2 . . ? C20 C22 H22 120.2 . . ? C22 C23 C17 121.3(2) . . ? C22 C23 H23 119.3 . . ? C17 C23 H23 119.3 . . ? C10 O1 C7 107.52(16) . . ? 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 Br1 C1 1.904(2) . ? C1 C2 1.388(3) . ? C1 C6 1.392(3) . ? C2 C3 1.378(3) . ? C2 H2 0.9500 . ? C3 C4 1.384(3) . ? C3 H3 0.9500 . ? C4 C5 1.377(3) . ? C4 H4 0.9500 . ? C5 C6 1.404(3) . ? C5 H5 0.9500 . ? C6 C7 1.466(3) . ? C7 C8 1.348(3) . ? C7 O1 1.380(3) . ? C8 C9 1.430(3) . ? C8 H8 0.9500 . ? C9 C10 1.368(3) . ? C9 C17 1.477(3) . ? C10 O1 1.377(3) . ? C10 C11 1.470(3) . ? C11 C12 1.389(3) . ? C11 C16 1.394(3) . ? C12 C13 1.384(3) . ? C12 H12 0.9500 . ? C13 C14 1.378(3) . ? C13 H13 0.9500 . ? C14 C15 1.379(3) . ? C14 H14 0.9500 . ? C15 C16 1.380(3) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 C18 1.397(3) . ? C17 C23 1.399(3) . ? C18 C19 1.375(3) . ? C18 H18 0.9500 . ? C19 C20 1.390(3) . ? C19 H19 0.9500 . ? C20 C22 1.395(3) . ? C20 C21 1.448(3) . ? C21 N1 1.139(3) . ? C22 C23 1.380(3) . ? C22 H22 0.9500 . ? C23 H23 0.9500 . ?