#------------------------------------------------------------------------------ #$Date: 2015-02-05 03:06:46 +0200 (Thu, 05 Feb 2015) $ #$Revision: 131167 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/03/06/4030613.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_4030613 loop_ _publ_author_name 'Song, Xian-Rong' 'Qiu, Yi-Feng' 'Song, Bo' 'Hao, Xin-Hua' 'Han, Ya-Ping' 'Gao, Pin' 'Liu, Xue-Yuan' 'Liang, Yong-Min' _publ_section_title ; BF3•Et2O-Promoted Cleavage of the Csp-Csp2 Bond of 2-Propynolphenols/Anilines: A Route to C2-Alkenylated Benzoxazoles and Benzimidazoles. ; _journal_name_full 'The Journal of organic chemistry' _journal_page_first 150204081323006 _journal_paper_doi 10.1021/jo502761x _journal_year 2015 _chemical_formula_moiety 'C21 H13 Cl2 N O' _chemical_formula_sum 'C21 H13 Cl2 N O' _chemical_formula_weight 366.22 _chemical_name_systematic ; ? ; _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _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_date 2014-10-15 _audit_creation_method ; Olex2 1.2 (compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874) ; _cell_angle_alpha 90.00 _cell_angle_beta 97.713(4) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 15.3129(5) _cell_length_b 6.1061(2) _cell_length_c 18.3965(7) _cell_measurement_reflns_used 1549 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 22.2200 _cell_measurement_theta_min 3.8140 _cell_volume 1704.55(10) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58) ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2008)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 16.0733 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_details ; 1 omega 43.00 95.50 1.5000 14.0000 omega____ theta____ kappa____ phi______ frames - 19.7946 178.0000 -180.0000 35 2 omega 2.00 86.00 1.5000 14.0000 omega____ theta____ kappa____ phi______ frames - 19.7946 57.0000 -120.0000 56 3 omega -9.00 39.00 1.5000 14.0000 omega____ theta____ kappa____ phi______ frames - 19.7946 -38.0000 90.0000 32 4 omega 46.00 95.50 1.5000 14.0000 omega____ theta____ kappa____ phi______ frames - 19.7946 178.0000 90.0000 33 ; _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0088757000 _diffrn_orient_matrix_UB_12 0.0655817000 _diffrn_orient_matrix_UB_13 0.0300003000 _diffrn_orient_matrix_UB_21 0.0210659000 _diffrn_orient_matrix_UB_22 -0.0786025000 _diffrn_orient_matrix_UB_23 0.0247652000 _diffrn_orient_matrix_UB_31 0.0407806000 _diffrn_orient_matrix_UB_32 0.0548758000 _diffrn_orient_matrix_UB_33 -0.0003094000 _diffrn_radiation_monochromator mirror _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0394 _diffrn_reflns_av_unetI/netI 0.0687 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 6995 _diffrn_reflns_theta_full 25.50 _diffrn_reflns_theta_max 26.02 _diffrn_reflns_theta_min 3.44 _diffrn_source 'SuperNova (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.389 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.89876 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_density_diffrn 1.427 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 752 _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.13 _refine_diff_density_max 0.184 _refine_diff_density_min -0.257 _refine_diff_density_rms 0.049 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 226 _refine_ls_number_reflns 3354 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.034 _refine_ls_R_factor_all 0.1002 _refine_ls_R_factor_gt 0.0526 _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^)+(0.0300P)^2^+0.2704P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0932 _refine_ls_wR_factor_ref 0.1157 _reflns_number_gt 2019 _reflns_number_total 3354 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file jo502761x_si_002.cif _[local]_cod_data_source_block songxr1015 _cod_original_cell_volume 1704.56(11) _cod_database_code 4030613 _reflns_odcompleteness_completeness 99.50 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups 2.a Aromatic/amide H refined with riding coordinates: C20(H20), C18(H18), C8(H8), C21(H21), C17(H17), C11(H11), C12(H12), C15(H15), C14(H14), C3(H3), C5(H5), C4(H4), C6(H6) ; _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 '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_calc_flag _atom_site_refinement_flags_posn Cl2 Cl 0.96338(6) 0.51096(14) 0.24579(5) 0.0690(3) Uani 1 d . Cl1 Cl 0.45088(5) 1.53152(17) 0.11797(6) 0.0802(3) Uani 1 d . O1 O 0.75725(11) 1.6194(3) -0.05308(10) 0.0486(5) Uani 1 d . N1 N 0.89513(14) 1.6012(4) -0.08178(12) 0.0408(6) Uani 1 d . C16 C 0.84441(16) 1.0613(4) 0.10036(14) 0.0347(6) Uani 1 d . C10 C 0.71778(16) 1.3231(4) 0.06558(14) 0.0347(6) Uani 1 d . C20 C 0.94018(16) 0.7450(4) 0.12031(16) 0.0420(7) Uani 1 d . H20 H 0.9794 0.6475 0.1032 0.050 Uiso 1 calc R C18 C 0.82292(17) 1.0316(4) 0.17046(16) 0.0420(7) Uani 1 d . H18 H 0.7830 1.1268 0.1877 0.050 Uiso 1 calc R C9 C 0.80753(15) 1.2469(4) 0.05357(14) 0.0349(6) Uani 1 d . C8 C 0.85618(17) 1.3398(4) 0.00716(15) 0.0405(7) Uani 1 d . H8 H 0.9118 1.2783 0.0076 0.049 Uiso 1 calc R C1 C 0.83765(17) 1.5185(5) -0.04334(16) 0.0418(7) Uani 1 d . C21 C 0.90351(16) 0.9138(4) 0.07604(15) 0.0390(7) Uani 1 d . H21 H 0.9187 0.9290 0.0290 0.047 Uiso 1 calc R C17 C 0.85914(18) 0.8640(5) 0.21563(16) 0.0454(7) Uani 1 d . H17 H 0.8439 0.8472 0.2626 0.055 Uiso 1 calc R C11 C 0.70446(17) 1.5311(4) 0.09152(15) 0.0396(7) Uani 1 d . H11 H 0.7514 1.6287 0.0988 0.047 Uiso 1 calc R C12 C 0.62228(18) 1.5966(5) 0.10693(16) 0.0465(8) Uani 1 d . H12 H 0.6142 1.7367 0.1247 0.056 Uiso 1 calc R C19 C 0.91774(17) 0.7235(4) 0.18994(16) 0.0411(7) Uani 1 d . C15 C 0.64646(17) 1.1803(5) 0.05495(16) 0.0457(8) Uani 1 d . H15 H 0.6541 1.0394 0.0377 0.055 Uiso 1 calc R C14 C 0.56410(18) 1.2460(5) 0.06978(17) 0.0531(8) Uani 1 d . H14 H 0.5166 1.1501 0.0621 0.064 Uiso 1 calc R C2 C 0.85153(18) 1.7747(5) -0.12023(15) 0.0406(7) Uani 1 d . C13 C 0.55301(17) 1.4527(5) 0.09576(17) 0.0484(8) Uani 1 d . C3 C 0.8793(2) 1.9250(5) -0.16833(16) 0.0542(8) Uani 1 d . H3 H 0.9355 1.9183 -0.1821 0.065 Uiso 1 calc R C7 C 0.76675(19) 1.7869(5) -0.10202(15) 0.0433(7) Uani 1 d . C5 C 0.7361(3) 2.0939(6) -0.1753(2) 0.0709(10) Uani 1 d . H5 H 0.6982 2.2048 -0.1944 0.085 Uiso 1 calc R C4 C 0.8203(3) 2.0852(6) -0.19507(18) 0.0664(10) Uani 1 d . H4 H 0.8373 2.1899 -0.2271 0.080 Uiso 1 calc R C6 C 0.7070(2) 1.9445(6) -0.12850(18) 0.0632(9) Uani 1 d . H6 H 0.6504 1.9495 -0.1155 0.076 Uiso 1 calc R 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 Cl2 0.0815(6) 0.0583(6) 0.0652(6) 0.0182(5) 0.0023(5) 0.0159(5) Cl1 0.0416(5) 0.1039(8) 0.0996(8) 0.0119(6) 0.0262(5) 0.0166(5) O1 0.0391(11) 0.0557(13) 0.0521(13) 0.0105(11) 0.0103(10) 0.0048(10) N1 0.0417(13) 0.0384(14) 0.0448(15) 0.0043(12) 0.0151(11) 0.0001(11) C16 0.0336(14) 0.0336(15) 0.0376(16) -0.0024(14) 0.0074(12) -0.0014(12) C10 0.0319(13) 0.0353(16) 0.0370(16) 0.0017(13) 0.0054(12) -0.0019(13) C20 0.0333(14) 0.0373(17) 0.056(2) -0.0055(16) 0.0084(14) 0.0041(13) C18 0.0469(16) 0.0367(17) 0.0442(18) -0.0036(15) 0.0125(14) 0.0050(14) C9 0.0324(14) 0.0339(16) 0.0390(16) -0.0034(14) 0.0075(12) -0.0028(12) C8 0.0369(14) 0.0378(16) 0.0474(18) 0.0055(15) 0.0076(13) 0.0048(13) C1 0.0404(15) 0.0399(17) 0.0454(18) 0.0021(15) 0.0069(14) 0.0023(14) C21 0.0378(14) 0.0381(16) 0.0423(17) 0.0007(15) 0.0100(13) 0.0002(14) C17 0.0546(18) 0.0454(18) 0.0384(17) 0.0005(16) 0.0145(14) -0.0033(16) C11 0.0354(14) 0.0336(16) 0.0514(19) -0.0002(14) 0.0122(13) -0.0041(13) C12 0.0490(17) 0.0425(18) 0.0507(19) 0.0020(15) 0.0164(15) 0.0073(15) C19 0.0408(15) 0.0371(17) 0.0436(18) 0.0001(15) -0.0013(13) -0.0009(14) C15 0.0420(16) 0.0407(17) 0.055(2) -0.0017(16) 0.0104(14) -0.0049(14) C14 0.0375(16) 0.058(2) 0.063(2) -0.0018(18) 0.0063(15) -0.0131(16) C2 0.0486(17) 0.0388(17) 0.0346(16) -0.0031(14) 0.0059(13) -0.0092(14) C13 0.0331(15) 0.061(2) 0.053(2) 0.0128(18) 0.0118(14) 0.0038(15) C3 0.065(2) 0.050(2) 0.048(2) 0.0049(17) 0.0064(16) -0.0140(18) C7 0.0510(17) 0.0407(18) 0.0377(17) 0.0068(15) 0.0040(14) -0.0012(15) C5 0.087(3) 0.061(2) 0.060(2) 0.012(2) -0.009(2) 0.016(2) C4 0.098(3) 0.048(2) 0.050(2) 0.0130(18) 0.000(2) -0.012(2) C6 0.060(2) 0.070(2) 0.058(2) 0.008(2) -0.0011(17) 0.0123(19) 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' Cl Cl 0.1484 0.1585 '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' O O 0.0106 0.0060 '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 C1 O1 C7 104.3(2) C1 N1 C2 104.9(2) C18 C16 C9 121.3(2) C18 C16 C21 117.4(2) C21 C16 C9 121.3(2) C11 C10 C9 121.2(2) C11 C10 C15 118.4(2) C15 C10 C9 120.3(2) C21 C20 H20 120.5 C19 C20 H20 120.5 C19 C20 C21 119.1(3) C16 C18 H18 119.0 C16 C18 C17 121.9(3) C17 C18 H18 119.0 C16 C9 C10 115.9(2) C8 C9 C16 119.6(2) C8 C9 C10 124.5(2) C9 C8 H8 114.4 C9 C8 C1 131.2(3) C1 C8 H8 114.4 O1 C1 C8 121.6(2) N1 C1 O1 114.6(2) N1 C1 C8 123.8(2) C16 C21 H21 119.3 C20 C21 C16 121.5(3) C20 C21 H21 119.3 C18 C17 H17 120.6 C19 C17 C18 118.9(3) C19 C17 H17 120.6 C10 C11 H11 119.5 C10 C11 C12 121.1(2) C12 C11 H11 119.5 C11 C12 H12 120.3 C13 C12 C11 119.3(3) C13 C12 H12 120.3 C20 C19 Cl2 119.3(2) C17 C19 Cl2 119.5(2) C17 C19 C20 121.2(3) C10 C15 H15 119.7 C14 C15 C10 120.6(3) C14 C15 H15 119.7 C15 C14 H14 120.2 C13 C14 C15 119.7(3) C13 C14 H14 120.2 C3 C2 N1 131.5(3) C3 C2 C7 119.9(3) C7 C2 N1 108.6(2) C12 C13 Cl1 119.3(2) C14 C13 Cl1 119.7(2) C14 C13 C12 120.9(3) C2 C3 H3 121.4 C4 C3 C2 117.2(3) C4 C3 H3 121.4 O1 C7 C2 107.5(2) C6 C7 O1 128.8(3) C6 C7 C2 123.6(3) C4 C5 H5 119.0 C6 C5 H5 119.0 C6 C5 C4 122.1(3) C3 C4 C5 121.5(3) C3 C4 H4 119.3 C5 C4 H4 119.3 C7 C6 H6 122.2 C5 C6 C7 115.7(3) C5 C6 H6 122.2 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Cl2 C19 1.742(3) Cl1 C13 1.737(3) O1 C1 1.367(3) O1 C7 1.383(3) N1 C1 1.303(3) N1 C2 1.394(3) C16 C18 1.385(3) C16 C9 1.488(3) C16 C21 1.393(3) C10 C9 1.495(3) C10 C11 1.381(3) C10 C15 1.391(3) C20 H20 0.9300 C20 C21 1.385(4) C20 C19 1.376(4) C18 H18 0.9300 C18 C17 1.386(4) C9 C8 1.333(3) C8 H8 0.9300 C8 C1 1.436(4) C21 H21 0.9300 C17 H17 0.9300 C17 C19 1.371(4) C11 H11 0.9300 C11 C12 1.385(3) C12 H12 0.9300 C12 C13 1.371(4) C15 H15 0.9300 C15 C14 1.385(4) C14 H14 0.9300 C14 C13 1.368(4) C2 C3 1.381(4) C2 C7 1.386(4) C3 H3 0.9300 C3 C4 1.377(4) C7 C6 1.371(4) C5 H5 0.9300 C5 C4 1.387(5) C5 C6 1.370(4) C4 H4 0.9300 C6 H6 0.9300 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 O1 C7 C6 C5 178.3(3) N1 C2 C3 C4 -177.2(3) N1 C2 C7 O1 -0.8(3) N1 C2 C7 C6 177.8(3) C16 C18 C17 C19 -0.2(4) C16 C9 C8 C1 -179.8(3) C10 C9 C8 C1 -3.0(5) C10 C11 C12 C13 -0.4(4) C10 C15 C14 C13 -0.6(4) C18 C16 C9 C10 -30.6(3) C18 C16 C9 C8 146.4(3) C18 C16 C21 C20 -0.6(4) C18 C17 C19 Cl2 -179.6(2) C18 C17 C19 C20 -0.7(4) C9 C16 C18 C17 -177.7(2) C9 C16 C21 C20 177.9(2) C9 C10 C11 C12 -175.9(2) C9 C10 C15 C14 176.5(3) C9 C8 C1 O1 -3.2(5) C9 C8 C1 N1 174.9(3) C1 O1 C7 C2 1.3(3) C1 O1 C7 C6 -177.3(3) C1 N1 C2 C3 178.5(3) C1 N1 C2 C7 -0.1(3) C21 C16 C18 C17 0.8(4) C21 C16 C9 C10 150.9(2) C21 C16 C9 C8 -32.1(4) C21 C20 C19 Cl2 179.81(19) C21 C20 C19 C17 0.9(4) C11 C10 C9 C16 115.9(3) C11 C10 C9 C8 -60.9(4) C11 C10 C15 C14 0.3(4) C11 C12 C13 Cl1 177.8(2) C11 C12 C13 C14 0.1(4) C19 C20 C21 C16 -0.2(4) C15 C10 C9 C16 -60.2(3) C15 C10 C9 C8 123.0(3) C15 C10 C11 C12 0.2(4) C15 C14 C13 Cl1 -177.3(2) C15 C14 C13 C12 0.4(5) C2 N1 C1 O1 0.9(3) C2 N1 C1 C8 -177.4(3) C2 C3 C4 C5 -0.8(5) C2 C7 C6 C5 0.0(5) C3 C2 C7 O1 -179.5(2) C3 C2 C7 C6 -0.9(4) C7 O1 C1 N1 -1.4(3) C7 O1 C1 C8 176.9(3) C7 C2 C3 C4 1.3(4) C4 C5 C6 C7 0.5(5) C6 C5 C4 C3 -0.1(5)