#------------------------------------------------------------------------------ #$Date: 2019-12-21 03:46:13 +0200 (Sat, 21 Dec 2019) $ #$Revision: 245466 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/56/7125684.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_7125684 loop_ _publ_author_name 'Shoji, Taku' 'Sugiyama, Shuhei' 'Kobayashi, Yoshiaki' 'Yamazaki, Akari' 'Ariga, Yukino' 'Katoh, Ryuzi' 'Wakui, Hiroki' 'Yasunami, Masafumi' 'Ito, Shunji' _publ_section_title ; Direct synthesis of 2-arylazulenes by [8 + 2] cycloaddition of 2H-cyclohepta[b]furan-2-ones with silyl enol ethers ; _journal_name_full 'Chemical Communications' _journal_paper_doi 10.1039/C9CC09376A _journal_year 2020 _chemical_formula_moiety 'C15 H13 N' _chemical_formula_sum 'C15 H13 N' _chemical_formula_weight 207.26 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2018-12-07 deposited with the CCDC. 2019-12-20 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 98.605(6) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 8.9324(5) _cell_length_b 5.7383(3) _cell_length_c 21.1175(13) _cell_measurement_reflns_used 6995 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 31.22 _cell_measurement_theta_min 2.26 _cell_volume 1070.23(11) _computing_cell_refinement 'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)' _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)' _computing_molecular_graphics 'CrystalStructure 4.3.1 (Rigaku, 2018)' _computing_publication_material 'CrystalStructure 4.3.1 (Rigaku, 2018)' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 100(2) _diffrn_detector_area_resol_mean 7.111 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Rigaku Varimax with Saturn' _diffrn_measurement_method '\w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0714 _diffrn_reflns_av_unetI/netI 0.0479 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_number 17392 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.994 _diffrn_reflns_theta_min 1.951 _diffrn_source 'rotating anode X-ray generator' _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_T_max 0.999 _exptl_absorpt_correction_T_min 0.737 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour green _exptl_crystal_density_diffrn 1.286 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 440 _exptl_crystal_size_max 0.250 _exptl_crystal_size_mid 0.040 _exptl_crystal_size_min 0.010 _refine_diff_density_max 0.514 _refine_diff_density_min -0.248 _refine_diff_density_rms 0.059 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 146 _refine_ls_number_reflns 2582 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.033 _refine_ls_R_factor_all 0.1026 _refine_ls_R_factor_gt 0.0694 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0624P)^2^+1.1639P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1528 _refine_ls_wR_factor_ref 0.1694 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1827 _reflns_number_total 2582 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9cc09376a2.cif _cod_data_source_block shelxl_CCDC2 _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7125684 _shelx_shelxl_version_number 2018/3 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_min 0.982 _shelx_estimated_absorpt_t_max 0.999 _shelx_res_file ; TITL xcalibur shelxl.res created by SHELXL-2018/3 at 18:20:07 on 04-Dec-2018 CELL 0.71073 8.93240 5.73830 21.11750 90.00000 98.60500 90.00000 ZERR 4 0.00050 0.00030 0.00130 0.00000 0.00600 0.00000 LATT 1 SYMM -X, .50+Y, .50-Z SFAC C H N UNIT 60 52 4 SHEL 99999.000000 0.756947 L.S. 10 FMAP 2 PLAN 3 WPDB -2 HTAB BOND $H CONF LIST 4 TEMP -173.0 ACTA SIZE 0.250 0.040 0.010 WGHT 0.062400 1.163900 FVAR 0.50272 N1 3 0.612149 0.512475 0.427015 11.00000 0.02022 0.03603 = 0.02469 0.00341 0.00625 -0.00027 C1 1 0.222347 0.811456 0.268846 11.00000 0.02454 0.01938 = 0.02586 0.00031 0.00979 0.00175 AFIX 43 H1 2 0.209949 0.951579 0.291451 11.00000 -1.20000 AFIX 0 C2 1 0.329960 0.638508 0.287922 11.00000 0.01837 0.02264 = 0.02592 0.00267 0.01105 -0.00170 C3 1 0.316298 0.460714 0.241384 11.00000 0.02192 0.02089 = 0.02914 -0.00007 0.01015 0.00228 AFIX 43 H3 2 0.377973 0.325459 0.242523 11.00000 -1.20000 AFIX 0 C4 1 0.196568 0.517029 0.193220 11.00000 0.01975 0.02615 = 0.02309 0.00122 0.00852 -0.00096 C5 1 0.146043 0.380714 0.140147 11.00000 0.02107 0.02481 = 0.02463 0.00125 0.00876 0.00010 AFIX 43 H5 2 0.201086 0.241038 0.136330 11.00000 -1.20000 AFIX 0 C6 1 0.025290 0.421715 0.091755 11.00000 0.02461 0.02950 = 0.02491 -0.00203 0.00608 -0.00511 AFIX 43 H6 2 0.009311 0.306150 0.059232 11.00000 -1.20000 AFIX 0 C7 1 -0.075149 0.607531 0.084254 11.00000 0.01930 0.03888 = 0.02398 0.00288 0.00555 -0.00324 AFIX 43 H7 2 -0.150021 0.601024 0.047265 11.00000 -1.20000 AFIX 0 C8 1 -0.082133 0.801289 0.122886 11.00000 0.02306 0.03092 = 0.02612 0.00511 0.00839 -0.00057 AFIX 43 H8 2 -0.162381 0.906852 0.109171 11.00000 -1.20000 AFIX 0 C9 1 0.012073 0.862739 0.178985 11.00000 0.02393 0.02508 = 0.02348 0.00179 0.01111 0.00038 AFIX 43 H9 2 -0.011713 1.005488 0.197979 11.00000 -1.20000 AFIX 0 C10 1 0.135728 0.743814 0.210808 11.00000 0.02160 0.02432 = 0.02321 0.00135 0.00942 -0.00303 C11 1 0.435525 0.636038 0.347615 11.00000 0.01674 0.02905 = 0.02118 0.00366 0.00623 -0.00547 C12 1 0.537794 0.457581 0.367700 11.00000 0.02257 0.02816 = 0.02259 -0.00025 0.00728 -0.00557 AFIX 43 H12 2 0.553049 0.320980 0.344064 11.00000 -1.20000 AFIX 0 C13 1 0.560664 0.726013 0.445599 11.00000 0.02190 0.03732 = 0.02438 -0.00193 0.00748 -0.00162 AFIX 43 H13 2 0.594734 0.803831 0.484817 11.00000 -1.20000 AFIX 0 C14 1 0.452571 0.805338 0.397864 11.00000 0.01821 0.02967 = 0.02689 -0.00071 0.00737 0.00003 AFIX 43 H14 2 0.398333 0.947697 0.398010 11.00000 -1.20000 AFIX 0 C15 1 0.733372 0.378190 0.462585 11.00000 0.02529 0.03995 = 0.03092 0.00948 0.00293 0.00323 AFIX 137 H15A 2 0.830905 0.448133 0.457422 11.00000 -1.20000 H15B 2 0.729251 0.217883 0.446414 11.00000 -1.20000 H15C 2 0.722193 0.377460 0.508048 11.00000 -1.20000 AFIX 0 HKLF 4 REM xcalibur REM wR2 = 0.1694, GooF = S = 1.033, Restrained GooF = 1.033 for all data REM R1 = 0.0694 for 1827 Fo > 4sig(Fo) and 0.1026 for all 2582 data REM 146 parameters refined using 0 restraints END WGHT 0.0624 1.1638 REM No hydrogen bonds found for HTAB generation REM Highest difference peak 0.514, deepest hole -0.248, 1-sigma level 0.059 Q1 1 0.3029 0.8030 0.3072 11.00000 0.05 0.51 Q2 1 0.5825 0.3207 0.3668 11.00000 0.05 0.50 Q3 1 0.4672 0.4832 0.3361 11.00000 0.05 0.50 ; _shelx_res_checksum 75096 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp N1 N 0.6121(2) 0.5125(4) 0.42702(9) 0.0267(5) Uani 1 1 d . . C1 C 0.2223(2) 0.8115(4) 0.26885(11) 0.0226(5) Uani 1 1 d . . H1 H 0.209949 0.951579 0.291451 0.027 Uiso 1 1 calc R U C2 C 0.3300(2) 0.6385(4) 0.28792(11) 0.0215(5) Uani 1 1 d . . C3 C 0.3163(2) 0.4607(4) 0.24138(11) 0.0233(5) Uani 1 1 d . . H3 H 0.377973 0.325459 0.242523 0.028 Uiso 1 1 calc R U C4 C 0.1966(2) 0.5170(4) 0.19322(10) 0.0225(5) Uani 1 1 d . . C5 C 0.1460(2) 0.3807(4) 0.14015(11) 0.0230(5) Uani 1 1 d . . H5 H 0.201086 0.241038 0.136330 0.028 Uiso 1 1 calc R U C6 C 0.0253(3) 0.4217(4) 0.09175(11) 0.0261(5) Uani 1 1 d . . H6 H 0.009311 0.306150 0.059232 0.031 Uiso 1 1 calc R U C7 C -0.0751(3) 0.6075(4) 0.08425(11) 0.0272(5) Uani 1 1 d . . H7 H -0.150021 0.601024 0.047265 0.033 Uiso 1 1 calc R U C8 C -0.0821(3) 0.8013(4) 0.12289(11) 0.0262(5) Uani 1 1 d . . H8 H -0.162381 0.906852 0.109171 0.031 Uiso 1 1 calc R U C9 C 0.0121(2) 0.8627(4) 0.17899(11) 0.0234(5) Uani 1 1 d . . H9 H -0.011713 1.005488 0.197979 0.028 Uiso 1 1 calc R U C10 C 0.1357(2) 0.7438(4) 0.21081(11) 0.0224(5) Uani 1 1 d . . C11 C 0.4355(2) 0.6360(4) 0.34761(10) 0.0220(5) Uani 1 1 d . . C12 C 0.5378(2) 0.4576(4) 0.36770(11) 0.0240(5) Uani 1 1 d . . H12 H 0.553049 0.320980 0.344064 0.029 Uiso 1 1 calc R U C13 C 0.5607(3) 0.7260(4) 0.44560(11) 0.0275(5) Uani 1 1 d . . H13 H 0.594734 0.803831 0.484817 0.033 Uiso 1 1 calc R U C14 C 0.4526(2) 0.8053(4) 0.39786(11) 0.0245(5) Uani 1 1 d . . H14 H 0.398333 0.947697 0.398010 0.029 Uiso 1 1 calc R U C15 C 0.7334(3) 0.3782(5) 0.46259(12) 0.0322(6) Uani 1 1 d . . H15A H 0.830905 0.448133 0.457422 0.039 Uiso 1 1 calc R U H15B H 0.729251 0.217883 0.446414 0.039 Uiso 1 1 calc R U H15C H 0.722193 0.377460 0.508048 0.039 Uiso 1 1 calc R U 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 N1 0.0202(9) 0.0360(12) 0.0247(10) 0.0034(9) 0.0063(8) -0.0003(9) C1 0.0245(11) 0.0194(11) 0.0259(11) 0.0003(9) 0.0098(9) 0.0018(9) C2 0.0184(10) 0.0226(11) 0.0259(11) 0.0027(9) 0.0111(9) -0.0017(9) C3 0.0219(11) 0.0209(11) 0.0291(12) -0.0001(10) 0.0101(9) 0.0023(9) C4 0.0197(10) 0.0261(12) 0.0231(11) 0.0012(9) 0.0085(9) -0.0010(9) C5 0.0211(11) 0.0248(12) 0.0246(11) 0.0012(9) 0.0088(9) 0.0001(9) C6 0.0246(11) 0.0295(13) 0.0249(12) -0.0020(10) 0.0061(9) -0.0051(10) C7 0.0193(11) 0.0389(14) 0.0240(12) 0.0029(11) 0.0055(9) -0.0032(10) C8 0.0231(11) 0.0309(13) 0.0261(12) 0.0051(10) 0.0084(9) -0.0006(10) C9 0.0239(11) 0.0251(12) 0.0235(11) 0.0018(9) 0.0111(9) 0.0004(9) C10 0.0216(11) 0.0243(11) 0.0232(11) 0.0014(9) 0.0094(9) -0.0030(9) C11 0.0167(10) 0.0290(12) 0.0212(11) 0.0037(9) 0.0062(8) -0.0055(9) C12 0.0226(11) 0.0282(12) 0.0226(11) -0.0002(10) 0.0073(9) -0.0056(10) C13 0.0219(11) 0.0373(14) 0.0244(12) -0.0019(11) 0.0075(9) -0.0016(10) C14 0.0182(10) 0.0297(12) 0.0269(12) -0.0007(10) 0.0074(9) 0.0000(9) C15 0.0253(12) 0.0399(15) 0.0309(13) 0.0095(11) 0.0029(10) 0.0032(11) 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' 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 C12 N1 C13 109.1(2) C12 N1 C15 125.3(2) C13 N1 C15 125.4(2) C2 C1 C10 108.7(2) C2 C1 H1 125.6 C10 C1 H1 125.6 C1 C2 C3 109.2(2) C1 C2 C11 125.7(2) C3 C2 C11 125.0(2) C4 C3 C2 108.5(2) C4 C3 H3 125.8 C2 C3 H3 125.8 C5 C4 C3 125.4(2) C5 C4 C10 127.8(2) C3 C4 C10 106.88(19) C4 C5 C6 128.5(2) C4 C5 H5 115.8 C6 C5 H5 115.8 C7 C6 C5 129.1(2) C7 C6 H6 115.4 C5 C6 H6 115.4 C8 C7 C6 129.4(2) C8 C7 H7 115.3 C6 C7 H7 115.3 C7 C8 C9 129.0(2) C7 C8 H8 115.5 C9 C8 H8 115.5 C10 C9 C8 128.7(2) C10 C9 H9 115.6 C8 C9 H9 115.6 C9 C10 C1 125.7(2) C9 C10 C4 127.5(2) C1 C10 C4 106.71(19) C12 C11 C14 106.31(19) C12 C11 C2 125.4(2) C14 C11 C2 128.2(2) N1 C12 C11 108.4(2) N1 C12 H12 125.8 C11 C12 H12 125.8 C14 C13 N1 108.3(2) C14 C13 H13 125.9 N1 C13 H13 125.9 C13 C14 C11 107.8(2) C13 C14 H14 126.1 C11 C14 H14 126.1 N1 C15 H15A 109.5 N1 C15 H15B 109.5 H15A C15 H15B 109.5 N1 C15 H15C 109.5 H15A C15 H15C 109.5 H15B C15 H15C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance N1 C12 1.364(3) N1 C13 1.386(3) N1 C15 1.445(3) C1 C2 1.398(3) C1 C10 1.403(3) C1 H1 0.9500 C2 C3 1.409(3) C2 C11 1.457(3) C3 C4 1.399(3) C3 H3 0.9500 C4 C5 1.386(3) C4 C10 1.479(3) C5 C6 1.390(3) C5 H5 0.9500 C6 C7 1.387(3) C6 H6 0.9500 C7 C8 1.386(3) C7 H7 0.9500 C8 C9 1.392(3) C8 H8 0.9500 C9 C10 1.384(3) C9 H9 0.9500 C11 C12 1.395(3) C11 C14 1.430(3) C12 H12 0.9500 C13 C14 1.365(3) C13 H13 0.9500 C14 H14 0.9500 C15 H15A 0.9800 C15 H15B 0.9800 C15 H15C 0.9800 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 C10 C1 C2 C3 1.6(2) C10 C1 C2 C11 -175.97(19) C1 C2 C3 C4 -1.7(2) C11 C2 C3 C4 175.93(19) C2 C3 C4 C5 -178.1(2) C2 C3 C4 C10 1.1(2) C3 C4 C5 C6 177.7(2) C10 C4 C5 C6 -1.4(4) C4 C5 C6 C7 -0.2(4) C5 C6 C7 C8 -0.1(4) C6 C7 C8 C9 1.4(4) C7 C8 C9 C10 -0.9(4) C8 C9 C10 C1 -177.2(2) C8 C9 C10 C4 -1.3(4) C2 C1 C10 C9 175.7(2) C2 C1 C10 C4 -0.9(2) C5 C4 C10 C9 2.5(4) C3 C4 C10 C9 -176.6(2) C5 C4 C10 C1 179.1(2) C3 C4 C10 C1 -0.1(2) C1 C2 C11 C12 176.8(2) C3 C2 C11 C12 -0.4(3) C1 C2 C11 C14 -0.6(3) C3 C2 C11 C14 -177.8(2) C13 N1 C12 C11 -0.6(2) C15 N1 C12 C11 -176.2(2) C14 C11 C12 N1 0.6(2) C2 C11 C12 N1 -177.27(19) C12 N1 C13 C14 0.4(2) C15 N1 C13 C14 176.0(2) N1 C13 C14 C11 0.0(2) C12 C11 C14 C13 -0.4(2) C2 C11 C14 C13 177.4(2)