#------------------------------------------------------------------------------ #$Date: 2016-07-01 13:49:42 +0300 (Fri, 01 Jul 2016) $ #$Revision: 184112 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/11/90/7119072.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_7119072 loop_ _publ_author_name 'Rong-Guo Shi' 'Xiao-Hua Wang' 'Ruzhang Liu' 'Chao-Guo Yan' _publ_section_title ; Two-carbon ring expansion of isatin: a convenient construction of a dibenzo[b,d]azepinone scaffold ; _journal_name_full Chem.Commun. _journal_page_first 6280 _journal_volume 52 _journal_year 2016 _chemical_formula_moiety 'C25 H14 F N O4' _chemical_formula_sum 'C25 H14 F N O4' _chemical_formula_weight 411.37 _chemical_name_systematic ; ? ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_block_doi 10.5517/cc1kkpvn _audit_creation_method SHELXL-97 _audit_update_record ; 2016-01-13 deposited with the CCDC. 2016-04-04 downloaded from the CCDC. ; _cell_angle_alpha 90.00 _cell_angle_beta 105.6330(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 9.7639(11) _cell_length_b 19.413(2) _cell_length_c 10.4751(12) _cell_measurement_reflns_used 6660 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 27.47 _cell_measurement_theta_min 2.28 _cell_volume 1912.1(4) _computing_cell_refinement 'Bruker SMART' _computing_data_collection 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 0.988 _diffrn_measured_fraction_theta_max 0.988 _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _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 0.0271 _diffrn_reflns_av_sigmaI/netI 0.0234 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 16394 _diffrn_reflns_theta_full 27.54 _diffrn_reflns_theta_max 27.54 _diffrn_reflns_theta_min 2.10 _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_T_max 0.977 _exptl_absorpt_correction_T_min 0.966 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details sadabs _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.429 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 848 _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.22 _refine_diff_density_max 0.241 _refine_diff_density_min -0.244 _refine_diff_density_rms 0.046 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 280 _refine_ls_number_reflns 4356 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.031 _refine_ls_R_factor_all 0.0522 _refine_ls_R_factor_gt 0.0414 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0494P)^2^+0.4914P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1027 _refine_ls_wR_factor_ref 0.1107 _reflns_number_gt 3537 _reflns_number_total 4405 _reflns_threshold_expression >2sigma(I) _cod_data_source_file c6cc00525j2.cif _cod_data_source_block 1c _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7119072 loop_ _symmetry_equiv_pos_as_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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.49452(17) 0.95050(8) 0.21695(16) 0.0527(4) Uani 1 1 d . . . H1A H 0.5303 0.9671 0.3027 0.063 Uiso 1 1 calc R . . C2 C 0.58663(18) 0.92972(9) 0.14546(19) 0.0614(4) Uani 1 1 d . . . H2 H 0.6843 0.9328 0.1827 0.074 Uiso 1 1 calc R . . C3 C 0.53435(19) 0.90438(9) 0.01899(19) 0.0615(4) Uani 1 1 d . . . H3 H 0.5967 0.8906 -0.0294 0.074 Uiso 1 1 calc R . . C4 C 0.38890(19) 0.89938(9) -0.03622(17) 0.0574(4) Uani 1 1 d . . . H4 H 0.3539 0.8815 -0.1212 0.069 Uiso 1 1 calc R . . C5 C 0.29551(16) 0.92075(8) 0.03421(14) 0.0472(3) Uani 1 1 d . . . H5 H 0.1979 0.9177 -0.0035 0.057 Uiso 1 1 calc R . . C6 C 0.34788(15) 0.94672(7) 0.16139(13) 0.0409(3) Uani 1 1 d . . . C7 C 0.25405(16) 0.97408(7) 0.24009(14) 0.0433(3) Uani 1 1 d . . . C8 C 0.04178(15) 0.96778(7) 0.32833(13) 0.0384(3) Uani 1 1 d . . . C9 C 0.09839(14) 0.94983(6) 0.21054(12) 0.0364(3) Uani 1 1 d . . . H9 H 0.0437 0.9770 0.1351 0.044 Uiso 1 1 calc R . . C10 C 0.06419(13) 0.87501(6) 0.17688(12) 0.0327(3) Uani 1 1 d . . . C11 C 0.12450(13) 0.82333(6) 0.25977(12) 0.0336(3) Uani 1 1 d . . . C12 C 0.23488(14) 0.83647(7) 0.38504(12) 0.0358(3) Uani 1 1 d . . . C13 C 0.35556(15) 0.79379(8) 0.42241(14) 0.0434(3) Uani 1 1 d . . . H13 H 0.3680 0.7582 0.3672 0.052 Uiso 1 1 calc R . . C14 C 0.45446(16) 0.80523(8) 0.54080(16) 0.0502(4) Uani 1 1 d . . . C15 C 0.44033(18) 0.85683(10) 0.62662(16) 0.0592(4) Uani 1 1 d . . . H15 H 0.5086 0.8631 0.7069 0.071 Uiso 1 1 calc R . . C16 C 0.32297(18) 0.89888(9) 0.59080(15) 0.0531(4) Uani 1 1 d . . . H16 H 0.3116 0.9338 0.6479 0.064 Uiso 1 1 calc R . . C17 C 0.22088(14) 0.89004(7) 0.47021(12) 0.0387(3) Uani 1 1 d . . . C18 C -0.04769(14) 0.86130(7) 0.05005(12) 0.0364(3) Uani 1 1 d . . . C19 C -0.09342(13) 0.78929(7) 0.01761(12) 0.0360(3) Uani 1 1 d . . . C20 C -0.19452(16) 0.77432(8) -0.10126(14) 0.0475(3) Uani 1 1 d . . . H20 H -0.2299 0.8092 -0.1621 0.057 Uiso 1 1 calc R . . C21 C -0.24189(19) 0.70728(9) -0.12813(17) 0.0609(5) Uani 1 1 d . . . H21 H -0.3082 0.6970 -0.2078 0.073 Uiso 1 1 calc R . . C22 C -0.1911(2) 0.65547(9) -0.03715(18) 0.0629(5) Uani 1 1 d . . . H22 H -0.2259 0.6109 -0.0549 0.075 Uiso 1 1 calc R . . C23 C -0.08904(17) 0.66932(8) 0.07992(16) 0.0504(4) Uani 1 1 d . . . H23 H -0.0544 0.6342 0.1403 0.060 Uiso 1 1 calc R . . C24 C -0.03833(14) 0.73633(7) 0.10681(13) 0.0373(3) Uani 1 1 d . . . C25 C 0.07458(14) 0.75023(7) 0.23088(13) 0.0384(3) Uani 1 1 d . . . F1 F 0.57021(10) 0.76349(6) 0.57586(10) 0.0710(3) Uani 1 1 d . . . N1 N 0.10335(13) 0.93506(6) 0.44330(11) 0.0407(3) Uani 1 1 d . . . H1 H 0.0664 0.9426 0.5078 0.049 Uiso 1 1 calc R . . O1 O 0.29529(14) 1.01756(6) 0.32484(12) 0.0668(4) Uani 1 1 d . . . O2 O -0.05577(12) 1.00910(5) 0.31919(10) 0.0508(3) Uani 1 1 d . . . O3 O -0.09957(12) 0.90903(5) -0.02298(11) 0.0569(3) Uani 1 1 d . . . O4 O 0.12228(13) 0.70440(5) 0.30926(12) 0.0631(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 C1 0.0494(9) 0.0524(9) 0.0527(9) 0.0063(7) 0.0073(7) -0.0075(7) C2 0.0442(9) 0.0591(10) 0.0795(12) 0.0159(9) 0.0143(8) 0.0035(7) C3 0.0613(11) 0.0535(10) 0.0797(12) 0.0073(9) 0.0359(9) 0.0070(8) C4 0.0672(11) 0.0577(10) 0.0540(9) -0.0050(8) 0.0281(8) -0.0071(8) C5 0.0467(8) 0.0508(8) 0.0462(8) 0.0000(6) 0.0160(6) -0.0087(7) C6 0.0462(8) 0.0338(7) 0.0434(7) 0.0045(5) 0.0133(6) -0.0064(6) C7 0.0539(8) 0.0361(7) 0.0407(7) -0.0015(6) 0.0145(6) -0.0103(6) C8 0.0453(7) 0.0301(6) 0.0406(7) -0.0034(5) 0.0128(6) -0.0009(5) C9 0.0461(7) 0.0293(6) 0.0340(6) 0.0007(5) 0.0113(5) 0.0002(5) C10 0.0360(6) 0.0308(6) 0.0330(6) -0.0020(5) 0.0120(5) -0.0012(5) C11 0.0349(6) 0.0318(6) 0.0340(6) -0.0019(5) 0.0089(5) 0.0009(5) C12 0.0369(7) 0.0345(7) 0.0347(6) 0.0001(5) 0.0074(5) -0.0012(5) C13 0.0417(7) 0.0424(8) 0.0436(7) -0.0015(6) 0.0071(6) 0.0041(6) C14 0.0373(7) 0.0556(9) 0.0520(8) 0.0041(7) 0.0024(6) 0.0054(6) C15 0.0527(9) 0.0700(11) 0.0444(8) -0.0063(8) -0.0051(7) 0.0002(8) C16 0.0597(9) 0.0547(9) 0.0401(7) -0.0110(7) 0.0049(7) 0.0012(7) C17 0.0425(7) 0.0382(7) 0.0354(6) -0.0006(5) 0.0105(5) -0.0003(6) C18 0.0372(7) 0.0370(7) 0.0349(6) 0.0016(5) 0.0095(5) 0.0015(5) C19 0.0341(6) 0.0384(7) 0.0359(6) -0.0044(5) 0.0099(5) 0.0005(5) C20 0.0483(8) 0.0499(8) 0.0398(7) -0.0050(6) 0.0040(6) 0.0012(7) C21 0.0589(10) 0.0578(10) 0.0540(9) -0.0182(8) -0.0053(8) -0.0040(8) C22 0.0654(11) 0.0413(9) 0.0713(11) -0.0186(8) 0.0000(9) -0.0063(8) C23 0.0538(9) 0.0348(7) 0.0571(9) -0.0068(6) 0.0058(7) 0.0007(6) C24 0.0373(7) 0.0330(7) 0.0407(7) -0.0061(5) 0.0091(5) 0.0016(5) C25 0.0392(7) 0.0316(6) 0.0421(7) 0.0004(5) 0.0067(5) 0.0031(5) F1 0.0474(5) 0.0825(7) 0.0706(6) 0.0007(5) -0.0057(5) 0.0195(5) N1 0.0495(7) 0.0392(6) 0.0364(6) -0.0021(5) 0.0164(5) 0.0054(5) O1 0.0774(8) 0.0616(7) 0.0667(7) -0.0282(6) 0.0282(6) -0.0311(6) O2 0.0601(6) 0.0449(6) 0.0480(6) -0.0032(4) 0.0156(5) 0.0156(5) O3 0.0640(7) 0.0427(6) 0.0516(6) 0.0121(5) -0.0058(5) -0.0006(5) O4 0.0687(8) 0.0361(6) 0.0670(7) 0.0106(5) -0.0116(6) -0.0013(5) 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 '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 C2 C1 C6 120.35(16) . . C2 C1 H1A 119.8 . . C6 C1 H1A 119.8 . . C3 C2 C1 120.08(16) . . C3 C2 H2 120.0 . . C1 C2 H2 120.0 . . C2 C3 C4 119.98(16) . . C2 C3 H3 120.0 . . C4 C3 H3 120.0 . . C5 C4 C3 120.39(16) . . C5 C4 H4 119.8 . . C3 C4 H4 119.8 . . C4 C5 C6 119.76(15) . . C4 C5 H5 120.1 . . C6 C5 H5 120.1 . . C5 C6 C1 119.43(14) . . C5 C6 C7 122.69(13) . . C1 C6 C7 117.83(13) . . O1 C7 C6 121.48(14) . . O1 C7 C9 118.35(13) . . C6 C7 C9 120.11(12) . . O2 C8 N1 121.71(12) . . O2 C8 C9 121.96(12) . . N1 C8 C9 116.33(11) . . C10 C9 C8 107.67(10) . . C10 C9 C7 119.00(11) . . C8 C9 C7 108.73(11) . . C10 C9 H9 107.0 . . C8 C9 H9 107.0 . . C7 C9 H9 107.0 . . C11 C10 C18 121.61(11) . . C11 C10 C9 122.17(11) . . C18 C10 C9 116.10(11) . . C10 C11 C12 121.91(11) . . C10 C11 C25 120.58(11) . . C12 C11 C25 117.41(11) . . C17 C12 C13 118.57(12) . . C17 C12 C11 121.36(12) . . C13 C12 C11 120.06(12) . . C14 C13 C12 119.33(13) . . C14 C13 H13 120.3 . . C12 C13 H13 120.3 . . F1 C14 C13 118.72(14) . . F1 C14 C15 118.66(13) . . C13 C14 C15 122.61(14) . . C16 C15 C14 118.46(14) . . C16 C15 H15 120.8 . . C14 C15 H15 120.8 . . C15 C16 C17 120.98(14) . . C15 C16 H16 119.5 . . C17 C16 H16 119.5 . . C16 C17 C12 120.02(13) . . C16 C17 N1 116.76(12) . . C12 C17 N1 123.16(12) . . O3 C18 C19 121.64(12) . . O3 C18 C10 120.05(12) . . C19 C18 C10 118.31(11) . . C20 C19 C24 119.76(13) . . C20 C19 C18 119.94(12) . . C24 C19 C18 120.29(11) . . C21 C20 C19 119.63(14) . . C21 C20 H20 120.2 . . C19 C20 H20 120.2 . . C22 C21 C20 120.38(14) . . C22 C21 H21 119.8 . . C20 C21 H21 119.8 . . C23 C22 C21 120.59(15) . . C23 C22 H22 119.7 . . C21 C22 H22 119.7 . . C22 C23 C24 119.53(15) . . C22 C23 H23 120.2 . . C24 C23 H23 120.2 . . C23 C24 C19 120.03(12) . . C23 C24 C25 119.08(12) . . C19 C24 C25 120.89(11) . . O4 C25 C24 121.16(12) . . O4 C25 C11 120.68(12) . . C24 C25 C11 118.12(11) . . C8 N1 C17 127.78(11) . . C8 N1 H1 116.1 . . C17 N1 H1 116.1 . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 C1 C2 1.377(2) . C1 C6 1.395(2) . C1 H1A 0.9300 . C2 C3 1.376(3) . C2 H2 0.9300 . C3 C4 1.385(3) . C3 H3 0.9300 . C4 C5 1.382(2) . C4 H4 0.9300 . C5 C6 1.387(2) . C5 H5 0.9300 . C6 C7 1.486(2) . C7 O1 1.2125(17) . C7 C9 1.541(2) . C8 O2 1.2291(16) . C8 N1 1.3509(17) . C8 C9 1.5222(18) . C9 C10 1.5106(17) . C9 H9 0.9800 . C10 C11 1.3534(17) . C10 C18 1.4990(17) . C11 C12 1.4786(17) . C11 C25 1.5045(18) . C12 C17 1.4008(18) . C12 C13 1.4069(19) . C13 C14 1.369(2) . C13 H13 0.9300 . C14 F1 1.3583(17) . C14 C15 1.377(2) . C15 C16 1.374(2) . C15 H15 0.9300 . C16 C17 1.3929(19) . C16 H16 0.9300 . C17 N1 1.4091(17) . C18 O3 1.2212(16) . C18 C19 1.4791(18) . C19 C20 1.3953(18) . C19 C24 1.3958(18) . C20 C21 1.385(2) . C20 H20 0.9300 . C21 C22 1.382(3) . C21 H21 0.9300 . C22 C23 1.382(2) . C22 H22 0.9300 . C23 C24 1.3934(19) . C23 H23 0.9300 . C24 C25 1.4849(18) . C25 O4 1.2150(16) . N1 H1 0.8600 . loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O2 0.86 2.07 2.8642(15) 153.7 3_576