#------------------------------------------------------------------------------ #$Date: 2016-07-01 13:49:42 +0300 (Fri, 01 Jul 2016) $ #$Revision: 184112 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/11/90/7119074.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_7119074 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 H13 F2 N O4' _chemical_formula_sum 'C25 H13 F2 N O4' _chemical_formula_weight 429.36 _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/cc1kkpxq _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 107.453(11) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 10.033(4) _cell_length_b 19.091(8) _cell_length_c 10.544(5) _cell_measurement_reflns_used 1785 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 21.88 _cell_measurement_theta_min 2.38 _cell_volume 1926.6(14) _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, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 0.968 _diffrn_measured_fraction_theta_max 0.968 _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 0.0954 _diffrn_reflns_av_sigmaI/netI 0.1437 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 10385 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 2.13 _exptl_absorpt_coefficient_mu 0.114 _exptl_absorpt_correction_T_max 0.978 _exptl_absorpt_correction_T_min 0.973 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details sadabs _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.480 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 880 _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.254 _refine_diff_density_min -0.243 _refine_diff_density_rms 0.054 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.917 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 289 _refine_ls_number_reflns 3281 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.917 _refine_ls_R_factor_all 0.1723 _refine_ls_R_factor_gt 0.0605 _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^)+(0.0634P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1167 _refine_ls_wR_factor_ref 0.1387 _reflns_number_gt 1564 _reflns_number_total 3281 _reflns_threshold_expression >2sigma(I) _cod_data_source_file c6cc00525j2.cif _cod_data_source_block 1k _cod_depositor_comments ; The following automatic conversions were performed: '_refine_ls_hydrogen_treatment' value 'CONSTR' changed to 'constr' according to the built-in table from CIF Core dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 4624 2016-04-14 12:54:50Z antanas ; _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7119074 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 0.2179(4) 0.11209(17) 0.4761(3) 0.0354(9) Uani 1 1 d . . . C2 C 0.3175(4) 0.1039(2) 0.5987(4) 0.0503(11) Uani 1 1 d . . . H2 H 0.3053 0.0696 0.6569 0.060 Uiso 1 1 calc R . . C3 C 0.4337(4) 0.1459(2) 0.6352(4) 0.0587(11) Uani 1 1 d . . . H3 H 0.5002 0.1408 0.7178 0.070 Uiso 1 1 calc R . . C4 C 0.4490(4) 0.1953(2) 0.5470(4) 0.0490(10) Uani 1 1 d . . . C5 C 0.3527(4) 0.20666(18) 0.4287(3) 0.0420(10) Uani 1 1 d . . . H5 H 0.3661 0.2421 0.3733 0.050 Uiso 1 1 calc R . . C6 C 0.2326(4) 0.16515(17) 0.3892(3) 0.0330(9) Uani 1 1 d . . . C7 C 0.0395(4) 0.03373(19) 0.3309(3) 0.0383(9) Uani 1 1 d . . . C8 C 0.0964(3) 0.04977(16) 0.2162(3) 0.0330(9) Uani 1 1 d . . . H8 H 0.0421 0.0219 0.1402 0.040 Uiso 1 1 calc R . . C9 C 0.2478(4) 0.02408(18) 0.2516(3) 0.0381(9) Uani 1 1 d . . . C10 C 0.3393(4) 0.04961(17) 0.1749(3) 0.0350(9) Uani 1 1 d . . . C11 C 0.4828(4) 0.04549(17) 0.2326(4) 0.0458(10) Uani 1 1 d . . . H11 H 0.5184 0.0287 0.3190 0.055 Uiso 1 1 calc R . . C12 C 0.5732(4) 0.06584(19) 0.1639(4) 0.0483(10) Uani 1 1 d . . . H12 H 0.6694 0.0625 0.2023 0.058 Uiso 1 1 calc R . . C13 C 0.5182(4) 0.09099(19) 0.0384(4) 0.0493(11) Uani 1 1 d . . . C14 C 0.3783(4) 0.09647(18) -0.0224(4) 0.0499(11) Uani 1 1 d . . . H14 H 0.3444 0.1140 -0.1084 0.060 Uiso 1 1 calc R . . C15 C 0.2886(4) 0.07559(17) 0.0460(3) 0.0425(10) Uani 1 1 d . . . H15 H 0.1927 0.0788 0.0058 0.051 Uiso 1 1 calc R . . C16 C 0.0654(3) 0.12598(17) 0.1796(3) 0.0302(8) Uani 1 1 d . . . C17 C -0.0405(3) 0.14018(19) 0.0484(3) 0.0329(9) Uani 1 1 d . . . C18 C -0.0912(3) 0.21253(17) 0.0171(3) 0.0303(8) Uani 1 1 d . . . C19 C -0.1933(4) 0.22713(19) -0.1000(3) 0.0442(10) Uani 1 1 d . . . H19 H -0.2269 0.1919 -0.1623 0.053 Uiso 1 1 calc R . . C20 C -0.2453(4) 0.2938(2) -0.1247(4) 0.0594(12) Uani 1 1 d . . . H20 H -0.3133 0.3038 -0.2044 0.071 Uiso 1 1 calc R . . C21 C -0.1972(4) 0.3460(2) -0.0318(4) 0.0611(12) Uani 1 1 d . . . H21 H -0.2354 0.3907 -0.0479 0.073 Uiso 1 1 calc R . . C22 C -0.0937(4) 0.33237(19) 0.0840(4) 0.0475(10) Uani 1 1 d . . . H22 H -0.0605 0.3678 0.1459 0.057 Uiso 1 1 calc R . . C23 C -0.0386(3) 0.26507(17) 0.1083(3) 0.0329(9) Uani 1 1 d . . . C24 C 0.0765(4) 0.25212(19) 0.2312(3) 0.0403(9) Uani 1 1 d . . . C25 C 0.1250(3) 0.17835(17) 0.2623(3) 0.0309(8) Uani 1 1 d . . . F1 F 0.5661(2) 0.23606(12) 0.5830(2) 0.0722(7) Uani 1 1 d . . . F2 F 0.6065(2) 0.11126(12) -0.0294(2) 0.0776(8) Uani 1 1 d . . . N1 N 0.1008(3) 0.06726(14) 0.4467(3) 0.0401(8) Uani 1 1 d . . . H1 H 0.0642 0.0605 0.5097 0.048 Uiso 1 1 calc R . . O1 O -0.0581(3) -0.00702(12) 0.3199(2) 0.0481(7) Uani 1 1 d . . . O2 O 0.2880(3) -0.01836(13) 0.3398(3) 0.0602(8) Uani 1 1 d . . . O3 O -0.0817(2) 0.09225(12) -0.0302(2) 0.0516(7) Uani 1 1 d . . . O4 O 0.1269(3) 0.29921(13) 0.3092(3) 0.0665(8) 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 0.040(2) 0.033(2) 0.034(2) -0.0014(18) 0.013(2) 0.001(2) C2 0.057(3) 0.056(3) 0.035(2) 0.015(2) 0.010(2) 0.004(2) C3 0.047(3) 0.077(3) 0.042(2) 0.006(2) -0.001(2) -0.001(3) C4 0.040(3) 0.056(3) 0.047(3) 0.001(2) 0.006(2) -0.011(2) C5 0.047(3) 0.038(2) 0.038(2) 0.0075(18) 0.008(2) -0.002(2) C6 0.033(2) 0.030(2) 0.033(2) -0.0036(17) 0.0049(18) -0.0052(19) C7 0.042(2) 0.030(2) 0.045(3) 0.003(2) 0.015(2) 0.003(2) C8 0.039(2) 0.027(2) 0.037(2) -0.0032(16) 0.0161(18) -0.0035(18) C9 0.049(3) 0.028(2) 0.042(2) 0.0007(19) 0.020(2) 0.007(2) C10 0.035(2) 0.031(2) 0.040(2) -0.0032(18) 0.013(2) 0.0034(18) C11 0.050(3) 0.045(2) 0.042(2) 0.0004(19) 0.012(2) 0.009(2) C12 0.033(2) 0.056(3) 0.056(3) -0.013(2) 0.014(2) -0.004(2) C13 0.059(3) 0.043(2) 0.060(3) -0.004(2) 0.040(3) -0.004(2) C14 0.062(3) 0.049(3) 0.046(2) 0.011(2) 0.028(2) 0.018(2) C15 0.043(2) 0.047(2) 0.040(2) 0.0035(19) 0.017(2) 0.007(2) C16 0.030(2) 0.030(2) 0.031(2) 0.0051(18) 0.0105(17) 0.0022(18) C17 0.036(2) 0.035(2) 0.030(2) -0.0062(19) 0.0128(18) -0.006(2) C18 0.032(2) 0.030(2) 0.029(2) -0.0011(18) 0.0089(18) -0.0009(18) C19 0.051(3) 0.040(2) 0.038(2) 0.0011(19) 0.008(2) -0.003(2) C20 0.062(3) 0.050(3) 0.051(3) 0.010(2) -0.006(2) 0.004(2) C21 0.074(3) 0.033(3) 0.063(3) 0.011(2) 0.000(3) 0.016(2) C22 0.054(3) 0.034(2) 0.048(2) 0.007(2) 0.005(2) -0.003(2) C23 0.038(2) 0.027(2) 0.034(2) 0.0042(18) 0.0112(19) -0.0038(19) C24 0.051(3) 0.028(2) 0.042(2) -0.006(2) 0.014(2) -0.001(2) C25 0.034(2) 0.028(2) 0.033(2) -0.0038(18) 0.0142(18) -0.0072(19) F1 0.0471(15) 0.0843(17) 0.0689(15) 0.0010(13) -0.0071(12) -0.0244(14) F2 0.0730(17) 0.0840(18) 0.0948(18) 0.0090(14) 0.0540(16) -0.0066(14) N1 0.047(2) 0.0427(19) 0.0392(18) 0.0025(16) 0.0269(16) -0.0052(17) O1 0.0520(17) 0.0435(16) 0.0526(15) 0.0013(13) 0.0215(13) -0.0152(15) O2 0.071(2) 0.0534(17) 0.0661(18) 0.0313(16) 0.0353(16) 0.0259(16) O3 0.0541(18) 0.0416(16) 0.0478(15) -0.0120(14) -0.0016(13) 0.0043(14) O4 0.078(2) 0.0322(16) 0.0651(18) -0.0110(14) -0.0146(16) 0.0006(15) 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' F F 0.0171 0.0103 '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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 C2 C1 C6 120.2(3) . . C2 C1 N1 117.2(3) . . C6 C1 N1 122.5(3) . . C3 C2 C1 120.7(3) . . C3 C2 H2 119.6 . . C1 C2 H2 119.6 . . C4 C3 C2 118.2(3) . . C4 C3 H3 120.9 . . C2 C3 H3 120.9 . . C5 C4 C3 123.1(4) . . C5 C4 F1 118.9(3) . . C3 C4 F1 117.9(3) . . C4 C5 C6 120.0(3) . . C4 C5 H5 120.0 . . C6 C5 H5 120.0 . . C5 C6 C1 117.7(3) . . C5 C6 C25 120.5(3) . . C1 C6 C25 121.8(3) . . O1 C7 N1 121.2(3) . . O1 C7 C8 122.2(3) . . N1 C7 C8 116.5(3) . . C16 C8 C7 107.5(2) . . C16 C8 C9 118.8(3) . . C7 C8 C9 109.0(3) . . C16 C8 H8 107.0 . . C7 C8 H8 107.0 . . C9 C8 H8 107.0 . . O2 C9 C10 121.6(3) . . O2 C9 C8 118.6(3) . . C10 C9 C8 119.7(3) . . C11 C10 C15 118.4(3) . . C11 C10 C9 118.4(3) . . C15 C10 C9 123.2(3) . . C12 C11 C10 121.0(3) . . C12 C11 H11 119.5 . . C10 C11 H11 119.5 . . C13 C12 C11 118.2(4) . . C13 C12 H12 120.9 . . C11 C12 H12 120.9 . . F2 C13 C12 118.5(4) . . F2 C13 C14 118.5(4) . . C12 C13 C14 123.1(3) . . C13 C14 C15 118.5(3) . . C13 C14 H14 120.7 . . C15 C14 H14 120.7 . . C14 C15 C10 120.8(3) . . C14 C15 H15 119.6 . . C10 C15 H15 119.6 . . C25 C16 C17 121.4(3) . . C25 C16 C8 122.1(3) . . C17 C16 C8 116.4(3) . . O3 C17 C18 121.8(3) . . O3 C17 C16 119.6(3) . . C18 C17 C16 118.6(3) . . C19 C18 C23 120.3(3) . . C19 C18 C17 120.3(3) . . C23 C18 C17 119.4(3) . . C20 C19 C18 119.8(4) . . C20 C19 H19 120.1 . . C18 C19 H19 120.1 . . C19 C20 C21 120.3(4) . . C19 C20 H20 119.9 . . C21 C20 H20 119.9 . . C22 C21 C20 120.4(4) . . C22 C21 H21 119.8 . . C20 C21 H21 119.8 . . C21 C22 C23 119.5(4) . . C21 C22 H22 120.3 . . C23 C22 H22 120.3 . . C18 C23 C22 119.7(3) . . C18 C23 C24 121.7(3) . . C22 C23 C24 118.6(3) . . O4 C24 C23 121.7(3) . . O4 C24 C25 120.3(3) . . C23 C24 C25 117.9(3) . . C16 C25 C6 121.8(3) . . C16 C25 C24 120.4(3) . . C6 C25 C24 117.7(3) . . C7 N1 C1 127.5(3) . . C7 N1 H1 116.2 . . C1 N1 H1 116.2 . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 C1 C2 1.385(5) . C1 C6 1.403(4) . C1 N1 1.411(4) . C2 C3 1.371(5) . C2 H2 0.9300 . C3 C4 1.365(5) . C3 H3 0.9300 . C4 C5 1.347(5) . C4 F1 1.365(4) . C5 C6 1.397(4) . C5 H5 0.9300 . C6 C25 1.467(4) . C7 O1 1.228(4) . C7 N1 1.353(4) . C7 C8 1.515(4) . C8 C16 1.514(4) . C8 C9 1.533(4) . C8 H8 0.9800 . C9 O2 1.208(4) . C9 C10 1.476(5) . C10 C11 1.386(4) . C10 C15 1.392(4) . C11 C12 1.376(4) . C11 H11 0.9300 . C12 C13 1.360(5) . C12 H12 0.9300 . C13 F2 1.351(4) . C13 C14 1.360(5) . C14 C15 1.371(4) . C14 H14 0.9300 . C15 H15 0.9300 . C16 C25 1.344(4) . C16 C17 1.495(4) . C17 O3 1.221(3) . C17 C18 1.475(4) . C18 C19 1.376(4) . C18 C23 1.380(4) . C19 C20 1.370(5) . C19 H19 0.9300 . C20 C21 1.379(5) . C20 H20 0.9300 . C21 C22 1.370(5) . C21 H21 0.9300 . C22 C23 1.392(4) . C22 H22 0.9300 . C23 C24 1.476(5) . C24 O4 1.221(4) . C24 C25 1.494(5) . 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 O1 0.86 2.08 2.863(3) 150.5 3_556