#------------------------------------------------------------------------------ #$Date: 2020-04-24 03:51:16 +0300 (Fri, 24 Apr 2020) $ #$Revision: 251122 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/74/7157480.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_7157480 loop_ _publ_author_name 'Roy, Biswajit' 'Das, Eshani' 'Roy, Avijit' 'Mal, Dipak Ranjan' _publ_section_title ; Ni(II)-catalyzed vinylic C-H functionalization of 2-acetamido-3-arylacrylates to access isotetronic acids ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/D0OB00557F _journal_year 2020 _chemical_formula_sum 'C40 H32 N0 O12' _chemical_formula_weight 704.65 _space_group_crystal_system orthorhombic _space_group_IT_number 43 _space_group_name_Hall 'F 2 -2d' _space_group_name_H-M_alt 'F d d 2' _atom_sites_solution_hydrogens mixed _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2018-10-08 deposited with the CCDC. 2020-04-20 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 18.987(4) _cell_length_b 25.021(6) _cell_length_c 7.0870(18) _cell_measurement_reflns_used 400 _cell_measurement_temperature 300(2) _cell_measurement_theta_max 28.455 _cell_measurement_theta_min 3.174 _cell_volume 3366.8(14) _computing_cell_refinement 'SAINT 6.45 ( Bruker, 2003)' _computing_data_collection 'SMART 5.628 (Bruker, 2003)' _computing_data_reduction 'SAINT 6.45 (Bruker, 2003)' _computing_molecular_graphics 'Diamond 2.1e' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution SIR-97 _diffrn_ambient_temperature 300(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type 'Bruker SMART APEX' _diffrn_measurement_method /w-scans _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0355 _diffrn_reflns_av_unetI/netI 0.0327 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_k_min -33 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_number 8727 _diffrn_reflns_point_group_measured_fraction_full 0.962 _diffrn_reflns_point_group_measured_fraction_max 0.954 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.455 _diffrn_reflns_theta_min 3.174 _diffrn_source 'fine-focus sealed tube' _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_T_max 0.991 _exptl_absorpt_correction_T_min 0.987 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details SADABS _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.390 _exptl_crystal_description cube _exptl_crystal_F_000 1472 _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.127 _refine_diff_density_min -0.245 _refine_diff_density_rms 0.055 _refine_ls_abs_structure_details ; Flack x determined using 545 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 1.2(6) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 122 _refine_ls_number_reflns 2030 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.042 _refine_ls_R_factor_all 0.0676 _refine_ls_R_factor_gt 0.0466 _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^)+(0.0648P)^2^+1.1827P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1106 _refine_ls_wR_factor_ref 0.1232 _reflns_Friedel_coverage 0.774 _reflns_Friedel_fraction_full 0.918 _reflns_Friedel_fraction_max 0.904 _reflns_number_gt 1526 _reflns_number_total 2030 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ob00557f2.cif _cod_data_source_block 9a _cod_original_cell_volume 3366.9(14) _cod_database_code 7157480 _shelx_shelxl_version_number 2014/7 _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_res_file ; shelx.res created by SHELXL-2014/7 TITL SIR97 run in space group F d d 2 CELL 0.71073 18.9874 25.0212 7.0870 90.000 90.000 90.000 ZERR 4.00 0.0043 0.0061 0.0018 0.000 0.000 0.000 LATT -4 SYMM - X, - Y, Z SYMM 1/4 - X, 1/4 + Y, 1/4 + Z SYMM 1/4 + X, 1/4 - Y, 1/4 + Z SFAC C H N O UNIT 160 128 0 48 MERG 2 FMAP 2 PLAN 5 ACTA BOND $H CONF L.S. 23 TEMP 26.90 WGHT 0.064800 1.182700 FVAR 0.05063 O1 4 0.119747 0.354377 0.162843 11.00000 0.05994 0.03117 = 0.08830 0.00338 0.00346 -0.00217 O3 4 0.139600 0.214040 0.189320 11.00000 0.04999 0.03124 = 0.10556 0.00165 0.00156 0.00138 C9 1 0.045780 0.279229 0.172864 11.00000 0.05108 0.03474 = 0.04511 -0.00288 0.00134 0.00065 C8 1 0.113055 0.263506 0.179672 11.00000 0.04949 0.03203 = 0.05883 0.00021 0.00294 0.00079 O2 4 0.222614 0.312249 0.177817 11.00000 0.05022 0.04533 = 0.13518 0.00525 0.00542 -0.00855 C2 1 -0.019050 0.248240 0.173511 11.00000 0.05057 0.04651 = 0.04206 -0.00171 0.00316 -0.00231 C3 1 -0.019127 0.192745 0.157073 11.00000 0.05890 0.04604 = 0.05667 -0.00155 0.00424 -0.00631 AFIX 43 H3 2 0.023368 0.174421 0.148546 11.00000 -1.20000 AFIX 0 C16 1 0.046721 0.338842 0.162013 11.00000 0.05438 0.03762 = 0.06432 -0.00056 0.00076 0.00390 AFIX 23 H16A 2 0.023876 0.350949 0.047295 11.00000 -1.20000 H16B 2 0.022322 0.354206 0.269336 11.00000 -1.20000 AFIX 0 C6 1 -0.083554 0.274416 0.188229 11.00000 0.05097 0.06047 = 0.08211 -0.00453 0.00701 0.00059 AFIX 43 H6 2 -0.084911 0.311420 0.200006 11.00000 -1.20000 AFIX 0 C4 1 -0.081752 0.164736 0.153338 11.00000 0.07475 0.06049 = 0.06557 -0.00293 0.00467 -0.02294 AFIX 43 H4 2 -0.081220 0.127742 0.140741 11.00000 -1.20000 AFIX 0 C13 1 0.159028 0.310193 0.173238 11.00000 0.05295 0.03555 = 0.07171 -0.00043 0.00239 -0.00192 C5 1 -0.144897 0.191285 0.168157 11.00000 0.05432 0.09705 = 0.08831 -0.00105 0.01093 -0.02690 AFIX 43 H5 2 -0.187048 0.172361 0.166462 11.00000 -1.20000 AFIX 0 C1 1 -0.145289 0.245603 0.185371 11.00000 0.04924 0.08777 = 0.11012 -0.00780 0.00587 -0.00413 AFIX 43 H1 2 -0.188067 0.263484 0.195357 11.00000 -1.20000 AFIX 0 H3A 2 0.187668 0.214441 0.189960 11.00000 0.07489 HKLF 4 REM SIR97 run in space group F d d 2 REM R1 = 0.0466 for 1526 Fo > 4sig(Fo) and 0.0676 for all 2030 data REM 122 parameters refined using 1 restraints END WGHT 0.0646 1.2046 REM Highest difference peak 0.127, deepest hole -0.245, 1-sigma level 0.055 Q1 1 -0.0490 0.2797 -0.0894 11.00000 0.05 0.13 Q2 1 -0.0152 0.2635 0.3948 11.00000 0.05 0.13 Q3 1 0.0443 0.4163 0.1792 11.00000 0.05 0.13 Q4 1 -0.0545 0.3101 -0.0515 11.00000 0.05 0.12 Q5 1 -0.0335 0.0970 0.2244 11.00000 0.05 0.12 ; _shelx_res_checksum 30982 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, z' '-x+1/4, y+1/4, z+1/4' 'x+1/4, -y+1/4, z+1/4' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' '-x+1/4, y+3/4, z+3/4' 'x+1/4, -y+3/4, z+3/4' 'x+1/2, y, z+1/2' '-x+1/2, -y, z+1/2' '-x+3/4, y+1/4, z+3/4' 'x+3/4, -y+1/4, z+3/4' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z' '-x+3/4, y+3/4, z+1/4' 'x+3/4, -y+3/4, z+1/4' 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 _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.11975(10) 0.35438(6) 0.1628(4) 0.0598(5) Uani 1 1 d . . . . . O3 O 0.13960(10) 0.21404(6) 0.1893(4) 0.0623(6) Uani 1 1 d . . . . . C9 C 0.04578(13) 0.27923(9) 0.1729(5) 0.0436(5) Uani 1 1 d . . . . . C8 C 0.11306(13) 0.26351(8) 0.1797(5) 0.0468(6) Uani 1 1 d . . . . . O2 O 0.22261(10) 0.31225(8) 0.1778(6) 0.0769(7) Uani 1 1 d . . . . . C2 C -0.01905(11) 0.24824(10) 0.1735(5) 0.0464(6) Uani 1 1 d . . . . . C3 C -0.01913(14) 0.19274(11) 0.1571(5) 0.0539(7) Uani 1 1 d . . . . . H3 H 0.0234 0.1744 0.1485 0.065 Uiso 1 1 calc R U . . . C16 C 0.04672(14) 0.33884(10) 0.1620(6) 0.0521(6) Uani 1 1 d . . . . . H16A H 0.0239 0.3509 0.0473 0.063 Uiso 1 1 calc R U . . . H16B H 0.0223 0.3542 0.2693 0.063 Uiso 1 1 calc R U . . . C6 C -0.08355(14) 0.27442(13) 0.1882(6) 0.0645(8) Uani 1 1 d . . . . . H6 H -0.0849 0.3114 0.2000 0.077 Uiso 1 1 calc R U . . . C4 C -0.08175(18) 0.16474(13) 0.1533(6) 0.0669(8) Uani 1 1 d . . . . . H4 H -0.0812 0.1277 0.1407 0.080 Uiso 1 1 calc R U . . . C13 C 0.15903(14) 0.31019(10) 0.1732(7) 0.0534(6) Uani 1 1 d . . . . . C5 C -0.14490(17) 0.19128(17) 0.1682(8) 0.0799(10) Uani 1 1 d . . . . . H5 H -0.1870 0.1724 0.1665 0.096 Uiso 1 1 calc R U . . . C1 C -0.14529(17) 0.24560(17) 0.1854(8) 0.0824(10) Uani 1 1 d . . . . . H1 H -0.1881 0.2635 0.1954 0.099 Uiso 1 1 calc R U . . . H3A H 0.1877(18) 0.2144(13) 0.190(7) 0.075(10) Uiso 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 O1 0.0599(11) 0.0312(8) 0.0883(15) 0.0034(11) 0.0035(13) -0.0022(7) O3 0.0500(10) 0.0312(8) 0.1056(18) 0.0017(10) 0.0016(14) 0.0014(8) C9 0.0511(12) 0.0347(10) 0.0451(12) -0.0029(11) 0.0013(15) 0.0007(10) C8 0.0495(13) 0.0320(10) 0.0588(15) 0.0002(14) 0.0029(16) 0.0008(9) O2 0.0502(11) 0.0453(10) 0.135(2) 0.0053(13) 0.0054(17) -0.0085(8) C2 0.0506(14) 0.0465(12) 0.0421(13) -0.0017(13) 0.003(2) -0.0023(12) C3 0.0589(14) 0.0460(13) 0.0567(18) -0.0015(13) 0.0042(17) -0.0063(12) C16 0.0544(13) 0.0376(12) 0.0643(16) -0.0006(14) 0.0008(17) 0.0039(11) C6 0.0510(14) 0.0605(17) 0.082(2) -0.0045(18) 0.0070(19) 0.0006(12) C4 0.0748(19) 0.0605(17) 0.066(2) -0.0029(16) 0.005(2) -0.0229(15) C13 0.0530(14) 0.0356(11) 0.0717(17) -0.0004(14) 0.002(2) -0.0019(11) C5 0.0543(17) 0.097(3) 0.088(2) -0.001(2) 0.011(3) -0.0269(18) C1 0.0492(17) 0.088(2) 0.110(3) -0.008(3) 0.006(3) -0.0041(17) 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' 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 C13 O1 C16 108.33(19) . . ? C8 O3 H3A 112(2) . . ? C8 C9 C2 130.6(2) . . ? C8 C9 C16 106.5(2) . . ? C2 C9 C16 122.9(2) . . ? C9 C8 O3 129.3(2) . . ? C9 C8 C13 109.6(2) . . ? O3 C8 C13 121.1(2) . . ? C6 C2 C3 118.3(2) . . ? C6 C2 C9 119.6(2) . . ? C3 C2 C9 122.1(2) . . ? C4 C3 C2 120.6(3) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? O1 C16 C9 106.31(19) . . ? O1 C16 H16A 110.5 . . ? C9 C16 H16A 110.5 . . ? O1 C16 H16B 110.5 . . ? C9 C16 H16B 110.5 . . ? H16A C16 H16B 108.7 . . ? C1 C6 C2 120.1(3) . . ? C1 C6 H6 119.9 . . ? C2 C6 H6 119.9 . . ? C5 C4 C3 120.3(3) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? O2 C13 O1 121.6(2) . . ? O2 C13 C8 129.1(2) . . ? O1 C13 C8 109.3(2) . . ? C1 C5 C4 119.5(3) . . ? C1 C5 H5 120.2 . . ? C4 C5 H5 120.2 . . ? C5 C1 C6 121.2(3) . . ? C5 C1 H1 119.4 . . ? C6 C1 H1 119.4 . . ? 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 O1 C13 1.336(3) . ? O1 C16 1.440(3) . ? O3 C8 1.338(3) . ? O3 H3A 0.91(3) . ? C9 C8 1.337(3) . ? C9 C2 1.455(3) . ? C9 C16 1.494(3) . ? C8 C13 1.459(3) . ? O2 C13 1.209(3) . ? C2 C6 1.393(4) . ? C2 C3 1.393(3) . ? C3 C4 1.380(4) . ? C3 H3 0.9300 . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C6 C1 1.376(4) . ? C6 H6 0.9300 . ? C4 C5 1.375(5) . ? C4 H4 0.9300 . ? C5 C1 1.365(5) . ? C5 H5 0.9300 . ? C1 H1 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 C9 C8 O3 -0.1(7) . . . . ? C16 C9 C8 O3 -179.6(3) . . . . ? C2 C9 C8 C13 179.4(4) . . . . ? C16 C9 C8 C13 -0.2(4) . . . . ? C8 C9 C2 C6 172.3(4) . . . . ? C16 C9 C2 C6 -8.2(5) . . . . ? C8 C9 C2 C3 -8.7(6) . . . . ? C16 C9 C2 C3 170.8(3) . . . . ? C6 C2 C3 C4 0.7(6) . . . . ? C9 C2 C3 C4 -178.3(4) . . . . ? C13 O1 C16 C9 -0.1(4) . . . . ? C8 C9 C16 O1 0.2(4) . . . . ? C2 C9 C16 O1 -179.4(3) . . . . ? C3 C2 C6 C1 -0.3(6) . . . . ? C9 C2 C6 C1 178.8(4) . . . . ? C2 C3 C4 C5 -0.8(7) . . . . ? C16 O1 C13 O2 -179.3(5) . . . . ? C16 O1 C13 C8 0.0(4) . . . . ? C9 C8 C13 O2 179.4(5) . . . . ? O3 C8 C13 O2 -1.1(7) . . . . ? C9 C8 C13 O1 0.1(5) . . . . ? O3 C8 C13 O1 179.6(3) . . . . ? C3 C4 C5 C1 0.4(8) . . . . ? C4 C5 C1 C6 0.0(8) . . . . ? C2 C6 C1 C5 0.0(7) . . . . ?