#------------------------------------------------------------------------------ #$Date: 2021-11-05 03:52:46 +0200 (Fri, 05 Nov 2021) $ #$Revision: 270321 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/83/7158395.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_7158395 loop_ _publ_author_name 'Sharma, Nagendra K.' 'Gupta, Manish Kumar' 'Jena, Chinmay Kumar' _publ_section_title ; Pd-Catalyzed C(sp2)-H Olefination: Synthesis of N-alkylated Isoindolinone Scaffolds from Arylamide of Amino acid esters ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/D1OB01997J _journal_year 2021 _chemical_formula_sum 'C14 H13 N O5' _chemical_formula_weight 275.25 _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 _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2021-07-21 deposited with the CCDC. 2021-11-04 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 105.607(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.9566(4) _cell_length_b 13.9478(11) _cell_length_c 8.1538(3) _cell_measurement_temperature 293(2) _cell_volume 1309.66(12) _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.960 _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0328 _diffrn_reflns_av_unetI/netI 0.0268 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.960 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_number 10426 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.960 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 75.317 _diffrn_reflns_theta_min 3.839 _exptl_absorpt_coefficient_mu 0.904 _exptl_crystal_density_diffrn 1.396 _exptl_crystal_F_000 576 _refine_diff_density_max 0.229 _refine_diff_density_min -0.149 _refine_diff_density_rms 0.035 _refine_ls_extinction_coef 0.0025(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2014/7 (Sheldrick 2014' _refine_ls_goodness_of_fit_ref 1.082 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 184 _refine_ls_number_reflns 2602 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.082 _refine_ls_R_factor_all 0.0420 _refine_ls_R_factor_gt 0.0386 _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^)+(0.0628P)^2^+0.1785P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1124 _refine_ls_wR_factor_ref 0.1156 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2307 _reflns_number_total 2602 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1ob01997j2.cif _cod_data_source_block nks_mkg_454b _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7158395 _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 ; nks_mkg_454b.res created by SHELXL-2014/7 TITL NKS_MKG_454B in P21/c #14 REM reset to P21/c #14 CELL 1.54184 11.95663 13.94779 8.15377 90 105.6069 90 ZERR 4 0.00039 0.00107 0.00025 0 0.0032 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H N O UNIT 56 52 4 20 L.S. 4 PLAN 5 CONF BOND $H fmap 2 MORE -1 ACTA REM REM REM WGHT 0.062800 0.178500 EXTI 0.002498 FVAR 0.46563 O14 4 0.014342 0.703120 0.222411 11.00000 0.04779 0.06581 = 0.04843 -0.01053 0.00805 -0.00325 O12 4 -0.061073 0.619263 -0.015528 11.00000 0.04285 0.05905 = 0.05560 -0.01214 -0.00125 -0.00506 N1 3 0.238984 0.676681 0.182345 11.00000 0.03664 0.03986 = 0.04837 -0.00038 0.00436 0.00042 O17 4 0.131675 0.983136 -0.021128 11.00000 0.06202 0.04455 = 0.06238 0.01117 0.00728 0.00563 C15 1 0.195540 0.840532 0.107243 11.00000 0.04207 0.04241 = 0.04346 -0.00002 0.00583 0.00103 AFIX 43 H15 2 0.132322 0.816625 0.024292 11.00000 -1.20000 AFIX 0 O20 4 0.324580 0.532137 0.281499 11.00000 0.05686 0.04127 = 0.07943 0.00623 0.00680 0.00371 C8 1 0.374300 0.779383 0.343507 11.00000 0.03572 0.04702 = 0.04163 -0.00008 0.01000 0.00014 O19 4 0.270908 0.992480 0.220731 11.00000 0.10396 0.04684 = 0.08909 -0.01287 -0.02683 0.00603 C9 1 0.264426 0.774626 0.205981 11.00000 0.03761 0.03987 = 0.04138 -0.00145 0.01073 0.00014 C3 1 0.410579 0.685950 0.387565 11.00000 0.03567 0.04954 = 0.04603 0.00457 0.00990 0.00137 C2 1 0.324737 0.618915 0.283498 11.00000 0.03886 0.04340 = 0.05095 0.00538 0.01104 0.00296 C11 1 0.026091 0.657756 0.103449 11.00000 0.04184 0.03654 = 0.03977 0.00257 0.00015 -0.00179 C16 1 0.207505 0.944417 0.113923 11.00000 0.05031 0.04347 = 0.05002 0.00045 0.00985 0.00426 C10 1 0.138827 0.636860 0.061208 11.00000 0.04433 0.04396 = 0.04794 -0.00759 0.00520 -0.00153 AFIX 23 H10A 2 0.148421 0.567950 0.056424 11.00000 -1.20000 H10B 2 0.134865 0.662538 -0.050771 11.00000 -1.20000 AFIX 0 C4 1 0.511982 0.664387 0.510661 11.00000 0.04106 0.06293 = 0.05680 0.01014 0.00622 0.00502 AFIX 43 H4 2 0.534881 0.601307 0.537579 11.00000 -1.20000 AFIX 0 C6 1 0.542817 0.833761 0.550994 11.00000 0.04470 0.07024 = 0.06034 -0.00983 0.00243 -0.00983 AFIX 43 H6 2 0.588389 0.883687 0.608634 11.00000 -1.20000 AFIX 0 C7 1 0.441465 0.855125 0.426137 11.00000 0.04566 0.05061 = 0.05610 -0.00504 0.00594 -0.00371 AFIX 43 H7 2 0.419315 0.918314 0.398779 11.00000 -1.20000 AFIX 0 C5 1 0.577635 0.740519 0.591724 11.00000 0.03921 0.08155 = 0.05627 0.00429 -0.00114 0.00033 AFIX 43 H5 2 0.646435 0.728788 0.675124 11.00000 -1.20000 AFIX 0 C13 1 -0.176384 0.638319 0.001023 11.00000 0.04142 0.06384 = 0.07717 -0.00565 -0.00089 -0.00246 AFIX 137 H13A 2 -0.232649 0.606785 -0.089275 11.00000 -1.50000 H13B 2 -0.190435 0.706160 -0.005433 11.00000 -1.50000 H13C 2 -0.182641 0.614666 0.108767 11.00000 -1.50000 AFIX 0 C18 1 0.133753 1.085538 -0.035492 11.00000 0.08326 0.04539 = 0.08081 0.01608 0.02176 0.00995 AFIX 137 H18A 2 0.080459 1.105042 -0.140680 11.00000 -1.50000 H18B 2 0.210738 1.106064 -0.033539 11.00000 -1.50000 H18C 2 0.111456 1.114068 0.058124 11.00000 -1.50000 AFIX 0 HKLF 4 REM NKS_MKG_454B in P21/c #14 REM R1 = 0.0386 for 2307 Fo > 4sig(Fo) and 0.0420 for all 2602 data REM 184 parameters refined using 0 restraints END WGHT 0.0628 0.1785 REM Highest difference peak 0.229, deepest hole -0.149, 1-sigma level 0.035 Q1 1 0.3236 0.9760 0.1693 11.00000 0.05 0.23 Q2 1 0.3796 0.6520 0.3336 11.00000 0.05 0.17 Q3 1 0.2634 0.7245 0.1761 11.00000 0.05 0.17 Q4 1 0.2207 0.8185 0.1971 11.00000 0.05 0.17 Q5 1 0.4405 0.6747 0.4701 11.00000 0.05 0.16 ; _shelx_res_checksum 73695 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 _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O14 O 0.01434(8) 0.70312(8) 0.22241(11) 0.0550(3) Uani 1 1 d . . . . . O12 O -0.06107(8) 0.61926(7) -0.01553(12) 0.0553(3) Uani 1 1 d . . . . . N1 N 0.23898(9) 0.67668(7) 0.18235(13) 0.0430(3) Uani 1 1 d . . . . . O17 O 0.13167(9) 0.98314(7) -0.02113(13) 0.0581(3) Uani 1 1 d . . . . . C15 C 0.19554(11) 0.84053(9) 0.10724(15) 0.0437(3) Uani 1 1 d . . . . . H15 H 0.1323 0.8166 0.0243 0.052 Uiso 1 1 calc R U . . . O20 O 0.32458(9) 0.53214(7) 0.28150(14) 0.0614(3) Uani 1 1 d . . . . . C8 C 0.37430(10) 0.77938(9) 0.34351(15) 0.0415(3) Uani 1 1 d . . . . . O19 O 0.27091(13) 0.99248(8) 0.22073(18) 0.0902(5) Uani 1 1 d . . . . . C9 C 0.26443(10) 0.77463(9) 0.20598(14) 0.0396(3) Uani 1 1 d . . . . . C3 C 0.41058(10) 0.68595(9) 0.38757(15) 0.0440(3) Uani 1 1 d . . . . . C2 C 0.32474(10) 0.61892(9) 0.28350(16) 0.0446(3) Uani 1 1 d . . . . . C11 C 0.02609(11) 0.65776(8) 0.10345(14) 0.0415(3) Uani 1 1 d . . . . . C16 C 0.20751(12) 0.94442(10) 0.11392(17) 0.0486(3) Uani 1 1 d . . . . . C10 C 0.13883(11) 0.63686(10) 0.06121(16) 0.0468(3) Uani 1 1 d . . . . . H10A H 0.1484 0.5679 0.0564 0.056 Uiso 1 1 calc R U . . . H10B H 0.1349 0.6625 -0.0508 0.056 Uiso 1 1 calc R U . . . C4 C 0.51198(12) 0.66439(11) 0.51066(17) 0.0549(4) Uani 1 1 d . . . . . H4 H 0.5349 0.6013 0.5376 0.066 Uiso 1 1 calc R U . . . C6 C 0.54282(13) 0.83376(12) 0.55099(19) 0.0607(4) Uani 1 1 d . . . . . H6 H 0.5884 0.8837 0.6086 0.073 Uiso 1 1 calc R U . . . C7 C 0.44146(12) 0.85512(10) 0.42614(17) 0.0523(3) Uani 1 1 d . . . . . H7 H 0.4193 0.9183 0.3988 0.063 Uiso 1 1 calc R U . . . C5 C 0.57764(12) 0.74052(13) 0.59172(19) 0.0617(4) Uani 1 1 d . . . . . H5 H 0.6464 0.7288 0.6751 0.074 Uiso 1 1 calc R U . . . C13 C -0.17638(12) 0.63832(12) 0.0010(2) 0.0641(4) Uani 1 1 d . . . . . H13A H -0.2326 0.6068 -0.0893 0.096 Uiso 1 1 calc R U . . . H13B H -0.1904 0.7062 -0.0054 0.096 Uiso 1 1 calc R U . . . H13C H -0.1826 0.6147 0.1088 0.096 Uiso 1 1 calc R U . . . C18 C 0.13375(16) 1.08554(11) -0.0355(2) 0.0699(5) Uani 1 1 d . . . . . H18A H 0.0805 1.1050 -0.1407 0.105 Uiso 1 1 calc R U . . . H18B H 0.2107 1.1061 -0.0335 0.105 Uiso 1 1 calc R U . . . H18C H 0.1115 1.1141 0.0581 0.105 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 O14 0.0478(5) 0.0658(6) 0.0484(5) -0.0105(4) 0.0081(4) -0.0033(4) O12 0.0428(5) 0.0591(6) 0.0556(5) -0.0121(4) -0.0012(4) -0.0051(4) N1 0.0366(5) 0.0399(5) 0.0484(6) -0.0004(4) 0.0044(4) 0.0004(4) O17 0.0620(6) 0.0445(5) 0.0624(6) 0.0112(4) 0.0073(5) 0.0056(4) C15 0.0421(6) 0.0424(6) 0.0435(6) 0.0000(5) 0.0058(5) 0.0010(5) O20 0.0569(6) 0.0413(5) 0.0794(7) 0.0062(4) 0.0068(5) 0.0037(4) C8 0.0357(6) 0.0470(7) 0.0416(6) -0.0001(5) 0.0100(5) 0.0001(5) O19 0.1040(10) 0.0468(6) 0.0891(8) -0.0129(6) -0.0268(7) 0.0060(6) C9 0.0376(6) 0.0399(6) 0.0414(6) -0.0014(5) 0.0107(5) 0.0001(5) C3 0.0357(6) 0.0495(7) 0.0460(6) 0.0046(5) 0.0099(5) 0.0014(5) C2 0.0389(6) 0.0434(7) 0.0510(7) 0.0054(5) 0.0110(5) 0.0030(5) C11 0.0418(6) 0.0365(6) 0.0398(6) 0.0026(5) 0.0001(5) -0.0018(5) C16 0.0503(7) 0.0435(7) 0.0500(7) 0.0005(5) 0.0098(6) 0.0043(5) C10 0.0443(7) 0.0440(6) 0.0479(7) -0.0076(5) 0.0052(5) -0.0015(5) C4 0.0411(7) 0.0629(9) 0.0568(8) 0.0101(6) 0.0062(6) 0.0050(6) C6 0.0447(7) 0.0702(10) 0.0603(8) -0.0098(7) 0.0024(6) -0.0098(7) C7 0.0457(7) 0.0506(7) 0.0561(7) -0.0050(6) 0.0059(6) -0.0037(6) C5 0.0392(7) 0.0815(11) 0.0563(8) 0.0043(7) -0.0011(6) 0.0003(7) C13 0.0414(7) 0.0638(9) 0.0772(10) -0.0057(8) -0.0009(6) -0.0025(6) C18 0.0833(12) 0.0454(8) 0.0808(11) 0.0161(7) 0.0218(9) 0.0100(7) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 '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 C11 O12 C13 115.93(11) . . ? C2 N1 C9 112.70(10) . . ? C2 N1 C10 121.86(10) . . ? C9 N1 C10 125.37(10) . . ? C16 O17 C18 116.53(12) . . ? C9 C15 C16 128.23(12) . . ? C9 C15 H15 115.9 . . ? C16 C15 H15 115.9 . . ? C7 C8 C3 119.27(11) . . ? C7 C8 C9 132.95(12) . . ? C3 C8 C9 107.77(11) . . ? C15 C9 N1 120.51(11) . . ? C15 C9 C8 134.17(11) . . ? N1 C9 C8 105.26(10) . . ? C4 C3 C8 122.90(12) . . ? C4 C3 C2 128.14(12) . . ? C8 C3 C2 108.96(10) . . ? O20 C2 N1 125.05(12) . . ? O20 C2 C3 129.75(12) . . ? N1 C2 C3 105.20(11) . . ? O14 C11 O12 124.33(12) . . ? O14 C11 C10 126.47(11) . . ? O12 C11 C10 109.18(10) . . ? O19 C16 O17 122.02(13) . . ? O19 C16 C15 128.50(13) . . ? O17 C16 C15 109.46(11) . . ? N1 C10 C11 113.44(10) . . ? N1 C10 H10A 108.9 . . ? C11 C10 H10A 108.9 . . ? N1 C10 H10B 108.9 . . ? C11 C10 H10B 108.9 . . ? H10A C10 H10B 107.7 . . ? C5 C4 C3 117.08(14) . . ? C5 C4 H4 121.5 . . ? C3 C4 H4 121.5 . . ? C5 C6 C7 121.75(14) . . ? C5 C6 H6 119.1 . . ? C7 C6 H6 119.1 . . ? C8 C7 C6 118.00(14) . . ? C8 C7 H7 121.0 . . ? C6 C7 H7 121.0 . . ? C6 C5 C4 120.99(13) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? O12 C13 H13A 109.5 . . ? O12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? O12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O17 C18 H18A 109.5 . . ? O17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? O17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? 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 O14 C11 1.1976(15) . ? O12 C11 1.3310(14) . ? O12 C13 1.4456(18) . ? N1 C2 1.3877(15) . ? N1 C9 1.4016(15) . ? N1 C10 1.4428(15) . ? O17 C16 1.3376(16) . ? O17 C18 1.4338(18) . ? C15 C9 1.3471(17) . ? C15 C16 1.4556(18) . ? C15 H15 0.9300 . ? O20 C2 1.2105(16) . ? C8 C7 1.3870(18) . ? C8 C3 1.3898(18) . ? C8 C9 1.4816(16) . ? O19 C16 1.1947(18) . ? C3 C4 1.3831(17) . ? C3 C2 1.4762(17) . ? C11 C10 1.5068(18) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C4 C5 1.379(2) . ? C4 H4 0.9300 . ? C6 C5 1.379(2) . ? C6 C7 1.3892(19) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C5 H5 0.9300 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? 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 C16 C15 C9 N1 179.45(12) . . . . ? C16 C15 C9 C8 -3.6(2) . . . . ? C2 N1 C9 C15 174.16(11) . . . . ? C10 N1 C9 C15 -2.71(18) . . . . ? C2 N1 C9 C8 -3.55(13) . . . . ? C10 N1 C9 C8 179.59(11) . . . . ? C7 C8 C9 C15 4.6(2) . . . . ? C3 C8 C9 C15 -174.41(13) . . . . ? C7 C8 C9 N1 -178.14(13) . . . . ? C3 C8 C9 N1 2.83(13) . . . . ? C7 C8 C3 C4 -0.37(19) . . . . ? C9 C8 C3 C4 178.81(12) . . . . ? C7 C8 C3 C2 179.59(11) . . . . ? C9 C8 C3 C2 -1.22(13) . . . . ? C9 N1 C2 O20 -177.24(12) . . . . ? C10 N1 C2 O20 -0.3(2) . . . . ? C9 N1 C2 C3 2.82(13) . . . . ? C10 N1 C2 C3 179.81(11) . . . . ? C4 C3 C2 O20 -0.8(2) . . . . ? C8 C3 C2 O20 179.19(14) . . . . ? C4 C3 C2 N1 179.09(13) . . . . ? C8 C3 C2 N1 -0.87(13) . . . . ? C13 O12 C11 O14 2.50(19) . . . . ? C13 O12 C11 C10 -176.20(12) . . . . ? C18 O17 C16 O19 2.7(2) . . . . ? C18 O17 C16 C15 -178.86(12) . . . . ? C9 C15 C16 O19 -10.7(3) . . . . ? C9 C15 C16 O17 170.93(12) . . . . ? C2 N1 C10 C11 115.04(13) . . . . ? C9 N1 C10 C11 -68.37(15) . . . . ? O14 C11 C10 N1 0.72(19) . . . . ? O12 C11 C10 N1 179.38(10) . . . . ? C8 C3 C4 C5 0.5(2) . . . . ? C2 C3 C4 C5 -179.50(13) . . . . ? C3 C8 C7 C6 -0.25(19) . . . . ? C9 C8 C7 C6 -179.18(13) . . . . ? C5 C6 C7 C8 0.8(2) . . . . ? C7 C6 C5 C4 -0.7(2) . . . . ? C3 C4 C5 C6 0.1(2) . . . . ?