#------------------------------------------------------------------------------ #$Date: 2020-04-24 03:51:16 +0300 (Fri, 24 Apr 2020) $ #$Revision: 251122 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/74/7157482.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_7157482 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 'C80 H56 N8 O40' _chemical_formula_weight 1769.32 _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_Hall '-C 2yc' _space_group_name_H-M_alt 'C 1 2/c 1' _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 90.00(3) _cell_angle_beta 105.62(3) _cell_angle_gamma 90.00(3) _cell_formula_units_Z 1 _cell_length_a 25.689(5) _cell_length_b 10.003(2) _cell_length_c 7.418(2) _cell_measurement_reflns_used 450 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 26.44 _cell_measurement_theta_min 1.646 _cell_volume 1835.8(8) _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 293(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.990 _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 0.0859 _diffrn_reflns_av_unetI/netI 0.0609 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.990 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_number 11385 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.990 _diffrn_reflns_theta_full 25.500 _diffrn_reflns_theta_max 26.440 _diffrn_reflns_theta_min 1.646 _diffrn_source 'fine-focus sealed tube' _exptl_absorpt_coefficient_mu 0.131 _exptl_absorpt_correction_T_max 0.992 _exptl_absorpt_correction_T_min 0.989 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details SADABS _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.600 _exptl_crystal_description needle _exptl_crystal_F_000 912 _exptl_crystal_size_max 0.11 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.266 _refine_diff_density_min -0.315 _refine_diff_density_rms 0.111 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 149 _refine_ls_number_reflns 1880 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.019 _refine_ls_R_factor_all 0.0910 _refine_ls_R_factor_gt 0.0536 _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^)+(0.0722P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1228 _refine_ls_wR_factor_ref 0.1473 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1152 _reflns_number_total 1880 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ob00557f2.cif _cod_data_source_block 9q _cod_original_sg_symbol_H-M 'C 2/c' _cod_database_code 7157482 _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 dm_br_NO2_a.res in C2/c CELL 0.71073 25.6886 10.0029 7.4181 90.000 105.621 90.000 ZERR 1.00 0.0050 0.0020 0.0020 0.030 0.030 0.030 LATT 7 SYMM - X, Y, 1/2 - Z SFAC C H N O UNIT 80 56 8 40 MERG 2 FMAP 2 PLAN 4 ACTA 51.00 BOND $H LIST 6 L.S. 10 WGHT 0.072200 FVAR 0.22992 O3 4 0.625076 0.012196 0.370033 11.00000 0.05119 0.03192 = 0.09053 -0.00186 0.03466 -0.00131 O4 4 0.525403 0.217085 0.479915 11.00000 0.04962 0.04229 = 0.09274 -0.00391 0.03888 -0.00165 O5 4 0.552122 -0.064822 0.444432 11.00000 0.05996 0.03653 = 0.10707 -0.00201 0.03882 -0.00927 N1 3 0.724331 0.617732 0.322058 11.00000 0.05689 0.04188 = 0.06335 0.00585 0.01682 -0.01206 O2 4 0.727750 0.735315 0.281604 11.00000 0.08383 0.04809 = 0.09671 0.01285 0.02907 -0.01892 O1 4 0.760725 0.538205 0.335678 11.00000 0.05932 0.06388 = 0.14836 0.02246 0.04787 0.00032 C5 1 0.617845 0.385250 0.386555 11.00000 0.04108 0.03243 = 0.04351 0.00005 0.01439 0.00017 C7 1 0.609218 0.241476 0.393381 11.00000 0.03956 0.03247 = 0.04952 0.00118 0.01521 0.00011 C6 1 0.665929 0.434052 0.360569 11.00000 0.04274 0.03724 = 0.04825 0.00250 0.01470 0.00078 AFIX 43 H6 2 0.692857 0.375407 0.348286 11.00000 -1.20000 AFIX 0 C9 1 0.569241 0.171850 0.433552 11.00000 0.03984 0.03525 = 0.05566 -0.00245 0.01819 0.00101 C10 1 0.579041 0.029268 0.419295 11.00000 0.04250 0.03880 = 0.06209 -0.00193 0.02029 -0.00274 C1 1 0.673376 0.570449 0.353144 11.00000 0.04957 0.03526 = 0.04755 0.00199 0.01578 -0.00551 C4 1 0.578299 0.477259 0.402614 11.00000 0.04771 0.03968 = 0.05570 0.00044 0.02081 0.00486 AFIX 43 H4 2 0.545778 0.446439 0.419480 11.00000 -1.20000 AFIX 0 C2 1 0.634953 0.661073 0.368544 11.00000 0.06414 0.03105 = 0.05561 0.00087 0.01958 0.00051 AFIX 43 H2 2 0.640905 0.752453 0.362265 11.00000 -1.20000 AFIX 0 C3 1 0.586793 0.612512 0.393835 11.00000 0.06401 0.03888 = 0.05940 0.00307 0.02554 0.01398 AFIX 43 H3 2 0.560019 0.672037 0.404946 11.00000 -1.20000 AFIX 0 C8 1 0.648163 0.142382 0.352546 11.00000 0.04739 0.03244 = 0.07553 0.00232 0.02585 -0.00113 AFIX 23 H8A 2 0.651980 0.155126 0.227105 11.00000 -1.20000 H8B 2 0.683412 0.151509 0.441336 11.00000 -1.20000 AFIX 0 H4A 2 0.505263 0.142226 0.499288 11.00000 0.10841 HKLF 4 REM dm_br_NO2_a.res in C2/c REM R1 = 0.0536 for 1152 Fo > 4sig(Fo) and 0.0910 for all 1880 data REM 149 parameters refined using 0 restraints END WGHT 0.0719 0.0000 REM Highest difference peak 0.266, deepest hole -0.315, 1-sigma level 0.111 Q1 1 0.5000 0.2549 0.2500 10.50000 0.05 0.27 Q2 1 0.5417 -0.0702 0.2075 11.00000 0.05 0.25 Q3 1 0.5795 0.3200 0.1917 11.00000 0.05 0.25 Q4 1 0.6510 0.0270 0.5915 11.00000 0.05 0.25 ; _shelx_res_checksum 80519 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -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 O3 O 0.62508(6) 0.01220(15) 0.3700(2) 0.0549(5) Uani 1 1 d . . . . . O4 O 0.52540(6) 0.21708(18) 0.4799(3) 0.0577(5) Uani 1 1 d . . . . . O5 O 0.55212(7) -0.06482(16) 0.4444(3) 0.0647(6) Uani 1 1 d . . . . . N1 N 0.72433(8) 0.6177(2) 0.3221(3) 0.0539(6) Uani 1 1 d . . . . . O2 O 0.72775(8) 0.73532(19) 0.2816(3) 0.0753(6) Uani 1 1 d . . . . . O1 O 0.76073(7) 0.5382(2) 0.3357(3) 0.0867(7) Uani 1 1 d . . . . . C5 C 0.61784(8) 0.3852(2) 0.3866(3) 0.0384(5) Uani 1 1 d . . . . . C7 C 0.60922(8) 0.2415(2) 0.3934(3) 0.0399(6) Uani 1 1 d . . . . . C6 C 0.66593(8) 0.4341(2) 0.3606(3) 0.0423(5) Uani 1 1 d . . . . . H6 H 0.6929 0.3754 0.3483 0.051 Uiso 1 1 calc R U . . . C9 C 0.56924(9) 0.1719(2) 0.4336(3) 0.0426(6) Uani 1 1 d . . . . . C10 C 0.57904(9) 0.0293(2) 0.4193(3) 0.0466(6) Uani 1 1 d . . . . . C1 C 0.67338(9) 0.5704(2) 0.3531(3) 0.0436(6) Uani 1 1 d . . . . . C4 C 0.57830(9) 0.4773(2) 0.4026(3) 0.0464(6) Uani 1 1 d . . . . . H4 H 0.5458 0.4464 0.4195 0.056 Uiso 1 1 calc R U . . . C2 C 0.63495(10) 0.6611(2) 0.3685(3) 0.0496(6) Uani 1 1 d . . . . . H2 H 0.6409 0.7525 0.3623 0.060 Uiso 1 1 calc R U . . . C3 C 0.58679(10) 0.6125(2) 0.3938(3) 0.0524(6) Uani 1 1 d . . . . . H3 H 0.5600 0.6720 0.4049 0.063 Uiso 1 1 calc R U . . . C8 C 0.64816(9) 0.1424(2) 0.3525(4) 0.0500(6) Uani 1 1 d . . . . . H8A H 0.6520 0.1551 0.2271 0.060 Uiso 1 1 calc R U . . . H8B H 0.6834 0.1515 0.4413 0.060 Uiso 1 1 calc R U . . . H4A H 0.5053(13) 0.142(3) 0.499(4) 0.108(12) 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 O3 0.0512(9) 0.0319(9) 0.0905(14) -0.0019(8) 0.0347(9) -0.0013(7) O4 0.0496(10) 0.0423(11) 0.0927(14) -0.0039(9) 0.0389(9) -0.0016(8) O5 0.0600(10) 0.0365(10) 0.1071(15) -0.0020(9) 0.0388(10) -0.0093(8) N1 0.0569(12) 0.0419(13) 0.0634(13) 0.0059(10) 0.0168(10) -0.0121(10) O2 0.0838(14) 0.0481(12) 0.0967(16) 0.0128(10) 0.0291(11) -0.0189(10) O1 0.0593(11) 0.0639(14) 0.148(2) 0.0225(13) 0.0479(12) 0.0003(10) C5 0.0411(11) 0.0324(12) 0.0435(12) 0.0000(9) 0.0144(9) 0.0002(9) C7 0.0396(11) 0.0325(13) 0.0495(14) 0.0012(10) 0.0152(10) 0.0001(9) C6 0.0427(11) 0.0372(13) 0.0483(13) 0.0025(10) 0.0147(10) 0.0008(10) C9 0.0398(11) 0.0353(13) 0.0557(14) -0.0024(10) 0.0182(10) 0.0010(10) C10 0.0425(12) 0.0388(13) 0.0621(15) -0.0019(11) 0.0203(11) -0.0027(10) C1 0.0496(12) 0.0353(13) 0.0476(13) 0.0020(10) 0.0158(10) -0.0055(10) C4 0.0477(12) 0.0397(13) 0.0557(14) 0.0004(11) 0.0208(10) 0.0049(10) C2 0.0641(15) 0.0310(13) 0.0556(15) 0.0009(10) 0.0196(12) 0.0005(11) C3 0.0640(14) 0.0389(14) 0.0594(15) 0.0031(12) 0.0255(12) 0.0140(11) C8 0.0474(12) 0.0324(13) 0.0755(17) 0.0023(12) 0.0259(12) -0.0011(10) 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 C10 O3 C8 108.79(17) . . ? C9 O4 H4A 108(2) . . ? O1 N1 O2 123.2(2) . . ? O1 N1 C1 118.5(2) . . ? O2 N1 C1 118.3(2) . . ? C6 C5 C4 118.3(2) . . ? C6 C5 C7 120.04(19) . . ? C4 C5 C7 121.68(19) . . ? C9 C7 C5 130.81(19) . . ? C9 C7 C8 107.17(19) . . ? C5 C7 C8 122.02(18) . . ? C1 C6 C5 119.4(2) . . ? C1 C6 H6 120.3 . . ? C5 C6 H6 120.3 . . ? C7 C9 O4 128.9(2) . . ? C7 C9 C10 109.6(2) . . ? O4 C9 C10 121.5(2) . . ? O5 C10 O3 121.7(2) . . ? O5 C10 C9 129.2(2) . . ? O3 C10 C9 109.1(2) . . ? C2 C1 C6 122.7(2) . . ? C2 C1 N1 119.6(2) . . ? C6 C1 N1 117.6(2) . . ? C3 C4 C5 121.0(2) . . ? C3 C4 H4 119.5 . . ? C5 C4 H4 119.5 . . ? C1 C2 C3 118.0(2) . . ? C1 C2 H2 121.0 . . ? C3 C2 H2 121.0 . . ? C4 C3 C2 120.6(2) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? O3 C8 C7 105.35(17) . . ? O3 C8 H8A 110.7 . . ? C7 C8 H8A 110.7 . . ? O3 C8 H8B 110.7 . . ? C7 C8 H8B 110.7 . . ? H8A C8 H8B 108.8 . . ? 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 O3 C10 1.339(3) . ? O3 C8 1.451(3) . ? O4 C9 1.342(3) . ? O4 H4A 0.94(3) . ? O5 C10 1.212(3) . ? N1 O1 1.211(3) . ? N1 O2 1.223(3) . ? N1 C1 1.467(3) . ? C5 C6 1.389(3) . ? C5 C4 1.399(3) . ? C5 C7 1.458(3) . ? C7 C9 1.339(3) . ? C7 C8 1.496(3) . ? C6 C1 1.381(3) . ? C6 H6 0.9300 . ? C9 C10 1.457(3) . ? C1 C2 1.367(3) . ? C4 C3 1.375(3) . ? C4 H4 0.9300 . ? C2 C3 1.388(4) . ? C2 H2 0.9300 . ? C3 H3 0.9300 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ?