#------------------------------------------------------------------------------ #$Date: 2024-02-04 14:17:03 +0200 (Sun, 04 Feb 2024) $ #$Revision: 289568 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/78/7247857.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_7247857 loop_ _publ_author_name 'Qi, Jing' 'Wang, Xiyan' 'Wang, Gan' 'Dubbaka, Srinivas Reddy' 'O'Neill, Patrick' 'Ang, Hwee Ting' 'Wu, Jie' _publ_section_title ; Sustainable electrocatalytic oxidation of N-alkylamides to acyclic imides using H2O ; _journal_issue 1 _journal_name_full 'Green Chemistry' _journal_page_first 306 _journal_page_last 311 _journal_paper_doi 10.1039/D3GC04010K _journal_volume 26 _journal_year 2024 _chemical_formula_sum 'C9 H6 N2 O2' _chemical_formula_weight 174.16 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary 'Dual Space' _audit_creation_method SHELXL-2019/1 _audit_update_record ; 2023-07-10 deposited with the CCDC. 2023-12-05 downloaded from the CCDC. ; _cell_angle_alpha 94.101(2) _cell_angle_beta 93.691(2) _cell_angle_gamma 96.948(2) _cell_formula_units_Z 2 _cell_length_a 3.7781(2) _cell_length_b 7.5804(3) _cell_length_c 14.7776(6) _cell_measurement_reflns_used 5946 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 29.51 _cell_measurement_theta_min 2.72 _cell_volume 417.90(3) _computing_cell_refinement 'APEX4 v2021.10-1 (Bruker AXS)' _computing_data_collection 'APEX4 (Bruker AXS)' _computing_data_reduction 'SAINT V8.32B (Bruker AXS Inc., 2014)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL--2014 (Sheldrick 2014)' _computing_structure_solution 'SHELXT--(Sheldrick 2015)' _diffrn_ambient_temperature 100(2) _diffrn_measured_fraction_theta_full 0.990 _diffrn_measured_fraction_theta_max 0.990 _diffrn_measurement_device_type 'Bruker D8 Venture' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0421 _diffrn_reflns_av_unetI/netI 0.0267 _diffrn_reflns_Laue_measured_fraction_full 0.990 _diffrn_reflns_Laue_measured_fraction_max 0.990 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 11723 _diffrn_reflns_point_group_measured_fraction_full 0.990 _diffrn_reflns_point_group_measured_fraction_max 0.990 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 29.553 _diffrn_reflns_theta_min 3.723 _diffrn_source 'Microfocus Sealed Tube' _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_T_max 0.7459 _exptl_absorpt_correction_T_min 0.7132 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0870 before and 0.0486 after correction. The Ratio of minimum to maximum transmission is 0.9562. The \l/2 correction factor is Not present. ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.384 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'Not Measured' _exptl_crystal_description needle _exptl_crystal_F_000 180 _exptl_crystal_size_max 0.188 _exptl_crystal_size_mid 0.117 _exptl_crystal_size_min 0.099 _refine_diff_density_max 0.449 _refine_diff_density_min -0.196 _refine_diff_density_rms 0.049 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 122 _refine_ls_number_reflns 2329 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.055 _refine_ls_R_factor_all 0.0419 _refine_ls_R_factor_gt 0.0385 _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^)+(0.0672P)^2^+0.0785P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1091 _refine_ls_wR_factor_ref 0.1135 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2110 _reflns_number_total 2329 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3gc04010k2.cif _cod_data_source_block M266 _cod_depositor_comments ; The following automatic conversions were performed: data item '_exptl_absorpt_correction_type' value 'Multi-scan' was changed to 'multi-scan' in accordance with the /home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 last updated on 2011-04-26. data item '_exptl_crystal_density_meas' value 'Not Measured' was changed to '?' -- the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas Adding full bibliography for 7247857.cif. ; _cod_database_code 7247857 _shelx_shelxl_version_number 2019/1 _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. ; _computing_bruker_data_scaling 'SADABS V2016/2 (Bruker AXS Inc.)' _shelx_res_file ; TITL M266_a.res in P-1 M266.res created by SHELXL-2019/1 at 11:19:08 on 17-Aug-2022 CELL 0.71073 3.7781 7.5804 14.7776 94.101 93.691 96.948 ZERR 2.000 0.0002 0.0003 0.0006 0.002 0.002 0.002 LATT 1 SFAC C H N O UNIT 18 12 4 4 OMIT 0 -1 1 OMIT 0 1 0 OMIT 0 -3 3 OMIT 0 1 1 ACTA LIST 4 TEMP -173.150 L.S. 10 BOND FMAP 2 CONF HTAB EQIV $1 -x+1, -y, -z+1 HTAB N1 O1_$1 EQIV $2 -x, -y+1, -z+1 HTAB C1 O2_$2 BOND $H PLAN 20 WGHT 0.067200 0.078500 FVAR 0.32749 O1 4 0.280299 0.110386 0.582594 11.00000 0.03087 0.01943 = 0.02097 0.00363 0.00782 0.00898 O2 4 0.225414 0.474535 0.404938 11.00000 0.02514 0.01793 = 0.02176 0.00068 0.00423 0.00864 N1 3 0.373658 0.206217 0.442710 11.00000 0.02080 0.01500 = 0.01868 0.00067 0.00494 0.00593 N2 3 0.922713 0.222640 -0.045242 11.00000 0.03307 0.03389 = 0.02436 0.00077 0.00810 0.00064 H1 2 0.473531 0.108359 0.427928 11.00000 0.03308 C1 1 0.248915 0.221427 0.527846 11.00000 0.01850 0.01625 = 0.01888 -0.00037 0.00375 0.00406 AFIX 43 H1A 2 0.133854 0.322274 0.544698 11.00000 -1.20000 AFIX 0 C2 1 0.346165 0.337389 0.382747 11.00000 0.01490 0.01582 = 0.01852 0.00011 0.00118 0.00242 C3 1 0.472109 0.302881 0.290142 11.00000 0.01492 0.01898 = 0.01713 0.00033 0.00167 0.00365 C4 1 0.522558 0.133840 0.253574 11.00000 0.02185 0.01900 = 0.01822 0.00073 0.00199 0.00412 AFIX 43 H4 2 0.478497 0.033704 0.288248 11.00000 -1.20000 AFIX 0 C5 1 0.637233 0.111612 0.166452 11.00000 0.02209 0.02203 = 0.01943 -0.00222 0.00203 0.00466 AFIX 43 H5 2 0.671529 -0.003352 0.141204 11.00000 -1.20000 AFIX 0 C6 1 0.701314 0.260003 0.116570 11.00000 0.01685 0.02709 = 0.01806 0.00059 0.00242 0.00226 C7 1 0.650917 0.429849 0.152507 11.00000 0.02585 0.02381 = 0.02153 0.00473 0.00537 0.00283 AFIX 43 H7 2 0.695283 0.530046 0.117889 11.00000 -1.20000 AFIX 0 C8 1 0.535393 0.450324 0.239287 11.00000 0.02389 0.01916 = 0.02196 0.00157 0.00424 0.00420 AFIX 43 H8 2 0.499078 0.565149 0.264301 11.00000 -1.20000 AFIX 0 C9 1 0.823785 0.238277 0.026365 11.00000 0.02283 0.02791 = 0.02226 0.00092 0.00302 0.00181 HKLF 4 REM M266_a.res in P-1 REM wR2 = 0.1135, GooF = S = 1.055, Restrained GooF = 1.055 for all data REM R1 = 0.0385 for 2110 Fo > 4sig(Fo) and 0.0419 for all 2329 data REM 122 parameters refined using 0 restraints END WGHT 0.0673 0.0784 REM Instructions for potential hydrogen bonds HTAB N1 O1_$1 HTAB C1 O2_$2 REM Highest difference peak 0.449, deepest hole -0.196, 1-sigma level 0.049 Q1 1 0.4232 0.3200 0.3365 11.00000 0.05 0.45 Q2 1 0.6097 0.4379 0.1966 11.00000 0.05 0.41 Q3 1 0.6692 0.1874 0.1392 11.00000 0.05 0.39 Q4 1 0.3236 0.2190 0.4824 11.00000 0.05 0.37 Q5 1 0.5005 0.3719 0.2625 11.00000 0.05 0.35 Q6 1 0.5087 0.2211 0.2761 11.00000 0.05 0.35 Q7 1 0.6177 0.1345 0.2124 11.00000 0.05 0.34 Q8 1 0.6880 0.3397 0.1367 11.00000 0.05 0.33 Q9 1 0.3634 0.2680 0.4169 11.00000 0.05 0.27 Q10 1 0.7359 0.2475 0.0708 11.00000 0.05 0.24 Q11 1 0.3024 0.1594 0.5605 11.00000 0.05 0.21 Q12 1 0.8165 0.2819 -0.0180 11.00000 0.05 0.18 Q13 1 0.9738 0.2827 0.0043 11.00000 0.05 0.18 Q14 1 0.1993 0.4013 0.3873 11.00000 0.05 0.18 Q15 1 0.8532 0.1665 -0.0059 11.00000 0.05 0.17 Q16 1 0.7626 0.2090 -0.0125 11.00000 0.05 0.17 Q17 1 0.4480 0.1780 0.4427 11.00000 0.05 0.16 Q18 1 0.0824 0.4587 0.4364 11.00000 0.05 0.14 Q19 1 0.1213 0.4963 0.3731 11.00000 0.05 0.13 Q20 1 0.5334 0.1286 0.6010 11.00000 0.05 0.12 ; _shelx_res_checksum 66244 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' 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 0.28030(19) 0.11039(9) 0.58259(5) 0.02292(17) Uani 1 1 d . . . . . O2 O 0.22541(17) 0.47454(8) 0.40494(4) 0.02106(17) Uani 1 1 d . . . . . N1 N 0.3737(2) 0.20622(10) 0.44271(5) 0.01774(17) Uani 1 1 d . . . . . N2 N 0.9227(3) 0.22264(13) -0.04524(6) 0.0306(2) Uani 1 1 d . . . . . H1 H 0.474(4) 0.108(2) 0.4279(10) 0.033(3) Uiso 1 1 d . . . . . C1 C 0.2489(2) 0.22143(11) 0.52785(6) 0.01771(18) Uani 1 1 d . . . . . H1A H 0.133854 0.322274 0.544698 0.021 Uiso 1 1 calc R U . . . C2 C 0.3462(2) 0.33739(11) 0.38275(6) 0.01644(18) Uani 1 1 d . . . . . C3 C 0.4721(2) 0.30288(11) 0.29014(6) 0.01692(18) Uani 1 1 d . . . . . C4 C 0.5226(2) 0.13384(12) 0.25357(6) 0.01958(19) Uani 1 1 d . . . . . H4 H 0.478497 0.033704 0.288248 0.023 Uiso 1 1 calc R U . . . C5 C 0.6372(2) 0.11161(12) 0.16645(6) 0.0212(2) Uani 1 1 d . . . . . H5 H 0.671529 -0.003352 0.141204 0.025 Uiso 1 1 calc R U . . . C6 C 0.7013(2) 0.26000(13) 0.11657(6) 0.0207(2) Uani 1 1 d . . . . . C7 C 0.6509(3) 0.42985(13) 0.15251(6) 0.0235(2) Uani 1 1 d . . . . . H7 H 0.695283 0.530046 0.117889 0.028 Uiso 1 1 calc R U . . . C8 C 0.5354(2) 0.45032(12) 0.23929(6) 0.0214(2) Uani 1 1 d . . . . . H8 H 0.499078 0.565149 0.264301 0.026 Uiso 1 1 calc R U . . . C9 C 0.8238(3) 0.23828(13) 0.02636(7) 0.0244(2) 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 O1 0.0309(4) 0.0194(3) 0.0210(3) 0.0036(2) 0.0078(3) 0.0090(3) O2 0.0251(3) 0.0179(3) 0.0218(3) 0.0007(2) 0.0042(2) 0.0086(2) N1 0.0208(4) 0.0150(3) 0.0187(4) 0.0007(3) 0.0049(3) 0.0059(3) N2 0.0331(5) 0.0339(5) 0.0244(4) 0.0008(3) 0.0081(3) 0.0006(4) C1 0.0185(4) 0.0162(4) 0.0189(4) -0.0004(3) 0.0038(3) 0.0041(3) C2 0.0149(4) 0.0158(4) 0.0185(4) 0.0001(3) 0.0012(3) 0.0024(3) C3 0.0149(4) 0.0190(4) 0.0171(4) 0.0003(3) 0.0017(3) 0.0036(3) C4 0.0218(4) 0.0190(4) 0.0182(4) 0.0007(3) 0.0020(3) 0.0041(3) C5 0.0221(4) 0.0220(4) 0.0194(4) -0.0022(3) 0.0020(3) 0.0047(3) C6 0.0169(4) 0.0271(5) 0.0181(4) 0.0006(3) 0.0024(3) 0.0023(3) C7 0.0258(4) 0.0238(4) 0.0215(4) 0.0047(3) 0.0054(3) 0.0028(3) C8 0.0239(4) 0.0192(4) 0.0220(4) 0.0016(3) 0.0042(3) 0.0042(3) C9 0.0228(4) 0.0279(5) 0.0223(4) 0.0009(3) 0.0030(3) 0.0018(4) 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 C1 N1 C2 121.44(7) . . ? C1 N1 H1 116.9(9) . . ? C2 N1 H1 121.7(9) . . ? O1 C1 N1 122.48(8) . . ? O1 C1 H1A 118.8 . . ? N1 C1 H1A 118.8 . . ? O2 C2 N1 121.30(8) . . ? O2 C2 C3 121.67(8) . . ? N1 C2 C3 117.03(7) . . ? C4 C3 C8 120.14(8) . . ? C4 C3 C2 123.30(8) . . ? C8 C3 C2 116.56(8) . . ? C5 C4 C3 120.09(8) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C4 C5 C6 119.21(8) . . ? C4 C5 H5 120.4 . . ? C6 C5 H5 120.4 . . ? C5 C6 C7 121.14(8) . . ? C5 C6 C9 119.55(8) . . ? C7 C6 C9 119.31(8) . . ? C8 C7 C6 119.14(8) . . ? C8 C7 H7 120.4 . . ? C6 C7 H7 120.4 . . ? C7 C8 C3 120.27(8) . . ? C7 C8 H8 119.9 . . ? C3 C8 H8 119.9 . . ? N2 C9 C6 179.35(11) . . ? 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 C1 1.2192(11) . ? O2 C2 1.2173(10) . ? N1 C1 1.3737(11) . ? N1 C2 1.3870(11) . ? N1 H1 0.892(15) . ? N2 C9 1.1477(13) . ? C1 H1A 0.9500 . ? C2 C3 1.4934(12) . ? C3 C4 1.3941(12) . ? C3 C8 1.3963(12) . ? C4 C5 1.3900(12) . ? C4 H4 0.9500 . ? C5 C6 1.3939(13) . ? C5 H5 0.9500 . ? C6 C7 1.3966(13) . ? C6 C9 1.4438(12) . ? C7 C8 1.3853(12) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? 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 _geom_hbond_publ_flag N1 H1 O1 0.892(15) 1.998(15) 2.8814(10) 170.3(13) 2_656 yes C1 H1A O2 0.95 2.29 3.2266(10) 168.9 2_566 yes 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 N1 C1 O1 -177.69(8) . . . . ? C1 N1 C2 O2 3.43(13) . . . . ? C1 N1 C2 C3 -176.74(7) . . . . ? O2 C2 C3 C4 -162.53(9) . . . . ? N1 C2 C3 C4 17.64(12) . . . . ? O2 C2 C3 C8 16.66(12) . . . . ? N1 C2 C3 C8 -163.17(8) . . . . ? C8 C3 C4 C5 0.22(13) . . . . ? C2 C3 C4 C5 179.38(8) . . . . ? C3 C4 C5 C6 0.12(13) . . . . ? C4 C5 C6 C7 -0.25(14) . . . . ? C4 C5 C6 C9 179.41(8) . . . . ? C5 C6 C7 C8 0.04(14) . . . . ? C9 C6 C7 C8 -179.62(8) . . . . ? C6 C7 C8 C3 0.31(14) . . . . ? C4 C3 C8 C7 -0.44(14) . . . . ? C2 C3 C8 C7 -179.66(8) . . . . ?