#------------------------------------------------------------------------------ #$Date: 2024-12-03 02:38:15 +0200 (Tue, 03 Dec 2024) $ #$Revision: 296189 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/96/7249662.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_7249662 loop_ _publ_author_name 'Yuan, Yong' 'Liu, Xincong' 'Zhang, Feng' 'Bai, Chunyan' 'Tao, Yuyan' 'Bao, Xiazhen' 'Ji, Dongsheng' 'Huo, Congde' _publ_section_title ; Electrochemical dehydrogenative annulation for the synthesis of 4-oxo-oxazolines ; _journal_name_full 'Green Chemistry' _journal_paper_doi 10.1039/D4GC05119J _journal_year 2024 _chemical_formula_moiety 'C10 H11 N O2' _chemical_formula_sum 'C10 H11 N O2' _chemical_formula_weight 177.20 _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 _atom_sites_solution_primary dual _audit_creation_date 2023-09-21 _audit_creation_method ; Olex2 1.5-ac5-024 (compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498) ; _audit_update_record ; 2024-08-02 deposited with the CCDC. 2024-11-26 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90.820(6) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 15.5314(9) _cell_length_b 4.1737(2) _cell_length_c 14.2425(9) _cell_measurement_reflns_used 2646 _cell_measurement_temperature 304.23(10) _cell_measurement_theta_max 30.6690 _cell_measurement_theta_min 2.6100 _cell_volume 923.15(9) _computing_cell_refinement 'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)' _computing_data_collection 'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)' _computing_data_reduction 'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)' _computing_molecular_graphics 'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT (Sheldrick, 2015)' _diffrn_ambient_environment air _diffrn_ambient_temperature 304.23(10) _diffrn_detector 'Hybrid Pixel Array Detector' _diffrn_detector_area_resol_mean 10.0000 _diffrn_detector_type HyPix _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.828 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w -19.00 61.00 1.00 2.00 -- -6.19 5.00 124.00 80 2 \w 2.00 32.00 1.00 2.00 -- 4.16 -99.00 -30.00 30 3 \w -61.00 9.00 1.00 2.00 -- -6.19 -57.00 -90.00 70 4 \w -75.00 -50.00 1.00 2.00 -- -6.19 -5.00 -52.00 25 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Synergy R, DW system, HyPix' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0405773000 _diffrn_orient_matrix_UB_12 0.0085642000 _diffrn_orient_matrix_UB_13 -0.0221099000 _diffrn_orient_matrix_UB_21 0.0207949000 _diffrn_orient_matrix_UB_22 0.0065127000 _diffrn_orient_matrix_UB_23 0.0446202000 _diffrn_orient_matrix_UB_31 0.0028575000 _diffrn_orient_matrix_UB_32 -0.1696396000 _diffrn_orient_matrix_UB_33 0.0005967000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0188 _diffrn_reflns_av_unetI/netI 0.0230 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.828 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 7692 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.828 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 30.382 _diffrn_reflns_theta_min 2.623 _diffrn_source 'Rotating-anode X-ray tube' _diffrn_source_type 'Rigaku (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.90328 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.42.93a (Rigaku Oxford Diffraction, 2023) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.275 _exptl_crystal_description needle _exptl_crystal_F_000 376 _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.11 _refine_diff_density_max 0.168 _refine_diff_density_min -0.153 _refine_diff_density_rms 0.037 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 120 _refine_ls_number_reflns 2294 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.021 _refine_ls_R_factor_all 0.0707 _refine_ls_R_factor_gt 0.0455 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0703P)^2^+0.1315P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1235 _refine_ls_wR_factor_ref 0.1446 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1515 _reflns_number_total 2294 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4gc05119j2.cif _cod_data_source_block liuxc_0921_auto _cod_original_cell_volume 923.14(10) _cod_database_code 7249662 _shelx_shelxl_version_number 2018/3 _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_estimated_absorpt_t_max 0.990 _shelx_estimated_absorpt_t_min 0.976 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups, All O(H) groups 2.a Ternary CH refined with riding coordinates: C10(H10) 2.b Secondary CH2 refined with riding coordinates: C9(H9A,H9B) 2.c Aromatic/amide H refined with riding coordinates: C2(H2A), C3(H3), C5(H5), C6(H6) 2.d Idealised Me refined as rotating group: C7(H7A,H7B,H7C) 2.e Idealised tetrahedral OH refined as rotating group: O2(H2) ; _shelx_res_file ; TITL liuxc_0921_auto_a.res in P2(1)/c liuxc_0921_auto.res created by SHELXL-2018/3 at 10:13:14 on 21-Sep-2023 REM Old TITL liuxc_0921_auto in P2(1)/c REM SHELXT solution in P2(1)/c: R1 0.175, Rweak 0.260, Alpha 0.018 REM 0.273 for 237 systematic absences, Orientation as input REM Formula found by SHELXT: C10 N O2 CELL 0.71073 15.531359 4.173675 14.242453 90 90.8201 90 ZERR 4 0.000943 0.000236 0.000932 0 0.0055 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H N O UNIT 40 44 4 8 L.S. 4 0 0 PLAN 2 SIZE 0.11 0.13 0.27 TEMP 31 BOND list 4 fmap 2 53 ACTA REM REM REM WGHT 0.070300 0.131500 FVAR 5.71035 O1 4 0.317471 0.177842 0.664537 11.00000 0.06118 0.08523 = 0.05034 0.00327 0.00780 0.01292 O2 4 0.522007 0.106300 0.628982 11.00000 0.05218 0.07823 = 0.05766 -0.01638 -0.00271 0.00154 AFIX 147 H2 2 0.552330 0.074133 0.583274 11.00000 -1.50000 AFIX 0 N1 3 0.394674 0.036936 0.538757 11.00000 0.04699 0.06588 = 0.05407 -0.01197 -0.00160 0.00120 C1 1 0.260500 0.335241 0.514972 11.00000 0.04333 0.05561 = 0.05618 -0.00388 0.00413 -0.00280 C2 1 0.267186 0.354353 0.418527 11.00000 0.05227 0.09160 = 0.05822 -0.00072 0.00589 0.00910 AFIX 43 H2A 2 0.314950 0.267408 0.389237 11.00000 -1.20000 AFIX 0 C3 1 0.203706 0.501133 0.365276 11.00000 0.06357 0.09658 = 0.06154 0.00713 -0.00177 0.00414 AFIX 43 H3 2 0.209313 0.510961 0.300416 11.00000 -1.20000 AFIX 0 C4 1 0.132000 0.633807 0.406233 11.00000 0.05283 0.06382 = 0.07971 -0.00072 -0.00933 -0.00213 C5 1 0.125804 0.614945 0.502300 11.00000 0.04941 0.07843 = 0.08777 -0.01094 0.00341 0.01056 AFIX 43 H5 2 0.078065 0.702806 0.531410 11.00000 -1.20000 AFIX 0 C6 1 0.188960 0.468262 0.556629 11.00000 0.05612 0.07701 = 0.06283 -0.00696 0.00638 0.00640 AFIX 43 H6 2 0.183291 0.459037 0.621489 11.00000 -1.20000 AFIX 0 C7 1 0.062745 0.792178 0.346876 11.00000 0.07035 0.08710 = 0.11171 0.00402 -0.02232 0.00897 AFIX 137 H7A 2 0.008448 0.775078 0.377858 11.00000 -1.50000 H7B 2 0.059016 0.687963 0.286867 11.00000 -1.50000 H7C 2 0.076763 1.014127 0.338187 11.00000 -1.50000 AFIX 0 C8 1 0.327929 0.174976 0.570465 11.00000 0.04785 0.05488 = 0.04969 -0.00520 0.00364 -0.00390 C9 1 0.388696 -0.005337 0.703551 11.00000 0.06299 0.08074 = 0.05805 0.00871 0.00002 0.00637 AFIX 23 H9A 2 0.368530 -0.203697 0.731095 11.00000 -1.20000 H9B 2 0.419414 0.116951 0.751278 11.00000 -1.20000 AFIX 0 C10 1 0.446078 -0.071941 0.619992 11.00000 0.05484 0.05729 = 0.05959 -0.00547 -0.00418 0.00433 AFIX 13 H10 2 0.458839 -0.301245 0.615130 11.00000 -1.20000 AFIX 0 HKLF 4 REM liuxc_0921_auto_a.res in P2(1)/c REM wR2 = 0.1446, GooF = S = 1.021, Restrained GooF = 1.021 for all data REM R1 = 0.0455 for 1515 Fo > 4sig(Fo) and 0.0707 for all 2294 data REM 120 parameters refined using 0 restraints END WGHT 0.0703 0.1315 REM Highest difference peak 0.168, deepest hole -0.153, 1-sigma level 0.037 Q1 1 0.0347 0.9910 0.3874 11.00000 0.05 0.17 Q2 1 0.0149 0.6414 0.3259 11.00000 0.05 0.16 ; _shelx_res_checksum 23784 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.151 _oxdiff_exptl_absorpt_empirical_full_min 0.787 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 O1 O 0.31747(7) 0.1778(3) 0.66454(7) 0.0655(3) Uani 1 1 d . . . . . O2 O 0.52201(6) 0.1063(3) 0.62898(7) 0.0627(3) Uani 1 1 d . . . . . H2 H 0.552330 0.074133 0.583274 0.094 Uiso 1 1 calc R U . . . N1 N 0.39467(7) 0.0369(3) 0.53876(8) 0.0557(3) Uani 1 1 d . . . . . C1 C 0.26050(9) 0.3352(3) 0.51497(10) 0.0517(4) Uani 1 1 d . . . . . C2 C 0.26719(10) 0.3544(4) 0.41853(11) 0.0673(4) Uani 1 1 d . . . . . H2A H 0.314950 0.267408 0.389237 0.081 Uiso 1 1 calc R U . . . C3 C 0.20371(11) 0.5011(5) 0.36528(12) 0.0739(5) Uani 1 1 d . . . . . H3 H 0.209313 0.510961 0.300416 0.089 Uiso 1 1 calc R U . . . C4 C 0.13200(10) 0.6338(4) 0.40623(13) 0.0656(4) Uani 1 1 d . . . . . C5 C 0.12580(10) 0.6149(4) 0.50230(13) 0.0718(5) Uani 1 1 d . . . . . H5 H 0.078065 0.702806 0.531410 0.086 Uiso 1 1 calc R U . . . C6 C 0.18896(10) 0.4683(4) 0.55663(12) 0.0653(4) Uani 1 1 d . . . . . H6 H 0.183291 0.459037 0.621489 0.078 Uiso 1 1 calc R U . . . C7 C 0.06274(13) 0.7922(5) 0.34688(15) 0.0899(6) Uani 1 1 d . . . . . H7A H 0.008448 0.775078 0.377858 0.135 Uiso 1 1 calc R U . . . H7B H 0.059016 0.687963 0.286867 0.135 Uiso 1 1 calc R U . . . H7C H 0.076763 1.014127 0.338187 0.135 Uiso 1 1 calc R U . . . C8 C 0.32793(9) 0.1750(3) 0.57046(9) 0.0508(3) Uani 1 1 d . . . . . C9 C 0.38870(11) -0.0053(5) 0.70355(12) 0.0673(4) Uani 1 1 d . . . . . H9A H 0.368530 -0.203697 0.731095 0.081 Uiso 1 1 calc R U . . . H9B H 0.419414 0.116951 0.751278 0.081 Uiso 1 1 calc R U . . . C10 C 0.44608(10) -0.0719(4) 0.61999(10) 0.0573(4) Uani 1 1 d . . . . . H10 H 0.458839 -0.301245 0.615130 0.069 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 O1 0.0612(6) 0.0852(8) 0.0503(6) 0.0033(5) 0.0078(5) 0.0129(5) O2 0.0522(6) 0.0782(7) 0.0577(6) -0.0164(5) -0.0027(5) 0.0015(5) N1 0.0470(7) 0.0659(7) 0.0541(7) -0.0120(5) -0.0016(5) 0.0012(5) C1 0.0433(7) 0.0556(8) 0.0562(8) -0.0039(6) 0.0041(6) -0.0028(6) C2 0.0523(9) 0.0916(12) 0.0582(9) -0.0007(8) 0.0059(7) 0.0091(8) C3 0.0636(10) 0.0966(13) 0.0615(10) 0.0071(9) -0.0018(8) 0.0041(9) C4 0.0528(9) 0.0638(9) 0.0797(11) -0.0007(8) -0.0093(8) -0.0021(7) C5 0.0494(9) 0.0784(11) 0.0878(12) -0.0109(9) 0.0034(8) 0.0106(8) C6 0.0561(9) 0.0770(10) 0.0628(9) -0.0070(8) 0.0064(7) 0.0064(8) C7 0.0703(12) 0.0871(13) 0.1117(16) 0.0040(11) -0.0223(11) 0.0090(10) C8 0.0478(7) 0.0549(8) 0.0497(7) -0.0052(6) 0.0036(6) -0.0039(6) C9 0.0630(9) 0.0807(11) 0.0580(9) 0.0087(8) 0.0000(7) 0.0064(8) C10 0.0548(8) 0.0573(8) 0.0596(9) -0.0055(6) -0.0042(6) 0.0043(6) 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 C8 O1 C9 105.87(11) . . ? C8 N1 C10 107.25(12) . . ? C2 C1 C6 118.40(14) . . ? C2 C1 C8 119.98(13) . . ? C6 C1 C8 121.62(13) . . ? C3 C2 C1 120.62(15) . . ? C2 C3 C4 121.37(16) . . ? C3 C4 C7 120.75(17) . . ? C5 C4 C3 117.76(15) . . ? C5 C4 C7 121.49(16) . . ? C4 C5 C6 121.51(15) . . ? C1 C6 C5 120.34(15) . . ? O1 C8 C1 115.82(12) . . ? N1 C8 O1 117.72(13) . . ? N1 C8 C1 126.46(13) . . ? O1 C9 C10 104.41(12) . . ? O2 C10 N1 110.84(13) . . ? O2 C10 C9 109.48(12) . . ? N1 C10 C9 103.98(12) . . ? 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 C8 1.3520(16) . ? O1 C9 1.4489(18) . ? O2 C10 1.3986(18) . ? N1 C8 1.2743(17) . ? N1 C10 1.4684(19) . ? C1 C2 1.381(2) . ? C1 C6 1.383(2) . ? C1 C8 1.465(2) . ? C2 C3 1.379(2) . ? C3 C4 1.381(2) . ? C4 C5 1.375(2) . ? C4 C7 1.511(2) . ? C5 C6 1.383(2) . ? C9 C10 1.523(2) . ?