#------------------------------------------------------------------------------ #$Date: 2015-12-09 13:49:30 +0200 (Wed, 09 Dec 2015) $ #$Revision: 170976 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/53/10/1531042.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_1531042 loop_ _publ_author_name 'Gazi, Sarifuddin' 'Hung Ng, Wilson Kwok' 'Ganguly, Rakesh' 'Putra Moeljadi, Adhitya Mangala' 'Hirao, Hajime' 'Soo, Han Sen' _publ_section_title ; Selective photocatalytic C--C bond cleavage under ambient conditions with earth abundant vanadium complexes ; _journal_issue 12 _journal_name_full 'Chem. Sci.' _journal_page_first 7130 _journal_paper_doi 10.1039/C5SC02923F _journal_volume 6 _journal_year 2015 _chemical_formula_sum 'C15 H22 N O4 V' _chemical_formula_weight 331.27 _chemical_properties_physical 'Light-sensitive, Photo-sensitive' _space_group_crystal_system orthorhombic _space_group_IT_number 33 _space_group_name_Hall 'P 2c -2n' _space_group_name_H-M_alt 'P n a 21' _symmetry_space_group_name_Hall 'P 2c -2n' _symmetry_space_group_name_H-M 'P n a 21' _atom_sites_solution_hydrogens geom _audit_update_record ; 2015-04-10 deposited with the CCDC. 2015-09-14 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 14.7897(4) _cell_length_b 13.1867(3) _cell_length_c 7.8841(2) _cell_measurement_reflns_used 5799 _cell_measurement_temperature 103.(2) _cell_measurement_theta_max 31.0564 _cell_measurement_theta_min 2.7544 _cell_volume 1537.62(7) _computing_cell_refinement 'SAINT V8.34A (Bruker AXS Inc., 2013)' _computing_data_collection 'APEX2 (Bruker AXS Inc., 2014)' _computing_data_reduction 'SAINT V8.34A (Bruker AXS Inc., 2013)' _computing_molecular_graphics 'XP (Bruker AXS Inc., 2014)' _computing_publication_material 'APEX2 (Bruker AXS Inc., 2014)' _computing_structure_refinement 'SHELXL-2014 (Sheldrick, 2014)' _diffrn_ambient_temperature 103.(2) _diffrn_detector_area_resol_mean 8.3333 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0265 _diffrn_reflns_av_unetI/netI 0.0377 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 12950 _diffrn_reflns_theta_full 31.07 _diffrn_reflns_theta_max 31.07 _diffrn_reflns_theta_min 2.75 _diffrn_source 'fine-focus sealed tube' _exptl_absorpt_coefficient_mu 0.660 _exptl_absorpt_correction_T_max 0.88 _exptl_absorpt_correction_T_min 0.72 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2014/3 (Bruker AXS Inc.)' _exptl_crystal_colour red _exptl_crystal_density_diffrn 1.431 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 696 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: methanol' _exptl_crystal_size_max 0.420 _exptl_crystal_size_mid 0.220 _exptl_crystal_size_min 0.200 _refine_diff_density_max 0.397 _refine_diff_density_min -0.268 _refine_ls_abs_structure_details ; Flack x determined using 1900 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.037(9) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 194 _refine_ls_number_reflns 4783 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.072 _refine_ls_R_factor_all 0.0317 _refine_ls_R_factor_gt 0.0289 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0407P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0725 _refine_ls_wR_factor_ref 0.0740 _reflns_number_gt 4492 _reflns_number_total 4783 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c5sc02923f2.cif _cod_data_source_block I _cod_depositor_comments 'Adding full bibliography for 1531040--1531042.cif.' _cod_database_code 1531042 _shelx_res_file ; TITL shs34 in Pna2(1) CELL 0.71073 14.78970 13.18670 7.88410 90.0000 90.0000 90.0000 ZERR 4.00 0.00040 0.00030 0.00020 0.0000 0.0000 0.0000 LATT -1 SYMM -X, -Y, 0.5+Z SYMM 0.5+X, 0.5-Y, Z SYMM 0.5-X, 0.5+Y, 0.5+Z SFAC C H N O V UNIT 60 88 4 16 4 L.S. 4 ACTA BOND $H omit 1 1 0 FMAP 2 PLAN 5 SIZE 0.200 0.220 0.420 TEMP -170 WGHT 0.040700 FVAR 0.27201 V1 5 0.930215 0.877705 0.926502 11.00000 0.01046 0.00944 = 0.01159 0.00032 -0.00076 -0.00018 C1 1 0.806896 1.059966 0.901863 11.00000 0.01347 0.00986 = 0.00982 -0.00128 0.00117 0.00097 C2 1 0.715133 1.085917 0.870926 11.00000 0.01275 0.01160 = 0.01268 -0.00053 0.00084 0.00048 C3 1 0.641530 1.003639 0.862492 11.00000 0.01060 0.01362 = 0.01692 -0.00069 0.00002 -0.00027 C4 1 0.657589 0.936490 0.705877 11.00000 0.01816 0.01827 = 0.01904 -0.00435 -0.00107 -0.00335 AFIX 137 H4A 2 0.653703 0.978022 0.603056 11.00000 -1.50000 H4B 2 0.611569 0.883078 0.701731 11.00000 -1.50000 H4C 2 0.717727 0.905582 0.713043 11.00000 -1.50000 AFIX 0 C5 1 0.641192 0.937245 1.022356 11.00000 0.01449 0.01594 = 0.01965 0.00270 0.00191 -0.00141 AFIX 137 H5A 2 0.589945 0.890213 1.017780 11.00000 -1.50000 H5B 2 0.635676 0.980450 1.122962 11.00000 -1.50000 H5C 2 0.697738 0.898673 1.028413 11.00000 -1.50000 AFIX 0 C6 1 0.547018 1.052327 0.847144 11.00000 0.01182 0.02093 = 0.03367 0.00039 -0.00257 0.00116 AFIX 137 H6A 2 0.536915 1.098027 0.943315 11.00000 -1.50000 H6B 2 0.500813 0.999058 0.847324 11.00000 -1.50000 H6C 2 0.543297 1.090820 0.741045 11.00000 -1.50000 AFIX 0 C7 1 0.696899 1.188125 0.842352 11.00000 0.01550 0.01537 = 0.01978 0.00225 0.00150 0.00330 AFIX 43 H7 2 0.636334 1.207618 0.818943 11.00000 -1.20000 AFIX 0 C8 1 0.763303 1.263293 0.846445 11.00000 0.02115 0.00896 = 0.02411 0.00242 0.00312 0.00172 AFIX 43 H8 2 0.747570 1.332109 0.826439 11.00000 -1.20000 AFIX 0 C9 1 0.851696 1.237274 0.879601 11.00000 0.01820 0.01074 = 0.01917 0.00007 0.00307 -0.00262 AFIX 43 H9 2 0.897120 1.288139 0.884140 11.00000 -1.20000 AFIX 0 C10 1 0.874331 1.135230 0.906649 11.00000 0.01446 0.01140 = 0.01110 -0.00203 0.00110 -0.00089 C11 1 0.967255 1.109355 0.943815 11.00000 0.01426 0.01323 = 0.01126 -0.00171 0.00052 -0.00358 AFIX 43 H11 2 1.008162 1.164139 0.959132 11.00000 -1.20000 AFIX 0 C12 1 1.096032 1.012775 1.007561 11.00000 0.01142 0.01742 = 0.01724 -0.00034 -0.00368 -0.00211 AFIX 23 H12A 2 1.100812 0.978331 1.118773 11.00000 -1.20000 H12B 2 1.120832 1.082094 1.020262 11.00000 -1.20000 AFIX 0 C13 1 1.151923 0.954955 0.877157 11.00000 0.01059 0.01931 = 0.01870 -0.00010 -0.00126 -0.00171 AFIX 23 H13A 2 1.146058 0.988445 0.765314 11.00000 -1.20000 H13B 2 1.216442 0.957035 0.910432 11.00000 -1.20000 AFIX 0 C14 1 1.121766 0.845337 0.862253 11.00000 0.01232 0.01624 = 0.02298 -0.00053 -0.00211 0.00155 AFIX 23 H14A 2 1.160196 0.809554 0.778654 11.00000 -1.20000 H14B 2 1.128591 0.811036 0.973214 11.00000 -1.20000 AFIX 0 C15 1 0.881142 0.682076 0.809858 11.00000 0.02184 0.01271 = 0.03632 -0.00485 -0.00208 0.00116 AFIX 137 H15A 2 0.880322 0.653789 0.924792 11.00000 -1.50000 H15B 2 0.941327 0.672845 0.760204 11.00000 -1.50000 H15C 2 0.836143 0.647099 0.739837 11.00000 -1.50000 AFIX 0 N1 3 0.999892 1.019338 0.958145 11.00000 0.01070 0.01484 = 0.01063 0.00009 -0.00009 -0.00152 O1 4 0.949232 0.834841 1.112758 11.00000 0.02040 0.01872 = 0.01530 0.00547 -0.00161 -0.00207 O2 4 0.829838 0.963636 0.926754 11.00000 0.01218 0.00844 = 0.02060 0.00037 0.00034 -0.00061 O3 4 1.029389 0.841160 0.809537 11.00000 0.01289 0.01458 = 0.01761 -0.00224 0.00037 0.00145 O4 4 0.860520 0.786130 0.816662 11.00000 0.01379 0.01158 = 0.02379 -0.00435 -0.00318 0.00089 HKLF 4 REM shs34 in Pna2(1) REM R1 = 0.0289 for 4492 Fo > 4sig(Fo) and 0.0317 for all 4783 data REM 194 parameters refined using 1 restraints END WGHT 0.0405 0.0000 REM Highest difference peak 0.397, deepest hole -0.268, 1-sigma level 0.061 Q1 1 0.9178 1.1169 0.9275 11.00000 0.05 0.40 Q2 1 0.8373 1.0990 0.9267 11.00000 0.05 0.35 Q3 1 0.9337 0.8770 0.8125 11.00000 0.05 0.35 Q4 1 0.7352 1.2227 0.8597 11.00000 0.05 0.34 Q5 1 0.8605 1.1834 0.9228 11.00000 0.05 0.34 ; _shelx_res_checksum 88252 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' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags_adp _atom_site_refinement_flags_posn _atom_site_occupancy V V1 0.93022(2) 0.87770(2) 0.92650(6) 0.01050(8) Uani d . . 1 C C1 0.80690(12) 1.05997(13) 0.9019(2) 0.0111(3) Uani d . . 1 C C2 0.71513(13) 1.08592(14) 0.8709(3) 0.0123(3) Uani d . . 1 C C3 0.64153(13) 1.00364(15) 0.8625(3) 0.0137(4) Uani d . . 1 C C4 0.65759(15) 0.93649(16) 0.7059(3) 0.0185(4) Uani d . . 1 H H4A 0.6537 0.978 0.6031 0.028 Uiso calc U R 1 H H4B 0.6116 0.8831 0.7017 0.028 Uiso calc U R 1 H H4C 0.7177 0.9056 0.713 0.028 Uiso calc U R 1 C C5 0.64119(14) 0.93725(16) 1.0224(3) 0.0167(4) Uani d . . 1 H H5A 0.5899 0.8902 1.0178 0.025 Uiso calc U R 1 H H5B 0.6357 0.9805 1.123 0.025 Uiso calc U R 1 H H5C 0.6977 0.8987 1.0284 0.025 Uiso calc U R 1 C C6 0.54702(14) 1.05233(17) 0.8471(3) 0.0221(5) Uani d . . 1 H H6A 0.5369 1.098 0.9433 0.033 Uiso calc U R 1 H H6B 0.5008 0.9991 0.8473 0.033 Uiso calc U R 1 H H6C 0.5433 1.0908 0.741 0.033 Uiso calc U R 1 C C7 0.69690(14) 1.18813(15) 0.8424(3) 0.0169(4) Uani d . . 1 H H7 0.6363 1.2076 0.8189 0.02 Uiso calc U R 1 C C8 0.76330(15) 1.26329(15) 0.8464(3) 0.0181(4) Uani d . . 1 H H8 0.7476 1.3321 0.8264 0.022 Uiso calc U R 1 C C9 0.85170(14) 1.23727(15) 0.8796(3) 0.0160(4) Uani d . . 1 H H9 0.8971 1.2881 0.8841 0.019 Uiso calc U R 1 C C10 0.87433(13) 1.13523(13) 0.9066(3) 0.0123(4) Uani d . . 1 C C11 0.96725(13) 1.10935(14) 0.9438(3) 0.0129(4) Uani d . . 1 H H11 1.0082 1.1641 0.9591 0.015 Uiso calc U R 1 C C12 1.09603(13) 1.01278(16) 1.0076(3) 0.0154(4) Uani d . . 1 H H12A 1.1008 0.9783 1.1188 0.018 Uiso calc U R 1 H H12B 1.1208 1.0821 1.0203 0.018 Uiso calc U R 1 C C13 1.15192(13) 0.95496(16) 0.8772(3) 0.0162(4) Uani d . . 1 H H13A 1.1461 0.9884 0.7653 0.019 Uiso calc U R 1 H H13B 1.2164 0.957 0.9104 0.019 Uiso calc U R 1 C C14 1.12177(13) 0.84534(15) 0.8623(3) 0.0172(4) Uani d . . 1 H H14A 1.1602 0.8096 0.7787 0.021 Uiso calc U R 1 H H14B 1.1286 0.811 0.9732 0.021 Uiso calc U R 1 C C15 0.88114(16) 0.68208(16) 0.8099(3) 0.0236(5) Uani d . . 1 H H15A 0.8803 0.6538 0.9248 0.035 Uiso calc U R 1 H H15B 0.9413 0.6728 0.7602 0.035 Uiso calc U R 1 H H15C 0.8361 0.6471 0.7398 0.035 Uiso calc U R 1 N N1 0.99989(11) 1.01934(12) 0.95814(19) 0.0121(3) Uani d . . 1 O O1 0.94923(11) 0.83484(12) 1.11276(19) 0.0181(3) Uani d . . 1 O O2 0.82984(8) 0.96364(9) 0.9268(2) 0.0137(2) Uani d . . 1 O O3 1.02939(9) 0.84116(11) 0.80954(19) 0.0150(3) Uani d . . 1 O O4 0.86052(9) 0.78613(11) 0.8167(2) 0.0164(3) Uani d . . 1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 V1 0.01046(13) 0.00944(14) 0.01159(13) -0.00018(10) -0.00076(14) 0.00032(13) C1 0.0135(8) 0.0099(8) 0.0098(9) 0.0010(6) 0.0012(7) -0.0013(6) C2 0.0127(8) 0.0116(9) 0.0127(7) 0.0005(7) 0.0008(7) -0.0005(7) C3 0.0106(8) 0.0136(9) 0.0169(8) -0.0003(7) 0.0000(7) -0.0007(7) C4 0.0182(10) 0.0183(10) 0.0190(9) -0.0033(8) -0.0011(8) -0.0043(8) C5 0.0145(9) 0.0159(10) 0.0196(10) -0.0014(7) 0.0019(7) 0.0027(8) C6 0.0118(9) 0.0209(11) 0.0337(13) 0.0012(8) -0.0026(9) 0.0004(9) C7 0.0155(9) 0.0154(10) 0.0198(10) 0.0033(7) 0.0015(8) 0.0022(8) C8 0.0212(10) 0.0090(9) 0.0241(11) 0.0017(7) 0.0031(9) 0.0024(8) C9 0.0182(9) 0.0107(9) 0.0192(9) -0.0026(7) 0.0031(7) 0.0001(7) C10 0.0145(8) 0.0114(8) 0.0111(10) -0.0009(6) 0.0011(7) -0.0020(7) C11 0.0143(8) 0.0132(8) 0.0113(10) -0.0036(6) 0.0005(8) -0.0017(7) C12 0.0114(8) 0.0174(10) 0.0172(9) -0.0021(7) -0.0037(7) -0.0003(7) C13 0.0106(8) 0.0193(10) 0.0187(9) -0.0017(7) -0.0013(7) -0.0001(7) C14 0.0123(9) 0.0162(10) 0.0230(9) 0.0015(7) -0.0021(8) -0.0005(8) C15 0.0218(10) 0.0127(10) 0.0363(12) 0.0012(8) -0.0021(10) -0.0048(9) N1 0.0107(7) 0.0148(7) 0.0106(8) -0.0015(6) -0.0001(5) 0.0001(6) O1 0.0204(7) 0.0187(8) 0.0153(7) -0.0021(6) -0.0016(6) 0.0055(6) O2 0.0122(5) 0.0084(5) 0.0206(6) -0.0006(4) 0.0003(6) 0.0004(7) O3 0.0129(6) 0.0146(7) 0.0176(6) 0.0014(5) 0.0004(6) -0.0022(6) O4 0.0138(7) 0.0116(7) 0.0238(7) 0.0009(5) -0.0032(6) -0.0044(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' V V 0.3005 0.5294 '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 O1 V1 O3 103.46(8) O1 V1 O4 107.70(8) O3 V1 O4 92.31(7) O1 V1 O2 110.70(8) O3 V1 O2 144.24(8) O4 V1 O2 87.28(6) O1 V1 N1 96.68(7) O3 V1 N1 84.33(6) O4 V1 N1 155.48(7) O2 V1 N1 81.58(6) O2 C1 C10 119.27(16) O2 C1 C2 119.95(16) C10 C1 C2 120.77(16) C7 C2 C1 116.47(18) C7 C2 C3 122.58(17) C1 C2 C3 120.90(16) C5 C3 C4 109.36(16) C5 C3 C2 111.66(17) C4 C3 C2 109.36(16) C5 C3 C6 107.39(17) C4 C3 C6 108.45(18) C2 C3 C6 110.55(16) C3 C4 H4A 109.5 C3 C4 H4B 109.5 H4A C4 H4B 109.5 C3 C4 H4C 109.5 H4A C4 H4C 109.5 H4B C4 H4C 109.5 C3 C5 H5A 109.5 C3 C5 H5B 109.5 H5A C5 H5B 109.5 C3 C5 H5C 109.5 H5A C5 H5C 109.5 H5B C5 H5C 109.5 C3 C6 H6A 109.5 C3 C6 H6B 109.5 H6A C6 H6B 109.5 C3 C6 H6C 109.5 H6A C6 H6C 109.5 H6B C6 H6C 109.5 C2 C7 C8 123.18(19) C2 C7 H7 118.4 C8 C7 H7 118.4 C9 C8 C7 119.71(19) C9 C8 H8 120.1 C7 C8 H8 120.1 C8 C9 C10 119.64(19) C8 C9 H9 120.2 C10 C9 H9 120.2 C9 C10 C1 120.21(17) C9 C10 C11 118.94(17) C1 C10 C11 120.83(16) N1 C11 C10 126.31(17) N1 C11 H11 116.8 C10 C11 H11 116.8 N1 C12 C13 111.94(16) N1 C12 H12A 109.2 C13 C12 H12A 109.2 N1 C12 H12B 109.2 C13 C12 H12B 109.2 H12A C12 H12B 107.9 C14 C13 C12 111.68(17) C14 C13 H13A 109.3 C12 C13 H13A 109.3 C14 C13 H13B 109.3 C12 C13 H13B 109.3 H13A C13 H13B 107.9 O3 C14 C13 109.89(16) O3 C14 H14A 109.7 C13 C14 H14A 109.7 O3 C14 H14B 109.7 C13 C14 H14B 109.7 H14A C14 H14B 108.2 O4 C15 H15A 109.5 O4 C15 H15B 109.5 H15A C15 H15B 109.5 O4 C15 H15C 109.5 H15A C15 H15C 109.5 H15B C15 H15C 109.5 C11 N1 C12 116.01(17) C11 N1 V1 127.75(14) C12 N1 V1 116.21(12) C1 O2 V1 141.49(12) C14 O3 V1 128.34(13) C15 O4 V1 123.09(13) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance V1 O1 1.5984(15) V1 O3 1.7983(15) V1 O4 1.8085(15) V1 O2 1.8676(13) V1 N1 2.1476(16) C1 O2 1.329(2) C1 C10 1.408(3) C1 C2 1.421(3) C2 C7 1.393(3) C2 C3 1.538(3) C3 C5 1.535(3) C3 C4 1.538(3) C3 C6 1.543(3) C4 H4A 0.98 C4 H4B 0.98 C4 H4C 0.98 C5 H5A 0.98 C5 H5B 0.98 C5 H5C 0.98 C6 H6A 0.98 C6 H6B 0.98 C6 H6C 0.98 C7 C8 1.396(3) C7 H7 0.95 C8 C9 1.377(3) C8 H8 0.95 C9 C10 1.403(3) C9 H9 0.95 C10 C11 1.446(3) C11 N1 1.286(2) C11 H11 0.95 C12 N1 1.477(2) C12 C13 1.524(3) C12 H12A 0.99 C12 H12B 0.99 C13 C14 1.517(3) C13 H13A 0.99 C13 H13B 0.99 C14 O3 1.429(2) C14 H14A 0.99 C14 H14B 0.99 C15 O4 1.407(2) C15 H15A 0.98 C15 H15B 0.98 C15 H15C 0.98