#------------------------------------------------------------------------------ #$Date: 2015-12-09 13:49:30 +0200 (Wed, 09 Dec 2015) $ #$Revision: 170976 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/53/10/1531041.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_1531041 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 'C30 H44 N2 O8 V2' _chemical_formula_weight 662.55 _chemical_properties_physical 'Light-sensitive, Photo-sensitive' _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' _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _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 100.8835(17) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 12.1706(6) _cell_length_b 11.0345(5) _cell_length_c 23.8844(12) _cell_measurement_reflns_used 4220 _cell_measurement_temperature 133.(2) _cell_measurement_theta_max 30.4199 _cell_measurement_theta_min 2.5122 _cell_volume 3149.9(3) _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 133.(2) _diffrn_detector_area_resol_mean 8.3333 _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.994 _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 0.0440 _diffrn_reflns_av_unetI/netI 0.0479 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 18722 _diffrn_reflns_theta_full 31.04 _diffrn_reflns_theta_max 31.04 _diffrn_reflns_theta_min 2.55 _diffrn_source 'fine-focus sealed tube' _exptl_absorpt_coefficient_mu 0.644 _exptl_absorpt_correction_T_max 0.96 _exptl_absorpt_correction_T_min 0.87 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2014/3 (Bruker AXS Inc.)' _exptl_crystal_colour red _exptl_crystal_density_diffrn 1.397 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 1392 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: methanol' _exptl_crystal_size_max 0.400 _exptl_crystal_size_mid 0.160 _exptl_crystal_size_min 0.060 _refine_diff_density_max 0.432 _refine_diff_density_min -0.434 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 222 _refine_ls_number_reflns 5001 _refine_ls_number_restraints 83 _refine_ls_restrained_S_all 1.045 _refine_ls_R_factor_all 0.0602 _refine_ls_R_factor_gt 0.0409 _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^)+(0.0418P)^2^+2.8598P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0942 _refine_ls_wR_factor_ref 0.1048 _reflns_number_gt 3899 _reflns_number_total 5001 _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 1531041 _shelx_res_file ; TITL shs32 in C2/c CELL 0.71073 12.17060 11.03450 23.88440 90.0000 100.8835 90.0000 ZERR 4.00 0.00060 0.00050 0.00120 0.0000 0.0017 0.0000 LATT 7 SYMM -X, Y, 0.5-Z SFAC C H N O V UNIT 120 176 8 32 8 omit 1 1 1 L.S. 4 ACTA BOND $H FMAP 2 PLAN 5 sadi c12 c13 c12a c13a sadi n1 c12 n1 c12a sadi o3 c14 o3 c14a SIZE 0.06 0.16 0.40 DELU 0.01 C12 > C14A SIMU 0.01 C12 > C14A ISOR 0.01 C12 > C14A TEMP -140 WGHT 0.041800 2.859800 FVAR 0.10000 0.63058 V1 5 0.137401 0.984924 0.029234 11.00000 0.01764 0.01423 = 0.01662 0.00007 0.00332 0.00147 C1 1 0.123440 0.795354 0.116420 11.00000 0.01413 0.01366 = 0.02026 0.00055 0.00349 0.00266 C2 1 0.135814 0.775436 0.176171 11.00000 0.01680 0.01655 = 0.01956 0.00061 0.00488 0.00208 C3 1 0.204191 0.862604 0.219650 11.00000 0.02369 0.01894 = 0.01528 0.00040 0.00353 0.00043 C4 1 0.326301 0.862411 0.211769 11.00000 0.02474 0.03446 = 0.02271 -0.00701 0.00104 -0.00280 AFIX 137 H4A 2 0.369802 0.919033 0.238876 11.00000 -1.50000 H4B 2 0.329793 0.887427 0.172774 11.00000 -1.50000 H4C 2 0.357377 0.780649 0.218618 11.00000 -1.50000 AFIX 0 C5 1 0.156985 0.992639 0.212446 11.00000 0.03721 0.01916 = 0.02184 -0.00292 0.00402 0.00204 AFIX 137 H5A 2 0.201382 1.045712 0.240982 11.00000 -1.50000 H5B 2 0.079000 0.992479 0.217619 11.00000 -1.50000 H5C 2 0.160593 1.022307 0.174161 11.00000 -1.50000 AFIX 0 C6 1 0.202936 0.825187 0.281304 11.00000 0.04399 0.02678 = 0.01805 0.00066 0.00705 -0.00042 AFIX 137 H6A 2 0.237667 0.745212 0.288686 11.00000 -1.50000 H6B 2 0.125477 0.821763 0.287218 11.00000 -1.50000 H6C 2 0.244862 0.884654 0.307442 11.00000 -1.50000 AFIX 0 C7 1 0.086267 0.671901 0.193593 11.00000 0.02538 0.02309 = 0.02523 0.00415 0.00757 -0.00198 AFIX 43 H7 2 0.092674 0.657261 0.233274 11.00000 -1.20000 AFIX 0 C8 1 0.027518 0.588635 0.155159 11.00000 0.03197 0.02327 = 0.03629 0.00483 0.01064 -0.00860 AFIX 43 H8 2 -0.006467 0.519886 0.168744 11.00000 -1.20000 AFIX 0 C9 1 0.019158 0.606654 0.097713 11.00000 0.02280 0.02042 = 0.03120 -0.00228 0.00163 -0.00510 AFIX 43 H9 2 -0.019074 0.549109 0.071468 11.00000 -1.20000 AFIX 0 C10 1 0.066697 0.709434 0.077587 11.00000 0.01660 0.01654 = 0.02117 -0.00116 0.00168 0.00150 C11 1 0.069462 0.716929 0.017129 11.00000 0.02023 0.01629 = 0.02173 -0.00398 -0.00277 0.00319 AFIX 43 H11 2 0.042352 0.648820 -0.005676 11.00000 -1.20000 PART 1 21.00 AFIX 0 C12 1 0.129370 0.786687 -0.066364 21.00000 0.02651 0.02323 = 0.01669 -0.00198 0.00255 0.01029 AFIX 23 H12A 2 0.106839 0.703105 -0.078526 21.00000 -1.20000 H12B 2 0.211127 0.793270 -0.064425 21.00000 -1.20000 AFIX 0 C13 1 0.070514 0.874878 -0.111443 21.00000 0.02880 0.02783 = 0.01586 -0.00184 0.00497 0.00907 AFIX 23 H13A 2 0.100355 0.863771 -0.146896 21.00000 -1.20000 H13B 2 -0.010348 0.855512 -0.120100 21.00000 -1.20000 AFIX 0 C14 1 -0.085183 0.994331 0.093020 21.00000 0.02940 0.02532 = 0.01475 0.00551 0.00702 0.00464 AFIX 23 H14A 2 -0.043105 0.942069 0.123369 21.00000 -1.20000 H14B 2 -0.165320 0.972463 0.088126 21.00000 -1.20000 PART 2 -21.00 AFIX 0 C12A 1 0.106109 0.789941 -0.069599 -21.00000 0.03000 0.02385 = 0.02091 -0.00717 0.00147 0.01068 AFIX 23 H12C 2 0.029074 0.772780 -0.090020 -21.00000 -1.20000 H12D 2 0.153193 0.718935 -0.074388 -21.00000 -1.20000 AFIX 0 C13A 1 0.150519 0.900197 -0.095958 -21.00000 0.02841 0.03179 = 0.01514 -0.00038 0.00638 0.00974 AFIX 23 H13C 2 0.154923 0.881484 -0.136013 -21.00000 -1.20000 H13D 2 0.227371 0.917259 -0.075259 -21.00000 -1.20000 AFIX 0 C14A 1 -0.079125 0.986388 0.094849 -21.00000 0.01523 0.02063 = 0.01967 -0.00282 0.00779 0.00825 AFIX 23 H14C 2 -0.011189 0.992535 0.124930 -21.00000 -1.20000 H14D 2 -0.121929 0.914421 0.103134 -21.00000 -1.20000 PART 0 AFIX 0 C15 1 0.218165 1.220640 0.071298 11.00000 0.07112 0.03677 = 0.03939 -0.01642 0.01552 -0.03072 AFIX 137 H15A 2 0.279616 1.197152 0.052306 11.00000 -1.50000 H15B 2 0.247423 1.234735 0.111886 11.00000 -1.50000 H15C 2 0.183260 1.295060 0.053926 11.00000 -1.50000 AFIX 0 N1 3 0.105073 0.806876 -0.008230 11.00000 0.02016 0.01816 = 0.01682 -0.00272 0.00153 0.00704 O1 4 0.258005 0.992070 0.012108 11.00000 0.02115 0.02815 = 0.02457 0.00612 0.00501 0.00221 O2 4 0.168146 0.893041 0.097435 11.00000 0.02034 0.01482 = 0.01618 0.00095 0.00225 -0.00109 O3 4 -0.046976 0.971278 0.040541 11.00000 0.01975 0.01705 = 0.01576 -0.00004 0.00543 0.00421 O4 4 0.138217 1.127481 0.065246 11.00000 0.03042 0.01502 = 0.02229 -0.00133 0.00090 -0.00190 HKLF 4 REM shs32 in C2/c REM R1 = 0.0409 for 3899 Fo > 4sig(Fo) and 0.0602 for all 5001 data REM 222 parameters refined using 83 restraints END WGHT 0.0418 2.8587 REM Highest difference peak 0.432, deepest hole -0.434, 1-sigma level 0.076 Q1 1 0.2066 0.9872 0.0270 11.00000 0.05 0.43 Q2 1 0.0450 0.6568 0.0940 11.00000 0.05 0.43 Q3 1 0.0617 0.7174 0.0513 11.00000 0.05 0.40 Q4 1 0.1668 0.8209 0.2014 11.00000 0.05 0.39 Q5 1 0.0517 0.6406 0.1697 11.00000 0.05 0.36 ; _shelx_res_checksum 64561 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_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_occupancy _atom_site_refinement_flags_posn _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group V V1 0.13740(2) 0.98492(2) 0.02923(2) 0.01615(8) Uani d . . . 1.0 . . C C1 0.12344(13) 0.79535(13) 0.11642(7) 0.0160(3) Uani d . . . 1.0 . . C C2 0.13581(14) 0.77544(14) 0.17617(7) 0.0174(3) Uani d . . . 1.0 . . C C3 0.20419(15) 0.86260(14) 0.21965(7) 0.0193(3) Uani d . . . 1.0 . . C C4 0.32630(16) 0.86241(18) 0.21177(8) 0.0278(4) Uani d . . . 1.0 . . H H4A 0.3698 0.919 0.2389 0.042 Uiso calc U . R 1.0 . . H H4B 0.3298 0.8874 0.1728 0.042 Uiso calc U . R 1.0 . . H H4C 0.3574 0.7806 0.2186 0.042 Uiso calc U . R 1.0 . . C C5 0.15698(17) 0.99264(15) 0.21245(8) 0.0263(4) Uani d . . . 1.0 . . H H5A 0.2014 1.0457 0.241 0.039 Uiso calc U . R 1.0 . . H H5B 0.079 0.9925 0.2176 0.039 Uiso calc U . R 1.0 . . H H5C 0.1606 1.0223 0.1742 0.039 Uiso calc U . R 1.0 . . C C6 0.20294(18) 0.82519(17) 0.28130(8) 0.0294(4) Uani d . . . 1.0 . . H H6A 0.2377 0.7452 0.2887 0.044 Uiso calc U . R 1.0 . . H H6B 0.1255 0.8218 0.2872 0.044 Uiso calc U . R 1.0 . . H H6C 0.2449 0.8847 0.3074 0.044 Uiso calc U . R 1.0 . . C C7 0.08627(16) 0.67190(15) 0.19359(8) 0.0242(4) Uani d . . . 1.0 . . H H7 0.0927 0.6573 0.2333 0.029 Uiso calc U . R 1.0 . . C C8 0.02752(17) 0.58863(17) 0.15516(9) 0.0300(4) Uani d . . . 1.0 . . H H8 -0.0065 0.5199 0.1687 0.036 Uiso calc U . R 1.0 . . C C9 0.01916(16) 0.60665(16) 0.09771(8) 0.0253(4) Uani d . . . 1.0 . . H H9 -0.0191 0.5491 0.0715 0.03 Uiso calc U . R 1.0 . . C C10 0.06670(14) 0.70943(14) 0.07759(7) 0.0183(3) Uani d . . . 1.0 . . C C11 0.06946(15) 0.71693(14) 0.01713(7) 0.0203(3) Uani d . . . 1.0 . . H H11 0.0424 0.6488 -0.0057 0.024 Uiso calc U . R 1.0 . . C C12 0.1294(6) 0.7867(7) -0.0664(3) 0.0223(12) Uani d U P D 0.631(5) A 1 H H12A 0.1068 0.7031 -0.0785 0.027 Uiso calc U P R 0.631(5) A 1 H H12B 0.2111 0.7933 -0.0644 0.027 Uiso calc U P R 0.631(5) A 1 C C13 0.0705(3) 0.8749(3) -0.11144(12) 0.0241(7) Uani d U P D 0.631(5) A 1 H H13A 0.1004 0.8638 -0.1469 0.029 Uiso calc U P R 0.631(5) A 1 H H13B -0.0103 0.8555 -0.1201 0.029 Uiso calc U P R 0.631(5) A 1 C C14 -0.0852(12) 0.9943(12) 0.0930(4) 0.0228(19) Uani d U P D 0.631(5) A 1 H H14A -0.0431 0.9421 0.1234 0.027 Uiso calc U P R 0.631(5) A 1 H H14B -0.1653 0.9725 0.0881 0.027 Uiso calc U P R 0.631(5) A 1 C C12A 0.1061(12) 0.7899(13) -0.0696(5) 0.025(2) Uani d U P D 0.369(5) A 2 H H12C 0.0291 0.7728 -0.09 0.03 Uiso calc U P R 0.369(5) A 2 H H12D 0.1532 0.7189 -0.0744 0.03 Uiso calc U P R 0.369(5) A 2 C C13A 0.1505(5) 0.9002(4) -0.0960(2) 0.0248(12) Uani d U P D 0.369(5) A 2 H H13C 0.1549 0.8815 -0.136 0.03 Uiso calc U P R 0.369(5) A 2 H H13D 0.2274 0.9173 -0.0753 0.03 Uiso calc U P R 0.369(5) A 2 C C14A -0.0791(18) 0.986(2) 0.0948(6) 0.018(3) Uani d U P D 0.369(5) A 2 H H14C -0.0112 0.9925 0.1249 0.022 Uiso calc U P R 0.369(5) A 2 H H14D -0.1219 0.9144 0.1031 0.022 Uiso calc U P R 0.369(5) A 2 C C15 0.2182(2) 1.2206(2) 0.07130(10) 0.0484(6) Uani d . . . 1.0 . . H H15A 0.2796 1.1972 0.0523 0.073 Uiso calc U . R 1.0 . . H H15B 0.2474 1.2347 0.1119 0.073 Uiso calc U . R 1.0 . . H H15C 0.1833 1.2951 0.0539 0.073 Uiso calc U . R 1.0 . . N N1 0.10507(12) 0.80688(12) -0.00823(6) 0.0186(3) Uani d . . D 1.0 . . O O1 0.25800(11) 0.99207(11) 0.01211(6) 0.0245(3) Uani d . . . 1.0 . . O O2 0.16815(10) 0.89304(10) 0.09743(5) 0.0173(2) Uani d . . . 1.0 . . O O3 -0.04698(10) 0.97128(10) 0.04054(5) 0.0173(2) Uani d . . D 1.0 . . O O4 0.13822(11) 1.12748(10) 0.06525(5) 0.0231(3) Uani d . . . 1.0 . . 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 0.01764(15) 0.01423(12) 0.01662(13) 0.00147(10) 0.00332(10) 0.00007(10) C1 0.0141(8) 0.0137(6) 0.0203(7) 0.0027(5) 0.0035(6) 0.0005(5) C2 0.0168(8) 0.0165(7) 0.0196(8) 0.0021(6) 0.0049(6) 0.0006(6) C3 0.0237(9) 0.0189(7) 0.0153(7) 0.0004(6) 0.0035(6) 0.0004(6) C4 0.0247(10) 0.0345(9) 0.0227(8) -0.0028(8) 0.0010(7) -0.0070(7) C5 0.0372(11) 0.0192(8) 0.0218(8) 0.0020(7) 0.0040(8) -0.0029(6) C6 0.0440(12) 0.0268(9) 0.0181(8) -0.0004(8) 0.0071(8) 0.0007(7) C7 0.0254(10) 0.0231(8) 0.0252(8) -0.0020(7) 0.0076(7) 0.0041(7) C8 0.0320(11) 0.0233(8) 0.0363(10) -0.0086(7) 0.0106(9) 0.0048(8) C9 0.0228(9) 0.0204(8) 0.0312(9) -0.0051(7) 0.0016(7) -0.0023(7) C10 0.0166(8) 0.0165(7) 0.0212(8) 0.0015(6) 0.0017(6) -0.0012(6) C11 0.0202(9) 0.0163(7) 0.0217(8) 0.0032(6) -0.0028(7) -0.0040(6) C12 0.027(3) 0.0232(17) 0.0167(18) 0.0103(18) 0.0026(17) -0.0020(14) C13 0.0288(18) 0.0278(13) 0.0159(12) 0.0091(11) 0.0050(11) -0.0018(10) C14 0.029(4) 0.025(3) 0.015(2) 0.005(3) 0.007(2) 0.006(2) C12A 0.030(4) 0.024(3) 0.021(3) 0.011(3) 0.001(3) -0.007(2) C13A 0.028(3) 0.032(2) 0.015(2) 0.0097(19) 0.0064(19) -0.0004(17) C14A 0.015(4) 0.021(4) 0.020(5) 0.008(3) 0.008(3) -0.003(4) C15 0.0711(18) 0.0368(11) 0.0394(12) -0.0307(12) 0.0155(12) -0.0164(10) N1 0.0202(7) 0.0182(6) 0.0168(6) 0.0070(5) 0.0015(5) -0.0027(5) O1 0.0212(7) 0.0281(6) 0.0246(6) 0.0022(5) 0.0050(5) 0.0061(5) O2 0.0203(6) 0.0148(5) 0.0162(5) -0.0011(4) 0.0023(5) 0.0009(4) O3 0.0198(6) 0.0171(5) 0.0158(5) 0.0042(4) 0.0054(4) 0.0000(4) O4 0.0304(7) 0.0150(5) 0.0223(6) -0.0019(5) 0.0009(5) -0.0013(5) 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_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle O1 V1 O4 . . 99.06(6) O1 V1 O3 . 5_575 99.95(6) O4 V1 O3 . 5_575 98.58(5) O1 V1 O2 . . 101.80(6) O4 V1 O2 . . 94.29(5) O3 V1 O2 5_575 . 152.58(5) O1 V1 N1 . . 92.47(6) O4 V1 N1 . . 168.40(6) O3 V1 N1 5_575 . 80.59(5) O2 V1 N1 . . 81.99(5) O1 V1 O3 . . 171.98(6) O4 V1 O3 . . 85.34(5) O3 V1 O3 5_575 . 72.65(5) O2 V1 O3 . . 84.45(5) N1 V1 O3 . . 83.37(5) O2 C1 C10 . . 120.18(15) O2 C1 C2 . . 119.73(14) C10 C1 C2 . . 120.06(14) C7 C2 C1 . . 117.17(15) C7 C2 C3 . . 121.39(15) C1 C2 C3 . . 121.41(14) C6 C3 C4 . . 107.67(15) C6 C3 C2 . . 112.19(14) C4 C3 C2 . . 109.24(13) C6 C3 C5 . . 106.66(14) C4 C3 C5 . . 109.68(15) C2 C3 C5 . . 111.30(14) 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 . . 122.72(17) C2 C7 H7 . . 118.6 C8 C7 H7 . . 118.6 C9 C8 C7 . . 119.63(17) C9 C8 H8 . . 120.2 C7 C8 H8 . . 120.2 C8 C9 C10 . . 120.27(17) C8 C9 H9 . . 119.9 C10 C9 H9 . . 119.9 C9 C10 C1 . . 120.09(16) C9 C10 C11 . . 118.44(15) C1 C10 C11 . . 120.95(15) N1 C11 C10 . . 125.99(15) N1 C11 H11 . . 117.0 C10 C11 H11 . . 117.0 N1 C12 C13 . . 114.4(5) N1 C12 H12A . . 108.7 C13 C12 H12A . . 108.7 N1 C12 H12B . . 108.7 C13 C12 H12B . . 108.7 H12A C12 H12B . . 107.6 C14 C13 C12 5_575 . 113.0(6) C14 C13 H13A 5_575 . 109.0 C12 C13 H13A . . 109.0 C14 C13 H13B 5_575 . 109.0 C12 C13 H13B . . 109.0 H13A C13 H13B . . 107.8 O3 C14 C13 . 5_575 112.5(8) O3 C14 H14A . . 109.1 C13 C14 H14A 5_575 . 109.1 O3 C14 H14B . . 109.1 C13 C14 H14B 5_575 . 109.1 H14A C14 H14B . . 107.8 N1 C12A C13A . . 112.4(9) N1 C12A H12C . . 109.1 C13A C12A H12C . . 109.1 N1 C12A H12D . . 109.1 C13A C12A H12D . . 109.1 H12C C12A H12D . . 107.9 C12A C13A C14A . 5_575 113.7(10) C12A C13A H13C . . 108.8 C14A C13A H13C 5_575 . 108.8 C12A C13A H13D . . 108.8 C14A C13A H13D 5_575 . 108.8 H13C C13A H13D . . 107.7 O3 C14A C13A . 5_575 111.4(13) O3 C14A H14C . . 109.4 C13A C14A H14C 5_575 . 109.4 O3 C14A H14D . . 109.4 C13A C14A H14D 5_575 . 109.4 H14C C14A H14D . . 108.0 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 C12A . . 116.0(5) C11 N1 C12 . . 118.0(3) C11 N1 V1 . . 124.03(11) C12A N1 V1 . . 119.3(5) C12 N1 V1 . . 117.9(3) C1 O2 V1 . . 134.59(10) C14A O3 V1 . 5_575 124.0(9) C14 O3 V1 . 5_575 119.7(6) C14A O3 V1 . . 122.3(9) C14 O3 V1 . . 124.7(6) V1 O3 V1 5_575 . 107.34(5) C15 O4 V1 . . 129.28(14) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance V1 O1 . 1.5984(13) V1 O4 . 1.7920(12) V1 O3 5_575 1.8787(12) V1 O2 . 1.8950(11) V1 N1 . 2.1639(14) V1 O3 . 2.3152(12) C1 O2 . 1.3254(18) C1 C10 . 1.412(2) C1 C2 . 1.424(2) C2 C7 . 1.392(2) C2 C3 . 1.539(2) C3 C6 . 1.532(2) C3 C4 . 1.533(3) C3 C5 . 1.543(2) 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 . 1.397(3) C7 H7 . 0.95 C8 C9 . 1.371(3) C8 H8 . 0.95 C9 C10 . 1.399(2) C9 H9 . 0.95 C10 C11 . 1.453(2) C11 N1 . 1.280(2) C11 H11 . 0.95 C12 N1 . 1.490(7) C12 C13 . 1.526(7) C12 H12A . 0.99 C12 H12B . 0.99 C13 C14 5_575 1.510(13) C13 H13A . 0.99 C13 H13B . 0.99 C14 O3 . 1.439(7) C14 C13 5_575 1.510(13) C14 H14A . 0.99 C14 H14B . 0.99 C12A N1 . 1.480(11) C12A C13A . 1.516(13) C12A H12C . 0.99 C12A H12D . 0.99 C13A C14A 5_575 1.53(2) C13A H13C . 0.99 C13A H13D . 0.99 C14A O3 . 1.434(12) C14A C13A 5_575 1.53(2) C14A H14C . 0.99 C14A H14D . 0.99 C15 O4 . 1.404(2) C15 H15A . 0.98 C15 H15B . 0.98 C15 H15C . 0.98 O3 V1 5_575 1.8787(12)