# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_shelx _audit_creation_method SHELXL-2013 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H14 N2 O' _chemical_formula_weight 249.28 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' _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_H-M_alt 'P 21' _space_group_name_Hall 'P 2yb' _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. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 5.6181(4) _cell_length_b 21.2320(19) _cell_length_c 10.8628(9) _cell_angle_alpha 90 _cell_angle_beta 98.103(2) _cell_angle_gamma 90 _cell_volume 1282.82(18) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2877 _cell_measurement_theta_min 2.696 _cell_measurement_theta_max 30.9375 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.291 _exptl_crystal_F_000 524 _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.07 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_max 0.7462 _exptl_absorpt_correction_T_min 0.5166 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator Confocal _diffrn_radiation_detector CCD _diffrn_measurement_device ; Rigaku AFC11 Saturn724+ (4x4 bin mode) ; _diffrn_measurement_method dtprofit.ref _diffrn_detector_area_resol_mean 28.5714 _diffrn_reflns_number 6030 _diffrn_reflns_av_unetI/netI 0.0561 _diffrn_reflns_av_R_equivalents 0.0335 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.696 _diffrn_reflns_theta_max 31.070 _diffrn_reflns_theta_full 25.242 _diffrn_measured_fraction_theta_max 0.773 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.773 _diffrn_reflns_Laue_measured_fraction_full 0.909 _diffrn_reflns_point_group_measured_fraction_max 0.779 _diffrn_reflns_point_group_measured_fraction_full 0.915 _reflns_number_total 3938 _reflns_number_gt 3256 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.966 _reflns_Friedel_fraction_max 0.784 _reflns_Friedel_fraction_full 0.922 _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refined as a 2-component inversion twin. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0452P)^2^+0.3250P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_abs_structure_details ; Refined as an inversion twin. ; _refine_ls_abs_structure_Flack -1(2) _chemical_absolute_configuration ? _refine_ls_number_reflns 3938 _refine_ls_number_parameters 354 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0579 _refine_ls_R_factor_gt 0.0414 _refine_ls_wR_factor_ref 0.1152 _refine_ls_wR_factor_gt 0.1013 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.030 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 0.9086(4) 0.92586(11) 1.12231(19) 0.0358(5) Uani 1 1 d . . . . . N1 N 0.7112(5) 0.57801(12) 0.6665(2) 0.0281(5) Uani 1 1 d . . . . . N2 N 0.6051(5) 0.65852(11) 0.8481(2) 0.0251(5) Uani 1 1 d . . . . . H2N H 0.742(7) 0.6684(17) 0.808(3) 0.040(10) Uiso 1 1 d . . . . . C1 C 0.7693(6) 0.53931(15) 0.5779(3) 0.0304(7) Uani 1 1 d . . . . . H1 H 0.9001 0.5498 0.5381 0.036 Uiso 1 1 calc R U . . . C2 C 0.6436(6) 0.48402(15) 0.5422(3) 0.0324(7) Uani 1 1 d . . . . . H2 H 0.6897 0.4583 0.4803 0.039 Uiso 1 1 calc R U . . . C3 C 0.4485(6) 0.46838(15) 0.6011(3) 0.0332(7) Uani 1 1 d . . . . . H3 H 0.3611 0.4319 0.5796 0.040 Uiso 1 1 calc R U . . . C4 C 0.3856(6) 0.50788(14) 0.6925(3) 0.0288(6) Uani 1 1 d . . . . . H4 H 0.2545 0.4985 0.7328 0.035 Uiso 1 1 calc R U . . . C5 C 0.5224(6) 0.56215(13) 0.7235(2) 0.0254(6) Uani 1 1 d . . . . . C6 C 0.4659(6) 0.60557(14) 0.8203(2) 0.0262(6) Uani 1 1 d . . . . . C7 C 0.2899(6) 0.60594(15) 0.8956(3) 0.0328(7) Uani 1 1 d . . . . . H7 H 0.1715 0.5755 0.8972 0.039 Uiso 1 1 calc R U . . . C8 C 0.3193(6) 0.66063(15) 0.9704(3) 0.0306(7) Uani 1 1 d . . . . . H8 H 0.2240 0.6726 1.0297 0.037 Uiso 1 1 calc R U . . . C9 C 0.5166(5) 0.69319(14) 0.9390(2) 0.0258(6) Uani 1 1 d . . . . . C10 C 0.6238(5) 0.75340(14) 0.9842(2) 0.0247(6) Uani 1 1 d . . . . . C11 C 0.5293(6) 0.78666(15) 1.0788(3) 0.0309(7) Uani 1 1 d . . . . . H11 H 0.3998 0.7701 1.1127 0.037 Uiso 1 1 calc R U . . . C12 C 0.6275(6) 0.84377(15) 1.1215(3) 0.0314(7) Uani 1 1 d . . . . . H12 H 0.5639 0.8650 1.1843 0.038 Uiso 1 1 calc R U . . . C13 C 0.8191(6) 0.86957(14) 1.0720(3) 0.0283(7) Uani 1 1 d . . . . . C14 C 0.9151(6) 0.83762(14) 0.9787(2) 0.0285(7) Uani 1 1 d . . . . . H14 H 1.0444 0.8546 0.9452 0.034 Uiso 1 1 calc R U . . . C15 C 0.8172(6) 0.78026(14) 0.9358(2) 0.0265(6) Uani 1 1 d . . . . . H15 H 0.8824 0.7593 0.8732 0.032 Uiso 1 1 calc R U . . . C16 C 1.0878(6) 0.95656(16) 1.0635(3) 0.0381(8) Uani 1 1 d . . . . . H16A H 1.1331 0.9953 1.1059 0.057 Uiso 1 1 calc R U . . . H16B H 1.0250 0.9653 0.9784 0.057 Uiso 1 1 calc R U . . . H16C H 1.2261 0.9298 1.0665 0.057 Uiso 1 1 calc R U . . . O2 O 0.3158(4) 0.75775(11) 0.36918(18) 0.0306(5) Uani 1 1 d . . . . . N3 N 0.1457(4) 0.34751(12) 0.3769(2) 0.0258(5) Uani 1 1 d . . . . . N4 N -0.0075(5) 0.46563(12) 0.2998(2) 0.0253(5) Uani 1 1 d . . . . . H4N H 0.142(6) 0.4623(17) 0.345(3) 0.028(8) Uiso 1 1 d . . . . . C17 C 0.2213(6) 0.29020(14) 0.4157(2) 0.0271(6) Uani 1 1 d . . . . . H17 H 0.3770 0.2865 0.4574 0.033 Uiso 1 1 calc R U . . . C18 C 0.0838(6) 0.23594(14) 0.3978(2) 0.0283(6) Uani 1 1 d . . . . . H18 H 0.1454 0.1971 0.4265 0.034 Uiso 1 1 calc R U . . . C19 C -0.1484(6) 0.24128(14) 0.3360(2) 0.0287(6) Uani 1 1 d . . . . . H19 H -0.2464 0.2059 0.3226 0.034 Uiso 1 1 calc R U . . . C20 C -0.2327(6) 0.29986(14) 0.2944(2) 0.0264(6) Uani 1 1 d . . . . . H20 H -0.3883 0.3044 0.2530 0.032 Uiso 1 1 calc R U . . . C21 C -0.0807(5) 0.35209(13) 0.3154(2) 0.0233(6) Uani 1 1 d . . . . . C22 C -0.1583(5) 0.41515(14) 0.2735(2) 0.0252(6) Uani 1 1 d . . . . . C23 C -0.3717(6) 0.43806(15) 0.2099(3) 0.0303(7) Uani 1 1 d . . . . . H23 H -0.5069 0.4144 0.1800 0.036 Uiso 1 1 calc R U . . . C24 C -0.3465(6) 0.50408(15) 0.1988(3) 0.0308(7) Uani 1 1 d . . . . . H24 H -0.4625 0.5315 0.1600 0.037 Uiso 1 1 calc R U . . . C25 C -0.1185(5) 0.52071(13) 0.2559(2) 0.0259(6) Uani 1 1 d . . . . . C26 C -0.0032(5) 0.58239(14) 0.2786(2) 0.0251(6) Uani 1 1 d . . . . . C27 C -0.1227(6) 0.63754(14) 0.2363(3) 0.0299(7) Uani 1 1 d . . . . . H27 H -0.2731 0.6348 0.1883 0.036 Uiso 1 1 calc R U . . . C28 C -0.0215(6) 0.69678(14) 0.2646(3) 0.0296(7) Uani 1 1 d . . . . . H28 H -0.1052 0.7329 0.2360 0.035 Uiso 1 1 calc R U . . . C29 C 0.2028(6) 0.70187(14) 0.3349(2) 0.0257(6) Uani 1 1 d . . . . . C30 C 0.3274(6) 0.64749(15) 0.3758(3) 0.0312(7) Uani 1 1 d . . . . . H30 H 0.4795 0.6505 0.4220 0.037 Uiso 1 1 calc R U . . . C31 C 0.2254(6) 0.58875(14) 0.3478(3) 0.0300(7) Uani 1 1 d . . . . . H31 H 0.3110 0.5528 0.3755 0.036 Uiso 1 1 calc R U . . . C32 C 0.1805(6) 0.81419(14) 0.3439(3) 0.0325(7) Uani 1 1 d . . . . . H32A H 0.2741 0.8495 0.3782 0.049 Uiso 1 1 calc R U . . . H32B H 0.0353 0.8116 0.3808 0.049 Uiso 1 1 calc R U . . . H32C H 0.1409 0.8195 0.2556 0.049 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 0.0418(15) 0.0287(12) 0.0373(10) -0.0107(9) 0.0069(9) 0.0007(10) N1 0.0278(15) 0.0259(13) 0.0304(11) 0.0028(10) 0.0036(10) 0.0024(11) N2 0.0274(16) 0.0218(12) 0.0260(10) 0.0013(9) 0.0034(10) 0.0024(10) C1 0.032(2) 0.0289(16) 0.0300(13) 0.0032(12) 0.0056(12) 0.0060(13) C2 0.041(2) 0.0264(16) 0.0289(13) -0.0005(11) 0.0014(12) 0.0064(13) C3 0.043(2) 0.0213(14) 0.0324(13) 0.0019(12) -0.0034(12) 0.0011(13) C4 0.0309(18) 0.0242(14) 0.0307(13) 0.0046(11) 0.0024(12) 0.0000(12) C5 0.0283(18) 0.0227(13) 0.0246(11) 0.0057(10) 0.0014(11) 0.0055(11) C6 0.0244(17) 0.0247(14) 0.0292(12) 0.0035(11) 0.0023(11) 0.0010(12) C7 0.035(2) 0.0287(16) 0.0361(14) 0.0013(12) 0.0091(13) -0.0037(13) C8 0.034(2) 0.0301(16) 0.0297(12) 0.0001(12) 0.0105(12) 0.0015(13) C9 0.0289(18) 0.0254(14) 0.0227(11) 0.0004(10) 0.0028(10) 0.0046(12) C10 0.0252(16) 0.0260(14) 0.0217(10) 0.0013(10) -0.0006(10) 0.0057(12) C11 0.030(2) 0.0343(17) 0.0283(12) -0.0022(12) 0.0054(12) 0.0028(13) C12 0.032(2) 0.0327(17) 0.0293(13) -0.0067(12) 0.0052(12) 0.0077(14) C13 0.0307(19) 0.0262(15) 0.0258(12) -0.0049(11) -0.0035(11) 0.0046(12) C14 0.0300(19) 0.0305(16) 0.0240(12) -0.0033(11) 0.0006(11) 0.0018(13) C15 0.0325(19) 0.0265(15) 0.0209(11) -0.0038(10) 0.0045(11) 0.0040(12) C16 0.037(2) 0.0311(18) 0.0455(16) -0.0093(14) 0.0018(14) 0.0021(14) O2 0.0355(13) 0.0217(10) 0.0329(9) 0.0008(9) -0.0012(8) -0.0024(9) N3 0.0263(15) 0.0234(12) 0.0268(10) 0.0003(9) 0.0009(9) -0.0011(10) N4 0.0259(16) 0.0200(11) 0.0289(10) -0.0005(9) -0.0002(9) 0.0013(10) C17 0.0254(19) 0.0272(15) 0.0282(12) 0.0014(11) 0.0022(11) 0.0035(12) C18 0.0357(19) 0.0236(14) 0.0257(12) 0.0006(11) 0.0050(11) 0.0023(12) C19 0.0353(19) 0.0238(15) 0.0277(12) -0.0027(11) 0.0070(12) -0.0047(12) C20 0.0274(18) 0.0256(14) 0.0251(11) -0.0022(11) -0.0002(11) 0.0009(12) C21 0.0258(17) 0.0220(13) 0.0226(11) -0.0016(10) 0.0049(10) 0.0001(11) C22 0.0255(18) 0.0242(14) 0.0255(12) -0.0035(11) 0.0027(11) -0.0004(11) C23 0.0271(19) 0.0288(15) 0.0340(13) -0.0054(12) 0.0008(12) -0.0028(13) C24 0.0305(19) 0.0262(15) 0.0336(14) 0.0009(12) -0.0033(12) 0.0046(13) C25 0.0304(18) 0.0211(13) 0.0252(12) 0.0007(10) 0.0010(11) 0.0019(12) C26 0.0270(16) 0.0234(13) 0.0245(11) 0.0001(10) 0.0015(10) 0.0026(11) C27 0.0333(19) 0.0232(14) 0.0302(12) 0.0007(11) -0.0063(12) 0.0010(12) C28 0.0330(19) 0.0233(14) 0.0304(13) 0.0017(11) -0.0023(12) 0.0052(13) C29 0.0331(18) 0.0218(14) 0.0225(11) 0.0009(10) 0.0042(11) -0.0029(12) C30 0.0272(19) 0.0278(15) 0.0364(14) 0.0016(12) -0.0034(12) -0.0017(13) C31 0.0280(18) 0.0232(15) 0.0375(14) 0.0033(12) 0.0004(12) 0.0023(12) C32 0.044(2) 0.0201(14) 0.0341(14) -0.0002(11) 0.0073(13) -0.0010(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 C13 1.379(4) . ? O1 C16 1.424(4) . ? N1 C1 1.341(4) . ? N1 C5 1.344(4) . ? N2 C6 1.378(4) . ? N2 C9 1.380(4) . ? N2 H2N 0.96(4) . ? C1 C2 1.397(4) . ? C1 H1 0.9300 . ? C2 C3 1.386(5) . ? C2 H2 0.9300 . ? C3 C4 1.383(4) . ? C3 H3 0.9300 . ? C4 C5 1.399(4) . ? C4 H4 0.9300 . ? C5 C6 1.467(4) . ? C6 C7 1.369(4) . ? C7 C8 1.414(4) . ? C7 H7 0.9300 . ? C8 C9 1.389(4) . ? C8 H8 0.9300 . ? C9 C10 1.468(4) . ? C10 C15 1.394(4) . ? C10 C11 1.411(4) . ? C11 C12 1.385(4) . ? C11 H11 0.9300 . ? C12 C13 1.383(5) . ? C12 H12 0.9300 . ? C13 C14 1.390(4) . ? C14 C15 1.390(4) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? O2 C29 1.372(4) . ? O2 C32 1.425(4) . ? N3 C17 1.337(4) . ? N3 C21 1.355(4) . ? N4 C22 1.371(4) . ? N4 C25 1.379(4) . ? N4 H4N 0.92(3) . ? C17 C18 1.386(4) . ? C17 H17 0.9300 . ? C18 C19 1.385(4) . ? C18 H18 0.9300 . ? C19 C20 1.384(4) . ? C19 H19 0.9300 . ? C20 C21 1.398(4) . ? C20 H20 0.9300 . ? C21 C22 1.461(4) . ? C22 C23 1.385(4) . ? C23 C24 1.416(4) . ? C23 H23 0.9300 . ? C24 C25 1.388(4) . ? C24 H24 0.9300 . ? C25 C26 1.467(4) . ? C26 C27 1.395(4) . ? C26 C31 1.400(4) . ? C27 C28 1.396(4) . ? C27 H27 0.9300 . ? C28 C29 1.383(4) . ? C28 H28 0.9300 . ? C29 C30 1.390(4) . ? C30 C31 1.388(4) . ? C30 H30 0.9300 . ? C31 H31 0.9300 . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? 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 C13 O1 C16 117.4(2) . . ? C1 N1 C5 117.7(3) . . ? C6 N2 C9 110.0(3) . . ? C6 N2 H2N 123(2) . . ? C9 N2 H2N 127(2) . . ? N1 C1 C2 123.3(3) . . ? N1 C1 H1 118.3 . . ? C2 C1 H1 118.3 . . ? C3 C2 C1 118.4(3) . . ? C3 C2 H2 120.8 . . ? C1 C2 H2 120.8 . . ? C4 C3 C2 119.0(3) . . ? C4 C3 H3 120.5 . . ? C2 C3 H3 120.5 . . ? C3 C4 C5 119.0(3) . . ? C3 C4 H4 120.5 . . ? C5 C4 H4 120.5 . . ? N1 C5 C4 122.6(3) . . ? N1 C5 C6 115.9(3) . . ? C4 C5 C6 121.5(3) . . ? C7 C6 N2 107.4(3) . . ? C7 C6 C5 132.8(3) . . ? N2 C6 C5 119.8(3) . . ? C6 C7 C8 108.2(3) . . ? C6 C7 H7 125.9 . . ? C8 C7 H7 125.9 . . ? C9 C8 C7 107.5(3) . . ? C9 C8 H8 126.3 . . ? C7 C8 H8 126.3 . . ? N2 C9 C8 106.9(3) . . ? N2 C9 C10 122.1(3) . . ? C8 C9 C10 131.0(3) . . ? C15 C10 C11 117.6(3) . . ? C15 C10 C9 122.3(2) . . ? C11 C10 C9 120.0(3) . . ? C12 C11 C10 120.6(3) . . ? C12 C11 H11 119.7 . . ? C10 C11 H11 119.7 . . ? C13 C12 C11 120.8(3) . . ? C13 C12 H12 119.6 . . ? C11 C12 H12 119.6 . . ? O1 C13 C12 116.7(3) . . ? O1 C13 C14 123.7(3) . . ? C12 C13 C14 119.6(3) . . ? C15 C14 C13 119.8(3) . . ? C15 C14 H14 120.1 . . ? C13 C14 H14 120.1 . . ? C14 C15 C10 121.6(3) . . ? C14 C15 H15 119.2 . . ? C10 C15 H15 119.2 . . ? O1 C16 H16A 109.5 . . ? O1 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? O1 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C29 O2 C32 117.4(2) . . ? C17 N3 C21 117.1(3) . . ? C22 N4 C25 110.8(2) . . ? C22 N4 H4N 123(2) . . ? C25 N4 H4N 126(2) . . ? N3 C17 C18 124.5(3) . . ? N3 C17 H17 117.7 . . ? C18 C17 H17 117.7 . . ? C19 C18 C17 117.9(3) . . ? C19 C18 H18 121.0 . . ? C17 C18 H18 121.0 . . ? C20 C19 C18 119.2(3) . . ? C20 C19 H19 120.4 . . ? C18 C19 H19 120.4 . . ? C19 C20 C21 119.1(3) . . ? C19 C20 H20 120.4 . . ? C21 C20 H20 120.4 . . ? N3 C21 C20 122.2(3) . . ? N3 C21 C22 116.0(3) . . ? C20 C21 C22 121.8(3) . . ? N4 C22 C23 107.2(3) . . ? N4 C22 C21 120.2(2) . . ? C23 C22 C21 132.6(3) . . ? C22 C23 C24 107.5(3) . . ? C22 C23 H23 126.3 . . ? C24 C23 H23 126.3 . . ? C25 C24 C23 108.1(3) . . ? C25 C24 H24 125.9 . . ? C23 C24 H24 125.9 . . ? N4 C25 C24 106.4(3) . . ? N4 C25 C26 122.1(2) . . ? C24 C25 C26 131.3(3) . . ? C27 C26 C31 117.3(3) . . ? C27 C26 C25 120.9(3) . . ? C31 C26 C25 121.8(3) . . ? C26 C27 C28 121.4(3) . . ? C26 C27 H27 119.3 . . ? C28 C27 H27 119.3 . . ? C29 C28 C27 120.2(3) . . ? C29 C28 H28 119.9 . . ? C27 C28 H28 119.9 . . ? O2 C29 C28 124.6(3) . . ? O2 C29 C30 116.0(3) . . ? C28 C29 C30 119.4(3) . . ? C31 C30 C29 120.2(3) . . ? C31 C30 H30 119.9 . . ? C29 C30 H30 119.9 . . ? C30 C31 C26 121.6(3) . . ? C30 C31 H31 119.2 . . ? C26 C31 H31 119.2 . . ? O2 C32 H32A 109.5 . . ? O2 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? O2 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? 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 C5 N1 C1 C2 0.2(4) . . . . ? N1 C1 C2 C3 0.1(4) . . . . ? C1 C2 C3 C4 0.1(4) . . . . ? C2 C3 C4 C5 -0.6(4) . . . . ? C1 N1 C5 C4 -0.7(4) . . . . ? C1 N1 C5 C6 179.7(2) . . . . ? C3 C4 C5 N1 0.9(4) . . . . ? C3 C4 C5 C6 -179.5(3) . . . . ? C9 N2 C6 C7 -1.0(3) . . . . ? C9 N2 C6 C5 178.5(2) . . . . ? N1 C5 C6 C7 178.9(3) . . . . ? C4 C5 C6 C7 -0.7(5) . . . . ? N1 C5 C6 N2 -0.4(4) . . . . ? C4 C5 C6 N2 180.0(3) . . . . ? N2 C6 C7 C8 0.7(3) . . . . ? C5 C6 C7 C8 -178.7(3) . . . . ? C6 C7 C8 C9 -0.1(3) . . . . ? C6 N2 C9 C8 1.0(3) . . . . ? C6 N2 C9 C10 -177.8(2) . . . . ? C7 C8 C9 N2 -0.5(3) . . . . ? C7 C8 C9 C10 178.0(3) . . . . ? N2 C9 C10 C15 1.9(4) . . . . ? C8 C9 C10 C15 -176.5(3) . . . . ? N2 C9 C10 C11 -179.0(3) . . . . ? C8 C9 C10 C11 2.6(4) . . . . ? C15 C10 C11 C12 -0.3(4) . . . . ? C9 C10 C11 C12 -179.5(3) . . . . ? C10 C11 C12 C13 0.4(4) . . . . ? C16 O1 C13 C12 -173.2(3) . . . . ? C16 O1 C13 C14 8.7(4) . . . . ? C11 C12 C13 O1 -178.6(3) . . . . ? C11 C12 C13 C14 -0.4(4) . . . . ? O1 C13 C14 C15 178.3(2) . . . . ? C12 C13 C14 C15 0.3(4) . . . . ? C13 C14 C15 C10 -0.1(4) . . . . ? C11 C10 C15 C14 0.1(4) . . . . ? C9 C10 C15 C14 179.3(3) . . . . ? C21 N3 C17 C18 -0.5(4) . . . . ? N3 C17 C18 C19 -0.2(4) . . . . ? C17 C18 C19 C20 0.3(4) . . . . ? C18 C19 C20 C21 0.3(4) . . . . ? C17 N3 C21 C20 1.1(4) . . . . ? C17 N3 C21 C22 -179.6(2) . . . . ? C19 C20 C21 N3 -1.0(4) . . . . ? C19 C20 C21 C22 179.8(2) . . . . ? C25 N4 C22 C23 0.6(3) . . . . ? C25 N4 C22 C21 -177.8(2) . . . . ? N3 C21 C22 N4 -1.7(4) . . . . ? C20 C21 C22 N4 177.6(3) . . . . ? N3 C21 C22 C23 -179.6(3) . . . . ? C20 C21 C22 C23 -0.3(5) . . . . ? N4 C22 C23 C24 -0.2(3) . . . . ? C21 C22 C23 C24 177.9(3) . . . . ? C22 C23 C24 C25 -0.1(3) . . . . ? C22 N4 C25 C24 -0.6(3) . . . . ? C22 N4 C25 C26 175.9(3) . . . . ? C23 C24 C25 N4 0.5(3) . . . . ? C23 C24 C25 C26 -175.6(3) . . . . ? N4 C25 C26 C27 -178.0(3) . . . . ? C24 C25 C26 C27 -2.5(5) . . . . ? N4 C25 C26 C31 -0.8(4) . . . . ? C24 C25 C26 C31 174.8(3) . . . . ? C31 C26 C27 C28 -1.7(5) . . . . ? C25 C26 C27 C28 175.6(3) . . . . ? C26 C27 C28 C29 0.6(5) . . . . ? C32 O2 C29 C28 8.3(4) . . . . ? C32 O2 C29 C30 -171.5(3) . . . . ? C27 C28 C29 O2 -179.0(3) . . . . ? C27 C28 C29 C30 0.8(4) . . . . ? O2 C29 C30 C31 178.8(3) . . . . ? C28 C29 C30 C31 -1.1(5) . . . . ? C29 C30 C31 C26 -0.1(5) . . . . ? C27 C26 C31 C30 1.5(4) . . . . ? C25 C26 C31 C30 -175.8(3) . . . . ? _refine_diff_density_max 0.219 _refine_diff_density_min -0.235 _refine_diff_density_rms 0.049 _shelxl_version_number 2013-4 _shelx_res_file ; TITL WVR703a_0m in P1 New: P21 CELL 0.71073 5.6181 21.2320 10.8628 90.000 98.103 90.000 ZERR 4 0.0004 0.0019 0.0009 0.000 0.002 0.000 LATT -1 SYMM - X , 0.50000 + Y , - Z SFAC C H N O UNIT 64 52 8 4 omit 0 -1 1 omit 0 1 1 omit 0 -2 0 omit 0 2 0 omit -5 16 7 omit 0 0 1 omit -1 1 1 L.S. 20 ACTA BOND $H FMAP 2 PLAN 0 twin CONF WGHT 0.045200 0.325000 BASF -1.38355 FVAR 0.25026 O1 4 0.908641 0.925858 1.122309 11.00000 0.04175 0.02875 = 0.03726 -0.01072 0.00688 0.00071 N1 3 0.711241 0.578013 0.666522 11.00000 0.02776 0.02593 = 0.03036 0.00284 0.00358 0.00237 N2 3 0.605145 0.658523 0.848094 11.00000 0.02743 0.02182 = 0.02603 0.00125 0.00342 0.00239 H2N 2 0.742320 0.668426 0.808383 11.00000 0.03988 C1 1 0.769349 0.539307 0.577851 11.00000 0.03247 0.02894 = 0.03001 0.00325 0.00559 0.00601 AFIX 43 H1 2 0.900060 0.549819 0.538103 11.00000 -1.20000 AFIX 0 C2 1 0.643592 0.484016 0.542151 11.00000 0.04081 0.02644 = 0.02886 -0.00051 0.00136 0.00639 AFIX 43 H2 2 0.689660 0.458319 0.480312 11.00000 -1.20000 AFIX 0 C3 1 0.448480 0.468384 0.601136 11.00000 0.04344 0.02125 = 0.03242 0.00191 -0.00341 0.00107 AFIX 43 H3 2 0.361058 0.431865 0.579564 11.00000 -1.20000 AFIX 0 C4 1 0.385648 0.507875 0.692541 11.00000 0.03094 0.02421 = 0.03070 0.00464 0.00240 -0.00002 AFIX 43 H4 2 0.254519 0.498510 0.732848 11.00000 -1.20000 AFIX 0 C5 1 0.522431 0.562150 0.723451 11.00000 0.02829 0.02268 = 0.02465 0.00566 0.00136 0.00549 C6 1 0.465949 0.605574 0.820291 11.00000 0.02445 0.02468 = 0.02916 0.00353 0.00229 0.00102 C7 1 0.289927 0.605935 0.895557 11.00000 0.03475 0.02874 = 0.03607 0.00127 0.00913 -0.00374 AFIX 43 H7 2 0.171481 0.575468 0.897183 11.00000 -1.20000 AFIX 0 C8 1 0.319347 0.660626 0.970374 11.00000 0.03359 0.03014 = 0.02966 0.00009 0.01046 0.00152 AFIX 43 H8 2 0.224026 0.672608 1.029750 11.00000 -1.20000 AFIX 0 C9 1 0.516568 0.693187 0.939014 11.00000 0.02889 0.02541 = 0.02273 0.00041 0.00283 0.00456 C10 1 0.623773 0.753403 0.984180 11.00000 0.02515 0.02604 = 0.02174 0.00128 -0.00063 0.00574 C11 1 0.529310 0.786662 1.078765 11.00000 0.03035 0.03435 = 0.02829 -0.00221 0.00536 0.00282 AFIX 43 H11 2 0.399829 0.770084 1.112734 11.00000 -1.20000 AFIX 0 C12 1 0.627516 0.843765 1.121533 11.00000 0.03238 0.03266 = 0.02934 -0.00666 0.00523 0.00766 AFIX 43 H12 2 0.563855 0.865004 1.184300 11.00000 -1.20000 AFIX 0 C13 1 0.819139 0.869565 1.071982 11.00000 0.03072 0.02621 = 0.02578 -0.00494 -0.00352 0.00462 C14 1 0.915090 0.837617 0.978720 11.00000 0.02997 0.03048 = 0.02401 -0.00334 0.00064 0.00180 AFIX 43 H14 2 1.044390 0.854572 0.945155 11.00000 -1.20000 AFIX 0 C15 1 0.817234 0.780258 0.935773 11.00000 0.03247 0.02649 = 0.02089 -0.00378 0.00453 0.00402 AFIX 43 H15 2 0.882386 0.759262 0.873197 11.00000 -1.20000 AFIX 0 C16 1 1.087806 0.956564 1.063492 11.00000 0.03654 0.03107 = 0.04549 -0.00929 0.00185 0.00214 AFIX 137 H16A 2 1.133106 0.995327 1.105934 11.00000 -1.50000 H16B 2 1.024976 0.965304 0.978392 11.00000 -1.50000 H16C 2 1.226123 0.929762 1.066498 11.00000 -1.50000 AFIX 0 O2 4 0.315800 0.757750 0.369183 11.00000 0.03546 0.02167 = 0.03290 0.00080 -0.00119 -0.00238 N3 3 0.145733 0.347512 0.376942 11.00000 0.02635 0.02342 = 0.02676 0.00031 0.00092 -0.00105 N4 3 -0.007503 0.465625 0.299773 11.00000 0.02587 0.01996 = 0.02888 -0.00047 -0.00023 0.00126 H4N 2 0.142460 0.462350 0.345032 11.00000 0.02808 C17 1 0.221337 0.290205 0.415656 11.00000 0.02540 0.02724 = 0.02822 0.00137 0.00218 0.00348 AFIX 43 H17 2 0.376983 0.286506 0.457435 11.00000 -1.20000 AFIX 0 C18 1 0.083782 0.235944 0.397823 11.00000 0.03575 0.02362 = 0.02570 0.00062 0.00504 0.00228 AFIX 43 H18 2 0.145424 0.197150 0.426481 11.00000 -1.20000 AFIX 0 C19 1 -0.148376 0.241280 0.335989 11.00000 0.03533 0.02382 = 0.02770 -0.00266 0.00698 -0.00474 AFIX 43 H19 2 -0.246386 0.205937 0.322580 11.00000 -1.20000 AFIX 0 C20 1 -0.232672 0.299860 0.294409 11.00000 0.02744 0.02562 = 0.02510 -0.00215 -0.00019 0.00094 AFIX 43 H20 2 -0.388285 0.304434 0.253045 11.00000 -1.20000 AFIX 0 C21 1 -0.080728 0.352087 0.315422 11.00000 0.02577 0.02197 = 0.02262 -0.00158 0.00494 0.00013 C22 1 -0.158320 0.415149 0.273491 11.00000 0.02547 0.02419 = 0.02554 -0.00346 0.00271 -0.00042 C23 1 -0.371725 0.438059 0.209941 11.00000 0.02712 0.02879 = 0.03402 -0.00542 0.00075 -0.00276 AFIX 43 H23 2 -0.506897 0.414405 0.180037 11.00000 -1.20000 AFIX 0 C24 1 -0.346505 0.504083 0.198813 11.00000 0.03049 0.02616 = 0.03360 0.00085 -0.00334 0.00460 AFIX 43 H24 2 -0.462539 0.531532 0.160000 11.00000 -1.20000 AFIX 0 C25 1 -0.118536 0.520710 0.255893 11.00000 0.03041 0.02106 = 0.02524 0.00069 0.00097 0.00188 C26 1 -0.003172 0.582390 0.278648 11.00000 0.02695 0.02341 = 0.02445 0.00015 0.00155 0.00262 C27 1 -0.122731 0.637543 0.236329 11.00000 0.03328 0.02315 = 0.03024 0.00068 -0.00632 0.00098 AFIX 43 H27 2 -0.273070 0.634797 0.188284 11.00000 -1.20000 AFIX 0 C28 1 -0.021499 0.696775 0.264565 11.00000 0.03301 0.02329 = 0.03045 0.00166 -0.00230 0.00520 AFIX 43 H28 2 -0.105180 0.732907 0.235960 11.00000 -1.20000 AFIX 0 C29 1 0.202787 0.701873 0.334928 11.00000 0.03305 0.02177 = 0.02251 0.00093 0.00423 -0.00290 C30 1 0.327445 0.647485 0.375782 11.00000 0.02717 0.02777 = 0.03636 0.00165 -0.00341 -0.00174 AFIX 43 H30 2 0.479506 0.650463 0.421992 11.00000 -1.20000 AFIX 0 C31 1 0.225449 0.588751 0.347754 11.00000 0.02805 0.02316 = 0.03755 0.00328 0.00039 0.00231 AFIX 43 H31 2 0.311031 0.552773 0.375545 11.00000 -1.20000 AFIX 0 C32 1 0.180474 0.814188 0.343898 11.00000 0.04373 0.02010 = 0.03409 -0.00023 0.00733 -0.00105 AFIX 137 H32A 2 0.274061 0.849477 0.378225 11.00000 -1.50000 H32B 2 0.035262 0.811613 0.380816 11.00000 -1.50000 H32C 2 0.140930 0.819496 0.255619 11.00000 -1.50000 AFIX 0 HKLF 4 REM WVR703a_0m in P1 New: P21 REM R1 = 0.0414 for 3256 Fo > 4sig(Fo) and 0.0579 for all 3938 data REM 354 parameters refined using 1 restraints END WGHT 0.0452 0.3241 REM Highest difference peak 0.219, deepest hole -0.235, 1-sigma level 0.049 Q1 1 0.1828 0.2363 0.3583 11.00000 0.05 0.22 Q2 1 0.1562 0.5200 0.3197 11.00000 0.05 0.20 Q3 1 -0.3457 0.6493 0.2199 11.00000 0.05 0.18 Q4 1 0.3632 0.7018 0.2417 11.00000 0.05 0.18 Q5 1 0.4376 0.3116 0.3576 11.00000 0.05 0.17 Q6 1 -0.1103 0.3310 0.2977 11.00000 0.05 0.17 Q7 1 0.1931 0.6578 0.9105 11.00000 0.05 0.17 Q8 1 0.5556 0.7653 1.0142 11.00000 0.05 0.17 Q9 1 -0.6770 0.4678 0.1524 11.00000 0.05 0.16 Q10 1 -0.0049 0.2950 0.3580 11.00000 0.05 0.16 Q11 1 0.4184 0.7889 1.0386 11.00000 0.05 0.16 Q12 1 -0.4061 0.5203 0.1807 11.00000 0.05 0.16 Q13 1 0.4879 0.2901 0.4474 11.00000 0.05 0.16 Q14 1 0.8136 0.6122 0.6805 11.00000 0.05 0.16 Q15 1 0.8451 0.6007 0.4576 11.00000 0.05 0.16 Q16 1 -0.4743 0.3194 0.2609 11.00000 0.05 0.16 Q17 1 1.0488 0.7894 0.9896 11.00000 0.05 0.16 Q18 1 1.3679 0.9500 1.0418 11.00000 0.05 0.16 Q19 1 0.5596 0.3361 0.4356 11.00000 0.05 0.16 Q20 1 0.7408 0.5105 0.5667 11.00000 0.05 0.15 ; _shelx_res_checksum 63898 _database_code_depnum_ccdc_archive 'CCDC 962821'