# Electronic Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2012 data_global _journal_name_full 'New J.Chem.' _journal_coden_cambridge 0440 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name _publ_author_address 'Yennifer Hill' ; Centro de Qu\'imica Instituto Venezolano de Investigaciones Cient\'ifica (IVIC) Apartado 21827 Caracas 1020-A Venezuela ; 'Maholy Linares' ; Centro de Qu\'imica Instituto Venezolano de Investigaciones Cient\'ifica (IVIC) Apartado 21827 Caracas 1020-A Venezuela ; A.Briceno ; Centro de Qu\'imica Instituto Venezolano de Investigaciones Cient\'ifica (IVIC) Apartado 21827 Caracas 1020-A Venezuela ; _publ_contact_author_address ; Centro de Qu\'imica Instituto Venezolano de Investigaciones Cient\'ifica (IVIC) Apartado 21827 Caracas 1020-A Venezuela ; _publ_contact_author_email abriceno@ivic.gob.ve _publ_contact_author_fax '(58-212) 504-1350' _publ_contact_author_phone '(58-212) 504-1320' #========================================================================== _publ_contact_author_name 'Dr. Alexander Briceno' #TrackingRef '- compound1.cif' #========================================================================== # SUBMISSION DETAILS _publ_contact_letter ; Date of submission: 2011-06-29 Please consider this CIF submission for publication in CrysEngComm. All authors have seen and approved this submission. The CIF has passed the Chester CHECKCIF routines and gives a satisfactory PRINTCIF file. Best wishes, Dr. Alexander Brice\~no ; _publ_requested_category ? _publ_requested_coeditor_name ? #========================================================================== #========================================================================== # TITLE AND AUTHOR LIST _publ_section_title ; Combining topochemical [2+2] photoreactions and hydrothermal isomerisation for the regioselective and quantitative preparation of rtct-pyridylcyclobutanes ; data_shelxl1 _database_code_depnum_ccdc_archive 'CCDC 831805' #========================================================================== _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H4 O8, 0.5(C24 H24 N4), 5(H2 O)' _chemical_formula_sum 'C22 H26 N2 O13' _chemical_formula_weight 526.45 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' O O 0.0106 0.0060 '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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Fdd2 _symmetry_space_group_name_Hall 'F 2 -2d ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/4, y+1/4, z+1/4' 'x+1/4, -y+1/4, z+1/4' '-x+1/2, -y, z+1/2' 'x, y+1/2, z+1/2' '-x+1/4, y+3/4, z+3/4' 'x+1/4, -y+3/4, z+3/4' '-x+1/2, -y+1/2, z+1' 'x+1/2, y, z+1/2' '-x+3/4, y+1/4, z+3/4' 'x+3/4, -y+1/4, z+3/4' '-x+1, -y, z+1' 'x+1/2, y+1/2, z' '-x+3/4, y+3/4, z+1/4' 'x+3/4, -y+3/4, z+1/4' '-x+1, -y+1/2, z+1/2' _cell_length_a 27.455(7) _cell_length_b 36.891(9) _cell_length_c 9.656(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 9781(4) _cell_formula_units_Z 16 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1632 _cell_measurement_theta_min 2.00 _cell_measurement_theta_max 27.60 _exptl_crystal_description prism _exptl_crystal_colour 'pale brown' _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.430 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 4416 _exptl_absorpt_coefficient_mu 0.120 _exptl_absorpt_correction_type 'Multi Scan' _exptl_absorpt_correction_T_min 0.956 _exptl_absorpt_correction_T_max 0.975 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku AFC7S Mercury' _diffrn_measurement_method '\w ' _diffrn_radiation_detector CCD _diffrn_measurement_device 'Mercury (2x2 bin mode)' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 26648 _diffrn_reflns_av_R_equivalents 0.0349 _diffrn_reflns_av_sigmaI/netI 0.0792 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -41 _diffrn_reflns_limit_k_max 41 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.21 _diffrn_reflns_theta_max 27.65 _reflns_number_total 4181 _reflns_number_gt 3579 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_cell_refinement 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_data_reduction 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_structure_solution 'SHELXLTL-NT V5.1 (Bruker AXS, 1998)' _computing_structure_refinement 'SHELXLTL-NT V5.1 (Bruker AXS, 1998)' _computing_molecular_graphics ; SHELXLTL-NT V5.1 (Bruker AXS, 1998) and DIAMOND (Brandenburg, 1998) ; _computing_publication_material ; SHELXLTL-NT V5.1 (Bruker AXS, 1998) and PLATON (Spek, 2003). ; _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1057P)^2^+4.1889P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4181 _refine_ls_number_parameters 290 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0664 _refine_ls_R_factor_gt 0.0578 _refine_ls_wR_factor_ref 0.1635 _refine_ls_wR_factor_gt 0.1561 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.88238(11) 0.12365(7) -0.1353(2) 0.0655(7) Uani 1 1 d . . . H1O1 H 0.8914 0.1276 -0.2405 0.079 Uiso 1 1 d R . . O2 O 0.92795(12) 0.17119(8) -0.0949(3) 0.0731(8) Uani 1 1 d . . . O3 O 0.86479(13) 0.22007(7) 0.0727(4) 0.0892(10) Uani 1 1 d . . . O4 O 0.93430(11) 0.22447(7) 0.1882(3) 0.0731(8) Uani 1 1 d . . . O5 O 0.89892(11) 0.13331(8) 0.6136(2) 0.0706(8) Uani 1 1 d . . . O6 O 0.83305(10) 0.10097(7) 0.5632(2) 0.0628(7) Uani 1 1 d . . . O7 O 0.87198(15) 0.03421(7) 0.2396(3) 0.0883(11) Uani 1 1 d . . . H7OH H 0.8819 0.0024 0.2614 0.106 Uiso 1 1 d R . . O8 O 0.90371(14) 0.04926(8) 0.4382(3) 0.0862(10) Uani 1 1 d . . . C1 C 0.89274(11) 0.13996(7) 0.0965(3) 0.0343(6) Uani 1 1 d . . . C2 C 0.89194(11) 0.16844(8) 0.1923(3) 0.0397(7) Uani 1 1 d . . . C3 C 0.88601(12) 0.16020(8) 0.3316(3) 0.0423(7) Uani 1 1 d . . . H3A H 0.8855 0.1790 0.3958 0.051 Uiso 1 1 calc R . . C4 C 0.88078(11) 0.12452(8) 0.3783(3) 0.0375(6) Uani 1 1 d . . . C5 C 0.88358(12) 0.09621(7) 0.2801(3) 0.0383(6) Uani 1 1 d . . . C6 C 0.88802(11) 0.10489(8) 0.1432(3) 0.0385(6) Uani 1 1 d . . . H6A H 0.8878 0.0862 0.0785 0.046 Uiso 1 1 calc R . . C7 C 0.90188(12) 0.14707(8) -0.0536(3) 0.0402(7) Uani 1 1 d . . . C8 C 0.89726(16) 0.20770(9) 0.1520(4) 0.0567(9) Uani 1 1 d . . . C9 C 0.87036(14) 0.11804(9) 0.5295(3) 0.0480(8) Uani 1 1 d . . . C10 C 0.88691(16) 0.05777(9) 0.3291(4) 0.0590(10) Uani 1 1 d . . . C11 C 0.96137(11) 0.00321(8) 0.0152(3) 0.0419(7) Uani 1 1 d . . . H11A H 0.9539 0.0038 0.1144 0.050 Uiso 1 1 calc R . . C12 C 1.00378(11) 0.02907(8) -0.0174(3) 0.0410(7) Uani 1 1 d . . . H12A H 1.0045 0.0346 -0.1166 0.049 Uiso 1 1 calc R . . C13 C 1.00918(11) 0.06346(9) 0.0659(3) 0.0441(7) Uani 1 1 d . . . C14 C 1.00942(14) 0.06364(10) 0.2093(4) 0.0551(8) Uani 1 1 d . . . H14A H 1.0071 0.0420 0.2585 0.066 Uiso 1 1 calc R . . C15 C 1.01314(14) 0.09639(12) 0.2785(4) 0.0652(11) Uani 1 1 d . . . H15A H 1.0127 0.0969 0.3748 0.078 Uiso 1 1 calc R . . C16 C 1.01866(15) 0.12847(10) 0.0714(5) 0.0637(10) Uani 1 1 d . . . H16A H 1.0228 0.1505 0.0261 0.076 Uiso 1 1 calc R . . C17 C 1.01387(12) 0.09656(9) -0.0033(4) 0.0517(8) Uani 1 1 d . . . H17A H 1.0138 0.0972 -0.0996 0.062 Uiso 1 1 calc R . . C18 C 0.91501(11) 0.00514(9) -0.0680(3) 0.0434(7) Uani 1 1 d . . . C19 C 0.87893(14) -0.02086(10) -0.0435(4) 0.0569(9) Uani 1 1 d . . . H19A H 0.8844 -0.0390 0.0217 0.068 Uiso 1 1 calc R . . C20 C 0.83620(14) -0.02004(12) -0.1134(4) 0.0652(10) Uani 1 1 d . . . H20A H 0.8122 -0.0373 -0.0967 0.078 Uiso 1 1 calc R . . C21 C 0.86198(16) 0.03150(14) -0.2337(5) 0.0761(12) Uani 1 1 d . . . H21A H 0.8557 0.0495 -0.2989 0.091 Uiso 1 1 calc R . . C22 C 0.90615(14) 0.03131(11) -0.1635(4) 0.0637(10) Uani 1 1 d . . . H22A H 0.9295 0.0490 -0.1818 0.076 Uiso 1 1 calc R . . N1 N 1.01725(12) 0.12697(8) 0.2081(4) 0.0617(9) Uani 1 1 d . . . H1A H 1.0191 0.1470 0.2536 0.074 Uiso 1 1 calc R . . N2 N 0.82926(11) 0.00671(9) -0.2090(3) 0.0600(8) Uani 1 1 d . . . H2A H 0.8023 0.0072 -0.2545 0.072 Uiso 1 1 calc R . . 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 0.100(2) 0.0693(16) 0.0276(12) -0.0039(11) 0.0027(12) -0.0328(14) O2 0.111(2) 0.0609(16) 0.0470(14) 0.0146(11) -0.0036(13) -0.0362(16) O3 0.103(2) 0.0360(14) 0.128(3) 0.0211(15) -0.034(2) -0.0031(14) O4 0.086(2) 0.0420(13) 0.091(2) 0.0136(12) -0.0246(15) -0.0219(13) O5 0.0932(19) 0.0909(19) 0.0278(12) -0.0025(12) -0.0001(12) -0.0300(16) O6 0.0754(18) 0.0636(16) 0.0493(14) 0.0001(10) 0.0184(12) -0.0144(13) O7 0.164(3) 0.0345(14) 0.0661(19) 0.0037(13) 0.0235(19) -0.0082(17) O8 0.133(3) 0.0553(17) 0.0706(19) 0.0321(14) 0.0041(17) 0.0228(17) C1 0.0429(15) 0.0261(13) 0.0339(14) -0.0004(11) -0.0006(11) -0.0019(11) C2 0.0527(18) 0.0268(14) 0.0396(16) 0.0027(11) -0.0034(12) 0.0025(12) C3 0.0614(19) 0.0339(15) 0.0317(16) -0.0058(11) 0.0006(12) -0.0014(13) C4 0.0473(17) 0.0348(15) 0.0304(15) -0.0022(12) 0.0075(12) -0.0010(12) C5 0.0521(18) 0.0247(14) 0.0380(17) 0.0060(11) 0.0014(12) -0.0007(12) C6 0.0535(18) 0.0313(15) 0.0306(15) -0.0024(11) 0.0024(12) 0.0010(12) C7 0.0590(19) 0.0323(15) 0.0291(14) 0.0038(11) -0.0082(12) -0.0045(13) C8 0.084(3) 0.0303(16) 0.056(2) 0.0056(13) -0.0067(18) 0.0001(17) C9 0.066(2) 0.0448(18) 0.0337(17) 0.0009(13) 0.0036(14) -0.0066(15) C10 0.087(3) 0.0366(18) 0.053(2) 0.0117(15) 0.0249(18) 0.0080(16) C11 0.0435(17) 0.0429(16) 0.0394(16) -0.0002(12) -0.0009(12) -0.0001(13) C12 0.0458(17) 0.0396(16) 0.0376(15) -0.0033(11) 0.0022(12) 0.0008(13) C13 0.0402(17) 0.0445(17) 0.0475(18) -0.0056(13) 0.0051(12) -0.0007(13) C14 0.064(2) 0.051(2) 0.050(2) -0.0065(15) -0.0018(15) 0.0046(16) C15 0.063(2) 0.076(3) 0.056(2) -0.0260(19) -0.0061(17) 0.0049(19) C16 0.063(3) 0.044(2) 0.083(3) -0.0022(18) -0.0027(18) -0.0046(16) C17 0.052(2) 0.047(2) 0.056(2) -0.0008(14) 0.0004(14) -0.0036(14) C18 0.0443(17) 0.0436(17) 0.0422(16) -0.0041(12) -0.0005(12) 0.0016(13) C19 0.049(2) 0.055(2) 0.066(2) 0.0110(17) -0.0015(16) -0.0099(16) C20 0.048(2) 0.073(3) 0.075(3) 0.002(2) 0.0030(17) -0.0039(17) C21 0.064(3) 0.083(3) 0.081(3) 0.017(2) -0.021(2) 0.002(2) C22 0.057(2) 0.064(2) 0.070(2) 0.0205(18) -0.0173(17) -0.0108(18) N1 0.0561(19) 0.0448(18) 0.084(3) -0.0211(16) -0.0052(15) 0.0021(13) N2 0.0445(17) 0.077(2) 0.0585(19) -0.0126(15) -0.0089(13) 0.0062(15) _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 C7 1.287(4) . ? O1 H1O1 1.0556 . ? O2 C7 1.210(4) . ? O3 C8 1.261(5) . ? O4 C8 1.241(5) . ? O5 C9 1.262(4) . ? O6 C9 1.246(4) . ? O7 C10 1.293(5) . ? O7 H7OH 1.2243 . ? O8 C10 1.192(5) . ? C1 C6 1.376(4) . ? C1 C2 1.400(4) . ? C1 C7 1.494(4) . ? C2 C3 1.389(4) . ? C2 C8 1.507(4) . ? C3 C4 1.399(4) . ? C3 H3A 0.9300 . ? C4 C5 1.413(4) . ? C4 C9 1.506(4) . ? C5 C6 1.366(4) . ? C5 C10 1.498(4) . ? C6 H6A 0.9300 . ? C11 C18 1.507(4) . ? C11 C12 1.538(4) . ? C11 C12 1.560(4) 12_654 ? C11 H11A 0.9800 . ? C12 C13 1.509(4) . ? C12 C11 1.560(4) 12_654 ? C12 H12A 0.9800 . ? C13 C14 1.385(5) . ? C13 C17 1.398(5) . ? C14 C15 1.385(5) . ? C14 H14A 0.9300 . ? C15 N1 1.322(6) . ? C15 H15A 0.9300 . ? C16 N1 1.322(6) . ? C16 C17 1.387(5) . ? C16 H16A 0.9300 . ? C17 H17A 0.9300 . ? C18 C22 1.357(5) . ? C18 C19 1.399(5) . ? C19 C20 1.354(6) . ? C19 H19A 0.9300 . ? C20 N2 1.364(5) . ? C20 H20A 0.9300 . ? C21 N2 1.304(6) . ? C21 C22 1.389(6) . ? C21 H21A 0.9300 . ? C22 H22A 0.9300 . ? N1 H1A 0.8600 . ? N2 H2A 0.8600 . ? 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 C7 O1 H1O1 113.6 . . ? C10 O7 H7OH 117.3 . . ? C6 C1 C2 119.2(3) . . ? C6 C1 C7 119.9(3) . . ? C2 C1 C7 120.8(2) . . ? C3 C2 C1 118.5(3) . . ? C3 C2 C8 118.1(3) . . ? C1 C2 C8 123.3(3) . . ? C2 C3 C4 122.0(3) . . ? C2 C3 H3A 119.0 . . ? C4 C3 H3A 119.0 . . ? C3 C4 C5 118.2(3) . . ? C3 C4 C9 118.8(3) . . ? C5 C4 C9 122.9(3) . . ? C6 C5 C4 118.8(2) . . ? C6 C5 C10 121.5(3) . . ? C4 C5 C10 119.4(3) . . ? C5 C6 C1 123.1(3) . . ? C5 C6 H6A 118.5 . . ? C1 C6 H6A 118.5 . . ? O2 C7 O1 122.5(3) . . ? O2 C7 C1 123.3(3) . . ? O1 C7 C1 114.0(3) . . ? O4 C8 O3 124.8(3) . . ? O4 C8 C2 119.1(3) . . ? O3 C8 C2 115.9(3) . . ? O6 C9 O5 124.6(3) . . ? O6 C9 C4 119.3(3) . . ? O5 C9 C4 115.8(3) . . ? O8 C10 O7 122.5(3) . . ? O8 C10 C5 123.5(4) . . ? O7 C10 C5 113.9(3) . . ? C18 C11 C12 120.1(3) . . ? C18 C11 C12 116.5(2) . 12_654 ? C12 C11 C12 88.2(2) . 12_654 ? C18 C11 H11A 110.1 . . ? C12 C11 H11A 110.1 . . ? C12 C11 H11A 110.1 12_654 . ? C13 C12 C11 119.1(2) . . ? C13 C12 C11 118.3(3) . 12_654 ? C11 C12 C11 87.1(2) . 12_654 ? C13 C12 H12A 110.1 . . ? C11 C12 H12A 110.1 . . ? C11 C12 H12A 110.1 12_654 . ? C14 C13 C17 118.3(3) . . ? C14 C13 C12 122.5(3) . . ? C17 C13 C12 119.3(3) . . ? C15 C14 C13 119.2(4) . . ? C15 C14 H14A 120.4 . . ? C13 C14 H14A 120.4 . . ? N1 C15 C14 120.2(4) . . ? N1 C15 H15A 119.9 . . ? C14 C15 H15A 119.9 . . ? N1 C16 C17 118.8(4) . . ? N1 C16 H16A 120.6 . . ? C17 C16 H16A 120.6 . . ? C16 C17 C13 120.1(3) . . ? C16 C17 H17A 120.0 . . ? C13 C17 H17A 120.0 . . ? C22 C18 C19 118.4(3) . . ? C22 C18 C11 123.2(3) . . ? C19 C18 C11 118.4(3) . . ? C20 C19 C18 120.9(4) . . ? C20 C19 H19A 119.5 . . ? C18 C19 H19A 119.5 . . ? C19 C20 N2 118.3(4) . . ? C19 C20 H20A 120.8 . . ? N2 C20 H20A 120.8 . . ? N2 C21 C22 120.5(4) . . ? N2 C21 H21A 119.7 . . ? C22 C21 H21A 119.7 . . ? C18 C22 C21 119.5(4) . . ? C18 C22 H22A 120.3 . . ? C21 C22 H22A 120.3 . . ? C16 N1 C15 123.5(3) . . ? C16 N1 H1A 118.2 . . ? C15 N1 H1A 118.2 . . ? C21 N2 C20 122.4(3) . . ? C21 N2 H2A 118.8 . . ? C20 N2 H2A 118.8 . . ? loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 0.000 0.561 272 107 ' ' 2 0.000 0.500 1.061 265 102 ' ' 3 0.250 0.250 0.811 272 107 ' ' 4 0.250 0.750 0.311 265 102 ' ' 5 0.500 0.500 0.561 272 107 ' ' 6 0.500 1.000 0.061 265 102 ' ' 7 0.750 0.250 0.311 272 107 ' ' 8 0.750 0.750 0.811 265 102 ' ' _platon_squeeze_details ; Attempts were made to model this disorder or split it into two positions, but were unsuccessful. PLATON/SQUEZZE routine was used to correct the data for the presence of disordered solvent. A potential solvent volume of 2132 3 was found. The stoichiometry of the solvent was calculated to be approximately 5 molecules of water per unit cell, which results in a total of 837 electrons per unit cell. These water molecules was used to calculate expected molecular weight, DXcalc and F(000). ; _diffrn_measured_fraction_theta_max 0.799 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.949 _refine_diff_density_max 0.464 _refine_diff_density_min -0.195 _refine_diff_density_rms 0.048 _vrf_CHEMW03_I ; PROBLEM: ALERT: The ratio of given/expected molecular weight as RESPONSE: See squeeze section ; _vrf_PLAT043_I ; PROBLEM: Check Reported Molecular Weight ................ 526.45 RESPONSE: See squeeze section ; _vrf_PLAT044_I ; PROBLEM: Calculated and Reported Dx Differ .............. ? RESPONSE: See squeeze section ; # end Validation Reply Form # Attachment '- compound2.cif' data_shelxl2 _database_code_depnum_ccdc_archive 'CCDC 831806' #========================================================================== _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H24 N4, 2(C10 H4 O8), 1.28(H2 O)' _chemical_formula_sum 'C44 H34.56 N4 O17.28' _chemical_formula_weight 895.80 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2/n _symmetry_space_group_name_Hall '-P 2yac ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z-1/2' _cell_length_a 11.2070(18) _cell_length_b 10.5278(15) _cell_length_c 17.198(3) _cell_angle_alpha 90.00 _cell_angle_beta 96.718(4) _cell_angle_gamma 90.00 _cell_volume 2015.1(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1125 _cell_measurement_theta_min 2.00 _cell_measurement_theta_max 27.60 _exptl_crystal_description platelet _exptl_crystal_colour 'pale brown' _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.476 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 930 _exptl_absorpt_coefficient_mu 0.116 _exptl_absorpt_correction_type 'Multi Scan' _exptl_absorpt_correction_T_min 0.956 _exptl_absorpt_correction_T_max 0.975 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku AFC7S Mercury' _diffrn_measurement_method '\w ' _diffrn_radiation_detector CCD _diffrn_measurement_device 'Mercury (2x2 bin mode)' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 22622 _diffrn_reflns_av_R_equivalents 0.0373 _diffrn_reflns_av_sigmaI/netI 0.0304 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 27.61 _reflns_number_total 3789 _reflns_number_gt 2868 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_cell_refinement 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_data_reduction 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_structure_solution 'SHELXLTL-NT V5.1 (Bruker AXS, 1998)' _computing_structure_refinement 'SHELXLTL-NT V5.1 (Bruker AXS, 1998)' _computing_molecular_graphics ; SHELXLTL-NT V5.1 (Bruker AXS, 1998) and DIAMOND (Brandenburg, 1998) ; _computing_publication_material ; SHELXLTL-NT V5.1 (Bruker AXS, 1998) and PLATON (Spek, 2003). ; _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0838P)^2^+0.8485P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0050(14) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3789 _refine_ls_number_parameters 302 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0789 _refine_ls_R_factor_gt 0.0581 _refine_ls_wR_factor_ref 0.1665 _refine_ls_wR_factor_gt 0.1503 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.5226(2) 0.2224(2) 0.87962(17) 0.0911(8) Uani 1 1 d . . . O2 O 0.4047(2) 0.15680(19) 0.96377(14) 0.0795(7) Uani 1 1 d . . . H2OH H 0.3676 0.2038 1.0193 0.095 Uiso 1 1 d R . . O3 O 0.7161(2) 0.5885(2) 0.86805(15) 0.0842(7) Uani 1 1 d . . . O4 O 0.6907(2) 0.76771(19) 0.92801(12) 0.0691(6) Uani 1 1 d . . . O7 O 0.3603(2) -0.56897(18) 0.56050(10) 0.0631(6) Uani 1 1 d . . . O8 O 0.33280(18) -0.40667(16) 0.63557(10) 0.0541(5) Uani 1 1 d . . . O9 O 0.39042(17) -0.79479(17) 0.57096(10) 0.0552(5) Uani 1 1 d . . . H1O7 H 0.3738 -0.6825 0.5649 0.089(11) Uiso 1 1 d R . . O10 O 0.3771(2) -0.94435(18) 0.65782(11) 0.0737(7) Uani 1 1 d . . . N1 N 0.48914(19) -0.01643(19) 0.83205(13) 0.0497(5) Uani 1 1 d . . . H1B H 0.4982 0.0594 0.8504 0.060 Uiso 1 1 calc R . . N2 N 0.64358(18) 0.2653(2) 0.49249(11) 0.0452(5) Uani 1 1 d . . . H2B H 0.6332 0.3153 0.4527 0.054 Uiso 1 1 calc R . . C1 C 0.7181(2) 0.0174(2) 0.68690(12) 0.0372(5) Uani 1 1 d . . . H1A H 0.7093 -0.0710 0.6694 0.045 Uiso 1 1 calc R . . C2 C 0.6567(2) 0.0361(2) 0.76230(12) 0.0366(5) Uani 1 1 d . . . H2A H 0.6288 0.1238 0.7661 0.044 Uiso 1 1 calc R . . C3 C 0.5610(2) -0.0555(2) 0.78011(13) 0.0404(5) Uani 1 1 d . . . C4 C 0.4033(3) -0.0899(3) 0.85709(19) 0.0629(8) Uani 1 1 d . . . H4A H 0.3554 -0.0582 0.8933 0.076 Uiso 1 1 calc R . . C5 C 0.3864(3) -0.2100(3) 0.8297(2) 0.0653(8) Uani 1 1 d . . . H5A H 0.3266 -0.2611 0.8463 0.078 Uiso 1 1 calc R . . C6 C 0.4596(3) -0.2551(3) 0.77670(17) 0.0632(8) Uani 1 1 d . . . H6A H 0.4500 -0.3377 0.7578 0.076 Uiso 1 1 calc R . . C7 C 0.5471(3) -0.1778(2) 0.75174(15) 0.0532(7) Uani 1 1 d . . . H7A H 0.5964 -0.2080 0.7159 0.064 Uiso 1 1 calc R . . C8 C 0.6866(2) 0.1053(2) 0.61858(13) 0.0362(5) Uani 1 1 d . . . C9 C 0.6834(2) 0.2370(2) 0.62833(14) 0.0451(6) Uani 1 1 d . . . H9A H 0.6962 0.2720 0.6783 0.054 Uiso 1 1 calc R . . C10 C 0.6612(2) 0.3148(2) 0.56399(15) 0.0467(6) Uani 1 1 d . . . H10A H 0.6586 0.4024 0.5706 0.056 Uiso 1 1 calc R . . C11 C 0.6416(2) 0.1396(2) 0.48084(14) 0.0489(6) Uani 1 1 d . . . H11A H 0.6255 0.1074 0.4303 0.059 Uiso 1 1 calc R . . C12 C 0.6632(2) 0.0580(2) 0.54319(13) 0.0416(6) Uani 1 1 d . . . H12A H 0.6620 -0.0293 0.5348 0.050 Uiso 1 1 calc R . . C13 C 0.4674(3) 0.2419(3) 0.9370(2) 0.0614(8) Uani 1 1 d . . . C14 C 0.4777(2) 0.3739(2) 0.97369(16) 0.0513(7) Uani 1 1 d . . . C15 C 0.5538(2) 0.4558(2) 0.93956(16) 0.0542(7) Uani 1 1 d . . . H15A H 0.5904 0.4250 0.8975 0.065 Uiso 1 1 calc R . . C16 C 0.5798(2) 0.5806(2) 0.96335(15) 0.0501(6) Uani 1 1 d . . . C17 C 0.6686(3) 0.6481(3) 0.91676(17) 0.0575(7) Uani 1 1 d . . . C18 C 0.3603(2) -0.8345(2) 0.63685(15) 0.0467(6) Uani 1 1 d . . . C19 C 0.3020(2) -0.7442(2) 0.69044(13) 0.0375(5) Uani 1 1 d . . . C20 C 0.2969(2) -0.6097(2) 0.68828(12) 0.0357(5) Uani 1 1 d . . . C21 C 0.3341(2) -0.5232(2) 0.62429(13) 0.0401(5) Uani 1 1 d . . . C22 C 0.2500 -0.8046(3) 0.7500 0.0424(8) Uani 1 2 d S . . H22A H 0.2500 -0.8929 0.7500 0.051 Uiso 1 2 calc SR . . C23 C 0.2500 -0.5486(3) 0.7500 0.0355(7) Uani 1 2 d S . . H23A H 0.2500 -0.4603 0.7500 0.043 Uiso 1 2 calc SR . . O1W O 0.6254(8) 0.4676(6) 0.7317(4) 0.197(4) Uani 0.639(9) 1 d P . . H1W1 H 0.5848 0.4073 0.7484 0.236 Uiso 0.639(9) 1 d PR . . H2W1 H 0.6176 0.5218 0.6948 0.236 Uiso 0.639(9) 1 d PR . . 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 0.0938(17) 0.0649(14) 0.124(2) -0.0360(14) 0.0506(16) -0.0176(12) O2 0.0996(18) 0.0523(12) 0.0909(17) -0.0125(11) 0.0288(14) -0.0167(11) O3 0.1026(19) 0.0726(15) 0.0838(17) 0.0034(12) 0.0383(14) -0.0002(13) O4 0.0856(15) 0.0607(13) 0.0604(13) 0.0043(9) 0.0057(11) -0.0192(10) O7 0.1006(16) 0.0530(11) 0.0409(10) -0.0004(8) 0.0307(10) 0.0022(10) O8 0.0857(14) 0.0391(10) 0.0402(10) 0.0050(7) 0.0194(9) 0.0005(8) O9 0.0667(12) 0.0560(11) 0.0450(11) -0.0096(8) 0.0160(9) 0.0093(8) O10 0.1165(19) 0.0490(12) 0.0564(13) -0.0037(9) 0.0130(12) 0.0288(11) N1 0.0525(13) 0.0417(12) 0.0565(13) -0.0021(9) 0.0135(10) -0.0059(9) N2 0.0518(12) 0.0500(13) 0.0347(11) 0.0092(8) 0.0085(9) 0.0021(9) C1 0.0484(14) 0.0323(11) 0.0302(11) -0.0018(8) 0.0021(10) 0.0009(9) C2 0.0463(13) 0.0331(12) 0.0302(12) 0.0001(8) 0.0035(9) -0.0011(9) C3 0.0455(14) 0.0403(13) 0.0343(12) 0.0016(9) -0.0003(10) -0.0029(10) C4 0.0549(18) 0.0591(18) 0.079(2) 0.0031(14) 0.0239(15) -0.0108(13) C5 0.0589(18) 0.0580(18) 0.079(2) 0.0025(15) 0.0078(16) -0.0222(13) C6 0.076(2) 0.0515(17) 0.0586(18) -0.0044(13) -0.0050(16) -0.0241(14) C7 0.0668(18) 0.0480(15) 0.0443(15) -0.0065(11) 0.0041(13) -0.0129(12) C8 0.0363(12) 0.0391(13) 0.0334(12) 0.0006(9) 0.0055(9) 0.0026(9) C9 0.0610(16) 0.0389(13) 0.0336(13) -0.0007(9) -0.0020(11) 0.0009(11) C10 0.0556(15) 0.0387(13) 0.0453(14) 0.0036(10) 0.0034(12) -0.0005(10) C11 0.0631(17) 0.0540(16) 0.0297(13) -0.0015(10) 0.0064(11) 0.0045(12) C12 0.0527(15) 0.0401(13) 0.0325(12) -0.0021(9) 0.0075(10) 0.0053(10) C13 0.0550(17) 0.0518(17) 0.077(2) -0.0073(14) 0.0080(15) 0.0004(13) C14 0.0493(15) 0.0427(14) 0.0599(17) -0.0028(12) -0.0019(13) 0.0043(11) C15 0.0582(17) 0.0495(15) 0.0541(16) -0.0045(12) 0.0032(13) 0.0067(12) C16 0.0501(15) 0.0460(15) 0.0522(16) 0.0019(11) -0.0028(12) 0.0046(11) C17 0.0611(18) 0.0548(17) 0.0548(17) 0.0061(13) -0.0008(14) 0.0021(13) C18 0.0540(15) 0.0446(15) 0.0401(14) -0.0071(10) -0.0004(11) 0.0094(11) C19 0.0425(13) 0.0360(12) 0.0330(12) -0.0033(9) 0.0003(10) 0.0039(9) C20 0.0410(13) 0.0366(12) 0.0291(11) 0.0005(8) 0.0022(9) 0.0002(9) C21 0.0461(14) 0.0431(14) 0.0318(12) 0.0018(9) 0.0076(10) 0.0011(10) C22 0.056(2) 0.0322(17) 0.0379(18) 0.000 -0.0006(15) 0.000 C23 0.0450(18) 0.0322(16) 0.0296(16) 0.000 0.0056(13) 0.000 O1W 0.367(11) 0.118(5) 0.120(5) -0.038(4) 0.094(6) -0.008(5) _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 1.241(4) . ? O2 C13 1.259(4) . ? O2 H2OH 1.1926 . ? O3 C17 1.218(3) . ? O4 C17 1.294(3) . ? O7 C21 1.264(3) . ? O7 H1O7 1.2063 . ? O8 C21 1.243(3) . ? O9 C18 1.289(3) . ? O9 H1O7 1.1992 . ? O10 C18 1.220(3) . ? N1 C3 1.336(3) . ? N1 C4 1.343(3) . ? N1 H1B 0.8600 . ? N2 C10 1.329(3) . ? N2 C11 1.338(3) . ? N2 H2B 0.8600 . ? C1 C8 1.505(3) . ? C1 C2 1.550(3) . ? C1 C2 1.576(3) 2_656 ? C1 H1A 0.9800 . ? C2 C3 1.500(3) . ? C2 C1 1.576(3) 2_656 ? C2 H2A 0.9800 . ? C3 C7 1.379(3) . ? C4 C5 1.355(4) . ? C4 H4A 0.9300 . ? C5 C6 1.380(4) . ? C5 H5A 0.9300 . ? C6 C7 1.381(4) . ? C6 H6A 0.9300 . ? C7 H7A 0.9300 . ? C8 C12 1.385(3) . ? C8 C9 1.397(3) . ? C9 C10 1.376(3) . ? C9 H9A 0.9300 . ? C10 H10A 0.9300 . ? C11 C12 1.373(3) . ? C11 H11A 0.9300 . ? C12 H12A 0.9300 . ? C13 C14 1.525(4) . ? C14 C15 1.390(4) . ? C14 C16 1.407(4) 3_667 ? C15 C16 1.397(4) . ? C15 H15A 0.9300 . ? C16 C14 1.407(4) 3_667 ? C16 C17 1.524(4) . ? C18 C19 1.524(3) . ? C19 C22 1.390(3) . ? C19 C20 1.417(3) . ? C20 C23 1.395(3) . ? C20 C21 1.523(3) . ? C22 C19 1.390(3) 2_556 ? C22 H22A 0.9300 . ? C23 C20 1.395(3) 2_556 ? C23 H23A 0.9300 . ? O1W H1W1 0.8500 . ? O1W H2W1 0.8501 . ? 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 O2 H2OH 105.0 . . ? C21 O7 H1O7 111.3 . . ? C18 O9 H1O7 110.0 . . ? C3 N1 C4 123.2(2) . . ? C3 N1 H1B 118.4 . . ? C4 N1 H1B 118.4 . . ? C10 N2 C11 121.6(2) . . ? C10 N2 H2B 119.2 . . ? C11 N2 H2B 119.2 . . ? C8 C1 C2 119.29(18) . . ? C8 C1 C2 117.92(18) . 2_656 ? C2 C1 C2 88.52(16) . 2_656 ? C8 C1 H1A 109.8 . . ? C2 C1 H1A 109.8 . . ? C2 C1 H1A 109.8 2_656 . ? C3 C2 C1 119.17(18) . . ? C3 C2 C1 114.72(18) . 2_656 ? C1 C2 C1 89.67(16) . 2_656 ? C3 C2 H2A 110.6 . . ? C1 C2 H2A 110.6 . . ? C1 C2 H2A 110.6 2_656 . ? N1 C3 C7 118.2(2) . . ? N1 C3 C2 116.1(2) . . ? C7 C3 C2 125.6(2) . . ? N1 C4 C5 120.1(3) . . ? N1 C4 H4A 119.9 . . ? C5 C4 H4A 119.9 . . ? C4 C5 C6 118.8(3) . . ? C4 C5 H5A 120.6 . . ? C6 C5 H5A 120.6 . . ? C5 C6 C7 120.1(3) . . ? C5 C6 H6A 120.0 . . ? C7 C6 H6A 120.0 . . ? C3 C7 C6 119.7(3) . . ? C3 C7 H7A 120.1 . . ? C6 C7 H7A 120.1 . . ? C12 C8 C9 117.7(2) . . ? C12 C8 C1 120.75(19) . . ? C9 C8 C1 121.6(2) . . ? C10 C9 C8 119.9(2) . . ? C10 C9 H9A 120.0 . . ? C8 C9 H9A 120.0 . . ? N2 C10 C9 120.3(2) . . ? N2 C10 H10A 119.9 . . ? C9 C10 H10A 119.9 . . ? N2 C11 C12 120.2(2) . . ? N2 C11 H11A 119.9 . . ? C12 C11 H11A 119.9 . . ? C11 C12 C8 120.2(2) . . ? C11 C12 H12A 119.9 . . ? C8 C12 H12A 119.9 . . ? O1 C13 O2 121.6(3) . . ? O1 C13 C14 117.4(3) . . ? O2 C13 C14 121.0(3) . . ? C15 C14 C16 118.2(2) . 3_667 ? C15 C14 C13 114.2(2) . . ? C16 C14 C13 127.5(3) 3_667 . ? C14 C15 C16 125.2(3) . . ? C14 C15 H15A 117.4 . . ? C16 C15 H15A 117.4 . . ? C15 C16 C14 116.6(3) . 3_667 ? C15 C16 C17 114.3(2) . . ? C14 C16 C17 129.2(2) 3_667 . ? O3 C17 O4 120.8(3) . . ? O3 C17 C16 119.1(3) . . ? O4 C17 C16 120.1(3) . . ? O10 C18 O9 121.3(2) . . ? O10 C18 C19 118.4(2) . . ? O9 C18 C19 120.3(2) . . ? C22 C19 C20 117.2(2) . . ? C22 C19 C18 114.0(2) . . ? C20 C19 C18 128.7(2) . . ? C23 C20 C19 117.2(2) . . ? C23 C20 C21 115.7(2) . . ? C19 C20 C21 127.04(19) . . ? O8 C21 O7 121.3(2) . . ? O8 C21 C20 117.91(19) . . ? O7 C21 C20 120.7(2) . . ? C19 C22 C19 125.6(3) 2_556 . ? C19 C22 H22A 117.2 2_556 . ? C19 C22 H22A 117.2 . . ? C20 C23 C20 125.1(3) 2_556 . ? C20 C23 H23A 117.4 2_556 . ? C20 C23 H23A 117.4 . . ? H1W1 O1W H2W1 137.9 . . ? _diffrn_measured_fraction_theta_max 0.808 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.962 _refine_diff_density_max 0.414 _refine_diff_density_min -0.309 _refine_diff_density_rms 0.051 # Attachment '- compound3.cif' data_shelxl3 _database_code_depnum_ccdc_archive 'CCDC 831807' #========================================================================== _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C26 H20 Cl2 N2), C10 H6 O8, 0.62(H2 O)' _chemical_formula_sum 'C62 H47.24 Cl4 N4 O8.62' _chemical_formula_weight 1128.00 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' Cl Cl 0.1484 0.1585 '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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.254(3) _cell_length_b 10.381(3) _cell_length_c 13.085(5) _cell_angle_alpha 86.63(3) _cell_angle_beta 87.56(3) _cell_angle_gamma 75.388(17) _cell_volume 1344.9(7) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 906 _cell_measurement_theta_min 2.00 _cell_measurement_theta_max 27.66 _exptl_crystal_description Prism _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.393 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 0.284 _exptl_absorpt_correction_type 'Multi Scan' _exptl_absorpt_correction_T_min 0.960 _exptl_absorpt_correction_T_max 0.975 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku AFC7S Mercury' _diffrn_measurement_method '\w ' _diffrn_radiation_detector CCD _diffrn_measurement_device 'Mercury (2x2 bin mode)' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 14998 _diffrn_reflns_av_R_equivalents 0.0244 _diffrn_reflns_av_sigmaI/netI 0.0299 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.56 _diffrn_reflns_theta_max 27.66 _reflns_number_total 4899 _reflns_number_gt 4015 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_cell_refinement 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_data_reduction 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_structure_solution 'SHELXLTL-NT V5.1 (Bruker AXS, 1998)' _computing_structure_refinement 'SHELXLTL-NT V5.1 (Bruker AXS, 1998)' _computing_molecular_graphics ; SHELXLTL-NT V5.1 (Bruker AXS, 1998) and DIAMOND (Brandenburg, 1998) ; _computing_publication_material ; SHELXLTL-NT V5.1 (Bruker AXS, 1998) and PLATON (Spek, 2003). ; _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0796P)^2^+0.5034P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4899 _refine_ls_number_parameters 359 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0649 _refine_ls_R_factor_gt 0.0524 _refine_ls_wR_factor_ref 0.1538 _refine_ls_wR_factor_gt 0.1413 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _refine_ls_shift/su_max 0.003 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.69043(9) -0.64673(6) -0.26677(6) 0.0749(3) Uani 1 1 d . . . Cl2 Cl 0.21633(10) 0.62874(7) -0.45124(7) 0.0845(3) Uani 1 1 d . . . N1 N 0.5521(2) 0.2191(2) -0.04369(14) 0.0468(5) Uani 1 1 d . . . N2 N 0.1827(2) 0.05203(19) -0.66151(14) 0.0457(5) Uani 1 1 d . . . O1 O 0.93691(19) 0.2455(2) 0.18828(19) 0.0943(9) Uani 1 1 d . . . O2 O 1.15630(16) 0.21020(18) 0.16306(13) 0.0583(5) Uani 1 1 d . . . H2OH H 1.1600 0.1495 0.2101 0.070 Uiso 1 1 d R . . O3 O 0.69362(17) 0.38449(18) -0.00509(12) 0.0536(4) Uani 1 1 d . . . H1O3 H 0.6517 0.3256 -0.0149 0.064 Uiso 1 1 d R . . O4 O 0.8660(3) 0.2113(2) -0.0294(3) 0.1304(13) Uani 1 1 d . . . C1 C 1.0316(2) 0.2728(2) 0.14462(17) 0.0435(5) Uani 1 1 d . . . C2 C 1.0182(2) 0.3862(2) 0.06635(15) 0.0363(5) Uani 1 1 d . . . C3 C 0.9110(2) 0.4177(2) -0.00169(16) 0.0379(5) Uani 1 1 d . . . C4 C 0.8198(3) 0.3266(3) -0.0115(2) 0.0544(6) Uani 1 1 d . . . C5 C 1.1056(2) 0.4690(2) 0.06679(15) 0.0381(5) Uani 1 1 d . . . H5A H 1.1767 0.4481 0.1116 0.046 Uiso 1 1 calc R . . C6 C 0.3754(2) -0.0714(2) -0.29148(15) 0.0350(4) Uani 1 1 d . . . H6A H 0.4321 -0.0209 -0.3297 0.042 Uiso 1 1 calc R . . C7 C 0.3142(2) 0.0065(2) -0.19517(15) 0.0365(5) Uani 1 1 d . . . H7A H 0.2805 -0.0538 -0.1464 0.044 Uiso 1 1 calc R . . C8 C 0.1937(2) 0.0896(2) -0.26041(16) 0.0396(5) Uani 1 1 d . . . H8A H 0.1067 0.0942 -0.2250 0.048 Uiso 1 1 calc R . . C9 C 0.2309(2) -0.0274(2) -0.33554(15) 0.0372(5) Uani 1 1 d . . . H9A H 0.1818 -0.0940 -0.3126 0.045 Uiso 1 1 calc R . . C10 C 0.4522(2) -0.2154(2) -0.28370(15) 0.0361(5) Uani 1 1 d . . . C11 C 0.5771(2) -0.2563(2) -0.33340(19) 0.0472(5) Uani 1 1 d . . . H11A H 0.6123 -0.1934 -0.3710 0.057 Uiso 1 1 calc R . . C12 C 0.6508(3) -0.3883(2) -0.3287(2) 0.0535(6) Uani 1 1 d . . . H12A H 0.7341 -0.4139 -0.3627 0.064 Uiso 1 1 calc R . . C13 C 0.5982(3) -0.4804(2) -0.27271(17) 0.0483(6) Uani 1 1 d . . . C14 C 0.4752(3) -0.4438(2) -0.2232(2) 0.0577(7) Uani 1 1 d . . . H14A H 0.4407 -0.5074 -0.1858 0.069 Uiso 1 1 calc R . . C15 C 0.4021(3) -0.3117(2) -0.22884(18) 0.0490(6) Uani 1 1 d . . . H15A H 0.3183 -0.2874 -0.1954 0.059 Uiso 1 1 calc R . . C16 C 0.2140(2) -0.0002(2) -0.44911(16) 0.0370(5) Uani 1 1 d . . . C17 C 0.3032(2) -0.0723(2) -0.51979(16) 0.0423(5) Uani 1 1 d . . . H17A H 0.3760 -0.1397 -0.4974 0.051 Uiso 1 1 calc R . . C18 C 0.2843(2) -0.0445(2) -0.62369(17) 0.0454(5) Uani 1 1 d . . . H18A H 0.3452 -0.0953 -0.6694 0.055 Uiso 1 1 calc R . . C19 C 0.0951(2) 0.1202(2) -0.59313(18) 0.0482(6) Uani 1 1 d . . . H19A H 0.0227 0.1867 -0.6175 0.058 Uiso 1 1 calc R . . C20 C 0.1062(2) 0.0971(2) -0.48857(17) 0.0472(5) Uani 1 1 d . . . H20A H 0.0416 0.1466 -0.4445 0.057 Uiso 1 1 calc R . . C21 C 0.2039(2) 0.2248(2) -0.30421(16) 0.0400(5) Uani 1 1 d . . . C22 C 0.0919(3) 0.3326(3) -0.3004(2) 0.0618(7) Uani 1 1 d . . . H22A H 0.0133 0.3212 -0.2672 0.074 Uiso 1 1 calc R . . C23 C 0.0939(3) 0.4566(3) -0.3447(3) 0.0736(9) Uani 1 1 d . . . H23A H 0.0171 0.5270 -0.3422 0.088 Uiso 1 1 calc R . . C24 C 0.2105(3) 0.4746(2) -0.3924(2) 0.0564(6) Uani 1 1 d . . . C25 C 0.3240(3) 0.3722(2) -0.3951(2) 0.0544(6) Uani 1 1 d . . . H25A H 0.4034 0.3855 -0.4259 0.065 Uiso 1 1 calc R . . C26 C 0.3198(2) 0.2487(2) -0.35165(19) 0.0509(6) Uani 1 1 d . . . H26A H 0.3974 0.1792 -0.3542 0.061 Uiso 1 1 calc R . . C27 C 0.3978(2) 0.0776(2) -0.13884(15) 0.0364(5) Uani 1 1 d . . . C28 C 0.5366(2) 0.0326(2) -0.13562(15) 0.0401(5) Uani 1 1 d . . . H28A H 0.5804 -0.0465 -0.1654 0.048 Uiso 1 1 calc R . . C29 C 0.6100(2) 0.1054(2) -0.08802(17) 0.0460(5) Uani 1 1 d . . . H29A H 0.7033 0.0740 -0.0868 0.055 Uiso 1 1 calc R . . C30 C 0.4174(2) 0.2608(2) -0.04232(17) 0.0482(6) Uani 1 1 d . . . H30A H 0.3762 0.3381 -0.0092 0.058 Uiso 1 1 calc R . . C31 C 0.3375(2) 0.1933(2) -0.08823(16) 0.0447(5) Uani 1 1 d . . . H31A H 0.2441 0.2247 -0.0855 0.054 Uiso 1 1 calc R . . O1W O 0.0950(2) 0.0444(2) -0.02536(16) 0.117(5) Uani 0.310(8) 1 d PR . . 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 Cl1 0.1004(6) 0.0406(4) 0.0702(5) 0.0036(3) 0.0067(4) 0.0047(3) Cl2 0.1121(7) 0.0386(4) 0.0935(6) 0.0102(4) 0.0041(5) -0.0062(4) N1 0.0528(12) 0.0526(12) 0.0418(10) -0.0025(9) -0.0030(8) -0.0257(9) N2 0.0525(12) 0.0446(11) 0.0420(10) 0.0064(9) -0.0102(8) -0.0166(9) O1 0.0439(11) 0.1098(18) 0.1200(18) 0.0725(15) -0.0047(11) -0.0193(11) O2 0.0439(10) 0.0641(11) 0.0600(10) 0.0272(9) -0.0070(8) -0.0066(8) O3 0.0491(10) 0.0653(11) 0.0581(10) -0.0086(8) -0.0044(8) -0.0340(9) O4 0.0865(18) 0.0419(12) 0.270(4) -0.0049(17) -0.081(2) -0.0167(11) C1 0.0384(12) 0.0481(13) 0.0446(12) 0.0092(10) -0.0078(9) -0.0137(10) C2 0.0341(11) 0.0395(11) 0.0351(10) 0.0016(9) -0.0037(8) -0.0093(9) C3 0.0367(11) 0.0398(11) 0.0393(11) 0.0009(9) -0.0069(8) -0.0131(9) C4 0.0570(16) 0.0473(14) 0.0651(15) 0.0149(12) -0.0252(12) -0.0249(12) C5 0.0349(11) 0.0439(12) 0.0367(10) 0.0031(9) -0.0096(8) -0.0118(9) C6 0.0381(11) 0.0352(10) 0.0339(10) 0.0001(8) -0.0052(8) -0.0131(8) C7 0.0376(11) 0.0396(11) 0.0348(10) 0.0001(9) -0.0031(8) -0.0143(9) C8 0.0340(11) 0.0459(12) 0.0400(11) -0.0019(10) -0.0023(8) -0.0120(9) C9 0.0376(11) 0.0392(11) 0.0377(11) 0.0016(9) -0.0056(8) -0.0153(9) C10 0.0399(12) 0.0363(11) 0.0345(10) -0.0011(9) -0.0077(8) -0.0130(9) C11 0.0464(13) 0.0387(12) 0.0586(14) -0.0018(11) 0.0034(10) -0.0155(10) C12 0.0489(14) 0.0471(14) 0.0617(15) -0.0055(12) 0.0056(11) -0.0075(11) C13 0.0640(16) 0.0372(12) 0.0411(12) -0.0005(10) -0.0059(10) -0.0075(10) C14 0.0712(18) 0.0431(13) 0.0566(15) 0.0116(12) 0.0066(13) -0.0146(12) C15 0.0530(14) 0.0424(12) 0.0494(13) 0.0060(11) 0.0070(10) -0.0110(10) C16 0.0406(12) 0.0339(10) 0.0406(11) 0.0013(9) -0.0082(9) -0.0167(9) C17 0.0477(13) 0.0371(11) 0.0418(11) 0.0049(10) -0.0082(9) -0.0102(9) C18 0.0526(14) 0.0410(12) 0.0427(12) 0.0012(10) -0.0025(10) -0.0123(10) C19 0.0473(13) 0.0461(13) 0.0503(13) 0.0055(11) -0.0162(10) -0.0097(10) C20 0.0429(13) 0.0515(13) 0.0466(12) -0.0029(11) -0.0087(10) -0.0097(10) C21 0.0389(12) 0.0394(11) 0.0412(11) -0.0057(9) -0.0071(9) -0.0069(9) C22 0.0479(15) 0.0489(14) 0.0829(19) -0.0075(14) 0.0084(13) -0.0020(11) C23 0.0615(18) 0.0405(14) 0.108(2) -0.0008(15) 0.0027(16) 0.0063(12) C24 0.0720(18) 0.0365(12) 0.0567(14) -0.0012(11) -0.0056(12) -0.0061(12) C25 0.0556(15) 0.0446(13) 0.0611(15) 0.0033(12) 0.0017(11) -0.0110(11) C26 0.0436(13) 0.0399(12) 0.0643(15) 0.0069(11) 0.0002(11) -0.0040(10) C27 0.0412(12) 0.0395(11) 0.0302(10) 0.0042(9) -0.0033(8) -0.0141(9) C28 0.0418(12) 0.0427(12) 0.0359(10) 0.0003(9) -0.0043(9) -0.0106(9) C29 0.0403(12) 0.0576(15) 0.0422(12) 0.0017(11) -0.0052(9) -0.0166(11) C30 0.0527(15) 0.0488(13) 0.0471(12) -0.0096(11) -0.0015(10) -0.0183(11) C31 0.0410(13) 0.0493(13) 0.0459(12) -0.0073(10) -0.0023(9) -0.0136(10) O1W 0.090(7) 0.093(6) 0.152(9) -0.003(6) 0.044(6) -0.003(5) _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 Cl1 C13 1.746(2) . ? Cl2 C24 1.748(3) . ? N1 C29 1.334(3) . ? N1 C30 1.338(3) . ? N2 C18 1.339(3) . ? N2 C19 1.339(3) . ? O1 C1 1.192(3) . ? O2 C1 1.305(3) . ? O2 H2OH 0.8499 . ? O3 C4 1.283(3) . ? O3 H1O3 0.8500 . ? O4 C4 1.203(3) . ? C1 C2 1.497(3) . ? C2 C5 1.390(3) . ? C2 C3 1.405(3) . ? C3 C5 1.390(3) 2_765 ? C3 C4 1.502(3) . ? C5 C3 1.390(3) 2_765 ? C5 H5A 0.9300 . ? C6 C10 1.503(3) . ? C6 C7 1.559(3) . ? C6 C9 1.561(3) . ? C6 H6A 0.9800 . ? C7 C27 1.504(3) . ? C7 C8 1.570(3) . ? C7 H7A 0.9800 . ? C8 C21 1.511(3) . ? C8 C9 1.569(3) . ? C8 H8A 0.9800 . ? C9 C16 1.505(3) . ? C9 H9A 0.9800 . ? C10 C15 1.387(3) . ? C10 C11 1.389(3) . ? C11 C12 1.387(3) . ? C11 H11A 0.9300 . ? C12 C13 1.373(3) . ? C12 H12A 0.9300 . ? C13 C14 1.369(4) . ? C14 C15 1.386(3) . ? C14 H14A 0.9300 . ? C15 H15A 0.9300 . ? C16 C17 1.384(3) . ? C16 C20 1.390(3) . ? C17 C18 1.385(3) . ? C17 H17A 0.9300 . ? C18 H18A 0.9300 . ? C19 C20 1.380(3) . ? C19 H19A 0.9300 . ? C20 H20A 0.9300 . ? C21 C22 1.388(3) . ? C21 C26 1.389(3) . ? C22 C23 1.385(4) . ? C22 H22A 0.9300 . ? C23 C24 1.375(4) . ? C23 H23A 0.9300 . ? C24 C25 1.364(4) . ? C25 C26 1.382(3) . ? C25 H25A 0.9300 . ? C26 H26A 0.9300 . ? C27 C28 1.383(3) . ? C27 C31 1.395(3) . ? C28 C29 1.382(3) . ? C28 H28A 0.9300 . ? C29 H29A 0.9300 . ? C30 C31 1.380(3) . ? C30 H30A 0.9300 . ? C31 H31A 0.9300 . ? 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 C29 N1 C30 118.3(2) . . ? C18 N2 C19 116.52(19) . . ? C1 O2 H2OH 111.0 . . ? C4 O3 H1O3 106.5 . . ? O1 C1 O2 123.4(2) . . ? O1 C1 C2 122.8(2) . . ? O2 C1 C2 113.74(18) . . ? C5 C2 C3 119.17(19) . . ? C5 C2 C1 119.62(18) . . ? C3 C2 C1 120.95(18) . . ? C5 C3 C2 119.36(19) 2_765 . ? C5 C3 C4 118.90(18) 2_765 . ? C2 C3 C4 121.58(19) . . ? O4 C4 O3 125.1(2) . . ? O4 C4 C3 120.5(2) . . ? O3 C4 C3 114.3(2) . . ? C2 C5 C3 121.47(19) . 2_765 ? C2 C5 H5A 119.3 . . ? C3 C5 H5A 119.3 2_765 . ? C10 C6 C7 122.02(17) . . ? C10 C6 C9 121.63(17) . . ? C7 C6 C9 86.68(15) . . ? C10 C6 H6A 108.2 . . ? C7 C6 H6A 108.2 . . ? C9 C6 H6A 108.2 . . ? C27 C7 C6 119.67(17) . . ? C27 C7 C8 119.54(18) . . ? C6 C7 C8 89.73(15) . . ? C27 C7 H7A 108.8 . . ? C6 C7 H7A 108.8 . . ? C8 C7 H7A 108.8 . . ? C21 C8 C9 116.35(17) . . ? C21 C8 C7 117.19(17) . . ? C9 C8 C7 86.06(15) . . ? C21 C8 H8A 111.6 . . ? C9 C8 H8A 111.6 . . ? C7 C8 H8A 111.6 . . ? C16 C9 C6 119.73(17) . . ? C16 C9 C8 120.66(17) . . ? C6 C9 C8 89.69(15) . . ? C16 C9 H9A 108.4 . . ? C6 C9 H9A 108.4 . . ? C8 C9 H9A 108.4 . . ? C15 C10 C11 117.6(2) . . ? C15 C10 C6 122.2(2) . . ? C11 C10 C6 120.15(18) . . ? C12 C11 C10 122.0(2) . . ? C12 C11 H11A 119.0 . . ? C10 C11 H11A 119.0 . . ? C13 C12 C11 118.6(2) . . ? C13 C12 H12A 120.7 . . ? C11 C12 H12A 120.7 . . ? C14 C13 C12 121.1(2) . . ? C14 C13 Cl1 120.13(19) . . ? C12 C13 Cl1 118.8(2) . . ? C13 C14 C15 119.8(2) . . ? C13 C14 H14A 120.1 . . ? C15 C14 H14A 120.1 . . ? C14 C15 C10 120.9(2) . . ? C14 C15 H15A 119.5 . . ? C10 C15 H15A 119.5 . . ? C17 C16 C20 116.4(2) . . ? C17 C16 C9 121.88(19) . . ? C20 C16 C9 121.7(2) . . ? C16 C17 C18 120.3(2) . . ? C16 C17 H17A 119.9 . . ? C18 C17 H17A 119.9 . . ? N2 C18 C17 123.2(2) . . ? N2 C18 H18A 118.4 . . ? C17 C18 H18A 118.4 . . ? N2 C19 C20 123.6(2) . . ? N2 C19 H19A 118.2 . . ? C20 C19 H19A 118.2 . . ? C19 C20 C16 119.9(2) . . ? C19 C20 H20A 120.0 . . ? C16 C20 H20A 120.0 . . ? C22 C21 C26 116.5(2) . . ? C22 C21 C8 119.7(2) . . ? C26 C21 C8 123.71(19) . . ? C23 C22 C21 121.9(3) . . ? C23 C22 H22A 119.1 . . ? C21 C22 H22A 119.1 . . ? C24 C23 C22 119.3(2) . . ? C24 C23 H23A 120.3 . . ? C22 C23 H23A 120.3 . . ? C25 C24 C23 120.6(2) . . ? C25 C24 Cl2 118.7(2) . . ? C23 C24 Cl2 120.7(2) . . ? C24 C25 C26 119.3(2) . . ? C24 C25 H25A 120.3 . . ? C26 C25 H25A 120.3 . . ? C25 C26 C21 122.3(2) . . ? C25 C26 H26A 118.9 . . ? C21 C26 H26A 118.9 . . ? C28 C27 C31 117.3(2) . . ? C28 C27 C7 121.8(2) . . ? C31 C27 C7 120.82(19) . . ? C29 C28 C27 119.8(2) . . ? C29 C28 H28A 120.1 . . ? C27 C28 H28A 120.1 . . ? N1 C29 C28 122.4(2) . . ? N1 C29 H29A 118.8 . . ? C28 C29 H29A 118.8 . . ? N1 C30 C31 122.4(2) . . ? N1 C30 H30A 118.8 . . ? C31 C30 H30A 118.8 . . ? C30 C31 C27 119.5(2) . . ? C30 C31 H31A 120.3 . . ? C27 C31 H31A 120.3 . . ? _diffrn_measured_fraction_theta_max 0.779 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.957 _refine_diff_density_max 0.515 _refine_diff_density_min -0.397 _refine_diff_density_rms 0.050