# Electronic Supplementary Material (ESI) for CrystEngComm # 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_al74 _database_code_depnum_ccdc_archive 'CCDC 904819' # start Validation Reply Form _vrf_PLAT926_al74 ; PROBLEM: PLAT926_ALERT_1_B Reported and Calculated R1 Differ by ......... -0.0104 RESPONSE: CIF and FCF both originate from the last SHELXL cycle. This is a false alert as PLATON cannot handle twinned fcf. ; _vrf_PLAT927_al74 ; PROBLEM: PLAT927_ALERT_1_B Reported and Calculated wR2 Differ by ......... -0.0312 RESPONSE: CIF and FCF both originate from the last SHELXL cycle. This is a false alert as PLATON cannot handle twinned fcf. ; _vrf_PLAT928_al74 ; PROBLEM: PLAT928_ALERT_1_B Reported and Calculated S value Differ by . -0.211 RESPONSE: CIF and FCF both originate from the last SHELXL cycle. This is a false alert as PLATON cannot handle twinned fcf. ; # end Validation Reply Form _audit_creation_method SHELXL-97 _chemical_name_systematic ; Aripiprazole hydrochloride salt ; _chemical_name_common 'Aripiprazole hydrochloride salt' _chemical_melting_point ? _chemical_formula_moiety 'C23 H28 Cl2 N3 O2, Cl' _chemical_formula_sum 'C23 H28 Cl3 N3 O2' _chemical_formula_weight 484.83 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' Cl Cl 0.1484 0.1585 '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(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.2891(12) _cell_length_b 28.065(3) _cell_length_c 7.9247(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.885(2) _cell_angle_gamma 90.00 _cell_volume 2288.1(5) _cell_formula_units_Z 4 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 3239 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 24.46 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.407 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1016 _exptl_absorpt_coefficient_mu 0.427 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8479 _exptl_absorpt_correction_T_max 0.9749 _exptl_absorpt_process_details 'Bruker AXS SADABS program' _exptl_special_details ; Sheldrick,G.M.,(2003),University of gottingen,Germany ; _diffrn_ambient_temperature 294(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12367 _diffrn_reflns_av_R_equivalents 0.0331 _diffrn_reflns_av_sigmaI/netI 0.0394 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_k_max 33 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 24.99 _reflns_number_total 4029 _reflns_number_gt 3370 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0511P)^2^+3.9863P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4029 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0756 _refine_ls_R_factor_gt 0.0627 _refine_ls_wR_factor_ref 0.1504 _refine_ls_wR_factor_gt 0.1420 _refine_ls_goodness_of_fit_ref 1.101 _refine_ls_restrained_S_all 1.101 _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 C1 C 1.0356(4) -0.21010(14) 1.6360(5) 0.0352(9) Uani 1 1 d . . . C2 C 1.0205(5) -0.17325(15) 1.7702(5) 0.0438(10) Uani 1 1 d . . . H2A H 1.0689 -0.1831 1.8702 0.053 Uiso 1 1 calc R . . H2B H 0.9296 -0.1711 1.7997 0.053 Uiso 1 1 calc R . . C3 C 1.0680(4) -0.12415(15) 1.7160(5) 0.0408(10) Uani 1 1 d . . . H3A H 1.0427 -0.1005 1.7985 0.049 Uiso 1 1 calc R . . H3B H 1.1621 -0.1242 1.7099 0.049 Uiso 1 1 calc R . . C4 C 1.0104(4) -0.11181(13) 1.5473(5) 0.0350(9) Uani 1 1 d . . . C5 C 0.9934(4) -0.14808(12) 1.4284(5) 0.0301(8) Uani 1 1 d . . . C6 C 0.9438(4) -0.13946(13) 1.2693(5) 0.0313(8) Uani 1 1 d . . . H6 H 0.9369 -0.1641 1.1913 0.038 Uiso 1 1 calc R . . C7 C 0.9041(4) -0.09371(13) 1.2256(5) 0.0330(9) Uani 1 1 d . . . C8 C 0.9178(4) -0.05683(14) 1.3401(5) 0.0414(10) Uani 1 1 d . . . H8 H 0.8912 -0.0261 1.3118 0.050 Uiso 1 1 calc R . . C9 C 0.9714(4) -0.06634(14) 1.4971(5) 0.0421(10) Uani 1 1 d . . . H9 H 0.9821 -0.0413 1.5728 0.051 Uiso 1 1 calc R . . C10 C 0.8190(4) -0.04274(14) 1.0045(6) 0.0431(10) Uani 1 1 d . . . H10A H 0.8990 -0.0248 0.9926 0.052 Uiso 1 1 calc R . . H10B H 0.7629 -0.0256 1.0808 0.052 Uiso 1 1 calc R . . C11 C 0.7530(5) -0.04898(15) 0.8360(5) 0.0461(11) Uani 1 1 d . . . H11A H 0.6680 -0.0630 0.8525 0.055 Uiso 1 1 calc R . . H11B H 0.8034 -0.0710 0.7689 0.055 Uiso 1 1 calc R . . C12 C 0.7368(5) -0.00240(16) 0.7390(6) 0.0515(12) Uani 1 1 d . . . H12A H 0.8180 0.0151 0.7435 0.062 Uiso 1 1 calc R . . H12B H 0.7169 -0.0095 0.6216 0.062 Uiso 1 1 calc R . . C13 C 0.6306(4) 0.02817(14) 0.8092(5) 0.0415(10) Uani 1 1 d . . . H13A H 0.6600 0.0416 0.9159 0.050 Uiso 1 1 calc R . . H13B H 0.5553 0.0084 0.8310 0.050 Uiso 1 1 calc R . . C14 C 0.6811(4) 0.11009(14) 0.6993(5) 0.0359(9) Uani 1 1 d . . . H14A H 0.7678 0.1003 0.6676 0.043 Uiso 1 1 calc R . . H14B H 0.6856 0.1223 0.8137 0.043 Uiso 1 1 calc R . . C15 C 0.6326(4) 0.14881(14) 0.5804(5) 0.0356(9) Uani 1 1 d . . . H15A H 0.6918 0.1757 0.5840 0.043 Uiso 1 1 calc R . . H15B H 0.6291 0.1367 0.4657 0.043 Uiso 1 1 calc R . . C16 C 0.4131(4) 0.12395(13) 0.6134(6) 0.0388(10) Uani 1 1 d . . . H16A H 0.4111 0.1132 0.4970 0.047 Uiso 1 1 calc R . . H16B H 0.3260 0.1339 0.6428 0.047 Uiso 1 1 calc R . . C17 C 0.4563(4) 0.08355(14) 0.7272(6) 0.0394(10) Uani 1 1 d . . . H17A H 0.4515 0.0937 0.8439 0.047 Uiso 1 1 calc R . . H17B H 0.3978 0.0568 0.7117 0.047 Uiso 1 1 calc R . . C18 C 0.4539(4) 0.20872(13) 0.5793(5) 0.0321(8) Uani 1 1 d . . . C19 C 0.5160(4) 0.25149(13) 0.6265(5) 0.0325(8) Uani 1 1 d . . . C20 C 0.4617(4) 0.29512(13) 0.5839(5) 0.0351(9) Uani 1 1 d . . . C21 C 0.3449(4) 0.29807(15) 0.4974(6) 0.0434(10) Uani 1 1 d . . . H21 H 0.3086 0.3276 0.4711 0.052 Uiso 1 1 calc R . . C22 C 0.2828(4) 0.25667(15) 0.4506(6) 0.0456(11) Uani 1 1 d . . . H22 H 0.2035 0.2581 0.3928 0.055 Uiso 1 1 calc R . . C23 C 0.3372(4) 0.21286(14) 0.4887(5) 0.0385(9) Uani 1 1 d . . . H23 H 0.2947 0.1853 0.4529 0.046 Uiso 1 1 calc R . . N1 N 1.0297(3) -0.19496(11) 1.4755(4) 0.0336(8) Uani 1 1 d . . . H1N H 1.040(4) -0.2160(15) 1.401(5) 0.036(12) Uiso 1 1 d . . . N2 N 0.5912(3) 0.06810(11) 0.6915(4) 0.0336(7) Uani 1 1 d . . . H2N H 0.591(4) 0.0579(13) 0.568(5) 0.029(10) Uiso 1 1 d . . . N3 N 0.5023(3) 0.16414(11) 0.6315(4) 0.0327(7) Uani 1 1 d . . . O1 O 1.0500(3) -0.25307(9) 1.6682(4) 0.0457(7) Uani 1 1 d . . . O2 O 0.8464(3) -0.08960(9) 1.0691(4) 0.0447(7) Uani 1 1 d . . . Cl1 Cl 0.65964(10) 0.25065(4) 0.74299(13) 0.0422(3) Uani 1 1 d . . . Cl2 Cl 0.53839(12) 0.34797(4) 0.64032(14) 0.0511(3) Uani 1 1 d . . . Cl3 Cl 0.64248(12) 0.04173(4) 0.31700(14) 0.0488(3) Uani 1 1 d . . . 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 C1 0.029(2) 0.040(2) 0.036(2) 0.0031(18) -0.0035(16) -0.0050(17) C2 0.051(3) 0.047(2) 0.033(2) 0.0039(19) 0.0009(19) 0.001(2) C3 0.046(2) 0.039(2) 0.038(2) -0.0095(19) -0.0029(19) -0.0039(19) C4 0.037(2) 0.032(2) 0.036(2) -0.0015(17) 0.0037(17) -0.0041(17) C5 0.0282(19) 0.0237(18) 0.038(2) 0.0016(16) 0.0039(16) 0.0001(15) C6 0.032(2) 0.0266(19) 0.036(2) -0.0037(16) -0.0011(17) -0.0013(15) C7 0.034(2) 0.0257(19) 0.039(2) 0.0022(17) 0.0005(17) -0.0028(16) C8 0.050(3) 0.0225(19) 0.052(3) 0.0034(18) 0.002(2) 0.0023(18) C9 0.055(3) 0.026(2) 0.045(2) -0.0089(18) 0.004(2) -0.0061(18) C10 0.051(3) 0.028(2) 0.050(3) 0.0102(19) 0.004(2) 0.0017(18) C11 0.055(3) 0.040(2) 0.044(2) 0.011(2) 0.003(2) 0.010(2) C12 0.057(3) 0.048(3) 0.049(3) 0.016(2) 0.008(2) 0.018(2) C13 0.051(3) 0.033(2) 0.041(2) 0.0069(18) 0.003(2) 0.0040(19) C14 0.0257(19) 0.037(2) 0.046(2) 0.0007(18) 0.0025(17) 0.0005(17) C15 0.034(2) 0.033(2) 0.041(2) 0.0017(17) 0.0045(17) 0.0007(17) C16 0.029(2) 0.031(2) 0.056(3) -0.0012(19) -0.0005(19) -0.0022(17) C17 0.034(2) 0.032(2) 0.053(3) -0.0016(19) 0.0066(19) -0.0036(17) C18 0.030(2) 0.032(2) 0.035(2) 0.0023(17) 0.0046(16) 0.0004(16) C19 0.030(2) 0.036(2) 0.032(2) 0.0011(17) 0.0004(16) -0.0028(16) C20 0.042(2) 0.026(2) 0.037(2) 0.0007(17) 0.0035(18) -0.0016(17) C21 0.043(2) 0.033(2) 0.055(3) 0.009(2) 0.001(2) 0.0083(19) C22 0.032(2) 0.047(3) 0.058(3) 0.007(2) -0.008(2) 0.0009(19) C23 0.033(2) 0.032(2) 0.050(2) -0.0007(18) -0.0020(19) -0.0047(17) N1 0.0410(19) 0.0258(17) 0.0338(18) -0.0027(15) -0.0033(15) 0.0034(14) N2 0.0374(18) 0.0274(17) 0.0359(18) 0.0024(14) 0.0008(15) 0.0023(13) N3 0.0249(16) 0.0256(16) 0.048(2) 0.0019(14) 0.0027(14) -0.0001(13) O1 0.0544(18) 0.0316(15) 0.0505(18) 0.0091(13) -0.0154(15) -0.0039(13) O2 0.0603(19) 0.0297(14) 0.0436(16) 0.0077(13) -0.0129(14) 0.0036(13) Cl1 0.0378(5) 0.0394(5) 0.0491(6) -0.0010(5) -0.0102(5) -0.0031(4) Cl2 0.0725(8) 0.0292(5) 0.0513(6) 0.0018(5) -0.0113(6) -0.0087(5) Cl3 0.0675(7) 0.0343(5) 0.0446(6) -0.0049(5) 0.0006(5) -0.0015(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 C1 O1 1.241(5) . ? C1 N1 1.342(5) . ? C1 C2 1.493(6) . ? C2 C3 1.526(6) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.494(5) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C9 1.394(6) . ? C4 C5 1.396(5) . ? C5 C6 1.375(5) . ? C5 N1 1.416(5) . ? C6 C7 1.389(5) . ? C6 H6 0.9300 . ? C7 O2 1.371(5) . ? C7 C8 1.382(5) . ? C8 C9 1.379(6) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 O2 1.437(4) . ? C10 C11 1.499(6) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.524(6) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.503(6) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 N2 1.509(5) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 N2 1.499(5) . ? C14 C15 1.517(5) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 N3 1.471(5) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 N3 1.460(5) . ? C16 C17 1.511(6) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 N2 1.485(5) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C23 1.394(5) . ? C18 N3 1.407(5) . ? C18 C19 1.408(5) . ? C19 C20 1.385(5) . ? C19 Cl1 1.731(4) . ? C20 C21 1.377(6) . ? C20 Cl2 1.735(4) . ? C21 C22 1.374(6) . ? C21 H21 0.9300 . ? C22 C23 1.383(6) . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? N1 H1N 0.84(4) . ? N2 H2N 1.02(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 N1 120.4(4) . . ? O1 C1 C2 122.7(4) . . ? N1 C1 C2 116.9(4) . . ? C1 C2 C3 112.8(3) . . ? C1 C2 H2A 109.0 . . ? C3 C2 H2A 109.0 . . ? C1 C2 H2B 109.0 . . ? C3 C2 H2B 109.0 . . ? H2A C2 H2B 107.8 . . ? C4 C3 C2 109.7(3) . . ? C4 C3 H3A 109.7 . . ? C2 C3 H3A 109.7 . . ? C4 C3 H3B 109.7 . . ? C2 C3 H3B 109.7 . . ? H3A C3 H3B 108.2 . . ? C9 C4 C5 116.3(4) . . ? C9 C4 C3 125.2(4) . . ? C5 C4 C3 118.6(3) . . ? C6 C5 C4 122.1(3) . . ? C6 C5 N1 119.9(3) . . ? C4 C5 N1 118.0(3) . . ? C5 C6 C7 119.7(3) . . ? C5 C6 H6 120.2 . . ? C7 C6 H6 120.2 . . ? O2 C7 C8 124.7(3) . . ? O2 C7 C6 115.1(3) . . ? C8 C7 C6 120.1(4) . . ? C9 C8 C7 118.9(4) . . ? C9 C8 H8 120.6 . . ? C7 C8 H8 120.6 . . ? C8 C9 C4 123.0(4) . . ? C8 C9 H9 118.5 . . ? C4 C9 H9 118.5 . . ? O2 C10 C11 107.1(3) . . ? O2 C10 H10A 110.3 . . ? C11 C10 H10A 110.3 . . ? O2 C10 H10B 110.3 . . ? C11 C10 H10B 110.3 . . ? H10A C10 H10B 108.5 . . ? C10 C11 C12 113.2(4) . . ? C10 C11 H11A 108.9 . . ? C12 C11 H11A 108.9 . . ? C10 C11 H11B 108.9 . . ? C12 C11 H11B 108.9 . . ? H11A C11 H11B 107.8 . . ? C13 C12 C11 112.2(4) . . ? C13 C12 H12A 109.2 . . ? C11 C12 H12A 109.2 . . ? C13 C12 H12B 109.2 . . ? C11 C12 H12B 109.2 . . ? H12A C12 H12B 107.9 . . ? C12 C13 N2 112.6(3) . . ? C12 C13 H13A 109.1 . . ? N2 C13 H13A 109.1 . . ? C12 C13 H13B 109.1 . . ? N2 C13 H13B 109.1 . . ? H13A C13 H13B 107.8 . . ? N2 C14 C15 109.9(3) . . ? N2 C14 H14A 109.7 . . ? C15 C14 H14A 109.7 . . ? N2 C14 H14B 109.7 . . ? C15 C14 H14B 109.7 . . ? H14A C14 H14B 108.2 . . ? N3 C15 C14 109.3(3) . . ? N3 C15 H15A 109.8 . . ? C14 C15 H15A 109.8 . . ? N3 C15 H15B 109.8 . . ? C14 C15 H15B 109.8 . . ? H15A C15 H15B 108.3 . . ? N3 C16 C17 110.0(3) . . ? N3 C16 H16A 109.7 . . ? C17 C16 H16A 109.7 . . ? N3 C16 H16B 109.7 . . ? C17 C16 H16B 109.7 . . ? H16A C16 H16B 108.2 . . ? N2 C17 C16 111.9(3) . . ? N2 C17 H17A 109.2 . . ? C16 C17 H17A 109.2 . . ? N2 C17 H17B 109.2 . . ? C16 C17 H17B 109.2 . . ? H17A C17 H17B 107.9 . . ? C23 C18 N3 121.6(3) . . ? C23 C18 C19 116.7(3) . . ? N3 C18 C19 121.5(3) . . ? C20 C19 C18 120.6(3) . . ? C20 C19 Cl1 118.7(3) . . ? C18 C19 Cl1 120.7(3) . . ? C21 C20 C19 121.3(4) . . ? C21 C20 Cl2 117.8(3) . . ? C19 C20 Cl2 120.8(3) . . ? C22 C21 C20 118.8(4) . . ? C22 C21 H21 120.6 . . ? C20 C21 H21 120.6 . . ? C21 C22 C23 120.5(4) . . ? C21 C22 H22 119.7 . . ? C23 C22 H22 119.7 . . ? C22 C23 C18 121.9(4) . . ? C22 C23 H23 119.0 . . ? C18 C23 H23 119.0 . . ? C1 N1 C5 123.5(4) . . ? C1 N1 H1N 116(3) . . ? C5 N1 H1N 120(3) . . ? C17 N2 C14 109.9(3) . . ? C17 N2 C13 110.0(3) . . ? C14 N2 C13 113.5(3) . . ? C17 N2 H2N 106(2) . . ? C14 N2 H2N 105(2) . . ? C13 N2 H2N 112(2) . . ? C18 N3 C16 116.0(3) . . ? C18 N3 C15 120.0(3) . . ? C16 N3 C15 108.8(3) . . ? C7 O2 C10 118.6(3) . . ? 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 O1 C1 C2 C3 152.5(4) . . . . ? N1 C1 C2 C3 -29.1(5) . . . . ? C1 C2 C3 C4 49.5(5) . . . . ? C2 C3 C4 C9 143.8(4) . . . . ? C2 C3 C4 C5 -36.2(5) . . . . ? C9 C4 C5 C6 1.4(6) . . . . ? C3 C4 C5 C6 -178.6(4) . . . . ? C9 C4 C5 N1 -178.9(4) . . . . ? C3 C4 C5 N1 1.1(5) . . . . ? C4 C5 C6 C7 -2.6(6) . . . . ? N1 C5 C6 C7 177.8(3) . . . . ? C5 C6 C7 O2 -174.9(3) . . . . ? C5 C6 C7 C8 1.8(6) . . . . ? O2 C7 C8 C9 176.5(4) . . . . ? C6 C7 C8 C9 0.1(6) . . . . ? C7 C8 C9 C4 -1.3(7) . . . . ? C5 C4 C9 C8 0.6(6) . . . . ? C3 C4 C9 C8 -179.5(4) . . . . ? O2 C10 C11 C12 -171.0(4) . . . . ? C10 C11 C12 C13 -74.8(5) . . . . ? C11 C12 C13 N2 -166.0(4) . . . . ? N2 C14 C15 N3 60.5(4) . . . . ? N3 C16 C17 N2 -57.3(4) . . . . ? C23 C18 C19 C20 0.2(6) . . . . ? N3 C18 C19 C20 -175.3(4) . . . . ? C23 C18 C19 Cl1 178.7(3) . . . . ? N3 C18 C19 Cl1 3.2(5) . . . . ? C18 C19 C20 C21 1.2(6) . . . . ? Cl1 C19 C20 C21 -177.3(3) . . . . ? C18 C19 C20 Cl2 -179.5(3) . . . . ? Cl1 C19 C20 Cl2 2.0(5) . . . . ? C19 C20 C21 C22 -1.0(6) . . . . ? Cl2 C20 C21 C22 179.6(3) . . . . ? C20 C21 C22 C23 -0.5(7) . . . . ? C21 C22 C23 C18 1.9(7) . . . . ? N3 C18 C23 C22 173.8(4) . . . . ? C19 C18 C23 C22 -1.7(6) . . . . ? O1 C1 N1 C5 169.8(4) . . . . ? C2 C1 N1 C5 -8.7(5) . . . . ? C6 C5 N1 C1 -156.1(4) . . . . ? C4 C5 N1 C1 24.2(5) . . . . ? C16 C17 N2 C14 53.7(4) . . . . ? C16 C17 N2 C13 179.4(3) . . . . ? C15 C14 N2 C17 -55.0(4) . . . . ? C15 C14 N2 C13 -178.7(3) . . . . ? C12 C13 N2 C17 156.0(4) . . . . ? C12 C13 N2 C14 -80.4(4) . . . . ? C23 C18 N3 C16 -10.9(5) . . . . ? C19 C18 N3 C16 164.3(4) . . . . ? C23 C18 N3 C15 123.1(4) . . . . ? C19 C18 N3 C15 -61.6(5) . . . . ? C17 C16 N3 C18 -159.8(3) . . . . ? C17 C16 N3 C15 61.3(4) . . . . ? C14 C15 N3 C18 159.5(3) . . . . ? C14 C15 N3 C16 -63.5(4) . . . . ? C8 C7 O2 C10 12.1(6) . . . . ? C6 C7 O2 C10 -171.4(4) . . . . ? C11 C10 O2 C7 -178.2(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1N O1 0.84(4) 2.05(4) 2.849(5) 160(4) 4 N2 H2N Cl3 1.02(4) 2.11(4) 3.112(4) 165(3) . C13 H13B Cl3 0.97 2.73 3.558(5) 144.2 3_656 C15 H15A Cl1 0.97 2.48 3.146(4) 125.9 . C15 H15B Cl2 0.97 2.76 3.607(4) 145.9 4_565 C17 H17B Cl3 0.97 2.80 3.675(4) 149.9 3_656 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.591 _refine_diff_density_min -0.224 _refine_diff_density_rms 0.065 data_al86m _database_code_depnum_ccdc_archive 'CCDC 904820' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 'Aripiprazole benzoate monohydrate' ; _chemical_name_common "'Aripiprazole benzoate monohydrate'" _chemical_melting_point ? _chemical_formula_moiety 'C23 H28 Cl2 N3 O2, C7 H5 O2, H2 O' _chemical_formula_sum 'C30 H35 Cl2 N3 O5' _chemical_formula_weight 588.51 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 2(1)/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.9688(10) _cell_length_b 9.9536(6) _cell_length_c 20.9154(14) _cell_angle_alpha 90.00 _cell_angle_beta 108.0040(10) _cell_angle_gamma 90.00 _cell_volume 2963.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 6315 _cell_measurement_theta_min 2.50 _cell_measurement_theta_max 27.94 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.319 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1240 _exptl_absorpt_coefficient_mu 0.262 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9023 _exptl_absorpt_correction_T_max 0.9844 _exptl_absorpt_process_details 'Bruker AXS SADABS program' _exptl_special_details ; Sheldrick,G.M.,(2003),University of gottingen,Germany ; _diffrn_ambient_temperature 294(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 27834 _diffrn_reflns_av_R_equivalents 0.0232 _diffrn_reflns_av_sigmaI/netI 0.0163 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5228 _reflns_number_gt 4501 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0577P)^2^+0.7970P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5228 _refine_ls_number_parameters 377 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0433 _refine_ls_R_factor_gt 0.0372 _refine_ls_wR_factor_ref 0.1079 _refine_ls_wR_factor_gt 0.1015 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0.002 _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 C1 C -0.00236(12) -0.17703(19) 0.44614(9) 0.0518(4) Uani 1 1 d . . . C2 C -0.00162(15) -0.3072(2) 0.41031(12) 0.0691(5) Uani 1 1 d . . . H2A H -0.0243 -0.2912 0.3622 0.083 Uiso 1 1 calc R . . H2B H -0.0449 -0.3690 0.4212 0.083 Uiso 1 1 calc R . . C3 C 0.09378(16) -0.3725(2) 0.42760(14) 0.0768(6) Uani 1 1 d . . . H3A H 0.1096 -0.4112 0.4723 0.092 Uiso 1 1 calc R . . H3B H 0.0922 -0.4445 0.3960 0.092 Uiso 1 1 calc R . . C4 C 0.16786(14) -0.27200(18) 0.42528(10) 0.0562(4) Uani 1 1 d . . . C5 C 0.16001(11) -0.14299(16) 0.44873(8) 0.0445(4) Uani 1 1 d . . . C6 C 0.22694(11) -0.04625(17) 0.45186(8) 0.0453(4) Uani 1 1 d . . . H6 H 0.2213 0.0387 0.4687 0.054 Uiso 1 1 calc R . . C7 C 0.30274(11) -0.07617(17) 0.42969(9) 0.0482(4) Uani 1 1 d . . . C8 C 0.31055(13) -0.20235(19) 0.40405(10) 0.0578(5) Uani 1 1 d . . . H8 H 0.3604 -0.2223 0.3879 0.069 Uiso 1 1 calc R . . C9 C 0.24318(14) -0.29821(19) 0.40275(11) 0.0621(5) Uani 1 1 d . . . H9 H 0.2490 -0.3833 0.3861 0.074 Uiso 1 1 calc R . . C10 C 0.43835(12) 0.0085(2) 0.40496(10) 0.0557(4) Uani 1 1 d . . . H10A H 0.4130 -0.0205 0.3586 0.067 Uiso 1 1 calc R . . H10B H 0.4819 -0.0593 0.4297 0.067 Uiso 1 1 calc R . . C11 C 0.48752(12) 0.14101(19) 0.40859(10) 0.0564(4) Uani 1 1 d . . . H11A H 0.5113 0.1696 0.4551 0.068 Uiso 1 1 calc R . . H11B H 0.4429 0.2079 0.3841 0.068 Uiso 1 1 calc R . . C12 C 0.56859(12) 0.13223(19) 0.37927(10) 0.0546(4) Uani 1 1 d . . . H12A H 0.6142 0.0669 0.4042 0.066 Uiso 1 1 calc R . . H12B H 0.5454 0.1029 0.3328 0.066 Uiso 1 1 calc R . . C13 C 0.61478(13) 0.26766(19) 0.38291(10) 0.0559(5) Uani 1 1 d . . . H13A H 0.5664 0.3360 0.3692 0.067 Uiso 1 1 calc R . . H13B H 0.6512 0.2856 0.4292 0.067 Uiso 1 1 calc R . . C14 C 0.76038(11) 0.18795(17) 0.36184(9) 0.0475(4) Uani 1 1 d . . . H14A H 0.7393 0.0954 0.3591 0.057 Uiso 1 1 calc R . . H14B H 0.7955 0.2069 0.4083 0.057 Uiso 1 1 calc R . . C15 C 0.82294(11) 0.20704(16) 0.31834(9) 0.0463(4) Uani 1 1 d . . . H15A H 0.8768 0.1478 0.3335 0.056 Uiso 1 1 calc R . . H15B H 0.7887 0.1839 0.2722 0.056 Uiso 1 1 calc R . . C16 C 0.77343(12) 0.43380(18) 0.29516(10) 0.0548(4) Uani 1 1 d . . . H16A H 0.7399 0.4086 0.2492 0.066 Uiso 1 1 calc R . . H16B H 0.7936 0.5264 0.2953 0.066 Uiso 1 1 calc R . . C17 C 0.70941(13) 0.42022(18) 0.33808(11) 0.0581(5) Uani 1 1 d . . . H17A H 0.7423 0.4497 0.3835 0.070 Uiso 1 1 calc R . . H17B H 0.6550 0.4776 0.3203 0.070 Uiso 1 1 calc R . . C18 C 0.93054(11) 0.36683(16) 0.29510(8) 0.0439(4) Uani 1 1 d . . . C19 C 1.01960(11) 0.31616(16) 0.33029(8) 0.0432(4) Uani 1 1 d . . . C20 C 1.09392(11) 0.32845(17) 0.30453(9) 0.0482(4) Uani 1 1 d . . . C21 C 1.08414(13) 0.3995(2) 0.24640(9) 0.0582(5) Uani 1 1 d . . . H21 H 1.1347 0.4099 0.2299 0.070 Uiso 1 1 calc R . . C22 C 0.99827(14) 0.4548(2) 0.21311(10) 0.0635(5) Uani 1 1 d . . . H22 H 0.9914 0.5051 0.1744 0.076 Uiso 1 1 calc R . . C23 C 0.92202(13) 0.43695(19) 0.23610(9) 0.0551(4) Uani 1 1 d . . . H23 H 0.8640 0.4724 0.2117 0.066 Uiso 1 1 calc R . . N1 N 0.07992(10) -0.11043(16) 0.46763(7) 0.0489(3) Uani 1 1 d . . . H1N H 0.0796(12) -0.036(2) 0.4885(9) 0.054(5) Uiso 1 1 d . . . N2 N 0.67785(10) 0.27852(14) 0.33977(8) 0.0456(3) Uani 1 1 d . . . H2N H 0.6398(15) 0.252(2) 0.2944(11) 0.068(6) Uiso 1 1 d . . . N3 N 0.85501(9) 0.34713(13) 0.32152(7) 0.0452(3) Uani 1 1 d . . . O1 O -0.07365(8) -0.13099(14) 0.45500(7) 0.0632(3) Uani 1 1 d . . . O2 O 0.36426(8) 0.02713(13) 0.43382(7) 0.0599(3) Uani 1 1 d . . . Cl1 Cl 1.03856(3) 0.24540(5) 0.40888(2) 0.05481(14) Uani 1 1 d . . . Cl2 Cl 1.20170(3) 0.25576(6) 0.34561(3) 0.06769(16) Uani 1 1 d . . . C24 C 0.49946(14) 0.2540(2) 0.20148(11) 0.0622(5) Uani 1 1 d . . . C25 C 0.43183(13) 0.20921(19) 0.13539(10) 0.0583(5) Uani 1 1 d . . . C26 C 0.46002(14) 0.1242(2) 0.09328(10) 0.0662(5) Uani 1 1 d . . . H26 H 0.5217 0.0936 0.1057 0.079 Uiso 1 1 calc R . . C27 C 0.39686(17) 0.0840(3) 0.03242(12) 0.0829(7) Uani 1 1 d . . . H27 H 0.4162 0.0268 0.0041 0.099 Uiso 1 1 calc R . . C28 C 0.30582(18) 0.1289(3) 0.01436(14) 0.0884(8) Uani 1 1 d . . . H28 H 0.2635 0.1018 -0.0263 0.106 Uiso 1 1 calc R . . C29 C 0.27697(16) 0.2126(3) 0.05537(14) 0.0841(8) Uani 1 1 d . . . H29 H 0.2151 0.2427 0.0426 0.101 Uiso 1 1 calc R . . C30 C 0.33923(15) 0.2531(2) 0.11596(13) 0.0730(6) Uani 1 1 d . . . H30 H 0.3190 0.3101 0.1439 0.088 Uiso 1 1 calc R . . O3 O 0.58333(9) 0.21450(15) 0.21530(7) 0.0635(3) Uani 1 1 d . . . O4 O 0.47243(13) 0.3272(2) 0.23873(11) 0.1135(7) Uani 1 1 d . . . O1W O 0.67367(15) -0.0375(2) 0.23221(16) 0.1268(9) Uani 1 1 d D . . H1W H 0.630(2) 0.038(3) 0.2155(19) 0.167(15) Uiso 1 1 d D . . H2W H 0.625(3) -0.098(4) 0.2365(18) 0.144(13) Uiso 1 1 d . . . 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 C1 0.0466(9) 0.0629(11) 0.0499(9) 0.0011(8) 0.0205(7) -0.0122(8) C2 0.0628(12) 0.0654(12) 0.0849(14) -0.0135(11) 0.0310(11) -0.0248(10) C3 0.0769(14) 0.0505(11) 0.1124(18) -0.0107(11) 0.0429(13) -0.0148(10) C4 0.0572(11) 0.0465(10) 0.0697(12) -0.0032(8) 0.0266(9) -0.0055(8) C5 0.0429(8) 0.0482(9) 0.0458(8) -0.0001(7) 0.0188(7) -0.0022(7) C6 0.0440(8) 0.0458(9) 0.0509(9) -0.0050(7) 0.0216(7) -0.0024(7) C7 0.0434(9) 0.0496(9) 0.0558(9) -0.0003(7) 0.0218(7) -0.0024(7) C8 0.0530(10) 0.0558(10) 0.0738(12) -0.0039(9) 0.0329(9) 0.0060(8) C9 0.0658(12) 0.0436(10) 0.0843(13) -0.0094(9) 0.0341(10) 0.0007(9) C10 0.0472(9) 0.0635(11) 0.0665(11) -0.0037(9) 0.0322(8) -0.0031(8) C11 0.0475(10) 0.0614(11) 0.0686(11) -0.0032(9) 0.0301(9) -0.0035(8) C12 0.0481(9) 0.0576(10) 0.0663(11) -0.0029(9) 0.0297(8) -0.0043(8) C13 0.0517(10) 0.0586(11) 0.0673(12) -0.0118(9) 0.0328(9) -0.0062(8) C14 0.0410(8) 0.0453(9) 0.0593(10) 0.0009(7) 0.0200(7) -0.0036(7) C15 0.0394(8) 0.0420(8) 0.0604(10) -0.0018(7) 0.0197(7) -0.0036(7) C16 0.0475(9) 0.0428(9) 0.0775(12) 0.0063(8) 0.0243(9) -0.0006(7) C17 0.0524(10) 0.0416(9) 0.0875(13) -0.0048(9) 0.0322(10) -0.0010(8) C18 0.0406(8) 0.0435(8) 0.0489(9) -0.0023(7) 0.0155(7) -0.0092(7) C19 0.0418(8) 0.0456(9) 0.0424(8) -0.0008(7) 0.0132(7) -0.0096(7) C20 0.0401(8) 0.0516(9) 0.0537(9) -0.0048(8) 0.0155(7) -0.0086(7) C21 0.0535(10) 0.0675(12) 0.0612(11) 0.0030(9) 0.0288(9) -0.0120(9) C22 0.0671(12) 0.0712(13) 0.0563(11) 0.0156(9) 0.0249(9) -0.0097(10) C23 0.0489(9) 0.0590(10) 0.0561(10) 0.0102(8) 0.0141(8) -0.0031(8) N1 0.0443(8) 0.0523(9) 0.0565(8) -0.0079(7) 0.0249(6) -0.0088(6) N2 0.0392(7) 0.0444(7) 0.0573(9) -0.0042(6) 0.0211(6) -0.0043(6) N3 0.0384(7) 0.0421(7) 0.0572(8) 0.0017(6) 0.0180(6) -0.0042(6) O1 0.0444(7) 0.0804(9) 0.0710(8) -0.0085(7) 0.0271(6) -0.0125(6) O2 0.0497(7) 0.0573(7) 0.0867(9) -0.0119(6) 0.0415(6) -0.0088(6) Cl1 0.0478(2) 0.0703(3) 0.0458(2) 0.00804(19) 0.01368(18) -0.00392(19) Cl2 0.0397(2) 0.0882(4) 0.0753(3) 0.0050(3) 0.0181(2) -0.0017(2) C24 0.0518(11) 0.0580(11) 0.0747(13) 0.0080(10) 0.0167(10) 0.0036(9) C25 0.0448(9) 0.0535(10) 0.0730(12) 0.0176(9) 0.0130(9) -0.0054(8) C26 0.0504(10) 0.0761(14) 0.0709(13) 0.0090(10) 0.0169(9) -0.0108(9) C27 0.0788(15) 0.0948(17) 0.0716(14) 0.0038(12) 0.0181(12) -0.0170(13) C28 0.0737(15) 0.0951(19) 0.0780(15) 0.0232(14) -0.0035(12) -0.0114(14) C29 0.0526(12) 0.0747(15) 0.1048(19) 0.0348(14) -0.0051(12) 0.0019(11) C30 0.0563(12) 0.0600(12) 0.0962(17) 0.0213(11) 0.0142(11) 0.0046(9) O3 0.0442(7) 0.0777(9) 0.0665(8) 0.0023(7) 0.0139(6) -0.0038(6) O4 0.0841(12) 0.1303(17) 0.1126(14) -0.0352(13) 0.0105(11) 0.0378(12) O1W 0.0807(13) 0.0918(14) 0.221(3) -0.0212(16) 0.0658(16) -0.0029(12) _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 C1 O1 1.227(2) . ? C1 N1 1.348(2) . ? C1 C2 1.499(3) . ? C2 C3 1.508(3) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.505(3) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C9 1.375(3) . ? C4 C5 1.392(2) . ? C5 C6 1.376(2) . ? C5 N1 1.411(2) . ? C6 C7 1.384(2) . ? C6 H6 0.9300 . ? C7 O2 1.365(2) . ? C7 C8 1.385(3) . ? C8 C9 1.382(3) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 O2 1.4291(19) . ? C10 C11 1.500(3) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.522(2) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.506(2) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 N2 1.498(2) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 N2 1.483(2) . ? C14 C15 1.506(2) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 N3 1.470(2) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 N3 1.457(2) . ? C16 C17 1.508(2) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 N2 1.491(2) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C23 1.389(2) . ? C18 C19 1.402(2) . ? C18 N3 1.4173(19) . ? C19 C20 1.383(2) . ? C19 Cl1 1.7291(16) . ? C20 C21 1.375(3) . ? C20 Cl2 1.7341(18) . ? C21 C22 1.373(3) . ? C21 H21 0.9300 . ? C22 C23 1.380(2) . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? N1 H1N 0.86(2) . ? N2 H2N 0.98(2) . ? C24 O4 1.224(3) . ? C24 O3 1.261(2) . ? C24 C25 1.506(3) . ? C25 C26 1.378(3) . ? C25 C30 1.389(3) . ? C26 C27 1.389(3) . ? C26 H26 0.9300 . ? C27 C28 1.372(4) . ? C27 H27 0.9300 . ? C28 C29 1.358(4) . ? C28 H28 0.9300 . ? C29 C30 1.381(4) . ? C29 H29 0.9300 . ? C30 H30 0.9300 . ? O1W H1W 0.979(19) . ? O1W H2W 0.97(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 N1 120.92(17) . . ? O1 C1 C2 122.66(16) . . ? N1 C1 C2 116.41(16) . . ? C1 C2 C3 113.92(17) . . ? C1 C2 H2A 108.8 . . ? C3 C2 H2A 108.8 . . ? C1 C2 H2B 108.8 . . ? C3 C2 H2B 108.8 . . ? H2A C2 H2B 107.7 . . ? C4 C3 C2 111.01(17) . . ? C4 C3 H3A 109.4 . . ? C2 C3 H3A 109.4 . . ? C4 C3 H3B 109.4 . . ? C2 C3 H3B 109.4 . . ? H3A C3 H3B 108.0 . . ? C9 C4 C5 117.59(16) . . ? C9 C4 C3 125.12(17) . . ? C5 C4 C3 117.28(17) . . ? C6 C5 C4 121.49(15) . . ? C6 C5 N1 119.66(15) . . ? C4 C5 N1 118.81(15) . . ? C5 C6 C7 119.57(15) . . ? C5 C6 H6 120.2 . . ? C7 C6 H6 120.2 . . ? O2 C7 C6 115.05(15) . . ? O2 C7 C8 124.87(15) . . ? C6 C7 C8 120.05(16) . . ? C9 C8 C7 119.04(16) . . ? C9 C8 H8 120.5 . . ? C7 C8 H8 120.5 . . ? C4 C9 C8 122.20(17) . . ? C4 C9 H9 118.9 . . ? C8 C9 H9 118.9 . . ? O2 C10 C11 107.30(14) . . ? O2 C10 H10A 110.3 . . ? C11 C10 H10A 110.3 . . ? O2 C10 H10B 110.3 . . ? C11 C10 H10B 110.3 . . ? H10A C10 H10B 108.5 . . ? C10 C11 C12 111.65(15) . . ? C10 C11 H11A 109.3 . . ? C12 C11 H11A 109.3 . . ? C10 C11 H11B 109.3 . . ? C12 C11 H11B 109.3 . . ? H11A C11 H11B 108.0 . . ? C13 C12 C11 109.81(15) . . ? C13 C12 H12A 109.7 . . ? C11 C12 H12A 109.7 . . ? C13 C12 H12B 109.7 . . ? C11 C12 H12B 109.7 . . ? H12A C12 H12B 108.2 . . ? N2 C13 C12 113.52(14) . . ? N2 C13 H13A 108.9 . . ? C12 C13 H13A 108.9 . . ? N2 C13 H13B 108.9 . . ? C12 C13 H13B 108.9 . . ? H13A C13 H13B 107.7 . . ? N2 C14 C15 110.43(14) . . ? N2 C14 H14A 109.6 . . ? C15 C14 H14A 109.6 . . ? N2 C14 H14B 109.6 . . ? C15 C14 H14B 109.6 . . ? H14A C14 H14B 108.1 . . ? N3 C15 C14 110.35(13) . . ? N3 C15 H15A 109.6 . . ? C14 C15 H15A 109.6 . . ? N3 C15 H15B 109.6 . . ? C14 C15 H15B 109.6 . . ? H15A C15 H15B 108.1 . . ? N3 C16 C17 109.52(15) . . ? N3 C16 H16A 109.8 . . ? C17 C16 H16A 109.8 . . ? N3 C16 H16B 109.8 . . ? C17 C16 H16B 109.8 . . ? H16A C16 H16B 108.2 . . ? N2 C17 C16 111.29(14) . . ? N2 C17 H17A 109.4 . . ? C16 C17 H17A 109.4 . . ? N2 C17 H17B 109.4 . . ? C16 C17 H17B 109.4 . . ? H17A C17 H17B 108.0 . . ? C23 C18 C19 117.29(15) . . ? C23 C18 N3 123.41(15) . . ? C19 C18 N3 119.28(14) . . ? C20 C19 C18 120.81(15) . . ? C20 C19 Cl1 119.40(13) . . ? C18 C19 Cl1 119.70(12) . . ? C21 C20 C19 120.75(16) . . ? C21 C20 Cl2 118.77(13) . . ? C19 C20 Cl2 120.47(13) . . ? C22 C21 C20 118.79(16) . . ? C22 C21 H21 120.6 . . ? C20 C21 H21 120.6 . . ? C21 C22 C23 121.13(17) . . ? C21 C22 H22 119.4 . . ? C23 C22 H22 119.4 . . ? C22 C23 C18 121.02(17) . . ? C22 C23 H23 119.5 . . ? C18 C23 H23 119.5 . . ? C1 N1 C5 124.17(16) . . ? C1 N1 H1N 116.4(12) . . ? C5 N1 H1N 118.6(12) . . ? C14 N2 C17 110.04(13) . . ? C14 N2 C13 112.84(14) . . ? C17 N2 C13 110.23(13) . . ? C14 N2 H2N 108.5(12) . . ? C17 N2 H2N 108.8(12) . . ? C13 N2 H2N 106.2(13) . . ? C18 N3 C16 116.54(13) . . ? C18 N3 C15 113.73(13) . . ? C16 N3 C15 108.72(12) . . ? C7 O2 C10 118.17(13) . . ? O4 C24 O3 122.8(2) . . ? O4 C24 C25 119.99(19) . . ? O3 C24 C25 117.22(19) . . ? C26 C25 C30 118.8(2) . . ? C26 C25 C24 121.09(17) . . ? C30 C25 C24 120.2(2) . . ? C25 C26 C27 120.4(2) . . ? C25 C26 H26 119.8 . . ? C27 C26 H26 119.8 . . ? C28 C27 C26 119.7(3) . . ? C28 C27 H27 120.2 . . ? C26 C27 H27 120.2 . . ? C29 C28 C27 120.6(2) . . ? C29 C28 H28 119.7 . . ? C27 C28 H28 119.7 . . ? C28 C29 C30 120.2(2) . . ? C28 C29 H29 119.9 . . ? C30 C29 H29 119.9 . . ? C29 C30 C25 120.4(3) . . ? C29 C30 H30 119.8 . . ? C25 C30 H30 119.8 . . ? H1W O1W H2W 94(3) . . ? 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 O1 C1 C2 C3 -157.22(19) . . . . ? N1 C1 C2 C3 23.9(3) . . . . ? C1 C2 C3 C4 -46.8(3) . . . . ? C2 C3 C4 C9 -143.0(2) . . . . ? C2 C3 C4 C5 38.0(3) . . . . ? C9 C4 C5 C6 -2.5(3) . . . . ? C3 C4 C5 C6 176.60(18) . . . . ? C9 C4 C5 N1 175.50(17) . . . . ? C3 C4 C5 N1 -5.4(3) . . . . ? C4 C5 C6 C7 1.6(3) . . . . ? N1 C5 C6 C7 -176.33(15) . . . . ? C5 C6 C7 O2 178.93(15) . . . . ? C5 C6 C7 C8 0.5(3) . . . . ? O2 C7 C8 C9 -179.98(18) . . . . ? C6 C7 C8 C9 -1.8(3) . . . . ? C5 C4 C9 C8 1.2(3) . . . . ? C3 C4 C9 C8 -177.8(2) . . . . ? C7 C8 C9 C4 0.9(3) . . . . ? O2 C10 C11 C12 179.73(15) . . . . ? C10 C11 C12 C13 179.07(17) . . . . ? C11 C12 C13 N2 -164.89(16) . . . . ? N2 C14 C15 N3 58.80(18) . . . . ? N3 C16 C17 N2 -58.7(2) . . . . ? C23 C18 C19 C20 -4.1(2) . . . . ? N3 C18 C19 C20 177.17(15) . . . . ? C23 C18 C19 Cl1 172.39(13) . . . . ? N3 C18 C19 Cl1 -6.3(2) . . . . ? C18 C19 C20 C21 5.0(3) . . . . ? Cl1 C19 C20 C21 -171.56(14) . . . . ? C18 C19 C20 Cl2 -175.69(13) . . . . ? Cl1 C19 C20 Cl2 7.8(2) . . . . ? C19 C20 C21 C22 -2.0(3) . . . . ? Cl2 C20 C21 C22 178.71(15) . . . . ? C20 C21 C22 C23 -1.8(3) . . . . ? C21 C22 C23 C18 2.5(3) . . . . ? C19 C18 C23 C22 0.5(3) . . . . ? N3 C18 C23 C22 179.08(17) . . . . ? O1 C1 N1 C5 -167.63(16) . . . . ? C2 C1 N1 C5 11.3(3) . . . . ? C6 C5 N1 C1 156.38(16) . . . . ? C4 C5 N1 C1 -21.6(3) . . . . ? C15 C14 N2 C17 -54.28(18) . . . . ? C15 C14 N2 C13 -177.86(14) . . . . ? C16 C17 N2 C14 54.7(2) . . . . ? C16 C17 N2 C13 179.76(15) . . . . ? C12 C13 N2 C14 -64.9(2) . . . . ? C12 C13 N2 C17 171.59(16) . . . . ? C23 C18 N3 C16 -16.5(2) . . . . ? C19 C18 N3 C16 162.09(15) . . . . ? C23 C18 N3 C15 111.17(18) . . . . ? C19 C18 N3 C15 -70.23(19) . . . . ? C17 C16 N3 C18 -168.26(14) . . . . ? C17 C16 N3 C15 61.64(18) . . . . ? C14 C15 N3 C18 166.11(14) . . . . ? C14 C15 N3 C16 -62.27(18) . . . . ? C6 C7 O2 C10 -173.10(15) . . . . ? C8 C7 O2 C10 5.2(3) . . . . ? C11 C10 O2 C7 173.02(15) . . . . ? O4 C24 C25 C26 -178.5(2) . . . . ? O3 C24 C25 C26 2.6(3) . . . . ? O4 C24 C25 C30 1.3(3) . . . . ? O3 C24 C25 C30 -177.62(18) . . . . ? C30 C25 C26 C27 0.3(3) . . . . ? C24 C25 C26 C27 -179.90(19) . . . . ? C25 C26 C27 C28 -0.2(3) . . . . ? C26 C27 C28 C29 0.2(4) . . . . ? C27 C28 C29 C30 -0.2(4) . . . . ? C28 C29 C30 C25 0.3(3) . . . . ? C26 C25 C30 C29 -0.3(3) . . . . ? C24 C25 C30 C29 179.89(19) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1N O1 0.86(2) 2.06(2) 2.915(2) 174.3(17) 3_556 N2 H2N O3 0.98(2) 1.65(2) 2.628(2) 175(2) . N2 H2N O4 0.98(2) 2.53(2) 3.184(2) 124.3(15) . O1W H1W O3 0.979(19) 1.90(3) 2.819(3) 156(4) . O1W H2W O4 0.97(4) 1.85(4) 2.791(3) 163(3) 2_645 C15 H15A Cl1 0.97 2.63 3.2204(17) 119.3 . C29 H29 O1 0.93 2.48 3.365(3) 159.9 2 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.285 _refine_diff_density_min -0.249 _refine_diff_density_rms 0.035 data_an47m _database_code_depnum_ccdc_archive 'CCDC 904821' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 'Aripiprazole-2,4-dihydoxybenzoate' ; _chemical_name_common 'Aripiprazole-2,4-dihydoxybenzoate' _chemical_melting_point ? _chemical_formula_moiety 'C23 H28 Cl2 N3 O2, C7 H5 O4' _chemical_formula_sum 'C30 H33 Cl2 N3 O6' _chemical_formula_weight 602.49 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 2(1)/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 15.1552(8) _cell_length_b 9.5732(5) _cell_length_c 21.5283(11) _cell_angle_alpha 90.00 _cell_angle_beta 103.8870(10) _cell_angle_gamma 90.00 _cell_volume 3032.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 6915 _cell_measurement_theta_min 2.54 _cell_measurement_theta_max 28.02 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.320 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1264 _exptl_absorpt_coefficient_mu 0.261 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8851 _exptl_absorpt_correction_T_max 0.9694 _exptl_absorpt_process_details 'Bruker AXS SADABS program' _exptl_special_details ; Sheldrick,G.M.,(2003),University of gottingen,Germany ; _diffrn_ambient_temperature 294(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 28307 _diffrn_reflns_av_R_equivalents 0.0193 _diffrn_reflns_av_sigmaI/netI 0.0140 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5334 _reflns_number_gt 4618 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0976P)^2^+1.4966P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5334 _refine_ls_number_parameters 394 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0581 _refine_ls_R_factor_gt 0.0524 _refine_ls_wR_factor_ref 0.1682 _refine_ls_wR_factor_gt 0.1613 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.060 _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 C1 C 1.48743(16) 0.3029(3) 0.04009(11) 0.0529(6) Uani 1 1 d . B . C2 C 1.4777(2) 0.1643(3) 0.0690(2) 0.0892(11) Uani 1 1 d D . . H2A H 1.5151 0.0974 0.0532 0.107 Uiso 1 1 calc R A 1 H2B H 1.5013 0.1712 0.1150 0.107 Uiso 1 1 calc R A 1 C3 C 1.3854(4) 0.1096(5) 0.0566(8) 0.083(2) Uani 0.77(2) 1 d PD B 1 H3A H 1.3839 0.0301 0.0842 0.100 Uiso 0.77(2) 1 calc PR B 1 H3B H 1.3668 0.0780 0.0126 0.100 Uiso 0.77(2) 1 calc PR B 1 C3' C 1.4007(12) 0.127(2) 0.0936(15) 0.060(6) Uani 0.23(2) 1 d PD B 2 H3'1 H 1.4177 0.1322 0.1399 0.072 Uiso 0.23(2) 1 calc PR B 2 H3'2 H 1.3835 0.0313 0.0818 0.072 Uiso 0.23(2) 1 calc PR B 2 C4 C 1.3192(2) 0.2219(3) 0.06853(18) 0.0713(8) Uani 1 1 d D . . C5 C 1.33330(15) 0.3566(3) 0.04759(11) 0.0485(5) Uani 1 1 d . B . C6 C 1.27122(15) 0.4622(3) 0.04693(11) 0.0502(5) Uani 1 1 d . . . H6 H 1.2814 0.5508 0.0323 0.060 Uiso 1 1 calc R B . C7 C 1.19356(17) 0.4353(3) 0.06822(13) 0.0569(6) Uani 1 1 d . B . C8 C 1.1796(2) 0.3042(3) 0.09144(18) 0.0772(9) Uani 1 1 d . . . H8 H 1.1289 0.2866 0.1074 0.093 Uiso 1 1 calc R B . C9 C 1.2426(2) 0.1999(3) 0.0905(2) 0.0868(11) Uani 1 1 d . B . H9 H 1.2325 0.1114 0.1052 0.104 Uiso 1 1 calc R . . C10 C 1.05800(18) 0.5270(3) 0.09141(15) 0.0648(7) Uani 1 1 d . B . H10A H 1.0766 0.4978 0.1358 0.078 Uiso 1 1 calc R . . H10B H 1.0185 0.4558 0.0675 0.078 Uiso 1 1 calc R . . C11 C 1.00853(18) 0.6644(3) 0.08649(15) 0.0637(7) Uani 1 1 d . . . H11A H 0.9888 0.6918 0.0419 0.076 Uiso 1 1 calc R . . H11B H 1.0492 0.7360 0.1090 0.076 Uiso 1 1 calc R . . C12 C 0.92652(17) 0.6519(3) 0.11527(14) 0.0590(6) Uani 1 1 d . . . H12A H 0.9463 0.6211 0.1594 0.071 Uiso 1 1 calc R . . H12B H 0.8851 0.5822 0.0918 0.071 Uiso 1 1 calc R . . C13 C 0.87690(17) 0.7914(3) 0.11288(13) 0.0556(6) Uani 1 1 d . . . H13A H 0.9211 0.8664 0.1226 0.067 Uiso 1 1 calc R . . H13B H 0.8397 0.8065 0.0700 0.067 Uiso 1 1 calc R . . C14 C 0.74094(15) 0.6952(2) 0.14223(12) 0.0491(5) Uani 1 1 d . . . H14A H 0.7643 0.6008 0.1425 0.059 Uiso 1 1 calc R . . H14B H 0.7052 0.7154 0.0994 0.059 Uiso 1 1 calc R . . C15 C 0.68146(15) 0.7056(2) 0.18899(12) 0.0483(5) Uani 1 1 d . . . H15A H 0.6310 0.6408 0.1769 0.058 Uiso 1 1 calc R . . H15B H 0.7163 0.6807 0.2315 0.058 Uiso 1 1 calc R . . C16 C 0.72273(17) 0.9436(3) 0.21199(14) 0.0568(6) Uani 1 1 d . . . H16A H 0.7572 0.9156 0.2542 0.068 Uiso 1 1 calc R . . H16B H 0.7002 1.0376 0.2149 0.068 Uiso 1 1 calc R . . C17 C 0.78297(17) 0.9400(2) 0.16523(14) 0.0564(6) Uani 1 1 d . . . H17A H 0.7487 0.9715 0.1236 0.068 Uiso 1 1 calc R . . H17B H 0.8338 1.0032 0.1796 0.068 Uiso 1 1 calc R . . C18 C 0.57077(15) 0.8603(2) 0.21668(11) 0.0456(5) Uani 1 1 d . . . C19 C 0.48580(15) 0.8129(2) 0.18116(11) 0.0464(5) Uani 1 1 d . . . C20 C 0.40935(16) 0.8211(3) 0.20547(12) 0.0527(6) Uani 1 1 d . . . C21 C 0.41439(19) 0.8794(3) 0.26471(13) 0.0624(7) Uani 1 1 d . . . H21 H 0.3630 0.8848 0.2811 0.075 Uiso 1 1 calc R . . C22 C 0.4967(2) 0.9295(3) 0.29931(13) 0.0653(7) Uani 1 1 d . . . H22 H 0.5003 0.9709 0.3389 0.078 Uiso 1 1 calc R . . C23 C 0.57444(17) 0.9192(3) 0.27603(12) 0.0567(6) Uani 1 1 d . . . H23 H 0.6295 0.9523 0.3006 0.068 Uiso 1 1 calc R . . N1 N 1.41433(13) 0.3858(2) 0.02864(10) 0.0503(5) Uani 1 1 d . . . H1N H 1.4210(16) 0.458(3) 0.0113(12) 0.046(7) Uiso 1 1 d . . . N2 N 0.81803(13) 0.7952(2) 0.15948(10) 0.0467(4) Uani 1 1 d . . . H2N H 0.860(2) 0.775(3) 0.2003(15) 0.061(8) Uiso 1 1 d . . . N3 N 0.64676(12) 0.84799(19) 0.18955(9) 0.0467(4) Uani 1 1 d . . . O1 O 1.55926(11) 0.3423(2) 0.02846(8) 0.0604(5) Uani 1 1 d . . . O2 O 1.13606(13) 0.5459(2) 0.06571(11) 0.0729(6) Uani 1 1 d . . . Cl1 Cl 0.47578(4) 0.74997(7) 0.10443(3) 0.0578(2) Uani 1 1 d . . . Cl2 Cl 0.30480(5) 0.76216(9) 0.16110(4) 0.0775(3) Uani 1 1 d . . . C24 C 0.99759(19) 0.7992(3) 0.27673(15) 0.0664(7) Uani 1 1 d . . . C25 C 1.07408(17) 0.7705(3) 0.33181(14) 0.0579(6) Uani 1 1 d . . . C26 C 1.06302(17) 0.6922(3) 0.38356(14) 0.0593(6) Uani 1 1 d . . . H26 H 1.0062 0.6551 0.3832 0.071 Uiso 1 1 calc R . . C27 C 1.13560(19) 0.6677(3) 0.43629(14) 0.0642(7) Uani 1 1 d . . . H27 H 1.1269 0.6172 0.4712 0.077 Uiso 1 1 calc R . . C28 C 1.22038(17) 0.7197(3) 0.43568(13) 0.0556(6) Uani 1 1 d . . . C29 C 1.23330(17) 0.7969(3) 0.38420(14) 0.0586(6) Uani 1 1 d . . . H29 H 1.2908 0.8308 0.3841 0.070 Uiso 1 1 calc R . . C30 C 1.16133(18) 0.8234(3) 0.33332(13) 0.0586(6) Uani 1 1 d . . . O3 O 0.92018(12) 0.7431(2) 0.27530(11) 0.0714(6) Uani 1 1 d . . . O4 O 1.01091(16) 0.8779(3) 0.23337(13) 0.1016(8) Uani 1 1 d . . . O5 O 1.17633(16) 0.9033(3) 0.28469(12) 0.0902(7) Uani 1 1 d D . . H5O H 1.1187(16) 0.901(4) 0.2592(16) 0.108 Uiso 1 1 d D . . O6 O 1.29121(14) 0.6877(2) 0.48577(10) 0.0752(6) Uani 1 1 d D . . H6O H 1.3385(19) 0.739(3) 0.4818(18) 0.090 Uiso 1 1 d D . . 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 C1 0.0433(13) 0.0647(15) 0.0504(13) -0.0064(11) 0.0110(10) 0.0127(11) C2 0.072(2) 0.0684(19) 0.137(3) 0.022(2) 0.045(2) 0.0288(16) C3 0.067(3) 0.051(2) 0.133(7) -0.008(3) 0.025(4) 0.0078(19) C3' 0.060(8) 0.041(8) 0.083(12) 0.008(8) 0.026(8) 0.011(6) C4 0.0526(16) 0.0507(15) 0.113(2) 0.0046(15) 0.0247(16) 0.0049(12) C5 0.0386(11) 0.0519(13) 0.0554(13) -0.0022(10) 0.0120(9) 0.0034(10) C6 0.0447(12) 0.0505(13) 0.0589(13) 0.0058(10) 0.0193(10) 0.0046(10) C7 0.0475(13) 0.0552(14) 0.0738(16) 0.0054(12) 0.0259(12) 0.0068(11) C8 0.0582(16) 0.0642(17) 0.120(3) 0.0192(17) 0.0431(17) 0.0023(14) C9 0.0659(19) 0.0533(16) 0.151(3) 0.0233(19) 0.046(2) 0.0043(14) C10 0.0505(14) 0.0661(16) 0.0887(19) 0.0095(14) 0.0376(13) 0.0074(12) C11 0.0519(14) 0.0626(16) 0.0859(18) 0.0046(14) 0.0345(13) 0.0057(12) C12 0.0493(13) 0.0564(14) 0.0788(17) -0.0011(12) 0.0299(12) 0.0034(11) C13 0.0494(13) 0.0545(14) 0.0685(15) 0.0067(12) 0.0250(11) 0.0041(11) C14 0.0360(11) 0.0426(12) 0.0691(14) -0.0061(10) 0.0133(10) 0.0027(9) C15 0.0370(11) 0.0415(11) 0.0675(14) 0.0024(10) 0.0148(10) 0.0021(9) C16 0.0491(13) 0.0458(13) 0.0783(17) -0.0105(12) 0.0207(12) -0.0016(10) C17 0.0493(13) 0.0389(12) 0.0848(17) 0.0019(11) 0.0237(12) 0.0001(10) C18 0.0425(12) 0.0447(12) 0.0510(12) 0.0019(9) 0.0140(9) 0.0084(9) C19 0.0433(12) 0.0488(12) 0.0467(12) 0.0002(10) 0.0099(9) 0.0104(10) C20 0.0401(12) 0.0558(14) 0.0636(14) 0.0007(11) 0.0151(10) 0.0091(10) C21 0.0576(15) 0.0695(16) 0.0677(16) -0.0027(13) 0.0298(13) 0.0094(13) C22 0.0751(18) 0.0717(17) 0.0539(14) -0.0092(12) 0.0249(13) 0.0125(14) C23 0.0527(14) 0.0616(15) 0.0537(13) -0.0080(11) 0.0089(11) 0.0034(11) N1 0.0403(10) 0.0548(12) 0.0572(12) 0.0023(10) 0.0143(9) 0.0075(9) N2 0.0376(10) 0.0426(10) 0.0618(12) 0.0019(9) 0.0159(9) 0.0024(8) N3 0.0383(9) 0.0426(10) 0.0611(11) -0.0038(8) 0.0156(8) 0.0030(8) O1 0.0391(9) 0.0794(12) 0.0633(10) -0.0002(9) 0.0135(7) 0.0126(8) O2 0.0568(11) 0.0631(11) 0.1145(16) 0.0200(11) 0.0512(11) 0.0146(9) Cl1 0.0499(4) 0.0724(4) 0.0490(3) -0.0085(3) 0.0079(3) 0.0094(3) Cl2 0.0391(4) 0.0965(6) 0.0958(6) -0.0114(4) 0.0141(3) 0.0023(3) C24 0.0516(15) 0.0671(17) 0.0752(18) -0.0111(15) 0.0048(13) -0.0003(13) C25 0.0442(13) 0.0571(14) 0.0708(16) -0.0138(12) 0.0104(12) 0.0003(11) C26 0.0390(12) 0.0625(15) 0.0781(17) -0.0135(13) 0.0177(11) -0.0002(11) C27 0.0570(15) 0.0686(17) 0.0698(16) -0.0061(13) 0.0209(13) 0.0002(13) C28 0.0460(13) 0.0526(14) 0.0628(15) -0.0132(11) 0.0024(11) -0.0011(11) C29 0.0448(13) 0.0556(14) 0.0736(16) -0.0090(12) 0.0110(12) -0.0085(11) C30 0.0523(14) 0.0548(14) 0.0683(16) -0.0105(12) 0.0136(12) -0.0089(11) O3 0.0382(10) 0.0911(15) 0.0799(13) -0.0097(10) 0.0043(9) 0.0013(9) O4 0.0751(15) 0.113(2) 0.0991(17) 0.0259(15) -0.0139(13) -0.0290(14) O5 0.0712(14) 0.1101(18) 0.0831(15) 0.0087(13) 0.0065(11) -0.0268(13) O6 0.0583(12) 0.0815(14) 0.0768(13) 0.0040(11) -0.0018(10) -0.0088(10) _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 C1 O1 1.233(3) . ? C1 N1 1.337(3) . ? C1 C2 1.488(4) . ? C2 C3' 1.437(13) . ? C2 C3 1.456(6) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.534(6) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C3' C4 1.523(13) . ? C3' H3'1 0.9700 . ? C3' H3'2 0.9700 . ? C4 C9 1.370(4) . ? C4 C5 1.400(4) . ? C5 C6 1.378(3) . ? C5 N1 1.411(3) . ? C6 C7 1.386(3) . ? C6 H6 0.9300 . ? C7 O2 1.364(3) . ? C7 C8 1.385(4) . ? C8 C9 1.386(4) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 O2 1.433(3) . ? C10 C11 1.505(4) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.521(3) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.528(4) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 N2 1.494(3) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 N2 1.487(3) . ? C14 C15 1.507(3) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 N3 1.462(3) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 N3 1.459(3) . ? C16 C17 1.513(3) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 N2 1.500(3) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C23 1.386(3) . ? C18 C19 1.406(3) . ? C18 N3 1.416(3) . ? C19 C20 1.383(3) . ? C19 Cl1 1.731(2) . ? C20 C21 1.377(4) . ? C20 Cl2 1.736(3) . ? C21 C22 1.377(4) . ? C21 H21 0.9300 . ? C22 C23 1.390(4) . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? N1 H1N 0.80(3) . ? N2 H2N 0.97(3) . ? C24 O4 1.253(4) . ? C24 O3 1.284(4) . ? C24 C25 1.472(4) . ? C25 C26 1.386(4) . ? C25 C30 1.409(4) . ? C26 C27 1.398(4) . ? C26 H26 0.9300 . ? C27 C28 1.381(4) . ? C27 H27 0.9300 . ? C28 O6 1.361(3) . ? C28 C29 1.385(4) . ? C29 C30 1.371(4) . ? C29 H29 0.9300 . ? C30 O5 1.360(4) . ? O5 H5O 0.914(19) . ? O6 H6O 0.889(19) . ? 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 O1 C1 N1 120.9(3) . . ? O1 C1 C2 122.6(2) . . ? N1 C1 C2 116.4(2) . . ? C3' C2 C3 31.8(9) . . ? C3' C2 C1 123.1(6) . . ? C3 C2 C1 115.5(5) . . ? C3' C2 H2A 124.2 . . ? C3 C2 H2A 108.4 . . ? C1 C2 H2A 108.4 . . ? C3' C2 H2B 77.0 . . ? C3 C2 H2B 108.4 . . ? C1 C2 H2B 108.4 . . ? H2A C2 H2B 107.5 . . ? C2 C3 C4 110.8(4) . . ? C2 C3 H3A 109.5 . . ? C4 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? C4 C3 H3B 109.5 . . ? H3A C3 H3B 108.1 . . ? C2 C3' C4 112.5(9) . . ? C2 C3' H3'1 109.1 . . ? C4 C3' H3'1 109.1 . . ? C2 C3' H3'2 109.1 . . ? C4 C3' H3'2 109.1 . . ? H3'1 C3' H3'2 107.8 . . ? C9 C4 C5 117.4(3) . . ? C9 C4 C3' 117.9(6) . . ? C5 C4 C3' 119.3(7) . . ? C9 C4 C3 126.4(4) . . ? C5 C4 C3 115.8(4) . . ? C3' C4 C3 30.0(8) . . ? C6 C5 C4 121.5(2) . . ? C6 C5 N1 119.4(2) . . ? C4 C5 N1 119.1(2) . . ? C5 C6 C7 119.5(2) . . ? C5 C6 H6 120.3 . . ? C7 C6 H6 120.3 . . ? O2 C7 C8 124.5(2) . . ? O2 C7 C6 115.3(2) . . ? C8 C7 C6 120.2(2) . . ? C7 C8 C9 118.8(3) . . ? C7 C8 H8 120.6 . . ? C9 C8 H8 120.6 . . ? C4 C9 C8 122.6(3) . . ? C4 C9 H9 118.7 . . ? C8 C9 H9 118.7 . . ? O2 C10 C11 107.8(2) . . ? O2 C10 H10A 110.1 . . ? C11 C10 H10A 110.1 . . ? O2 C10 H10B 110.1 . . ? C11 C10 H10B 110.1 . . ? H10A C10 H10B 108.5 . . ? C10 C11 C12 110.1(2) . . ? C10 C11 H11A 109.6 . . ? C12 C11 H11A 109.6 . . ? C10 C11 H11B 109.6 . . ? C12 C11 H11B 109.6 . . ? H11A C11 H11B 108.1 . . ? C11 C12 C13 111.1(2) . . ? C11 C12 H12A 109.4 . . ? C13 C12 H12A 109.4 . . ? C11 C12 H12B 109.4 . . ? C13 C12 H12B 109.4 . . ? H12A C12 H12B 108.0 . . ? N2 C13 C12 111.5(2) . . ? N2 C13 H13A 109.3 . . ? C12 C13 H13A 109.3 . . ? N2 C13 H13B 109.3 . . ? C12 C13 H13B 109.3 . . ? H13A C13 H13B 108.0 . . ? N2 C14 C15 110.52(19) . . ? N2 C14 H14A 109.5 . . ? C15 C14 H14A 109.5 . . ? N2 C14 H14B 109.5 . . ? C15 C14 H14B 109.5 . . ? H14A C14 H14B 108.1 . . ? N3 C15 C14 109.95(19) . . ? N3 C15 H15A 109.7 . . ? C14 C15 H15A 109.7 . . ? N3 C15 H15B 109.7 . . ? C14 C15 H15B 109.7 . . ? H15A C15 H15B 108.2 . . ? N3 C16 C17 108.6(2) . . ? N3 C16 H16A 110.0 . . ? C17 C16 H16A 110.0 . . ? N3 C16 H16B 110.0 . . ? C17 C16 H16B 110.0 . . ? H16A C16 H16B 108.3 . . ? N2 C17 C16 111.00(19) . . ? N2 C17 H17A 109.4 . . ? C16 C17 H17A 109.4 . . ? N2 C17 H17B 109.4 . . ? C16 C17 H17B 109.4 . . ? H17A C17 H17B 108.0 . . ? C23 C18 C19 117.5(2) . . ? C23 C18 N3 123.9(2) . . ? C19 C18 N3 118.6(2) . . ? C20 C19 C18 121.1(2) . . ? C20 C19 Cl1 119.42(18) . . ? C18 C19 Cl1 119.38(17) . . ? C21 C20 C19 120.5(2) . . ? C21 C20 Cl2 118.79(19) . . ? C19 C20 Cl2 120.67(19) . . ? C22 C21 C20 118.9(2) . . ? C22 C21 H21 120.5 . . ? C20 C21 H21 120.5 . . ? C21 C22 C23 121.1(2) . . ? C21 C22 H22 119.4 . . ? C23 C22 H22 119.4 . . ? C18 C23 C22 120.7(2) . . ? C18 C23 H23 119.6 . . ? C22 C23 H23 119.6 . . ? C1 N1 C5 124.7(2) . . ? C1 N1 H1N 113.9(18) . . ? C5 N1 H1N 121.3(18) . . ? C14 N2 C13 112.1(2) . . ? C14 N2 C17 110.06(17) . . ? C13 N2 C17 110.98(18) . . ? C14 N2 H2N 113.5(17) . . ? C13 N2 H2N 103.8(17) . . ? C17 N2 H2N 106.1(17) . . ? C18 N3 C16 117.83(19) . . ? C18 N3 C15 114.24(18) . . ? C16 N3 C15 109.31(18) . . ? C7 O2 C10 117.8(2) . . ? O4 C24 O3 122.9(3) . . ? O4 C24 C25 118.4(3) . . ? O3 C24 C25 118.7(3) . . ? C26 C25 C30 118.0(3) . . ? C26 C25 C24 121.7(2) . . ? C30 C25 C24 120.3(3) . . ? C25 C26 C27 121.3(2) . . ? C25 C26 H26 119.3 . . ? C27 C26 H26 119.3 . . ? C28 C27 C26 119.0(3) . . ? C28 C27 H27 120.5 . . ? C26 C27 H27 120.5 . . ? O6 C28 C27 118.0(3) . . ? O6 C28 C29 121.2(2) . . ? C27 C28 C29 120.7(2) . . ? C30 C29 C28 120.0(2) . . ? C30 C29 H29 120.0 . . ? C28 C29 H29 120.0 . . ? O5 C30 C29 118.1(2) . . ? O5 C30 C25 120.9(3) . . ? C29 C30 C25 121.0(3) . . ? C30 O5 H5O 98(3) . . ? C28 O6 H6O 108(2) . . ? 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 O1 C1 C2 C3' 168.2(17) . . . . ? N1 C1 C2 C3' -10.1(17) . . . . ? O1 C1 C2 C3 -156.2(6) . . . . ? N1 C1 C2 C3 25.5(7) . . . . ? C3' C2 C3 C4 65.0(11) . . . . ? C1 C2 C3 C4 -47.2(11) . . . . ? C3 C2 C3' C4 -67.5(15) . . . . ? C1 C2 C3' C4 18(3) . . . . ? C2 C3' C4 C9 -177.7(14) . . . . ? C2 C3' C4 C5 -24(3) . . . . ? C2 C3' C4 C3 67.3(15) . . . . ? C2 C3 C4 C9 -147.7(6) . . . . ? C2 C3 C4 C5 40.4(12) . . . . ? C2 C3 C4 C3' -64.2(12) . . . . ? C9 C4 C5 C6 -2.2(5) . . . . ? C3' C4 C5 C6 -155.8(14) . . . . ? C3 C4 C5 C6 170.5(6) . . . . ? C9 C4 C5 N1 175.9(3) . . . . ? C3' C4 C5 N1 22.3(15) . . . . ? C3 C4 C5 N1 -11.5(7) . . . . ? C4 C5 C6 C7 0.9(4) . . . . ? N1 C5 C6 C7 -177.1(2) . . . . ? C5 C6 C7 O2 -179.9(2) . . . . ? C5 C6 C7 C8 1.6(4) . . . . ? O2 C7 C8 C9 179.0(3) . . . . ? C6 C7 C8 C9 -2.6(5) . . . . ? C5 C4 C9 C8 1.1(6) . . . . ? C3' C4 C9 C8 155.1(15) . . . . ? C3 C4 C9 C8 -170.7(8) . . . . ? C7 C8 C9 C4 1.3(6) . . . . ? O2 C10 C11 C12 -178.1(2) . . . . ? C10 C11 C12 C13 178.1(3) . . . . ? C11 C12 C13 N2 -160.4(2) . . . . ? N2 C14 C15 N3 58.5(2) . . . . ? N3 C16 C17 N2 -59.1(3) . . . . ? C23 C18 C19 C20 -1.9(3) . . . . ? N3 C18 C19 C20 179.4(2) . . . . ? C23 C18 C19 Cl1 175.41(18) . . . . ? N3 C18 C19 Cl1 -3.3(3) . . . . ? C18 C19 C20 C21 1.6(4) . . . . ? Cl1 C19 C20 C21 -175.7(2) . . . . ? C18 C19 C20 Cl2 -179.95(18) . . . . ? Cl1 C19 C20 Cl2 2.7(3) . . . . ? C19 C20 C21 C22 0.1(4) . . . . ? Cl2 C20 C21 C22 -178.4(2) . . . . ? C20 C21 C22 C23 -1.5(4) . . . . ? C19 C18 C23 C22 0.5(4) . . . . ? N3 C18 C23 C22 179.1(2) . . . . ? C21 C22 C23 C18 1.1(4) . . . . ? O1 C1 N1 C5 -171.8(2) . . . . ? C2 C1 N1 C5 6.5(4) . . . . ? C6 C5 N1 C1 164.8(2) . . . . ? C4 C5 N1 C1 -13.3(4) . . . . ? C15 C14 N2 C13 -178.05(19) . . . . ? C15 C14 N2 C17 -54.0(3) . . . . ? C12 C13 N2 C14 -66.6(3) . . . . ? C12 C13 N2 C17 169.8(2) . . . . ? C16 C17 N2 C14 54.8(3) . . . . ? C16 C17 N2 C13 179.5(2) . . . . ? C23 C18 N3 C16 -23.2(3) . . . . ? C19 C18 N3 C16 155.4(2) . . . . ? C23 C18 N3 C15 107.2(3) . . . . ? C19 C18 N3 C15 -74.3(3) . . . . ? C17 C16 N3 C18 -164.6(2) . . . . ? C17 C16 N3 C15 62.8(3) . . . . ? C14 C15 N3 C18 162.43(19) . . . . ? C14 C15 N3 C16 -63.1(3) . . . . ? C8 C7 O2 C10 2.9(4) . . . . ? C6 C7 O2 C10 -175.6(2) . . . . ? C11 C10 O2 C7 176.9(3) . . . . ? O4 C24 C25 C26 175.6(3) . . . . ? O3 C24 C25 C26 -4.1(4) . . . . ? O4 C24 C25 C30 -4.1(4) . . . . ? O3 C24 C25 C30 176.2(3) . . . . ? C30 C25 C26 C27 1.0(4) . . . . ? C24 C25 C26 C27 -178.7(3) . . . . ? C25 C26 C27 C28 -1.8(4) . . . . ? C26 C27 C28 O6 -176.2(2) . . . . ? C26 C27 C28 C29 1.0(4) . . . . ? O6 C28 C29 C30 177.6(2) . . . . ? C27 C28 C29 C30 0.5(4) . . . . ? C28 C29 C30 O5 177.9(3) . . . . ? C28 C29 C30 C25 -1.4(4) . . . . ? C26 C25 C30 O5 -178.7(3) . . . . ? C24 C25 C30 O5 1.0(4) . . . . ? C26 C25 C30 C29 0.6(4) . . . . ? C24 C25 C30 C29 -179.7(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1N O1 0.80(3) 2.14(3) 2.947(3) 176(2) 3_865 N2 H2N O3 0.97(3) 1.68(3) 2.648(3) 172(3) . O5 H5O O4 0.914(19) 1.61(2) 2.497(3) 163(4) . O6 H6O O1 0.889(19) 1.896(19) 2.785(3) 178(4) 2_855 C13 H13A O4 0.97 2.45 3.002(4) 115.9 . C14 H14A O5 0.97 2.48 3.302(4) 142.1 2_745 C15 H15A Cl1 0.97 2.70 3.238(2) 115.4 . C29 H29 O1 0.93 2.58 3.282(3) 132.4 2_855 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.748 _refine_diff_density_min -0.318 _refine_diff_density_rms 0.057 data_ao21m _database_code_depnum_ccdc_archive 'CCDC 904822' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 'Aripiprazole-2,5-dihydroxybenzoate hemihydrate' ; _chemical_name_common "'Aripiprazole-2,5-dihydroxybenzoate hemihydrate'" _chemical_melting_point ? _chemical_formula_moiety '2(C23 H28 Cl2 N3 O2),2(C7 H5 O4),H2O' _chemical_formula_sum 'C60 H68 Cl4 N6 O13' _chemical_formula_weight 1223.00 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' 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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 2(1)/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 30.4165(19) _cell_length_b 9.7801(6) _cell_length_c 20.5636(13) _cell_angle_alpha 90.00 _cell_angle_beta 105.3190(10) _cell_angle_gamma 90.00 _cell_volume 5899.8(6) _cell_formula_units_Z 4 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 6299 _cell_measurement_theta_min 2.32 _cell_measurement_theta_max 26.30 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.39 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.377 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2568 _exptl_absorpt_coefficient_mu 0.270 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8950 _exptl_absorpt_correction_T_max 0.9185 _exptl_absorpt_process_details 'Bruker AXS SADABS program' _exptl_special_details ; Sheldrick,G.M.,(2003),University of gottingen,Germany ; _diffrn_ambient_temperature 294(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 55196 _diffrn_reflns_av_R_equivalents 0.0302 _diffrn_reflns_av_sigmaI/netI 0.0230 _diffrn_reflns_limit_h_min -36 _diffrn_reflns_limit_h_max 36 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 25.00 _reflns_number_total 10383 _reflns_number_gt 8103 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0967P)^2^+1.8066P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 10383 _refine_ls_number_parameters 782 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0750 _refine_ls_R_factor_gt 0.0600 _refine_ls_wR_factor_ref 0.1651 _refine_ls_wR_factor_gt 0.1514 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.061 _refine_ls_shift/su_max 0.001 _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 C1 C 0.00207(8) 0.6914(3) 0.95552(12) 0.0450(6) Uani 1 1 d . . . C2 C 0.00506(10) 0.8281(3) 0.92344(17) 0.0619(8) Uani 1 1 d . . . H2A H -0.0070 0.8189 0.8750 0.074 Uiso 1 1 calc R . . H2B H -0.0143 0.8921 0.9390 0.074 Uiso 1 1 calc R . . C3 C 0.05195(11) 0.8875(3) 0.9375(2) 0.0724(9) Uani 1 1 d . . . H3A H 0.0602 0.9264 0.9825 0.087 Uiso 1 1 calc R . . H3B H 0.0521 0.9605 0.9057 0.087 Uiso 1 1 calc R . . C4 C 0.08660(9) 0.7809(3) 0.93217(14) 0.0467(6) Uani 1 1 d . . . C5 C 0.08102(7) 0.6491(2) 0.95477(11) 0.0356(5) Uani 1 1 d . . . C6 C 0.11308(7) 0.5473(2) 0.95650(11) 0.0371(5) Uani 1 1 d . . . H6 H 0.1092 0.4608 0.9730 0.045 Uiso 1 1 calc R . . C7 C 0.15094(8) 0.5758(2) 0.93342(12) 0.0384(5) Uani 1 1 d . . . C8 C 0.15656(9) 0.7041(3) 0.90823(13) 0.0455(6) Uani 1 1 d . . . H8 H 0.1815 0.7227 0.8916 0.055 Uiso 1 1 calc R . . C9 C 0.12421(9) 0.8045(3) 0.90824(14) 0.0499(6) Uani 1 1 d . . . H9 H 0.1281 0.8907 0.8915 0.060 Uiso 1 1 calc R . . C10 C 0.21850(8) 0.4868(3) 0.90886(13) 0.0448(6) Uani 1 1 d . . . H10A H 0.2387 0.5572 0.9333 0.054 Uiso 1 1 calc R . . H10B H 0.2080 0.5139 0.8619 0.054 Uiso 1 1 calc R . . C11 C 0.24314(8) 0.3520(3) 0.91480(13) 0.0438(6) Uani 1 1 d . . . H11A H 0.2222 0.2820 0.8915 0.053 Uiso 1 1 calc R . . H11B H 0.2535 0.3264 0.9620 0.053 Uiso 1 1 calc R . . C12 C 0.28379(8) 0.3590(2) 0.88500(13) 0.0410(5) Uani 1 1 d . . . H12A H 0.2739 0.3912 0.8388 0.049 Uiso 1 1 calc R . . H12B H 0.3059 0.4237 0.9105 0.049 Uiso 1 1 calc R . . C13 C 0.30598(8) 0.2195(3) 0.88651(13) 0.0415(6) Uani 1 1 d . . . H13A H 0.3237 0.2000 0.9322 0.050 Uiso 1 1 calc R . . H13B H 0.2824 0.1504 0.8738 0.050 Uiso 1 1 calc R . . C14 C 0.37695(8) 0.3039(2) 0.86015(12) 0.0388(5) Uani 1 1 d . . . H14A H 0.3938 0.2839 0.9062 0.047 Uiso 1 1 calc R . . H14B H 0.3666 0.3980 0.8584 0.047 Uiso 1 1 calc R . . C15 C 0.40783(8) 0.2866(2) 0.81429(13) 0.0398(5) Uani 1 1 d . . . H15A H 0.3916 0.3117 0.7686 0.048 Uiso 1 1 calc R . . H15B H 0.4340 0.3465 0.8288 0.048 Uiso 1 1 calc R . . C16 C 0.38364(8) 0.0556(3) 0.78957(13) 0.0450(6) Uani 1 1 d . . . H16A H 0.3934 -0.0385 0.7880 0.054 Uiso 1 1 calc R . . H16B H 0.3678 0.0836 0.7442 0.054 Uiso 1 1 calc R . . C17 C 0.35198(8) 0.0671(2) 0.83551(14) 0.0447(6) Uani 1 1 d . . . H17A H 0.3256 0.0090 0.8184 0.054 Uiso 1 1 calc R . . H17B H 0.3677 0.0352 0.8803 0.054 Uiso 1 1 calc R . . C18 C 0.46119(8) 0.1242(2) 0.78805(11) 0.0370(5) Uani 1 1 d . . . C19 C 0.50441(8) 0.1689(2) 0.82475(11) 0.0384(5) Uani 1 1 d . . . C20 C 0.54200(8) 0.1562(3) 0.79847(13) 0.0443(6) Uani 1 1 d . . . C21 C 0.53777(9) 0.0931(3) 0.73701(13) 0.0529(7) Uani 1 1 d . . . H21 H 0.5628 0.0848 0.7193 0.063 Uiso 1 1 calc R . . C22 C 0.49587(10) 0.0429(3) 0.70244(13) 0.0557(7) Uani 1 1 d . . . H22 H 0.4930 -0.0033 0.6620 0.067 Uiso 1 1 calc R . . C23 C 0.45787(9) 0.0598(3) 0.72683(13) 0.0488(6) Uani 1 1 d . . . H23 H 0.4297 0.0276 0.7018 0.059 Uiso 1 1 calc R . . N1 N 0.04105(7) 0.6178(2) 0.97453(11) 0.0414(5) Uani 1 1 d . . . H1N H 0.0390(9) 0.545(3) 0.9911(14) 0.049(9) Uiso 1 1 d . . . N2 N 0.33656(6) 0.21087(19) 0.83984(10) 0.0343(4) Uani 1 1 d . . . H2N H 0.3198(10) 0.234(3) 0.7972(15) 0.057(8) Uiso 1 1 d . . . N3 N 0.42327(6) 0.14342(19) 0.81566(10) 0.0376(4) Uani 1 1 d . . . O1 O -0.03394(6) 0.6459(2) 0.96306(9) 0.0535(5) Uani 1 1 d . . . O2 O 0.18053(6) 0.46873(18) 0.93703(10) 0.0522(5) Uani 1 1 d . . . Cl1 Cl 0.51211(2) 0.23556(7) 0.90504(3) 0.04888(18) Uani 1 1 d . . . Cl2 Cl 0.59536(2) 0.21452(9) 0.84320(4) 0.0675(2) Uani 1 1 d . . . C1' C 0.49427(8) 0.3146(3) 0.04737(12) 0.0456(6) Uani 1 1 d . . . C2' C 0.49033(9) 0.1802(3) 0.08063(16) 0.0590(7) Uani 1 1 d . . . H2C H 0.4994 0.1925 0.1292 0.071 Uiso 1 1 calc R . . H2D H 0.5113 0.1155 0.0692 0.071 Uiso 1 1 calc R . . C3' C 0.44256(10) 0.1208(3) 0.06013(18) 0.0631(8) Uani 1 1 d . . . H3C H 0.4357 0.0894 0.0138 0.076 Uiso 1 1 calc R . . H3D H 0.4407 0.0430 0.0886 0.076 Uiso 1 1 calc R . . C4' C 0.40826(9) 0.2282(3) 0.06703(14) 0.0458(6) Uani 1 1 d . . . C5' C 0.41548(7) 0.3610(2) 0.04730(11) 0.0365(5) Uani 1 1 d . . . C6' C 0.38460(7) 0.4652(2) 0.04797(11) 0.0385(5) Uani 1 1 d . . . H6' H 0.3894 0.5526 0.0335 0.046 Uiso 1 1 calc R . . C7' C 0.34634(8) 0.4371(2) 0.07055(12) 0.0414(6) Uani 1 1 d . . . C8' C 0.33952(9) 0.3076(3) 0.09330(14) 0.0497(6) Uani 1 1 d . . . H8' H 0.3147 0.2898 0.1103 0.060 Uiso 1 1 calc R . . C9' C 0.37051(9) 0.2044(3) 0.09028(15) 0.0529(7) Uani 1 1 d . . . H9' H 0.3655 0.1168 0.1044 0.063 Uiso 1 1 calc R . . C10' C 0.27928(8) 0.5254(3) 0.09607(14) 0.0490(6) Uani 1 1 d . . . H10C H 0.2894 0.4976 0.1430 0.059 Uiso 1 1 calc R . . H10D H 0.2596 0.4544 0.0710 0.059 Uiso 1 1 calc R . . C11' C 0.25391(8) 0.6582(3) 0.09005(14) 0.0489(6) Uani 1 1 d . . . H11C H 0.2441 0.6853 0.0430 0.059 Uiso 1 1 calc R . . H11D H 0.2740 0.7288 0.1146 0.059 Uiso 1 1 calc R . . C12' C 0.21239(8) 0.6448(3) 0.11814(13) 0.0451(6) Uani 1 1 d . . . H12C H 0.1921 0.5753 0.0931 0.054 Uiso 1 1 calc R . . H12D H 0.2221 0.6163 0.1649 0.054 Uiso 1 1 calc R . . C13' C 0.18724(8) 0.7796(3) 0.11312(13) 0.0437(6) Uani 1 1 d . . . H13C H 0.2093 0.8535 0.1234 0.052 Uiso 1 1 calc R . . H13D H 0.1689 0.7921 0.0672 0.052 Uiso 1 1 calc R . . C14' C 0.11801(8) 0.6894(2) 0.14193(12) 0.0390(5) Uani 1 1 d . . . H14C H 0.1297 0.5966 0.1451 0.047 Uiso 1 1 calc R . . H14D H 0.1006 0.7052 0.0957 0.047 Uiso 1 1 calc R . . C15' C 0.08740(8) 0.7058(2) 0.18812(13) 0.0389(5) Uani 1 1 d . . . H15C H 0.0620 0.6428 0.1748 0.047 Uiso 1 1 calc R . . H15D H 0.1042 0.6839 0.2340 0.047 Uiso 1 1 calc R . . C16' C 0.10878(8) 0.9402(2) 0.20964(14) 0.0449(6) Uani 1 1 d . . . H16C H 0.1254 0.9157 0.2552 0.054 Uiso 1 1 calc R . . H16D H 0.0978 1.0332 0.2101 0.054 Uiso 1 1 calc R . . C17' C 0.14002(8) 0.9301(2) 0.16295(14) 0.0457(6) Uani 1 1 d . . . H17C H 0.1236 0.9590 0.1180 0.055 Uiso 1 1 calc R . . H17D H 0.1658 0.9911 0.1788 0.055 Uiso 1 1 calc R . . C18' C 0.03288(8) 0.8622(2) 0.21440(11) 0.0365(5) Uani 1 1 d . . . C19' C -0.01031(8) 0.8120(2) 0.17914(11) 0.0381(5) Uani 1 1 d . . . C20' C -0.04697(8) 0.8190(3) 0.20722(12) 0.0427(6) Uani 1 1 d . . . C21' C -0.04259(9) 0.8813(3) 0.26890(13) 0.0506(7) Uani 1 1 d . . . H21' H -0.0672 0.8858 0.2877 0.061 Uiso 1 1 calc R . . C22' C -0.00108(10) 0.9367(3) 0.30200(13) 0.0534(7) Uani 1 1 d . . . H22' H 0.0019 0.9824 0.3426 0.064 Uiso 1 1 calc R . . C23' C 0.03633(9) 0.9256(3) 0.27604(12) 0.0463(6) Uani 1 1 d . . . H23' H 0.0642 0.9611 0.3002 0.056 Uiso 1 1 calc R . . N1' N 0.45573(7) 0.3904(2) 0.02787(10) 0.0412(5) Uani 1 1 d . . . H3N H 0.4578(8) 0.468(3) 0.0108(13) 0.042(7) Uiso 1 1 d . . . N2' N 0.15695(6) 0.78759(19) 0.16007(10) 0.0348(4) Uani 1 1 d . . . H4N H 0.1740(9) 0.770(3) 0.2015(13) 0.039(7) Uiso 1 1 d . . . N3' N 0.07016(6) 0.84671(19) 0.18539(10) 0.0388(5) Uani 1 1 d . . . O1' O 0.53029(6) 0.3563(2) 0.03850(9) 0.0552(5) Uani 1 1 d . . . O2' O 0.31773(6) 0.54559(19) 0.06929(10) 0.0565(5) Uani 1 1 d . . . Cl1' Cl -0.01818(2) 0.74747(7) 0.09841(3) 0.04650(18) Uani 1 1 d . . . Cl2' Cl -0.09962(2) 0.75122(8) 0.16478(4) 0.0603(2) Uani 1 1 d . . . C24 C 0.24403(10) 0.2472(3) 0.70555(13) 0.0481(6) Uani 1 1 d . . . C25 C 0.21360(8) 0.2871(3) 0.63722(13) 0.0440(6) Uani 1 1 d . . . C26 C 0.23122(9) 0.3624(3) 0.59240(12) 0.0450(6) Uani 1 1 d . . . H26 H 0.2615 0.3908 0.6056 0.054 Uiso 1 1 calc R . . C27 C 0.20473(10) 0.3959(3) 0.52871(13) 0.0510(6) Uani 1 1 d . . . C28 C 0.16024(10) 0.3562(3) 0.50958(15) 0.0613(8) Uani 1 1 d . . . H28 H 0.1425 0.3781 0.4666 0.074 Uiso 1 1 calc R . . C29 C 0.14100(9) 0.2840(3) 0.55276(15) 0.0555(7) Uani 1 1 d . . . H29 H 0.1104 0.2597 0.5392 0.067 Uiso 1 1 calc R . . C30 C 0.16756(10) 0.2475(3) 0.61691(14) 0.0531(7) Uani 1 1 d . . . O3 O 0.28547(6) 0.2760(2) 0.71811(9) 0.0548(5) Uani 1 1 d . . . O4 O 0.22521(8) 0.1871(3) 0.74539(11) 0.0838(7) Uani 1 1 d . . . O5 O 0.14825(8) 0.1764(3) 0.65872(12) 0.0805(7) Uani 1 1 d D . . H1O H 0.1665(11) 0.141(4) 0.6974(13) 0.097 Uiso 1 1 d D . . O6 O 0.22523(8) 0.4709(2) 0.48682(10) 0.0726(6) Uani 1 1 d D . . H2O H 0.2088(10) 0.471(4) 0.4469(11) 0.087 Uiso 1 1 d D . . C24' C 0.24708(9) 0.7840(3) 0.28919(13) 0.0455(6) Uani 1 1 d . . . C25' C 0.28733(8) 0.7567(3) 0.34772(13) 0.0465(6) Uani 1 1 d . . . C26' C 0.28224(9) 0.6802(3) 0.40252(13) 0.0505(7) Uani 1 1 d . . . H26' H 0.2536 0.6471 0.4027 0.061 Uiso 1 1 calc R . . C27' C 0.31943(11) 0.6529(3) 0.45689(15) 0.0623(8) Uani 1 1 d . . . C28' C 0.36210(10) 0.7032(3) 0.45469(18) 0.0682(9) Uani 1 1 d . . . H28' H 0.3874 0.6857 0.4906 0.082 Uiso 1 1 calc R . . C29' C 0.36740(10) 0.7773(3) 0.4010(2) 0.0750(10) Uani 1 1 d . . . H29' H 0.3963 0.8081 0.4006 0.090 Uiso 1 1 calc R . . C30' C 0.33067(9) 0.8072(3) 0.34733(16) 0.0594(8) Uani 1 1 d . . . O3' O 0.20983(5) 0.72426(18) 0.28546(8) 0.0447(4) Uani 1 1 d . . . O4' O 0.25183(7) 0.8698(2) 0.24568(11) 0.0773(7) Uani 1 1 d . . . O5' O 0.31597(9) 0.5784(3) 0.51096(12) 0.0901(8) Uani 1 1 d D . . H3O H 0.2871(8) 0.548(4) 0.507(2) 0.108 Uiso 1 1 d D . . O6' O 0.33770(8) 0.8849(3) 0.29612(14) 0.0841(7) Uani 1 1 d D . . H4O H 0.3101(8) 0.893(4) 0.2699(16) 0.101 Uiso 1 1 d D . . O1W O 0.19069(8) 0.4787(2) 0.34314(11) 0.0686(6) Uani 1 1 d D . . H1W H 0.1967(11) 0.556(2) 0.3220(15) 0.082 Uiso 1 1 d D . . H2W H 0.1988(11) 0.419(3) 0.3145(14) 0.082 Uiso 1 1 d D . . 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 C1 0.0364(14) 0.0595(16) 0.0405(13) -0.0062(12) 0.0130(11) 0.0091(12) C2 0.0519(17) 0.0579(18) 0.077(2) 0.0051(15) 0.0191(15) 0.0202(14) C3 0.0629(19) 0.0479(17) 0.112(3) 0.0038(17) 0.0335(19) 0.0123(15) C4 0.0443(14) 0.0384(13) 0.0591(16) 0.0021(12) 0.0166(12) 0.0056(11) C5 0.0325(12) 0.0415(13) 0.0343(12) -0.0008(10) 0.0115(9) 0.0014(10) C6 0.0344(12) 0.0368(12) 0.0430(13) 0.0062(10) 0.0149(10) 0.0015(10) C7 0.0335(12) 0.0397(13) 0.0457(13) 0.0014(10) 0.0167(10) 0.0015(10) C8 0.0408(14) 0.0446(14) 0.0567(16) 0.0039(12) 0.0229(12) -0.0051(11) C9 0.0498(15) 0.0355(13) 0.0687(18) 0.0090(12) 0.0231(13) -0.0014(11) C10 0.0378(13) 0.0472(14) 0.0578(15) 0.0042(12) 0.0276(12) 0.0010(11) C11 0.0393(13) 0.0436(14) 0.0541(15) 0.0016(11) 0.0223(11) 0.0002(11) C12 0.0356(12) 0.0418(13) 0.0492(14) 0.0009(11) 0.0176(11) 0.0028(10) C13 0.0384(13) 0.0449(14) 0.0454(14) 0.0091(11) 0.0182(11) 0.0045(10) C14 0.0321(12) 0.0337(12) 0.0518(14) 0.0000(10) 0.0132(10) 0.0041(10) C15 0.0345(12) 0.0334(12) 0.0550(15) 0.0037(11) 0.0176(11) 0.0037(10) C16 0.0402(13) 0.0385(13) 0.0582(16) -0.0053(11) 0.0166(12) 0.0019(11) C17 0.0434(14) 0.0292(12) 0.0646(16) 0.0041(11) 0.0199(12) 0.0012(10) C18 0.0376(13) 0.0356(12) 0.0392(12) 0.0034(10) 0.0127(10) 0.0094(10) C19 0.0397(13) 0.0414(13) 0.0346(12) -0.0009(10) 0.0106(10) 0.0116(10) C20 0.0391(13) 0.0483(14) 0.0476(14) 0.0032(11) 0.0151(11) 0.0121(11) C21 0.0495(16) 0.0630(17) 0.0538(16) 0.0026(13) 0.0272(13) 0.0149(13) C22 0.0652(18) 0.0643(18) 0.0410(14) -0.0084(13) 0.0203(13) 0.0154(14) C23 0.0464(15) 0.0550(16) 0.0442(14) -0.0044(12) 0.0106(12) 0.0061(12) N1 0.0319(11) 0.0504(13) 0.0451(12) 0.0067(10) 0.0156(9) 0.0058(9) N2 0.0303(10) 0.0344(10) 0.0399(11) 0.0053(8) 0.0124(9) 0.0037(8) N3 0.0329(10) 0.0347(10) 0.0470(11) -0.0014(8) 0.0136(9) 0.0059(8) O1 0.0326(9) 0.0749(13) 0.0558(11) 0.0020(9) 0.0170(8) 0.0095(9) O2 0.0414(10) 0.0443(10) 0.0838(13) 0.0139(9) 0.0393(9) 0.0087(8) Cl1 0.0437(4) 0.0614(4) 0.0416(3) -0.0096(3) 0.0114(3) 0.0066(3) Cl2 0.0354(4) 0.0913(6) 0.0774(5) -0.0100(4) 0.0175(3) 0.0026(3) C1' 0.0362(14) 0.0593(16) 0.0404(13) -0.0036(12) 0.0087(11) 0.0102(12) C2' 0.0475(16) 0.0614(18) 0.0685(19) 0.0063(15) 0.0158(14) 0.0199(14) C3' 0.0594(18) 0.0454(16) 0.086(2) 0.0026(15) 0.0212(16) 0.0089(13) C4' 0.0405(14) 0.0406(14) 0.0562(16) 0.0005(12) 0.0127(12) 0.0014(11) C5' 0.0307(11) 0.0445(13) 0.0349(12) 0.0005(10) 0.0093(9) 0.0008(10) C6' 0.0331(12) 0.0392(13) 0.0454(13) 0.0063(10) 0.0145(10) 0.0006(10) C7' 0.0339(12) 0.0448(14) 0.0481(14) 0.0020(11) 0.0156(11) 0.0031(10) C8' 0.0393(14) 0.0508(15) 0.0644(17) 0.0071(13) 0.0233(12) -0.0065(12) C9' 0.0479(16) 0.0405(14) 0.0717(19) 0.0096(13) 0.0184(14) -0.0042(12) C10' 0.0381(13) 0.0572(16) 0.0587(16) 0.0036(13) 0.0249(12) 0.0017(12) C11' 0.0377(13) 0.0560(16) 0.0592(16) 0.0028(13) 0.0235(12) 0.0004(12) C12' 0.0401(14) 0.0497(15) 0.0497(15) -0.0001(12) 0.0191(11) 0.0033(11) C13' 0.0395(13) 0.0521(15) 0.0435(14) 0.0085(11) 0.0180(11) 0.0027(11) C14' 0.0318(12) 0.0355(12) 0.0494(14) -0.0026(10) 0.0104(10) 0.0034(10) C15' 0.0316(12) 0.0318(12) 0.0549(15) 0.0027(10) 0.0141(11) 0.0019(9) C16' 0.0398(13) 0.0334(12) 0.0619(16) -0.0041(11) 0.0140(12) 0.0008(10) C17' 0.0424(14) 0.0328(12) 0.0622(16) 0.0077(11) 0.0145(12) 0.0009(10) C18' 0.0351(12) 0.0342(12) 0.0400(13) 0.0017(10) 0.0095(10) 0.0070(9) C19' 0.0380(13) 0.0393(13) 0.0357(12) -0.0015(10) 0.0075(10) 0.0107(10) C20' 0.0319(12) 0.0474(14) 0.0473(14) 0.0039(11) 0.0080(11) 0.0117(10) C21' 0.0471(15) 0.0589(16) 0.0508(15) 0.0020(13) 0.0217(12) 0.0171(13) C22' 0.0623(18) 0.0583(17) 0.0407(14) -0.0089(12) 0.0154(13) 0.0139(14) C23' 0.0447(14) 0.0468(14) 0.0443(14) -0.0047(11) 0.0065(11) 0.0044(11) N1' 0.0325(11) 0.0495(13) 0.0446(12) 0.0068(10) 0.0155(9) 0.0060(9) N2' 0.0303(10) 0.0343(10) 0.0397(11) 0.0052(8) 0.0094(9) 0.0016(8) N3' 0.0333(10) 0.0345(10) 0.0495(12) -0.0033(9) 0.0123(9) 0.0038(8) O1' 0.0304(9) 0.0784(13) 0.0586(11) 0.0063(10) 0.0150(8) 0.0094(9) O2' 0.0428(10) 0.0522(11) 0.0874(14) 0.0136(10) 0.0400(10) 0.0077(8) Cl1' 0.0435(4) 0.0561(4) 0.0384(3) -0.0073(3) 0.0082(3) 0.0059(3) Cl2' 0.0315(3) 0.0786(5) 0.0683(5) -0.0003(4) 0.0089(3) 0.0073(3) C24 0.0538(17) 0.0471(15) 0.0434(14) -0.0034(12) 0.0130(12) 0.0013(12) C25 0.0400(14) 0.0434(14) 0.0466(14) -0.0112(11) 0.0081(11) 0.0081(11) C26 0.0444(14) 0.0444(14) 0.0437(14) -0.0040(11) 0.0072(11) 0.0132(11) C27 0.0615(17) 0.0421(14) 0.0483(15) -0.0047(12) 0.0124(13) 0.0077(13) C28 0.0650(19) 0.0570(18) 0.0493(16) -0.0119(14) -0.0072(14) 0.0082(15) C29 0.0407(15) 0.0563(17) 0.0610(18) -0.0207(14) -0.0018(13) -0.0028(12) C30 0.0501(16) 0.0484(15) 0.0593(17) -0.0142(13) 0.0120(14) -0.0025(12) O3 0.0421(11) 0.0780(13) 0.0421(10) 0.0069(9) 0.0072(8) 0.0139(9) O4 0.0894(17) 0.1016(18) 0.0576(13) 0.0201(12) 0.0147(12) -0.0272(14) O5 0.0730(16) 0.0920(17) 0.0779(16) -0.0021(13) 0.0227(13) -0.0266(14) O6 0.0902(17) 0.0755(14) 0.0466(11) 0.0099(11) 0.0081(11) 0.0008(12) C24' 0.0415(14) 0.0514(15) 0.0447(14) -0.0079(12) 0.0131(11) -0.0045(12) C25' 0.0329(13) 0.0506(15) 0.0538(16) -0.0190(12) 0.0077(11) 0.0033(11) C26' 0.0388(14) 0.0538(16) 0.0530(16) -0.0116(13) 0.0016(12) 0.0117(12) C27' 0.0638(19) 0.0510(17) 0.0601(19) -0.0146(14) -0.0045(15) 0.0146(14) C28' 0.0437(17) 0.0602(19) 0.080(2) -0.0285(17) -0.0191(15) 0.0105(14) C29' 0.0393(16) 0.071(2) 0.105(3) -0.037(2) 0.0023(17) -0.0058(15) C30' 0.0433(16) 0.0595(18) 0.073(2) -0.0290(16) 0.0117(14) -0.0055(13) O3' 0.0324(9) 0.0583(11) 0.0420(9) 0.0037(8) 0.0071(7) 0.0016(8) O4' 0.0736(15) 0.0910(17) 0.0627(13) 0.0111(12) 0.0096(11) -0.0316(13) O5' 0.0943(18) 0.0892(18) 0.0655(15) 0.0093(13) -0.0163(14) 0.0145(15) O6' 0.0595(14) 0.0982(18) 0.0994(19) -0.0177(15) 0.0295(13) -0.0314(14) O1W 0.0843(15) 0.0594(13) 0.0659(14) -0.0031(10) 0.0264(11) -0.0074(12) _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 C1 O1 1.229(3) . ? C1 N1 1.353(3) . ? C1 C2 1.505(4) . ? C2 C3 1.496(4) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.507(4) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C9 1.379(4) . ? C4 C5 1.396(3) . ? C5 C6 1.387(3) . ? C5 N1 1.414(3) . ? C6 C7 1.385(3) . ? C6 H6 0.9300 . ? C7 O2 1.370(3) . ? C7 C8 1.385(3) . ? C8 C9 1.390(4) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 O2 1.433(3) . ? C10 C11 1.505(3) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.520(3) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.519(3) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 N2 1.505(3) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 N2 1.497(3) . ? C14 C15 1.506(3) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 N3 1.475(3) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 N3 1.461(3) . ? C16 C17 1.521(3) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 N2 1.492(3) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C23 1.387(3) . ? C18 C19 1.402(3) . ? C18 N3 1.426(3) . ? C19 C20 1.393(3) . ? C19 Cl1 1.733(2) . ? C20 C21 1.382(4) . ? C20 Cl2 1.737(3) . ? C21 C22 1.376(4) . ? C21 H21 0.9300 . ? C22 C23 1.386(4) . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? N1 H1N 0.80(3) . ? N2 H2N 0.92(3) . ? C1' O1' 1.227(3) . ? C1' N1' 1.355(3) . ? C1' C2' 1.502(4) . ? C2' C3' 1.518(4) . ? C2' H2C 0.9700 . ? C2' H2D 0.9700 . ? C3' C4' 1.513(4) . ? C3' H3C 0.9700 . ? C3' H3D 0.9700 . ? C4' C9' 1.375(4) . ? C4' C5' 1.396(3) . ? C5' C6' 1.388(3) . ? C5' N1' 1.414(3) . ? C6' C7' 1.390(3) . ? C6' H6' 0.9300 . ? C7' O2' 1.369(3) . ? C7' C8' 1.384(4) . ? C8' C9' 1.394(4) . ? C8' H8' 0.9300 . ? C9' H9' 0.9300 . ? C10' O2' 1.432(3) . ? C10' C11' 1.500(4) . ? C10' H10C 0.9700 . ? C10' H10D 0.9700 . ? C11' C12' 1.527(3) . ? C11' H11C 0.9700 . ? C11' H11D 0.9700 . ? C12' C13' 1.514(3) . ? C12' H12C 0.9700 . ? C12' H12D 0.9700 . ? C13' N2' 1.502(3) . ? C13' H13C 0.9700 . ? C13' H13D 0.9700 . ? C14' N2' 1.494(3) . ? C14' C15' 1.504(3) . ? C14' H14C 0.9700 . ? C14' H14D 0.9700 . ? C15' N3' 1.470(3) . ? C15' H15C 0.9700 . ? C15' H15D 0.9700 . ? C16' N3' 1.468(3) . ? C16' C17' 1.522(3) . ? C16' H16C 0.9700 . ? C16' H16D 0.9700 . ? C17' N2' 1.492(3) . ? C17' H17C 0.9700 . ? C17' H17D 0.9700 . ? C18' C23' 1.390(3) . ? C18' C19' 1.410(3) . ? C18' N3' 1.422(3) . ? C19' C20' 1.386(3) . ? C19' Cl1' 1.733(2) . ? C20' C21' 1.381(4) . ? C20' Cl2' 1.740(3) . ? C21' C22' 1.377(4) . ? C21' H21' 0.9300 . ? C22' C23' 1.383(4) . ? C22' H22' 0.9300 . ? C23' H23' 0.9300 . ? N1' H3N 0.84(3) . ? N2' H4N 0.89(3) . ? C24 O3 1.250(3) . ? C24 O4 1.262(3) . ? C24 C25 1.515(4) . ? C25 C26 1.393(4) . ? C25 C30 1.406(4) . ? C26 C27 1.384(4) . ? C26 H26 0.9300 . ? C27 C28 1.362(4) . ? C27 O6 1.398(4) . ? C28 C29 1.380(4) . ? C28 H28 0.9300 . ? C29 C30 1.399(4) . ? C29 H29 0.9300 . ? C30 O5 1.355(4) . ? O5 H1O 0.910(18) . ? O6 H2O 0.842(18) . ? C24' O3' 1.259(3) . ? C24' O4' 1.262(3) . ? C24' C25' 1.497(4) . ? C25' C26' 1.395(4) . ? C25' C30' 1.410(4) . ? C26' C27' 1.390(4) . ? C26' H26' 0.9300 . ? C27' O5' 1.356(4) . ? C27' C28' 1.400(5) . ? C28' C29' 1.365(5) . ? C28' H28' 0.9300 . ? C29' C30' 1.378(5) . ? C29' H29' 0.9300 . ? C30' O6' 1.361(4) . ? O5' H3O 0.913(19) . ? O6' H4O 0.873(18) . ? O1W H1W 0.917(18) . ? O1W H2W 0.911(18) . ? 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 O1 C1 N1 120.9(3) . . ? O1 C1 C2 122.4(2) . . ? N1 C1 C2 116.7(2) . . ? C3 C2 C1 115.2(2) . . ? C3 C2 H2A 108.5 . . ? C1 C2 H2A 108.5 . . ? C3 C2 H2B 108.5 . . ? C1 C2 H2B 108.5 . . ? H2A C2 H2B 107.5 . . ? C2 C3 C4 111.5(3) . . ? C2 C3 H3A 109.3 . . ? C4 C3 H3A 109.3 . . ? C2 C3 H3B 109.3 . . ? C4 C3 H3B 109.3 . . ? H3A C3 H3B 108.0 . . ? C9 C4 C5 117.3(2) . . ? C9 C4 C3 124.9(2) . . ? C5 C4 C3 117.8(2) . . ? C6 C5 C4 121.7(2) . . ? C6 C5 N1 119.3(2) . . ? C4 C5 N1 119.0(2) . . ? C7 C6 C5 119.3(2) . . ? C7 C6 H6 120.4 . . ? C5 C6 H6 120.4 . . ? O2 C7 C8 124.6(2) . . ? O2 C7 C6 114.9(2) . . ? C8 C7 C6 120.4(2) . . ? C7 C8 C9 118.8(2) . . ? C7 C8 H8 120.6 . . ? C9 C8 H8 120.6 . . ? C4 C9 C8 122.4(2) . . ? C4 C9 H9 118.8 . . ? C8 C9 H9 118.8 . . ? O2 C10 C11 107.24(19) . . ? O2 C10 H10A 110.3 . . ? C11 C10 H10A 110.3 . . ? O2 C10 H10B 110.3 . . ? C11 C10 H10B 110.3 . . ? H10A C10 H10B 108.5 . . ? C10 C11 C12 111.6(2) . . ? C10 C11 H11A 109.3 . . ? C12 C11 H11A 109.3 . . ? C10 C11 H11B 109.3 . . ? C12 C11 H11B 109.3 . . ? H11A C11 H11B 108.0 . . ? C13 C12 C11 110.82(19) . . ? C13 C12 H12A 109.5 . . ? C11 C12 H12A 109.5 . . ? C13 C12 H12B 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 108.1 . . ? N2 C13 C12 112.55(19) . . ? N2 C13 H13A 109.1 . . ? C12 C13 H13A 109.1 . . ? N2 C13 H13B 109.1 . . ? C12 C13 H13B 109.1 . . ? H13A C13 H13B 107.8 . . ? N2 C14 C15 111.02(19) . . ? N2 C14 H14A 109.4 . . ? C15 C14 H14A 109.4 . . ? N2 C14 H14B 109.4 . . ? C15 C14 H14B 109.4 . . ? H14A C14 H14B 108.0 . . ? N3 C15 C14 110.05(18) . . ? N3 C15 H15A 109.7 . . ? C14 C15 H15A 109.7 . . ? N3 C15 H15B 109.7 . . ? C14 C15 H15B 109.7 . . ? H15A C15 H15B 108.2 . . ? N3 C16 C17 109.0(2) . . ? N3 C16 H16A 109.9 . . ? C17 C16 H16A 109.9 . . ? N3 C16 H16B 109.9 . . ? C17 C16 H16B 109.9 . . ? H16A C16 H16B 108.3 . . ? N2 C17 C16 111.55(19) . . ? N2 C17 H17A 109.3 . . ? C16 C17 H17A 109.3 . . ? N2 C17 H17B 109.3 . . ? C16 C17 H17B 109.3 . . ? H17A C17 H17B 108.0 . . ? C23 C18 C19 117.6(2) . . ? C23 C18 N3 123.2(2) . . ? C19 C18 N3 119.1(2) . . ? C20 C19 C18 120.8(2) . . ? C20 C19 Cl1 119.01(19) . . ? C18 C19 Cl1 120.11(17) . . ? C21 C20 C19 120.4(2) . . ? C21 C20 Cl2 118.65(19) . . ? C19 C20 Cl2 120.87(19) . . ? C22 C21 C20 118.8(2) . . ? C22 C21 H21 120.6 . . ? C20 C21 H21 120.6 . . ? C21 C22 C23 121.2(2) . . ? C21 C22 H22 119.4 . . ? C23 C22 H22 119.4 . . ? C22 C23 C18 121.0(2) . . ? C22 C23 H23 119.5 . . ? C18 C23 H23 119.5 . . ? C1 N1 C5 123.8(2) . . ? C1 N1 H1N 116(2) . . ? C5 N1 H1N 119(2) . . ? C17 N2 C14 109.98(17) . . ? C17 N2 C13 110.36(18) . . ? C14 N2 C13 112.83(18) . . ? C17 N2 H2N 106.4(18) . . ? C14 N2 H2N 108.8(18) . . ? C13 N2 H2N 108.2(19) . . ? C18 N3 C16 116.87(18) . . ? C18 N3 C15 113.83(18) . . ? C16 N3 C15 108.87(18) . . ? C7 O2 C10 118.16(18) . . ? O1' C1' N1' 120.7(3) . . ? O1' C1' C2' 122.7(2) . . ? N1' C1' C2' 116.6(2) . . ? C1' C2' C3' 113.2(2) . . ? C1' C2' H2C 108.9 . . ? C3' C2' H2C 108.9 . . ? C1' C2' H2D 108.9 . . ? C3' C2' H2D 108.9 . . ? H2C C2' H2D 107.7 . . ? C4' C3' C2' 110.0(2) . . ? C4' C3' H3C 109.7 . . ? C2' C3' H3C 109.7 . . ? C4' C3' H3D 109.7 . . ? C2' C3' H3D 109.7 . . ? H3C C3' H3D 108.2 . . ? C9' C4' C5' 117.9(2) . . ? C9' C4' C3' 125.1(2) . . ? C5' C4' C3' 117.0(2) . . ? C6' C5' C4' 121.4(2) . . ? C6' C5' N1' 119.5(2) . . ? C4' C5' N1' 119.1(2) . . ? C5' C6' C7' 119.1(2) . . ? C5' C6' H6' 120.4 . . ? C7' C6' H6' 120.4 . . ? O2' C7' C8' 124.4(2) . . ? O2' C7' C6' 115.1(2) . . ? C8' C7' C6' 120.5(2) . . ? C7' C8' C9' 118.9(2) . . ? C7' C8' H8' 120.5 . . ? C9' C8' H8' 120.5 . . ? C4' C9' C8' 122.0(2) . . ? C4' C9' H9' 119.0 . . ? C8' C9' H9' 119.0 . . ? O2' C10' C11' 107.7(2) . . ? O2' C10' H10C 110.2 . . ? C11' C10' H10C 110.2 . . ? O2' C10' H10D 110.2 . . ? C11' C10' H10D 110.2 . . ? H10C C10' H10D 108.5 . . ? C10' C11' C12' 110.7(2) . . ? C10' C11' H11C 109.5 . . ? C12' C11' H11C 109.5 . . ? C10' C11' H11D 109.5 . . ? C12' C11' H11D 109.5 . . ? H11C C11' H11D 108.1 . . ? C13' C12' C11' 110.7(2) . . ? C13' C12' H12C 109.5 . . ? C11' C12' H12C 109.5 . . ? C13' C12' H12D 109.5 . . ? C11' C12' H12D 109.5 . . ? H12C C12' H12D 108.1 . . ? N2' C13' C12' 112.70(19) . . ? N2' C13' H13C 109.1 . . ? C12' C13' H13C 109.1 . . ? N2' C13' H13D 109.1 . . ? C12' C13' H13D 109.1 . . ? H13C C13' H13D 107.8 . . ? N2' C14' C15' 110.86(19) . . ? N2' C14' H14C 109.5 . . ? C15' C14' H14C 109.5 . . ? N2' C14' H14D 109.5 . . ? C15' C14' H14D 109.5 . . ? H14C C14' H14D 108.1 . . ? N3' C15' C14' 110.47(19) . . ? N3' C15' H15C 109.6 . . ? C14' C15' H15C 109.6 . . ? N3' C15' H15D 109.6 . . ? C14' C15' H15D 109.6 . . ? H15C C15' H15D 108.1 . . ? N3' C16' C17' 108.8(2) . . ? N3' C16' H16C 109.9 . . ? C17' C16' H16C 109.9 . . ? N3' C16' H16D 109.9 . . ? C17' C16' H16D 109.9 . . ? H16C C16' H16D 108.3 . . ? N2' C17' C16' 111.43(19) . . ? N2' C17' H17C 109.3 . . ? C16' C17' H17C 109.3 . . ? N2' C17' H17D 109.3 . . ? C16' C17' H17D 109.3 . . ? H17C C17' H17D 108.0 . . ? C23' C18' C19' 117.4(2) . . ? C23' C18' N3' 123.6(2) . . ? C19' C18' N3' 119.0(2) . . ? C20' C19' C18' 120.7(2) . . ? C20' C19' Cl1' 119.63(19) . . ? C18' C19' Cl1' 119.58(18) . . ? C21' C20' C19' 120.8(2) . . ? C21' C20' Cl2' 118.76(19) . . ? C19' C20' Cl2' 120.49(19) . . ? C22' C21' C20' 118.7(2) . . ? C22' C21' H21' 120.6 . . ? C20' C21' H21' 120.6 . . ? C21' C22' C23' 121.2(2) . . ? C21' C22' H22' 119.4 . . ? C23' C22' H22' 119.4 . . ? C22' C23' C18' 121.0(2) . . ? C22' C23' H23' 119.5 . . ? C18' C23' H23' 119.5 . . ? C1' N1' C5' 123.5(2) . . ? C1' N1' H3N 117.3(17) . . ? C5' N1' H3N 117.8(17) . . ? C17' N2' C14' 110.55(18) . . ? C17' N2' C13' 110.53(18) . . ? C14' N2' C13' 112.75(19) . . ? C17' N2' H4N 105.0(16) . . ? C14' N2' H4N 109.9(16) . . ? C13' N2' H4N 107.8(17) . . ? C18' N3' C16' 116.52(18) . . ? C18' N3' C15' 113.55(18) . . ? C16' N3' C15' 109.00(18) . . ? C7' O2' C10' 117.75(19) . . ? O3 C24 O4 125.2(3) . . ? O3 C24 C25 118.0(2) . . ? O4 C24 C25 116.8(3) . . ? C26 C25 C30 118.4(2) . . ? C26 C25 C24 120.1(2) . . ? C30 C25 C24 121.4(3) . . ? C27 C26 C25 121.5(3) . . ? C27 C26 H26 119.3 . . ? C25 C26 H26 119.3 . . ? C28 C27 C26 119.4(3) . . ? C28 C27 O6 122.9(3) . . ? C26 C27 O6 117.7(3) . . ? C27 C28 C29 121.2(3) . . ? C27 C28 H28 119.4 . . ? C29 C28 H28 119.4 . . ? C28 C29 C30 120.0(3) . . ? C28 C29 H29 120.0 . . ? C30 C29 H29 120.0 . . ? O5 C30 C29 119.4(3) . . ? O5 C30 C25 121.2(3) . . ? C29 C30 C25 119.4(3) . . ? C30 O5 H1O 119(3) . . ? C27 O6 H2O 111(2) . . ? O3' C24' O4' 122.3(2) . . ? O3' C24' C25' 119.8(2) . . ? O4' C24' C25' 117.8(2) . . ? C26' C25' C30' 119.7(3) . . ? C26' C25' C24' 120.3(2) . . ? C30' C25' C24' 120.0(3) . . ? C27' C26' C25' 120.8(3) . . ? C27' C26' H26' 119.6 . . ? C25' C26' H26' 119.6 . . ? O5' C27' C26' 122.6(3) . . ? O5' C27' C28' 119.3(3) . . ? C26' C27' C28' 118.1(3) . . ? C29' C28' C27' 121.4(3) . . ? C29' C28' H28' 119.3 . . ? C27' C28' H28' 119.3 . . ? C28' C29' C30' 121.1(3) . . ? C28' C29' H29' 119.5 . . ? C30' C29' H29' 119.5 . . ? O6' C30' C29' 118.6(3) . . ? O6' C30' C25' 122.6(3) . . ? C29' C30' C25' 118.8(3) . . ? C27' O5' H3O 113(3) . . ? C30' O6' H4O 102(3) . . ? H1W O1W H2W 96(3) . . ? 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 O1 C1 C2 C3 161.3(3) . . . . ? N1 C1 C2 C3 -20.3(4) . . . . ? C1 C2 C3 C4 43.1(4) . . . . ? C2 C3 C4 C9 145.0(3) . . . . ? C2 C3 C4 C5 -36.9(4) . . . . ? C9 C4 C5 C6 3.2(4) . . . . ? C3 C4 C5 C6 -175.1(3) . . . . ? C9 C4 C5 N1 -174.9(2) . . . . ? C3 C4 C5 N1 6.8(4) . . . . ? C4 C5 C6 C7 -1.9(4) . . . . ? N1 C5 C6 C7 176.2(2) . . . . ? C5 C6 C7 O2 -179.8(2) . . . . ? C5 C6 C7 C8 -0.7(4) . . . . ? O2 C7 C8 C9 -179.2(2) . . . . ? C6 C7 C8 C9 1.7(4) . . . . ? C5 C4 C9 C8 -2.1(4) . . . . ? C3 C4 C9 C8 176.0(3) . . . . ? C7 C8 C9 C4 -0.3(4) . . . . ? O2 C10 C11 C12 178.9(2) . . . . ? C10 C11 C12 C13 -175.6(2) . . . . ? C11 C12 C13 N2 162.7(2) . . . . ? N2 C14 C15 N3 -58.3(3) . . . . ? N3 C16 C17 N2 59.0(3) . . . . ? C23 C18 C19 C20 3.8(4) . . . . ? N3 C18 C19 C20 -177.8(2) . . . . ? C23 C18 C19 Cl1 -173.94(19) . . . . ? N3 C18 C19 Cl1 4.4(3) . . . . ? C18 C19 C20 C21 -3.2(4) . . . . ? Cl1 C19 C20 C21 174.6(2) . . . . ? C18 C19 C20 Cl2 178.75(19) . . . . ? Cl1 C19 C20 Cl2 -3.5(3) . . . . ? C19 C20 C21 C22 -0.2(4) . . . . ? Cl2 C20 C21 C22 177.9(2) . . . . ? C20 C21 C22 C23 2.8(4) . . . . ? C21 C22 C23 C18 -2.1(4) . . . . ? C19 C18 C23 C22 -1.2(4) . . . . ? N3 C18 C23 C22 -179.5(2) . . . . ? O1 C1 N1 C5 165.9(2) . . . . ? C2 C1 N1 C5 -12.5(4) . . . . ? C6 C5 N1 C1 -158.2(2) . . . . ? C4 C5 N1 C1 20.0(4) . . . . ? C16 C17 N2 C14 -53.9(3) . . . . ? C16 C17 N2 C13 -179.0(2) . . . . ? C15 C14 N2 C17 53.4(2) . . . . ? C15 C14 N2 C13 177.03(18) . . . . ? C12 C13 N2 C17 -171.7(2) . . . . ? C12 C13 N2 C14 64.9(3) . . . . ? C23 C18 N3 C16 19.6(3) . . . . ? C19 C18 N3 C16 -158.7(2) . . . . ? C23 C18 N3 C15 -108.7(3) . . . . ? C19 C18 N3 C15 73.0(3) . . . . ? C17 C16 N3 C18 166.87(19) . . . . ? C17 C16 N3 C15 -62.5(2) . . . . ? C14 C15 N3 C18 -164.82(19) . . . . ? C14 C15 N3 C16 62.9(2) . . . . ? C8 C7 O2 C10 -4.3(4) . . . . ? C6 C7 O2 C10 174.8(2) . . . . ? C11 C10 O2 C7 -175.8(2) . . . . ? O1' C1' C2' C3' -154.8(3) . . . . ? N1' C1' C2' C3' 25.9(4) . . . . ? C1' C2' C3' C4' -49.6(4) . . . . ? C2' C3' C4' C9' -141.1(3) . . . . ? C2' C3' C4' C5' 39.8(4) . . . . ? C9' C4' C5' C6' -3.0(4) . . . . ? C3' C4' C5' C6' 176.2(2) . . . . ? C9' C4' C5' N1' 175.4(2) . . . . ? C3' C4' C5' N1' -5.4(4) . . . . ? C4' C5' C6' C7' 1.8(4) . . . . ? N1' C5' C6' C7' -176.6(2) . . . . ? C5' C6' C7' O2' -179.8(2) . . . . ? C5' C6' C7' C8' 1.2(4) . . . . ? O2' C7' C8' C9' 178.2(2) . . . . ? C6' C7' C8' C9' -2.9(4) . . . . ? C5' C4' C9' C8' 1.2(4) . . . . ? C3' C4' C9' C8' -177.9(3) . . . . ? C7' C8' C9' C4' 1.7(4) . . . . ? O2' C10' C11' C12' -179.6(2) . . . . ? C10' C11' C12' C13' 179.1(2) . . . . ? C11' C12' C13' N2' -160.1(2) . . . . ? N2' C14' C15' N3' 57.8(2) . . . . ? N3' C16' C17' N2' -58.6(3) . . . . ? C23' C18' C19' C20' -3.7(3) . . . . ? N3' C18' C19' C20' 176.8(2) . . . . ? C23' C18' C19' Cl1' 173.55(18) . . . . ? N3' C18' C19' Cl1' -5.9(3) . . . . ? C18' C19' C20' C21' 3.2(4) . . . . ? Cl1' C19' C20' C21' -174.1(2) . . . . ? C18' C19' C20' Cl2' -177.60(18) . . . . ? Cl1' C19' C20' Cl2' 5.1(3) . . . . ? C19' C20' C21' C22' 0.1(4) . . . . ? Cl2' C20' C21' C22' -179.1(2) . . . . ? C20' C21' C22' C23' -2.8(4) . . . . ? C21' C22' C23' C18' 2.2(4) . . . . ? C19' C18' C23' C22' 1.1(4) . . . . ? N3' C18' C23' C22' -179.5(2) . . . . ? O1' C1' N1' C5' -168.0(2) . . . . ? C2' C1' N1' C5' 11.2(4) . . . . ? C6' C5' N1' C1' 155.7(2) . . . . ? C4' C5' N1' C1' -22.8(4) . . . . ? C16' C17' N2' C14' 53.8(3) . . . . ? C16' C17' N2' C13' 179.3(2) . . . . ? C15' C14' N2' C17' -52.9(3) . . . . ? C15' C14' N2' C13' -177.22(18) . . . . ? C12' C13' N2' C17' 169.2(2) . . . . ? C12' C13' N2' C14' -66.5(3) . . . . ? C23' C18' N3' C16' -21.0(3) . . . . ? C19' C18' N3' C16' 158.5(2) . . . . ? C23' C18' N3' C15' 106.9(3) . . . . ? C19' C18' N3' C15' -73.6(3) . . . . ? C17' C16' N3' C18' -167.70(19) . . . . ? C17' C16' N3' C15' 62.2(2) . . . . ? C14' C15' N3' C18' 165.60(19) . . . . ? C14' C15' N3' C16' -62.7(2) . . . . ? C8' C7' O2' C10' 2.9(4) . . . . ? C6' C7' O2' C10' -176.0(2) . . . . ? C11' C10' O2' C7' 179.1(2) . . . . ? O3 C24 C25 C26 -4.6(4) . . . . ? O4 C24 C25 C26 175.3(2) . . . . ? O3 C24 C25 C30 174.2(2) . . . . ? O4 C24 C25 C30 -5.9(4) . . . . ? C30 C25 C26 C27 -1.3(4) . . . . ? C24 C25 C26 C27 177.5(2) . . . . ? C25 C26 C27 C28 0.9(4) . . . . ? C25 C26 C27 O6 -179.6(2) . . . . ? C26 C27 C28 C29 0.5(4) . . . . ? O6 C27 C28 C29 -179.0(3) . . . . ? C27 C28 C29 C30 -1.5(4) . . . . ? C28 C29 C30 O5 -179.8(3) . . . . ? C28 C29 C30 C25 1.1(4) . . . . ? C26 C25 C30 O5 -178.8(2) . . . . ? C24 C25 C30 O5 2.5(4) . . . . ? C26 C25 C30 C29 0.2(4) . . . . ? C24 C25 C30 C29 -178.5(2) . . . . ? O3' C24' C25' C26' -8.7(4) . . . . ? O4' C24' C25' C26' 169.8(2) . . . . ? O3' C24' C25' C30' 170.7(2) . . . . ? O4' C24' C25' C30' -10.8(4) . . . . ? C30' C25' C26' C27' -0.1(4) . . . . ? C24' C25' C26' C27' 179.3(2) . . . . ? C25' C26' C27' O5' -179.7(3) . . . . ? C25' C26' C27' C28' -0.6(4) . . . . ? O5' C27' C28' C29' 179.2(3) . . . . ? C26' C27' C28' C29' 0.1(4) . . . . ? C27' C28' C29' C30' 1.0(5) . . . . ? C28' C29' C30' O6' 178.0(3) . . . . ? C28' C29' C30' C25' -1.7(4) . . . . ? C26' C25' C30' O6' -178.5(3) . . . . ? C24' C25' C30' O6' 2.1(4) . . . . ? C26' C25' C30' C29' 1.2(4) . . . . ? C24' C25' C30' C29' -178.2(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1N O1 0.80(3) 2.11(3) 2.914(3) 179(3) 3_567 N2 H2N O3 0.92(3) 1.73(3) 2.652(3) 177(3) . N1' H3N O1' 0.84(3) 2.08(3) 2.913(3) 171(2) 3_665 N2' H4N O3' 0.89(3) 1.84(3) 2.726(3) 177(2) . O5 H1O O4 0.910(18) 1.85(3) 2.542(3) 131(3) . O6 H2O O1W 0.842(18) 2.06(2) 2.863(3) 160(3) . O5' H3O O6 0.913(19) 1.96(2) 2.871(4) 172(4) . O6' H4O O4' 0.873(18) 1.73(2) 2.547(3) 156(4) . O1W H1W O3' 0.917(18) 1.892(19) 2.807(3) 175(3) . O1W H2W O4 0.911(18) 2.083(19) 2.981(3) 169(3) 4_565 C8 H8 O3' 0.93 2.60 3.413(3) 146.2 4_576 C13' H13C O4' 0.97 2.51 3.039(3) 114.2 . C14 H14B O6' 0.97 2.52 3.405(3) 152.4 4_576 C15 H15B Cl1 0.97 2.70 3.266(3) 117.4 . C15' H15C Cl1' 0.97 2.73 3.279(2) 116.7 . C26' H26' O1W 0.93 2.58 3.366(4) 143.1 . C29 H29 O1 0.93 2.57 3.461(3) 161.3 2_546 C29' H29' O1' 0.93 2.30 3.128(3) 147.6 2_655 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.641 _refine_diff_density_min -0.241 _refine_diff_density_rms 0.077