# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_[Ga.1]_12srv162 _database_code_depnum_ccdc_archive 'CCDC 906036' #TrackingRef 'web_deposit_cif_file_0_DmitryYufit_1350321914.Ga_L1.cif' _audit_creation_date 2012-08-29 _audit_creation_method ; Olex2 1.2-beta (compiled 2012.08.15 svn.r2450, GUI svn.r4314) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C13 H20 Ga N3 O6, H O0.5' _chemical_formula_sum 'C13 H21 Ga N3 O6.50' _chemical_formula_weight 393.05 _chemical_absolute_configuration ad _chemical_melting_point ? _chemical_oxdiff_formula 'C13 H21 Ga1 N3 O7' 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' Ga Ga 0.2307 1.6083 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system orthorhombic _space_group_IT_number 43 _space_group_name_H-M_alt 'F d d 2' _space_group_name_Hall 'F 2 -2d' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, z' 3 '-x+1/4, y+1/4, z+1/4' 4 'x+1/4, -y+1/4, z+1/4' 5 'x, y+1/2, z+1/2' 6 '-x, -y+1/2, z+1/2' 7 '-x+1/4, y+3/4, z+3/4' 8 'x+1/4, -y+3/4, z+3/4' 9 'x+1/2, y, z+1/2' 10 '-x+1/2, -y, z+1/2' 11 '-x+3/4, y+1/4, z+3/4' 12 'x+3/4, -y+1/4, z+3/4' 13 'x+1/2, y+1/2, z' 14 '-x+1/2, -y+1/2, z' 15 '-x+3/4, y+3/4, z+1/4' 16 'x+3/4, -y+3/4, z+1/4' _cell_length_a 28.8536(7) _cell_length_b 27.2438(7) _cell_length_c 7.57981(19) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5958.3(2) _cell_formula_units_Z 16 _cell_measurement_reflns_used 6080 _cell_measurement_temperature 120 _cell_measurement_theta_max 32.3124 _cell_measurement_theta_min 2.8181 _exptl_absorpt_coefficient_mu 1.888 _exptl_absorpt_correction_T_max 0.889 _exptl_absorpt_correction_T_min 0.430 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_crystal_colour 'dull light colourless' _exptl_crystal_colour_lustre dull _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.753 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 3248 _exptl_crystal_size_max 0.5901 _exptl_crystal_size_mid 0.1481 _exptl_crystal_size_min 0.0631 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0417 _diffrn_reflns_av_unetI/netI 0.0360 _diffrn_reflns_limit_h_max 36 _diffrn_reflns_limit_h_min -40 _diffrn_reflns_limit_k_max 38 _diffrn_reflns_limit_k_min -38 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 18337 _diffrn_reflns_theta_full 29.99 _diffrn_reflns_theta_max 29.99 _diffrn_reflns_theta_min 2.82 _diffrn_ambient_temperature 120 _diffrn_detector CCD _diffrn_detector_area_resol_mean 16.1511 _diffrn_detector_type Sapphire3 _diffrn_measured_fraction_theta_full 0.9981 _diffrn_measured_fraction_theta_max 0.9886 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -67.00 14.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - -31.7042 77.0000 0.0000 81 #__ type_ start__ end____ width___ exp.time_ 2 omega -108.00 28.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - -31.7042 0.0000 -30.0000 136 #__ type_ start__ end____ width___ exp.time_ 3 omega -22.00 34.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - -31.7042 19.0000 0.0000 56 #__ type_ start__ end____ width___ exp.time_ 4 omega 6.00 75.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - 32.1729 -100.0000 75.0000 69 #__ type_ start__ end____ width___ exp.time_ 5 omega 56.00 99.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - 32.1729 179.0000 0.0000 43 #__ type_ start__ end____ width___ exp.time_ 6 omega 16.00 84.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - 32.1729 57.0000 150.0000 68 #__ type_ start__ end____ width___ exp.time_ 7 omega 56.00 118.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - 32.1729 179.0000 -60.0000 62 #__ type_ start__ end____ width___ exp.time_ 8 omega -109.00 -3.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - -31.7042 -38.0000 -150.0000 106 ; _diffrn_measurement_device '3-circle diffractometer' _diffrn_measurement_device_type 'Xcalibur, Sapphire3, Gemini ultra' _diffrn_measurement_method \w-scan _diffrn_orient_matrix_UB_11 0.0054176000 _diffrn_orient_matrix_UB_12 0.0227335000 _diffrn_orient_matrix_UB_13 0.0406596000 _diffrn_orient_matrix_UB_21 0.0021080000 _diffrn_orient_matrix_UB_22 0.0111042000 _diffrn_orient_matrix_UB_23 -0.0842638000 _diffrn_orient_matrix_UB_31 -0.0238917000 _diffrn_orient_matrix_UB_32 0.0061148000 _diffrn_orient_matrix_UB_33 0.0017894000 _diffrn_radiation_collimation monochromator _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_xray_symbol Mo _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_source_type 'sealed tube' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 4081 _reflns_number_total 4319 _reflns_odcompleteness_completeness 99.81 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 30.93 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; XS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.447 _refine_diff_density_min -0.252 _refine_diff_density_rms 0.071 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.004(8) _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 297 _refine_ls_number_reflns 4319 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0338 _refine_ls_R_factor_gt 0.0307 _refine_ls_restrained_S_all 1.056 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0370P)^2^+0.8000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0657 _refine_ls_wR_factor_ref 0.0674 _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. ; _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 Ga1 Ga 0.352631(7) 0.390775(8) 0.54980(3) 0.01231(6) Uani 1 1 d . . . O1 O 0.29869(5) 0.41132(6) 0.6833(2) 0.0173(3) Uani 1 1 d . . . O2 O 0.27791(6) 0.46518(7) 0.8905(2) 0.0250(4) Uani 1 1 d . . . O3 O 0.33207(5) 0.32859(6) 0.4660(2) 0.0174(3) Uani 1 1 d . . . O4 O 0.31701(6) 0.28374(7) 0.2275(3) 0.0244(4) Uani 1 1 d . . . O5 O 0.38090(6) 0.36995(6) 0.7685(2) 0.0184(3) Uani 1 1 d . . . O6 O 0.44713(6) 0.36134(7) 0.9161(2) 0.0235(4) Uani 1 1 d . . . N1 N 0.36098(5) 0.46884(6) 0.5524(3) 0.0141(3) Uani 1 1 d . . . N2 N 0.33946(6) 0.41326(7) 0.2842(3) 0.0141(3) Uani 1 1 d . . . N3 N 0.42167(6) 0.38860(7) 0.4578(2) 0.0137(4) Uani 1 1 d . . . C1 C 0.32635(8) 0.49171(9) 0.4297(3) 0.0168(4) Uani 1 1 d . . . C2 C 0.30550(7) 0.45389(8) 0.3044(4) 0.0161(4) Uani 1 1 d . . . C3 C 0.38477(8) 0.43215(9) 0.2135(3) 0.0154(4) Uani 1 1 d . . . C4 C 0.42223(7) 0.43632(9) 0.3593(3) 0.0147(4) Uani 1 1 d . . . C5 C 0.40924(8) 0.47740(9) 0.4902(3) 0.0169(4) Uani 1 1 d . . . C6 C 0.34865(8) 0.48099(9) 0.7357(3) 0.0174(4) Uani 1 1 d . . . C7 C 0.30457(8) 0.45099(9) 0.7780(3) 0.0182(4) Uani 1 1 d . . . C8 C 0.31980(8) 0.37072(9) 0.1883(3) 0.0168(4) Uani 1 1 d . . . C9 C 0.32335(7) 0.32370(8) 0.2990(4) 0.0166(4) Uani 1 1 d . . . C10 C 0.45235(8) 0.38604(9) 0.6162(3) 0.0169(4) Uani 1 1 d . . . C11 C 0.42603(7) 0.37094(8) 0.7809(3) 0.0156(4) Uani 1 1 d . . . C12 C 0.46860(8) 0.44710(10) 0.2724(4) 0.0226(5) Uani 1 1 d . . . C13 C 0.43277(8) 0.34547(9) 0.3442(3) 0.0176(5) Uani 1 1 d . . . H1A H 0.3451(10) 0.5180(12) 0.362(4) 0.021(8) Uiso 1 1 d . . . H1B H 0.3014(9) 0.5074(10) 0.499(3) 0.015(7) Uiso 1 1 d . . . H2A H 0.2765(9) 0.4426(9) 0.352(3) 0.009(6) Uiso 1 1 d . . . H2B H 0.2980(9) 0.4678(10) 0.196(4) 0.015(7) Uiso 1 1 d . . . H3A H 0.3942(9) 0.4115(11) 0.126(4) 0.018(7) Uiso 1 1 d . . . H3B H 0.3829(9) 0.4628(11) 0.160(4) 0.016(7) Uiso 1 1 d . . . H5A H 0.4137(8) 0.5113(9) 0.428(4) 0.006(6) Uiso 1 1 d . . . H5B H 0.4280(10) 0.4788(11) 0.580(5) 0.024(8) Uiso 1 1 d . . . H6A H 0.3402(10) 0.5175(12) 0.752(4) 0.023(8) Uiso 1 1 d . . . H6B H 0.3732(9) 0.4720(9) 0.811(4) 0.014(6) Uiso 1 1 d . . . H8A H 0.2883(10) 0.3756(10) 0.169(4) 0.014(7) Uiso 1 1 d . . . H8B H 0.3335(12) 0.3653(12) 0.087(5) 0.037(9) Uiso 1 1 d . . . H10A H 0.4752(10) 0.3626(10) 0.602(4) 0.023(8) Uiso 1 1 d . . . H10B H 0.4660(10) 0.4174(12) 0.641(4) 0.023(7) Uiso 1 1 d . . . H12A H 0.4773(10) 0.4221(11) 0.188(4) 0.024(8) Uiso 1 1 d . . . H12B H 0.4689(10) 0.4788(13) 0.210(5) 0.034(9) Uiso 1 1 d . . . H12C H 0.4930(11) 0.4508(13) 0.360(5) 0.035(9) Uiso 1 1 d . . . H13A H 0.4651(8) 0.3435(9) 0.312(4) 0.010(6) Uiso 1 1 d . . . H13B H 0.4266(11) 0.3168(13) 0.402(5) 0.035(9) Uiso 1 1 d . . . H13C H 0.4155(10) 0.3449(12) 0.245(4) 0.023(8) Uiso 1 1 d . . . O1W O 0.2500 0.2500 -0.0075(4) 0.0267(6) Uani 1 2 d S . . H1W H 0.2700(10) 0.2615(13) 0.071(5) 0.040(9) 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 Ga1 0.01041(9) 0.01529(10) 0.01123(10) 0.00302(9) 0.00103(9) -0.00042(8) O1 0.0123(7) 0.0225(8) 0.0170(8) 0.0011(7) 0.0026(6) -0.0016(6) O2 0.0221(8) 0.0337(10) 0.0191(9) -0.0019(7) 0.0044(7) 0.0055(7) O3 0.0178(7) 0.0172(8) 0.0172(8) 0.0034(6) 0.0004(6) -0.0041(6) O4 0.0271(9) 0.0194(8) 0.0266(9) -0.0020(7) -0.0013(7) -0.0041(7) O5 0.0155(7) 0.0251(9) 0.0146(9) 0.0058(6) 0.0021(6) 0.0012(6) O6 0.0206(8) 0.0364(11) 0.0135(8) 0.0031(7) -0.0030(6) 0.0060(7) N1 0.0121(8) 0.0169(8) 0.0132(7) 0.0025(8) -0.0006(8) 0.0011(6) N2 0.0120(7) 0.0172(8) 0.0132(8) 0.0006(7) -0.0019(7) 0.0008(6) N3 0.0121(8) 0.0183(9) 0.0108(8) 0.0038(7) 0.0008(6) -0.0002(7) C1 0.0183(11) 0.0153(10) 0.0167(10) 0.0038(8) -0.0042(8) 0.0034(8) C2 0.0139(9) 0.0188(10) 0.0156(9) 0.0008(10) -0.0007(9) 0.0032(8) C3 0.0143(9) 0.0195(11) 0.0125(10) 0.0047(9) 0.0022(8) 0.0011(8) C4 0.0106(9) 0.0180(11) 0.0156(10) 0.0053(8) 0.0007(7) -0.0012(8) C5 0.0142(9) 0.0169(11) 0.0195(10) 0.0022(9) -0.0009(8) -0.0035(8) C6 0.0188(10) 0.0202(12) 0.0133(9) -0.0013(9) -0.0009(8) 0.0026(8) C7 0.0140(9) 0.0256(11) 0.0151(11) 0.0030(9) -0.0002(8) 0.0042(8) C8 0.0165(11) 0.0204(11) 0.0136(10) -0.0001(8) -0.0022(8) -0.0007(8) C9 0.0112(8) 0.0202(10) 0.0185(9) -0.0005(10) 0.0011(9) -0.0031(7) C10 0.0127(10) 0.0241(12) 0.0140(9) 0.0037(9) 0.0005(8) 0.0038(8) C11 0.0174(9) 0.0167(10) 0.0128(10) 0.0009(9) 0.0021(8) 0.0029(7) C12 0.0138(10) 0.0294(13) 0.0247(14) 0.0084(11) 0.0044(9) -0.0023(9) C13 0.0193(11) 0.0186(11) 0.0148(11) 0.0021(8) 0.0020(8) 0.0025(9) O1W 0.0237(13) 0.0376(16) 0.0187(11) 0.000 0.000 -0.0013(11) _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 Ga1 O1 1.9390(16) . ? Ga1 O3 1.9042(17) . ? Ga1 O5 1.9328(16) . ? Ga1 N1 2.1405(18) . ? Ga1 N2 2.138(2) . ? Ga1 N3 2.1115(18) . ? O1 C7 1.308(3) . ? O2 C7 1.212(3) . ? O3 C9 1.297(3) . ? O4 C9 1.230(3) . ? O5 C11 1.306(3) . ? O6 C11 1.220(3) . ? N1 C1 1.501(3) . ? N1 C5 1.488(3) . ? N1 C6 1.472(3) . ? N2 C2 1.486(3) . ? N2 C3 1.504(3) . ? N2 C8 1.481(3) . ? N3 C4 1.499(3) . ? N3 C10 1.494(3) . ? N3 C13 1.491(3) . ? C1 C2 1.525(3) . ? C1 H1A 1.04(3) . ? C1 H1B 0.99(3) . ? C2 H2A 0.96(3) . ? C2 H2B 0.93(3) . ? C3 C4 1.550(3) . ? C3 H3A 0.91(3) . ? C3 H3B 0.93(3) . ? C4 C5 1.542(3) . ? C4 C12 1.520(3) . ? C5 H5A 1.05(3) . ? C5 H5B 0.87(3) . ? C6 C7 1.545(3) . ? C6 H6A 1.03(3) . ? C6 H6B 0.94(3) . ? C8 C9 1.535(3) . ? C8 H8A 0.93(3) . ? C8 H8B 0.88(4) . ? C10 C11 1.518(3) . ? C10 H10A 0.93(3) . ? C10 H10B 0.96(3) . ? C12 H12A 0.97(3) . ? C12 H12B 0.98(3) . ? C12 H12C 0.97(3) . ? C13 H13A 0.97(2) . ? C13 H13B 0.91(4) . ? C13 H13C 0.90(3) . ? O1W H1W 0.89(3) . ? 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 Ga1 N1 78.39(7) . . ? O1 Ga1 N2 105.42(7) . . ? O1 Ga1 N3 159.68(7) . . ? O3 Ga1 O1 100.42(7) . . ? O3 Ga1 O5 99.00(7) . . ? O3 Ga1 N1 157.24(8) . . ? O3 Ga1 N2 83.42(7) . . ? O3 Ga1 N3 99.14(7) . . ? O5 Ga1 O1 88.62(7) . . ? O5 Ga1 N1 103.67(8) . . ? O5 Ga1 N2 165.16(7) . . ? O5 Ga1 N3 82.93(7) . . ? N2 Ga1 N1 75.16(8) . . ? N3 Ga1 N1 85.68(7) . . ? N3 Ga1 N2 82.23(7) . . ? C7 O1 Ga1 114.87(14) . . ? C9 O3 Ga1 118.51(14) . . ? C11 O5 Ga1 118.45(14) . . ? C1 N1 Ga1 109.39(13) . . ? C5 N1 Ga1 104.96(13) . . ? C5 N1 C1 111.22(19) . . ? C6 N1 Ga1 101.81(14) . . ? C6 N1 C1 109.32(17) . . ? C6 N1 C5 119.30(18) . . ? C2 N2 Ga1 103.52(15) . . ? C2 N2 C3 110.80(17) . . ? C3 N2 Ga1 106.22(13) . . ? C8 N2 Ga1 107.83(14) . . ? C8 N2 C2 112.37(17) . . ? C8 N2 C3 115.18(18) . . ? C4 N3 Ga1 98.64(12) . . ? C10 N3 Ga1 107.15(13) . . ? C10 N3 C4 115.76(17) . . ? C13 N3 Ga1 114.54(14) . . ? C13 N3 C4 113.16(17) . . ? C13 N3 C10 107.47(17) . . ? N1 C1 C2 111.59(18) . . ? N1 C1 H1A 104.4(17) . . ? N1 C1 H1B 109.4(15) . . ? C2 C1 H1A 111.3(18) . . ? C2 C1 H1B 109.7(16) . . ? H1A C1 H1B 110(2) . . ? N2 C2 C1 107.89(18) . . ? N2 C2 H2A 111.9(15) . . ? N2 C2 H2B 111.5(17) . . ? C1 C2 H2A 108.9(15) . . ? C1 C2 H2B 111.5(18) . . ? H2A C2 H2B 105(2) . . ? N2 C3 C4 112.14(18) . . ? N2 C3 H3A 107.9(17) . . ? N2 C3 H3B 114.4(17) . . ? C4 C3 H3A 110.9(17) . . ? C4 C3 H3B 106.6(18) . . ? H3A C3 H3B 105(3) . . ? N3 C4 C3 106.50(18) . . ? N3 C4 C5 107.82(18) . . ? N3 C4 C12 113.12(19) . . ? C5 C4 C3 110.04(19) . . ? C12 C4 C3 108.62(19) . . ? C12 C4 C5 110.64(19) . . ? N1 C5 C4 108.50(18) . . ? N1 C5 H5A 113.3(14) . . ? N1 C5 H5B 110(2) . . ? C4 C5 H5A 108.7(14) . . ? C4 C5 H5B 113(2) . . ? H5A C5 H5B 104(2) . . ? N1 C6 C7 105.99(19) . . ? N1 C6 H6A 112.6(18) . . ? N1 C6 H6B 109.4(18) . . ? C7 C6 H6A 106.9(17) . . ? C7 C6 H6B 110.9(16) . . ? H6A C6 H6B 111(2) . . ? O1 C7 C6 115.47(19) . . ? O2 C7 O1 124.6(2) . . ? O2 C7 C6 120.0(2) . . ? N2 C8 C9 111.03(19) . . ? N2 C8 H8A 109.7(18) . . ? N2 C8 H8B 113(2) . . ? C9 C8 H8A 105.7(17) . . ? C9 C8 H8B 108(2) . . ? H8A C8 H8B 109(3) . . ? O3 C9 C8 117.44(19) . . ? O4 C9 O3 123.3(2) . . ? O4 C9 C8 119.2(2) . . ? N3 C10 C11 112.17(18) . . ? N3 C10 H10A 111(2) . . ? N3 C10 H10B 111.0(19) . . ? C11 C10 H10A 105(2) . . ? C11 C10 H10B 106.6(18) . . ? H10A C10 H10B 110(3) . . ? O5 C11 C10 116.5(2) . . ? O6 C11 O5 123.6(2) . . ? O6 C11 C10 119.93(19) . . ? C4 C12 H12A 112.4(17) . . ? C4 C12 H12B 112.6(18) . . ? C4 C12 H12C 111(2) . . ? H12A C12 H12B 107(3) . . ? H12A C12 H12C 110(3) . . ? H12B C12 H12C 103(3) . . ? N3 C13 H13A 113.5(16) . . ? N3 C13 H13B 111(2) . . ? N3 C13 H13C 112(2) . . ? H13A C13 H13B 105(2) . . ? H13A C13 H13C 109(3) . . ? H13B C13 H13C 106(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 O1W H1W O4 0.89(3) 1.90(3) 2.785(2) 175(3) . loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z 0 0 -1 0.2950 -0.0000 0.0006 -0.9990 -0.0406 0.0842 -0.0018 0 0 1 0.2950 0.0000 -0.0006 0.9990 0.0406 -0.0842 0.0018 -1 0 0 0.0856 -0.9988 0.0004 0.0000 -0.0054 -0.0021 0.0239 1 0 0 0.0626 0.9988 -0.0004 -0.0000 0.0054 0.0021 -0.0239 0 -1 0 0.0315 0.0003 -0.9990 0.0000 -0.0227 -0.0111 -0.0061 0 1 0 0.0315 -0.0003 0.9990 -0.0000 0.0227 0.0111 0.0061 -35 9 5 0.1723 -34.9615 9.0000 4.9957 0.2183 -0.3947 0.8993 37 -7 4 0.1255 36.9587 -7.0085 3.9955 0.2034 -0.3366 -0.9187 data_[Ga.L2]_12srv170 _database_code_depnum_ccdc_archive 'CCDC 906037' #TrackingRef 'Ga_L2.cif' _audit_creation_date 2012-08-31 _audit_creation_method ; Olex2 1.2-beta (compiled 2012.08.15 svn.r2450, GUI svn.r4314) ; _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C15 H24 Ga N3 O6, H2 O' _chemical_formula_sum 'C15 H26 Ga N3 O7' _chemical_formula_weight 430.11 _chemical_absolute_configuration ad _chemical_melting_point ? _chemical_oxdiff_formula 'C15 H26 Ga1 N3 O7' 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' Ga Ga 0.2307 1.6083 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_H-M_alt 'P 1 21 1' _space_group_name_Hall 'P 2yb' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z' _cell_length_a 7.58267(20) _cell_length_b 12.6657(3) _cell_length_c 9.2185(2) _cell_angle_alpha 90.00 _cell_angle_beta 100.735(3) _cell_angle_gamma 90.00 _cell_volume 869.85(4) _cell_formula_units_Z 2 _cell_measurement_reflns_used 4205 _cell_measurement_temperature 120 _cell_measurement_theta_max 32.6015 _cell_measurement_theta_min 2.7286 _exptl_absorpt_coefficient_mu 1.627 _exptl_absorpt_correction_T_max 0.916 _exptl_absorpt_correction_T_min 0.671 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.642 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 448 _exptl_crystal_size_max 0.275 _exptl_crystal_size_mid 0.1521 _exptl_crystal_size_min 0.0558 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0433 _diffrn_reflns_av_unetI/netI 0.0507 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 12473 _diffrn_reflns_theta_full 28.99 _diffrn_reflns_theta_max 28.99 _diffrn_reflns_theta_min 2.73 _diffrn_ambient_temperature 120 _diffrn_detector CCD _diffrn_detector_area_resol_mean 16.1511 _diffrn_detector_type Sapphire3 _diffrn_measured_fraction_theta_full 0.9907 _diffrn_measured_fraction_theta_max 0.9934 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -48.00 37.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - -26.3429 57.0000 -60.0000 85 #__ type_ start__ end____ width___ exp.time_ 2 omega -89.00 -13.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - -26.3429 -57.0000 60.0000 76 #__ type_ start__ end____ width___ exp.time_ 3 omega -99.00 17.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - -26.3429 -19.0000 120.0000 116 #__ type_ start__ end____ width___ exp.time_ 4 omega 14.00 68.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 26.9679 -100.0000 -180.0000 54 #__ type_ start__ end____ width___ exp.time_ 5 omega -3.00 69.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 26.9679 -100.0000 30.0000 72 #__ type_ start__ end____ width___ exp.time_ 6 omega 38.00 69.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 26.9679 -100.0000 -90.0000 31 #__ type_ start__ end____ width___ exp.time_ 7 omega 56.00 81.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 26.9679 179.0000 60.0000 25 #__ type_ start__ end____ width___ exp.time_ 8 omega -48.00 42.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - -26.3429 57.0000 90.0000 90 #__ type_ start__ end____ width___ exp.time_ 9 omega -95.00 -5.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - -26.3429 -57.0000 -60.0000 90 #__ type_ start__ end____ width___ exp.time_ 10 omega -45.00 -20.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 26.9679 -38.0000 150.0000 25 ; _diffrn_measurement_device '3-circle diffractometer' _diffrn_measurement_device_type 'Xcalibur, Sapphire3, Gemini ultra' _diffrn_measurement_method \w-scan _diffrn_orient_matrix_UB_11 0.0632984000 _diffrn_orient_matrix_UB_12 0.0344538000 _diffrn_orient_matrix_UB_13 0.0423972000 _diffrn_orient_matrix_UB_21 0.0119671000 _diffrn_orient_matrix_UB_22 0.0262069000 _diffrn_orient_matrix_UB_23 -0.0654493000 _diffrn_orient_matrix_UB_31 -0.0701211000 _diffrn_orient_matrix_UB_32 0.0355255000 _diffrn_orient_matrix_UB_33 0.0072293000 _diffrn_radiation_collimation monochromator _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_xray_symbol Mo _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_source_type 'sealed tube' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 4125 _reflns_number_total 4501 _reflns_odcompleteness_completeness 99.07 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 31.44 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; XS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.346 _refine_diff_density_min -0.468 _refine_diff_density_rms 0.070 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.025(9) _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 331 _refine_ls_number_reflns 4501 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0376 _refine_ls_R_factor_gt 0.0322 _refine_ls_restrained_S_all 1.045 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0300P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0670 _refine_ls_wR_factor_ref 0.0702 _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. During the refinement H atoms of the water molecule tended to move along the direction of the hydrogen bonds (as it often happens in case of strong hydrogen bonds) so O-H distances have been restrained by DFIX 1.05 0.01 O1W H1WB O1W H1WA ; _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 Ga1 Ga 0.55459(3) 0.459910(18) 0.98518(3) 0.01598(7) Uani 1 1 d . . . O1 O 0.6408(3) 0.31516(15) 1.0316(2) 0.0203(4) Uani 1 1 d . . . O1W O 0.1541(4) 0.4163(2) 0.3875(3) 0.0542(8) Uani 1 1 d D . . H1WA H 0.2766 0.4570 0.3852 0.081 Uiso 1 1 d RD . . H1WB H 0.1311 0.4203 0.4985 0.081 Uiso 1 1 d RD . . O2 O 0.7716(3) 0.17586(15) 0.9509(2) 0.0238(4) Uani 1 1 d . . . O3 O 0.4648(2) 0.4655(2) 1.16362(18) 0.0211(4) Uani 1 1 d . . . O4 O 0.4940(3) 0.53555(18) 1.3891(2) 0.0323(5) Uani 1 1 d . . . O5 O 0.3416(3) 0.40176(16) 0.8631(2) 0.0229(4) Uani 1 1 d . . . O6 O 0.1101(3) 0.43183(15) 0.6820(2) 0.0260(5) Uani 1 1 d . . . N1 N 0.7824(3) 0.4501(2) 0.8761(2) 0.0174(4) Uani 1 1 d . . . N2 N 0.7364(3) 0.57798(18) 1.0935(2) 0.0180(5) Uani 1 1 d . . . N3 N 0.4829(3) 0.58979(18) 0.8499(3) 0.0162(4) Uani 1 1 d . . . C1 C 0.9474(3) 0.4681(4) 0.9932(3) 0.0206(5) Uani 1 1 d . . . C2 C 0.9017(4) 0.5148(2) 1.1345(3) 0.0196(5) Uani 1 1 d . . . C3 C 0.7552(5) 0.6617(2) 0.9832(3) 0.0170(6) Uani 1 1 d . . . C4 C 0.6629(4) 0.6292(2) 0.8281(3) 0.0160(5) Uani 1 1 d . . . C5 C 0.7570(4) 0.5371(2) 0.7670(3) 0.0172(5) Uani 1 1 d . . . C6 C 0.7871(4) 0.3390(2) 0.8222(3) 0.0184(6) Uani 1 1 d . . . C7 C 0.7312(4) 0.2700(3) 0.9424(4) 0.0200(7) Uani 1 1 d . . . C8 C 0.6624(4) 0.6165(2) 1.2238(3) 0.0200(6) Uani 1 1 d . . . C9 C 0.5334(4) 0.5327(2) 1.2658(3) 0.0208(6) Uani 1 1 d . . . C10 C 0.3460(4) 0.5613(2) 0.7198(3) 0.0199(5) Uani 1 1 d . . . C11 C 0.2547(3) 0.4570(3) 0.7557(3) 0.0202(5) Uani 1 1 d . . . C12 C 0.6659(4) 0.3167(2) 0.6747(3) 0.0251(6) Uani 1 1 d . . . C13 C 0.8025(5) 0.6533(3) 1.3524(4) 0.0303(7) Uani 1 1 d . . . C14 C 0.6525(4) 0.7227(2) 0.7236(3) 0.0215(6) Uani 1 1 d . . . C15 C 0.2113(5) 0.6486(3) 0.6710(4) 0.0274(6) Uani 1 1 d . . . H1A H 1.008(5) 0.396(3) 1.015(4) 0.027(9) Uiso 1 1 d . . . H1B H 1.033(4) 0.517(3) 0.960(3) 0.014(8) Uiso 1 1 d . . . H2A H 0.871(3) 0.462(3) 1.196(3) 0.011(6) Uiso 1 1 d . . . H2B H 0.994(5) 0.557(3) 1.182(4) 0.038(10) Uiso 1 1 d . . . H3 H 0.447(4) 0.635(2) 0.899(3) 0.011(7) Uiso 1 1 d . . . H3A H 0.709(5) 0.720(3) 1.006(4) 0.019(8) Uiso 1 1 d . . . H3B H 0.880(5) 0.675(2) 0.996(3) 0.018(8) Uiso 1 1 d . . . H5A H 0.686(4) 0.503(2) 0.673(3) 0.017(8) Uiso 1 1 d . . . H5B H 0.866(5) 0.556(3) 0.740(4) 0.039(10) Uiso 1 1 d . . . H6 H 0.903(4) 0.324(2) 0.809(3) 0.002(6) Uiso 1 1 d . . . H8 H 0.584(4) 0.680(2) 1.184(3) 0.018(8) Uiso 1 1 d . . . H10 H 0.404(4) 0.5462(19) 0.641(3) 0.003(6) Uiso 1 1 d . . . H12A H 0.709(4) 0.356(2) 0.597(3) 0.017(8) Uiso 1 1 d . . . H12B H 0.531(5) 0.338(3) 0.678(4) 0.040(10) Uiso 1 1 d . . . H12C H 0.661(5) 0.235(3) 0.656(4) 0.023(9) Uiso 1 1 d . . . H13A H 0.887(5) 0.599(3) 1.396(4) 0.027(9) Uiso 1 1 d . . . H13B H 0.879(6) 0.701(3) 1.320(4) 0.039(11) Uiso 1 1 d . . . H13C H 0.767(6) 0.676(3) 1.415(5) 0.042(12) Uiso 1 1 d . . . H14A H 0.597(5) 0.774(3) 0.756(4) 0.020(8) Uiso 1 1 d . . . H14B H 0.581(5) 0.701(3) 0.626(4) 0.024(9) Uiso 1 1 d . . . H14C H 0.777(5) 0.747(3) 0.723(4) 0.033(10) Uiso 1 1 d . . . H15A H 0.151(5) 0.673(3) 0.751(4) 0.039(10) Uiso 1 1 d . . . H15B H 0.280(5) 0.713(3) 0.637(4) 0.027(9) Uiso 1 1 d . . . H15C H 0.125(7) 0.623(4) 0.590(6) 0.068(14) 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 Ga1 0.01339(12) 0.01853(12) 0.01822(12) 0.00099(15) 0.00864(9) 0.00052(15) O1 0.0179(10) 0.0194(9) 0.0267(11) 0.0034(8) 0.0124(9) 0.0011(8) O1W 0.0505(18) 0.0698(19) 0.0408(15) -0.0109(13) 0.0042(13) 0.0023(14) O2 0.0214(11) 0.0206(10) 0.0309(11) -0.0008(9) 0.0083(9) 0.0012(8) O3 0.0212(8) 0.0247(9) 0.0209(8) 0.0013(12) 0.0126(7) 0.0002(12) O4 0.0386(13) 0.0420(13) 0.0212(11) 0.0018(9) 0.0184(10) 0.0000(10) O5 0.0184(10) 0.0250(10) 0.0271(11) 0.0022(8) 0.0091(9) -0.0019(8) O6 0.0137(9) 0.0380(14) 0.0268(10) -0.0043(8) 0.0056(8) -0.0058(8) N1 0.0141(9) 0.0187(12) 0.0208(9) 0.0008(11) 0.0070(8) 0.0000(11) N2 0.0165(12) 0.0234(11) 0.0162(11) 0.0000(9) 0.0085(9) 0.0038(10) N3 0.0126(11) 0.0212(11) 0.0160(11) -0.0024(9) 0.0059(9) 0.0012(9) C1 0.0136(11) 0.0231(15) 0.0262(12) -0.0008(16) 0.0067(9) 0.0018(14) C2 0.0142(13) 0.0240(14) 0.0205(14) 0.0014(11) 0.0032(11) -0.0002(11) C3 0.0141(16) 0.0193(15) 0.0194(14) -0.0009(11) 0.0074(12) 0.0000(11) C4 0.0134(13) 0.0188(12) 0.0179(13) -0.0006(10) 0.0083(10) 0.0002(10) C5 0.0151(13) 0.0172(13) 0.0224(14) 0.0002(11) 0.0116(12) -0.0034(10) C6 0.0179(14) 0.0182(13) 0.0220(14) -0.0021(11) 0.0115(11) 0.0009(11) C7 0.0126(15) 0.0209(14) 0.0273(17) -0.0021(12) 0.0063(13) -0.0020(11) C8 0.0208(14) 0.0244(14) 0.0162(13) -0.0005(10) 0.0071(11) 0.0023(11) C9 0.0195(14) 0.0239(13) 0.0211(14) 0.0017(11) 0.0093(11) 0.0053(11) C10 0.0154(13) 0.0281(14) 0.0172(13) 0.0001(11) 0.0058(11) -0.0039(11) C11 0.0147(11) 0.0264(11) 0.0229(11) -0.0032(18) 0.0119(9) 0.0000(18) C12 0.0314(17) 0.0232(14) 0.0237(14) -0.0020(12) 0.0133(13) -0.0022(13) C13 0.0263(18) 0.044(2) 0.0211(16) -0.0086(14) 0.0055(14) -0.0013(16) C14 0.0243(16) 0.0198(13) 0.0232(15) -0.0007(11) 0.0115(13) 0.0021(12) C15 0.0224(16) 0.0328(16) 0.0260(16) 0.0046(13) 0.0021(13) -0.0010(14) _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 Ga1 O1 1.9666(19) . ? Ga1 O3 1.8952(15) . ? Ga1 O5 1.934(2) . ? Ga1 N1 2.1578(19) . ? Ga1 N2 2.150(2) . ? Ga1 N3 2.075(2) . ? O1 C7 1.298(4) . ? O1W H1WA 1.0657 . ? O1W H1WB 1.0708 . ? O2 C7 1.229(4) . ? O3 C9 1.304(4) . ? O4 C9 1.228(3) . ? O5 C11 1.289(4) . ? O6 C11 1.220(3) . ? N1 C1 1.510(3) . ? N1 C5 1.480(4) . ? N1 C6 1.494(4) . ? N2 C2 1.476(4) . ? N2 C3 1.494(4) . ? N2 C8 1.499(3) . ? N3 C4 1.501(3) . ? N3 C10 1.477(4) . ? N3 H3 0.81(3) . ? C1 C2 1.528(4) . ? C1 H1A 1.02(4) . ? C1 H1B 0.99(3) . ? C2 H2A 0.93(3) . ? C2 H2B 0.92(4) . ? C3 C4 1.527(4) . ? C3 H3A 0.86(3) . ? C3 H3B 0.95(3) . ? C4 C5 1.528(4) . ? C4 C14 1.520(4) . ? C5 H5A 1.03(3) . ? C5 H5B 0.93(4) . ? C6 C7 1.532(4) . ? C6 C12 1.519(4) . ? C6 H6 0.93(3) . ? C8 C9 1.541(4) . ? C8 C13 1.511(4) . ? C8 H8 1.02(3) . ? C10 C11 1.555(5) . ? C10 C15 1.516(4) . ? C10 H10 0.94(3) . ? C12 H12A 0.97(3) . ? C12 H12B 1.06(4) . ? C12 H12C 1.04(3) . ? C13 H13A 0.98(4) . ? C13 H13B 0.92(4) . ? C13 H13C 0.74(4) . ? C14 H14A 0.86(3) . ? C14 H14B 1.00(4) . ? C14 H14C 0.99(4) . ? C15 H15A 0.98(4) . ? C15 H15B 1.04(4) . ? C15 H15C 0.96(5) . ? 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 Ga1 N1 77.60(9) . . ? O1 Ga1 N2 112.89(10) . . ? O1 Ga1 N3 155.41(9) . . ? O3 Ga1 O1 90.24(10) . . ? O3 Ga1 O5 97.08(8) . . ? O3 Ga1 N1 148.73(8) . . ? O3 Ga1 N2 82.76(9) . . ? O3 Ga1 N3 113.33(10) . . ? O5 Ga1 O1 88.82(9) . . ? O5 Ga1 N1 111.15(8) . . ? O5 Ga1 N2 158.28(9) . . ? O5 Ga1 N3 81.67(9) . . ? N2 Ga1 N1 75.93(9) . . ? N3 Ga1 N1 84.75(9) . . ? N3 Ga1 N2 78.54(9) . . ? C7 O1 Ga1 117.81(19) . . ? H1WA O1W H1WB 107.1 . . ? C9 O3 Ga1 119.46(18) . . ? C11 O5 Ga1 119.5(2) . . ? C1 N1 Ga1 106.68(14) . . ? C5 N1 Ga1 105.03(16) . . ? C5 N1 C1 111.0(3) . . ? C5 N1 C6 118.9(2) . . ? C6 N1 Ga1 106.28(16) . . ? C6 N1 C1 108.2(3) . . ? C2 N2 Ga1 100.49(17) . . ? C2 N2 C3 112.0(2) . . ? C2 N2 C8 113.4(2) . . ? C3 N2 Ga1 108.18(17) . . ? C3 N2 C8 114.3(2) . . ? C8 N2 Ga1 107.16(17) . . ? Ga1 N3 H3 108(2) . . ? C4 N3 Ga1 101.58(16) . . ? C4 N3 H3 104(2) . . ? C10 N3 Ga1 111.09(17) . . ? C10 N3 C4 119.5(2) . . ? C10 N3 H3 111(2) . . ? N1 C1 C2 112.2(2) . . ? N1 C1 H1A 107(2) . . ? N1 C1 H1B 112.3(19) . . ? C2 C1 H1A 110(2) . . ? C2 C1 H1B 106.4(19) . . ? H1A C1 H1B 109(3) . . ? N2 C2 C1 107.9(2) . . ? N2 C2 H2A 104.2(17) . . ? N2 C2 H2B 110(2) . . ? C1 C2 H2A 111(2) . . ? C1 C2 H2B 111(2) . . ? H2A C2 H2B 112(3) . . ? N2 C3 C4 111.1(2) . . ? N2 C3 H3A 110(2) . . ? N2 C3 H3B 105.2(19) . . ? C4 C3 H3A 109(2) . . ? C4 C3 H3B 116.0(19) . . ? H3A C3 H3B 105(3) . . ? N3 C4 C3 103.5(2) . . ? N3 C4 C5 107.1(2) . . ? N3 C4 C14 113.7(2) . . ? C3 C4 C5 112.8(2) . . ? C14 C4 C3 110.1(2) . . ? C14 C4 C5 109.5(2) . . ? N1 C5 C4 109.2(2) . . ? N1 C5 H5A 104.2(16) . . ? N1 C5 H5B 111(2) . . ? C4 C5 H5A 114.9(16) . . ? C4 C5 H5B 113(2) . . ? H5A C5 H5B 104(3) . . ? N1 C6 C7 105.6(2) . . ? N1 C6 C12 115.2(2) . . ? N1 C6 H6 108.5(16) . . ? C7 C6 H6 112.2(17) . . ? C12 C6 C7 109.8(2) . . ? C12 C6 H6 105.7(16) . . ? O1 C7 C6 117.1(3) . . ? O2 C7 O1 122.8(3) . . ? O2 C7 C6 120.0(3) . . ? N2 C8 C9 109.1(2) . . ? N2 C8 C13 114.6(3) . . ? N2 C8 H8 104.3(17) . . ? C9 C8 H8 106.0(18) . . ? C13 C8 C9 113.7(2) . . ? C13 C8 H8 108.4(18) . . ? O3 C9 C8 117.0(2) . . ? O4 C9 O3 123.7(3) . . ? O4 C9 C8 119.2(3) . . ? N3 C10 C11 108.0(2) . . ? N3 C10 C15 113.3(2) . . ? N3 C10 H10 108.5(17) . . ? C11 C10 H10 106.6(15) . . ? C15 C10 C11 112.4(2) . . ? C15 C10 H10 107.9(16) . . ? O5 C11 C10 116.1(2) . . ? O6 C11 O5 124.3(3) . . ? O6 C11 C10 119.6(3) . . ? C6 C12 H12A 109.5(18) . . ? C6 C12 H12B 111(2) . . ? C6 C12 H12C 109(2) . . ? H12A C12 H12B 110(3) . . ? H12A C12 H12C 113(3) . . ? H12B C12 H12C 104(3) . . ? C8 C13 H13A 115(2) . . ? C8 C13 H13B 110(3) . . ? C8 C13 H13C 116(4) . . ? H13A C13 H13B 101(3) . . ? H13A C13 H13C 105(4) . . ? H13B C13 H13C 110(4) . . ? C4 C14 H14A 110(2) . . ? C4 C14 H14B 108.0(19) . . ? C4 C14 H14C 108(2) . . ? H14A C14 H14B 108(3) . . ? H14A C14 H14C 107(3) . . ? H14B C14 H14C 116(3) . . ? C10 C15 H15A 113(2) . . ? C10 C15 H15B 108(2) . . ? C10 C15 H15C 108(3) . . ? H15A C15 H15B 108(3) . . ? H15A C15 H15C 110(4) . . ? H15B C15 H15C 110(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 O1W H1WA O4 1.07 1.92 2.985(4) 176.8 1_554 O1W H1WB O6 1.07 1.73 2.804(3) 175.5 . loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z 0 -1 0 0.1375 -0.0001 -0.9995 0.0001 -0.0344 -0.0262 -0.0355 0 1 0 0.1375 0.0001 0.9995 -0.0001 0.0344 0.0262 0.0355 -1 0 0 0.0695 -0.9992 0.0001 0.0002 -0.0632 -0.0120 0.0701 1 0 0 0.0695 0.9992 -0.0001 -0.0002 0.0632 0.0120 -0.0701 0 0 -1 0.0279 0.0005 0.0003 -0.9991 -0.0423 0.0654 -0.0072 0 0 1 0.0279 -0.0005 -0.0003 0.9991 0.0423 -0.0654 0.0072 data_[Ga.L3]_12srv172 _database_code_depnum_ccdc_archive 'CCDC 906038' #TrackingRef 'web_deposit_cif_file_2_DmitryYufit_1350321914.Ga_L3.cif' _audit_creation_date 2012-09-03 _audit_creation_method ; Olex2 1.2-beta (compiled 2012.08.15 svn.r2450, GUI svn.r4314) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C17 H20 Ga N3 O6' _chemical_formula_sum 'C17 H20 Ga N3 O6' _chemical_formula_weight 432.08 _chemical_melting_point ? _chemical_oxdiff_formula 'C17 H23 Ga1 N3 O6' 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' Ga Ga 0.2307 1.6083 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 10.6961(8) _cell_length_b 13.0778(12) _cell_length_c 13.8414(12) _cell_angle_alpha 116.076(9) _cell_angle_beta 105.208(7) _cell_angle_gamma 92.002(7) _cell_volume 1652.8(2) _cell_formula_units_Z 4 _cell_measurement_reflns_used 2363 _cell_measurement_temperature 120 _cell_measurement_theta_max 32.6038 _cell_measurement_theta_min 2.5142 _exptl_absorpt_coefficient_mu 1.709 _exptl_absorpt_correction_T_max 0.878 _exptl_absorpt_correction_T_min 0.653 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_crystal_colour 'dull light colourless' _exptl_crystal_colour_lustre dull _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.736 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 888 _exptl_crystal_size_max 0.4732 _exptl_crystal_size_mid 0.1113 _exptl_crystal_size_min 0.082 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0881 _diffrn_reflns_av_unetI/netI 0.1285 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 16836 _diffrn_reflns_theta_full 27.50 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_theta_min 2.52 _diffrn_ambient_temperature 120 _diffrn_detector CCD _diffrn_detector_area_resol_mean 16.1511 _diffrn_detector_type Sapphire3 _diffrn_measured_fraction_theta_full 0.9994 _diffrn_measured_fraction_theta_max 0.9941 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -42.00 42.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - -26.3429 57.0000 -30.0000 84 #__ type_ start__ end____ width___ exp.time_ 2 omega -98.00 18.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - -26.3429 -19.0000 150.0000 116 #__ type_ start__ end____ width___ exp.time_ 3 omega -38.00 48.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - 26.9679 -57.0000 90.0000 86 #__ type_ start__ end____ width___ exp.time_ 4 omega 42.00 92.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - 26.9679 -137.0000 -79.0000 50 #__ type_ start__ end____ width___ exp.time_ 5 omega 58.00 85.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - 26.9679 179.0000 -120.0000 27 #__ type_ start__ end____ width___ exp.time_ 6 omega 23.00 77.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - 26.9679 19.0000 90.0000 54 #__ type_ start__ end____ width___ exp.time_ 7 omega 40.00 90.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - 26.9679 -137.0000 100.0000 50 #__ type_ start__ end____ width___ exp.time_ 8 omega -96.00 -14.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - -26.3429 -77.0000 -30.0000 82 ; _diffrn_measurement_device '3-circle diffractometer' _diffrn_measurement_device_type 'Xcalibur, Sapphire3, Gemini ultra' _diffrn_measurement_method \w-scan _diffrn_orient_matrix_UB_11 -0.0631794000 _diffrn_orient_matrix_UB_12 -0.0137200000 _diffrn_orient_matrix_UB_13 -0.0399767000 _diffrn_orient_matrix_UB_21 0.0273711000 _diffrn_orient_matrix_UB_22 -0.0266777000 _diffrn_orient_matrix_UB_23 -0.0447314000 _diffrn_orient_matrix_UB_31 -0.0113136000 _diffrn_orient_matrix_UB_32 -0.0534709000 _diffrn_orient_matrix_UB_33 0.0005662000 _diffrn_radiation_collimation monochromator _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_xray_symbol Mo _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_source_type 'sealed tube' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 4908 _reflns_number_total 7571 _reflns_odcompleteness_completeness 99.94 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 30.44 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; XS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 1.530 _refine_diff_density_min -0.797 _refine_diff_density_rms 0.168 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 487 _refine_ls_number_reflns 7571 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1144 _refine_ls_R_factor_gt 0.0699 _refine_ls_restrained_S_all 1.063 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0700P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1553 _refine_ls_wR_factor_ref 0.1864 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 Ga1 Ga 0.37853(6) 0.80813(5) 0.17525(6) 0.01516(18) Uani 1 1 d . . . O1 O 0.2406(4) 0.8887(3) 0.1357(4) 0.0192(9) Uani 1 1 d . . . O2 O 0.1879(4) 1.0631(3) 0.2252(4) 0.0216(9) Uani 1 1 d . . . O3 O 0.2691(4) 0.6595(3) 0.0817(4) 0.0189(9) Uani 1 1 d . . . O4 O 0.2329(4) 0.4897(3) -0.0713(4) 0.0282(10) Uani 1 1 d . . . O5 O 0.3365(4) 0.8491(3) 0.3127(4) 0.0208(9) Uani 1 1 d . . . O6 O 0.4092(4) 0.8829(4) 0.4925(4) 0.0243(10) Uani 1 1 d . . . N1 N 0.4904(4) 0.9615(4) 0.2024(4) 0.0154(10) Uani 1 1 d . . . N2 N 0.4768(4) 0.7469(4) 0.0489(4) 0.0166(10) Uani 1 1 d . . . N3 N 0.5562(4) 0.7885(4) 0.2681(4) 0.0144(10) Uani 1 1 d . . . H3 H 0.5598 0.7100 0.2385 0.017 Uiso 1 1 calc R . . C1 C 0.4863(6) 0.9498(5) 0.0887(5) 0.0203(13) Uani 1 1 d . . . H1A H 0.5744 0.9807 0.0928 0.024 Uiso 1 1 calc R . . H1B H 0.4236 0.9968 0.0691 0.024 Uiso 1 1 calc R . . C2 C 0.4449(6) 0.8240(5) -0.0052(5) 0.0192(13) Uani 1 1 d . . . H2A H 0.3494 0.8079 -0.0453 0.023 Uiso 1 1 calc R . . H2B H 0.4930 0.8102 -0.0607 0.023 Uiso 1 1 calc R . . C3 C 0.6211(5) 0.7677(5) 0.1085(5) 0.0178(12) Uani 1 1 d . . . H3B H 0.6698 0.8059 0.0781 0.021 Uiso 1 1 calc R . . H3C H 0.6502 0.6927 0.0935 0.021 Uiso 1 1 calc R . . C4 C 0.6536(5) 0.8436(5) 0.2365(5) 0.0167(12) Uani 1 1 d . . . C5 C 0.6267(5) 0.9684(5) 0.2698(5) 0.0164(12) Uani 1 1 d . . . H5A H 0.6366 1.0099 0.3516 0.020 Uiso 1 1 calc R . . H5B H 0.6903 1.0111 0.2540 0.020 Uiso 1 1 calc R . . C6 C 0.4157(5) 1.0514(5) 0.2572(5) 0.0158(12) Uani 1 1 d . . . H6A H 0.4346 1.1199 0.2469 0.019 Uiso 1 1 calc R . . H6B H 0.4412 1.0757 0.3393 0.019 Uiso 1 1 calc R . . C7 C 0.2686(6) 0.9989(5) 0.2015(6) 0.0216(13) Uani 1 1 d . . . C8 C 0.4187(6) 0.6251(5) -0.0293(5) 0.0228(13) Uani 1 1 d . . . H8A H 0.4854 0.5762 -0.0221 0.027 Uiso 1 1 calc R . . H8B H 0.3932 0.6139 -0.1079 0.027 Uiso 1 1 calc R . . C9 C 0.2984(5) 0.5866(5) -0.0066(5) 0.0186(12) Uani 1 1 d . . . C10 C 0.5610(5) 0.8319(5) 0.3859(5) 0.0200(13) Uani 1 1 d . . . H10C H 0.6270 0.9037 0.4337 0.024 Uiso 1 1 calc R . . H10D H 0.5882 0.7740 0.4115 0.024 Uiso 1 1 calc R . . C11 C 0.4261(6) 0.8565(5) 0.3993(5) 0.0182(12) Uani 1 1 d . . . C12 C 0.7965(6) 0.8435(5) 0.2945(5) 0.0203(13) Uani 1 1 d . . . C13 C 0.8989(6) 0.9124(5) 0.2930(6) 0.0248(14) Uani 1 1 d . . . H13 H 0.8791 0.9630 0.2608 0.030 Uiso 1 1 calc R . . C14 C 1.0290(6) 0.9068(6) 0.3385(6) 0.0321(16) Uani 1 1 d . . . H14 H 1.0972 0.9543 0.3372 0.039 Uiso 1 1 calc R . . C15 C 1.0617(6) 0.8336(6) 0.3856(6) 0.0322(16) Uani 1 1 d . . . H15 H 1.1511 0.8312 0.4175 0.039 Uiso 1 1 calc R . . C16 C 0.9601(6) 0.7633(6) 0.3851(6) 0.0277(14) Uani 1 1 d . . . H16 H 0.9805 0.7115 0.4159 0.033 Uiso 1 1 calc R . . C17 C 0.8293(6) 0.7681(5) 0.3401(6) 0.0227(13) Uani 1 1 d . . . H17 H 0.7614 0.7195 0.3404 0.027 Uiso 1 1 calc R . . Ga1A Ga 0.24814(6) 0.30555(5) 0.18760(6) 0.01595(18) Uani 1 1 d . . . O1A O 0.2791(4) 0.1595(3) 0.0857(4) 0.0220(9) Uani 1 1 d . . . O2A O 0.1920(4) -0.0058(3) -0.0717(4) 0.0233(9) Uani 1 1 d . . . O3A O 0.3671(4) 0.3875(3) 0.1493(4) 0.0204(9) Uani 1 1 d . . . O4A O 0.4844(4) 0.5623(3) 0.2172(4) 0.0248(10) Uani 1 1 d . . . O5A O 0.3822(4) 0.3399(3) 0.3241(4) 0.0205(9) Uani 1 1 d . . . O6A O 0.4312(4) 0.3569(4) 0.4994(4) 0.0289(10) Uani 1 1 d . . . N1A N 0.0589(4) 0.2531(4) 0.0623(4) 0.0165(10) Uani 1 1 d . . . N2A N 0.1729(4) 0.4630(4) 0.2208(4) 0.0185(11) Uani 1 1 d . . . N3A N 0.1252(4) 0.2808(4) 0.2768(4) 0.0187(11) Uani 1 1 d . . . H3A H 0.0905 0.2026 0.2426 0.022 Uiso 1 1 calc R . . C1A C 0.0655(6) 0.3339(5) 0.0142(5) 0.0216(13) Uani 1 1 d . . . H1AA H -0.0193 0.3217 -0.0432 0.026 Uiso 1 1 calc R . . H1AB H 0.1355 0.3207 -0.0225 0.026 Uiso 1 1 calc R . . C2A C 0.0956(6) 0.4572(5) 0.1117(5) 0.0199(13) Uani 1 1 d . . . H2AA H 0.1457 0.5087 0.0945 0.024 Uiso 1 1 calc R . . H2AB H 0.0119 0.4851 0.1187 0.024 Uiso 1 1 calc R . . C3A C 0.0876(6) 0.4680(5) 0.2914(5) 0.0209(13) Uani 1 1 d . . . H3AA H 0.0214 0.5175 0.2845 0.025 Uiso 1 1 calc R . . H3AB H 0.1415 0.5019 0.3719 0.025 Uiso 1 1 calc R . . C4A C 0.0175(6) 0.3437(5) 0.2510(5) 0.0193(13) Uani 1 1 d . . . C5A C -0.0435(5) 0.2743(5) 0.1217(5) 0.0190(13) Uani 1 1 d . . . H5AA H -0.0935 0.1992 0.1025 0.023 Uiso 1 1 calc R . . H5AB H -0.1060 0.3172 0.0947 0.023 Uiso 1 1 calc R . . C6A C 0.0508(6) 0.1326(5) -0.0199(5) 0.0207(13) Uani 1 1 d . . . H6AA H 0.0205 0.1249 -0.0971 0.025 Uiso 1 1 calc R . . H6AB H -0.0153 0.0828 -0.0137 0.025 Uiso 1 1 calc R . . C7A C 0.1820(5) 0.0904(5) -0.0026(5) 0.0174(12) Uani 1 1 d . . . C8A C 0.2946(5) 0.5501(5) 0.2768(5) 0.0199(13) Uani 1 1 d . . . H8AA H 0.3325 0.5661 0.3564 0.024 Uiso 1 1 calc R . . H8AB H 0.2762 0.6232 0.2755 0.024 Uiso 1 1 calc R . . C9A C 0.3906(5) 0.4978(5) 0.2093(5) 0.0182(12) Uani 1 1 d . . . C10A C 0.2046(5) 0.3164(5) 0.3936(5) 0.0192(12) Uani 1 1 d . . . H10A H 0.1869 0.2549 0.4141 0.023 Uiso 1 1 calc R . . H10B H 0.1791 0.3873 0.4451 0.023 Uiso 1 1 calc R . . C11A C 0.3511(6) 0.3395(5) 0.4092(5) 0.0215(13) Uani 1 1 d . . . C12A C -0.0895(5) 0.3449(5) 0.3054(5) 0.0178(12) Uani 1 1 d . . . C13A C -0.1835(6) 0.4165(5) 0.3026(5) 0.0212(13) Uani 1 1 d . . . H13A H -0.1757 0.4677 0.2719 0.025 Uiso 1 1 calc R . . C14A C -0.2885(6) 0.4135(6) 0.3442(6) 0.0285(15) Uani 1 1 d . . . H14A H -0.3513 0.4628 0.3422 0.034 Uiso 1 1 calc R . . C15A C -0.3006(6) 0.3377(5) 0.3889(5) 0.0258(14) Uani 1 1 d . . . H15A H -0.3715 0.3354 0.4177 0.031 Uiso 1 1 calc R . . C16A C -0.2095(6) 0.2665(6) 0.3910(6) 0.0284(15) Uani 1 1 d . . . H16A H -0.2176 0.2152 0.4217 0.034 Uiso 1 1 calc R . . C17A C -0.1059(6) 0.2687(5) 0.3488(5) 0.0224(13) Uani 1 1 d . . . H17A H -0.0451 0.2175 0.3493 0.027 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ga1 0.0129(3) 0.0156(3) 0.0194(4) 0.0089(3) 0.0074(3) 0.0035(2) O1 0.015(2) 0.015(2) 0.026(2) 0.0064(18) 0.0079(17) 0.0039(15) O2 0.021(2) 0.016(2) 0.031(3) 0.0099(19) 0.0128(19) 0.0104(16) O3 0.017(2) 0.019(2) 0.021(2) 0.0087(18) 0.0077(17) 0.0015(16) O4 0.027(2) 0.021(2) 0.030(3) 0.004(2) 0.013(2) -0.0025(18) O5 0.013(2) 0.026(2) 0.029(3) 0.016(2) 0.0097(18) 0.0078(16) O6 0.026(2) 0.029(2) 0.020(2) 0.009(2) 0.0145(19) 0.0078(18) N1 0.008(2) 0.017(2) 0.021(3) 0.009(2) 0.0036(19) 0.0039(17) N2 0.017(2) 0.013(2) 0.022(3) 0.010(2) 0.006(2) 0.0021(18) N3 0.014(2) 0.011(2) 0.023(3) 0.011(2) 0.010(2) 0.0062(17) C1 0.019(3) 0.026(3) 0.026(4) 0.017(3) 0.013(3) 0.010(2) C2 0.017(3) 0.027(3) 0.025(4) 0.020(3) 0.010(3) 0.007(2) C3 0.014(3) 0.017(3) 0.028(4) 0.011(3) 0.013(2) 0.010(2) C4 0.010(3) 0.024(3) 0.024(3) 0.016(3) 0.007(2) 0.005(2) C5 0.013(3) 0.021(3) 0.015(3) 0.007(2) 0.006(2) 0.004(2) C6 0.014(3) 0.015(3) 0.024(3) 0.011(3) 0.011(2) 0.006(2) C7 0.020(3) 0.026(3) 0.027(4) 0.018(3) 0.011(3) 0.009(2) C8 0.021(3) 0.026(3) 0.021(3) 0.009(3) 0.010(3) 0.006(2) C9 0.018(3) 0.018(3) 0.021(3) 0.010(3) 0.007(2) 0.006(2) C10 0.021(3) 0.019(3) 0.020(3) 0.010(3) 0.005(2) 0.002(2) C11 0.022(3) 0.014(3) 0.021(3) 0.009(2) 0.008(3) 0.002(2) C12 0.018(3) 0.021(3) 0.025(4) 0.011(3) 0.010(3) 0.007(2) C13 0.024(3) 0.027(3) 0.028(4) 0.016(3) 0.007(3) 0.007(3) C14 0.017(3) 0.043(4) 0.042(5) 0.027(4) 0.008(3) 0.002(3) C15 0.018(3) 0.055(5) 0.032(4) 0.026(4) 0.008(3) 0.013(3) C16 0.027(3) 0.033(4) 0.026(4) 0.015(3) 0.009(3) 0.008(3) C17 0.018(3) 0.025(3) 0.029(4) 0.015(3) 0.010(3) 0.008(2) Ga1A 0.0130(3) 0.0159(3) 0.0213(4) 0.0093(3) 0.0078(3) 0.0038(2) O1A 0.018(2) 0.025(2) 0.031(3) 0.017(2) 0.0111(19) 0.0081(17) O2A 0.020(2) 0.024(2) 0.026(3) 0.009(2) 0.0103(18) 0.0053(17) O3A 0.019(2) 0.016(2) 0.030(3) 0.0099(19) 0.0132(18) 0.0031(16) O4A 0.025(2) 0.018(2) 0.038(3) 0.014(2) 0.017(2) 0.0052(17) O5A 0.016(2) 0.028(2) 0.020(2) 0.0116(19) 0.0074(17) 0.0044(16) O6A 0.019(2) 0.044(3) 0.026(3) 0.019(2) 0.005(2) 0.0078(19) N1A 0.015(2) 0.016(2) 0.024(3) 0.011(2) 0.012(2) 0.0050(18) N2A 0.016(2) 0.019(2) 0.025(3) 0.011(2) 0.012(2) 0.0042(19) N3A 0.016(2) 0.021(3) 0.023(3) 0.013(2) 0.007(2) 0.0055(19) C1A 0.017(3) 0.028(3) 0.029(4) 0.020(3) 0.008(3) 0.005(2) C2A 0.019(3) 0.021(3) 0.028(4) 0.017(3) 0.011(3) 0.003(2) C3A 0.020(3) 0.018(3) 0.026(4) 0.008(3) 0.013(3) 0.005(2) C4A 0.021(3) 0.011(3) 0.029(4) 0.011(3) 0.011(3) 0.005(2) C5A 0.014(3) 0.020(3) 0.031(4) 0.013(3) 0.017(3) 0.006(2) C6A 0.019(3) 0.019(3) 0.024(3) 0.009(3) 0.009(3) 0.005(2) C7A 0.020(3) 0.017(3) 0.022(3) 0.013(3) 0.010(2) 0.005(2) C8A 0.013(3) 0.016(3) 0.027(4) 0.007(3) 0.008(2) -0.001(2) C9A 0.017(3) 0.020(3) 0.019(3) 0.010(3) 0.006(2) 0.007(2) C10A 0.019(3) 0.019(3) 0.021(3) 0.011(3) 0.005(2) 0.002(2) C11A 0.020(3) 0.015(3) 0.024(4) 0.008(3) 0.003(3) 0.002(2) C12A 0.014(3) 0.020(3) 0.017(3) 0.006(2) 0.005(2) 0.001(2) C13A 0.020(3) 0.016(3) 0.025(4) 0.007(3) 0.008(3) 0.003(2) C14A 0.020(3) 0.030(3) 0.033(4) 0.011(3) 0.011(3) 0.005(3) C15A 0.014(3) 0.036(4) 0.018(3) 0.005(3) 0.004(2) 0.001(3) C16A 0.025(3) 0.036(4) 0.030(4) 0.019(3) 0.010(3) -0.003(3) C17A 0.020(3) 0.029(3) 0.024(4) 0.017(3) 0.006(3) 0.007(2) _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 Ga1 O1 1.945(4) . ? Ga1 O3 1.912(4) . ? Ga1 O5 1.918(4) . ? Ga1 N1 2.128(4) . ? Ga1 N2 2.144(5) . ? Ga1 N3 2.091(4) . ? O1 C7 1.292(7) . ? O2 C7 1.231(7) . ? O3 C9 1.303(7) . ? O4 C9 1.228(7) . ? O5 C11 1.285(7) . ? O6 C11 1.244(7) . ? N1 C1 1.501(8) . ? N1 C5 1.486(7) . ? N1 C6 1.481(7) . ? N2 C2 1.500(7) . ? N2 C3 1.497(7) . ? N2 C8 1.468(7) . ? N3 H3 0.9300 . ? N3 C4 1.504(6) . ? N3 C10 1.457(7) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C1 C2 1.536(8) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 H3B 0.9900 . ? C3 H3C 0.9900 . ? C3 C4 1.533(8) . ? C4 C5 1.550(8) . ? C4 C12 1.529(8) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C6 C7 1.538(8) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C8 C9 1.521(8) . ? C10 H10C 0.9900 . ? C10 H10D 0.9900 . ? C10 C11 1.531(8) . ? C12 C13 1.404(8) . ? C12 C17 1.396(8) . ? C13 H13 0.9500 . ? C13 C14 1.387(8) . ? C14 H14 0.9500 . ? C14 C15 1.385(9) . ? C15 H15 0.9500 . ? C15 C16 1.396(9) . ? C16 H16 0.9500 . ? C16 C17 1.390(8) . ? C17 H17 0.9500 . ? Ga1A O1A 1.915(4) . ? Ga1A O3A 1.951(4) . ? Ga1A O5A 1.901(4) . ? Ga1A N1A 2.143(5) . ? Ga1A N2A 2.139(5) . ? Ga1A N3A 2.128(5) . ? O1A C7A 1.299(7) . ? O2A C7A 1.231(7) . ? O3A C9A 1.283(7) . ? O4A C9A 1.239(6) . ? O5A C11A 1.308(7) . ? O6A C11A 1.232(7) . ? N1A C1A 1.485(7) . ? N1A C5A 1.498(7) . ? N1A C6A 1.466(7) . ? N2A C2A 1.487(8) . ? N2A C3A 1.486(7) . ? N2A C8A 1.478(7) . ? N3A H3A 0.9300 . ? N3A C4A 1.496(7) . ? N3A C10A 1.465(7) . ? C1A H1AA 0.9900 . ? C1A H1AB 0.9900 . ? C1A C2A 1.531(8) . ? C2A H2AA 0.9900 . ? C2A H2AB 0.9900 . ? C3A H3AA 0.9900 . ? C3A H3AB 0.9900 . ? C3A C4A 1.554(7) . ? C4A C5A 1.540(9) . ? C4A C12A 1.523(8) . ? C5A H5AA 0.9900 . ? C5A H5AB 0.9900 . ? C6A H6AA 0.9900 . ? C6A H6AB 0.9900 . ? C6A C7A 1.524(8) . ? C8A H8AA 0.9900 . ? C8A H8AB 0.9900 . ? C8A C9A 1.544(8) . ? C10A H10A 0.9900 . ? C10A H10B 0.9900 . ? C10A C11A 1.524(8) . ? C12A C13A 1.402(8) . ? C12A C17A 1.398(8) . ? C13A H13A 0.9500 . ? C13A C14A 1.397(8) . ? C14A H14A 0.9500 . ? C14A C15A 1.398(9) . ? C15A H15A 0.9500 . ? C15A C16A 1.375(9) . ? C16A H16A 0.9500 . ? C16A C17A 1.386(8) . ? C17A H17A 0.9500 . ? 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 Ga1 N1 78.44(16) . . ? O1 Ga1 N2 110.00(18) . . ? O1 Ga1 N3 157.22(17) . . ? O3 Ga1 O1 93.19(16) . . ? O3 Ga1 O5 99.83(17) . . ? O3 Ga1 N1 153.33(18) . . ? O3 Ga1 N2 82.98(17) . . ? O3 Ga1 N3 108.66(17) . . ? O5 Ga1 O1 87.73(17) . . ? O5 Ga1 N1 105.02(18) . . ? O5 Ga1 N2 161.96(17) . . ? O5 Ga1 N3 82.40(17) . . ? N1 Ga1 N2 76.41(17) . . ? N3 Ga1 N1 84.36(17) . . ? N3 Ga1 N2 79.84(18) . . ? C7 O1 Ga1 112.5(4) . . ? C9 O3 Ga1 118.7(3) . . ? C11 O5 Ga1 118.8(4) . . ? C1 N1 Ga1 107.7(3) . . ? C5 N1 Ga1 106.5(3) . . ? C5 N1 C1 111.0(4) . . ? C6 N1 Ga1 102.3(3) . . ? C6 N1 C1 111.0(4) . . ? C6 N1 C5 117.4(5) . . ? C2 N2 Ga1 101.8(3) . . ? C3 N2 Ga1 107.7(3) . . ? C3 N2 C2 111.4(4) . . ? C8 N2 Ga1 107.9(3) . . ? C8 N2 C2 112.5(5) . . ? C8 N2 C3 114.6(4) . . ? Ga1 N3 H3 108.1 . . ? C4 N3 Ga1 101.1(3) . . ? C4 N3 H3 108.1 . . ? C10 N3 Ga1 110.1(3) . . ? C10 N3 H3 108.1 . . ? C10 N3 C4 120.7(4) . . ? N1 C1 H1A 109.1 . . ? N1 C1 H1B 109.1 . . ? N1 C1 C2 112.7(4) . . ? H1A C1 H1B 107.8 . . ? C2 C1 H1A 109.1 . . ? C2 C1 H1B 109.1 . . ? N2 C2 C1 107.9(5) . . ? N2 C2 H2A 110.1 . . ? N2 C2 H2B 110.1 . . ? C1 C2 H2A 110.1 . . ? C1 C2 H2B 110.1 . . ? H2A C2 H2B 108.4 . . ? N2 C3 H3B 109.3 . . ? N2 C3 H3C 109.3 . . ? N2 C3 C4 111.7(4) . . ? H3B C3 H3C 107.9 . . ? C4 C3 H3B 109.3 . . ? C4 C3 H3C 109.3 . . ? N3 C4 C3 104.0(4) . . ? N3 C4 C5 105.7(4) . . ? N3 C4 C12 113.1(4) . . ? C3 C4 C5 113.5(5) . . ? C12 C4 C3 109.1(4) . . ? C12 C4 C5 111.3(5) . . ? N1 C5 C4 108.1(4) . . ? N1 C5 H5A 110.1 . . ? N1 C5 H5B 110.1 . . ? C4 C5 H5A 110.1 . . ? C4 C5 H5B 110.1 . . ? H5A C5 H5B 108.4 . . ? N1 C6 H6A 110.2 . . ? N1 C6 H6B 110.2 . . ? N1 C6 C7 107.6(4) . . ? H6A C6 H6B 108.5 . . ? C7 C6 H6A 110.2 . . ? C7 C6 H6B 110.2 . . ? O1 C7 C6 116.2(5) . . ? O2 C7 O1 125.4(5) . . ? O2 C7 C6 118.4(5) . . ? N2 C8 H8A 109.2 . . ? N2 C8 H8B 109.2 . . ? N2 C8 C9 112.2(5) . . ? H8A C8 H8B 107.9 . . ? C9 C8 H8A 109.2 . . ? C9 C8 H8B 109.2 . . ? O3 C9 C8 117.7(5) . . ? O4 C9 O3 122.8(5) . . ? O4 C9 C8 119.5(5) . . ? N3 C10 H10C 109.6 . . ? N3 C10 H10D 109.6 . . ? N3 C10 C11 110.4(5) . . ? H10C C10 H10D 108.1 . . ? C11 C10 H10C 109.6 . . ? C11 C10 H10D 109.6 . . ? O5 C11 C10 117.4(5) . . ? O6 C11 O5 123.9(5) . . ? O6 C11 C10 118.8(5) . . ? C13 C12 C4 119.8(5) . . ? C17 C12 C4 121.6(5) . . ? C17 C12 C13 118.3(5) . . ? C12 C13 H13 119.9 . . ? C14 C13 C12 120.3(6) . . ? C14 C13 H13 119.9 . . ? C13 C14 H14 119.3 . . ? C15 C14 C13 121.5(6) . . ? C15 C14 H14 119.3 . . ? C14 C15 H15 120.8 . . ? C14 C15 C16 118.4(6) . . ? C16 C15 H15 120.8 . . ? C15 C16 H16 119.6 . . ? C17 C16 C15 120.7(6) . . ? C17 C16 H16 119.6 . . ? C12 C17 H17 119.6 . . ? C16 C17 C12 120.8(6) . . ? C16 C17 H17 119.6 . . ? O1A Ga1A O3A 91.04(16) . . ? O1A Ga1A N1A 83.31(17) . . ? O1A Ga1A N2A 151.50(19) . . ? O1A Ga1A N3A 110.10(18) . . ? O3A Ga1A N1A 108.58(17) . . ? O3A Ga1A N2A 77.91(16) . . ? O3A Ga1A N3A 158.46(18) . . ? O5A Ga1A O1A 101.50(18) . . ? O5A Ga1A O3A 89.81(17) . . ? O5A Ga1A N1A 161.03(17) . . ? O5A Ga1A N2A 104.61(19) . . ? O5A Ga1A N3A 82.17(17) . . ? N2A Ga1A N1A 75.71(18) . . ? N3A Ga1A N1A 78.96(18) . . ? N3A Ga1A N2A 84.79(17) . . ? C7A O1A Ga1A 118.3(3) . . ? C9A O3A Ga1A 114.9(4) . . ? C11A O5A Ga1A 120.1(4) . . ? C1A N1A Ga1A 101.7(3) . . ? C1A N1A C5A 111.1(4) . . ? C5A N1A Ga1A 108.0(4) . . ? C6A N1A Ga1A 107.2(3) . . ? C6A N1A C1A 112.5(5) . . ? C6A N1A C5A 115.3(4) . . ? C2A N2A Ga1A 109.0(4) . . ? C3A N2A Ga1A 104.7(3) . . ? C3A N2A C2A 111.3(4) . . ? C8A N2A Ga1A 102.2(3) . . ? C8A N2A C2A 112.2(4) . . ? C8A N2A C3A 116.6(5) . . ? Ga1A N3A H3A 108.5 . . ? C4A N3A Ga1A 100.6(3) . . ? C4A N3A H3A 108.5 . . ? C10A N3A Ga1A 109.1(3) . . ? C10A N3A H3A 108.5 . . ? C10A N3A C4A 120.8(5) . . ? N1A C1A H1AA 110.2 . . ? N1A C1A H1AB 110.2 . . ? N1A C1A C2A 107.7(5) . . ? H1AA C1A H1AB 108.5 . . ? C2A C1A H1AA 110.2 . . ? C2A C1A H1AB 110.2 . . ? N2A C2A C1A 111.7(5) . . ? N2A C2A H2AA 109.3 . . ? N2A C2A H2AB 109.3 . . ? C1A C2A H2AA 109.3 . . ? C1A C2A H2AB 109.3 . . ? H2AA C2A H2AB 107.9 . . ? N2A C3A H3AA 109.9 . . ? N2A C3A H3AB 109.9 . . ? N2A C3A C4A 109.0(5) . . ? H3AA C3A H3AB 108.3 . . ? C4A C3A H3AA 109.9 . . ? C4A C3A H3AB 109.9 . . ? N3A C4A C3A 105.2(4) . . ? N3A C4A C5A 103.3(4) . . ? N3A C4A C12A 114.6(5) . . ? C5A C4A C3A 113.5(5) . . ? C12A C4A C3A 111.5(5) . . ? C12A C4A C5A 108.6(5) . . ? N1A C5A C4A 112.0(5) . . ? N1A C5A H5AA 109.2 . . ? N1A C5A H5AB 109.2 . . ? C4A C5A H5AA 109.2 . . ? C4A C5A H5AB 109.2 . . ? H5AA C5A H5AB 107.9 . . ? N1A C6A H6AA 109.0 . . ? N1A C6A H6AB 109.0 . . ? N1A C6A C7A 112.8(5) . . ? H6AA C6A H6AB 107.8 . . ? C7A C6A H6AA 109.0 . . ? C7A C6A H6AB 109.0 . . ? O1A C7A C6A 117.5(5) . . ? O2A C7A O1A 123.0(5) . . ? O2A C7A C6A 119.5(5) . . ? N2A C8A H8AA 110.5 . . ? N2A C8A H8AB 110.5 . . ? N2A C8A C9A 106.2(5) . . ? H8AA C8A H8AB 108.7 . . ? C9A C8A H8AA 110.5 . . ? C9A C8A H8AB 110.5 . . ? O3A C9A C8A 116.1(5) . . ? O4A C9A O3A 124.4(5) . . ? O4A C9A C8A 119.5(5) . . ? N3A C10A H10A 109.4 . . ? N3A C10A H10B 109.4 . . ? N3A C10A C11A 111.4(5) . . ? H10A C10A H10B 108.0 . . ? C11A C10A H10A 109.4 . . ? C11A C10A H10B 109.4 . . ? O5A C11A C10A 116.4(5) . . ? O6A C11A O5A 124.6(5) . . ? O6A C11A C10A 119.0(6) . . ? C13A C12A C4A 119.5(5) . . ? C17A C12A C4A 122.3(5) . . ? C17A C12A C13A 117.9(5) . . ? C12A C13A H13A 119.5 . . ? C14A C13A C12A 121.0(6) . . ? C14A C13A H13A 119.5 . . ? C13A C14A H14A 120.2 . . ? C13A C14A C15A 119.6(6) . . ? C15A C14A H14A 120.2 . . ? C14A C15A H15A 120.1 . . ? C16A C15A C14A 119.8(6) . . ? C16A C15A H15A 120.1 . . ? C15A C16A H16A 119.7 . . ? C15A C16A C17A 120.7(6) . . ? C17A C16A H16A 119.7 . . ? C12A C17A H17A 119.5 . . ? C16A C17A C12A 121.1(6) . . ? C16A C17A H17A 119.5 . . ? 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 N3 H3 O4A 0.93 1.93 2.750(6) 145.5 . N3A H3A O2 0.93 2.09 2.768(6) 129.2 1_545 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z 0 -2 1 0.2228 0.0000 -2.0000 1.0000 -0.0125 0.0086 0.1075 0 2 -1 0.2468 -0.0000 2.0000 -1.0000 0.0125 -0.0086 -0.1075 -1 0 1 0.0512 -1.0000 0.0000 1.0000 0.0232 -0.0721 0.0119 1 0 -1 0.0512 1.0000 -0.0000 -1.0000 -0.0232 0.0721 -0.0119 0 0 1 0.0410 0.0000 0.0000 1.0000 -0.0400 -0.0447 0.0006 0 0 -1 0.0410 -0.0000 -0.0000 -1.0000 0.0400 0.0447 -0.0006 1 0 0 0.0510 1.0000 -0.0000 0.0000 -0.0632 0.0274 -0.0113 -1 0 0 0.0510 -1.0000 0.0000 -0.0000 0.0632 -0.0274 0.0113 -12 12 -4 0.1453 -12.0000 12.0000 -4.0000 0.7534 -0.4697 -0.5082 _shelx_res_file ; TITL 12srv172 in P-1 #2 CELL 0.71073 10.696086 13.077847 13.841427 116.0762 105.2079 92.002 ZERR 4 0.000826 0.001246 0.001173 0.0089 0.007 0.007 LATT 1 SFAC C H Ga N O UNIT 68 80 4 12 24 EQIV $1 +X,-1+Y,+Z L.S. 11 PLAN 5 TEMP -153.15 HTAB N3 O4A HTAB N3A O2_$1 REM reset to P-1 #2 BOND $h fmap 2 acta OMIT -2 55 OMIT 4 -7 1 OMIT 2 -8 2 OMIT 0 -2 1 OMIT 0 2 0 OMIT 0 -4 1 REM Q:/Struc/12S/12srv172/struct/12srv172.hkl WGHT 0.070000 FVAR 2.20925 GA1 3 0.378525 0.808127 0.175255 11.00000 0.01294 0.01559 = 0.01944 0.00887 0.00744 0.00352 O1 5 0.240565 0.888739 0.135676 11.00000 0.01476 0.01479 = 0.02572 0.00638 0.00790 0.00385 O2 5 0.187894 1.063130 0.225233 11.00000 0.02082 0.01593 = 0.03060 0.00991 0.01277 0.01036 O3 5 0.269106 0.659509 0.081684 11.00000 0.01664 0.01916 = 0.02115 0.00870 0.00772 0.00148 O4 5 0.232922 0.489725 -0.071331 11.00000 0.02675 0.02051 = 0.03032 0.00398 0.01308 -0.00247 O5 5 0.336543 0.849071 0.312741 11.00000 0.01319 0.02626 = 0.02871 0.01575 0.00972 0.00779 O6 5 0.409188 0.882934 0.492453 11.00000 0.02609 0.02913 = 0.02008 0.00921 0.01449 0.00778 N1 4 0.490358 0.961503 0.202401 11.00000 0.00817 0.01748 = 0.02056 0.00916 0.00356 0.00386 N2 4 0.476779 0.746853 0.048896 11.00000 0.01672 0.01317 = 0.02210 0.01020 0.00596 0.00210 N3 4 0.556170 0.788514 0.268101 11.00000 0.01434 0.01113 = 0.02340 0.01054 0.00981 0.00616 AFIX 13 H3 2 0.559804 0.710003 0.238472 11.00000 -1.20000 AFIX 0 C1 1 0.486252 0.949766 0.088671 11.00000 0.01876 0.02582 = 0.02626 0.01677 0.01304 0.00952 AFIX 23 H1A 2 0.574382 0.980728 0.092842 11.00000 -1.20000 H1B 2 0.423576 0.996762 0.069133 11.00000 -1.20000 AFIX 0 C2 1 0.444913 0.824011 -0.005215 11.00000 0.01744 0.02672 = 0.02480 0.01972 0.00979 0.00683 AFIX 23 H2A 2 0.349432 0.807906 -0.045291 11.00000 -1.20000 H2B 2 0.493026 0.810164 -0.060747 11.00000 -1.20000 AFIX 0 C3 1 0.621067 0.767734 0.108453 11.00000 0.01410 0.01698 = 0.02775 0.01066 0.01325 0.01011 AFIX 23 H3B 2 0.669820 0.805942 0.078068 11.00000 -1.20000 H3C 2 0.650219 0.692688 0.093541 11.00000 -1.20000 AFIX 0 C4 1 0.653636 0.843606 0.236454 11.00000 0.01005 0.02370 = 0.02388 0.01623 0.00740 0.00509 C5 1 0.626721 0.968447 0.269808 11.00000 0.01290 0.02111 = 0.01495 0.00683 0.00647 0.00382 AFIX 23 H5A 2 0.636577 1.009866 0.351584 11.00000 -1.20000 H5B 2 0.690282 1.011142 0.254038 11.00000 -1.20000 AFIX 0 C6 1 0.415736 1.051380 0.257198 11.00000 0.01359 0.01544 = 0.02426 0.01125 0.01087 0.00562 AFIX 23 H6A 2 0.434601 1.119936 0.246874 11.00000 -1.20000 H6B 2 0.441244 1.075694 0.339282 11.00000 -1.20000 AFIX 0 C7 1 0.268594 0.998924 0.201454 11.00000 0.02033 0.02564 = 0.02747 0.01759 0.01086 0.00860 C8 1 0.418671 0.625150 -0.029315 11.00000 0.02138 0.02628 = 0.02110 0.00938 0.00983 0.00568 AFIX 23 H8A 2 0.485410 0.576213 -0.022052 11.00000 -1.20000 H8B 2 0.393200 0.613909 -0.107899 11.00000 -1.20000 AFIX 0 C9 1 0.298413 0.586576 -0.006606 11.00000 0.01773 0.01817 = 0.02134 0.00991 0.00664 0.00615 C10 1 0.561040 0.831894 0.385925 11.00000 0.02055 0.01863 = 0.02030 0.00979 0.00466 0.00160 AFIX 23 H10C 2 0.626985 0.903721 0.433712 11.00000 -1.20000 H10D 2 0.588240 0.773996 0.411489 11.00000 -1.20000 AFIX 0 C11 1 0.426051 0.856506 0.399349 11.00000 0.02214 0.01350 = 0.02089 0.00901 0.00808 0.00193 C12 1 0.796453 0.843496 0.294520 11.00000 0.01765 0.02114 = 0.02451 0.01062 0.00963 0.00680 C13 1 0.898926 0.912382 0.293037 11.00000 0.02353 0.02740 = 0.02757 0.01633 0.00746 0.00683 AFIX 43 H13 2 0.879083 0.963006 0.260790 11.00000 -1.20000 AFIX 0 C14 1 1.029004 0.906822 0.338461 11.00000 0.01725 0.04340 = 0.04226 0.02664 0.00762 0.00215 AFIX 43 H14 2 1.097185 0.954322 0.337207 11.00000 -1.20000 AFIX 0 C15 1 1.061717 0.833577 0.385602 11.00000 0.01785 0.05456 = 0.03162 0.02569 0.00812 0.01324 AFIX 43 H15 2 1.151124 0.831249 0.417460 11.00000 -1.20000 AFIX 0 C16 1 0.960069 0.763263 0.385146 11.00000 0.02735 0.03254 = 0.02621 0.01547 0.00936 0.00775 AFIX 43 H16 2 0.980500 0.711514 0.415940 11.00000 -1.20000 AFIX 0 C17 1 0.829275 0.768121 0.340132 11.00000 0.01819 0.02540 = 0.02912 0.01458 0.01049 0.00792 AFIX 43 H17 2 0.761391 0.719534 0.340421 11.00000 -1.20000 AFIX 0 GA1A 3 0.248142 0.305554 0.187595 11.00000 0.01299 0.01594 = 0.02132 0.00927 0.00779 0.00383 O1A 5 0.279145 0.159502 0.085703 11.00000 0.01826 0.02463 = 0.03087 0.01726 0.01109 0.00809 O2A 5 0.191955 -0.005826 -0.071706 11.00000 0.02033 0.02360 = 0.02551 0.00907 0.01030 0.00531 O3A 5 0.367118 0.387472 0.149270 11.00000 0.01865 0.01587 = 0.02957 0.00992 0.01315 0.00308 O4A 5 0.484412 0.562307 0.217174 11.00000 0.02461 0.01815 = 0.03809 0.01450 0.01708 0.00522 O5A 5 0.382163 0.339885 0.324123 11.00000 0.01597 0.02784 = 0.01960 0.01162 0.00739 0.00441 O6A 5 0.431189 0.356944 0.499363 11.00000 0.01927 0.04409 = 0.02564 0.01916 0.00474 0.00780 N1A 4 0.058854 0.253071 0.062314 11.00000 0.01507 0.01623 = 0.02393 0.01075 0.01188 0.00497 N2A 4 0.172889 0.462976 0.220816 11.00000 0.01610 0.01903 = 0.02461 0.01059 0.01201 0.00415 N3A 4 0.125205 0.280822 0.276754 11.00000 0.01568 0.02108 = 0.02320 0.01319 0.00671 0.00550 AFIX 13 H3A 2 0.090476 0.202560 0.242571 11.00000 -1.20000 AFIX 0 C1A 1 0.065530 0.333928 0.014244 11.00000 0.01726 0.02799 = 0.02861 0.02048 0.00760 0.00526 AFIX 23 H1AA 2 -0.019316 0.321656 -0.043162 11.00000 -1.20000 H1AB 2 0.135541 0.320697 -0.022456 11.00000 -1.20000 AFIX 0 C2A 1 0.095591 0.457176 0.111669 11.00000 0.01927 0.02089 = 0.02821 0.01703 0.01085 0.00298 AFIX 23 H2AA 2 0.145673 0.508745 0.094534 11.00000 -1.20000 H2AB 2 0.011940 0.485062 0.118655 11.00000 -1.20000 AFIX 0 C3A 1 0.087587 0.468016 0.291426 11.00000 0.02008 0.01769 = 0.02614 0.00773 0.01311 0.00548 AFIX 23 H3AA 2 0.021383 0.517473 0.284456 11.00000 -1.20000 H3AB 2 0.141499 0.501890 0.371864 11.00000 -1.20000 AFIX 0 C4A 1 0.017500 0.343682 0.251000 11.00000 0.02108 0.01142 = 0.02923 0.01056 0.01134 0.00458 C5A 1 -0.043530 0.274283 0.121683 11.00000 0.01391 0.02012 = 0.03141 0.01333 0.01711 0.00629 AFIX 23 H5AA 2 -0.093520 0.199191 0.102464 11.00000 -1.20000 H5AB 2 -0.106001 0.317181 0.094706 11.00000 -1.20000 AFIX 0 C6A 1 0.050826 0.132577 -0.019877 11.00000 0.01930 0.01907 = 0.02373 0.00886 0.00852 0.00494 AFIX 23 H6AA 2 0.020474 0.124866 -0.097144 11.00000 -1.20000 H6AB 2 -0.015289 0.082785 -0.013689 11.00000 -1.20000 AFIX 0 C7A 1 0.181978 0.090432 -0.002561 11.00000 0.02012 0.01732 = 0.02152 0.01272 0.00986 0.00536 C8A 1 0.294605 0.550054 0.276767 11.00000 0.01340 0.01598 = 0.02732 0.00691 0.00788 -0.00101 AFIX 23 H8AA 2 0.332461 0.566110 0.356428 11.00000 -1.20000 H8AB 2 0.276163 0.623175 0.275470 11.00000 -1.20000 AFIX 0 C9A 1 0.390562 0.497771 0.209341 11.00000 0.01739 0.01986 = 0.01942 0.01044 0.00615 0.00652 C10A 1 0.204604 0.316404 0.393641 11.00000 0.01921 0.01872 = 0.02095 0.01086 0.00517 0.00232 AFIX 23 H10A 2 0.186850 0.254905 0.414059 11.00000 -1.20000 H10B 2 0.179137 0.387331 0.445059 11.00000 -1.20000 AFIX 0 C11A 1 0.351053 0.339519 0.409248 11.00000 0.02049 0.01500 = 0.02435 0.00757 0.00258 0.00161 C12A 1 -0.089462 0.344901 0.305410 11.00000 0.01391 0.01983 = 0.01702 0.00643 0.00499 0.00060 C13A 1 -0.183504 0.416469 0.302605 11.00000 0.02031 0.01625 = 0.02469 0.00668 0.00833 0.00272 AFIX 43 H13A 2 -0.175664 0.467747 0.271910 11.00000 -1.20000 AFIX 0 C14A 1 -0.288498 0.413548 0.344223 11.00000 0.02002 0.03044 = 0.03297 0.01122 0.01124 0.00527 AFIX 43 H14A 2 -0.351299 0.462765 0.342191 11.00000 -1.20000 AFIX 0 C15A 1 -0.300580 0.337723 0.388892 11.00000 0.01430 0.03565 = 0.01772 0.00512 0.00364 0.00097 AFIX 43 H15A 2 -0.371476 0.335428 0.417699 11.00000 -1.20000 AFIX 0 C16A 1 -0.209464 0.266458 0.390985 11.00000 0.02461 0.03552 = 0.03016 0.01948 0.00983 -0.00255 AFIX 43 H16A 2 -0.217574 0.215224 0.421679 11.00000 -1.20000 AFIX 0 C17A 1 -0.105922 0.268654 0.348753 11.00000 0.01990 0.02868 = 0.02364 0.01658 0.00622 0.00713 AFIX 43 H17A 2 -0.045137 0.217498 0.349271 11.00000 -1.20000 HKLF 4 REM 12srv172 in P-1 #2 REM R1 = 0.0699 for 4908 Fo > 4sig(Fo) and 0.1144 for all 7571 data REM 487 parameters refined using 0 restraints END WGHT 0.0729 0.0000 REM Highest difference peak 1.530, deepest hole -0.797, 1-sigma level 0.168 Q1 1 -0.1296 0.1950 -0.1850 11.00000 0.05 1.53 Q2 1 0.4864 0.6953 -0.1712 11.00000 0.05 1.53 Q3 1 0.2710 0.3449 0.2758 11.00000 0.05 1.51 Q4 1 0.3568 0.7700 0.0935 11.00000 0.05 1.40 Q5 1 0.3960 0.8472 0.2641 11.00000 0.05 1.38 REM The information below was added by Olex2. REM REM R1 = 0.0699 for 4908 Fo > 4sig(Fo) and n/a for all 21914 data REM n/a parameters refined using n/a restraints REM Highest difference peak 1.53, deepest hole -0.80 REM Mean Shift 0, Max Shift 0. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = n/a REM R1_gt = 0.0699 REM wR_ref = 0.1864 REM GOOF = 1.063 REM Shift_max = 0 REM Shift_mean = 0 REM Reflections_all = 21914 REM Reflections_gt = 4908 REM Parameters = n/a REM Hole = 1.53 REM Peak = -0.80 REM Flack = n/a ; _shelx_res_file_MD5 a96b61e39cd56ae4bf144b7c9c8f6f13 data_[ESI_1]_12srv123 _database_code_depnum_ccdc_archive 'CCDC 906039' #TrackingRef 'web_deposit_cif_file_3_DmitryYufit_1350321914.ESI_1.cif' _audit_creation_date 2012-06-27 _audit_creation_method ; Olex2 1.2-beta (compiled 2012.05.09 svn.r2324, GUI svn.r4230) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C20 H25 N3 O2' _chemical_formula_sum 'C20 H25 N3 O2' _chemical_formula_weight 339.43 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_H-M_alt 'C 1 2/c 1' _space_group_name_Hall '-C 2yc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y, -z+1/2' 3 'x+1/2, y+1/2, z' 4 '-x+1/2, y+1/2, -z+1/2' 5 '-x, -y, -z' 6 'x, -y, z-1/2' 7 '-x+1/2, -y+1/2, -z' 8 'x+1/2, -y+1/2, z-1/2' _cell_length_a 32.4876(13) _cell_length_b 6.0545(2) _cell_length_c 20.2683(8) _cell_angle_alpha 90.00 _cell_angle_beta 111.467(10) _cell_angle_gamma 90.00 _cell_volume 3710.1(2) _cell_formula_units_Z 8 _cell_measurement_reflns_used 4238 _cell_measurement_temperature 120 _cell_measurement_theta_max 29.24 _cell_measurement_theta_min 2.16 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 0.1913 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2006/1 (Bruker,2006) was used for absorption correction. R(int) was 0.0388 before and 0.0272 after correction. The Ratio of minimum to maximum transmission is 0.1913. The \l/2 correction factor is 0.0015. ; _exptl_crystal_colour 'dull light colourless' _exptl_crystal_colour_lustre dull _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.215 _exptl_crystal_density_meas . _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 1456 _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.16 _exptl_special_details ; The data collection nominally covered a full sphere of reciprocal space by a combination of 3 sets of \w scans each set at different \f and/or 2\q angles and each scan (5 s exposure) covering -0.300\% degrees in \w. The crystal to detector distance was 4.85 cm. ; _diffrn_reflns_av_R_equivalents 0.0342 _diffrn_reflns_av_unetI/netI 0.0332 _diffrn_reflns_limit_h_max 42 _diffrn_reflns_limit_h_min -42 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_number 17258 _diffrn_reflns_theta_full 28.00 _diffrn_reflns_theta_max 28.00 _diffrn_reflns_theta_min 1.35 _diffrn_ambient_temperature 120 _diffrn_detector 'CCD area detector' _diffrn_detector_area_resol_mean 5.6 _diffrn_detector_type 'Bruker SMART CCD 6000 area detector' _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker SMART CCD 6000 area detector' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_xray_symbol K-L~3~ _diffrn_source 'sealed X-ray tube' _diffrn_source_current 35.0 _diffrn_source_power 1.75 _diffrn_source_target Mo _diffrn_source_type 'sealed X-ray tube' _diffrn_source_voltage 50.0 _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 3332 _reflns_number_total 4452 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'SAINT v6.45A (Bruker, 2003)' _computing_data_collection 'SMART v5.625 (Bruker, 2001)' _computing_data_reduction 'SAINT v6.45A (Bruker, 2003)' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; XS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.591 _refine_diff_density_min -0.215 _refine_diff_density_rms 0.049 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 315 _refine_ls_number_reflns 4452 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0671 _refine_ls_R_factor_gt 0.0482 _refine_ls_restrained_S_all 1.030 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0700P)^2^+3.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1252 _refine_ls_wR_factor_ref 0.1427 _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. ; _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.65102(5) -0.1060(2) 0.53349(7) 0.0446(3) Uani 1 1 d . . . O2 O 0.63870(5) 0.2108(2) 0.56938(7) 0.0525(4) Uani 1 1 d . . . N1 N 0.61669(4) 0.1041(2) 0.32781(6) 0.0260(3) Uani 1 1 d . . . N2 N 0.56888(4) 0.3490(2) 0.40534(6) 0.0261(3) Uani 1 1 d . . . N3 N 0.64395(4) 0.0925(2) 0.52491(7) 0.0293(3) Uani 1 1 d . . . C1 C 0.56896(5) 0.1486(3) 0.29684(8) 0.0305(3) Uani 1 1 d . . . C2 C 0.55458(5) 0.3498(3) 0.32781(8) 0.0303(3) Uani 1 1 d . . . C3 C 0.61623(5) 0.3999(3) 0.43795(8) 0.0271(3) Uani 1 1 d . . . C4 C 0.64492(5) 0.1939(2) 0.45596(7) 0.0245(3) Uani 1 1 d . . . C5 C 0.62868(5) 0.0125(2) 0.39942(7) 0.0252(3) Uani 1 1 d . . . C6 C 0.69325(5) 0.2523(3) 0.47212(8) 0.0300(3) Uani 1 1 d . . . H6A H 0.7016 0.3737 0.5048 0.045 Uiso 1 1 calc R . . H6B H 0.6972 0.2933 0.4290 0.045 Uiso 1 1 calc R . . H6C H 0.7115 0.1268 0.4927 0.045 Uiso 1 1 calc R . . C7 C 0.62962(5) -0.0499(3) 0.28235(8) 0.0300(3) Uani 1 1 d . . . C8 C 0.67911(5) -0.0629(3) 0.30370(8) 0.0284(3) Uani 1 1 d . . . C9 C 0.70277(5) 0.1175(3) 0.29362(8) 0.0314(3) Uani 1 1 d . . . C10 C 0.74865(6) 0.1115(3) 0.31600(9) 0.0363(4) Uani 1 1 d . . . C11 C 0.77132(6) -0.0772(3) 0.34900(9) 0.0408(4) Uani 1 1 d . . . C12 C 0.74828(7) -0.2581(3) 0.35792(10) 0.0426(4) Uani 1 1 d . . . C13 C 0.70238(6) -0.2515(3) 0.33531(9) 0.0355(4) Uani 1 1 d . . . C14 C 0.54221(5) 0.5051(3) 0.42848(9) 0.0292(3) Uani 1 1 d . . . C15 C 0.49486(5) 0.4308(3) 0.40779(8) 0.0264(3) Uani 1 1 d . . . C16 C 0.48526(5) 0.2204(3) 0.42657(8) 0.0281(3) Uani 1 1 d . . . C17 C 0.44172(5) 0.1555(3) 0.41145(8) 0.0300(3) Uani 1 1 d . . . C18 C 0.40716(5) 0.2995(3) 0.37680(8) 0.0314(3) Uani 1 1 d . . . C19 C 0.41620(5) 0.5071(3) 0.35705(8) 0.0324(4) Uani 1 1 d . . . C20 C 0.45990(5) 0.5718(3) 0.37214(8) 0.0302(3) Uani 1 1 d . . . H1A H 0.5611(6) 0.175(3) 0.2445(10) 0.035(5) Uiso 1 1 d . . . H1B H 0.5530(6) 0.015(3) 0.3037(10) 0.036(5) Uiso 1 1 d . . . H2A H 0.5660(6) 0.487(3) 0.3111(10) 0.033(5) Uiso 1 1 d . . . H2B H 0.5214(6) 0.354(3) 0.3070(10) 0.036(5) Uiso 1 1 d . . . H3A H 0.6221(6) 0.486(3) 0.4808(10) 0.032(5) Uiso 1 1 d . . . H3B H 0.6267(6) 0.488(3) 0.4062(9) 0.028(4) Uiso 1 1 d . . . H5A H 0.6522(6) -0.099(3) 0.4083(9) 0.029(4) Uiso 1 1 d . . . H5B H 0.6040(6) -0.063(3) 0.4054(9) 0.028(4) Uiso 1 1 d . . . H7A H 0.6153(6) 0.005(3) 0.2327(10) 0.028(4) Uiso 1 1 d . . . H7B H 0.6164(6) -0.201(3) 0.2810(9) 0.035(5) Uiso 1 1 d . . . H9 H 0.6867(6) 0.249(3) 0.2713(11) 0.042(5) Uiso 1 1 d . . . H10 H 0.7638(7) 0.242(4) 0.3075(12) 0.053(6) Uiso 1 1 d . . . H11 H 0.8030(8) -0.081(4) 0.3657(12) 0.054(6) Uiso 1 1 d . . . H12 H 0.7635(8) -0.388(4) 0.3807(13) 0.062(7) Uiso 1 1 d . . . H13 H 0.6861(6) -0.381(3) 0.3415(10) 0.039(5) Uiso 1 1 d . . . H14A H 0.5558(6) 0.515(3) 0.4805(10) 0.030(4) Uiso 1 1 d . . . H14B H 0.5437(6) 0.658(3) 0.4075(10) 0.033(5) Uiso 1 1 d . . . H16 H 0.5098(6) 0.118(3) 0.4527(10) 0.035(5) Uiso 1 1 d . . . H17 H 0.4370(6) 0.008(3) 0.4276(10) 0.037(5) Uiso 1 1 d . . . H18 H 0.3759(6) 0.255(3) 0.3660(10) 0.037(5) Uiso 1 1 d . . . H19 H 0.3930(6) 0.607(3) 0.3313(10) 0.039(5) Uiso 1 1 d . . . H20 H 0.4661(6) 0.719(3) 0.3578(10) 0.042(5) 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 O1 0.0584(8) 0.0427(7) 0.0356(7) 0.0120(5) 0.0207(6) 0.0095(6) O2 0.0778(10) 0.0530(8) 0.0383(7) -0.0070(6) 0.0350(7) -0.0001(7) N1 0.0274(6) 0.0299(6) 0.0213(6) -0.0005(5) 0.0095(5) 0.0017(5) N2 0.0223(6) 0.0306(7) 0.0242(6) -0.0025(5) 0.0074(5) 0.0001(5) N3 0.0266(6) 0.0375(8) 0.0246(6) 0.0003(5) 0.0105(5) -0.0018(5) C1 0.0270(7) 0.0403(9) 0.0227(7) -0.0023(6) 0.0073(6) -0.0005(7) C2 0.0265(7) 0.0388(9) 0.0241(7) 0.0015(6) 0.0075(6) 0.0027(7) C3 0.0231(7) 0.0258(7) 0.0307(7) -0.0020(6) 0.0078(6) -0.0028(6) C4 0.0239(7) 0.0294(7) 0.0205(6) 0.0003(5) 0.0082(5) -0.0012(6) C5 0.0294(7) 0.0252(7) 0.0217(7) 0.0009(5) 0.0102(6) -0.0012(6) C6 0.0238(7) 0.0392(9) 0.0274(7) -0.0001(6) 0.0096(6) -0.0027(6) C7 0.0348(8) 0.0322(8) 0.0237(7) -0.0032(6) 0.0116(6) -0.0003(7) C8 0.0353(8) 0.0301(8) 0.0222(7) -0.0016(6) 0.0133(6) 0.0044(6) C9 0.0356(8) 0.0312(8) 0.0289(7) 0.0011(6) 0.0136(6) 0.0046(7) C10 0.0378(9) 0.0424(10) 0.0319(8) -0.0056(7) 0.0166(7) -0.0024(7) C11 0.0358(9) 0.0554(11) 0.0307(8) -0.0051(8) 0.0116(7) 0.0121(8) C12 0.0492(11) 0.0420(10) 0.0364(9) 0.0041(8) 0.0156(8) 0.0180(8) C13 0.0459(10) 0.0317(9) 0.0322(8) 0.0011(6) 0.0183(7) 0.0069(7) C14 0.0288(7) 0.0267(8) 0.0321(8) -0.0037(6) 0.0112(6) 0.0004(6) C15 0.0290(7) 0.0282(7) 0.0237(7) -0.0023(6) 0.0118(6) 0.0018(6) C16 0.0293(7) 0.0283(8) 0.0262(7) 0.0013(6) 0.0097(6) 0.0047(6) C17 0.0340(8) 0.0307(8) 0.0270(7) -0.0009(6) 0.0131(6) -0.0008(6) C18 0.0262(7) 0.0449(9) 0.0246(7) -0.0016(6) 0.0110(6) 0.0007(7) C19 0.0306(8) 0.0403(9) 0.0273(7) 0.0046(6) 0.0118(6) 0.0096(7) C20 0.0337(8) 0.0299(8) 0.0302(7) 0.0044(6) 0.0155(6) 0.0054(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 N3 1.2241(19) . ? O2 N3 1.2109(18) . ? N1 C1 1.4693(19) . ? N1 C5 1.4670(18) . ? N1 C7 1.4754(19) . ? N2 C2 1.4664(19) . ? N2 C3 1.4676(18) . ? N2 C14 1.470(2) . ? N3 C4 1.5373(18) . ? C1 C2 1.520(2) . ? C1 H1A 1.010(19) . ? C1 H1B 1.00(2) . ? C2 H2A 1.018(19) . ? C2 H2B 1.003(19) . ? C3 C4 1.519(2) . ? C3 H3A 0.970(19) . ? C3 H3B 0.986(18) . ? C4 C5 1.535(2) . ? C4 C6 1.5238(19) . ? C5 H5A 0.987(18) . ? C5 H5B 0.970(18) . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 C8 1.507(2) . ? C7 H7A 0.998(18) . ? C7 H7B 1.01(2) . ? C8 C9 1.393(2) . ? C8 C13 1.390(2) . ? C9 C10 1.391(2) . ? C9 H9 0.97(2) . ? C10 C11 1.391(3) . ? C10 H10 0.98(2) . ? C11 C12 1.375(3) . ? C11 H11 0.96(2) . ? C12 C13 1.391(3) . ? C12 H12 0.96(3) . ? C13 H13 0.98(2) . ? C14 C15 1.507(2) . ? C14 H14A 0.985(18) . ? C14 H14B 1.025(19) . ? C15 C16 1.397(2) . ? C15 C20 1.393(2) . ? C16 C17 1.390(2) . ? C16 H16 0.995(19) . ? C17 C18 1.391(2) . ? C17 H17 0.98(2) . ? C18 C19 1.383(2) . ? C18 H18 0.996(19) . ? C19 C20 1.395(2) . ? C19 H19 0.96(2) . ? C20 H20 0.98(2) . ? 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 C1 N1 C7 110.25(12) . . ? C5 N1 C1 110.40(12) . . ? C5 N1 C7 110.23(12) . . ? C2 N2 C3 110.54(12) . . ? C2 N2 C14 110.31(12) . . ? C3 N2 C14 111.37(12) . . ? O1 N3 C4 117.12(12) . . ? O2 N3 O1 123.03(14) . . ? O2 N3 C4 119.73(14) . . ? N1 C1 C2 113.98(13) . . ? N1 C1 H1A 107.4(11) . . ? N1 C1 H1B 108.2(11) . . ? C2 C1 H1A 108.0(11) . . ? C2 C1 H1B 109.8(11) . . ? H1A C1 H1B 109.4(15) . . ? N2 C2 C1 114.52(13) . . ? N2 C2 H2A 110.4(10) . . ? N2 C2 H2B 108.7(11) . . ? C1 C2 H2A 108.2(10) . . ? C1 C2 H2B 107.1(11) . . ? H2A C2 H2B 107.7(15) . . ? N2 C3 C4 112.68(12) . . ? N2 C3 H3A 110.2(11) . . ? N2 C3 H3B 111.9(10) . . ? C4 C3 H3A 108.9(11) . . ? C4 C3 H3B 105.7(10) . . ? H3A C3 H3B 107.1(15) . . ? C3 C4 N3 109.35(12) . . ? C3 C4 C5 113.28(12) . . ? C3 C4 C6 110.75(13) . . ? C5 C4 N3 106.09(11) . . ? C6 C4 N3 105.06(11) . . ? C6 C4 C5 111.84(12) . . ? N1 C5 C4 111.25(12) . . ? N1 C5 H5A 110.3(10) . . ? N1 C5 H5B 111.8(10) . . ? C4 C5 H5A 108.8(10) . . ? C4 C5 H5B 108.6(11) . . ? H5A C5 H5B 106.0(15) . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? H6A C6 H6B 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N1 C7 C8 111.81(12) . . ? N1 C7 H7A 106.6(10) . . ? N1 C7 H7B 112.1(11) . . ? C8 C7 H7A 111.1(10) . . ? C8 C7 H7B 111.0(11) . . ? H7A C7 H7B 103.8(14) . . ? C9 C8 C7 120.31(14) . . ? C13 C8 C7 121.27(15) . . ? C13 C8 C9 118.40(15) . . ? C8 C9 H9 118.7(12) . . ? C10 C9 C8 120.97(16) . . ? C10 C9 H9 120.3(12) . . ? C9 C10 C11 119.60(17) . . ? C9 C10 H10 118.1(13) . . ? C11 C10 H10 122.3(13) . . ? C10 C11 H11 120.0(14) . . ? C12 C11 C10 119.98(17) . . ? C12 C11 H11 120.0(13) . . ? C11 C12 C13 120.21(17) . . ? C11 C12 H12 120.7(15) . . ? C13 C12 H12 119.1(15) . . ? C8 C13 C12 120.81(17) . . ? C8 C13 H13 119.2(12) . . ? C12 C13 H13 120.0(11) . . ? N2 C14 C15 112.33(12) . . ? N2 C14 H14A 107.2(10) . . ? N2 C14 H14B 109.0(10) . . ? C15 C14 H14A 109.1(10) . . ? C15 C14 H14B 110.5(10) . . ? H14A C14 H14B 108.5(15) . . ? C16 C15 C14 120.21(14) . . ? C20 C15 C14 121.11(14) . . ? C20 C15 C16 118.63(14) . . ? C15 C16 H16 119.7(11) . . ? C17 C16 C15 120.57(14) . . ? C17 C16 H16 119.7(11) . . ? C16 C17 C18 120.14(15) . . ? C16 C17 H17 117.0(11) . . ? C18 C17 H17 122.8(11) . . ? C17 C18 H18 120.8(11) . . ? C19 C18 C17 119.86(15) . . ? C19 C18 H18 119.3(11) . . ? C18 C19 C20 119.91(15) . . ? C18 C19 H19 121.6(12) . . ? C20 C19 H19 118.4(12) . . ? C15 C20 C19 120.86(15) . . ? C15 C20 H20 119.6(11) . . ? C19 C20 H20 119.6(11) . . ? data_[ESI_7]_11srv256 _database_code_depnum_ccdc_archive 'CCDC 906040' #TrackingRef 'web_deposit_cif_file_4_DmitryYufit_1350321914.ESI_7.cif' _audit_creation_date 2011-12-15 _audit_creation_method ; Olex2 1.1-beta (compiled 2011.11.01 svn.r2039, GUI svn.r3906) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C29 H35 N3 O6' _chemical_formula_sum 'C29 H35 N3 O6' _chemical_formula_weight 521.60 _chemical_melting_point ? _chemical_oxdiff_formula 'C29 H35 N3 O6' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/n 1' _space_group_name_Hall '-P 2yn' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.8932(2) _cell_length_b 19.1927(5) _cell_length_c 15.3402(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.411(2) _cell_angle_gamma 90.00 _cell_volume 2616.02(11) _cell_formula_units_Z 4 _cell_measurement_reflns_used 6396 _cell_measurement_temperature 120 _cell_measurement_theta_max 33.3699 _cell_measurement_theta_min 2.5956 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.89075 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.324 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 1112 _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.13 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0449 _diffrn_reflns_av_unetI/netI 0.0417 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 28554 _diffrn_reflns_theta_full 29.50 _diffrn_reflns_theta_max 29.50 _diffrn_reflns_theta_min 2.60 _diffrn_ambient_temperature 120 _diffrn_detector_area_resol_mean 16.1511 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -70.00 32.00 0.5000 20.0000 omega____ theta____ kappa____ phi______ frames - -28.3337 19.0000 30.0000 204 #__ type_ start__ end____ width___ exp.time_ 2 omega -104.00 -51.00 0.5000 20.0000 omega____ theta____ kappa____ phi______ frames - -28.3337 -179.0000 90.0000 106 #__ type_ start__ end____ width___ exp.time_ 3 omega 33.00 79.00 0.5000 20.0000 omega____ theta____ kappa____ phi______ frames - 28.9587 -127.0000 70.0000 92 #__ type_ start__ end____ width___ exp.time_ 4 omega 74.00 100.00 0.5000 20.0000 omega____ theta____ kappa____ phi______ frames - 28.9587 -146.0000 -96.0000 52 #__ type_ start__ end____ width___ exp.time_ 5 omega -41.00 14.00 0.5000 20.0000 omega____ theta____ kappa____ phi______ frames - 28.9587 -38.0000 60.0000 110 #__ type_ start__ end____ width___ exp.time_ 6 omega -97.00 -7.00 0.5000 20.0000 omega____ theta____ kappa____ phi______ frames - -28.3337 -57.0000 -150.0000 180 #__ type_ start__ end____ width___ exp.time_ 7 omega -98.00 -73.00 0.5000 20.0000 omega____ theta____ kappa____ phi______ frames - -28.3337 -77.0000 90.0000 50 #__ type_ start__ end____ width___ exp.time_ 8 omega -98.00 2.00 0.5000 20.0000 omega____ theta____ kappa____ phi______ frames - -28.3337 -77.0000 0.0000 200 ; _diffrn_measurement_device_type 'Xcalibur, Sapphire3, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0347459000 _diffrn_orient_matrix_UB_12 0.0116571000 _diffrn_orient_matrix_UB_13 0.0398369000 _diffrn_orient_matrix_UB_21 -0.0164837000 _diffrn_orient_matrix_UB_22 0.0349846000 _diffrn_orient_matrix_UB_23 -0.0118482000 _diffrn_orient_matrix_UB_31 -0.0699582000 _diffrn_orient_matrix_UB_32 -0.0024582000 _diffrn_orient_matrix_UB_33 0.0203498000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_source_current n/a _diffrn_source_voltage n/a _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 5605 _reflns_number_total 7279 _reflns_odcompleteness_completeness 99.92 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 31.44 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; XS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.331 _refine_diff_density_min -0.228 _refine_diff_density_rms 0.049 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 483 _refine_ls_number_reflns 7279 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0663 _refine_ls_R_factor_gt 0.0478 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0500P)^2^+0.7500P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1084 _refine_ls_wR_factor_ref 0.1184 _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. ; _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O -0.05947(11) 0.61761(5) 0.53340(7) 0.0238(2) Uani 1 1 d . . . O2 O 0.24345(11) 0.44626(5) 0.68062(6) 0.0224(2) Uani 1 1 d . . . O3 O 0.20162(12) 0.55719(6) -0.06435(6) 0.0247(2) Uani 1 1 d . . . O4 O 0.72968(12) 0.62329(6) -0.02479(7) 0.0273(2) Uani 1 1 d . . . O5 O 0.06091(13) 0.85470(5) 0.22741(7) 0.0304(3) Uani 1 1 d . . . O6 O 0.02617(13) 0.78915(6) 0.11390(7) 0.0304(3) Uani 1 1 d . . . N1 N 0.12903(12) 0.66907(6) 0.36744(7) 0.0165(2) Uani 1 1 d . . . N2 N 0.11858(12) 0.64745(6) 0.17535(7) 0.0172(2) Uani 1 1 d . . . N3 N 0.02619(13) 0.79890(6) 0.19278(7) 0.0203(2) Uani 1 1 d . . . C1 C 0.23572(16) 0.62455(7) 0.32253(9) 0.0194(3) Uani 1 1 d . . . C2 C 0.17559(16) 0.59414(7) 0.23646(9) 0.0191(3) Uani 1 1 d . . . C3 C -0.02976(15) 0.67186(7) 0.19956(9) 0.0182(3) Uani 1 1 d . . . C4 C -0.01807(15) 0.73885(7) 0.25311(8) 0.0166(2) Uani 1 1 d . . . C5 C 0.11269(15) 0.73690(7) 0.32353(9) 0.0178(3) Uani 1 1 d . . . C6 C 0.18474(17) 0.68211(7) 0.45871(8) 0.0195(3) Uani 1 1 d . . . C7 C 0.20147(15) 0.61752(7) 0.51425(8) 0.0176(3) Uani 1 1 d . . . C8 C 0.07610(15) 0.58660(7) 0.55245(8) 0.0181(3) Uani 1 1 d . . . C9 C 0.09427(15) 0.52906(7) 0.60689(8) 0.0186(3) Uani 1 1 d . . . C10 C 0.23855(15) 0.50216(7) 0.62522(8) 0.0182(3) Uani 1 1 d . . . C11 C 0.36345(16) 0.53165(7) 0.58867(9) 0.0199(3) Uani 1 1 d . . . C12 C 0.34163(15) 0.58891(7) 0.53373(9) 0.0191(3) Uani 1 1 d . . . C13 C -0.18786(17) 0.59002(9) 0.57423(10) 0.0266(3) Uani 1 1 d . . . C14 C 0.38773(18) 0.41606(9) 0.69915(10) 0.0264(3) Uani 1 1 d . . . C15 C 0.12464(15) 0.62506(7) 0.08417(8) 0.0187(3) Uani 1 1 d . . . C16 C 0.28487(15) 0.62574(7) 0.05370(8) 0.0179(3) Uani 1 1 d . . . C17 C 0.32076(15) 0.58970(7) -0.02202(8) 0.0189(3) Uani 1 1 d . . . C18 C 0.46783(16) 0.58749(7) -0.05096(9) 0.0211(3) Uani 1 1 d . . . C19 C 0.58095(16) 0.62289(7) -0.00328(9) 0.0212(3) Uani 1 1 d . . . C20 C 0.54718(16) 0.66111(8) 0.07027(9) 0.0222(3) Uani 1 1 d . . . C21 C 0.40060(16) 0.66204(7) 0.09761(9) 0.0204(3) Uani 1 1 d . . . C22 C 0.2296(2) 0.52022(9) -0.14274(10) 0.0287(3) Uani 1 1 d . . . C23 C 0.77405(19) 0.57628(9) -0.09119(11) 0.0289(3) Uani 1 1 d . . . C24 C -0.17001(15) 0.75721(7) 0.28897(8) 0.0173(3) Uani 1 1 d . . . C25 C -0.20520(16) 0.73425(8) 0.37187(9) 0.0213(3) Uani 1 1 d . . . C26 C -0.34606(17) 0.74831(8) 0.40416(10) 0.0239(3) Uani 1 1 d . . . C27 C -0.45273(17) 0.78467(8) 0.35437(10) 0.0251(3) Uani 1 1 d . . . C28 C -0.41910(18) 0.80686(8) 0.27134(11) 0.0286(3) Uani 1 1 d . . . C29 C -0.27862(16) 0.79335(8) 0.23847(10) 0.0241(3) Uani 1 1 d . . . H1A H 0.2657(17) 0.5857(8) 0.3620(10) 0.019(4) Uiso 1 1 d . . . H1B H 0.3316(19) 0.6513(9) 0.3115(11) 0.027(4) Uiso 1 1 d . . . H2A H 0.0977(18) 0.5568(8) 0.2473(10) 0.020(4) Uiso 1 1 d . . . H2B H 0.2609(18) 0.5700(8) 0.2104(11) 0.021(4) Uiso 1 1 d . . . H3A H -0.0826(18) 0.6378(8) 0.2366(10) 0.019(4) Uiso 1 1 d . . . H3B H -0.0975(19) 0.6811(8) 0.1469(11) 0.024(4) Uiso 1 1 d . . . H5A H 0.0930(18) 0.7715(8) 0.3653(11) 0.018(4) Uiso 1 1 d . . . H5B H 0.2078(19) 0.7499(8) 0.2946(11) 0.023(4) Uiso 1 1 d . . . H6A H 0.2855(19) 0.7055(8) 0.4592(11) 0.022(4) Uiso 1 1 d . . . H6B H 0.1122(18) 0.7133(8) 0.4851(10) 0.018(4) Uiso 1 1 d . . . H9 H 0.0101(19) 0.5072(9) 0.6318(11) 0.023(4) Uiso 1 1 d . . . H11 H 0.463(2) 0.5141(9) 0.6022(11) 0.025(4) Uiso 1 1 d . . . H12 H 0.425(2) 0.6080(9) 0.5096(12) 0.029(5) Uiso 1 1 d . . . H13A H -0.207(2) 0.5415(9) 0.5580(12) 0.028(4) Uiso 1 1 d . . . H13B H -0.176(2) 0.5917(9) 0.6378(13) 0.032(5) Uiso 1 1 d . . . H13C H -0.268(2) 0.6201(10) 0.5536(12) 0.037(5) Uiso 1 1 d . . . H14A H 0.454(2) 0.4498(10) 0.7277(12) 0.030(5) Uiso 1 1 d . . . H14B H 0.369(2) 0.3764(9) 0.7398(12) 0.031(5) Uiso 1 1 d . . . H14C H 0.435(2) 0.3997(9) 0.6425(12) 0.032(5) Uiso 1 1 d . . . H15A H 0.0608(18) 0.6588(8) 0.0481(10) 0.020(4) Uiso 1 1 d . . . H15B H 0.0822(17) 0.5767(8) 0.0745(10) 0.015(4) Uiso 1 1 d . . . H18 H 0.490(2) 0.5612(10) -0.1054(12) 0.034(5) Uiso 1 1 d . . . H20 H 0.627(2) 0.6854(9) 0.1022(11) 0.026(4) Uiso 1 1 d . . . H21 H 0.378(2) 0.6890(9) 0.1479(12) 0.029(5) Uiso 1 1 d . . . H22A H 0.135(2) 0.5009(11) -0.1630(13) 0.043(5) Uiso 1 1 d . . . H22B H 0.273(2) 0.5527(9) -0.1851(12) 0.029(4) Uiso 1 1 d . . . H22C H 0.302(2) 0.4809(10) -0.1312(12) 0.035(5) Uiso 1 1 d . . . H23A H 0.7398(19) 0.5292(9) -0.0779(11) 0.027(4) Uiso 1 1 d . . . H23B H 0.885(2) 0.5776(9) -0.0889(12) 0.032(5) Uiso 1 1 d . . . H23C H 0.733(2) 0.5908(9) -0.1481(13) 0.033(5) Uiso 1 1 d . . . H25 H -0.133(2) 0.7075(9) 0.4065(12) 0.031(5) Uiso 1 1 d . . . H26 H -0.368(2) 0.7326(10) 0.4624(13) 0.034(5) Uiso 1 1 d . . . H27 H -0.549(2) 0.7944(9) 0.3774(12) 0.032(5) Uiso 1 1 d . . . H28 H -0.495(2) 0.8303(10) 0.2352(13) 0.040(5) Uiso 1 1 d . . . H29 H -0.254(2) 0.8115(9) 0.1804(13) 0.035(5) 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 O1 0.0172(5) 0.0308(5) 0.0236(5) 0.0048(4) 0.0019(4) 0.0053(4) O2 0.0208(5) 0.0266(5) 0.0199(5) 0.0068(4) 0.0005(4) 0.0029(4) O3 0.0242(5) 0.0320(5) 0.0179(5) -0.0077(4) 0.0027(4) -0.0031(4) O4 0.0201(5) 0.0307(6) 0.0316(6) -0.0014(5) 0.0086(4) 0.0002(4) O5 0.0374(6) 0.0240(5) 0.0297(6) 0.0050(4) -0.0009(5) -0.0072(5) O6 0.0397(6) 0.0343(6) 0.0178(5) 0.0067(4) 0.0081(4) 0.0078(5) N1 0.0183(5) 0.0194(5) 0.0118(5) 0.0007(4) 0.0001(4) 0.0028(4) N2 0.0170(5) 0.0231(6) 0.0114(5) 0.0000(4) 0.0017(4) 0.0035(4) N3 0.0174(6) 0.0252(6) 0.0185(5) 0.0051(5) 0.0034(4) 0.0025(5) C1 0.0197(7) 0.0232(7) 0.0153(6) 0.0021(5) 0.0014(5) 0.0037(5) C2 0.0221(7) 0.0211(6) 0.0142(6) 0.0004(5) 0.0023(5) 0.0036(5) C3 0.0162(6) 0.0229(6) 0.0156(6) -0.0020(5) 0.0011(5) 0.0015(5) C4 0.0167(6) 0.0194(6) 0.0137(6) 0.0033(5) 0.0028(5) 0.0012(5) C5 0.0180(6) 0.0189(6) 0.0167(6) 0.0009(5) 0.0011(5) -0.0004(5) C6 0.0229(7) 0.0215(6) 0.0139(6) -0.0004(5) -0.0008(5) -0.0019(5) C7 0.0209(7) 0.0209(6) 0.0109(5) -0.0012(5) -0.0014(5) -0.0004(5) C8 0.0171(6) 0.0231(6) 0.0139(6) -0.0027(5) -0.0006(5) 0.0026(5) C9 0.0171(6) 0.0244(7) 0.0144(6) 0.0002(5) 0.0018(5) -0.0007(5) C10 0.0201(7) 0.0226(6) 0.0118(5) -0.0007(5) -0.0006(5) 0.0009(5) C11 0.0161(6) 0.0271(7) 0.0163(6) -0.0012(5) -0.0006(5) 0.0006(5) C12 0.0168(6) 0.0251(7) 0.0155(6) -0.0017(5) 0.0007(5) -0.0036(5) C13 0.0183(7) 0.0365(8) 0.0251(7) 0.0008(6) 0.0027(6) 0.0036(6) C14 0.0234(7) 0.0299(8) 0.0257(7) 0.0048(6) -0.0026(6) 0.0059(6) C15 0.0190(6) 0.0242(7) 0.0131(6) -0.0014(5) 0.0016(5) 0.0011(5) C16 0.0192(6) 0.0205(6) 0.0143(6) 0.0017(5) 0.0031(5) 0.0014(5) C17 0.0212(7) 0.0201(6) 0.0155(6) 0.0013(5) 0.0018(5) 0.0007(5) C18 0.0239(7) 0.0223(6) 0.0176(6) 0.0002(5) 0.0068(5) 0.0017(5) C19 0.0185(7) 0.0221(6) 0.0233(7) 0.0066(5) 0.0053(5) 0.0023(5) C20 0.0208(7) 0.0257(7) 0.0200(6) 0.0015(5) 0.0003(5) -0.0014(6) C21 0.0228(7) 0.0238(7) 0.0146(6) -0.0008(5) 0.0022(5) 0.0006(5) C22 0.0321(9) 0.0344(8) 0.0199(7) -0.0100(6) 0.0044(6) -0.0028(7) C23 0.0266(8) 0.0280(8) 0.0331(8) 0.0025(6) 0.0130(7) 0.0036(6) C24 0.0176(6) 0.0183(6) 0.0161(6) -0.0023(5) 0.0022(5) -0.0001(5) C25 0.0206(7) 0.0258(7) 0.0179(6) 0.0017(5) 0.0035(5) 0.0023(6) C26 0.0251(7) 0.0275(7) 0.0198(7) -0.0023(5) 0.0080(6) -0.0005(6) C27 0.0193(7) 0.0259(7) 0.0305(8) -0.0041(6) 0.0064(6) 0.0021(6) C28 0.0208(7) 0.0332(8) 0.0319(8) 0.0052(6) 0.0012(6) 0.0065(6) C29 0.0212(7) 0.0297(7) 0.0217(7) 0.0050(6) 0.0023(5) 0.0026(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C8 1.3651(16) . ? O1 C13 1.4269(18) . ? O2 C10 1.3682(16) . ? O2 C14 1.4256(18) . ? O3 C17 1.3696(17) . ? O3 C22 1.4270(17) . ? O4 C19 1.3767(17) . ? O4 C23 1.4286(18) . ? O5 N3 1.2290(16) . ? O6 N3 1.2245(15) . ? N1 C1 1.4698(17) . ? N1 C5 1.4701(17) . ? N1 C6 1.4867(17) . ? N2 C2 1.4638(17) . ? N2 C3 1.4625(17) . ? N2 C15 1.4664(16) . ? N3 C4 1.5396(17) . ? C1 C2 1.5199(19) . ? C1 H1A 0.990(16) . ? C1 H1B 1.015(17) . ? C2 H2A 1.015(16) . ? C2 H2B 0.988(16) . ? C3 C4 1.5269(19) . ? C3 H3A 0.997(16) . ? C3 H3B 1.004(17) . ? C4 C5 1.5540(19) . ? C4 C24 1.5215(18) . ? C5 H5A 0.945(16) . ? C5 H5B 1.004(17) . ? C6 C7 1.5080(19) . ? C6 H6A 1.002(17) . ? C6 H6B 0.981(16) . ? C7 C8 1.4121(19) . ? C7 C12 1.3832(19) . ? C8 C9 1.3899(19) . ? C9 C10 1.4006(19) . ? C9 H9 0.952(17) . ? C10 C11 1.3861(19) . ? C11 C12 1.3934(19) . ? C11 H11 0.963(17) . ? C12 H12 0.918(18) . ? C13 H13A 0.977(18) . ? C13 H13B 0.977(19) . ? C13 H13C 0.96(2) . ? C14 H14A 0.966(19) . ? C14 H14B 1.002(18) . ? C14 H14C 1.029(19) . ? C15 C16 1.5183(19) . ? C15 H15A 1.011(16) . ? C15 H15B 1.011(15) . ? C16 C17 1.4002(18) . ? C16 C21 1.393(2) . ? C17 C18 1.3995(19) . ? C18 C19 1.395(2) . ? C18 H18 1.002(19) . ? C19 C20 1.389(2) . ? C20 C21 1.3862(19) . ? C20 H20 0.969(18) . ? C21 H21 0.957(18) . ? C22 H22A 0.96(2) . ? C22 H22B 0.990(18) . ? C22 H22C 1.005(19) . ? C23 H23A 0.979(18) . ? C23 H23B 0.984(19) . ? C23 H23C 0.973(19) . ? C24 C25 1.3938(18) . ? C24 C29 1.397(2) . ? C25 C26 1.393(2) . ? C25 H25 0.965(19) . ? C26 C27 1.382(2) . ? C26 H26 0.972(19) . ? C27 C28 1.387(2) . ? C27 H27 0.959(18) . ? C28 C29 1.391(2) . ? C28 H28 0.97(2) . ? C29 H29 0.988(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 C8 O1 C13 117.39(11) . . ? C10 O2 C14 116.58(11) . . ? C17 O3 C22 117.86(11) . . ? C19 O4 C23 117.67(12) . . ? C1 N1 C5 110.69(10) . . ? C1 N1 C6 110.07(10) . . ? C5 N1 C6 107.76(10) . . ? C2 N2 C15 112.36(11) . . ? C3 N2 C2 110.68(10) . . ? C3 N2 C15 113.95(10) . . ? O5 N3 C4 117.28(11) . . ? O6 N3 O5 123.37(12) . . ? O6 N3 C4 119.35(11) . . ? N1 C1 C2 114.83(11) . . ? N1 C1 H1A 108.3(9) . . ? N1 C1 H1B 110.3(10) . . ? C2 C1 H1A 108.5(9) . . ? C2 C1 H1B 108.5(10) . . ? H1A C1 H1B 106.1(13) . . ? N2 C2 C1 112.81(11) . . ? N2 C2 H2A 112.2(9) . . ? N2 C2 H2B 108.7(10) . . ? C1 C2 H2A 110.2(9) . . ? C1 C2 H2B 106.5(10) . . ? H2A C2 H2B 106.1(13) . . ? N2 C3 C4 111.39(11) . . ? N2 C3 H3A 112.7(9) . . ? N2 C3 H3B 111.7(10) . . ? C4 C3 H3A 105.6(9) . . ? C4 C3 H3B 108.1(9) . . ? H3A C3 H3B 107.1(13) . . ? N3 C4 C5 103.48(10) . . ? C3 C4 N3 108.68(10) . . ? C3 C4 C5 112.68(11) . . ? C24 C4 N3 107.30(10) . . ? C24 C4 C3 110.37(11) . . ? C24 C4 C5 113.84(11) . . ? N1 C5 C4 113.36(11) . . ? N1 C5 H5A 109.2(10) . . ? N1 C5 H5B 110.7(10) . . ? C4 C5 H5A 107.5(10) . . ? C4 C5 H5B 107.8(10) . . ? H5A C5 H5B 108.0(13) . . ? N1 C6 C7 114.50(11) . . ? N1 C6 H6A 110.1(9) . . ? N1 C6 H6B 107.0(9) . . ? C7 C6 H6A 107.3(9) . . ? C7 C6 H6B 108.7(9) . . ? H6A C6 H6B 109.1(13) . . ? C8 C7 C6 121.27(12) . . ? C12 C7 C6 121.00(12) . . ? C12 C7 C8 117.61(12) . . ? O1 C8 C7 115.70(12) . . ? O1 C8 C9 123.67(12) . . ? C9 C8 C7 120.63(12) . . ? C8 C9 C10 119.73(12) . . ? C8 C9 H9 121.2(10) . . ? C10 C9 H9 119.1(10) . . ? O2 C10 C9 114.76(12) . . ? O2 C10 C11 124.50(12) . . ? C11 C10 C9 120.74(13) . . ? C10 C11 C12 118.25(13) . . ? C10 C11 H11 121.1(10) . . ? C12 C11 H11 120.6(10) . . ? C7 C12 C11 123.03(13) . . ? C7 C12 H12 119.3(11) . . ? C11 C12 H12 117.6(11) . . ? O1 C13 H13A 112.1(10) . . ? O1 C13 H13B 112.0(11) . . ? O1 C13 H13C 103.3(11) . . ? H13A C13 H13B 107.2(15) . . ? H13A C13 H13C 111.6(15) . . ? H13B C13 H13C 110.6(15) . . ? O2 C14 H14A 110.0(11) . . ? O2 C14 H14B 105.3(10) . . ? O2 C14 H14C 110.5(10) . . ? H14A C14 H14B 109.8(15) . . ? H14A C14 H14C 109.1(14) . . ? H14B C14 H14C 112.2(14) . . ? N2 C15 C16 111.33(11) . . ? N2 C15 H15A 106.9(9) . . ? N2 C15 H15B 112.4(9) . . ? C16 C15 H15A 109.8(9) . . ? C16 C15 H15B 108.2(8) . . ? H15A C15 H15B 108.1(13) . . ? C17 C16 C15 120.05(12) . . ? C21 C16 C15 122.64(12) . . ? C21 C16 C17 117.30(12) . . ? O3 C17 C16 114.81(12) . . ? O3 C17 C18 123.40(12) . . ? C18 C17 C16 121.79(13) . . ? C17 C18 H18 119.9(10) . . ? C19 C18 C17 118.81(12) . . ? C19 C18 H18 121.3(10) . . ? O4 C19 C18 123.78(13) . . ? O4 C19 C20 115.75(13) . . ? C20 C19 C18 120.47(13) . . ? C19 C20 H20 119.0(10) . . ? C21 C20 C19 119.39(13) . . ? C21 C20 H20 121.5(10) . . ? C16 C21 H21 118.9(11) . . ? C20 C21 C16 122.16(13) . . ? C20 C21 H21 119.0(11) . . ? O3 C22 H22A 106.4(12) . . ? O3 C22 H22B 109.1(10) . . ? O3 C22 H22C 111.0(11) . . ? H22A C22 H22B 113.0(16) . . ? H22A C22 H22C 108.5(16) . . ? H22B C22 H22C 108.9(14) . . ? O4 C23 H23A 109.7(10) . . ? O4 C23 H23B 105.3(11) . . ? O4 C23 H23C 110.7(11) . . ? H23A C23 H23B 109.7(15) . . ? H23A C23 H23C 110.0(15) . . ? H23B C23 H23C 111.4(15) . . ? C25 C24 C4 119.58(12) . . ? C25 C24 C29 119.11(12) . . ? C29 C24 C4 121.22(12) . . ? C24 C25 H25 120.0(11) . . ? C26 C25 C24 120.20(13) . . ? C26 C25 H25 119.8(11) . . ? C25 C26 H26 119.3(11) . . ? C27 C26 C25 120.55(13) . . ? C27 C26 H26 120.2(11) . . ? C26 C27 C28 119.53(14) . . ? C26 C27 H27 119.9(11) . . ? C28 C27 H27 120.6(11) . . ? C27 C28 C29 120.47(14) . . ? C27 C28 H28 119.8(12) . . ? C29 C28 H28 119.7(12) . . ? C24 C29 H29 120.0(11) . . ? C28 C29 C24 120.13(13) . . ? C28 C29 H29 119.8(11) . . ?