# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_0904083 _database_code_depnum_ccdc_archive 'CCDC 898254' #TrackingRef 'web_deposit_cif_file_0_ChaoGao_1345862204.0904083.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H16 N7 O, F6 P, C H4 O' _chemical_formula_sum 'C22 H20 F6 N7 O2 P' _chemical_formula_weight 559.42 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P n m a' _symmetry_int_tables_number 62 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z' '-x-1/2, y-1/2, z-1/2' _cell_length_a 18.2455(3) _cell_length_b 15.6917(2) _cell_length_c 8.02860(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2298.61(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 10404 _cell_measurement_theta_min 2.5330 _cell_measurement_theta_max 29.2301 _exptl_crystal_description parallelepiped _exptl_crystal_colour colorless _exptl_crystal_size_max 0.58 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.617 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1144 _exptl_absorpt_coefficient_mu 0.207 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.96937 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) (compiled Feb 27 2009,15:38:38) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18885 _diffrn_reflns_av_R_equivalents 0.0256 _diffrn_reflns_av_sigmaI/netI 0.0230 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.58 _diffrn_reflns_theta_max 29.27 _reflns_number_total 2998 _reflns_number_gt 2426 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0500P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2998 _refine_ls_number_parameters 194 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0415 _refine_ls_R_factor_gt 0.0312 _refine_ls_wR_factor_ref 0.0882 _refine_ls_wR_factor_gt 0.0861 _refine_ls_goodness_of_fit_ref 1.170 _refine_ls_restrained_S_all 1.170 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P P 0.00340(2) 0.2500 0.31929(5) 0.01524(12) Uani 1 2 d S . . F1 F 0.04057(4) 0.17750(4) 0.20657(10) 0.02496(19) Uani 1 1 d . . . F2 F -0.06662(6) 0.2500 0.19642(14) 0.0280(3) Uani 1 2 d S . . F3 F -0.03448(4) 0.17759(5) 0.43023(10) 0.0303(2) Uani 1 1 d . . . F4 F 0.07261(6) 0.2500 0.44039(14) 0.0276(3) Uani 1 2 d S . . O1 O -0.16934(6) 0.2500 -0.21844(16) 0.0202(3) Uani 1 2 d S . . N1 N -0.06443(5) 0.17312(6) -0.18390(12) 0.0152(2) Uani 1 1 d . . . N2 N 0.04808(7) 0.2500 -0.16187(17) 0.0143(3) Uani 1 2 d S . . N3 N 0.04744(5) 0.10320(6) -0.15607(12) 0.0143(2) Uani 1 1 d . . . N4 N 0.13942(5) 0.01955(6) -0.11571(13) 0.0153(2) Uani 1 1 d . . . C1 C -0.10185(9) 0.2500 -0.1982(2) 0.0150(3) Uani 1 2 d S . . C2 C 0.00620(6) 0.18079(7) -0.16757(14) 0.0134(2) Uani 1 1 d . . . C3 C 0.11792(6) 0.10054(7) -0.11110(15) 0.0149(2) Uani 1 1 d . . . H3B H 0.1474 0.1480 -0.0812 0.018 Uiso 1 1 calc R . . C4 C 0.02343(7) 0.02127(7) -0.19020(15) 0.0175(3) Uani 1 1 d . . . H4A H -0.0245 0.0051 -0.2243 0.021 Uiso 1 1 calc R . . C5 C 0.08077(6) -0.03093(7) -0.16590(15) 0.0179(3) Uani 1 1 d . . . H5A H 0.0812 -0.0910 -0.1803 0.021 Uiso 1 1 calc R . . C6 C 0.21296(6) -0.00953(7) -0.08282(15) 0.0155(2) Uani 1 1 d . . . C7 C 0.22373(7) -0.09178(7) -0.02568(17) 0.0210(3) Uani 1 1 d . . . H7A H 0.1833 -0.1285 -0.0056 0.025 Uiso 1 1 calc R . . C8 C 0.29494(7) -0.11939(8) 0.00156(17) 0.0231(3) Uani 1 1 d . . . H8A H 0.3035 -0.1761 0.0384 0.028 Uiso 1 1 calc R . . C9 C 0.35373(6) -0.06525(8) -0.02440(16) 0.0199(3) Uani 1 1 d . . . H9A H 0.4023 -0.0849 -0.0062 0.024 Uiso 1 1 calc R . . C10 C 0.34168(6) 0.01761(8) -0.07691(16) 0.0201(3) Uani 1 1 d . . . H10A H 0.3819 0.0554 -0.0907 0.024 Uiso 1 1 calc R . . C11 C 0.27107(6) 0.04550(7) -0.10939(16) 0.0192(3) Uani 1 1 d . . . H11A H 0.2627 0.1016 -0.1493 0.023 Uiso 1 1 calc R . . O2 O -0.27348(6) 0.2500 -0.45722(16) 0.0188(3) Uani 1 2 d S . . H2A H -0.2366(13) 0.2500 -0.378(3) 0.049(7) Uiso 1 2 d S . . C12 C -0.24414(16) 0.2500 -0.6205(3) 0.0482(6) Uani 1 2 d S . . H12B H -0.2191(11) 0.1955(14) -0.646(3) 0.086(8) Uiso 1 1 d . . . H12A H -0.2835(19) 0.2500 -0.710(5) 0.108(13) Uiso 1 2 d S . . 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 P 0.0194(2) 0.0129(2) 0.0134(2) 0.000 -0.00098(17) 0.000 F1 0.0325(4) 0.0174(4) 0.0250(4) -0.0047(3) 0.0018(3) 0.0045(3) F2 0.0236(6) 0.0332(6) 0.0271(6) 0.000 -0.0082(4) 0.000 F3 0.0406(5) 0.0272(4) 0.0232(5) 0.0060(3) 0.0045(4) -0.0112(3) F4 0.0318(6) 0.0213(5) 0.0296(6) 0.000 -0.0146(5) 0.000 O1 0.0115(6) 0.0236(6) 0.0255(7) 0.000 -0.0019(5) 0.000 N1 0.0125(5) 0.0176(5) 0.0154(5) -0.0020(4) 0.0004(4) -0.0007(4) N2 0.0126(6) 0.0152(6) 0.0149(7) 0.000 0.0002(5) 0.000 N3 0.0119(5) 0.0133(5) 0.0177(5) -0.0024(4) 0.0005(4) -0.0011(4) N4 0.0143(5) 0.0114(4) 0.0201(5) -0.0018(4) 0.0021(4) -0.0003(4) C1 0.0142(8) 0.0187(8) 0.0121(8) 0.000 0.0011(6) 0.000 C2 0.0149(6) 0.0142(5) 0.0111(6) -0.0017(4) 0.0008(4) 0.0007(4) C3 0.0143(6) 0.0126(5) 0.0177(6) -0.0019(4) 0.0018(4) -0.0007(4) C4 0.0166(6) 0.0150(5) 0.0211(6) -0.0036(5) 0.0010(5) -0.0044(4) C5 0.0172(6) 0.0135(5) 0.0229(7) -0.0032(5) 0.0021(5) -0.0039(4) C6 0.0132(6) 0.0141(5) 0.0192(6) -0.0026(5) 0.0013(4) 0.0020(4) C7 0.0206(6) 0.0137(6) 0.0285(7) 0.0013(5) 0.0026(5) -0.0023(5) C8 0.0257(7) 0.0127(6) 0.0308(7) 0.0020(5) 0.0006(6) 0.0040(5) C9 0.0175(6) 0.0190(6) 0.0231(7) -0.0030(5) -0.0006(5) 0.0055(5) C10 0.0160(6) 0.0174(6) 0.0270(7) -0.0002(5) 0.0026(5) -0.0014(5) C11 0.0184(6) 0.0116(5) 0.0274(7) 0.0019(5) 0.0020(5) 0.0011(5) O2 0.0160(6) 0.0175(6) 0.0228(7) 0.000 -0.0005(5) 0.000 C12 0.0537(16) 0.0646(18) 0.0262(12) 0.000 0.0108(12) 0.000 _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 P F4 1.5937(11) . ? P F3 1.6006(8) 7_565 ? P F3 1.6006(8) . ? P F1 1.6041(8) . ? P F1 1.6041(8) 7_565 ? P F2 1.6140(11) . ? O1 C1 1.2420(19) . ? N1 C2 1.3010(14) . ? N1 C1 1.3909(12) . ? N2 C2 1.3286(13) . ? N2 C2 1.3286(13) 7_565 ? N3 C3 1.3363(14) . ? N3 C4 1.3855(14) . ? N3 C2 1.4342(13) . ? N4 C3 1.3306(14) . ? N4 C5 1.3909(14) . ? N4 C6 1.4417(14) . ? C1 N1 1.3909(12) 7_565 ? C3 H3B 0.9500 . ? C4 C5 1.3431(17) . ? C4 H4A 0.9500 . ? C5 H5A 0.9500 . ? C6 C7 1.3838(16) . ? C6 C11 1.3839(16) . ? C7 C8 1.3868(17) . ? C7 H7A 0.9500 . ? C8 C9 1.3841(17) . ? C8 H8A 0.9500 . ? C9 C10 1.3843(17) . ? C9 H9A 0.9500 . ? C10 C11 1.3854(16) . ? C10 H10A 0.9500 . ? C11 H11A 0.9500 . ? O2 C12 1.416(3) . ? O2 H2A 0.92(2) . ? C12 H12B 0.99(2) . ? C12 H12A 1.02(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag F4 P F3 90.15(5) . 7_565 ? F4 P F3 90.15(5) . . ? F3 P F3 90.45(6) 7_565 . ? F4 P F1 90.53(5) . . ? F3 P F1 179.32(5) 7_565 . ? F3 P F1 89.60(4) . . ? F4 P F1 90.53(5) . 7_565 ? F3 P F1 89.60(4) 7_565 7_565 ? F3 P F1 179.32(5) . 7_565 ? F1 P F1 90.34(6) . 7_565 ? F4 P F2 179.91(7) . . ? F3 P F2 89.91(4) 7_565 . ? F3 P F2 89.91(4) . . ? F1 P F2 89.41(4) . . ? F1 P F2 89.41(4) 7_565 . ? C2 N1 C1 114.47(10) . . ? C2 N2 C2 109.64(13) . 7_565 ? C3 N3 C4 109.19(9) . . ? C3 N3 C2 123.27(9) . . ? C4 N3 C2 127.53(10) . . ? C3 N4 C5 108.98(10) . . ? C3 N4 C6 124.86(10) . . ? C5 N4 C6 126.07(10) . . ? O1 C1 N1 119.83(7) . 7_565 ? O1 C1 N1 119.83(7) . . ? N1 C1 N1 120.30(14) 7_565 . ? N1 C2 N2 130.45(11) . . ? N1 C2 N3 116.58(9) . . ? N2 C2 N3 112.96(10) . . ? N4 C3 N3 107.81(10) . . ? N4 C3 H3B 126.1 . . ? N3 C3 H3B 126.1 . . ? C5 C4 N3 106.91(10) . . ? C5 C4 H4A 126.5 . . ? N3 C4 H4A 126.5 . . ? C4 C5 N4 107.10(10) . . ? C4 C5 H5A 126.5 . . ? N4 C5 H5A 126.5 . . ? C7 C6 C11 121.62(11) . . ? C7 C6 N4 119.22(10) . . ? C11 C6 N4 119.16(10) . . ? C6 C7 C8 118.47(11) . . ? C6 C7 H7A 120.8 . . ? C8 C7 H7A 120.8 . . ? C9 C8 C7 120.70(11) . . ? C9 C8 H8A 119.7 . . ? C7 C8 H8A 119.7 . . ? C8 C9 C10 119.95(11) . . ? C8 C9 H9A 120.0 . . ? C10 C9 H9A 120.0 . . ? C9 C10 C11 120.11(11) . . ? C9 C10 H10A 119.9 . . ? C11 C10 H10A 119.9 . . ? C6 C11 C10 119.09(11) . . ? C6 C11 H11A 120.5 . . ? C10 C11 H11A 120.5 . . ? C12 O2 H2A 111.0(15) . . ? O2 C12 H12B 111.5(13) . . ? O2 C12 H12A 113(2) . . ? H12B C12 H12A 100.3(15) . . ? _diffrn_measured_fraction_theta_max 0.926 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.255 _refine_diff_density_min -0.369 _refine_diff_density_rms 0.048 data_120723_s1_gc _database_code_depnum_ccdc_archive 'CCDC 898255' #TrackingRef 'web_deposit_cif_file_0_ChaoGao_1345862914.120723.cif' _audit_creation_date 2012-07-24 _audit_creation_method ; Olex2 1.1 (compiled 2011.11.01 svn.r2039, GUI svn.r3906) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C10 H13 N5 O2, C3 H6 O' _chemical_formula_sum 'C13 H19 N5 O3' _chemical_formula_weight 293.33 _chemical_melting_point ? _chemical_oxdiff_formula C15H16N2O3 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 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 8.0418(5) _cell_length_b 9.8200(6) _cell_length_c 10.9614(8) _cell_angle_alpha 89.012(5) _cell_angle_beta 77.986(6) _cell_angle_gamma 65.983(6) _cell_volume 771.15(9) _cell_formula_units_Z 2 _cell_measurement_reflns_used 2058 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 29.1341 _cell_measurement_theta_min 3.0479 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.97585 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.263 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 312 _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.20 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0185 _diffrn_reflns_av_unetI/netI 0.0320 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 5798 _diffrn_reflns_theta_full 24.99 _diffrn_reflns_theta_max 24.99 _diffrn_reflns_theta_min 3.05 _diffrn_ambient_temperature 293.15 _diffrn_detector_area_resol_mean 16.0874 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -22.00 21.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - -16.8924 -99.0000 -150.0000 43 #__ type_ start__ end____ width___ exp.time_ 2 omega -71.00 -46.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - -16.8924 -178.0000 120.0000 25 #__ type_ start__ end____ width___ exp.time_ 3 omega -21.00 19.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - -16.8924 -99.0000 30.0000 40 #__ type_ start__ end____ width___ exp.time_ 4 omega -42.00 39.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - 19.8611 -57.0000 -60.0000 81 #__ type_ start__ end____ width___ exp.time_ 5 omega -2.00 79.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - 19.8611 57.0000 -180.0000 81 #__ type_ start__ end____ width___ exp.time_ 6 omega -20.00 88.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - 19.8611 19.0000 120.0000 108 #__ type_ start__ end____ width___ exp.time_ 7 omega 35.00 82.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - 19.8611 178.0000 -180.0000 47 ; _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0378710000 _diffrn_orient_matrix_UB_12 0.0146022000 _diffrn_orient_matrix_UB_13 0.0653148000 _diffrn_orient_matrix_UB_21 -0.0226223000 _diffrn_orient_matrix_UB_22 0.0772246000 _diffrn_orient_matrix_UB_23 -0.0058190000 _diffrn_orient_matrix_UB_31 -0.0886201000 _diffrn_orient_matrix_UB_32 0.0105892000 _diffrn_orient_matrix_UB_33 -0.0101039000 _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 2015 _reflns_number_total 2722 _reflns_odcompleteness_completeness 99.84 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _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 ; SHELXL, G.M. Sheldrick, Acta Cryst. 2008). A64, 112-122 ; _computing_structure_solution ; SHELXS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.609 _refine_diff_density_min -0.306 _refine_diff_density_rms 0.049 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 193 _refine_ls_number_reflns 2722 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0849 _refine_ls_R_factor_gt 0.0644 _refine_ls_restrained_S_all 1.068 _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^)+(0.1002P)^2^+0.3111P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1793 _refine_ls_wR_factor_ref 0.1972 _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 O1 O 0.8757(3) 0.1951(2) -0.0032(2) 0.0637(6) Uani 1 1 d . . . O2 O 0.6467(3) -0.13998(19) 0.1459(2) 0.0561(6) Uani 1 1 d . . . O3 O -0.0656(5) 0.1156(4) 0.3313(4) 0.1344(14) Uani 1 1 d . . . N1 N 0.7588(3) 0.0282(2) 0.0688(2) 0.0460(6) Uani 1 1 d . . . H1 H 0.8701 -0.0413 0.0537 0.055 Uiso 1 1 calc R . . N2 N 0.5613(3) 0.2787(2) 0.0598(2) 0.0438(6) Uani 1 1 d . . . N3 N 0.4381(3) 0.1014(2) 0.1411(2) 0.0417(5) Uani 1 1 d . . . N4 N 0.2454(3) 0.3469(2) 0.12615(18) 0.0371(5) Uani 1 1 d . . . N5 N -0.0543(3) 0.4576(2) 0.17898(19) 0.0405(5) Uani 1 1 d . . . C1 C 0.7380(3) 0.1696(3) 0.0395(3) 0.0454(7) Uani 1 1 d . . . C2 C 0.6144(3) -0.0105(3) 0.1204(2) 0.0424(6) Uani 1 1 d . . . C3 C 0.4320(3) 0.2313(3) 0.1069(2) 0.0374(6) Uani 1 1 d . . . C4 C 0.0899(3) 0.3275(3) 0.1715(2) 0.0416(6) Uani 1 1 d . . . H4 H 0.0840 0.2375 0.1941 0.050 Uiso 1 1 calc R . . C5 C 0.1972(3) 0.4956(3) 0.1035(2) 0.0398(6) Uani 1 1 d . . . H5 H 0.2784 0.5396 0.0717 0.048 Uiso 1 1 calc R . . C6 C 0.0108(4) 0.5638(3) 0.1362(2) 0.0428(6) Uani 1 1 d . . . H6 H -0.0618 0.6646 0.1310 0.051 Uiso 1 1 calc R . . C7 C -0.2505(4) 0.4859(3) 0.2275(3) 0.0508(7) Uani 1 1 d . . . H7A H -0.2610 0.3912 0.2378 0.061 Uiso 1 1 calc R . . H7B H -0.3227 0.5379 0.1672 0.061 Uiso 1 1 calc R . . C8 C -0.3302(4) 0.5776(4) 0.3504(3) 0.0730(10) Uani 1 1 d . . . H8A H -0.3311 0.6756 0.3360 0.088 Uiso 1 1 calc R . . H8B H -0.4593 0.5914 0.3770 0.088 Uiso 1 1 calc R . . C9 C -0.2414(6) 0.5230(7) 0.4516(4) 0.1145(18) Uani 1 1 d . . . H9A H -0.1120 0.5083 0.4256 0.137 Uiso 1 1 calc R . . H9B H -0.2423 0.4258 0.4679 0.137 Uiso 1 1 calc R . . C10 C -0.3269(8) 0.6216(7) 0.5736(4) 0.126(2) Uani 1 1 d . . . H10A H -0.3064 0.7112 0.5633 0.189 Uiso 1 1 calc R . . H10B H -0.2698 0.5687 0.6388 0.189 Uiso 1 1 calc R . . H10C H -0.4586 0.6472 0.5956 0.189 Uiso 1 1 calc R . . C11 C -0.0168(8) -0.0173(6) 0.3391(4) 0.0999(15) Uani 1 1 d . . . C12 C 0.1826(9) -0.1221(6) 0.3003(5) 0.134(2) Uani 1 1 d . . . H12A H 0.2142 -0.1461 0.2117 0.202 Uiso 1 1 calc R . . H12B H 0.2038 -0.2119 0.3429 0.202 Uiso 1 1 calc R . . H12C H 0.2589 -0.0762 0.3214 0.202 Uiso 1 1 calc R . . C13 C -0.1561(10) -0.0762(8) 0.3914(6) 0.159(3) Uani 1 1 d . . . H13A H -0.2610 0.0003 0.4458 0.239 Uiso 1 1 calc R . . H13B H -0.1012 -0.1605 0.4379 0.239 Uiso 1 1 calc R . . H13C H -0.1968 -0.1067 0.3246 0.239 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0379(11) 0.0356(11) 0.1095(18) 0.0137(10) 0.0005(11) -0.0152(8) O2 0.0484(11) 0.0327(10) 0.0842(15) 0.0193(9) -0.0118(10) -0.0157(8) O3 0.154(3) 0.086(2) 0.172(4) 0.038(2) -0.020(3) -0.066(2) N1 0.0360(12) 0.0306(11) 0.0672(15) 0.0086(10) -0.0069(10) -0.0118(9) N2 0.0382(11) 0.0291(11) 0.0613(14) 0.0059(9) -0.0044(10) -0.0142(9) N3 0.0398(12) 0.0313(11) 0.0510(13) 0.0097(9) -0.0057(10) -0.0140(9) N4 0.0361(11) 0.0301(10) 0.0418(12) 0.0044(8) -0.0031(9) -0.0131(9) N5 0.0372(11) 0.0380(11) 0.0429(12) 0.0035(9) -0.0044(9) -0.0144(9) C1 0.0395(14) 0.0309(13) 0.0626(17) 0.0048(12) -0.0041(12) -0.0148(11) C2 0.0435(14) 0.0336(13) 0.0500(15) 0.0094(11) -0.0101(12) -0.0162(11) C3 0.0396(13) 0.0298(12) 0.0400(13) 0.0022(10) -0.0067(11) -0.0125(10) C4 0.0443(14) 0.0341(13) 0.0466(15) 0.0051(11) -0.0071(12) -0.0179(11) C5 0.0431(14) 0.0302(12) 0.0436(14) 0.0056(10) -0.0037(11) -0.0155(11) C6 0.0445(14) 0.0338(13) 0.0444(15) 0.0056(11) -0.0042(11) -0.0133(11) C7 0.0357(14) 0.0577(17) 0.0554(17) 0.0035(13) -0.0047(12) -0.0185(12) C8 0.0515(18) 0.094(3) 0.066(2) -0.0050(18) 0.0080(16) -0.0321(17) C9 0.083(3) 0.194(5) 0.064(3) -0.010(3) -0.002(2) -0.061(3) C10 0.149(4) 0.194(6) 0.059(2) -0.029(3) 0.014(3) -0.110(4) C11 0.154(5) 0.102(3) 0.080(3) 0.030(3) -0.043(3) -0.082(4) C12 0.163(6) 0.107(4) 0.118(4) 0.013(3) -0.011(4) -0.051(4) C13 0.246(8) 0.191(6) 0.148(5) 0.069(5) -0.088(5) -0.178(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 C1 1.230(3) . ? O2 C2 1.229(3) . ? O3 C11 1.207(5) . ? N1 H1 0.8600 . ? N1 C1 1.369(3) . ? N1 C2 1.375(3) . ? N2 C1 1.362(3) . ? N2 C3 1.314(3) . ? N3 C2 1.370(3) . ? N3 C3 1.308(3) . ? N4 C3 1.440(3) . ? N4 C4 1.334(3) . ? N4 C5 1.383(3) . ? N5 C4 1.320(3) . ? N5 C6 1.382(3) . ? N5 C7 1.466(3) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C5 C6 1.338(3) . ? C6 H6 0.9300 . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C7 C8 1.499(4) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C8 C9 1.424(5) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C9 C10 1.523(6) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C12 1.483(7) . ? C11 C13 1.472(7) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 H1 117.6 . . ? C1 N1 C2 124.7(2) . . ? C2 N1 H1 117.6 . . ? C3 N2 C1 113.6(2) . . ? C3 N3 C2 114.2(2) . . ? C4 N4 C3 125.0(2) . . ? C4 N4 C5 108.7(2) . . ? C5 N4 C3 126.2(2) . . ? C4 N5 C6 108.6(2) . . ? C4 N5 C7 125.9(2) . . ? C6 N5 C7 125.5(2) . . ? O1 C1 N1 120.3(2) . . ? O1 C1 N2 122.0(2) . . ? N2 C1 N1 117.6(2) . . ? O2 C2 N1 120.2(2) . . ? O2 C2 N3 123.2(2) . . ? N3 C2 N1 116.6(2) . . ? N2 C3 N4 113.2(2) . . ? N3 C3 N2 133.2(2) . . ? N3 C3 N4 113.6(2) . . ? N4 C4 H4 125.8 . . ? N5 C4 N4 108.4(2) . . ? N5 C4 H4 125.8 . . ? N4 C5 H5 126.7 . . ? C6 C5 N4 106.6(2) . . ? C6 C5 H5 126.7 . . ? N5 C6 H6 126.2 . . ? C5 C6 N5 107.7(2) . . ? C5 C6 H6 126.2 . . ? N5 C7 H7A 109.2 . . ? N5 C7 H7B 109.2 . . ? N5 C7 C8 112.2(2) . . ? H7A C7 H7B 107.9 . . ? C8 C7 H7A 109.2 . . ? C8 C7 H7B 109.2 . . ? C7 C8 H8A 107.7 . . ? C7 C8 H8B 107.7 . . ? H8A C8 H8B 107.1 . . ? C9 C8 C7 118.3(3) . . ? C9 C8 H8A 107.7 . . ? C9 C8 H8B 107.7 . . ? C8 C9 H9A 108.3 . . ? C8 C9 H9B 108.3 . . ? C8 C9 C10 116.0(4) . . ? H9A C9 H9B 107.4 . . ? C10 C9 H9A 108.3 . . ? C10 C9 H9B 108.3 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10B 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O3 C11 C12 121.0(5) . . ? O3 C11 C13 119.7(6) . . ? C13 C11 C12 119.3(5) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12B 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13B 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? 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 N1 H1 O1 0.86 1.95 2.809(3) 174.6 2_755