# 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_ia2211 _database_code_depnum_ccdc_archive 'CCDC 885513' #TrackingRef 'web_deposit_cif_file_0_XinSu_1339039487.4NMe2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C17 H20 N4 O2' _chemical_formula_sum 'C17 H20 N4 O2' _chemical_melting_point ? _exptl_crystal_description block _exptl_crystal_colour orange _diffrn_ambient_temperature 173(2) _chemical_formula_weight 312.37 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_int_tables_number 14 _chemical_absolute_configuration ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 18.9390(13) _cell_length_b 7.5769(5) _cell_length_c 11.1814(8) _cell_angle_alpha 90.00 _cell_angle_beta 93.5940(10) _cell_angle_gamma 90.00 _cell_volume 1601.36(19) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9994 _cell_measurement_theta_min 2.15 _cell_measurement_theta_max 25.32 _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.296 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9685 _exptl_absorpt_correction_T_max 0.9849 _exptl_absorpt_process_details SADABS _exptl_special_details ; Data was collected using a BRUKER CCD (charge coupled device) based diffractometer equipped with an Oxford low-temperature apparatus operating at 173 K. A suitable crystal was chosen and mounted on a glass fiber or nylon loop using Paratone oil for Mo radiation and Mineral oil for Copper radiation. Data were measured using omega and phi scans of 0.5\% per frame for 30 s. The total number of images were based on results from the program COSMO where redundancy was expected to be 4 and completeness to 0.83\%A to 100%. Cell parameters were retrieved using APEX II software and refined using SAINT on all observed reflections.Data reduction was performed using the SAINT software which corrects for Lp. Scaling and absorption corrections were applied using SADABS6 multi-scan technique, supplied by George Sheldrick. The structures are solved by the direct method using the SHELXS-97 program and refined by least squares method on F2, SHELXL-97, incorporated in SHELXTL-PC V 6.14. All H atoms were placed in calculated positions and refined using a riding model. C-H(aromatic) = 0.94 \%A and Uiso(H) = 1.2Ueq(C) C-H (alaphatic) = 0.99 \%A and Uiso(H) = 1.2Ueq(C) CH2 = 0.98 \%A and Uiso(H) = 1.2Ueq(C) CH3 = 0.97\%A and Uiso(H) = 1.5Ueq(C) N-H = 0.86 (0.92)\%A and Uiso(H) = 1.2 Ueq(N) O-H(alcohol) = 0.85\%Aand Uiso(H) = 1.2Ueq(O) O-H(acid) = 0.82\%A and Uiso(H) = 1.5Ueq(O) ; _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 'Bruker APEX-II CCD' _diffrn_measurement_method '\w,and/f 0.5 deg' _diffrn_detector_area_resol_mean 836.6 _diffrn_reflns_number 25125 _diffrn_reflns_av_R_equivalents 0.0263 _diffrn_reflns_av_sigmaI/netI 0.0124 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 25.32 _reflns_number_total 2925 _reflns_number_gt 2613 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COSMO (BRUKER, V1.61, 2009)' _computing_cell_refinement 'APEX2 (BRUKER, V2010.11-3, 2010)' _computing_data_reduction 'SAINT (BRUKER, V7.68A, 2010)' _computing_structure_solution 'SHELXS (Sheldrick, Acta Cryst. A64 2008, 112-122)' _computing_structure_refinement 'SHELXL (Sheldrick, Acta Cryst. A64 2008, 112-122)' _computing_molecular_graphics 'SHELXTL (Sheldrick, Acta Cryst. A64 2008, 112-122)' _computing_publication_material 'SHELXTL (Sheldrick, Acta Cryst. A64 2008, 112-122)' _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^)+(0.0458P)^2^+0.4362P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2925 _refine_ls_number_parameters 211 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0367 _refine_ls_R_factor_gt 0.0324 _refine_ls_wR_factor_ref 0.0900 _refine_ls_wR_factor_gt 0.0854 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.72328(4) 0.55732(13) 0.45185(7) 0.0392(2) Uani 1 1 d . . . O2 O 0.61142(4) 0.62110(13) 0.48867(8) 0.0407(2) Uani 1 1 d . . . N1 N 0.77380(5) 0.39159(13) 0.77390(8) 0.0273(2) Uani 1 1 d . . . H1 H 0.7433 0.3630 0.8268 0.033 Uiso 1 1 calc R . . N2 N 0.75128(5) 0.45300(12) 0.66817(8) 0.0269(2) Uani 1 1 d . . . N3 N 0.64171(5) 0.41177(14) 0.83392(9) 0.0313(2) Uani 1 1 d . . . N5 N 1.06365(5) 0.32572(14) 0.89955(8) 0.0294(2) Uani 1 1 d . . . C1 C 0.84674(6) 0.37183(14) 0.80211(9) 0.0239(2) Uani 1 1 d . . . C2 C 0.89684(6) 0.43599(14) 0.72764(9) 0.0251(2) Uani 1 1 d . . . H2 H 0.8818 0.4905 0.6539 0.030 Uiso 1 1 calc R . . C3 C 0.96812(6) 0.42139(15) 0.75966(9) 0.0253(2) Uani 1 1 d . . . H3 H 1.0014 0.4667 0.7075 0.030 Uiso 1 1 calc R . . C4 C 0.99257(6) 0.34098(14) 0.86782(9) 0.0236(2) Uani 1 1 d . . . C5 C 0.94094(6) 0.27554(15) 0.94143(9) 0.0262(2) Uani 1 1 d . . . H5 H 0.9555 0.2202 1.0151 0.031 Uiso 1 1 calc R . . C6 C 0.86948(6) 0.29000(15) 0.90887(10) 0.0269(2) Uani 1 1 d . . . H6 H 0.8357 0.2437 0.9599 0.032 Uiso 1 1 calc R . . C7 C 1.11533(6) 0.41534(18) 0.83173(11) 0.0356(3) Uani 1 1 d . . . H7A H 1.1148 0.3650 0.7510 0.053 Uiso 1 1 calc R . . H7B H 1.1625 0.4006 0.8719 0.053 Uiso 1 1 calc R . . H7C H 1.1037 0.5413 0.8264 0.053 Uiso 1 1 calc R . . C8 C 1.08694(6) 0.24822(17) 1.01339(10) 0.0319(3) Uani 1 1 d . . . H8A H 1.0714 0.3223 1.0786 0.048 Uiso 1 1 calc R . . H8B H 1.1387 0.2399 1.0192 0.048 Uiso 1 1 calc R . . H8C H 1.0665 0.1300 1.0195 0.048 Uiso 1 1 calc R . . C9 C 0.68349(6) 0.47371(15) 0.63970(10) 0.0264(2) Uani 1 1 d . . . C10 C 0.66781(6) 0.55649(16) 0.52075(10) 0.0284(3) Uani 1 1 d . . . C11 C 0.71381(7) 0.65174(18) 0.33882(11) 0.0360(3) Uani 1 1 d . . . H11A H 0.7593 0.7059 0.3196 0.043 Uiso 1 1 calc R . . H11B H 0.6790 0.7478 0.3467 0.043 Uiso 1 1 calc R . . C12 C 0.68866(8) 0.53161(18) 0.23880(12) 0.0428(3) Uani 1 1 d . . . H12A H 0.7235 0.4377 0.2298 0.064 Uiso 1 1 calc R . . H12B H 0.6828 0.5991 0.1641 0.064 Uiso 1 1 calc R . . H12C H 0.6432 0.4793 0.2570 0.064 Uiso 1 1 calc R . . C13 C 0.62451(6) 0.42875(14) 0.71525(10) 0.0264(2) Uani 1 1 d . . . C14 C 0.55553(6) 0.39698(16) 0.66856(11) 0.0314(3) Uani 1 1 d . . . H14 H 0.5438 0.4098 0.5852 0.038 Uiso 1 1 calc R . . C15 C 0.50468(7) 0.34688(18) 0.74458(12) 0.0379(3) Uani 1 1 d . . . H15 H 0.4580 0.3211 0.7136 0.046 Uiso 1 1 calc R . . C16 C 0.52197(7) 0.33432(18) 0.86623(12) 0.0389(3) Uani 1 1 d . . . H16 H 0.4874 0.3033 0.9205 0.047 Uiso 1 1 calc R . . C17 C 0.59079(7) 0.36821(18) 0.90610(11) 0.0369(3) Uani 1 1 d . . . H17 H 0.6028 0.3602 0.9897 0.044 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 0.0289(5) 0.0576(6) 0.0317(5) 0.0154(4) 0.0056(3) 0.0090(4) O2 0.0292(5) 0.0575(6) 0.0357(5) 0.0130(4) 0.0034(4) 0.0130(4) N1 0.0239(5) 0.0341(5) 0.0240(5) 0.0040(4) 0.0010(4) -0.0013(4) N2 0.0273(5) 0.0277(5) 0.0253(5) 0.0006(4) -0.0008(4) 0.0007(4) N3 0.0299(5) 0.0366(6) 0.0276(5) 0.0007(4) 0.0022(4) -0.0039(4) N5 0.0241(5) 0.0364(5) 0.0276(5) 0.0026(4) 0.0003(4) 0.0003(4) C1 0.0242(5) 0.0235(5) 0.0239(5) -0.0024(4) 0.0004(4) -0.0002(4) C2 0.0299(6) 0.0253(5) 0.0200(5) 0.0008(4) 0.0009(4) 0.0006(4) C3 0.0276(6) 0.0260(6) 0.0226(5) -0.0006(4) 0.0052(4) -0.0011(4) C4 0.0257(5) 0.0220(5) 0.0230(5) -0.0036(4) 0.0014(4) 0.0011(4) C5 0.0298(6) 0.0276(6) 0.0211(5) 0.0025(4) 0.0007(4) 0.0015(5) C6 0.0274(6) 0.0297(6) 0.0242(5) 0.0025(4) 0.0046(4) -0.0023(5) C7 0.0257(6) 0.0499(8) 0.0316(6) -0.0022(5) 0.0035(5) -0.0041(5) C8 0.0291(6) 0.0366(7) 0.0294(6) -0.0013(5) -0.0034(5) 0.0054(5) C9 0.0245(6) 0.0281(6) 0.0266(6) -0.0008(4) 0.0004(4) 0.0015(4) C10 0.0248(6) 0.0319(6) 0.0286(6) -0.0001(5) 0.0019(4) 0.0019(5) C11 0.0334(6) 0.0432(7) 0.0317(6) 0.0126(5) 0.0046(5) 0.0013(5) C12 0.0526(8) 0.0400(7) 0.0360(7) 0.0065(6) 0.0059(6) 0.0056(6) C13 0.0275(6) 0.0245(5) 0.0274(6) -0.0013(4) 0.0017(4) 0.0021(4) C14 0.0276(6) 0.0352(6) 0.0312(6) 0.0007(5) -0.0002(5) 0.0025(5) C15 0.0249(6) 0.0435(7) 0.0452(7) 0.0040(6) 0.0010(5) 0.0000(5) C16 0.0309(6) 0.0456(8) 0.0411(7) 0.0071(6) 0.0096(5) -0.0015(5) C17 0.0369(7) 0.0450(7) 0.0294(6) 0.0035(5) 0.0057(5) -0.0043(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 C10 1.3411(14) . ? O1 C11 1.4535(14) . ? O2 C10 1.2087(14) . ? N1 N2 1.3163(13) . ? N1 C1 1.4057(14) . ? N1 H1 0.8800 . ? N2 C9 1.3127(14) . ? N3 C17 1.3371(15) . ? N3 C13 1.3525(15) . ? N5 C4 1.3753(14) . ? N5 C7 1.4446(15) . ? N5 C8 1.4454(14) . ? C1 C2 1.3888(16) . ? C1 C6 1.3893(15) . ? C2 C3 1.3793(16) . ? C2 H2 0.9500 . ? C3 C4 1.4065(15) . ? C3 H3 0.9500 . ? C4 C5 1.4073(15) . ? C5 C6 1.3835(15) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C13 1.4817(15) . ? C9 C10 1.4836(16) . ? C11 C12 1.4965(19) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C14 1.3971(16) . ? C14 C15 1.3771(18) . ? C14 H14 0.9500 . ? C15 C16 1.3823(19) . ? C15 H15 0.9500 . ? C16 C17 1.3750(18) . ? C16 H16 0.9500 . ? C17 H17 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 C10 O1 C11 116.32(9) . . ? N2 N1 C1 119.85(9) . . ? N2 N1 H1 120.1 . . ? C1 N1 H1 120.1 . . ? C9 N2 N1 121.13(9) . . ? C17 N3 C13 118.50(10) . . ? C4 N5 C7 120.62(10) . . ? C4 N5 C8 120.07(9) . . ? C7 N5 C8 118.29(9) . . ? C2 C1 C6 118.99(10) . . ? C2 C1 N1 121.79(10) . . ? C6 C1 N1 119.19(10) . . ? C3 C2 C1 120.70(10) . . ? C3 C2 H2 119.6 . . ? C1 C2 H2 119.6 . . ? C2 C3 C4 121.47(10) . . ? C2 C3 H3 119.3 . . ? C4 C3 H3 119.3 . . ? N5 C4 C3 121.50(10) . . ? N5 C4 C5 121.62(10) . . ? C3 C4 C5 116.88(10) . . ? C6 C5 C4 121.49(10) . . ? C6 C5 H5 119.3 . . ? C4 C5 H5 119.3 . . ? C5 C6 C1 120.46(10) . . ? C5 C6 H6 119.8 . . ? C1 C6 H6 119.8 . . ? N5 C7 H7A 109.5 . . ? N5 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? N5 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N5 C8 H8A 109.5 . . ? N5 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N5 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N2 C9 C13 126.51(10) . . ? N2 C9 C10 113.93(10) . . ? C13 C9 C10 119.52(10) . . ? O2 C10 O1 122.48(10) . . ? O2 C10 C9 124.11(10) . . ? O1 C10 C9 113.39(9) . . ? O1 C11 C12 111.51(11) . . ? O1 C11 H11A 109.3 . . ? C12 C11 H11A 109.3 . . ? O1 C11 H11B 109.3 . . ? C12 C11 H11B 109.3 . . ? H11A C11 H11B 108.0 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N3 C13 C14 120.82(10) . . ? N3 C13 C9 115.94(10) . . ? C14 C13 C9 123.17(10) . . ? C15 C14 C13 119.37(11) . . ? C15 C14 H14 120.3 . . ? C13 C14 H14 120.3 . . ? C14 C15 C16 119.65(12) . . ? C14 C15 H15 120.2 . . ? C16 C15 H15 120.2 . . ? C17 C16 C15 117.87(11) . . ? C17 C16 H16 121.1 . . ? C15 C16 H16 121.1 . . ? N3 C17 C16 123.73(12) . . ? N3 C17 H17 118.1 . . ? C16 C17 H17 118.1 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 N1 N2 C9 -179.62(10) . . . . ? N2 N1 C1 C2 8.33(16) . . . . ? N2 N1 C1 C6 -173.37(10) . . . . ? C6 C1 C2 C3 -0.98(16) . . . . ? N1 C1 C2 C3 177.32(10) . . . . ? C1 C2 C3 C4 0.26(16) . . . . ? C7 N5 C4 C3 9.46(16) . . . . ? C8 N5 C4 C3 177.71(10) . . . . ? C7 N5 C4 C5 -171.12(11) . . . . ? C8 N5 C4 C5 -2.87(16) . . . . ? C2 C3 C4 N5 179.72(10) . . . . ? C2 C3 C4 C5 0.28(16) . . . . ? N5 C4 C5 C6 -179.55(10) . . . . ? C3 C4 C5 C6 -0.10(16) . . . . ? C4 C5 C6 C1 -0.61(17) . . . . ? C2 C1 C6 C5 1.15(16) . . . . ? N1 C1 C6 C5 -177.19(10) . . . . ? N1 N2 C9 C13 -2.09(17) . . . . ? N1 N2 C9 C10 175.71(10) . . . . ? C11 O1 C10 O2 4.26(18) . . . . ? C11 O1 C10 C9 -174.15(10) . . . . ? N2 C9 C10 O2 -163.47(12) . . . . ? C13 C9 C10 O2 14.50(18) . . . . ? N2 C9 C10 O1 14.91(15) . . . . ? C13 C9 C10 O1 -167.12(10) . . . . ? C10 O1 C11 C12 -92.74(13) . . . . ? C17 N3 C13 C14 -1.67(17) . . . . ? C17 N3 C13 C9 -178.83(11) . . . . ? N2 C9 C13 N3 19.48(17) . . . . ? C10 C9 C13 N3 -158.21(10) . . . . ? N2 C9 C13 C14 -157.60(11) . . . . ? C10 C9 C13 C14 24.71(16) . . . . ? N3 C13 C14 C15 -0.34(18) . . . . ? C9 C13 C14 C15 176.60(11) . . . . ? C13 C14 C15 C16 2.09(19) . . . . ? C14 C15 C16 C17 -1.8(2) . . . . ? C13 N3 C17 C16 2.01(19) . . . . ? C15 C16 C17 N3 -0.3(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 N3 0.88 1.96 2.6348(13) 131.9 . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.32 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.143 _refine_diff_density_min -0.202 _refine_diff_density_rms 0.043 _contact_Crystallographer_name 'Richard Staples' _contact_Crystallographer_email staples@chemistry.msu.com data_ia2011 _database_code_depnum_ccdc_archive 'CCDC 885514' #TrackingRef 'web_deposit_cif_file_1_XinSu_1339039487.4-OnHex.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C21 H27 N3 O3' _chemical_formula_sum 'C21 H27 N3 O3' _chemical_melting_point ? _exptl_crystal_description plate _exptl_crystal_colour yellow _diffrn_ambient_temperature 173(2) _chemical_formula_weight 369.46 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_int_tables_number 14 _chemical_absolute_configuration ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 21.5273(7) _cell_length_b 14.3929(5) _cell_length_c 6.4359(2) _cell_angle_alpha 90.00 _cell_angle_beta 96.137(3) _cell_angle_gamma 90.00 _cell_volume 1982.67(11) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2412 _cell_measurement_theta_min 3.70 _cell_measurement_theta_max 67.66 _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.238 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 792 _exptl_absorpt_coefficient_mu 0.673 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8743 _exptl_absorpt_correction_T_max 0.9500 _exptl_absorpt_process_details SADABS _exptl_special_details ; Data was collected using a BRUKER CCD (charge coupled device) based diffractometer equipped with an Oxford low-temperature apparatus operating at 173 K. A suitable crystal was chosen and mounted on a glass fiber or nylon loop using Paratone oil for Mo radiation and Mineral oil for Copper radiation. Data were measured using omega and Phi scans of 0.5\% per frame for 30 s. The total number of images were based on results from the program COSMO where redundancy was expected to be 4.0 and completeness to 0.83\%A to 100%. Cell parameters were retrieved using APEX II software and refined using SAINT on all observed reflections. Data reduction was performed using the SAINT software which corrects for Lp. Scaling and absorption corrections were applied using SADABS6 multi-scan technique, supplied by George Sheldrick. The structures are solved by the direct method using the SHELXS-97 program and refined by least squares method on F2, SHELXL-97, incorporated in SHELXTL-PC V 6.14. All H atoms were found by difference Fourier methods and refined isotrpically. ; _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\w,and/f 0.5 deg' _diffrn_detector_area_resol_mean 836.6 _diffrn_reflns_number 14479 _diffrn_reflns_av_R_equivalents 0.0981 _diffrn_reflns_av_sigmaI/netI 0.0765 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 68.23 _reflns_number_total 3505 _reflns_number_gt 1990 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COSMO (BRUKER, V1.61, 2009)' _computing_cell_refinement 'APEX2 (BRUKER, V2010.11-3, 2010)' _computing_data_reduction 'SAINT (BRUKER, V7.68A, 2010)' _computing_structure_solution 'SHELXS (Sheldrick, Acta Cryst. A64 2008, 112-122)' _computing_structure_refinement 'SHELXL (Sheldrick, Acta Cryst. A64 2008, 112-122)' _computing_molecular_graphics 'SHELXTL (Sheldrick, Acta Cryst. A64 2008, 112-122)' _computing_publication_material 'SHELXTL (Sheldrick, Acta Cryst. A64 2008, 112-122)' _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^)+(0.0520P)^2^+0.6884P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3505 _refine_ls_number_parameters 352 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1220 _refine_ls_R_factor_gt 0.0594 _refine_ls_wR_factor_ref 0.1399 _refine_ls_wR_factor_gt 0.1154 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.014 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.64285(10) 1.08020(18) 0.5437(3) 0.0592(7) Uani 1 1 d . . . O2 O 0.58361(11) 1.0853(2) 0.8074(4) 0.0692(8) Uani 1 1 d . . . O3 O 0.99057(8) 0.85584(13) 0.5170(3) 0.0326(5) Uani 1 1 d . . . N1 N 0.71709(11) 0.96029(18) 0.7316(4) 0.0356(6) Uani 1 1 d . . . N2 N 0.75918(11) 0.89914(18) 0.8116(4) 0.0333(6) Uani 1 1 d . . . H2 H 0.7520(13) 0.872(2) 0.941(5) 0.046(9) Uiso 1 1 d . . . N3 N 0.69147(11) 0.87893(18) 1.1256(4) 0.0377(7) Uani 1 1 d . . . C1 C 0.66500(13) 0.9722(2) 0.8180(4) 0.0356(7) Uani 1 1 d . . . C2 C 0.62582(14) 1.0499(3) 0.7237(5) 0.0446(9) Uani 1 1 d . . . C3 C 0.60964(18) 1.1648(3) 0.4581(6) 0.0588(11) Uani 1 1 d . . . H3A H 0.5965(15) 1.204(2) 0.576(5) 0.058(11) Uiso 1 1 d . . . H3B H 0.6393(16) 1.192(2) 0.378(6) 0.064(11) Uiso 1 1 d . . . C4 C 0.5511(2) 1.1372(4) 0.3301(7) 0.0673(12) Uani 1 1 d . . . H4A H 0.5319(19) 1.201(3) 0.261(7) 0.113(16) Uiso 1 1 d . . . H4B H 0.5263(18) 1.093(3) 0.413(7) 0.094(15) Uiso 1 1 d . . . H4C H 0.566(2) 1.099(4) 0.219(8) 0.119(18) Uiso 1 1 d . . . C5 C 0.64569(13) 0.9227(2) 1.0029(4) 0.0345(7) Uani 1 1 d . . . C6 C 0.58367(15) 0.9170(3) 1.0459(5) 0.0438(9) Uani 1 1 d . . . H6 H 0.5531(13) 0.949(2) 0.953(5) 0.042(9) Uiso 1 1 d . . . C7 C 0.56931(18) 0.8698(3) 1.2197(6) 0.0517(10) Uani 1 1 d . . . H7 H 0.5289(14) 0.863(2) 1.248(5) 0.048(10) Uiso 1 1 d . . . C8 C 0.61627(16) 0.8278(3) 1.3478(6) 0.0482(9) Uani 1 1 d . . . H8 H 0.6075(14) 0.794(2) 1.470(5) 0.060(11) Uiso 1 1 d . . . C9 C 0.67637(16) 0.8340(2) 1.2949(5) 0.0429(8) Uani 1 1 d . . . H9 H 0.7106(12) 0.8012(19) 1.370(4) 0.029(8) Uiso 1 1 d . . . C10 C 0.81592(12) 0.8897(2) 0.7246(4) 0.0306(7) Uani 1 1 d . . . C11 C 0.86291(13) 0.8377(2) 0.8370(4) 0.0310(7) Uani 1 1 d . . . H11 H 0.8538(12) 0.8075(19) 0.970(4) 0.033(8) Uiso 1 1 d . . . C12 C 0.92046(13) 0.8284(2) 0.7627(4) 0.0301(7) Uani 1 1 d . . . H12 H 0.9535(13) 0.7917(19) 0.835(4) 0.037(8) Uiso 1 1 d . . . C13 C 0.93162(12) 0.8701(2) 0.5749(4) 0.0290(7) Uani 1 1 d . . . C14 C 0.88451(13) 0.9202(2) 0.4624(4) 0.0315(7) Uani 1 1 d . . . H14 H 0.8926(12) 0.9500(19) 0.332(4) 0.033(8) Uiso 1 1 d . . . C15 C 0.82696(13) 0.9303(2) 0.5365(4) 0.0330(7) Uani 1 1 d . . . H15 H 0.7951(12) 0.9675(19) 0.458(4) 0.031(8) Uiso 1 1 d . . . C16 C 1.00437(13) 0.8913(2) 0.3174(4) 0.0307(7) Uani 1 1 d . . . H16A H 1.0035(12) 0.962(2) 0.322(4) 0.033(8) Uiso 1 1 d . . . H16B H 0.9717(12) 0.8708(18) 0.207(4) 0.032(8) Uiso 1 1 d . . . C17 C 1.06836(14) 0.8558(2) 0.2855(5) 0.0343(7) Uani 1 1 d . . . H17A H 1.0955(13) 0.873(2) 0.410(5) 0.046(9) Uiso 1 1 d . . . H17B H 1.0676(13) 0.787(2) 0.274(4) 0.042(9) Uiso 1 1 d . . . C18 C 1.09390(14) 0.8943(3) 0.0914(5) 0.0336(7) Uani 1 1 d . . . H18A H 1.0667(13) 0.878(2) -0.028(5) 0.044(9) Uiso 1 1 d . . . H18B H 1.0952(13) 0.961(2) 0.096(4) 0.041(9) Uiso 1 1 d . . . C19 C 1.15927(14) 0.8583(2) 0.0686(5) 0.0339(7) Uani 1 1 d . . . H19A H 1.1875(12) 0.8776(18) 0.192(4) 0.028(7) Uiso 1 1 d . . . H19B H 1.1577(12) 0.793(2) 0.065(4) 0.031(8) Uiso 1 1 d . . . C20 C 1.18699(15) 0.8948(3) -0.1222(5) 0.0385(8) Uani 1 1 d . . . H20A H 1.1574(14) 0.885(2) -0.255(5) 0.052(9) Uiso 1 1 d . . . H20B H 1.1902(13) 0.961(2) -0.114(5) 0.046(10) Uiso 1 1 d . . . C21 C 1.25031(18) 0.8542(3) -0.1523(7) 0.0530(10) Uani 1 1 d . . . H21A H 1.2675(17) 0.879(3) -0.274(6) 0.076(13) Uiso 1 1 d . . . H21B H 1.2816(15) 0.863(2) -0.036(6) 0.059(11) Uiso 1 1 d . . . H21C H 1.2484(14) 0.786(3) -0.165(5) 0.055(11) 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 0.0537(14) 0.078(2) 0.0485(15) 0.0272(13) 0.0187(11) 0.0284(13) O2 0.0676(17) 0.092(2) 0.0511(15) 0.0191(14) 0.0210(13) 0.0446(16) O3 0.0320(11) 0.0373(13) 0.0297(11) 0.0018(9) 0.0081(8) 0.0008(9) N1 0.0351(14) 0.0404(17) 0.0311(14) 0.0006(12) 0.0034(11) 0.0060(13) N2 0.0329(14) 0.0371(16) 0.0304(14) 0.0068(12) 0.0055(11) 0.0050(12) N3 0.0364(14) 0.0453(18) 0.0310(13) 0.0041(12) 0.0024(11) 0.0013(12) C1 0.0327(17) 0.044(2) 0.0298(16) 0.0005(14) 0.0044(13) 0.0052(15) C2 0.0398(19) 0.060(2) 0.0349(18) 0.0014(16) 0.0081(15) 0.0093(17) C3 0.049(2) 0.076(3) 0.053(2) 0.024(2) 0.0120(19) 0.013(2) C4 0.083(3) 0.069(3) 0.048(2) 0.006(2) 0.003(2) 0.013(3) C5 0.0334(16) 0.037(2) 0.0330(16) -0.0060(13) 0.0051(13) 0.0020(15) C6 0.0332(18) 0.050(2) 0.049(2) -0.0039(17) 0.0102(16) 0.0050(17) C7 0.043(2) 0.055(3) 0.062(2) -0.0057(19) 0.0271(19) -0.0022(19) C8 0.056(2) 0.049(2) 0.043(2) 0.0013(17) 0.0209(17) -0.0029(19) C9 0.046(2) 0.049(2) 0.0338(17) 0.0041(15) 0.0064(15) 0.0032(17) C10 0.0279(15) 0.0301(18) 0.0344(16) -0.0031(13) 0.0062(12) -0.0029(13) C11 0.0386(17) 0.0282(18) 0.0264(15) 0.0009(13) 0.0042(12) -0.0010(14) C12 0.0326(17) 0.0284(18) 0.0293(16) -0.0008(13) 0.0040(12) 0.0024(14) C13 0.0287(16) 0.0270(18) 0.0313(16) -0.0054(12) 0.0023(12) -0.0016(13) C14 0.0340(16) 0.036(2) 0.0254(15) 0.0023(13) 0.0069(12) 0.0014(15) C15 0.0329(17) 0.035(2) 0.0311(16) 0.0060(13) 0.0026(13) 0.0076(14) C16 0.0346(17) 0.031(2) 0.0265(15) 0.0019(13) 0.0027(12) -0.0030(14) C17 0.0371(18) 0.033(2) 0.0335(18) 0.0011(14) 0.0066(14) 0.0015(15) C18 0.0357(17) 0.035(2) 0.0309(16) 0.0002(14) 0.0052(13) -0.0027(15) C19 0.0360(18) 0.033(2) 0.0327(17) 0.0022(14) 0.0045(13) -0.0013(15) C20 0.0394(19) 0.042(2) 0.0359(18) 0.0001(15) 0.0109(15) -0.0011(16) C21 0.042(2) 0.060(3) 0.060(3) -0.008(2) 0.0174(19) -0.003(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 O1 C2 1.325(3) . ? O1 C3 1.488(4) . ? O2 C2 1.217(3) . ? O3 C13 1.376(3) . ? O3 C16 1.442(3) . ? N1 C1 1.315(3) . ? N1 N2 1.327(3) . ? N2 C10 1.404(3) . ? N2 H2 0.95(3) . ? N3 C9 1.337(4) . ? N3 C5 1.351(4) . ? C1 C5 1.484(4) . ? C1 C2 1.490(4) . ? C3 C4 1.484(6) . ? C3 H3A 1.01(3) . ? C3 H3B 0.95(3) . ? C4 H4A 1.08(5) . ? C4 H4B 1.02(4) . ? C4 H4C 0.98(5) . ? C5 C6 1.395(4) . ? C6 C7 1.372(5) . ? C6 H6 0.96(3) . ? C7 C8 1.374(5) . ? C7 H7 0.91(3) . ? C8 C9 1.376(4) . ? C8 H8 0.96(3) . ? C9 H9 0.96(3) . ? C10 C15 1.388(4) . ? C10 C11 1.396(4) . ? C11 C12 1.381(4) . ? C11 H11 1.00(3) . ? C12 C13 1.392(4) . ? C12 H12 0.96(3) . ? C13 C14 1.384(4) . ? C14 C15 1.382(4) . ? C14 H14 0.98(3) . ? C15 H15 0.97(3) . ? C16 C17 1.504(4) . ? C16 H16A 1.01(3) . ? C16 H16B 0.99(3) . ? C17 C18 1.522(4) . ? C17 H17A 0.97(3) . ? C17 H17B 0.99(3) . ? C18 C19 1.521(4) . ? C18 H18A 0.95(3) . ? C18 H18B 0.96(3) . ? C19 C20 1.515(4) . ? C19 H19A 0.99(3) . ? C19 H19B 0.95(3) . ? C20 C21 1.514(5) . ? C20 H20A 1.02(3) . ? C20 H20B 0.96(3) . ? C21 H21A 0.97(4) . ? C21 H21B 0.96(3) . ? C21 H21C 0.98(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 C2 O1 C3 115.2(3) . . ? C13 O3 C16 118.2(2) . . ? C1 N1 N2 120.0(2) . . ? N1 N2 C10 119.8(2) . . ? N1 N2 H2 116.4(18) . . ? C10 N2 H2 122.9(18) . . ? C9 N3 C5 118.5(3) . . ? N1 C1 C5 126.9(3) . . ? N1 C1 C2 113.4(3) . . ? C5 C1 C2 119.5(3) . . ? O2 C2 O1 122.6(3) . . ? O2 C2 C1 123.4(3) . . ? O1 C2 C1 113.9(3) . . ? C4 C3 O1 109.4(4) . . ? C4 C3 H3A 106.1(19) . . ? O1 C3 H3A 109.7(19) . . ? C4 C3 H3B 113(2) . . ? O1 C3 H3B 102(2) . . ? H3A C3 H3B 116(3) . . ? C3 C4 H4A 105(2) . . ? C3 C4 H4B 110(2) . . ? H4A C4 H4B 123(3) . . ? C3 C4 H4C 103(3) . . ? H4A C4 H4C 109(4) . . ? H4B C4 H4C 105(4) . . ? N3 C5 C6 120.7(3) . . ? N3 C5 C1 116.3(2) . . ? C6 C5 C1 122.9(3) . . ? C7 C6 C5 119.7(3) . . ? C7 C6 H6 123.1(18) . . ? C5 C6 H6 117.2(18) . . ? C6 C7 C8 119.4(3) . . ? C6 C7 H7 121(2) . . ? C8 C7 H7 119(2) . . ? C7 C8 C9 118.3(3) . . ? C7 C8 H8 121.2(19) . . ? C9 C8 H8 120(2) . . ? N3 C9 C8 123.3(3) . . ? N3 C9 H9 114.2(16) . . ? C8 C9 H9 122.2(16) . . ? C15 C10 C11 119.7(3) . . ? C15 C10 N2 123.0(3) . . ? C11 C10 N2 117.3(3) . . ? C12 C11 C10 120.0(3) . . ? C12 C11 H11 121.4(15) . . ? C10 C11 H11 118.6(15) . . ? C11 C12 C13 120.2(3) . . ? C11 C12 H12 121.9(16) . . ? C13 C12 H12 117.9(16) . . ? O3 C13 C14 125.5(3) . . ? O3 C13 C12 114.9(2) . . ? C14 C13 C12 119.6(3) . . ? C15 C14 C13 120.5(3) . . ? C15 C14 H14 120.1(16) . . ? C13 C14 H14 119.4(15) . . ? C14 C15 C10 120.0(3) . . ? C14 C15 H15 119.3(16) . . ? C10 C15 H15 120.7(16) . . ? O3 C16 C17 106.3(2) . . ? O3 C16 H16A 108.9(15) . . ? C17 C16 H16A 111.3(15) . . ? O3 C16 H16B 109.6(15) . . ? C17 C16 H16B 113.0(15) . . ? H16A C16 H16B 108(2) . . ? C16 C17 C18 113.9(3) . . ? C16 C17 H17A 106.2(18) . . ? C18 C17 H17A 110.0(18) . . ? C16 C17 H17B 109.9(16) . . ? C18 C17 H17B 108.0(16) . . ? H17A C17 H17B 109(2) . . ? C19 C18 C17 112.0(3) . . ? C19 C18 H18A 109.4(18) . . ? C17 C18 H18A 109.1(18) . . ? C19 C18 H18B 108.6(17) . . ? C17 C18 H18B 110.6(17) . . ? H18A C18 H18B 107(2) . . ? C20 C19 C18 114.1(3) . . ? C20 C19 H19A 107.0(15) . . ? C18 C19 H19A 108.8(15) . . ? C20 C19 H19B 109.9(16) . . ? C18 C19 H19B 108.1(16) . . ? H19A C19 H19B 109(2) . . ? C21 C20 C19 114.1(3) . . ? C21 C20 H20A 109.2(17) . . ? C19 C20 H20A 111.3(17) . . ? C21 C20 H20B 109.3(18) . . ? C19 C20 H20B 109.4(18) . . ? H20A C20 H20B 103(2) . . ? C20 C21 H21A 113(2) . . ? C20 C21 H21B 115(2) . . ? H21A C21 H21B 107(3) . . ? C20 C21 H21C 111.3(19) . . ? H21A C21 H21C 108(3) . . ? H21B C21 H21C 102(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 N1 N2 C10 -177.1(3) . . . . ? N2 N1 C1 C5 -0.7(5) . . . . ? N2 N1 C1 C2 174.0(3) . . . . ? C3 O1 C2 O2 4.0(5) . . . . ? C3 O1 C2 C1 -173.0(3) . . . . ? N1 C1 C2 O2 -163.4(3) . . . . ? C5 C1 C2 O2 11.7(5) . . . . ? N1 C1 C2 O1 13.6(4) . . . . ? C5 C1 C2 O1 -171.2(3) . . . . ? C2 O1 C3 C4 -87.2(4) . . . . ? C9 N3 C5 C6 -3.3(4) . . . . ? C9 N3 C5 C1 179.5(3) . . . . ? N1 C1 C5 N3 17.9(5) . . . . ? C2 C1 C5 N3 -156.5(3) . . . . ? N1 C1 C5 C6 -159.2(3) . . . . ? C2 C1 C5 C6 26.3(5) . . . . ? N3 C5 C6 C7 2.8(5) . . . . ? C1 C5 C6 C7 179.9(3) . . . . ? C5 C6 C7 C8 -0.8(5) . . . . ? C6 C7 C8 C9 -0.7(6) . . . . ? C5 N3 C9 C8 1.8(5) . . . . ? C7 C8 C9 N3 0.2(6) . . . . ? N1 N2 C10 C15 -10.8(4) . . . . ? N1 N2 C10 C11 168.3(3) . . . . ? C15 C10 C11 C12 1.2(4) . . . . ? N2 C10 C11 C12 -177.9(3) . . . . ? C10 C11 C12 C13 -0.6(4) . . . . ? C16 O3 C13 C14 -3.6(4) . . . . ? C16 O3 C13 C12 175.8(3) . . . . ? C11 C12 C13 O3 -179.9(2) . . . . ? C11 C12 C13 C14 -0.5(4) . . . . ? O3 C13 C14 C15 -179.7(3) . . . . ? C12 C13 C14 C15 0.9(4) . . . . ? C13 C14 C15 C10 -0.3(5) . . . . ? C11 C10 C15 C14 -0.8(4) . . . . ? N2 C10 C15 C14 178.3(3) . . . . ? C13 O3 C16 C17 -173.3(2) . . . . ? O3 C16 C17 C18 -174.1(3) . . . . ? C16 C17 C18 C19 178.6(3) . . . . ? C17 C18 C19 C20 -179.9(3) . . . . ? C18 C19 C20 C21 -176.3(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 N2 H2 N3 0.95(3) 1.86(3) 2.631(3) 137(3) . _diffrn_measured_fraction_theta_max 0.967 _diffrn_reflns_theta_full 68.23 _diffrn_measured_fraction_theta_full 0.967 _refine_diff_density_max 0.437 _refine_diff_density_min -0.238 _refine_diff_density_rms 0.047 _contact_Crystallographer_email staples@chemistry.msu.com data_ia3311_0m _database_code_depnum_ccdc_archive 'CCDC 885515' #TrackingRef 'web_deposit_cif_file_2_XinSu_1339039487.4Cl.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C15 H14 Cl N3 O2' _chemical_formula_sum 'C15 H14 Cl N3 O2' _chemical_melting_point ? _exptl_crystal_description needle _exptl_crystal_colour yellow _diffrn_ambient_temperature 173(2) _chemical_formula_weight 303.74 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_int_tables_number 19 _chemical_absolute_configuration ad loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' _cell_length_a 4.9468(4) _cell_length_b 9.7236(7) _cell_length_c 29.425(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1415.39(19) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5888 _cell_measurement_theta_min 2.21 _cell_measurement_theta_max 25.34 _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.425 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 0.278 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9233 _exptl_absorpt_correction_T_max 0.9781 _exptl_absorpt_process_details SADABS _exptl_special_details ; Data was collected using a BRUKER CCD (charge coupled device) based diffractometer equipped with an Oxford low-temperature apparatus operating at 173 K. A suitable crystal was chosen and mounted on a glass fiber or nylon loop using Paratone oil for Mo radiation and Mineral oil for Copper radiation. Data were measured using omega and phi scans of 0.5\% per frame for 30 s. The total number of images were based on results from the program COSMO where redundancy was expected to be 4 and completeness to 0.83\%A to 100%. Cell parameters were retrieved using APEX II software and refined using SAINT on all observed reflections.Data reduction was performed using the SAINT software which corrects for Lp. Scaling and absorption corrections were applied using SADABS6 multi-scan technique, supplied by George Sheldrick. The structures are solved by the direct method using the SHELXS-97 program and refined by least squares method on F2, SHELXL-97, incorporated in SHELXTL-PC V 6.14. All H atoms were placed in calculated positions and refined using a riding model. C-H(aromatic) = 0.94 \%A and Uiso(H) = 1.2Ueq(C) C-H (alaphatic) = 0.99 \%A and Uiso(H) = 1.2Ueq(C) CH2 = 0.98 \%A and Uiso(H) = 1.2Ueq(C) CH3 = 0.97\%A and Uiso(H) = 1.5Ueq(C) N-H = 0.86 (0.92)\%A and Uiso(H) = 1.2 Ueq(N) O-H(alcohol) = 0.85\%Aand Uiso(H) = 1.2Ueq(O) O-H(acid) = 0.82\%A and Uiso(H) = 1.5Ueq(O) ; _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 'Bruker APEX-II CCD' _diffrn_measurement_method '\w,and/f 0.5 deg' _diffrn_detector_area_resol_mean 836.6 _diffrn_reflns_number 11499 _diffrn_reflns_av_R_equivalents 0.0307 _diffrn_reflns_av_sigmaI/netI 0.0265 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 2.21 _diffrn_reflns_theta_max 25.38 _reflns_number_total 2590 _reflns_number_gt 2281 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COSMO (BRUKER, V1.61, 2009)' _computing_cell_refinement 'APEX2 (BRUKER, V2010.11-3, 2010)' _computing_data_reduction 'SAINT (BRUKER, V7.68A, 2010)' _computing_structure_solution 'SHELXS (Sheldrick, Acta Cryst. A64 2008, 112-122)' _computing_structure_refinement 'SHELXL (Sheldrick, Acta Cryst. A64 2008, 112-122)' _computing_molecular_graphics 'SHELXTL (Sheldrick, Acta Cryst. A64 2008, 112-122)' _computing_publication_material 'SHELXTL (Sheldrick, Acta Cryst. A64 2008, 112-122)' _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^)+(0.0496P)^2^+1.0243P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.02(10) _refine_ls_number_reflns 2590 _refine_ls_number_parameters 191 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0522 _refine_ls_R_factor_gt 0.0441 _refine_ls_wR_factor_ref 0.1124 _refine_ls_wR_factor_gt 0.1058 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 1.56168(16) 1.06061(8) 0.22749(3) 0.0402(2) Uani 1 1 d . . . O1 O 1.0485(6) 0.5482(3) 0.02001(7) 0.0682(8) Uani 1 1 d . . . O2 O 0.8132(7) 0.3590(3) 0.01442(9) 0.0788(10) Uani 1 1 d . . . N1 N 0.9014(5) 0.6182(2) 0.14631(7) 0.0307(5) Uani 1 1 d . . . H1 H 0.7764 0.5779 0.1629 0.037 Uiso 1 1 calc R . . N2 N 0.9389(5) 0.5822(2) 0.10323(7) 0.0342(6) Uani 1 1 d . . . N3 N 0.5260(5) 0.4284(2) 0.14946(7) 0.0333(6) Uani 1 1 d . . . C1 C 0.8794(7) 0.4559(4) 0.03639(11) 0.0465(8) Uani 1 1 d . . . C2 C 0.7939(6) 0.4858(3) 0.08411(9) 0.0350(7) Uani 1 1 d . . . C3 C 0.5761(6) 0.4036(3) 0.10488(9) 0.0315(6) Uani 1 1 d . . . C4 C 0.4248(7) 0.3043(3) 0.08164(10) 0.0414(8) Uani 1 1 d . . . H4 H 0.4596 0.2865 0.0504 0.050 Uiso 1 1 calc R . . C5 C 0.2266(7) 0.2327(4) 0.10392(11) 0.0447(8) Uani 1 1 d . . . H5 H 0.1245 0.1648 0.0883 0.054 Uiso 1 1 calc R . . C6 C 0.1759(7) 0.2598(3) 0.14911(10) 0.0397(7) Uani 1 1 d . . . H6 H 0.0381 0.2122 0.1652 0.048 Uiso 1 1 calc R . . C7 C 0.3319(6) 0.3581(3) 0.17006(10) 0.0362(7) Uani 1 1 d . . . H7 H 0.2985 0.3768 0.2012 0.043 Uiso 1 1 calc R . . C8 C 1.1520(11) 0.5149(5) -0.02585(13) 0.0801(16) Uani 1 1 d . . . H8A H 1.2466 0.4252 -0.0254 0.096 Uiso 1 1 calc R . . H8B H 1.0004 0.5090 -0.0477 0.096 Uiso 1 1 calc R . . C9 C 1.3313(12) 0.6196(6) -0.03881(15) 0.0866(16) Uani 1 1 d . . . H9A H 1.2312 0.7058 -0.0428 0.130 Uiso 1 1 calc R . . H9B H 1.4189 0.5946 -0.0675 0.130 Uiso 1 1 calc R . . H9C H 1.4690 0.6317 -0.0152 0.130 Uiso 1 1 calc R . . C10 C 1.0648(6) 0.7214(3) 0.16474(9) 0.0295(6) Uani 1 1 d . . . C11 C 1.0198(6) 0.7615(3) 0.20960(9) 0.0324(7) Uani 1 1 d . . . H11 H 0.8828 0.7177 0.2270 0.039 Uiso 1 1 calc R . . C12 C 1.1745(6) 0.8649(3) 0.22887(10) 0.0325(6) Uani 1 1 d . . . H12 H 1.1442 0.8920 0.2595 0.039 Uiso 1 1 calc R . . C13 C 1.3727(6) 0.9282(3) 0.20338(9) 0.0318(6) Uani 1 1 d . . . C14 C 1.4192(7) 0.8880(3) 0.15905(10) 0.0370(7) Uani 1 1 d . . . H14 H 1.5567 0.9318 0.1418 0.044 Uiso 1 1 calc R . . C15 C 1.2669(6) 0.7846(3) 0.13983(10) 0.0355(7) Uani 1 1 d . . . H15 H 1.3007 0.7567 0.1094 0.043 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 Cl1 0.0395(4) 0.0351(4) 0.0459(4) 0.0007(3) -0.0072(4) -0.0032(4) O1 0.0829(19) 0.0897(19) 0.0319(12) -0.0111(12) 0.0171(13) -0.031(2) O2 0.092(2) 0.097(2) 0.0472(15) -0.0400(16) 0.0282(16) -0.034(2) N1 0.0323(13) 0.0361(12) 0.0237(11) -0.0021(10) 0.0018(10) 0.0002(11) N2 0.0358(12) 0.0414(14) 0.0254(11) -0.0021(10) 0.0013(11) 0.0074(13) N3 0.0375(14) 0.0367(13) 0.0257(11) -0.0053(10) 0.0001(10) 0.0032(12) C1 0.0391(19) 0.064(2) 0.0362(17) -0.0077(17) 0.0045(14) -0.0078(18) C2 0.0362(17) 0.0437(17) 0.0251(15) -0.0059(12) -0.0001(13) 0.0025(14) C3 0.0316(15) 0.0339(15) 0.0288(13) -0.0054(11) -0.0028(13) 0.0069(13) C4 0.0434(18) 0.0485(18) 0.0322(15) -0.0125(13) -0.0061(15) 0.0049(17) C5 0.044(2) 0.0448(19) 0.0456(18) -0.0103(16) -0.0082(16) -0.0036(17) C6 0.0386(17) 0.0404(17) 0.0402(17) 0.0003(14) -0.0026(14) 0.0002(15) C7 0.0379(17) 0.0398(17) 0.0310(15) -0.0013(13) -0.0003(13) -0.0007(14) C8 0.101(4) 0.099(3) 0.041(2) -0.017(2) 0.024(2) -0.023(3) C9 0.098(4) 0.109(4) 0.052(2) -0.006(2) 0.029(3) -0.024(3) C10 0.0284(13) 0.0319(14) 0.0282(13) 0.0018(11) -0.0042(13) 0.0050(13) C11 0.0316(17) 0.0361(15) 0.0294(13) 0.0024(12) 0.0017(12) 0.0018(13) C12 0.0330(15) 0.0358(15) 0.0286(13) -0.0007(13) -0.0008(13) 0.0038(13) C13 0.0296(16) 0.0311(15) 0.0347(15) 0.0027(13) -0.0052(11) 0.0019(13) C14 0.0351(16) 0.0421(16) 0.0340(15) 0.0090(12) 0.0029(14) -0.0010(15) C15 0.0329(16) 0.0447(18) 0.0288(14) 0.0015(13) 0.0008(13) -0.0004(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 Cl1 C13 1.742(3) . ? O1 C1 1.318(4) . ? O1 C8 1.479(4) . ? O2 C1 1.188(4) . ? N1 N2 1.328(3) . ? N1 C10 1.398(4) . ? N1 H1 0.8800 . ? N2 C2 1.308(4) . ? N3 C7 1.326(4) . ? N3 C3 1.356(3) . ? C1 C2 1.495(4) . ? C2 C3 1.474(4) . ? C3 C4 1.400(4) . ? C4 C5 1.369(5) . ? C4 H4 0.9500 . ? C5 C6 1.379(4) . ? C5 H5 0.9500 . ? C6 C7 1.374(4) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 C9 1.403(7) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C15 1.384(4) . ? C10 C11 1.394(4) . ? C11 C12 1.385(4) . ? C11 H11 0.9500 . ? C12 C13 1.380(4) . ? C12 H12 0.9500 . ? C13 C14 1.381(4) . ? C14 C15 1.378(4) . ? C14 H14 0.9500 . ? C15 H15 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 C1 O1 C8 113.9(3) . . ? N2 N1 C10 118.6(2) . . ? N2 N1 H1 120.7 . . ? C10 N1 H1 120.7 . . ? C2 N2 N1 121.5(3) . . ? C7 N3 C3 118.9(3) . . ? O2 C1 O1 121.0(3) . . ? O2 C1 C2 126.0(3) . . ? O1 C1 C2 113.0(3) . . ? N2 C2 C3 127.7(3) . . ? N2 C2 C1 112.9(3) . . ? C3 C2 C1 119.4(3) . . ? N3 C3 C4 119.8(3) . . ? N3 C3 C2 116.0(2) . . ? C4 C3 C2 124.2(3) . . ? C5 C4 C3 119.9(3) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C4 C5 C6 119.7(3) . . ? C4 C5 H5 120.2 . . ? C6 C5 H5 120.2 . . ? C7 C6 C5 117.6(3) . . ? C7 C6 H6 121.2 . . ? C5 C6 H6 121.2 . . ? N3 C7 C6 124.1(3) . . ? N3 C7 H7 118.0 . . ? C6 C7 H7 118.0 . . ? C9 C8 O1 107.9(4) . . ? C9 C8 H8A 110.1 . . ? O1 C8 H8A 110.1 . . ? C9 C8 H8B 110.1 . . ? O1 C8 H8B 110.1 . . ? H8A C8 H8B 108.4 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C15 C10 C11 119.5(3) . . ? C15 C10 N1 122.1(2) . . ? C11 C10 N1 118.4(3) . . ? C12 C11 C10 120.2(3) . . ? C12 C11 H11 119.9 . . ? C10 C11 H11 119.9 . . ? C13 C12 C11 119.6(3) . . ? C13 C12 H12 120.2 . . ? C11 C12 H12 120.2 . . ? C12 C13 C14 120.4(3) . . ? C12 C13 Cl1 119.3(2) . . ? C14 C13 Cl1 120.3(2) . . ? C15 C14 C13 120.2(3) . . ? C15 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? C14 C15 C10 120.1(3) . . ? C14 C15 H15 119.9 . . ? C10 C15 H15 119.9 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C10 N1 N2 C2 179.6(3) . . . . ? C8 O1 C1 O2 -2.8(6) . . . . ? C8 O1 C1 C2 175.6(3) . . . . ? N1 N2 C2 C3 -0.1(5) . . . . ? N1 N2 C2 C1 -176.7(3) . . . . ? O2 C1 C2 N2 166.5(4) . . . . ? O1 C1 C2 N2 -11.8(4) . . . . ? O2 C1 C2 C3 -10.4(6) . . . . ? O1 C1 C2 C3 171.4(3) . . . . ? C7 N3 C3 C4 -0.5(4) . . . . ? C7 N3 C3 C2 179.7(3) . . . . ? N2 C2 C3 N3 -2.0(4) . . . . ? C1 C2 C3 N3 174.4(3) . . . . ? N2 C2 C3 C4 178.2(3) . . . . ? C1 C2 C3 C4 -5.4(5) . . . . ? N3 C3 C4 C5 0.1(5) . . . . ? C2 C3 C4 C5 179.9(3) . . . . ? C3 C4 C5 C6 0.5(5) . . . . ? C4 C5 C6 C7 -0.7(5) . . . . ? C3 N3 C7 C6 0.3(4) . . . . ? C5 C6 C7 N3 0.3(5) . . . . ? C1 O1 C8 C9 -179.1(4) . . . . ? N2 N1 C10 C15 -1.4(4) . . . . ? N2 N1 C10 C11 178.3(2) . . . . ? C15 C10 C11 C12 0.7(4) . . . . ? N1 C10 C11 C12 -179.0(3) . . . . ? C10 C11 C12 C13 0.2(4) . . . . ? C11 C12 C13 C14 -0.7(4) . . . . ? C11 C12 C13 Cl1 178.7(2) . . . . ? C12 C13 C14 C15 0.3(5) . . . . ? Cl1 C13 C14 C15 -179.1(2) . . . . ? C13 C14 C15 C10 0.6(5) . . . . ? C11 C10 C15 C14 -1.1(4) . . . . ? N1 C10 C15 C14 178.6(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 N3 0.88 1.95 2.620(3) 131.7 . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.38 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.674 _refine_diff_density_min -0.302 _refine_diff_density_rms 0.050 _contact_Crystallographer_name 'Richard Staples' _contact_Crystallographer_email staples@chemistry.msu.com data_ia2511_0m _database_code_depnum_ccdc_archive 'CCDC 885516' #TrackingRef 'web_deposit_cif_file_3_XinSu_1339039487.4Br.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C15 H14 Br N3 O2' _chemical_formula_sum 'C15 H14 Br N3 O2' _chemical_melting_point ? _exptl_crystal_description needle _exptl_crystal_colour yellow _diffrn_ambient_temperature 173(2) _chemical_formula_weight 348.20 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' Br Br -0.2901 2.4595 '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 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab ' _symmetry_int_tables_number 19 _chemical_absolute_configuration ad loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' _cell_length_a 7.2194(2) _cell_length_b 10.0881(3) _cell_length_c 20.1172(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1465.14(7) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4878 _cell_measurement_theta_min 2.26 _cell_measurement_theta_max 25.32 _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.579 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 2.813 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.4948 _exptl_absorpt_correction_T_max 0.7623 _exptl_absorpt_process_details SADABS _exptl_special_details ; Data was collected using a BRUKER CCD (charge coupled device) based diffractometer equipped with an Oxford low-temperature apparatus operating at 173 K. A suitable crystal was chosen and mounted on a glass fiber or nylon loop using Paratone oil for Mo radiation and Mineral oil for Copper radiation. Data were measured using omega and phi scans of 0.5\% per frame for 30 s. The total number of images were based on results from the program COSMO where redundancy was expected to be 4 and completeness to 0.83\%A to 100%. Cell parameters were retrieved using APEX II software and refined using SAINT on all observed reflections.Data reduction was performed using the SAINT software which corrects for Lp. Scaling and absorption corrections were applied using SADABS6 multi-scan technique, supplied by George Sheldrick. The structures are solved by the direct method using the SHELXS-97 program and refined by least squares method on F2, SHELXL-97, incorporated in SHELXTL-PC V 6.14. All H atoms were placed in calculated positions and refined using a riding model. C-H(aromatic) = 0.94 \%A and Uiso(H) = 1.2Ueq(C) C-H (alaphatic) = 0.99 \%A and Uiso(H) = 1.2Ueq(C) CH2 = 0.98 \%A and Uiso(H) = 1.2Ueq(C) CH3 = 0.97\%A and Uiso(H) = 1.5Ueq(C) N-H = 0.86 (0.92)\%A and Uiso(H) = 1.2 Ueq(N) O-H(alcohol) = 0.85\%Aand Uiso(H) = 1.2Ueq(O) O-H(acid) = 0.82\%A and Uiso(H) = 1.5Ueq(O) ; _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 'Bruker APEX-II CCD' _diffrn_measurement_method '\w,and/f 0.5 deg' _diffrn_detector_area_resol_mean 836.6 _diffrn_reflns_number 7614 _diffrn_reflns_av_R_equivalents 0.0269 _diffrn_reflns_av_sigmaI/netI 0.0419 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 25.34 _reflns_number_total 2644 _reflns_number_gt 2332 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COSMO (BRUKER, V1.61, 2009)' _computing_cell_refinement 'APEX2 (BRUKER, V2010.11-3, 2010)' _computing_data_reduction 'SAINT (BRUKER, V7.68A, 2010)' _computing_structure_solution 'SHELXS (Sheldrick, Acta Cryst. A64 2008, 112-122)' _computing_structure_refinement 'SHELXL (Sheldrick, Acta Cryst. A64 2008, 112-122)' _computing_molecular_graphics 'SHELXTL (Sheldrick, Acta Cryst. A64 2008, 112-122)' _computing_publication_material 'SHELXTL (Sheldrick, Acta Cryst. A64 2008, 112-122)' _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^)+(0.0187P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.000(9) _refine_ls_number_reflns 2644 _refine_ls_number_parameters 191 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0310 _refine_ls_R_factor_gt 0.0247 _refine_ls_wR_factor_ref 0.0556 _refine_ls_wR_factor_gt 0.0538 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.001 _refine_ls_shift/su_max 0.004 _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 Br1 Br 0.65674(4) 0.75135(3) 1.322733(11) 0.04732(10) Uani 1 1 d . . . O1 O 0.4942(2) 1.19574(16) 0.95892(8) 0.0330(4) Uani 1 1 d . . . O2 O 0.3508(2) 1.11698(16) 0.86825(8) 0.0360(4) Uani 1 1 d . . . N1 N 0.5807(3) 0.8349(2) 1.02627(10) 0.0319(5) Uani 1 1 d . . . H1 H 0.6026 0.7673 0.9998 0.038 Uiso 1 1 calc R . . N2 N 0.5326(3) 0.9521(2) 1.00074(9) 0.0289(5) Uani 1 1 d . . . N3 N 0.5903(3) 0.7418(2) 0.90431(9) 0.0327(5) Uani 1 1 d . . . C1 C 0.5228(3) 0.9668(2) 0.93624(11) 0.0285(5) Uani 1 1 d . . . C2 C 0.4481(3) 1.0996(2) 0.91627(12) 0.0279(6) Uani 1 1 d . . . C3 C 0.5676(3) 0.8692(2) 0.88403(13) 0.0283(6) Uani 1 1 d . . . C4 C 0.5909(3) 0.9050(3) 0.81756(12) 0.0316(6) Uani 1 1 d . . . H4 H 0.5788 0.9949 0.8043 0.038 Uiso 1 1 calc R . . C5 C 0.6314(4) 0.8085(3) 0.77158(13) 0.0364(7) Uani 1 1 d . . . H5 H 0.6458 0.8312 0.7260 0.044 Uiso 1 1 calc R . . C6 C 0.6511(4) 0.6795(3) 0.79171(13) 0.0365(6) Uani 1 1 d . . . H6 H 0.6777 0.6115 0.7605 0.044 Uiso 1 1 calc R . . C7 C 0.6314(4) 0.6505(3) 0.85822(13) 0.0383(7) Uani 1 1 d . . . H7 H 0.6477 0.5613 0.8721 0.046 Uiso 1 1 calc R . . C8 C 0.4132(4) 1.3253(2) 0.94528(13) 0.0337(6) Uani 1 1 d . . . H8A H 0.2769 1.3217 0.9504 0.040 Uiso 1 1 calc R . . H8B H 0.4422 1.3533 0.8993 0.040 Uiso 1 1 calc R . . C9 C 0.4945(4) 1.4208(3) 0.99402(12) 0.0444(7) Uani 1 1 d . . . H9A H 0.4652 1.3919 1.0393 0.067 Uiso 1 1 calc R . . H9B H 0.4425 1.5092 0.9864 0.067 Uiso 1 1 calc R . . H9C H 0.6293 1.4239 0.9883 0.067 Uiso 1 1 calc R . . C10 C 0.5962(4) 0.8196(3) 1.09482(12) 0.0273(6) Uani 1 1 d . . . C11 C 0.6142(4) 0.6917(3) 1.11976(13) 0.0316(6) Uani 1 1 d . . . H11 H 0.6129 0.6180 1.0904 0.038 Uiso 1 1 calc R . . C12 C 0.6339(3) 0.6719(2) 1.18759(12) 0.0310(6) Uani 1 1 d . . . H12 H 0.6481 0.5849 1.2049 0.037 Uiso 1 1 calc R . . C13 C 0.6326(3) 0.7788(2) 1.22932(11) 0.0314(6) Uani 1 1 d . . . C14 C 0.6130(3) 0.9066(3) 1.20552(12) 0.0318(6) Uani 1 1 d . . . H14 H 0.6115 0.9795 1.2354 0.038 Uiso 1 1 calc R . . C15 C 0.5955(3) 0.9277(2) 1.13784(12) 0.0310(6) Uani 1 1 d . . . H15 H 0.5832 1.0151 1.1209 0.037 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 Br1 0.06123(17) 0.05241(18) 0.02833(14) 0.00815(17) -0.00418(13) -0.0105(2) O1 0.0450(10) 0.0242(9) 0.0299(9) -0.0011(8) -0.0082(9) 0.0058(8) O2 0.0454(10) 0.0332(10) 0.0292(9) 0.0012(8) -0.0068(9) 0.0042(9) N1 0.0460(12) 0.0238(12) 0.0260(11) -0.0011(10) 0.0007(9) 0.0081(10) N2 0.0326(11) 0.0263(12) 0.0276(12) 0.0018(9) -0.0025(9) 0.0019(10) N3 0.0371(10) 0.0275(11) 0.0336(10) -0.0042(12) 0.0020(8) 0.0022(13) C1 0.0299(12) 0.0299(13) 0.0255(13) 0.0006(11) -0.0007(11) -0.0021(11) C2 0.0314(13) 0.0268(13) 0.0254(13) -0.0001(12) 0.0037(11) -0.0006(12) C3 0.0235(13) 0.0311(15) 0.0302(14) -0.0019(12) -0.0023(11) -0.0013(12) C4 0.0311(12) 0.0365(14) 0.0273(13) -0.0023(13) -0.0008(12) 0.0016(12) C5 0.0327(15) 0.0496(17) 0.0269(14) -0.0060(13) 0.0026(12) -0.0015(15) C6 0.0348(14) 0.0375(16) 0.0373(16) -0.0145(14) 0.0021(15) -0.0007(16) C7 0.0417(16) 0.0304(14) 0.0428(17) -0.0062(14) 0.0002(15) 0.0019(14) C8 0.0399(15) 0.0244(14) 0.0369(15) 0.0019(13) -0.0023(13) 0.0020(13) C9 0.0621(17) 0.0300(16) 0.0411(17) -0.0019(13) -0.0042(15) 0.0032(14) C10 0.0274(14) 0.0258(13) 0.0287(14) 0.0025(12) -0.0013(11) 0.0014(12) C11 0.0354(15) 0.0283(13) 0.0309(14) -0.0047(12) 0.0010(12) 0.0033(13) C12 0.0333(13) 0.0263(14) 0.0333(14) 0.0059(12) -0.0009(13) 0.0010(12) C13 0.0284(12) 0.0413(18) 0.0246(12) 0.0056(11) -0.0002(10) -0.0016(13) C14 0.0337(14) 0.0304(14) 0.0315(14) -0.0036(12) -0.0012(12) -0.0032(12) C15 0.0376(14) 0.0235(13) 0.0318(14) 0.0013(12) -0.0023(11) 0.0030(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C13 1.907(2) . ? O1 C2 1.337(3) . ? O1 C8 1.458(3) . ? O2 C2 1.207(3) . ? N1 N2 1.335(3) . ? N1 C10 1.392(3) . ? N1 H1 0.8800 . ? N2 C1 1.308(3) . ? N3 C7 1.340(3) . ? N3 C3 1.358(3) . ? C1 C3 1.476(3) . ? C1 C2 1.499(3) . ? C3 C4 1.395(3) . ? C4 C5 1.374(3) . ? C4 H4 0.9500 . ? C5 C6 1.370(4) . ? C5 H5 0.9500 . ? C6 C7 1.377(3) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 C9 1.495(3) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C11 1.390(3) . ? C10 C15 1.392(3) . ? C11 C12 1.387(3) . ? C11 H11 0.9500 . ? C12 C13 1.367(3) . ? C12 H12 0.9500 . ? C13 C14 1.383(3) . ? C14 C15 1.384(3) . ? C14 H14 0.9500 . ? C15 H15 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 C2 O1 C8 115.43(18) . . ? N2 N1 C10 120.0(2) . . ? N2 N1 H1 120.0 . . ? C10 N1 H1 120.0 . . ? C1 N2 N1 119.8(2) . . ? C7 N3 C3 118.0(2) . . ? N2 C1 C3 128.2(2) . . ? N2 C1 C2 112.8(2) . . ? C3 C1 C2 119.0(2) . . ? O2 C2 O1 123.6(2) . . ? O2 C2 C1 123.6(2) . . ? O1 C2 C1 112.7(2) . . ? N3 C3 C4 121.2(2) . . ? N3 C3 C1 116.4(2) . . ? C4 C3 C1 122.4(2) . . ? C5 C4 C3 119.2(2) . . ? C5 C4 H4 120.4 . . ? C3 C4 H4 120.4 . . ? C6 C5 C4 119.7(2) . . ? C6 C5 H5 120.1 . . ? C4 C5 H5 120.1 . . ? C5 C6 C7 118.6(3) . . ? C5 C6 H6 120.7 . . ? C7 C6 H6 120.7 . . ? N3 C7 C6 123.3(3) . . ? N3 C7 H7 118.3 . . ? C6 C7 H7 118.3 . . ? O1 C8 C9 107.24(19) . . ? O1 C8 H8A 110.3 . . ? C9 C8 H8A 110.3 . . ? O1 C8 H8B 110.3 . . ? C9 C8 H8B 110.3 . . ? H8A C8 H8B 108.5 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C10 N1 117.9(2) . . ? C11 C10 C15 120.2(2) . . ? N1 C10 C15 121.9(2) . . ? C12 C11 C10 119.9(2) . . ? C12 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? C13 C12 C11 119.3(2) . . ? C13 C12 H12 120.3 . . ? C11 C12 H12 120.3 . . ? C12 C13 C14 121.6(2) . . ? C12 C13 Br1 119.33(17) . . ? C14 C13 Br1 119.08(19) . . ? C13 C14 C15 119.6(2) . . ? C13 C14 H14 120.2 . . ? C15 C14 H14 120.2 . . ? C14 C15 C10 119.4(2) . . ? C14 C15 H15 120.3 . . ? C10 C15 H15 120.3 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C10 N1 N2 C1 178.3(2) . . . . ? N1 N2 C1 C3 -3.2(4) . . . . ? N1 N2 C1 C2 174.01(19) . . . . ? C8 O1 C2 O2 2.1(3) . . . . ? C8 O1 C2 C1 -175.16(19) . . . . ? N2 C1 C2 O2 -144.8(2) . . . . ? C3 C1 C2 O2 32.7(3) . . . . ? N2 C1 C2 O1 32.5(3) . . . . ? C3 C1 C2 O1 -150.0(2) . . . . ? C7 N3 C3 C4 -1.6(4) . . . . ? C7 N3 C3 C1 -179.9(2) . . . . ? N2 C1 C3 N3 12.8(4) . . . . ? C2 C1 C3 N3 -164.3(2) . . . . ? N2 C1 C3 C4 -165.5(2) . . . . ? C2 C1 C3 C4 17.5(3) . . . . ? N3 C3 C4 C5 2.2(4) . . . . ? C1 C3 C4 C5 -179.6(2) . . . . ? C3 C4 C5 C6 -1.0(4) . . . . ? C4 C5 C6 C7 -0.7(5) . . . . ? C3 N3 C7 C6 -0.2(4) . . . . ? C5 C6 C7 N3 1.3(5) . . . . ? C2 O1 C8 C9 -174.8(2) . . . . ? N2 N1 C10 C11 168.9(2) . . . . ? N2 N1 C10 C15 -11.6(4) . . . . ? N1 C10 C11 C12 178.7(2) . . . . ? C15 C10 C11 C12 -0.8(4) . . . . ? C10 C11 C12 C13 1.0(4) . . . . ? C11 C12 C13 C14 -0.3(4) . . . . ? C11 C12 C13 Br1 179.26(19) . . . . ? C12 C13 C14 C15 -0.5(4) . . . . ? Br1 C13 C14 C15 179.94(18) . . . . ? C13 C14 C15 C10 0.6(4) . . . . ? C11 C10 C15 C14 0.0(4) . . . . ? N1 C10 C15 C14 -179.5(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 N3 0.88 1.94 2.628(3) 134.0 . _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.34 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.200 _refine_diff_density_min -0.310 _refine_diff_density_rms 0.042 _contact_Crystallographer_name 'Richard Staples' _contact_Crystallographer_email staples@chemistry.msu.com data_ia3111_0m _database_code_depnum_ccdc_archive 'CCDC 885517' #TrackingRef 'web_deposit_cif_file_4_XinSu_1339039487.4NO2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C15 H14 N4 O4' _chemical_formula_sum 'C15 H14 N4 O4' _chemical_melting_point ? _exptl_crystal_description needle _exptl_crystal_colour yellow _diffrn_ambient_temperature 173(2) _chemical_formula_weight 314.30 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab ' _symmetry_int_tables_number 61 _chemical_absolute_configuration ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' 'x-1/2, y, -z-1/2' _cell_length_a 6.6841(5) _cell_length_b 19.9101(15) _cell_length_c 22.7748(17) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3030.9(4) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 7659 _cell_measurement_theta_min 2.23 _cell_measurement_theta_max 26.31 _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.378 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1312 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9542 _exptl_absorpt_correction_T_max 0.9920 _exptl_absorpt_process_details SADABS _exptl_special_details ; Data was collected using a BRUKER CCD (charge coupled device) based diffractometer equipped with an Oxford low-temperature apparatus operating at 173 K. A suitable crystal was chosen and mounted on a glass fiber or nylon loop using Paratone oil for Mo radiation and Mineral oil for Copper radiation. Data were measured using omega and Phi scans of 0.5\% per frame for 30 s. The total number of images were based on results from the program COSMO where redundancy was expected to be 4.0 and completeness to 0.83\%A to 100%. Cell parameters were retrieved using APEX II software and refined using SAINT on all observed reflections. Data reduction was performed using the SAINT software which corrects for Lp. Scaling and absorption corrections were applied using SADABS6 multi-scan technique, supplied by George Sheldrick. The structures are solved by the direct method using the SHELXS-97 program and refined by least squares method on F2, SHELXL-97, incorporated in SHELXTL-PC V 6.14. All H atoms were found by difference Fourier methods and refined isotrpically. ; _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 'Bruker APEX-II CCD' _diffrn_measurement_method '\w,and/f 0.5 deg' _diffrn_detector_area_resol_mean 836.6 _diffrn_reflns_number 24984 _diffrn_reflns_av_R_equivalents 0.0449 _diffrn_reflns_av_sigmaI/netI 0.0262 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 26.46 _reflns_number_total 3134 _reflns_number_gt 2319 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COSMO (BRUKER, V1.61, 2009)' _computing_cell_refinement 'APEX2 (BRUKER, V2010.11-3, 2010)' _computing_data_reduction 'SAINT (BRUKER, V7.68A, 2010)' _computing_structure_solution 'SHELXS (Sheldrick, Acta Cryst. A64 2008, 112-122)' _computing_structure_refinement 'SHELXL (Sheldrick, Acta Cryst. A64 2008, 112-122)' _computing_molecular_graphics 'SHELXTL (Sheldrick, Acta Cryst. A64 2008, 112-122)' _computing_publication_material 'SHELXTL (Sheldrick, Acta Cryst. A64 2008, 112-122)' _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^)+(0.0435P)^2^+0.7272P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3134 _refine_ls_number_parameters 264 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0573 _refine_ls_R_factor_gt 0.0360 _refine_ls_wR_factor_ref 0.0954 _refine_ls_wR_factor_gt 0.0836 _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_restrained_S_all 1.011 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.16227(16) 1.06306(5) 0.68916(4) 0.0356(3) Uani 1 1 d . . . O2 O 0.16781(19) 1.10544(5) 0.77972(5) 0.0455(3) Uani 1 1 d . . . O3 O -0.0913(2) 0.73650(6) 0.49052(5) 0.0535(3) Uani 1 1 d . . . O4 O -0.20912(19) 0.66088(6) 0.54898(5) 0.0497(3) Uani 1 1 d . . . N1 N 0.01054(18) 0.88407(6) 0.73245(5) 0.0292(3) Uani 1 1 d . . . H1 H -0.016(3) 0.8722(9) 0.7709(8) 0.051(5) Uiso 1 1 d . . . N2 N 0.06571(17) 0.94756(6) 0.72335(5) 0.0272(3) Uani 1 1 d . . . N3 N 0.01735(18) 0.91107(6) 0.84425(5) 0.0330(3) Uani 1 1 d . . . N4 N -0.1356(2) 0.71660(6) 0.53987(6) 0.0379(3) Uani 1 1 d . . . C1 C 0.1042(2) 0.98777(7) 0.76722(6) 0.0261(3) Uani 1 1 d . . . C2 C 0.1494(2) 1.05782(7) 0.74740(6) 0.0289(3) Uani 1 1 d . . . C3 C 0.1870(3) 1.13058(9) 0.66629(8) 0.0423(4) Uani 1 1 d . . . H3A H 0.308(3) 1.1507(9) 0.6843(7) 0.046(5) Uiso 1 1 d . . . H3B H 0.070(3) 1.1575(9) 0.6782(7) 0.049(5) Uiso 1 1 d . . . C4 C 0.2033(4) 1.12423(12) 0.60096(8) 0.0551(5) Uani 1 1 d . . . H4A H 0.330(4) 1.0972(11) 0.5902(9) 0.083(7) Uiso 1 1 d . . . H4B H 0.215(3) 1.1689(11) 0.5846(9) 0.068(6) Uiso 1 1 d . . . H4C H 0.087(4) 1.1037(11) 0.5838(9) 0.075(7) Uiso 1 1 d . . . C5 C 0.1022(2) 0.97076(7) 0.83056(6) 0.0282(3) Uani 1 1 d . . . C6 C 0.1865(3) 1.01146(9) 0.87397(6) 0.0369(4) Uani 1 1 d . . . H6 H 0.249(3) 1.0536(10) 0.8627(8) 0.052(5) Uiso 1 1 d . . . C7 C 0.1777(3) 0.99089(9) 0.93177(7) 0.0448(4) Uani 1 1 d . . . H7 H 0.238(3) 1.0198(9) 0.9620(7) 0.051(5) Uiso 1 1 d . . . C8 C 0.0877(3) 0.93072(9) 0.94572(7) 0.0439(4) Uani 1 1 d . . . H8 H 0.076(2) 0.9151(8) 0.9860(7) 0.042(4) Uiso 1 1 d . . . C9 C 0.0116(2) 0.89247(9) 0.90067(7) 0.0394(4) Uani 1 1 d . . . H9 H -0.048(2) 0.8490(9) 0.9075(7) 0.039(4) Uiso 1 1 d . . . C10 C -0.0241(2) 0.84344(7) 0.68399(6) 0.0275(3) Uani 1 1 d . . . C11 C 0.0197(2) 0.86514(7) 0.62720(6) 0.0291(3) Uani 1 1 d . . . H11 H 0.073(2) 0.9092(8) 0.6211(6) 0.028(4) Uiso 1 1 d . . . C12 C -0.0172(2) 0.82367(7) 0.58004(7) 0.0312(3) Uani 1 1 d . . . H12 H 0.016(2) 0.8376(8) 0.5410(7) 0.038(4) Uiso 1 1 d . . . C13 C -0.0988(2) 0.76070(7) 0.58976(6) 0.0308(3) Uani 1 1 d . . . C14 C -0.1424(2) 0.73813(8) 0.64592(7) 0.0346(4) Uani 1 1 d . . . H14 H -0.194(2) 0.6951(9) 0.6517(7) 0.041(5) Uiso 1 1 d . . . C15 C -0.1046(2) 0.77945(7) 0.69312(7) 0.0331(3) Uani 1 1 d . . . H15 H -0.137(2) 0.7651(8) 0.7337(7) 0.039(4) 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 0.0471(7) 0.0306(6) 0.0291(5) 0.0030(4) 0.0027(5) -0.0042(5) O2 0.0679(8) 0.0301(6) 0.0386(6) -0.0063(5) -0.0014(5) -0.0047(6) O3 0.0777(9) 0.0471(8) 0.0357(7) -0.0087(5) 0.0010(6) -0.0082(7) O4 0.0656(8) 0.0272(6) 0.0564(7) -0.0056(5) -0.0127(6) -0.0061(6) N1 0.0337(7) 0.0257(7) 0.0281(6) 0.0015(5) -0.0001(5) -0.0013(5) N2 0.0251(6) 0.0257(6) 0.0307(6) -0.0005(5) -0.0001(5) 0.0008(5) N3 0.0302(7) 0.0397(8) 0.0292(6) 0.0050(5) 0.0007(5) 0.0009(6) N4 0.0424(8) 0.0283(7) 0.0431(8) -0.0056(6) -0.0074(6) 0.0024(6) C1 0.0227(7) 0.0287(8) 0.0267(7) -0.0012(6) 0.0007(5) 0.0026(6) C2 0.0263(7) 0.0303(8) 0.0300(7) -0.0022(6) -0.0002(6) 0.0019(6) C3 0.0466(10) 0.0337(9) 0.0467(10) 0.0122(7) -0.0027(8) -0.0055(8) C4 0.0576(13) 0.0618(13) 0.0459(11) 0.0227(10) -0.0011(10) -0.0062(11) C5 0.0254(7) 0.0313(8) 0.0279(7) -0.0007(6) 0.0029(6) 0.0048(6) C6 0.0429(9) 0.0379(9) 0.0298(8) -0.0030(7) -0.0004(7) 0.0043(8) C7 0.0576(11) 0.0480(11) 0.0288(8) -0.0066(7) -0.0023(8) 0.0085(9) C8 0.0487(10) 0.0564(11) 0.0265(8) 0.0045(7) 0.0052(7) 0.0140(9) C9 0.0349(9) 0.0483(10) 0.0351(9) 0.0104(8) 0.0036(7) 0.0023(8) C10 0.0251(7) 0.0273(8) 0.0303(7) -0.0014(6) -0.0028(6) 0.0029(6) C11 0.0297(8) 0.0236(8) 0.0340(8) -0.0003(6) 0.0022(6) -0.0010(6) C12 0.0329(8) 0.0289(8) 0.0318(8) -0.0004(6) 0.0024(6) 0.0007(6) C13 0.0325(8) 0.0250(7) 0.0349(8) -0.0048(6) -0.0035(6) 0.0035(6) C14 0.0387(9) 0.0221(8) 0.0429(9) 0.0033(6) -0.0047(7) -0.0019(7) C15 0.0389(8) 0.0284(8) 0.0321(8) 0.0051(6) -0.0014(7) -0.0012(7) _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 C2 1.3333(17) . ? O1 C3 1.4511(19) . ? O2 C2 1.2066(16) . ? O3 N4 1.2280(17) . ? O4 N4 1.2309(17) . ? N1 N2 1.3330(16) . ? N1 C10 1.3878(18) . ? N1 H1 0.923(17) . ? N2 C1 1.3058(17) . ? N3 C9 1.3378(19) . ? N3 C5 1.3531(19) . ? N4 C13 1.4571(18) . ? C1 C5 1.4818(18) . ? C1 C2 1.4969(19) . ? C3 C4 1.497(3) . ? C3 H3A 0.993(18) . ? C3 H3B 0.984(19) . ? C4 H4A 1.03(3) . ? C4 H4B 0.97(2) . ? C4 H4C 0.96(2) . ? C5 C6 1.397(2) . ? C6 C7 1.380(2) . ? C6 H6 0.972(19) . ? C7 C8 1.377(3) . ? C7 H7 0.984(18) . ? C8 C9 1.375(2) . ? C8 H8 0.973(17) . ? C9 H9 0.966(17) . ? C10 C11 1.3949(19) . ? C10 C15 1.398(2) . ? C11 C12 1.377(2) . ? C11 H11 0.958(16) . ? C12 C13 1.385(2) . ? C12 H12 0.957(16) . ? C13 C14 1.387(2) . ? C14 C15 1.377(2) . ? C14 H14 0.934(17) . ? C15 H15 0.991(15) . ? 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 C2 O1 C3 115.91(12) . . ? N2 N1 C10 118.38(12) . . ? N2 N1 H1 116.3(11) . . ? C10 N1 H1 124.9(11) . . ? C1 N2 N1 121.12(12) . . ? C9 N3 C5 118.46(14) . . ? O3 N4 O4 122.78(13) . . ? O3 N4 C13 118.59(13) . . ? O4 N4 C13 118.63(13) . . ? N2 C1 C5 127.09(13) . . ? N2 C1 C2 112.35(11) . . ? C5 C1 C2 120.55(12) . . ? O2 C2 O1 122.60(13) . . ? O2 C2 C1 124.67(13) . . ? O1 C2 C1 112.70(12) . . ? O1 C3 C4 106.67(15) . . ? O1 C3 H3A 108.6(10) . . ? C4 C3 H3A 112.6(10) . . ? O1 C3 H3B 108.4(10) . . ? C4 C3 H3B 112.2(10) . . ? H3A C3 H3B 108.2(14) . . ? C3 C4 H4A 109.8(12) . . ? C3 C4 H4B 108.2(12) . . ? H4A C4 H4B 108.8(18) . . ? C3 C4 H4C 112.4(13) . . ? H4A C4 H4C 110.1(18) . . ? H4B C4 H4C 107.4(18) . . ? N3 C5 C6 121.02(13) . . ? N3 C5 C1 115.39(12) . . ? C6 C5 C1 123.56(14) . . ? C7 C6 C5 119.06(16) . . ? C7 C6 H6 121.8(11) . . ? C5 C6 H6 119.1(10) . . ? C8 C7 C6 119.79(17) . . ? C8 C7 H7 121.8(10) . . ? C6 C7 H7 118.4(10) . . ? C9 C8 C7 118.09(16) . . ? C9 C8 H8 119.8(10) . . ? C7 C8 H8 122.1(10) . . ? N3 C9 C8 123.55(17) . . ? N3 C9 H9 114.5(9) . . ? C8 C9 H9 122.0(9) . . ? N1 C10 C11 121.45(13) . . ? N1 C10 C15 118.49(13) . . ? C11 C10 C15 120.06(13) . . ? C12 C11 C10 119.98(14) . . ? C12 C11 H11 120.2(8) . . ? C10 C11 H11 119.8(8) . . ? C11 C12 C13 119.26(14) . . ? C11 C12 H12 120.6(10) . . ? C13 C12 H12 120.1(10) . . ? C12 C13 C14 121.58(14) . . ? C12 C13 N4 119.17(13) . . ? C14 C13 N4 119.24(13) . . ? C15 C14 C13 119.19(14) . . ? C15 C14 H14 120.5(10) . . ? C13 C14 H14 120.3(10) . . ? C14 C15 C10 119.93(14) . . ? C14 C15 H15 121.0(9) . . ? C10 C15 H15 119.0(9) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C10 N1 N2 C1 -178.64(12) . . . . ? N1 N2 C1 C5 2.6(2) . . . . ? N1 N2 C1 C2 -176.04(12) . . . . ? C3 O1 C2 O2 -3.8(2) . . . . ? C3 O1 C2 C1 174.38(13) . . . . ? N2 C1 C2 O2 171.44(14) . . . . ? C5 C1 C2 O2 -7.3(2) . . . . ? N2 C1 C2 O1 -6.74(17) . . . . ? C5 C1 C2 O1 174.49(12) . . . . ? C2 O1 C3 C4 178.52(15) . . . . ? C9 N3 C5 C6 1.6(2) . . . . ? C9 N3 C5 C1 179.63(13) . . . . ? N2 C1 C5 N3 -12.7(2) . . . . ? C2 C1 C5 N3 165.91(12) . . . . ? N2 C1 C5 C6 165.35(14) . . . . ? C2 C1 C5 C6 -16.1(2) . . . . ? N3 C5 C6 C7 -1.7(2) . . . . ? C1 C5 C6 C7 -179.64(14) . . . . ? C5 C6 C7 C8 0.4(3) . . . . ? C6 C7 C8 C9 1.0(3) . . . . ? C5 N3 C9 C8 -0.1(2) . . . . ? C7 C8 C9 N3 -1.2(3) . . . . ? N2 N1 C10 C11 7.5(2) . . . . ? N2 N1 C10 C15 -172.53(13) . . . . ? N1 C10 C11 C12 -179.74(13) . . . . ? C15 C10 C11 C12 0.3(2) . . . . ? C10 C11 C12 C13 0.3(2) . . . . ? C11 C12 C13 C14 -0.6(2) . . . . ? C11 C12 C13 N4 -179.30(13) . . . . ? O3 N4 C13 C12 0.7(2) . . . . ? O4 N4 C13 C12 -179.62(14) . . . . ? O3 N4 C13 C14 -178.07(14) . . . . ? O4 N4 C13 C14 1.7(2) . . . . ? C12 C13 C14 C15 0.3(2) . . . . ? N4 C13 C14 C15 178.99(14) . . . . ? C13 C14 C15 C10 0.3(2) . . . . ? N1 C10 C15 C14 179.42(14) . . . . ? C11 C10 C15 C14 -0.6(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 N3 0.923(17) 1.855(18) 2.6028(17) 136.3(15) . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.46 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.162 _refine_diff_density_min -0.187 _refine_diff_density_rms 0.036 _contact_Crystallographer_email staples@chemistry.msu.com