data_16srv052 _audit_creation_date 2016-02-13 _audit_creation_method ; Olex2 1.2-beta (compiled 2015.11.10 svn.r3248 for OlexSys, GUI svn.r5133) ; _publ_contact_author_address ? _publ_contact_author_email ? _publ_contact_author_name 'Batsanov, Andrei S.' _publ_contact_author_phone ? _publ_section_references ; Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H. (2009), J. Appl. Cryst. 42, 339-341. Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122. Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8. ; _chemical_name_common ? _chemical_name_systematic ? _chemical_formula_moiety 'C8 H9 N3' _chemical_formula_sum 'C8 H9 N3' _chemical_formula_weight 147.18 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _space_group_crystal_system 'orthorhombic' _space_group_IT_number 62 _space_group_name_H-M_alt 'P n m a' _space_group_name_Hall '-P 2ac 2n' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z+1/2' '-x, y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z-1/2' 'x, -y-1/2, z' _cell_length_a 10.5874(4) _cell_length_b 6.6852(3) _cell_length_c 10.9744(4) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 776.76(5) _cell_formula_units_Z 4 _cell_measurement_reflns_used 9981 _cell_measurement_temperature 120 _cell_measurement_theta_max 32.73 _cell_measurement_theta_min 2.67 _shelx_estimated_absorpt_T_max 0.985 _shelx_estimated_absorpt_T_min 0.965 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 0.9556 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2014/4 (Bruker,2014/4) was used for absorption correction. wR2(int) was 0.1310 before and 0.0511 after correction. The Ratio of minimum to maximum transmission is 0.9556. The \l/2 correction factor is Not present. ; loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 1.00 -2.00 1.00 0.1750 -1.00 2.00 -1.00 0.1790 -1.00 0.00 -1.00 0.0870 1.00 0.00 1.00 0.0970 -1.00 0.00 1.00 0.1310 1.00 0.00 -1.00 0.1550 0.00 0.00 -1.00 0.1100 0.00 0.00 1.00 0.1180 -1.00 -1.00 -1.00 0.1860 1.00 1.00 1.00 0.2010 _exptl_absorpt_special_details ? _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.259 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_description plate _exptl_crystal_F_000 312 _exptl_crystal_size_max 0.439 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.194 _exptl_special_details ; Data were collected in shutterless mode. Full sphere of reciprocal space was nominally covered by 4 runs of narrow-frame \w-scans (scan width 0.5\%, 5s exposure), every run at a different \f angle. Two runs of \f-scans (scan width 1\%, 1s exposure) were used for scaling overflowing intensities. Crystal to detector distance 3.49 cm. ; _exptl_transmission_factor_max ? _exptl_transmission_factor_min ? _diffrn_reflns_av_R_equivalents 0.0326 _diffrn_reflns_av_unetI/netI 0.0170 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 18939 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 32.780 _diffrn_reflns_theta_min 2.673 _diffrn_ambient_temperature 120 _diffrn_detector_area_resol_mean ? _diffrn_detector_type 'Bruker PHOTON 100 CMOS' _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device '3-circle area detector diffractometer' _diffrn_measurement_device_type 'Bruker D8 Venture' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator 'focusing mirrors' _diffrn_radiation_probe X-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'ImuS microsource' _diffrn_standards_number 0 _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 1318 _reflns_number_total 1542 _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _reflns_threshold_expression 'I > 2\s(I)' _computing.bruker_data_scaling 'SADABS V2012/1 (Bruker AXS Inc.)' _computing_cell_refinement 'SAINT v8.34A (Bruker, 2013)' _computing_data_collection 'APEX2 v.2013.4_1 (Bruker, 2013)' _computing_data_reduction 'SAINT v8.34A (Bruker, 2013)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL 2014/7 (Sheldrick, 2015)' _computing_structure_solution 'ShelXS 2013/1 (Sheldrick, 2008)' _refine_diff_density_max 0.448 _refine_diff_density_min -0.300 _refine_diff_density_rms 0.055 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 81 _refine_ls_number_reflns 1542 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0506 _refine_ls_R_factor_gt 0.0428 _refine_ls_restrained_S_all 1.077 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0920P)^2^+0.0450P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1266 _refine_ls_wR_factor_ref 0.1331 _refine_special_details ; Methyl H atoms - refall, other H atoms - riding model (constr). ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups 2.a Aromatic/amide H refined with riding coordinates: C3(H3), C5(H5), C6(H6) ; _atom_sites_solution_hydrogens mixed _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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group N1 N -0.06870(9) 0.2500 0.68032(8) 0.0239(2) Uani 1 2 d S T P . . N2 N -0.31472(9) 0.2500 0.48246(9) 0.0266(2) Uani 1 2 d S T P . . N3 N 0.23937(8) 0.2500 0.43685(9) 0.0241(2) Uani 1 2 d S T P . . C1 C -0.21165(9) 0.2500 0.51626(9) 0.0200(2) Uani 1 2 d S T P . . C2 C -0.08199(9) 0.2500 0.55855(9) 0.0172(2) Uani 1 2 d S T P . . C3 C 0.01411(9) 0.2500 0.47341(8) 0.0166(2) Uani 1 2 d S T P . . H3 H -0.0045 0.2500 0.3887 0.020 Uiso 1 2 calc RS T P . . C4 C 0.14066(8) 0.2500 0.51465(9) 0.0173(2) Uani 1 2 d S T P . . C5 C 0.15713(9) 0.2500 0.64270(9) 0.0219(2) Uani 1 2 d S T P . . H5 H 0.2396 0.2500 0.6767 0.026 Uiso 1 2 calc RS T P . . C6 C 0.05273(10) 0.2500 0.71764(9) 0.0262(2) Uani 1 2 d S T P . . H6 H 0.0675 0.2500 0.8030 0.031 Uiso 1 2 calc RS T P . . C7 C 0.21878(11) 0.2500 0.30591(11) 0.0273(2) Uani 1 2 d S T P . . H7A H 0.1685(10) 0.1348(18) 0.2823(12) 0.042(3) Uiso 1 1 d . . . . . H7B H 0.2945(19) 0.2500 0.2657(18) 0.054(6) Uiso 1 2 d S T P . . C8 C 0.36851(10) 0.2500 0.48252(13) 0.0302(3) Uani 1 2 d S T P . . H8A H 0.3859(12) 0.1338(17) 0.5281(10) 0.038(3) Uiso 1 1 d . . . . . H8B H 0.423(3) 0.2500 0.421(2) 0.078(7) Uiso 1 2 d S T P . . 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 N1 0.0185(4) 0.0343(5) 0.0189(4) 0.000 0.0006(3) 0.000 N2 0.0159(4) 0.0346(5) 0.0294(5) 0.000 -0.0004(3) 0.000 N3 0.0131(3) 0.0348(5) 0.0245(4) 0.000 0.0021(3) 0.000 C1 0.0156(4) 0.0225(4) 0.0219(5) 0.000 0.0012(3) 0.000 C2 0.0133(4) 0.0185(4) 0.0198(4) 0.000 -0.0004(3) 0.000 C3 0.0132(4) 0.0182(4) 0.0184(4) 0.000 -0.0008(3) 0.000 C4 0.0129(4) 0.0178(4) 0.0212(4) 0.000 -0.0002(3) 0.000 C5 0.0168(4) 0.0272(5) 0.0217(4) 0.000 -0.0046(3) 0.000 C6 0.0217(5) 0.0390(6) 0.0179(4) 0.000 -0.0024(4) 0.000 C7 0.0227(5) 0.0352(6) 0.0240(5) 0.000 0.0074(4) 0.000 C8 0.0124(4) 0.0362(6) 0.0420(6) 0.000 -0.0010(4) 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 N1 C2 1.3437(13) . ? N1 C6 1.3493(13) . ? N2 C1 1.1526(13) . ? N3 C4 1.3494(13) . ? N3 C7 1.4534(15) . ? N3 C8 1.4563(14) . ? C1 C2 1.4491(13) . ? C2 C3 1.3814(13) . ? C3 C4 1.4142(12) . ? C4 C5 1.4161(14) . ? C5 C6 1.3777(14) . ? 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 N1 C6 113.68(9) . . ? C4 N3 C7 120.62(9) . . ? C4 N3 C8 120.62(9) . . ? C7 N3 C8 118.75(9) . . ? N2 C1 C2 179.91(11) . . ? N1 C2 C1 114.69(8) . . ? N1 C2 C3 126.55(9) . . ? C3 C2 C1 118.75(9) . . ? C2 C3 C4 118.77(8) . . ? N3 C4 C3 122.09(9) . . ? N3 C4 C5 122.18(9) . . ? C3 C4 C5 115.73(8) . . ? C6 C5 C4 119.58(9) . . ? N1 C6 C5 125.68(9) . . ? _shelx_SHELXL_version_number '2014/7' _iucr_refine_instructions_details ; 16srv052.res created by SHELXL-2014/7 TITL 16srv052 in Pnma #62 REM reset to Pnma #62 CELL 0.71073 10.5874 6.6852 10.9744 90 90 90 ZERR 4 0.0004 0.0003 0.0004 0 0 0 LATT 1 SYMM 0.5-X,-Y,0.5+Z SYMM 0.5+X,0.5-Y,0.5-Z SYMM -X,0.5+Y,-Z SFAC C H N UNIT 32 36 12 L.S. 7 PLAN 7 SIZE 0.194 0.31 0.439 TEMP -153.15 BOND fmap 2 acta REM REM REM WGHT 0.092000 0.045000 FVAR 0.32578 N1 3 -0.068700 0.250000 0.680319 10.50000 0.01845 0.03434 = 0.01895 0.00000 0.00057 0.00000 N2 3 -0.314716 0.250000 0.482459 10.50000 0.01587 0.03456 = 0.02935 0.00000 -0.00044 0.00000 N3 3 0.239366 0.250000 0.436855 10.50000 0.01305 0.03480 = 0.02448 0.00000 0.00205 0.00000 C1 1 -0.211648 0.250000 0.516261 10.50000 0.01562 0.02250 = 0.02191 0.00000 0.00124 0.00000 C2 1 -0.081990 0.250000 0.558555 10.50000 0.01333 0.01854 = 0.01983 0.00000 -0.00035 0.00000 C3 1 0.014110 0.250000 0.473410 10.50000 0.01322 0.01820 = 0.01835 0.00000 -0.00081 0.00000 AFIX 43 H3 2 -0.004471 0.250000 0.388721 10.50000 -1.20000 AFIX 0 C4 1 0.140663 0.250000 0.514645 10.50000 0.01295 0.01776 = 0.02123 0.00000 -0.00017 0.00000 C5 1 0.157128 0.250000 0.642697 10.50000 0.01680 0.02718 = 0.02173 0.00000 -0.00460 0.00000 AFIX 43 H5 2 0.239639 0.250000 0.676712 10.50000 -1.20000 AFIX 0 C6 1 0.052735 0.250000 0.717637 10.50000 0.02172 0.03902 = 0.01794 0.00000 -0.00242 0.00000 AFIX 43 H6 2 0.067533 0.250000 0.803016 10.50000 -1.20000 AFIX 0 C7 1 0.218781 0.250000 0.305915 10.50000 0.02269 0.03520 = 0.02397 0.00000 0.00738 0.00000 H7A 2 0.168474 0.134757 0.282301 11.00000 0.04217 H7B 2 0.294519 0.250000 0.265702 10.50000 0.05397 C8 1 0.368512 0.250000 0.482522 10.50000 0.01235 0.03623 = 0.04201 0.00000 -0.00099 0.00000 H8A 2 0.385859 0.133824 0.528095 11.00000 0.03765 H8B 2 0.423059 0.250000 0.421171 10.50000 0.07832 HKLF 4 REM 16srv052 in Pnma #62 REM R1 = 0.0428 for 1318 Fo > 4sig(Fo) and 0.0506 for all 1542 data REM 81 parameters refined using 0 restraints END WGHT 0.0906 0.0494 REM Highest difference peak 0.448, deepest hole -0.300, 1-sigma level 0.055 Q1 1 0.1032 0.2500 0.6781 10.50000 0.05 0.45 Q2 1 0.0790 0.2500 0.4911 10.50000 0.05 0.42 Q3 1 -0.0355 0.2500 0.5168 10.50000 0.05 0.39 Q4 1 0.1495 0.2500 0.5787 10.50000 0.05 0.38 Q5 1 -0.0082 0.2500 0.6915 10.50000 0.05 0.37 Q6 1 0.1953 0.2500 0.4774 10.50000 0.05 0.33 Q7 1 -0.1428 0.2500 0.5403 10.50000 0.05 0.32 REM The information below was added by Olex2. REM REM R1 = 0.0428 for 1318 Fo > 4sig(Fo) and 0.0506 for all 20022 data REM n/a parameters refined using n/a restraints REM Highest difference peak 0.45, deepest hole -0.30 REM Mean Shift 0.001, Max Shift -0.006. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.0506 REM R1_gt = 0.0428 REM wR_ref = 0.1331 REM GOOF = 1.077 REM Shift_max = -0.006 REM Shift_mean = 0.001 REM Reflections_all = 20022 REM Reflections_gt = 1318 REM Parameters = n/a REM Hole = -0.30 REM Peak = 0.45 REM Flack = n/a ;