# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2004 data_global _publ_contact_author_email 'DANIEL SANDMAN@UML.EDU' _publ_contact_author_name 'Prof Daniel Sandman' _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _publ_contact_author ; Prof Daniel Sandman Department of Chemistry University of Massachusetts Lowell 265 Riverside Street OH-420 Lowell Massachusetts 01854-5046 UNITED STATES OF AMERICA ; _publ_section_title ; Diiminoisoindoline: tautomerism, conformations, and polymorphism ; loop_ _publ_author_name 'Daniel Sandman' 'Peter Erk' 'Bruce M. Foxman' 'Chengyun Guo' 'Jeffrey M. Njus' 'R.van Gelder' ; Z.-Q.Zhang ; data_Form_A _database_code_depnum_ccdc_archive 'CCDC 228419' _audit_creation_date 03-25-11 _audit_creation_method CRYSTALS_ver_12-03-99 # diiminoisoindoline_form_A_KC140_1_DJS #========================================================================== _chemical_name_systematic # IUPAC name, in full ; ? ; _chemical_melting_point ? # choose from 'full, fullcycle, atomblock, userblock, diagonal, sparse' _refine_ls_matrix_type full # choose from 'heavy, direct, difmap, geom' _atom_sites_solution_primary direct # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom # choose from 'none, undef, noref, refall, refxyz, refU, constr, mixed' _refine_ls_hydrogen_treatment mixed #**************************************************************************** # General computing #============================================================ _computing_structure_refinement ; CRYSTALS (Watkin et al 2003) ; _computing_publication_material ; CRYSTALS (Watkin et al 2003) ; _computing_molecular_graphics ; CAMERON (Watkin et al 1996) ; #============================================================ _cell_length_a 10.8323(16) _cell_angle_alpha 90 _cell_length_b 7.0661(7) _cell_angle_beta 102.916(11) _cell_length_c 19.696(3) _cell_angle_gamma 90 _cell_volume 1469.4(3) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1 ' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x,y+1/2,-z+1/2 x,-y+1/2,z+1/2 # choose from: rm (reference molecule of # known chirality), ad (anomolous # dispersion - ie. Flack param), rmad # (both rm and ad), syn (known from # synthetic pathway), unk (unknown) # or . (not applicable). _chemical_absolute_configuration . loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 International_Tables_Vol_IV_Table_2.2B 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7997 0.0030 International_Tables_Vol_IV_Table_2.2B 'N ' 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 International_Tables_Vol_IV_Table_2.2B _cell_formula_units_Z 4 _chemical_formula_sum ' C16 H14 N6 ' _chemical_formula_moiety ' C16 H14 N6 ' _chemical_compound_source ; ? ; _chemical_formula_weight 290.33 _cell_measurement_reflns_used 24 _cell_measurement_theta_min 24 _cell_measurement_theta_max 47 _cell_measurement_temperature 294 _exptl_crystal_description ' prism ' _exptl_crystal_colour ' colorless ' _exptl_crystal_size_min 0.14 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_max 0.54 _exptl_crystal_density_diffrn 1.312 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 0.677 _diffrn_measurement_device_type ; Enraf-Nonius CAD4 ; _diffrn_radiation_monochromator graphite _computing_data_collection ; Cad4 Express, (Straver, 1992) ; _computing_data_reduction ; MolEN (Fair, 1990) ; _computing_cell_refinement ; Cad4 Express, (Straver, 1992) ; _computing_structure_solution ; SIR92 (Altomare et al, 1994) ; _diffrn_measurement_method \w/2\q _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details ; Azimutal absorption correction (North et al, 1968) ; _exptl_absorpt_correction_T_min 0.82 _exptl_absorpt_correction_T_max 0.91 # Sheldrick geometric definitions 0.82 0.91 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 3 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 294 _diffrn_reflns_number 3186 _reflns_number_total 3092 _diffrn_reflns_av_R_equivalents 0.04 # Number of reflections with Friedels Law is 3092 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 3093 _diffrn_reflns_theta_min 4.187 _diffrn_reflns_theta_max 76.631 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 76.631 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _reflns_limit_h_min -13 _reflns_limit_h_max 13 _reflns_limit_k_min 0 _reflns_limit_k_max 8 _reflns_limit_l_min 0 _reflns_limit_l_max 24 _refine_diff_density_min -0.16 _refine_diff_density_max 0.15 _refine_ls_number_reflns 2319 _refine_ls_number_restraints 0 _refine_ls_number_parameters 224 #_refine_ls_R_factor_ref 0.0376 _refine_ls_wR_factor_ref 0.0463 _refine_ls_goodness_of_fit_ref 1.0812 #_reflns_number_all 3092 _refine_ls_R_factor_all 0.0571 _refine_ls_wR_factor_all 0.0778 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>1.96u(I) _reflns_number_gt 2319 _refine_ls_R_factor_gt 0.0376 _refine_ls_wR_factor_gt 0.0463 _refine_ls_shift/su_max 0.000790 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 1.92 1.45 1.37 ; _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54180 ## -------------------REFERENCES ----------------------## ## Insert your own references - in alphabetic order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo G., Guagliardi A., Burla M.C., Polidori, G. & Camalli, M. (1994) SIR92 - a program for automatic solution of crystal structures by direct methods. J. Appl. Cryst. (27), 435-435 Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K., Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Enraf-Nonius, (1989) Cad4 Express. North, A.C.T., Phillips, D.C. and Mathews, F.S., (1968), Acta Cryst, A24, 351-359 Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin D.J. (1994), Acta Cryst, A50, 411-437 Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996) CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. Watkin, D.J., Prout, C.K., Lilley, P.M.deQ. (1994), RC93, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 # Replace trailing . with the number of unfound # hydrogen atoms attaced to relavent atom 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_refinement_disorder_assembly _atom_site_refinement_disorder_group _atom_site_attached_hydrogens N11 N 0.09425(12) 0.12167(18) 0.94255(7) 0.0545 1.0000 Uani . . . . . . N12 N -0.09691(10) 0.21370(16) 0.96920(6) 0.0486 1.0000 Uani . . . . . . N13 N -0.27894(12) 0.39976(19) 0.97425(7) 0.0594 1.0000 Uani . . . . . . N21 N 0.44530(12) 0.2579(2) 1.02561(6) 0.0565 1.0000 Uani . . . . . . N22 N 0.59693(11) 0.04107(17) 1.08090(6) 0.0527 1.0000 Uani . . . . . . N23 N 0.74873(12) -0.11779(19) 1.16354(7) 0.0602 1.0000 Uani . . . . . . C11 C -0.00128(12) 0.24032(18) 0.93830(6) 0.0437 1.0000 Uani . . . . . . C12 C -0.01235(11) 0.42043(17) 0.89920(6) 0.0427 1.0000 Uani . . . . . . C13 C 0.06096(12) 0.5041(2) 0.85863(8) 0.0541 1.0000 Uani . . . . . . C14 C 0.02074(14) 0.6777(2) 0.82901(9) 0.0621 1.0000 Uani . . . . . . C15 C -0.08741(14) 0.7642(2) 0.84089(9) 0.0611 1.0000 Uani . . . . . . C16 C -0.16066(12) 0.6796(2) 0.88182(8) 0.0521 1.0000 Uani . . . . . . C17 C -0.12165(11) 0.50538(18) 0.91046(6) 0.0422 1.0000 Uani . . . . . . C18 C -0.17552(11) 0.37176(18) 0.95452(6) 0.0447 1.0000 Uani . . . . . . C21 C 0.53222(11) 0.20191(19) 1.07985(6) 0.0456 1.0000 Uani . . . . . . C22 C 0.56827(11) 0.30566(18) 1.14662(6) 0.0439 1.0000 Uani . . . . . . C23 C 0.53285(12) 0.4777(2) 1.16958(8) 0.0522 1.0000 Uani . . . . . . C24 C 0.58475(14) 0.5268(2) 1.23817(8) 0.0599 1.0000 Uani . . . . . . C25 C 0.66696(14) 0.4072(2) 1.28231(8) 0.0594 1.0000 Uani . . . . . . C26 C 0.70530(12) 0.2373(2) 1.25826(7) 0.0528 1.0000 Uani . . . . . . C27 C 0.65510(11) 0.18916(19) 1.18988(7) 0.0443 1.0000 Uani . . . . . . C28 C 0.67377(11) 0.0231(2) 1.14716(7) 0.0470 1.0000 Uani . . . . . . H13 H -0.2958(17) 0.296(3) 1.0035(10) 0.075(5) 1.0000 Uiso . . . . . . H23 H 0.7894(17) -0.105(3) 1.2097(10) 0.068(5) 1.0000 Uiso . . . . . . H111 H 0.1528(15) 0.142(2) 0.9167(8) 0.055(4) 1.0000 Uiso . . . . . . H112 H 0.0957(18) 0.004(3) 0.9693(11) 0.086(6) 1.0000 Uiso . . . . . . H211 H 0.4025(17) 0.367(3) 1.0286(9) 0.069(5) 1.0000 Uiso . . . . . . H212 H 0.4275(18) 0.178(3) 0.9860(11) 0.079(5) 1.0000 Uiso . . . . . . H131 H 0.1357 0.4452 0.8513 0.0653 1.0000 Uiso . . . . . . H141 H 0.0681 0.7386 0.8001 0.0754 1.0000 Uiso . . . . . . H151 H -0.1119 0.8839 0.8204 0.0727 1.0000 Uiso . . . . . . H161 H -0.2347 0.7394 0.8899 0.0617 1.0000 Uiso . . . . . . H231 H 0.4754 0.5590 1.1396 0.0628 1.0000 Uiso . . . . . . H241 H 0.5633 0.6451 1.2553 0.0723 1.0000 Uiso . . . . . . H251 H 0.6976 0.4420 1.3296 0.0710 1.0000 Uiso . . . . . . H261 H 0.7640 0.1570 1.2879 0.0625 1.0000 Uiso . . . . . . 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 N11 0.0536(6) 0.0475(6) 0.0666(7) 0.0107(6) 0.0224(6) 0.0193(5) N12 0.0486(6) 0.0452(6) 0.0529(6) 0.0067(5) 0.0130(5) 0.0138(5) N13 0.0520(6) 0.0616(8) 0.0692(8) 0.0149(6) 0.0234(6) 0.0185(5) N21 0.0569(7) 0.0600(7) 0.0495(6) -0.0031(5) 0.0054(5) 0.0207(6) N22 0.0531(6) 0.0561(7) 0.0479(6) -0.0040(5) 0.0095(5) 0.0176(5) N23 0.0601(7) 0.0594(8) 0.0610(8) 0.0073(6) 0.0134(6) 0.0229(6) C11 0.0434(6) 0.0411(6) 0.0451(6) -0.0010(5) 0.0071(5) 0.0085(5) C12 0.0398(6) 0.0402(6) 0.0450(6) -0.0018(5) 0.0033(5) 0.0058(5) C13 0.0445(7) 0.0520(8) 0.0668(8) 0.0046(6) 0.0148(6) 0.0063(6) C14 0.0525(8) 0.0573(9) 0.0788(10) 0.0156(7) 0.0198(7) 0.0034(7) C15 0.0553(8) 0.0474(8) 0.0793(10) 0.0178(7) 0.0121(7) 0.0095(6) C16 0.0452(7) 0.0455(7) 0.0638(8) 0.0051(6) 0.0085(6) 0.0115(5) C17 0.0388(6) 0.0401(6) 0.0445(6) -0.0008(5) 0.0026(5) 0.0064(5) C18 0.0417(6) 0.0456(6) 0.0452(6) 0.0028(5) 0.0065(5) 0.0098(5) C21 0.0424(6) 0.0501(7) 0.0458(6) 0.0004(5) 0.0127(5) 0.0111(5) C22 0.0374(6) 0.0475(7) 0.0487(6) -0.0008(5) 0.0137(5) 0.0038(5) C23 0.0456(7) 0.0484(7) 0.0631(8) -0.0054(6) 0.0132(6) 0.0055(6) C24 0.0511(7) 0.0582(9) 0.0723(9) -0.0204(7) 0.0177(6) -0.0035(7) C25 0.0502(7) 0.0708(10) 0.0563(8) -0.0166(7) 0.0097(6) -0.0125(7) C26 0.0430(7) 0.0632(8) 0.0501(7) -0.0009(6) 0.0056(5) -0.0019(6) C27 0.0365(6) 0.0496(7) 0.0480(6) 0.0009(5) 0.0119(5) 0.0021(5) C28 0.0425(6) 0.0504(7) 0.0497(7) 0.0026(5) 0.0140(5) 0.0097(5) _refine_ls_extinction_coef 43(6) _refine_ls_extinction_method 'Larson 1970 Crystallographic Computing eq 22' loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N11 . H112 . 0.98(2) no N11 . H111 . 0.909(17) no N11 . C11 . 1.3198(16) yes N12 . C18 . 1.3950(16) yes N12 . C11 . 1.3270(16) yes N13 . H13 . 0.98(2) no N13 . C18 . 1.2806(17) yes N21 . H212 . 0.95(2) no N21 . H211 . 0.91(2) no N21 . C21 . 1.3172(17) yes N22 . C28 . 1.3880(17) yes N22 . C21 . 1.3330(17) yes N23 . H23 . 0.922(19) no N23 . C28 . 1.2795(17) yes C11 . C12 . 1.4785(17) yes C12 . C17 . 1.3888(17) yes C12 . C13 . 1.3791(19) yes C13 . H131 . 0.950 no C13 . C14 . 1.386(2) yes C14 . H141 . 0.949 no C14 . C15 . 1.387(2) yes C15 . H151 . 0.949 no C15 . C16 . 1.387(2) yes C16 . H161 . 0.950 no C16 . C17 . 1.3806(18) yes C17 . C18 . 1.4871(18) yes C21 . C22 . 1.4797(18) yes C22 . C27 . 1.3892(17) yes C22 . C23 . 1.3809(19) yes C23 . H231 . 0.950 no C23 . C24 . 1.386(2) yes C24 . H241 . 0.949 no C24 . C25 . 1.384(2) yes C25 . H251 . 0.949 no C25 . C26 . 1.388(2) yes C26 . H261 . 0.950 no C26 . C27 . 1.3777(19) yes C27 . C28 . 1.4841(18) yes loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag H112 . N11 . H111 . 120.2(16) no H112 . N11 . C11 . 119.4(12) no H111 . N11 . C11 . 120.0(10) no C18 . N12 . C11 . 107.12(11) yes H13 . N13 . C18 . 110.8(11) no H212 . N21 . H211 . 123.0(16) no H212 . N21 . C21 . 117.9(12) no H211 . N21 . C21 . 119.0(11) no C28 . N22 . C21 . 107.18(11) yes H23 . N23 . C28 . 108.2(11) no C12 . C11 . N11 . 123.44(12) yes C12 . C11 . N12 . 112.34(11) yes N11 . C11 . N12 . 124.21(12) yes C17 . C12 . C13 . 121.95(12) yes C17 . C12 . C11 . 105.17(11) yes C13 . C12 . C11 . 132.88(12) yes H131 . C13 . C14 . 121.456 no H131 . C13 . C12 . 121.442 no C14 . C13 . C12 . 117.10(12) yes H141 . C14 . C15 . 119.405 no H141 . C14 . C13 . 119.466 no C15 . C14 . C13 . 121.13(13) yes H151 . C15 . C16 . 119.297 no H151 . C15 . C14 . 119.187 no C16 . C15 . C14 . 121.52(13) yes H161 . C16 . C17 . 121.365 no H161 . C16 . C15 . 121.286 no C17 . C16 . C15 . 117.35(12) yes C18 . C17 . C16 . 132.88(11) yes C18 . C17 . C12 . 106.17(10) yes C16 . C17 . C12 . 120.94(12) yes N13 . C18 . N12 . 126.56(12) yes N13 . C18 . C17 . 124.26(12) yes N12 . C18 . C17 . 109.17(10) yes C22 . C21 . N21 . 124.80(12) yes C22 . C21 . N22 . 112.04(11) yes N21 . C21 . N22 . 123.15(12) yes C27 . C22 . C23 . 121.35(12) yes C27 . C22 . C21 . 105.04(11) yes C23 . C22 . C21 . 133.61(12) yes H231 . C23 . C24 . 121.427 no H231 . C23 . C22 . 121.341 no C24 . C23 . C22 . 117.23(13) yes H241 . C24 . C25 . 119.274 no H241 . C24 . C23 . 119.194 no C25 . C24 . C23 . 121.53(14) yes H251 . C25 . C26 . 119.575 no H251 . C25 . C24 . 119.544 no C26 . C25 . C24 . 120.88(13) yes H261 . C26 . C27 . 121.203 no H261 . C26 . C25 . 121.125 no C27 . C26 . C25 . 117.67(13) yes C28 . C27 . C26 . 132.49(12) yes C28 . C27 . C22 . 106.27(11) yes C26 . C27 . C22 . 121.23(12) yes N23 . C28 . N22 . 121.46(13) yes N23 . C28 . C27 . 129.15(13) yes N22 . C28 . C27 . 109.36(11) yes data_Form_B _database_code_depnum_ccdc_archive 'CCDC 228420' _audit_creation_date 03-24-11 _audit_creation_method CRYSTALS_ver_12-03-99 # diiminoisoindoline_Form_B #========================================================================== _chemical_name_systematic # IUPAC name, in full ; ? ; _chemical_melting_point ? # choose from 'full, fullcycle, atomblock, userblock, diagonal, sparse' _refine_ls_matrix_type full # choose from 'heavy, direct, difmap, geom' _atom_sites_solution_primary direct # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom # choose from 'none, undef, noref, refall, refxyz, refU, constr, mixed' _refine_ls_hydrogen_treatment mixed #**************************************************************************** # General computing #============================================================ _computing_structure_refinement ; CRYSTALS (Watkin et al 2003) ; _computing_publication_material ; CRYSTALS (Watkin et al 2003) ; _computing_molecular_graphics ; CAMERON (Watkin et al 1996) ; #============================================================ _cell_length_a 8.3777(4) _cell_angle_alpha 90 _cell_length_b 6.4807(2) _cell_angle_beta 97.793(4) _cell_length_c 12.9513(5) _cell_angle_gamma 90 _cell_volume 696.68(5) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1 ' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x,y+1/2,-z+1/2 x,-y+1/2,z+1/2 # choose from: rm (reference molecule of # known chirality), ad (anomolous # dispersion - ie. Flack param), rmad # (both rm and ad), syn (known from # synthetic pathway), unk (unknown) # or . (not applicable). _chemical_absolute_configuration . loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'N ' 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 International_Tables_Vol_IV_Table_2.2B 'C ' 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 International_Tables_Vol_IV_Table_2.2B 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 International_Tables_Vol_IV_Table_2.2B _cell_formula_units_Z 4 _chemical_formula_sum ' C8 H7 N3 ' _chemical_formula_moiety ' C8 H7 N3 ' _chemical_compound_source ; ? ; _chemical_formula_weight 145.16 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 18 _cell_measurement_theta_max 22 _cell_measurement_temperature 294 _exptl_crystal_description ' prism ' _exptl_crystal_colour ' colorless ' _exptl_crystal_size_min 0.22 _exptl_crystal_size_mid 0.58 _exptl_crystal_size_max 0.72 _exptl_crystal_density_diffrn 1.384 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 304 _exptl_absorpt_coefficient_mu 0.089 _diffrn_measurement_device_type ; cad-4 ; _diffrn_radiation_monochromator graphite _computing_data_collection ; Cad4 Express, (Straver, 1992) ; _computing_data_reduction ; MolEn (Fair, 1990) ; _computing_cell_refinement ; Cad4 Express, (Straver, 1992) ; _computing_structure_solution ; SIR92 (Altomare et al, 1994) ; _diffrn_measurement_method \w/2\q _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details ; Azimutal absorption correction (North et al, 1968) ; _exptl_absorpt_correction_T_min 0.93 _exptl_absorpt_correction_T_max 0.98 # Sheldrick geometric definitions 0.95 0.98 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 3 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 294 _diffrn_reflns_number 1501 _reflns_number_total 1406 _diffrn_reflns_av_R_equivalents 0.04 # Number of reflections with Friedels Law is 1406 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 1412 _diffrn_reflns_theta_min 2.454 _diffrn_reflns_theta_max 26.286 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.286 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _reflns_limit_h_min 0 _reflns_limit_h_max 10 _reflns_limit_k_min 0 _reflns_limit_k_max 8 _reflns_limit_l_min -16 _reflns_limit_l_max 15 _refine_diff_density_min -0.16 _refine_diff_density_max 0.20 _refine_ls_number_reflns 1196 _refine_ls_number_restraints 0 _refine_ls_number_parameters 113 #_refine_ls_R_factor_ref 0.0344 _refine_ls_wR_factor_ref 0.0462 _refine_ls_goodness_of_fit_ref 1.0724 #_reflns_number_all 1406 _refine_ls_R_factor_all 0.0446 _refine_ls_wR_factor_all 0.0665 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>1.96u(I) _reflns_number_gt 1196 _refine_ls_R_factor_gt 0.0344 _refine_ls_wR_factor_gt 0.0462 _refine_ls_shift/su_max 0.000450 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 1.75 1.38 1.13 ; _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 ## -------------------REFERENCES ----------------------## ## Insert your own references - in alphabetic order _publ_section_references ; User-defined data collection reference Spare 5 Spare 6 Altomare, A., Cascarano, G., Giacovazzo G., Guagliardi A., Burla M.C., Polidori, G. & Camalli, M. (1994) SIR92 - a program for automatic solution of crystal structures by direct methods. J. Appl. Cryst. (27), 435-435 Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K., Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. North, A.C.T., Phillips, D.C. and Mathews, F.S., (1968), Acta Cryst, A24, 351-359 Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin D.J. (1994), Acta Cryst, A50, 411-437 Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996) CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 # Replace trailing . with the number of unfound # hydrogen atoms attaced to relavent atom 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_refinement_disorder_assembly _atom_site_refinement_disorder_group _atom_site_attached_hydrogens C1 C 0.36724(14) 0.27466(18) 0.56743(9) 0.0315 1.0000 Uani . . . . . . C2 C 0.26962(13) 0.10111(18) 0.59998(8) 0.0302 1.0000 Uani . . . . . . C3 C 0.20575(14) 0.0576(2) 0.69103(9) 0.0363 1.0000 Uani . . . . . . C4 C 0.11145(16) -0.1181(2) 0.69149(10) 0.0420 1.0000 Uani . . . . . . C5 C 0.08626(17) -0.2482(2) 0.60570(11) 0.0452 1.0000 Uani . . . . . . C6 C 0.15258(17) -0.2047(2) 0.51552(10) 0.0406 1.0000 Uani . . . . . . C7 C 0.24240(13) -0.02715(18) 0.51375(9) 0.0314 1.0000 Uani . . . . . . C8 C 0.32194(13) 0.07338(18) 0.43031(9) 0.0318 1.0000 Uani . . . . . . N1 N 0.42384(14) 0.42558(18) 0.62920(8) 0.0391 1.0000 Uani . . . . . . N2 N 0.39146(12) 0.25787(15) 0.46810(7) 0.0344 1.0000 Uani . . . . . . N3 N 0.32870(14) 0.01039(18) 0.33754(8) 0.0408 1.0000 Uani . . . . . . H1 H 0.403(2) 0.432(3) 0.6971(14) 0.052(4) 1.0000 Uiso . . . . . . H2 H 0.4800(19) 0.527(3) 0.6021(13) 0.055(5) 1.0000 Uiso . . . . . . H3 H 0.276(2) -0.113(3) 0.3294(14) 0.062(5) 1.0000 Uiso . . . . . . H31 H 0.2258 0.1447 0.7505 0.0442 1.0000 Uiso . . . . . . H41 H 0.0631 -0.1502 0.7518 0.0514 1.0000 Uiso . . . . . . H51 H 0.0227 -0.3689 0.6087 0.0546 1.0000 Uiso . . . . . . H61 H 0.1364 -0.2944 0.4570 0.0488 1.0000 Uiso . . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0342(5) 0.0325(6) 0.0290(6) 0.0030(4) 0.0080(4) 0.0008(4) C2 0.0309(5) 0.0321(6) 0.0280(6) 0.0049(4) 0.0055(4) 0.0019(4) C3 0.0400(6) 0.0411(7) 0.0289(6) 0.0035(5) 0.0089(4) 0.0009(5) C4 0.0429(6) 0.0490(8) 0.0364(6) 0.0129(6) 0.0132(5) -0.0022(6) C5 0.0487(7) 0.0413(7) 0.0462(7) 0.0095(6) 0.0090(6) -0.0114(6) C6 0.0483(7) 0.0375(7) 0.0359(7) 0.0011(5) 0.0054(5) -0.0070(5) C7 0.0334(5) 0.0327(6) 0.0282(6) 0.0043(4) 0.0048(4) 0.0011(5) C8 0.0347(5) 0.0338(6) 0.0274(5) 0.0042(4) 0.0060(4) 0.0018(4) N1 0.0522(6) 0.0365(6) 0.0311(5) -0.0024(4) 0.0142(4) -0.0090(5) N2 0.0423(5) 0.0345(5) 0.0281(5) 0.0016(4) 0.0109(4) -0.0042(4) N3 0.0538(6) 0.0421(6) 0.0275(5) -0.0016(4) 0.0094(4) -0.0055(5) _refine_ls_extinction_coef 80(13) _refine_ls_extinction_method 'Larson 1970 Crystallographic Computing eq 22' loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 . N2 . 1.3336(15) yes C1 . N1 . 1.3110(16) yes C1 . C2 . 1.4850(15) yes C2 . C7 . 1.3860(16) yes C2 . C3 . 1.3882(15) yes C3 . H31 . 0.951 no C3 . C4 . 1.3868(18) yes C4 . H41 . 0.951 no C4 . C5 . 1.388(2) yes C5 . H51 . 0.950 no C5 . C6 . 1.3886(19) yes C6 . H61 . 0.950 no C6 . C7 . 1.3766(17) yes C7 . C8 . 1.4938(16) yes C8 . N3 . 1.2775(15) yes C8 . N2 . 1.3896(15) yes N1 . H2 . 0.905(17) no N1 . H1 . 0.920(18) no N3 . H3 . 0.910(19) no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag N2 . C1 . N1 . 124.04(11) yes N2 . C1 . C2 . 111.95(10) yes N1 . C1 . C2 . 124.01(11) yes C7 . C2 . C3 . 121.50(11) yes C7 . C2 . C1 . 105.20(9) yes C3 . C2 . C1 . 133.27(11) yes H31 . C3 . C4 . 121.497 no H31 . C3 . C2 . 121.394 no C4 . C3 . C2 . 117.11(11) yes H41 . C4 . C5 . 119.329 no H41 . C4 . C3 . 119.311 no C5 . C4 . C3 . 121.36(11) yes H51 . C5 . C6 . 119.502 no H51 . C5 . C4 . 119.491 no C6 . C5 . C4 . 121.01(12) yes H61 . C6 . C7 . 121.135 no H61 . C6 . C5 . 121.101 no C7 . C6 . C5 . 117.76(12) yes C8 . C7 . C6 . 132.46(11) yes C8 . C7 . C2 . 106.29(10) yes C6 . C7 . C2 . 121.22(11) yes N3 . C8 . N2 . 122.43(11) yes N3 . C8 . C7 . 128.47(11) yes N2 . C8 . C7 . 109.10(9) yes H2 . N1 . H1 . 121.0(15) no H2 . N1 . C1 . 117.9(10) no H1 . N1 . C1 . 121.1(11) no C1 . N2 . C8 . 107.38(9) yes H3 . N3 . C8 . 107.9(11) no