Electronic Supplementary Material for CrystEngComm This Journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_coden_ASTM ? _journal_coeditor_code ? _journal_coeditor_name ? _journal_coeditor_notes ? _journal_date_accepted ? _journal_date_from_coeditor ? _journal_date_printers_final ? _journal_date_printers_first ? _journal_date_proofs_in ? _journal_date_proofs_out ? loop_ _publ_author_name _publ_author_address F.P.A.Fabbiani ; School of Biomedical, Biomolecular & Chemical Sciences, University of Western Australia , Crawley, Australia ; J.J.McKinnon ; School of Biomedical, Biomolecular & Chemical Sciences, University of Western Australia , Crawley, Australia ; L.T.Byrne ; School of Biomedical, Biomolecular & Chemical Sciences, University of Western Australia , Crawley, Australia ; M.A.Spackman ; School of Biomedical, Biomolecular & Chemical Sciences, University of Western Australia , Crawley, Australia ; _publ_contact_author_email francescapaola@gmail.com _publ_contact_author_name 'Francesca P. A. Fabbiani' _publ_section_title ;Solvent inclusion in the structural voids of form II carbamazepine: single-crystal X-ray diffraction, NMR spectroscopy and Hirshfeld surface analysis ; data_carbamazepine_II_THF_solvate _database_code_depnum_ccdc_archive 'CCDC 641710' _exptl_crystal_recrystallization_method 'Recrystallisation by evaporation of THF solution' _audit_creation_date 07-01-08 _audit_creation_method CRYSTALS_ver_12.82 _oxford_structure_analysis_title 'carba3_hex_int in R-3' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 35.243(5) _cell_length_b 35.243(5) _cell_length_c 5.1853(10) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 120 _cell_volume 5577.7(15) _symmetry_cell_setting Trigonal _symmetry_space_group_name_H-M 'R -3 ' _symmetry_space_group_name_Hall '-R 3' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z x+1/3,y+2/3,z+2/3 -x+1/3,-y+2/3,-z+2/3 x+2/3,y+1/3,z+1/3 -x+2/3,-y+1/3,-z+1/3 -y,x-y,z y,-x+y,-z -y+1/3,x-y+2/3,z+2/3 y+1/3,-x+y+2/3,-z+2/3 -y+2/3,x-y+1/3,z+1/3 y+2/3,-x+y+1/3,-z+1/3 -x+y,-x,z x-y,x,-z -x+y+1/3,-x+2/3,z+2/3 x-y+1/3,x+2/3,-z+2/3 -x+y+2/3,-x+1/3,z+1/3 x-y+2/3,x+1/3,-z+1/3 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 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' 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 C 4.2.6.8 and 6.1.1.4' 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 C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 18 # Given Formula = C15.40 H12.80 N2 O1.10 # Dc = 1.30 Fooo = 2289.60 Mu = 0.84 M = 243.48 # Found Formula = C15.40 H12 N2 O1.10 # Dc = 1.30 FOOO = 2289.60 Mu = 0.84 M = 242.68 _chemical_formula_sum 'C15.40 H12 N2 O1.10' _chemical_formula_moiety 'C15 H12 N2 O1, 0.1(C4 H8 O1)' _chemical_compound_source ? _chemical_formula_weight 243.48 _cell_measurement_reflns_used 12631 _cell_measurement_theta_min 3 _cell_measurement_theta_max 31 _cell_measurement_temperature 100 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_min 0.25 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_max 0.60 _exptl_crystal_density_diffrn 1.300 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 2289.600 _exptl_absorpt_coefficient_mu 0.084 # Sheldrick geometric approximatio 0.97 0.98 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ;CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.91 _exptl_absorpt_correction_T_max 0.98 _diffrn_measurement_device_type 'Oxford Diffraction XCALIBUR' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' _computing_data_collection 'Xcalibur, (Oxford Diffraction, 2002)' _computing_data_reduction 'CrysAlis RED, (Oxford Diffraction, 2002)' _computing_cell_refinement 'CrysAlis RED, (Oxford Diffraction, 2002)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _refine_special_details ; All non-H-atoms were refined with anisotropic thermal parameters. Hydrogen atoms were placed in idealised positions. Hydrogen atoms attached to the nitrogen atom were located on a difference Fourier map. Subsequent to location, the position of all hydrogen atoms was regularised using the X-ray data subject to geometrty restraints. Hydrogen atoms were subsequenlty allowed to ride on their parent atom. positions of all H-atoms, which were placed geometrically, were fixed during refinement. Hydrogen atoms for the THF moiety were omitted but taken into account for calculation of crystal properties. A theta cut off of 29 deg. was applied during data merging. DISORDER The THF molecule was found to be disordered about the b3 Wyckoff position (0,0,0.5) and gave rise to a 1 : 0.1 CBZ : THF solvate. Details of the disorder model can be found in the manuscipt. The following is the output of checkCIF/PLATON routine available at : http://journals.iucr.org/services/cif/checking/checkbasic.html PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ... ? Calculated: C15 H12 N2 O, C0.40 O0.10 Reported: C15 H12 N2 O1, 0.1(C4 H8 O1) The reoported MoietyFormula String is more meaningful. PLAT302_ALERT_4_C Anion/Solvent Disorder ......................37.00 Perc. See above under "disorder". PLAT420_ALERT_2_C D-H Without Acceptor N2 - H2 ... ? Noted, no acceptor for N2-H2 in the structure. FORMU01_ALERT_1_G There is a discrepancy between the atom counts in the _chemical_formula_sum and _chemical_formula_moiety. This is usually due to the moiety formula being in the wrong format. Atom count from _chemical_formula_sum: C15.4 H12 N2 O1.1 Atom count from _chemical_formula_moiety:C15.4 H12.8 N2 O1.1 Hydrogen atoms for the THF molecule were not included in the refinement but were taken into account for calculation of density, F(000), absorption coefficient andmolecular weight. The following is the extra output of checkCIF/PLATON routine using the .fcf file 910_ALERT_3_C # Missing FCF Reflections Below TH(Min) ........ 3 912_ALERT_3_C # Missing FCF Reflections Above STH/L=0.6 ...... 4 Resolution and completeness are given below: #=============================================================================== Resolution & Completeness Statistics (Cumulative) #=============================================================================== Theta sin(th)/Lambda Complete Expected Measured Missing #------------------------------------------------------------------------------- 20.82 0.500 0.998 1300 1297 3 23.01 0.550 0.998 1735 1732 3 25.24 0.600 0.999 2255 2252 3 #----------------------------------------------------------- ACTA Min. Res. ---- 27.51 0.650 0.999 2847 2844 3 28.79 0.678 0.998 3209 3202 7 ; _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 100 _diffrn_reflns_number 37290 _reflns_number_total 3202 #_diffrn_reflns_av_R_equivalents 0.000 # Number of reflections with Friedels Law is 3202 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 3230 #_diffrn_reflns_theta_max 28.897 #_diffrn_reflns_theta_min 3.069 #_diffrn_reflns_limit_h_max 47 #_diffrn_reflns_limit_h_min -47 #_diffrn_reflns_limit_k_max 47 #_diffrn_reflns_limit_k_min -47 #_diffrn_reflns_limit_l_max 7 #_diffrn_reflns_limit_l_min -6 _diffrn_reflns_av_R_equivalents 0.0293 # Scaled and merged with SORTAV # R.H. Blessing, (1987) Cryst. Rev. 1, 3-58 # R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397 _diffrn_reflns_theta_min 3.058 _diffrn_reflns_theta_max 28.788 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.788 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 47 _diffrn_reflns_limit_k_min -47 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 0 _reflns_limit_h_min -47 _reflns_limit_h_max 22 _reflns_limit_k_min 0 _reflns_limit_k_max 47 _reflns_limit_l_min 0 _reflns_limit_l_max 7 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.29 _refine_diff_density_max 0.52 _refine_ls_number_reflns 3202 _refine_ls_number_restraints 0 _refine_ls_number_parameters 175 #_refine_ls_R_factor_ref 0.0688 _refine_ls_wR_factor_ref 0.1554 _refine_ls_goodness_of_fit_ref 0.9762 #_reflns_number_all 3202 _refine_ls_R_factor_all 0.0688 _refine_ls_wR_factor_all 0.1554 # No actual I/u(I) cutoff was used for refinement. The # threshold below is used for "_gt" information ONLY: _reflns_threshold_expression I>2.00u(I) _reflns_number_gt 2370 _refine_ls_R_factor_gt 0.0512 _refine_ls_wR_factor_gt 0.1482 _refine_ls_shift/su_max 0.000544 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; w=1/[\s^2^(F^2^) + ( 0.09P)^2^ + 5.46P] where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; _publ_section_abstract # Text of the abstract ; ? ; _publ_section_comment # Text of the paper ; ? ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions # Captions to figures ; ? ; _publ_section_exptl_refinement # Some potentially useful phrases are: ; Because the data were collected with molybdenum radiation, there were no measurable anomalous differences, as a consequence of which it was admissible to merge Friedel pairs of reflections. All hydrogen atoms were found in difference density syntheses. Hydrogen atoms were placed geometrically after each cycle. Hydrogen atoms were placed geometrically after each cycle, the preferred orientations of those groups whose conformations could not be assigned unambiguously having been previously identified by examination of a difference Fourier map. Hydrogen atoms were seen in a difference density synthesis. Those attached to carbon atoms were repositioned geometrically. Hydrogen were initially refined with soft restraints on the bonds to regularise their geometry (bond lengths to accepted values, angles either set by symmetry or to accepted values, and U[iso] dependent upon the adjacent bonded atom), after which they were refined with riding constraints only. donated by Bill Clegg: The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularise their geometry (C---H in the range 0.93-98, O---N in the range 0.86-0.89 and O---H = 0.82 \%A) and isotropic adps (U(H) in the range 1.2-1.5 times U~equiv~ of the adjacent atom), after which they were refined with riding constraints. . ; _publ_section_exptl_prep ; ? ; # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo G., Guagliardi A., Burla M.C., Polidori, G. & Camalli, M. (1994). 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. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Oxford Diffraction, (2002). CrysAlis RED. Oxford Diffraction, (2002). Xcalibur User Manual Sheldrick, G.M. (1997). SHELXL-97. University of G\"ottingen, Germany. 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 last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens C1 C 0.38588(4) 0.45808(5) 0.4830(3) 0.0274 1.0000 Uani . . . . . . C2 C 0.38551(5) 0.43170(5) 0.6840(3) 0.0317 1.0000 Uani . . . . . . C3 C 0.34815(5) 0.39190(5) 0.7343(3) 0.0340 1.0000 Uani . . . . . . C4 C 0.31080(5) 0.37802(5) 0.5819(3) 0.0342 1.0000 Uani . . . . . . C5 C 0.31125(5) 0.40459(5) 0.3820(3) 0.0328 1.0000 Uani . . . . . . C6 C 0.34849(5) 0.44547(5) 0.3308(3) 0.0286 1.0000 Uani . . . . . . C7 C 0.34654(5) 0.47360(5) 0.1280(3) 0.0318 1.0000 Uani . . . . . . C8 C 0.36703(5) 0.51762(5) 0.1280(3) 0.0330 1.0000 Uani . . . . . . C9 C 0.39595(5) 0.54736(5) 0.3294(3) 0.0328 1.0000 Uani . . . . . . C10 C 0.39629(6) 0.58686(5) 0.3788(4) 0.0415 1.0000 Uani . . . . . . C11 C 0.42275(6) 0.61533(6) 0.5707(4) 0.0473 1.0000 Uani . . . . . . C12 C 0.44982(6) 0.60562(6) 0.7163(4) 0.0477 1.0000 Uani . . . . . . C13 C 0.45034(5) 0.56698(6) 0.6711(3) 0.0396 1.0000 Uani . . . . . . C14 C 0.42380(5) 0.53818(5) 0.4789(3) 0.0311 1.0000 Uani . . . . . . C15 C 0.45687(5) 0.49842(5) 0.2729(3) 0.0293 1.0000 Uani . . . . . . O1 O 0.45279(4) 0.46325(4) 0.1940(2) 0.0369 1.0000 Uani . . . . . . N1 N 0.42521(4) 0.49882(4) 0.4290(2) 0.0293 1.0000 Uani . . . . . . N2 N 0.49144(4) 0.53757(5) 0.2123(3) 0.0401 1.0000 Uani . . . . . . C16 C 0.3198(11) 0.6510(4) 0.027(2) 0.1773 0.4000 Uani . . . . . . O2 O 0.3333 0.6667 -0.207(2) 0.1382 0.3000 Uani S T . . . . H1 H 0.5108 0.5373 0.1013 0.0452 1.0000 Uiso R . . . . . H2 H 0.4946 0.5611 0.2796 0.0462 1.0000 Uiso R . . . . . H21 H 0.4110 0.4417 0.7876 0.0385 1.0000 Uiso R . . . . . H31 H 0.3479 0.3742 0.8740 0.0421 1.0000 Uiso R . . . . . H41 H 0.2843 0.3499 0.6133 0.0397 1.0000 Uiso R . . . . . H51 H 0.2850 0.3947 0.2742 0.0384 1.0000 Uiso R . . . . . H71 H 0.3276 0.4590 -0.0135 0.0371 1.0000 Uiso R . . . . . H81 H 0.3616 0.5314 -0.0138 0.0405 1.0000 Uiso R . . . . . H101 H 0.3780 0.5938 0.2777 0.0483 1.0000 Uiso R . . . . . H111 H 0.4229 0.6416 0.6004 0.0527 1.0000 Uiso R . . . . . H121 H 0.4681 0.6258 0.8463 0.0506 1.0000 Uiso R . . . . . H131 H 0.4682 0.5596 0.7707 0.0436 1.0000 Uiso 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 C1 0.0240(6) 0.0315(7) 0.0249(7) -0.0033(5) 0.0014(5) 0.0125(5) C2 0.0323(7) 0.0396(8) 0.0256(7) -0.0027(6) -0.0023(5) 0.0197(6) C3 0.0403(8) 0.0369(8) 0.0270(7) 0.0015(6) 0.0030(6) 0.0211(7) C4 0.0316(7) 0.0317(7) 0.0344(8) 0.0006(6) 0.0058(6) 0.0122(6) C5 0.0265(7) 0.0356(8) 0.0323(8) -0.0010(6) -0.0013(6) 0.0126(6) C6 0.0259(6) 0.0333(7) 0.0250(7) -0.0018(5) -0.0001(5) 0.0135(6) C7 0.0275(7) 0.0390(8) 0.0262(7) -0.0005(6) -0.0030(5) 0.0147(6) C8 0.0296(7) 0.0382(8) 0.0299(8) 0.0044(6) 0.0007(6) 0.0161(6) C9 0.0294(7) 0.0326(7) 0.0316(8) 0.0008(6) 0.0059(6) 0.0118(6) C10 0.0398(8) 0.0354(8) 0.0473(10) 0.0038(7) 0.0106(7) 0.0174(7) C11 0.0494(10) 0.0311(8) 0.0526(11) -0.0031(7) 0.0177(8) 0.0135(7) C12 0.0479(10) 0.0368(9) 0.0382(9) -0.0108(7) 0.0084(7) 0.0062(7) C13 0.0361(8) 0.0395(8) 0.0320(8) -0.0064(6) -0.0013(6) 0.0105(7) C14 0.0260(7) 0.0325(7) 0.0280(7) -0.0026(6) 0.0037(5) 0.0095(6) C15 0.0250(6) 0.0394(8) 0.0217(7) -0.0015(5) -0.0025(5) 0.0148(6) O1 0.0359(6) 0.0375(6) 0.0371(6) 0.0030(5) 0.0089(5) 0.0183(5) N1 0.0235(5) 0.0330(6) 0.0281(6) -0.0032(5) 0.0002(5) 0.0115(5) N2 0.0282(6) 0.0341(7) 0.0472(8) -0.0071(6) 0.0109(6) 0.0076(5) C16 0.23(2) 0.082(8) 0.149(9) 0.039(8) -0.056(14) 0.020(8) O2 0.187(10) 0.187(10) 0.040(6) 0.0000 0.0000 0.094(5) _refine_ls_extinction_method None _oxford_refine_ls_scale 1.739(18) 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 . C2 . 1.392(2) yes C1 . C6 . 1.4038(19) yes C1 . N1 . 1.4393(18) yes C2 . C3 . 1.386(2) yes C2 . H21 . 0.950 no C3 . C4 . 1.397(2) yes C3 . H31 . 0.952 no C4 . C5 . 1.392(2) yes C4 . H41 . 0.977 no C5 . C6 . 1.406(2) yes C5 . H51 . 0.984 no C6 . C7 . 1.470(2) yes C7 . C8 . 1.345(2) yes C7 . H71 . 0.951 no C8 . C9 . 1.469(2) yes C8 . H81 . 0.952 no C9 . C10 . 1.410(2) yes C9 . C14 . 1.409(2) yes C10 . C11 . 1.389(3) yes C10 . H101 . 0.954 no C11 . C12 . 1.387(3) yes C11 . H111 . 0.934 no C12 . C13 . 1.391(3) yes C12 . H121 . 0.957 no C13 . C14 . 1.396(2) yes C13 . H131 . 0.948 no C14 . N1 . 1.4361(19) yes C15 . O1 . 1.2436(19) yes C15 . N1 . 1.3842(18) yes C15 . N2 . 1.3438(19) yes N2 . H1 . 0.896 no N2 . H2 . 0.854 no C16 . C16 18_555 1.54(2) yes C16 . C16 12_455 1.54(2) yes C16 . C16 7_665 0.90(3) yes C16 . C16 13_565 0.90(3) yes C16 . O2 . 1.320(15) yes O2 . O2 6_564 1.31(2) 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 C2 . C1 . C6 . 121.03(13) yes C2 . C1 . N1 . 119.64(13) yes C6 . C1 . N1 . 119.33(13) yes C1 . C2 . C3 . 120.22(14) yes C1 . C2 . H21 . 119.0 no C3 . C2 . H21 . 120.8 no C2 . C3 . C4 . 119.98(14) yes C2 . C3 . H31 . 119.9 no C4 . C3 . H31 . 120.1 no C3 . C4 . C5 . 119.60(14) yes C3 . C4 . H41 . 121.0 no C5 . C4 . H41 . 119.4 no C4 . C5 . C6 . 121.37(14) yes C4 . C5 . H51 . 119.6 no C6 . C5 . H51 . 119.1 no C5 . C6 . C1 . 117.76(13) yes C5 . C6 . C7 . 119.43(13) yes C1 . C6 . C7 . 122.79(13) yes C6 . C7 . C8 . 126.77(14) yes C6 . C7 . H71 . 116.3 no C8 . C7 . H71 . 116.9 no C7 . C8 . C9 . 127.14(14) yes C7 . C8 . H81 . 117.3 no C9 . C8 . H81 . 115.5 no C8 . C9 . C10 . 119.58(15) yes C8 . C9 . C14 . 122.79(14) yes C10 . C9 . C14 . 117.62(15) yes C9 . C10 . C11 . 120.96(17) yes C9 . C10 . H101 . 118.8 no C11 . C10 . H101 . 120.3 no C10 . C11 . C12 . 120.52(17) yes C10 . C11 . H111 . 120.2 no C12 . C11 . H111 . 119.3 no C11 . C12 . C13 . 119.81(16) yes C11 . C12 . H121 . 119.4 no C13 . C12 . H121 . 120.8 no C12 . C13 . C14 . 120.00(17) yes C12 . C13 . H131 . 120.9 no C14 . C13 . H131 . 119.0 no C9 . C14 . C13 . 121.08(15) yes C9 . C14 . N1 . 119.14(13) yes C13 . C14 . N1 . 119.77(14) yes O1 . C15 . N1 . 120.71(13) yes O1 . C15 . N2 . 122.68(13) yes N1 . C15 . N2 . 116.61(13) yes C1 . N1 . C14 . 116.56(11) yes C1 . N1 . C15 . 118.87(12) yes C14 . N1 . C15 . 122.18(12) yes C15 . N2 . H1 . 116.3 no C15 . N2 . H2 . 120.9 no H1 . N2 . H2 . 122.9 no #===END