Electronic Supplementary Material for CrystEngComm This Journal is © The Royal Society of Chemistry 2004 data_global _journal_coden_Cambridge 1350 loop_ _publ_author_name 'Colin Pulham' 'David Robert Allan' 'William David' 'Francesca P. A. Fabbiani' 'Stephen A. Moggach' 'Simon Parsons' _publ_contact_author_name 'Dr Colin Pulham' _publ_contact_author_address ; School of Chemistry The University of Edinburgh King's Buildings West Mains Road Edinburgh EH9 3JJ UNITED KINGDOM ; _publ_contact_author_email C.R.PULHAM@ED.AC.UK _publ_requested_journal 'Cryst Eng. Comm.' _publ_section_title ; High-pressure recrystallisation a route to new polymorphs and solvates ; data_phena4 _database_code_depnum_ccdc_archive 'CCDC 237775' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H10' _chemical_formula_weight 178.22 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.937(3) _cell_length_b 3.8218(5) _cell_length_c 17.693(6) _cell_angle_alpha 90.00 _cell_angle_beta 99.13(2) _cell_angle_gamma 90.00 _cell_volume 863.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 142 _cell_measurement_theta_min 3.64 _cell_measurement_theta_max 19.43 _exptl_crystal_description colourless _exptl_crystal_colour block _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.371 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 376 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type 'Empirical & multi-scan' _exptl_absorpt_correction_T_min 0.666627 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details ; SHADE (Parsons, 2004) SADABS (Siemens, 1996) The following data are from Sadabs: ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1938 _diffrn_reflns_av_R_equivalents 0.1001 _diffrn_reflns_av_sigmaI/netI 0.1363 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.64 _diffrn_reflns_theta_max 23.24 _reflns_number_total 451 _reflns_number_gt 197 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1319P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 451 _refine_ls_number_parameters 21 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2491 _refine_ls_R_factor_gt 0.1130 _refine_ls_wR_factor_ref 0.2907 _refine_ls_wR_factor_gt 0.2359 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.078 _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 C1 C 0.5939(7) 0.8572(11) 0.4468(8) 0.036(4) Uiso 1 1 d G . . H1 H 0.5647 0.7568 0.4864 0.043 Uiso 1 1 calc R . . C2 C 0.6912(7) 0.9910(13) 0.4610(8) 0.051(5) Uiso 1 1 d G . . H2 H 0.7290 0.9808 0.5102 0.061 Uiso 1 1 calc R . . C3 C 0.7350(7) 1.1425(13) 0.4033(8) 0.049(5) Uiso 1 1 d G . . H3 H 0.8017 1.2392 0.4140 0.059 Uiso 1 1 calc R . . C4 C 0.6814(7) 1.1527(10) 0.3297(8) 0.034(4) Uiso 1 1 d G . . H4 H 0.7127 1.2535 0.2912 0.041 Uiso 1 1 calc R . . C5 C 0.5606(7) 1.1525(11) 0.1724(8) 0.040(5) Uiso 1 1 d G . . H5 H 0.6276 1.2477 0.1788 0.048 Uiso 1 1 calc R . . C6 C 0.5009(7) 1.1443(13) 0.1007(8) 0.045(5) Uiso 1 1 d G . . H6 H 0.5286 1.2316 0.0591 0.054 Uiso 1 1 calc R . . C7 C 0.4000(7) 1.0083(13) 0.0892(8) 0.056(5) Uiso 1 1 d G . . H7 H 0.3604 1.0054 0.0405 0.067 Uiso 1 1 calc R . . C8 C 0.3600(7) 0.8804(11) 0.1497(8) 0.039(5) Uiso 1 1 d G . . H8 H 0.2923 0.7911 0.1421 0.046 Uiso 1 1 calc R . . C9 C 0.3761(7) 0.7390(11) 0.2875(8) 0.028(4) Uiso 1 1 d G . . H9 H 0.3083 0.6507 0.2796 0.033 Uiso 1 1 calc R . . C10 C 0.4322(7) 0.7323(11) 0.3578(8) 0.039(5) Uiso 1 1 d G . . H10 H 0.4030 0.6373 0.3980 0.047 Uiso 1 1 calc R . . C11 C 0.5355(7) 0.8682(8) 0.3720(8) 0.038(4) Uiso 1 1 d G . . C12 C 0.5813(7) 1.0150(7) 0.3122(8) 0.027(4) Uiso 1 1 d G . . C13 C 0.5212(7) 1.0186(7) 0.2355(8) 0.028(4) Uiso 1 1 d G . . C14 C 0.4185(7) 0.8789(8) 0.2242(8) 0.031(4) Uiso 1 1 d G . . _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 C1 C2 1.3448 . ? C1 C11 1.4166 . ? C2 C3 1.3720 . ? C3 C4 1.3748 . ? C4 C12 1.3863 . ? C5 C6 1.3767 . ? C5 C13 1.3965 . ? C6 C7 1.3901 . ? C7 C8 1.3525 . ? C8 C14 1.4115 . ? C9 C10 1.3379 . ? C9 C14 1.4256 . ? C10 C11 1.4184 . ? C11 C12 1.4088 . ? C12 C13 1.4539 . ? C13 C14 1.4164 . ? 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 C1 C11 120.5 . . ? C1 C2 C3 120.5 . . ? C2 C3 C4 120.7 . . ? C3 C4 C12 120.9 . . ? C6 C5 C13 120.3 . . ? C5 C6 C7 121.3 . . ? C8 C7 C6 119.2 . . ? C7 C8 C14 121.7 . . ? C10 C9 C14 121.3 . . ? C9 C10 C11 120.9 . . ? C12 C11 C1 119.2 . . ? C12 C11 C10 120.7 . . ? C1 C11 C10 120.2 . . ? C4 C12 C11 118.2 . . ? C4 C12 C13 123.2 . . ? C11 C12 C13 118.6 . . ? C5 C13 C14 118.6 . . ? C5 C13 C12 122.7 . . ? C14 C13 C12 118.6 . . ? C8 C14 C13 118.8 . . ? C8 C14 C9 121.2 . . ? C13 C14 C9 120.0 . . ? _diffrn_measured_fraction_theta_max 0.363 _diffrn_reflns_theta_full 23.24 _diffrn_measured_fraction_theta_full 0.363 _refine_diff_density_max 0.244 _refine_diff_density_min -0.178 _refine_diff_density_rms 0.058 data_CRYSTALS_cif _database_code_depnum_ccdc_archive 'CCDC 237776' _audit_creation_date 04-04-16 _audit_creation_method CRYSTALS_ver_12.21 # fran02 in P2(1)/c _publ_section_exptl_refinement # see also _refine_ls_hydrogen for refinement keywords. ; H atoms placed geometrically after each cycle ; _chemical_name_systematic ? _chemical_melting_point ? _refine_ls_matrix_type full _atom_sites_solution_primary 'Global optimisation' _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment noref # General computing #============================================================= _computing_structure_refinement ; CRYSTALS (Betteridge et al 2003) ; _computing_publication_material ; CRYSTALS (Betteridge et al 2003) ; _computing_molecular_graphics ; CAMERON (Watkin et al 1996) ; #============================================================= _cell_length_a 6.6840(12) _cell_angle_alpha 90 _cell_length_b 12.475(7) _cell_angle_beta 107.387(19) _cell_length_c 10.736(4) _cell_angle_gamma 90 _cell_volume 854.3(6) _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 ' 0.0033 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 '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 '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_IV_Table_2.2B _cell_formula_units_Z 4 _chemical_formula_sum ' C8 H13 N1 O4 ' _chemical_formula_moiety ' C8 H13 N1 O4 ' _chemical_compound_source ; ? ; _chemical_formula_weight 187.20 _cell_measurement_reflns_used 139 _cell_measurement_theta_min 3 _cell_measurement_theta_max 23 _cell_measurement_temperature 293 _exptl_crystal_description ' block ' _exptl_crystal_colour ' colourless ' _exptl_crystal_size_min 0.05 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_max 0.18 _exptl_crystal_density_diffrn 1.455 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 400 _exptl_absorpt_coefficient_mu 0.117 _diffrn_measurement_device_type ; Bruker SMART APEX CCD ; _diffrn_radiation_monochromator graphite _computing_data_collection ; SMART (Siemens, 1993) ; _computing_data_reduction ; SAINT (Siemens ,1995) ; _computing_cell_refinement ; SAINT (Siemens ,1995) ; _computing_structure_solution ; USER DEFINED STRUCTURE SOLUTION ; _diffrn_measurement_method \w _exptl_absorpt_correction_type 'Empirical & multi-scan' _exptl_absorpt_process_details ; SHADE (Parsons, 2004) SADABS (Siemens, 1996) The following data are from Sadabs: ; _exptl_absorpt_correction_T_min 0.108 _exptl_absorpt_correction_T_max 1.000 # Sheldrick geometric definitions 0.99 0.99 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 293 _diffrn_reflns_number 895 _reflns_number_total 339 # Number of reflections with Friedels Law is 339 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 789 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_av_R_equivalents 0.0880 _diffrn_reflns_reduction_process ; 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 2.493 _diffrn_reflns_theta_max 19.293 _diffrn_measured_fraction_theta_max 0.426 _diffrn_reflns_theta_full 14.469 _diffrn_measured_fraction_theta_full 0.544 #_diffrn_reflns_limit_h_min -6 #_diffrn_reflns_limit_h_max 6 #_diffrn_reflns_limit_k_min 0 #_diffrn_reflns_limit_k_max 9 #_diffrn_reflns_limit_l_min 0 #_diffrn_reflns_limit_l_max 9 _reflns_limit_h_min -6 _reflns_limit_h_max 6 _reflns_limit_k_min 0 _reflns_limit_k_max 9 _reflns_limit_l_min 0 _reflns_limit_l_max 9 _refine_diff_density_min -0.24 _refine_diff_density_max 0.22 _refine_ls_number_reflns 334 _refine_ls_number_restraints 37 _refine_ls_number_parameters 53 #_refine_ls_R_factor_ref 0.1406 _refine_ls_wR_factor_ref 0.2419 _refine_ls_goodness_of_fit_ref 1.0001 #_reflns_number_all 334 _refine_ls_R_factor_all 0.1406 _refine_ls_wR_factor_all 0.2419 # 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 180 _refine_ls_R_factor_gt 0.0860 _refine_ls_wR_factor_gt 0.2061 _refine_ls_shift/su_max 0.000275 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; p=P(6)*max(Fo^2^,0) + (1-P(6))Fc^2^ Method = SHELXL 97 (Sheldrick, 1997) W = 1. / [Sigma^2^(F*)+(P(1)p)^2^+P(2)p+P(4)+P(5)Sin(theta) ] P(i) are: 0.119 3.04 0.00 0.00 0.00 0.333 ; _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.68890 ## -------------------REFERENCES ----------------------## ## Insert your own references - in alphabetic order _publ_section_references ; User-defined structure solution reference Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K., Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Siemens Industrial Automation, Inc (1993) SMART: Area-Detector Software Package; Madison, WI. Siemens Industrial Automation, Inc (1995). SAINT: Area-Detector Integration Software.; Madison, WI. Siemens Industrial Automation, Inc (1996). SADABS: Area-Detector Absorption Correction;: Madison, WI. Sheldrick, G.M. (1997). SHELXL-97. Program for the refinement of crystal structures. Univ. of Gottingen, Federal Republic of 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 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_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens C1 C 0.3616(17) 0.1865(7) 0.1259(8) 0.027(3) 1.0000 Uiso D . . . . . C2 C 0.3708(18) 0.0943(8) 0.2022(8) 0.040(4) 1.0000 Uiso D . . . . . C3 C 0.3101(16) -0.0035(8) 0.1420(9) 0.033(4) 1.0000 Uiso D . . . . . C4 C 0.2464(15) -0.0113(7) 0.0073(8) 0.028(4) 1.0000 Uiso D . . . . . C5 C 0.2354(18) 0.0812(8) -0.0673(8) 0.035(4) 1.0000 Uiso D . . . . . C6 C 0.292(2) 0.1789(8) -0.0081(9) 0.041(4) 1.0000 Uiso D . . . . . O7 O 0.4218(13) 0.2836(8) 0.1874(9) 0.052(3) 1.0000 Uiso D . . . . . N8 N 0.1831(14) -0.1071(7) -0.0643(8) 0.038(3) 1.0000 Uiso D . . . . . C9 C 0.1918(18) -0.2087(7) -0.0236(8) 0.036(4) 1.0000 Uiso D . . . . . O10 O 0.2643(12) -0.2365(9) 0.0913(9) 0.047(3) 1.0000 Uiso D . . . . . C11 C 0.1087(18) -0.2900(10) -0.1315(12) 0.042(4) 1.0000 Uiso D . . . . . O12 O 0.6795(13) 0.5424(10) 0.9727(9) 0.053(3) 1.0000 Uiso . . . . . . O13 O 0.0681(13) 0.5800(10) 0.1614(9) 0.056(3) 1.0000 Uiso . . . . . . H2 H 0.4167 0.0988 0.2917 0.0480 1.0000 Uiso . . . . . . H3 H 0.3122 -0.0638 0.1919 0.0400 1.0000 Uiso . . . . . . H5 H 0.1893 0.0768 -0.1568 0.0423 1.0000 Uiso . . . . . . H6 H 0.2840 0.2394 -0.0583 0.0494 1.0000 Uiso . . . . . . H7 H 0.5490 0.2799 0.2342 0.0778 1.0000 Uiso . . . . . . H8 H 0.1306 -0.0986 -0.1462 0.0454 1.0000 Uiso . . . . . . H111 H 0.1206 -0.3600 -0.0949 0.0632 1.0000 Uiso . . . . . . H112 H 0.1881 -0.2862 -0.1915 0.0632 1.0000 Uiso . . . . . . H113 H -0.0341 -0.2751 -0.1756 0.0632 1.0000 Uiso . . . . . . _refine_ls_extinction_method None 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 . 1.403(8) yes C1 . C6 . 1.376(8) yes C1 . O7 . 1.380(8) yes C2 . C3 . 1.384(8) yes C2 . H2 . 0.919 no C3 . C4 . 1.384(8) yes C3 . H3 . 0.921 no C4 . C5 . 1.393(8) yes C4 . N8 . 1.416(8) yes C5 . C6 . 1.375(8) yes C5 . H5 . 0.920 no C6 . H6 . 0.919 no O7 . H7 . 0.850 no N8 . C9 . 1.337(8) yes N8 . H8 . 0.850 no C9 . O10 . 1.233(8) yes C9 . C11 . 1.514(9) yes C11 . H111 . 0.951 no C11 . H112 . 0.951 no C11 . H113 . 0.949 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 C2 . C1 . C6 . 119.7(5) yes C2 . C1 . O7 . 119.0(6) yes C6 . C1 . O7 . 121.3(6) yes C1 . C2 . C3 . 119.7(6) yes C1 . C2 . H2 . 120.183 no C3 . C2 . H2 . 120.118 no C2 . C3 . C4 . 120.3(6) yes C2 . C3 . H3 . 119.868 no C4 . C3 . H3 . 119.804 no C3 . C4 . C5 . 119.3(5) yes C3 . C4 . N8 . 125.1(6) yes C5 . C4 . N8 . 115.5(6) yes C4 . C5 . C6 . 120.6(6) yes C4 . C5 . H5 . 119.682 no C6 . C5 . H5 . 119.745 no C1 . C6 . C5 . 120.3(6) yes C1 . C6 . H6 . 119.872 no C5 . C6 . H6 . 119.834 no C1 . O7 . H7 . 109.402 no C4 . N8 . C9 . 130.3(6) yes C4 . N8 . H8 . 114.873 no C9 . N8 . H8 . 114.853 no N8 . C9 . O10 . 124.0(6) yes N8 . C9 . C11 . 114.5(6) yes O10 . C9 . C11 . 121.4(7) yes C9 . C11 . H111 . 109.480 no C9 . C11 . H112 . 109.479 no H111 . C11 . H112 . 109.336 no C9 . C11 . H113 . 109.558 no H111 . C11 . H113 . 109.501 no H112 . C11 . H113 . 109.473 no