# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_requested_category FO _publ_contact_author_name 'Sylvie Derien' _publ_contact_author_email ' derien@univ-rennes1.fr' loop_ _publ_author_name 'Sylvie Derien' 'Thierry Roisnel' data_HK1_Cl _database_code_depnum_ccdc_archive 'CCDC 890488' #TrackingRef '12422_web_deposit_cif_file_0_sylviederien_1341482078.RXcompound 2a.cif' _audit_creation_date 2012-01-09T09:12:45-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C16 H13 Cl' _chemical_formula_sum 'C16 H13 Cl' _chemical_formula_weight 240.71 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration ad #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 5.6950(3) _cell_length_b 7.5345(5) _cell_length_c 28.7029(17) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1231.61(13) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 7560 _cell_measurement_theta_min 2.8 _cell_measurement_theta_max 27.41 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.11 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.03 _exptl_crystal_density_diffrn 1.298 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 504 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.283 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_absorpt_correction_T_min 0.898 _exptl_absorpt_correction_T_max 0.992 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_measurement_device_type 'APEXII, Bruker-AXS' _diffrn_measurement_method 'CCD rotation images, thin slices' _diffrn_detector 'CCD plate' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0401 _diffrn_reflns_av_unetI/netI 0.029 _diffrn_reflns_number 19579 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 3.44 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _reflns_number_total 2831 _reflns_number_gt 2540 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker APEX2 (Bruker, 2006)' _computing_cell_refinement 'Bruker APEX2 (Bruker, 2006)' _computing_data_reduction 'Bruker APEX2 (Bruker, 2006)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material ; WinGX publication routines (Farrugia, 1999), CRYSCAL (T. Roisnel, local program) ; #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0396P)^2^+0.2037P] 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_number_reflns 2831 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0397 _refine_ls_R_factor_gt 0.0326 _refine_ls_wR_factor_ref 0.077 _refine_ls_wR_factor_gt 0.0738 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _refine_ls_shift/su_max 0.008 _refine_ls_shift/su_mean 0.001 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.03(6) _refine_diff_density_max 0.244 _refine_diff_density_min -0.204 _refine_diff_density_rms 0.04 _iucr_refine_instructions_details ; .res file for SHELXL : job.res ................................................................. TITL import in P 21 21 21 CELL 0.71073 5.6950 7.5345 28.7029 90.000 90.000 90.000 ZERR 4.00 0.0003 0.0005 0.0017 0.000 0.000 0.000 LATT -1 SYMM 1/2 - X, - Y, 1/2 + Z SYMM 1/2 + X, 1/2 - Y, - Z SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H CL UNIT 64 52 4 MERG 2 FMAP 2 PLAN 20 ACTA BOND $H CONF LIST 4 WPDB -2 L.S. 4 TEMP -123.00 WGHT 0.039600 0.203700 FVAR 0.79044 C1 1 0.876979 0.916247 0.003140 11.00000 0.02425 0.02641 = 0.02905 0.00148 0.00092 -0.00131 AFIX 43 H1 2 0.744636 0.861232 0.017189 11.00000 -1.20000 AFIX 0 C2 1 0.898137 0.917202 -0.044961 11.00000 0.03189 0.02961 = 0.02779 -0.00292 -0.00437 0.00007 AFIX 43 H2 2 0.780570 0.862894 -0.063618 11.00000 -1.20000 AFIX 0 C3 1 1.090533 0.997242 -0.065994 11.00000 0.03845 0.03112 = 0.02332 0.00001 0.00249 0.00375 AFIX 43 H3 2 1.104930 0.997638 -0.098968 11.00000 -1.20000 AFIX 0 C4 1 1.261038 1.076356 -0.038696 11.00000 0.03118 0.02956 = 0.03325 0.00178 0.00763 -0.00374 AFIX 43 H4 2 1.392537 1.131482 -0.053025 11.00000 -1.20000 AFIX 0 C5 1 1.241324 1.075753 0.009483 11.00000 0.02674 0.02743 = 0.03027 -0.00270 0.00097 -0.00390 AFIX 43 H5 2 1.359731 1.130312 0.027879 11.00000 -1.20000 AFIX 0 C6 1 1.048408 0.995431 0.031279 11.00000 0.02552 0.02076 = 0.02619 0.00008 0.00095 0.00146 C7 1 1.036684 0.996925 0.082295 11.00000 0.02670 0.02562 = 0.02672 -0.00234 -0.00179 -0.00089 AFIX 43 H7 2 1.170524 1.042860 0.097943 11.00000 -1.20000 AFIX 0 C8 1 0.860028 0.941349 0.109628 11.00000 0.02423 0.02523 = 0.02756 -0.00177 -0.00090 -0.00050 AFIX 43 H8 2 0.720519 0.897729 0.095551 11.00000 -1.20000 AFIX 0 C9 1 0.876198 0.946036 0.159908 11.00000 0.02179 0.02367 = 0.02907 -0.00166 -0.00057 -0.00040 AFIX 43 H9 2 1.014262 0.998702 0.172315 11.00000 -1.20000 AFIX 0 C10 1 0.720678 0.885336 0.191264 11.00000 0.01763 0.01962 = 0.02857 -0.00493 -0.00124 -0.00034 C11 1 0.751747 0.884066 0.242473 11.00000 0.02229 0.01572 = 0.02608 -0.00253 -0.00013 0.00334 C12 1 0.953541 0.960223 0.262421 11.00000 0.02312 0.02812 = 0.03041 -0.00004 0.00257 -0.00393 AFIX 43 H12 2 1.067023 1.015089 0.242900 11.00000 -1.20000 AFIX 0 C13 1 0.989068 0.956296 0.310198 11.00000 0.02667 0.02954 = 0.03026 -0.00190 -0.00606 -0.00075 AFIX 43 H13 2 1.126510 1.008148 0.323103 11.00000 -1.20000 AFIX 0 C14 1 0.825484 0.877285 0.339194 11.00000 0.03497 0.02629 = 0.02478 0.00101 -0.00026 0.00568 AFIX 43 H14 2 0.850388 0.875069 0.371916 11.00000 -1.20000 AFIX 0 C15 1 0.625220 0.801405 0.320342 11.00000 0.03014 0.02737 = 0.02966 0.00196 0.00475 0.00002 AFIX 43 H15 2 0.512780 0.746842 0.340156 11.00000 -1.20000 AFIX 0 C16 1 0.588665 0.805056 0.272416 11.00000 0.02109 0.02314 = 0.03307 -0.00221 0.00273 -0.00043 AFIX 43 H16 2 0.450611 0.753004 0.259828 11.00000 -1.20000 AFIX 0 CL1 3 0.459086 0.791043 0.171002 11.00000 0.02454 0.04864 = 0.02977 -0.00687 -0.00051 -0.01166 HKLF 4 REM import in P 21 21 21 REM R1 = 0.0326 for 2540 Fo > 4sig(Fo) and 0.0397 for all 2831 data REM 154 parameters refined using 0 restraints END WGHT 0.0322 0.2229 REM Highest difference peak 0.24, deepest hole -0.20, 1-sigma level 0.04 Q1 1 0.9558 0.7198 0.3266 11.00000 0.05 0.24 Q2 1 1.0787 1.1629 0.1674 11.00000 0.05 0.23 Q3 1 0.6472 0.8953 0.2586 11.00000 0.05 0.16 Q4 1 0.7271 0.9000 0.2190 11.00000 0.05 0.16 Q5 1 1.0492 0.9991 0.0563 11.00000 0.05 0.16 Q6 1 1.3295 1.0454 0.0892 11.00000 0.05 0.16 Q7 1 0.7367 0.9783 0.1747 11.00000 0.05 0.16 Q8 1 1.2244 0.9870 -0.0543 11.00000 0.05 0.15 Q9 1 1.4092 1.0590 0.0312 11.00000 0.05 0.15 Q10 1 0.9262 0.9994 0.0172 11.00000 0.05 0.15 Q11 1 1.4425 0.9583 0.0104 11.00000 0.05 0.14 Q12 1 0.9366 1.0028 0.2905 11.00000 0.05 0.14 Q13 1 0.3535 0.6551 0.1576 11.00000 0.05 0.14 Q14 1 1.6073 1.1047 -0.0433 11.00000 0.05 0.14 Q15 1 0.1970 0.7040 0.2430 11.00000 0.05 0.13 Q16 1 1.1787 1.1493 0.3554 11.00000 0.05 0.13 Q17 1 1.0070 0.9147 0.0173 11.00000 0.05 0.13 Q18 1 1.3700 1.0219 0.2430 11.00000 0.05 0.13 Q19 1 1.2613 1.0256 -0.0152 11.00000 0.05 0.13 Q20 1 0.6970 0.7828 0.2582 11.00000 0.05 0.13 ; #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' 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 0.8770(3) 0.9162(2) 0.00314(6) 0.0266(4) Uani 1 1 d . . . H1 H 0.7446 0.8612 0.0172 0.032 Uiso 1 1 calc R . . C2 C 0.8981(3) 0.9172(2) -0.04496(6) 0.0298(4) Uani 1 1 d . . . H2 H 0.7806 0.8629 -0.0636 0.036 Uiso 1 1 calc R . . C3 C 1.0905(3) 0.9972(2) -0.06599(6) 0.0310(4) Uani 1 1 d . . . H3 H 1.1049 0.9976 -0.099 0.037 Uiso 1 1 calc R . . C4 C 1.2610(3) 1.0764(2) -0.03870(6) 0.0313(4) Uani 1 1 d . . . H4 H 1.3925 1.1315 -0.053 0.038 Uiso 1 1 calc R . . C5 C 1.2413(3) 1.0758(2) 0.00948(6) 0.0281(4) Uani 1 1 d . . . H5 H 1.3597 1.1303 0.0279 0.034 Uiso 1 1 calc R . . C6 C 1.0484(3) 0.9954(2) 0.03128(5) 0.0242(3) Uani 1 1 d . . . C7 C 1.0367(3) 0.9969(2) 0.08229(6) 0.0263(3) Uani 1 1 d . . . H7 H 1.1705 1.0429 0.0979 0.032 Uiso 1 1 calc R . . C8 C 0.8600(3) 0.9413(2) 0.10963(6) 0.0257(3) Uani 1 1 d . . . H8 H 0.7205 0.8977 0.0956 0.031 Uiso 1 1 calc R . . C9 C 0.8762(3) 0.9460(2) 0.15991(6) 0.0248(3) Uani 1 1 d . . . H9 H 1.0143 0.9987 0.1723 0.03 Uiso 1 1 calc R . . C10 C 0.7207(3) 0.8853(2) 0.19126(5) 0.0219(3) Uani 1 1 d . . . C11 C 0.7517(3) 0.8841(2) 0.24247(5) 0.0214(3) Uani 1 1 d . . . C12 C 0.9535(3) 0.9602(2) 0.26242(6) 0.0272(3) Uani 1 1 d . . . H12 H 1.067 1.0151 0.2429 0.033 Uiso 1 1 calc R . . C13 C 0.9891(3) 0.9563(2) 0.31020(6) 0.0288(4) Uani 1 1 d . . . H13 H 1.1265 1.0081 0.3231 0.035 Uiso 1 1 calc R . . C14 C 0.8255(3) 0.8773(2) 0.33919(6) 0.0287(4) Uani 1 1 d . . . H14 H 0.8504 0.8751 0.3719 0.034 Uiso 1 1 calc R . . C15 C 0.6252(3) 0.8014(2) 0.32034(5) 0.0291(4) Uani 1 1 d . . . H15 H 0.5128 0.7468 0.3402 0.035 Uiso 1 1 calc R . . C16 C 0.5887(3) 0.8051(2) 0.27242(6) 0.0258(3) Uani 1 1 d . . . H16 H 0.4506 0.753 0.2598 0.031 Uiso 1 1 calc R . . Cl1 Cl 0.45909(7) 0.79104(6) 0.171002(14) 0.03431(12) Uani 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 C1 0.0243(7) 0.0264(9) 0.0291(9) 0.0015(7) 0.0009(7) -0.0013(7) C2 0.0319(9) 0.0296(9) 0.0278(9) -0.0029(7) -0.0044(7) 0.0001(7) C3 0.0384(10) 0.0311(9) 0.0233(8) 0.0000(7) 0.0025(7) 0.0038(8) C4 0.0312(9) 0.0296(9) 0.0332(9) 0.0018(8) 0.0076(7) -0.0037(7) C5 0.0267(8) 0.0274(9) 0.0303(9) -0.0027(7) 0.0010(7) -0.0039(7) C6 0.0255(7) 0.0208(8) 0.0262(8) 0.0001(6) 0.0010(7) 0.0015(7) C7 0.0267(7) 0.0256(8) 0.0267(8) -0.0023(7) -0.0018(7) -0.0009(7) C8 0.0242(7) 0.0252(9) 0.0276(8) -0.0018(7) -0.0009(7) -0.0005(7) C9 0.0218(7) 0.0237(8) 0.0291(9) -0.0017(7) -0.0006(6) -0.0004(6) C10 0.0176(7) 0.0196(8) 0.0286(8) -0.0049(6) -0.0012(6) -0.0003(6) C11 0.0223(7) 0.0157(8) 0.0261(8) -0.0025(6) -0.0001(6) 0.0033(6) C12 0.0231(7) 0.0281(9) 0.0304(9) 0.0000(7) 0.0026(7) -0.0039(7) C13 0.0267(9) 0.0295(9) 0.0303(8) -0.0019(7) -0.0061(7) -0.0007(7) C14 0.0350(9) 0.0263(9) 0.0248(9) 0.0010(7) -0.0003(7) 0.0057(7) C15 0.0301(7) 0.0274(8) 0.0297(9) 0.0020(8) 0.0048(7) 0.0000(7) C16 0.0211(7) 0.0231(8) 0.0331(8) -0.0022(7) 0.0027(6) -0.0004(6) Cl1 0.02454(17) 0.0486(3) 0.0298(2) -0.0069(2) -0.00051(16) -0.01166(18) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 1.386(2) . ? C1 C6 1.401(2) . ? C1 H1 0.95 . ? C2 C3 1.389(2) . ? C2 H2 0.95 . ? C3 C4 1.383(2) . ? C3 H3 0.95 . ? C4 C5 1.387(2) . ? C4 H4 0.95 . ? C5 C6 1.402(2) . ? C5 H5 0.95 . ? C6 C7 1.466(2) . ? C7 C8 1.343(2) . ? C7 H7 0.95 . ? C8 C9 1.447(2) . ? C8 H8 0.95 . ? C9 C10 1.343(2) . ? C9 H9 0.95 . ? C10 C11 1.480(2) . ? C10 Cl1 1.7500(15) . ? C11 C16 1.398(2) . ? C11 C12 1.406(2) . ? C12 C13 1.387(2) . ? C12 H12 0.95 . ? C13 C14 1.384(2) . ? C13 H13 0.95 . ? C14 C15 1.386(2) . ? C14 H14 0.95 . ? C15 C16 1.392(2) . ? C15 H15 0.95 . ? C16 H16 0.95 . ? 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 C6 120.78(16) . . ? C2 C1 H1 119.6 . . ? C6 C1 H1 119.6 . . ? C1 C2 C3 120.26(16) . . ? C1 C2 H2 119.9 . . ? C3 C2 H2 119.9 . . ? C4 C3 C2 119.66(15) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.2 . . ? C3 C4 C5 120.43(16) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? C4 C5 C6 120.64(16) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C1 C6 C5 118.22(15) . . ? C1 C6 C7 123.20(15) . . ? C5 C6 C7 118.57(15) . . ? C8 C7 C6 127.98(16) . . ? C8 C7 H7 116 . . ? C6 C7 H7 116 . . ? C7 C8 C9 121.84(16) . . ? C7 C8 H8 119.1 . . ? C9 C8 H8 119.1 . . ? C10 C9 C8 128.19(15) . . ? C10 C9 H9 115.9 . . ? C8 C9 H9 115.9 . . ? C9 C10 C11 126.07(14) . . ? C9 C10 Cl1 118.49(12) . . ? C11 C10 Cl1 115.41(11) . . ? C16 C11 C12 117.79(14) . . ? C16 C11 C10 122.24(14) . . ? C12 C11 C10 119.95(14) . . ? C13 C12 C11 120.88(15) . . ? C13 C12 H12 119.6 . . ? C11 C12 H12 119.6 . . ? C14 C13 C12 120.38(16) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C13 C14 C15 119.78(15) . . ? C13 C14 H14 120.1 . . ? C15 C14 H14 120.1 . . ? C14 C15 C16 120.06(15) . . ? C14 C15 H15 120 . . ? C16 C15 H15 120 . . ? C15 C16 C11 121.10(15) . . ? C15 C16 H16 119.4 . . ? C11 C16 H16 119.4 . . ? 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 C6 C1 C2 C3 -0.1(3) . . . . ? C1 C2 C3 C4 -0.1(3) . . . . ? C2 C3 C4 C5 0.2(3) . . . . ? C3 C4 C5 C6 -0.1(3) . . . . ? C2 C1 C6 C5 0.1(2) . . . . ? C2 C1 C6 C7 -179.35(16) . . . . ? C4 C5 C6 C1 0.0(2) . . . . ? C4 C5 C6 C7 179.46(15) . . . . ? C1 C6 C7 C8 -6.6(3) . . . . ? C5 C6 C7 C8 173.96(16) . . . . ? C6 C7 C8 C9 178.08(15) . . . . ? C7 C8 C9 C10 -175.57(17) . . . . ? C8 C9 C10 C11 176.25(15) . . . . ? C8 C9 C10 Cl1 -1.4(2) . . . . ? C9 C10 C11 C16 -174.67(15) . . . . ? Cl1 C10 C11 C16 3.0(2) . . . . ? C9 C10 C11 C12 3.7(2) . . . . ? Cl1 C10 C11 C12 -178.57(11) . . . . ? C16 C11 C12 C13 0.2(2) . . . . ? C10 C11 C12 C13 -178.28(15) . . . . ? C11 C12 C13 C14 -0.1(2) . . . . ? C12 C13 C14 C15 0.1(2) . . . . ? C13 C14 C15 C16 -0.1(2) . . . . ? C14 C15 C16 C11 0.2(2) . . . . ? C12 C11 C16 C15 -0.2(2) . . . . ? C10 C11 C16 C15 178.21(15) . . . . ? # Attachment '12423_web_deposit_cif_file_1_sylviederien_1341482078.RXcompound 2i.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2012-04-20 at 17:30:39 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.4 # Request file : d:\progs\wingx\files\archive.dat # CIF files read : job struct data_HKPCN1 _database_code_depnum_ccdc_archive 'CCDC 890489' #TrackingRef '12423_web_deposit_cif_file_1_sylviederien_1341482078.RXcompound 2i.cif' _audit_creation_date 2012-04-20T17:30:39-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C18 H11 Cl N2' _chemical_formula_sum 'C18 H11 Cl N2' _chemical_formula_weight 290.74 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _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 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 11.0766(6) _cell_length_b 10.0123(6) _cell_length_c 13.7838(7) _cell_angle_alpha 90 _cell_angle_beta 108.455(2) _cell_angle_gamma 90 _cell_volume 1450.04(14) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2022 _cell_measurement_theta_min 2.56 _cell_measurement_theta_max 26.47 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.58 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.12 _exptl_crystal_density_diffrn 1.332 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 600 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.257 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_absorpt_correction_T_min 0.808 _exptl_absorpt_correction_T_max 0.970 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_measurement_device_type 'APEXII, Bruker-AXS' _diffrn_measurement_method 'CCD rotation images, thin slices' _diffrn_detector 'CCD plate' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0487 _diffrn_reflns_av_unetI/netI 0.0619 _diffrn_reflns_number 10141 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.11 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.994 _reflns_number_total 3304 _reflns_number_gt 2346 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker APEX2 (Bruker, 2006)' _computing_cell_refinement 'Bruker APEX2 (Bruker, 2006)' _computing_data_reduction 'Bruker APEX2 (Bruker, 2006)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material ; WinGX publication routines (Farrugia, 1999), CRYSCAL (T. Roisnel, local program) ; #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0492P)^2^+0.0188P] 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_number_reflns 3304 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0756 _refine_ls_R_factor_gt 0.0473 _refine_ls_wR_factor_ref 0.1144 _refine_ls_wR_factor_gt 0.1036 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _refine_ls_shift/su_max 0.014 _refine_ls_shift/su_mean 0.002 _refine_diff_density_max 0.227 _refine_diff_density_min -0.311 _refine_diff_density_rms 0.048 _iucr_refine_instructions_details ; .res file for SHELXL : job.res ................................................................. TITL import in P 21/c CELL 0.71073 11.0766 10.0123 13.7838 90.000 108.455 90.000 ZERR 4.00 0.0006 0.0006 0.0007 0.000 0.002 0.000 LATT 1 SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H N CL UNIT 72 44 8 4 MERG 2 FMAP 2 PLAN 20 ACTA BOND $H CONF LIST 4 WPDB -2 L.S. 4 TEMP -123.00 WGHT 0.049200 0.018800 FVAR 0.92375 CL1 4 0.668359 -0.045573 0.276996 11.00000 0.05413 0.02376 = 0.04040 0.00572 0.00153 0.00364 N1 3 0.371455 0.387208 -0.201459 11.00000 0.05520 0.04157 = 0.02834 0.00084 0.00287 0.00531 C2 1 0.426527 0.344673 -0.123296 11.00000 0.03931 0.02821 = 0.02540 -0.00362 0.00751 0.00252 C3 1 0.492991 0.291116 -0.023105 11.00000 0.02961 0.02768 = 0.02272 -0.00278 0.00701 0.00587 C4 1 0.605296 0.349109 0.038276 11.00000 0.03826 0.02534 = 0.02436 -0.00146 0.01134 -0.00139 AFIX 43 H4 2 0.639321 0.425153 0.014894 11.00000 -1.20000 AFIX 0 C5 1 0.667283 0.295377 0.133710 11.00000 0.02868 0.02681 = 0.02534 -0.00366 0.00628 -0.00086 AFIX 43 H5 2 0.745118 0.333556 0.174980 11.00000 -1.20000 AFIX 0 C6 1 0.616643 0.186105 0.169644 11.00000 0.02711 0.02494 = 0.02496 -0.00226 0.00740 0.00576 C7 1 0.503934 0.128574 0.106786 11.00000 0.03170 0.02742 = 0.03076 0.00206 0.00843 -0.00198 AFIX 43 H7 2 0.469188 0.053030 0.130158 11.00000 -1.20000 AFIX 0 C8 1 0.442737 0.180660 0.011036 11.00000 0.02680 0.03341 = 0.02826 -0.00295 0.00472 -0.00095 AFIX 43 H8 2 0.366371 0.140866 -0.031326 11.00000 -1.20000 AFIX 0 C9 1 0.682675 0.128397 0.271404 11.00000 0.03078 0.02331 = 0.02902 0.00402 0.00641 0.00412 N11 3 0.940134 1.027263 0.626455 11.00000 0.04897 0.03794 = 0.04068 -0.00252 0.00712 0.00043 C12 1 0.923560 0.916786 0.604694 11.00000 0.03009 0.03857 = 0.02857 0.00084 0.00234 0.00364 C13 1 0.900831 0.779330 0.573309 11.00000 0.02370 0.03228 = 0.02989 0.00046 0.00297 0.00202 C14 1 0.867751 0.748582 0.469139 11.00000 0.02977 0.03335 = 0.02513 0.00572 0.00138 0.00339 AFIX 43 H14 2 0.861909 0.817610 0.420576 11.00000 -1.20000 AFIX 0 C15 1 0.843752 0.618659 0.437168 11.00000 0.02688 0.03553 = 0.02004 0.00136 0.00060 0.00171 AFIX 43 H15 2 0.821032 0.599016 0.366222 11.00000 -1.20000 AFIX 0 C16 1 0.851935 0.514582 0.506467 11.00000 0.02063 0.03329 = 0.02332 -0.00114 0.00207 0.00251 C17 1 0.888453 0.547135 0.611185 11.00000 0.02805 0.03546 = 0.02315 0.00595 0.00368 0.00256 AFIX 43 H17 2 0.897260 0.477841 0.660026 11.00000 -1.20000 AFIX 0 C18 1 0.911717 0.677440 0.644393 11.00000 0.03014 0.03782 = 0.02187 -0.00034 0.00302 0.00132 AFIX 43 H18 2 0.935014 0.697554 0.715291 11.00000 -1.20000 AFIX 0 C19 1 0.827224 0.375699 0.474657 11.00000 0.02487 0.03002 = 0.02608 0.00541 0.00431 0.00150 AFIX 43 H19 2 0.858175 0.309612 0.525995 11.00000 -1.20000 AFIX 0 C20 1 0.764835 0.331963 0.379648 11.00000 0.02559 0.03051 = 0.02601 0.00251 0.00627 0.00303 AFIX 43 H20 2 0.731246 0.394437 0.325989 11.00000 -1.20000 AFIX 0 C21 1 0.748658 0.190479 0.358804 11.00000 0.02852 0.02981 = 0.02756 0.00710 0.00586 0.00535 AFIX 43 H21 2 0.790289 0.133411 0.414391 11.00000 -1.20000 HKLF 4 REM import in P 21/c REM R1 = 0.0473 for 2346 Fo > 4sig(Fo) and 0.0756 for all 3304 data REM 190 parameters refined using 0 restraints END WGHT 0.0440 0.1023 REM Highest difference peak 0.23, deepest hole -0.31, 1-sigma level 0.05 Q1 1 0.9233 0.7206 0.6028 11.00000 0.05 0.23 Q2 1 0.8989 0.5296 0.5580 11.00000 0.05 0.22 Q3 1 0.6619 0.1633 0.2152 11.00000 0.05 0.22 Q4 1 0.8174 0.4561 0.4810 11.00000 0.05 0.20 Q5 1 0.5564 0.1764 0.1501 11.00000 0.05 0.20 Q6 1 0.7795 0.2644 0.3488 11.00000 0.05 0.20 Q7 1 0.4773 0.2232 -0.0219 11.00000 0.05 0.20 Q8 1 0.9247 0.9862 0.5716 11.00000 0.05 0.19 Q9 1 0.6183 0.3338 0.0876 11.00000 0.05 0.19 Q10 1 0.9070 0.9633 0.6437 11.00000 0.05 0.19 Q11 1 0.6647 0.0583 0.2792 11.00000 0.05 0.19 Q12 1 0.5435 0.3211 0.0016 11.00000 0.05 0.19 Q13 1 0.5953 -0.0640 0.2088 11.00000 0.05 0.18 Q14 1 0.9491 0.6882 0.6890 11.00000 0.05 0.18 Q15 1 0.8558 0.7621 0.5322 11.00000 0.05 0.17 Q16 1 1.0013 0.9562 0.6053 11.00000 0.05 0.17 Q17 1 0.9110 0.7506 0.5285 11.00000 0.05 0.17 Q18 1 0.7556 0.1611 0.3140 11.00000 0.05 0.17 Q19 1 0.7948 0.3536 0.4224 11.00000 0.05 0.17 Q20 1 0.9242 0.8326 0.5777 11.00000 0.05 0.17 ; #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.66836(5) -0.04557(5) 0.27700(3) 0.04258(18) Uani 1 1 d . . . N1 N 0.37145(16) 0.38721(18) -0.20146(11) 0.0441(5) Uani 1 1 d . . . C2 C 0.42653(18) 0.34467(19) -0.12330(13) 0.0316(4) Uani 1 1 d . . . C3 C 0.49299(17) 0.29112(18) -0.02310(12) 0.0270(4) Uani 1 1 d . . . C4 C 0.60530(17) 0.34911(19) 0.03828(12) 0.0290(4) Uani 1 1 d . . . H4 H 0.6393 0.4252 0.0149 0.035 Uiso 1 1 calc R . . C5 C 0.66728(17) 0.29538(18) 0.13371(12) 0.0275(4) Uani 1 1 d . . . H5 H 0.7451 0.3336 0.175 0.033 Uiso 1 1 calc R . . C6 C 0.61664(16) 0.18611(18) 0.16964(12) 0.0259(4) Uani 1 1 d . . . C7 C 0.50393(17) 0.12857(19) 0.10679(12) 0.0303(4) Uani 1 1 d . . . H7 H 0.4692 0.053 0.1302 0.036 Uiso 1 1 calc R . . C8 C 0.44274(17) 0.18066(19) 0.01104(12) 0.0304(4) Uani 1 1 d . . . H8 H 0.3664 0.1409 -0.0313 0.037 Uiso 1 1 calc R . . C9 C 0.68268(17) 0.12840(19) 0.27140(12) 0.0284(4) Uani 1 1 d . . . N11 N 0.94013(17) 1.02726(18) 0.62646(12) 0.0442(4) Uani 1 1 d . . . C12 C 0.92356(18) 0.9168(2) 0.60469(13) 0.0340(5) Uani 1 1 d . . . C13 C 0.90083(16) 0.77933(19) 0.57331(13) 0.0299(4) Uani 1 1 d . . . C14 C 0.86775(17) 0.7486(2) 0.46914(12) 0.0311(4) Uani 1 1 d . . . H14 H 0.8619 0.8176 0.4206 0.037 Uiso 1 1 calc R . . C15 C 0.84375(16) 0.61866(19) 0.43717(12) 0.0291(4) Uani 1 1 d . . . H15 H 0.821 0.599 0.3662 0.035 Uiso 1 1 calc R . . C16 C 0.85194(16) 0.51458(19) 0.50647(12) 0.0269(4) Uani 1 1 d . . . C17 C 0.88845(17) 0.54713(19) 0.61118(12) 0.0299(4) Uani 1 1 d . . . H17 H 0.8973 0.4778 0.66 0.036 Uiso 1 1 calc R . . C18 C 0.91172(16) 0.6774(2) 0.64439(12) 0.0312(4) Uani 1 1 d . . . H18 H 0.935 0.6976 0.7153 0.037 Uiso 1 1 calc R . . C19 C 0.82722(16) 0.37570(19) 0.47466(12) 0.0279(4) Uani 1 1 d . . . H19 H 0.8582 0.3096 0.526 0.033 Uiso 1 1 calc R . . C20 C 0.76484(16) 0.33196(19) 0.37965(12) 0.0278(4) Uani 1 1 d . . . H20 H 0.7312 0.3944 0.326 0.033 Uiso 1 1 calc R . . C21 C 0.74866(16) 0.19048(19) 0.35880(13) 0.0293(4) Uani 1 1 d . . . H21 H 0.7903 0.1334 0.4144 0.035 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 0.0541(4) 0.0238(3) 0.0404(3) 0.0057(2) 0.0015(2) 0.0036(2) N1 0.0552(12) 0.0416(11) 0.0283(8) 0.0008(8) 0.0029(8) 0.0053(9) C2 0.0393(11) 0.0282(11) 0.0254(9) -0.0036(8) 0.0075(8) 0.0025(9) C3 0.0296(10) 0.0277(10) 0.0227(8) -0.0028(7) 0.0070(7) 0.0059(8) C4 0.0383(11) 0.0253(10) 0.0244(8) -0.0015(7) 0.0113(8) -0.0014(8) C5 0.0287(10) 0.0268(10) 0.0253(8) -0.0037(7) 0.0063(7) -0.0009(8) C6 0.0271(10) 0.0249(10) 0.0250(8) -0.0023(7) 0.0074(7) 0.0058(8) C7 0.0317(10) 0.0274(10) 0.0308(9) 0.0021(8) 0.0084(8) -0.0020(8) C8 0.0268(10) 0.0334(11) 0.0283(9) -0.0029(8) 0.0047(8) -0.0009(9) C9 0.0308(10) 0.0233(10) 0.0290(9) 0.0040(7) 0.0064(8) 0.0041(8) N11 0.0490(11) 0.0379(11) 0.0407(9) -0.0025(8) 0.0071(8) 0.0004(9) C12 0.0301(11) 0.0386(12) 0.0286(9) 0.0008(9) 0.0023(8) 0.0036(9) C13 0.0237(10) 0.0323(11) 0.0299(9) 0.0005(8) 0.0030(8) 0.0020(8) C14 0.0298(10) 0.0334(11) 0.0251(9) 0.0057(8) 0.0014(7) 0.0034(9) C15 0.0269(10) 0.0355(11) 0.0200(8) 0.0014(8) 0.0006(7) 0.0017(9) C16 0.0206(9) 0.0333(11) 0.0233(8) -0.0011(8) 0.0021(7) 0.0025(8) C17 0.0281(10) 0.0355(11) 0.0231(8) 0.0059(8) 0.0037(7) 0.0026(9) C18 0.0301(10) 0.0378(11) 0.0219(8) -0.0003(8) 0.0030(8) 0.0013(9) C19 0.0249(9) 0.0300(11) 0.0261(8) 0.0054(8) 0.0043(7) 0.0015(8) C20 0.0256(10) 0.0305(11) 0.0260(9) 0.0025(8) 0.0063(7) 0.0030(8) C21 0.0285(10) 0.0298(11) 0.0276(9) 0.0071(8) 0.0059(8) 0.0053(8) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C9 1.7529(19) . ? N1 C2 1.139(2) . ? C2 C3 1.447(2) . ? C3 C8 1.386(3) . ? C3 C4 1.391(2) . ? C4 C5 1.385(2) . ? C4 H4 0.95 . ? C5 C6 1.390(2) . ? C5 H5 0.95 . ? C6 C7 1.399(2) . ? C6 C9 1.479(2) . ? C7 C8 1.381(2) . ? C7 H7 0.95 . ? C8 H8 0.95 . ? C9 C21 1.347(2) . ? N11 C12 1.146(2) . ? C12 C13 1.441(3) . ? C13 C18 1.393(2) . ? C13 C14 1.399(2) . ? C14 C15 1.372(3) . ? C14 H14 0.95 . ? C15 C16 1.397(2) . ? C15 H15 0.95 . ? C16 C17 1.408(2) . ? C16 C19 1.458(3) . ? C17 C18 1.380(3) . ? C17 H17 0.95 . ? C18 H18 0.95 . ? C19 C20 1.346(2) . ? C19 H19 0.95 . ? C20 C21 1.445(2) . ? C20 H20 0.95 . ? C21 H21 0.95 . ? 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 N1 C2 C3 178.24(19) . . ? C8 C3 C4 120.31(15) . . ? C8 C3 C2 118.83(16) . . ? C4 C3 C2 120.85(17) . . ? C5 C4 C3 119.64(17) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? C4 C5 C6 120.62(16) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C5 C6 C7 119.02(15) . . ? C5 C6 C9 120.75(15) . . ? C7 C6 C9 120.21(16) . . ? C8 C7 C6 120.55(17) . . ? C8 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? C7 C8 C3 119.84(16) . . ? C7 C8 H8 120.1 . . ? C3 C8 H8 120.1 . . ? C21 C9 C6 129.30(17) . . ? C21 C9 Cl1 116.76(13) . . ? C6 C9 Cl1 113.92(12) . . ? N11 C12 C13 177.8(2) . . ? C18 C13 C14 119.80(18) . . ? C18 C13 C12 121.36(16) . . ? C14 C13 C12 118.84(17) . . ? C15 C14 C13 119.96(17) . . ? C15 C14 H14 120 . . ? C13 C14 H14 120 . . ? C14 C15 C16 121.57(16) . . ? C14 C15 H15 119.2 . . ? C16 C15 H15 119.2 . . ? C15 C16 C17 117.62(17) . . ? C15 C16 C19 122.72(15) . . ? C17 C16 C19 119.65(16) . . ? C18 C17 C16 121.45(17) . . ? C18 C17 H17 119.3 . . ? C16 C17 H17 119.3 . . ? C17 C18 C13 119.58(16) . . ? C17 C18 H18 120.2 . . ? C13 C18 H18 120.2 . . ? C20 C19 C16 126.35(16) . . ? C20 C19 H19 116.8 . . ? C16 C19 H19 116.8 . . ? C19 C20 C21 120.36(16) . . ? C19 C20 H20 119.8 . . ? C21 C20 H20 119.8 . . ? C9 C21 C20 128.91(16) . . ? C9 C21 H21 115.5 . . ? C20 C21 H21 115.5 . . ? 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 C8 C3 C4 C5 0.4(3) . . . . ? C2 C3 C4 C5 -179.70(16) . . . . ? C3 C4 C5 C6 -1.6(3) . . . . ? C4 C5 C6 C7 1.9(3) . . . . ? C4 C5 C6 C9 179.91(16) . . . . ? C5 C6 C7 C8 -1.0(3) . . . . ? C9 C6 C7 C8 -179.02(16) . . . . ? C6 C7 C8 C3 -0.2(3) . . . . ? C4 C3 C8 C7 0.5(3) . . . . ? C2 C3 C8 C7 -179.41(16) . . . . ? C5 C6 C9 C21 36.6(3) . . . . ? C7 C6 C9 C21 -145.42(19) . . . . ? C5 C6 C9 Cl1 -144.89(15) . . . . ? C7 C6 C9 Cl1 33.1(2) . . . . ? C18 C13 C14 C15 1.3(3) . . . . ? C12 C13 C14 C15 -179.02(17) . . . . ? C13 C14 C15 C16 -0.3(3) . . . . ? C14 C15 C16 C17 -1.3(3) . . . . ? C14 C15 C16 C19 -179.87(16) . . . . ? C15 C16 C17 C18 1.9(3) . . . . ? C19 C16 C17 C18 -179.47(16) . . . . ? C16 C17 C18 C13 -1.0(3) . . . . ? C14 C13 C18 C17 -0.7(3) . . . . ? C12 C13 C18 C17 179.63(17) . . . . ? C15 C16 C19 C20 -17.8(3) . . . . ? C17 C16 C19 C20 163.67(17) . . . . ? C16 C19 C20 C21 179.22(16) . . . . ? C6 C9 C21 C20 5.5(3) . . . . ? Cl1 C9 C21 C20 -173.03(15) . . . . ? C19 C20 C21 C9 175.15(18) . . . . ?