# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 # Attachment '1-296K.cif' #------------------ SECTION 1. GLOBAL INFORMATION ---------------------------# data_global2 _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 #TrackingRef '1-296K.cif' #------------------ AUDIT DETAILS -------------------------------------------# _audit_creation_date 2011-09-30 _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 _audit_update_record ? _publ_contact_author_name 'Dejan-Kresimir Bucar' _publ_contact_author_address ;Department of Chemistry E555 Chemistry Building The University of Iowa Iowa City, IA 52242-1294 USA ; _publ_contact_author_fax 1-319-335-1270 _publ_contact_author_phone 1-319-335-3504 #============================================================================== # # TITLE AND AUTHOR LIST loop_ _publ_author_name _publ_author_address D.-K.Bucar ;Department of Chemistry E553 Chemistry Building The University of Iowa Iowa City, IA 52242-1294 USA ; A.Sen ;Department of Chemistry E553 Chemistry Building The University of Iowa Iowa City, IA 52242-1294 USA ; S.V.S.Mariappan ;Department of Chemistry E553 Chemistry Building The University of Iowa Iowa City, IA 52242-1294 USA ; L.R.MacGillivray ;Department of Chemistry E555 Chemistry Building The University of Iowa Iowa City, IA 52242-1294 USA ; _publ_contact_author_email dkb29@cam.ac.uk #------------------ SECTION 2. COMPOUND(S) DETAILS -------------------------# data_1-296K _database_code_depnum_ccdc_archive 'CCDC 809484' #TrackingRef '1-296K.cif' _audit_creation_date 2011-09-30T11:36:26-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_formula_sum 'C33.35 H30.05 Cl0.65 N2 O2' _chemical_formula_moiety ; C13.52 H11.56 Cl0.48 N, C13.83 H12.49 Cl0.17 N, C6 H6 O2 ; _chemical_formula_weight 513.89 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _cell_length_a 10.0708(11) _cell_length_b 10.4551(11) _cell_length_c 13.9967(15) _cell_angle_alpha 105.885(5) _cell_angle_beta 99.037(5) _cell_angle_gamma 92.659(5) _cell_volume 1393.6(3) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 25.35 _cell_measurement_reflns_used 5033 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.08 _exptl_crystal_density_diffrn 1.216 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 542.4 #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.136 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'HKL Scalepack (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.9476 _exptl_absorpt_correction_T_max 0.9892 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_reflns_av_R_equivalents 0.0253 _diffrn_reflns_av_unetI/netI 0.0421 _diffrn_reflns_number 8611 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 5.19 _diffrn_reflns_theta_max 25 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 0.988 _diffrn_measured_fraction_theta_max 0.988 _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD phi and omega scans' _diffrn_detector_area_resol_mean 9 _reflns_number_total 4843 _reflns_number_gt 2913 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL Denzo, Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL (Sheldrick, 2008)' _computing_molecular_graphics 'Rastop (Valadon, 2004)' _computing_publication_material 'WinGX (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # 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^ > 2\s(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. A total of 40 geometrical restraints (i.e. SIMU, DELU, SADI, DFIX, FLAT) and constraints (i.e. EADP) were utilised to model the 4-chlorophenyl and 4-methylphenyl groups. A checkCIF report listed several level-C alerts that are attributed to the significant thermal motions of the atoms at room temperature. The report also reveals a high ration of the maximum and minimum residual electron densities. This alert is ascribed to the occurrence of four pronounced electron density peaks in close proximity of the two of olefins, thus, indicating pedal-like motion of the olefins in the solid state (see: Harada, J.; Ogawa, K. Chem. Soc. Rev., 2009, 38, 2244). However, a reasonable model involving disordered -C=C- groups could not be achieved despite the extensive use of both restraints and constraints. ; _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^)+(0.1155P)^2^+0.0794P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 4843 _refine_ls_number_parameters 353 _refine_ls_number_restraints 40 _refine_ls_R_factor_all 0.1138 _refine_ls_R_factor_gt 0.0674 _refine_ls_wR_factor_ref 0.2142 _refine_ls_wR_factor_gt 0.1941 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_restrained_S_all 1.09 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.503 _refine_diff_density_min -0.226 _refine_diff_density_rms 0.033 #----------------------------------------------------------------------------# # 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' O O 0.0106 0.006 '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 0.4147(3) 0.0879(3) 0.1078(2) 0.0813(8) Uani 1 1 d . . . C2 C 0.4461(3) 0.1186(3) 0.2110(2) 0.0753(7) Uani 1 1 d . . . C3 C 0.3452(3) 0.1102(2) 0.26680(19) 0.0653(6) Uani 1 1 d U . . C4 C 0.2165(3) 0.0723(3) 0.2121(2) 0.0761(7) Uani 1 1 d . . . C5 C 0.1949(3) 0.0406(3) 0.1093(2) 0.0850(8) Uani 1 1 d . . . C6 C 0.3665(3) 0.1374(3) 0.3765(2) 0.0747(7) Uani 1 1 d U . . C7 C 0.4805(3) 0.1547(3) 0.4366(2) 0.0735(7) Uani 1 1 d U . . C8 C 0.5018(3) 0.17595(17) 0.54764(19) 0.0696(6) Uani 1 1 d DU A . C9 C 0.6316(3) 0.2063(2) 0.6016(2) 0.0785(7) Uani 1 1 d D . . C10 C 0.6571(3) 0.23051(18) 0.7049(2) 0.0840(8) Uani 1 1 d D A . C11 C 0.5540(3) 0.22510(12) 0.75717(19) 0.0779(8) Uani 1 1 d DU . . C12 C 0.4237(3) 0.19495(19) 0.7046(2) 0.0830(8) Uani 1 1 d D A . C13 C 0.3990(3) 0.1708(2) 0.6010(2) 0.0795(7) Uani 1 1 d DU . . C14 C 0.1883(4) 0.4044(4) 0.0491(3) 0.1058(10) Uani 1 1 d . . . C15 C 0.2341(4) 0.4335(3) 0.1498(3) 0.1000(10) Uani 1 1 d . . . C16 C 0.1516(4) 0.4054(3) 0.2118(2) 0.0861(8) Uani 1 1 d U . . C17 C 0.0222(4) 0.3465(3) 0.1655(2) 0.0910(9) Uani 1 1 d . . . C18 C -0.0155(4) 0.3200(3) 0.0625(3) 0.0941(9) Uani 1 1 d . . . C19 C 0.2061(4) 0.4399(3) 0.3211(2) 0.0994(10) Uani 1 1 d U . . C20 C 0.1520(4) 0.4133(3) 0.3876(3) 0.0957(9) Uani 1 1 d U . . C21 C 0.2054(3) 0.4486(2) 0.4982(2) 0.0839(7) Uani 1 1 d DU B . C22 C 0.3290(3) 0.5208(2) 0.5451(2) 0.0876(8) Uani 1 1 d DU . . C23 C 0.3730(3) 0.5506(2) 0.6487(2) 0.0856(8) Uani 1 1 d D B . C24 C 0.2924(3) 0.5076(2) 0.7082(2) 0.0804(8) Uani 1 1 d DU . . C25 C 0.1707(3) 0.4364(2) 0.6607(2) 0.0884(8) Uani 1 1 d D B . C26 C 0.1291(3) 0.4081(3) 0.5588(2) 0.0891(8) Uani 1 1 d D . . C27A C 0.3385(5) 0.5389(3) 0.8204(5) 0.1092(10) Uani 0.83 1 d PDU B 1 C27B C 0.5816(5) 0.2515(2) 0.8694(7) 0.1062(6) Uani 0.52 1 d PDU A 2 C28 C 0.8261(3) 0.0416(3) 0.20675(19) 0.0734(7) Uani 1 1 d . . . C29 C 0.8700(2) -0.0825(3) 0.17028(18) 0.0680(7) Uani 1 1 d . . . C30 C 0.9437(3) -0.1426(3) 0.23566(19) 0.0751(7) Uani 1 1 d . . . C31 C 0.9721(4) -0.0777(4) 0.3375(2) 0.0963(9) Uani 1 1 d U . . C32 C 0.9272(4) 0.0443(4) 0.3721(2) 0.1035(10) Uani 1 1 d U . . C33 C 0.8541(3) 0.1075(3) 0.3091(2) 0.0893(9) Uani 1 1 d . . . H1 H 0.4841 0.0965 0.0726 0.098 Uiso 1 1 calc R . . H2 H 0.5349 0.145 0.2436 0.09 Uiso 1 1 calc R . . H4 H 0.1441 0.0683 0.2454 0.091 Uiso 1 1 calc R . . H5 H 0.107 0.013 0.0748 0.102 Uiso 1 1 calc R . . H6 H 0.2896 0.1428 0.4059 0.09 Uiso 1 1 calc R . . H7 H 0.5577 0.1539 0.4077 0.088 Uiso 1 1 calc R . . H9 H 0.7032 0.2105 0.5676 0.094 Uiso 1 1 calc R A . H10 H 0.7456 0.2508 0.7396 0.101 Uiso 1 1 calc R . . H12 H 0.3523 0.1908 0.7388 0.1 Uiso 1 1 calc R . . H13 H 0.3105 0.1506 0.5664 0.095 Uiso 1 1 calc R A . H14 H 0.2472 0.4255 0.0096 0.127 Uiso 1 1 calc R . . H15 H 0.3217 0.4727 0.1768 0.12 Uiso 1 1 calc R . . H17 H -0.0383 0.3252 0.2039 0.109 Uiso 1 1 calc R . . H18 H -0.1023 0.2804 0.0329 0.113 Uiso 1 1 calc R . . H19 H 0.291 0.4872 0.3423 0.119 Uiso 1 1 calc R . . H20 H 0.0675 0.3653 0.366 0.115 Uiso 1 1 calc R . . H22 H 0.3836 0.55 0.506 0.105 Uiso 1 1 calc R B . H23 H 0.4561 0.5991 0.6781 0.103 Uiso 1 1 calc R . . H25 H 0.1151 0.4067 0.699 0.106 Uiso 1 1 calc R . . H26 H 0.0459 0.3596 0.5298 0.107 Uiso 1 1 calc R B . H27A H 0.2742 0.4965 0.8486 0.164 Uiso 0.83 1 calc PR B 1 H27B H 0.3455 0.6338 0.8503 0.164 Uiso 0.83 1 calc PR B 1 H27C H 0.425 0.5064 0.8337 0.164 Uiso 0.83 1 calc PR B 1 H27D H 0.5656 0.3418 0.9008 0.159 Uiso 0.52 1 calc PR A 2 H27E H 0.674 0.2383 0.8909 0.159 Uiso 0.52 1 calc PR A 2 H27F H 0.523 0.1912 0.8883 0.159 Uiso 0.52 1 calc PR A 2 H29 H 0.8501 -0.1262 0.1015 0.082 Uiso 1 1 calc R . . H31 H 1.0214 -0.1168 0.382 0.116 Uiso 1 1 calc R . . H32 H 0.9464 0.0871 0.441 0.124 Uiso 1 1 calc R . . H33 H 0.8248 0.1911 0.3345 0.107 Uiso 1 1 calc R . . H1O H 0.7441 0.0554 0.0854 0.131 Uiso 1 1 calc R . . H2O H 0.9703 -0.2905 0.1414 0.141 Uiso 1 1 calc R . . N1 N 0.2910(3) 0.0466(2) 0.05497(17) 0.0808(7) Uani 1 1 d . . . N2 N 0.0661(3) 0.3481(3) 0.00291(19) 0.0937(8) Uani 1 1 d . . . O1 O 0.7548(2) 0.1035(2) 0.14360(14) 0.0875(6) Uani 1 1 d . . . O2 O 0.9909(2) -0.2629(2) 0.20300(15) 0.0943(6) Uani 1 1 d . . . Cl1A Cl 0.5871(2) 0.25607(15) 0.88814(17) 0.1062(6) Uani 0.48 1 d PD A 1 Cl1B Cl 0.3518(8) 0.5473(5) 0.8384(6) 0.1092(10) Uani 0.17 1 d PD B 2 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 0.0829(19) 0.0893(19) 0.0660(17) 0.0125(14) 0.0141(15) 0.0047(15) C2 0.0679(16) 0.0808(18) 0.0656(16) 0.0074(13) 0.0023(13) 0.0043(13) C3 0.0740(16) 0.0584(14) 0.0610(13) 0.0155(11) 0.0060(13) 0.0084(12) C4 0.0704(16) 0.0846(18) 0.0703(17) 0.0207(14) 0.0078(14) 0.0004(13) C5 0.0682(17) 0.097(2) 0.080(2) 0.0186(16) -0.0066(15) 0.0048(14) C6 0.0784(18) 0.0756(17) 0.0665(13) 0.0170(13) 0.0079(15) 0.0072(13) C7 0.0780(17) 0.0705(16) 0.0684(12) 0.0161(12) 0.0094(14) 0.0066(13) C8 0.0828(16) 0.0568(14) 0.0663(12) 0.0169(11) 0.0058(12) 0.0083(12) C9 0.0809(18) 0.0794(18) 0.0705(17) 0.0188(14) 0.0043(14) 0.0062(14) C10 0.0863(19) 0.0793(18) 0.0762(19) 0.0212(14) -0.0119(16) 0.0018(14) C11 0.104(2) 0.0661(16) 0.0605(16) 0.0198(12) 0.0011(16) 0.0093(14) C12 0.092(2) 0.0852(19) 0.0721(18) 0.0211(14) 0.0173(16) 0.0074(15) C13 0.0723(16) 0.0881(19) 0.0730(18) 0.0219(14) 0.0004(12) 0.0061(14) C14 0.131(3) 0.102(2) 0.086(2) 0.0256(18) 0.029(2) 0.002(2) C15 0.111(2) 0.096(2) 0.084(2) 0.0157(17) 0.016(2) -0.0086(19) C16 0.110(2) 0.0692(17) 0.0761(15) 0.0148(14) 0.0141(17) 0.0218(16) C17 0.104(2) 0.096(2) 0.077(2) 0.0245(16) 0.0268(18) 0.0199(18) C18 0.095(2) 0.097(2) 0.083(2) 0.0144(17) 0.0104(18) 0.0160(17) C19 0.125(3) 0.096(2) 0.0767(15) 0.0215(17) 0.0202(18) 0.0193(19) C20 0.117(2) 0.090(2) 0.0812(15) 0.0234(16) 0.0214(18) 0.0214(18) C21 0.1063(18) 0.0732(17) 0.0762(14) 0.0209(14) 0.0251(14) 0.0223(13) C22 0.1055(19) 0.086(2) 0.083(2) 0.0314(15) 0.0343(15) 0.0148(14) C23 0.0857(19) 0.0819(19) 0.087(2) 0.0224(15) 0.0132(16) 0.0049(15) C24 0.097(2) 0.0760(18) 0.0705(17) 0.0219(14) 0.0160(16) 0.0216(15) C25 0.100(2) 0.091(2) 0.081(2) 0.0297(16) 0.0263(18) 0.0100(17) C26 0.094(2) 0.087(2) 0.082(2) 0.0218(16) 0.0106(17) 0.0042(16) C27A 0.134(2) 0.1239(19) 0.066(2) 0.0209(14) 0.0120(17) 0.0269(16) C27B 0.1541(13) 0.1009(10) 0.0576(11) 0.0240(7) -0.0011(8) 0.0099(9) C28 0.0628(15) 0.096(2) 0.0547(15) 0.0137(14) 0.0100(12) -0.0072(14) C29 0.0630(14) 0.0912(19) 0.0451(13) 0.0155(12) 0.0071(11) -0.0070(13) C30 0.0756(17) 0.095(2) 0.0536(15) 0.0245(14) 0.0071(13) -0.0089(15) C31 0.112(2) 0.125(2) 0.0517(16) 0.0340(16) 0.0032(15) -0.0093(18) C32 0.129(3) 0.126(2) 0.0450(15) 0.0140(17) 0.0108(17) -0.016(2) C33 0.091(2) 0.105(2) 0.0595(17) 0.0043(15) 0.0172(15) -0.0119(17) N1 0.0871(16) 0.0875(16) 0.0606(13) 0.0165(11) -0.0002(13) 0.0094(12) N2 0.122(2) 0.0871(18) 0.0695(16) 0.0184(13) 0.0132(16) 0.0233(16) O1 0.0852(13) 0.0980(14) 0.0690(12) 0.0124(10) 0.0019(11) 0.0149(11) O2 0.1079(15) 0.1114(17) 0.0691(12) 0.0393(12) 0.0073(12) 0.0131(13) Cl1A 0.1541(13) 0.1009(10) 0.0576(11) 0.0240(7) -0.0011(8) 0.0099(9) Cl1B 0.134(2) 0.1239(19) 0.066(2) 0.0209(14) 0.0120(17) 0.0269(16) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 1.372(4) . ? C1 H1 0.93 . ? C2 H2 0.93 . ? C3 C2 1.389(4) . ? C3 C4 1.377(4) . ? C3 C6 1.461(4) . ? C4 C5 1.365(4) . ? C4 H4 0.93 . ? C5 H5 0.93 . ? C6 H6 0.93 . ? C7 C6 1.286(4) . ? C7 H7 0.93 . ? C8 C13 1.376(4) . ? C8 C7 1.488(4) . ? C8 C9 1.378(4) . ? C9 C10 1.378(4) . ? C9 H9 0.93 . ? C10 H10 0.93 . ? C11 C10 1.368(4) . ? C11 C12 1.377(4) . ? C12 C13 1.381(4) . ? C12 H12 0.93 . ? C13 H13 0.93 . ? C14 H14 0.93 . ? C15 C14 1.356(5) . ? C15 H15 0.93 . ? C16 C15 1.368(4) . ? C16 C17 1.392(4) . ? C17 H17 0.93 . ? C18 C17 1.379(4) . ? C18 H18 0.93 . ? C19 C16 1.480(4) . ? C19 C20 1.235(4) . ? C19 H19 0.93 . ? C20 C21 1.493(4) . ? C20 H20 0.93 . ? C21 C22 1.391(4) . ? C21 C26 1.364(4) . ? C22 H22 0.93 . ? C23 C22 1.391(4) . ? C23 C24 1.392(4) . ? C23 H23 0.93 . ? C25 C24 1.374(4) . ? C25 C26 1.367(4) . ? C25 H25 0.93 . ? C26 H26 0.93 . ? C27A C24 1.505(7) . ? C27A H27A 0.96 . ? C27A H27B 0.96 . ? C27A H27C 0.96 . ? C27B C11 1.496(9) . ? C27B H27D 0.96 . ? C27B H27E 0.96 . ? C27B H27F 0.96 . ? C28 C29 1.379(4) . ? C28 O1 1.369(3) . ? C29 H29 0.93 . ? C30 C29 1.388(4) . ? C30 C31 1.378(4) . ? C30 O2 1.352(3) . ? C31 C32 1.360(5) . ? C31 H31 0.93 . ? C32 H32 0.93 . ? C33 C28 1.386(4) . ? C33 C32 1.384(5) . ? C33 H33 0.93 . ? N1 C1 1.331(4) . ? N1 C5 1.331(4) . ? N2 C14 1.325(5) . ? N2 C18 1.336(4) . ? O1 H1O 0.82 . ? O2 H2O 0.82 . ? Cl1A C11 1.746(4) . ? Cl1B C24 1.752(8) . ? 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 C1 C2 C3 120.0(3) . . ? C1 C2 H2 120 . . ? C1 N1 C5 115.5(2) . . ? C2 C1 H1 118 . . ? C2 C3 C6 125.0(2) . . ? C3 C2 H2 120 . . ? C3 C4 H4 119.9 . . ? C3 C6 H6 116.6 . . ? C4 C3 C2 115.8(2) . . ? C4 C3 C6 119.2(2) . . ? C4 C5 H5 117.8 . . ? C5 C4 C3 120.3(3) . . ? C5 C4 H4 119.9 . . ? C6 C7 C8 126.7(3) . . ? C6 C7 H7 116.6 . . ? C7 C6 C3 126.8(3) . . ? C7 C6 H6 116.6 . . ? C8 C13 C12 121.7(3) . . ? C8 C13 H13 119.1 . . ? C8 C7 H7 116.6 . . ? C8 C9 H9 119.4 . . ? C9 C10 H10 119.6 . . ? C9 C8 C7 118.6(3) . . ? C10 C11 C12 118.7(3) . . ? C10 C11 C27B 120.9(3) . . ? C10 C11 Cl1A 120.6(3) . . ? C10 C9 C8 121.2(3) . . ? C10 C9 H9 119.4 . . ? C11 C10 C9 120.9(3) . . ? C11 C10 H10 119.6 . . ? C11 C12 C13 120.0(3) . . ? C11 C12 H12 120 . . ? C11 C27B H27D 109.5 . . ? C11 C27B H27E 109.5 . . ? C11 C27B H27F 109.5 . . ? C12 C11 C27B 120.4(3) . . ? C12 C11 Cl1A 120.6(3) . . ? C12 C13 H13 119.1 . . ? C13 C12 H12 120 . . ? C13 C8 C7 123.9(3) . . ? C13 C8 C9 117.4(2) . . ? C14 C15 C16 120.1(3) . . ? C14 C15 H15 120 . . ? C14 N2 C18 115.6(3) . . ? C15 C14 H14 117.5 . . ? C15 C16 C17 116.5(3) . . ? C15 C16 C19 117.9(3) . . ? C16 C15 H15 120 . . ? C16 C17 H17 120.2 . . ? C16 C19 H19 116.2 . . ? C17 C16 C19 125.6(3) . . ? C17 C18 H18 118.3 . . ? C18 C17 C16 119.5(3) . . ? C18 C17 H17 120.2 . . ? C19 C20 C21 128.2(4) . . ? C19 C20 H20 115.9 . . ? C20 C19 C16 127.6(4) . . ? C20 C19 H19 116.2 . . ? C21 C20 H20 115.9 . . ? C21 C22 H22 119.1 . . ? C21 C26 C25 122.2(3) . . ? C21 C26 H26 118.9 . . ? C22 C21 C20 124.5(3) . . ? C22 C23 C24 119.8(3) . . ? C22 C23 H23 120.1 . . ? C23 C22 C21 121.8(3) . . ? C23 C22 H22 119.1 . . ? C23 C24 C27A 120.5(3) . . ? C23 C24 Cl1B 118.3(4) . . ? C24 C23 H23 120.1 . . ? C24 C25 H25 119.1 . . ? C24 C27A H27A 109.5 . . ? C24 C27A H27B 109.5 . . ? C24 C27A H27C 109.5 . . ? C25 C24 C23 117.6(3) . . ? C25 C24 C27A 121.8(3) . . ? C25 C24 Cl1B 124.1(4) . . ? C25 C26 H26 118.9 . . ? C26 C21 C20 118.7(3) . . ? C26 C21 C22 116.8(3) . . ? C26 C25 C24 121.7(3) . . ? C26 C25 H25 119.1 . . ? C28 C29 C30 120.3(2) . . ? C28 C29 H29 119.8 . . ? C28 C33 H33 121.2 . . ? C28 O1 H1O 109.5 . . ? C29 C28 C33 120.5(3) . . ? C30 C29 H29 119.8 . . ? C30 C31 H31 120.4 . . ? C30 O2 H2O 109.5 . . ? C31 C30 C29 119.5(3) . . ? C31 C32 C33 122.7(3) . . ? C31 C32 H32 118.6 . . ? C32 C31 C30 119.3(3) . . ? C32 C31 H31 120.4 . . ? C32 C33 C28 117.6(3) . . ? C32 C33 H33 121.2 . . ? C33 C32 H32 118.6 . . ? H27D C27B H27E 109.5 . . ? H27D C27B H27F 109.5 . . ? H27E C27B H27F 109.5 . . ? N1 C1 C2 123.9(3) . . ? N1 C1 H1 118 . . ? N1 C5 C4 124.4(3) . . ? N1 C5 H5 117.8 . . ? N2 C14 C15 124.9(3) . . ? N2 C14 H14 117.5 . . ? N2 C18 C17 123.4(3) . . ? N2 C18 H18 118.3 . . ? O1 C28 C29 121.4(2) . . ? O1 C28 C33 118.2(3) . . ? O2 C30 C29 122.3(2) . . ? O2 C30 C31 118.1(3) . . ? #------------------ SECTION 2. COMPOUND(S) DETAILS -------------------------# data_1-150K _database_code_depnum_ccdc_archive 'CCDC 809485' #TrackingRef '1-150K.cif' _audit_creation_date 2011-09-25T23:53:28-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_formula_sum 'C33.34 H30.03 Cl0.66 N2 O2' _chemical_formula_moiety ; C13.52 H11.55 Cl0.49 N, C13.83 H12.48 Cl0.17 N, C6 H6 O2 ; _chemical_formula_weight 514.05 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _cell_length_a 9.9438(11) _cell_length_b 10.1775(11) _cell_length_c 14.0261(15) _cell_angle_alpha 105.642(5) _cell_angle_beta 98.420(5) _cell_angle_gamma 92.492(5) _cell_volume 1347.0(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 25.35 _cell_measurement_reflns_used 4760 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.08 _exptl_crystal_density_diffrn 1.267 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 542.4 #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.142 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'HKL Scalepack (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.9457 _exptl_absorpt_correction_T_max 0.9888 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_reflns_av_R_equivalents 0.02 _diffrn_reflns_av_unetI/netI 0.0331 _diffrn_reflns_number 8856 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 5.18 _diffrn_reflns_theta_max 24.99 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.987 _diffrn_measured_fraction_theta_max 0.987 _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD phi and omega scans' _diffrn_detector_area_resol_mean 9 _reflns_number_total 4679 _reflns_number_gt 3725 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL Denzo, Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL (Sheldrick, 2008)' _computing_molecular_graphics 'Rastop (Valadon, 2004)' _computing_publication_material 'WinGX (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # 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^ > 2\s(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. A total of 26 geometrical restraints (i.e. DELU, SADI, DFIX, FLAT) and constraints (i.e. EADP) were utilized to model the 4-chlorophenyl and 4-methylphenyl groups. ; _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^)+(0.0561P)^2^+0.3000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 4679 _refine_ls_number_parameters 355 _refine_ls_number_restraints 26 _refine_ls_R_factor_all 0.0585 _refine_ls_R_factor_gt 0.0434 _refine_ls_wR_factor_ref 0.1148 _refine_ls_wR_factor_gt 0.1079 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.073 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.38 _refine_diff_density_min -0.248 _refine_diff_density_rms 0.035 #----------------------------------------------------------------------------# # 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' O O 0.0106 0.006 '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 0.41709(17) 0.09144(16) 0.10610(12) 0.0338(4) Uani 1 1 d . . . C2 C 0.44703(16) 0.12250(16) 0.20905(11) 0.0311(4) Uani 1 1 d . . . C3 C 0.34322(15) 0.11086(15) 0.26411(11) 0.0277(3) Uani 1 1 d . . . C4 C 0.21258(16) 0.06931(16) 0.20902(12) 0.0321(4) Uani 1 1 d . . . C5 C 0.19268(17) 0.03725(17) 0.10617(12) 0.0353(4) Uani 1 1 d . . . C6 C 0.36425(16) 0.13675(16) 0.37312(11) 0.0298(4) Uani 1 1 d . . . C7 C 0.48324(16) 0.15649(15) 0.43412(11) 0.0293(4) Uani 1 1 d . . . C8 C 0.50467(16) 0.17539(10) 0.54296(11) 0.0282(3) Uani 1 1 d D A . C9 C 0.63587(16) 0.20648(11) 0.59784(12) 0.0329(4) Uani 1 1 d D . . C10 C 0.66053(17) 0.22990(10) 0.70116(12) 0.0358(4) Uani 1 1 d D A . C11 C 0.55248(18) 0.22230(8) 0.75190(11) 0.0335(4) Uani 1 1 d D . . C12 C 0.42075(17) 0.19149(11) 0.69906(12) 0.0354(4) Uani 1 1 d D A . C13 C 0.39711(16) 0.16842(12) 0.59590(12) 0.0325(4) Uani 1 1 d D . . C14 C 0.1846(2) 0.40588(19) 0.04535(13) 0.0450(5) Uani 1 1 d . . . C15 C 0.23437(19) 0.43586(18) 0.14617(13) 0.0421(4) Uani 1 1 d . . . C16 C 0.15232(18) 0.40666(16) 0.21121(12) 0.0354(4) Uani 1 1 d U . . C17 C 0.02042(18) 0.34741(17) 0.16801(13) 0.0375(4) Uani 1 1 d . . . C18 C -0.02104(19) 0.32150(17) 0.06590(13) 0.0399(4) Uani 1 1 d . . . C19 C 0.20688(18) 0.44031(17) 0.31824(12) 0.0368(4) Uani 1 1 d U . . C20 C 0.14693(17) 0.40830(17) 0.38830(13) 0.0362(4) Uani 1 1 d U . . C21 C 0.20007(16) 0.44323(12) 0.49610(12) 0.0335(4) Uani 1 1 d DU B . C22 C 0.32638(17) 0.51545(13) 0.53958(12) 0.0363(4) Uani 1 1 d DU . . C23 C 0.37173(17) 0.54638(13) 0.64207(12) 0.0365(4) Uani 1 1 d D B . C24 C 0.29206(16) 0.50606(11) 0.70480(12) 0.0351(4) Uani 1 1 d DU . . C25 C 0.16636(17) 0.43422(13) 0.66200(13) 0.0376(4) Uani 1 1 d D B . C26 C 0.12168(17) 0.40356(14) 0.55974(13) 0.0373(4) Uani 1 1 d D . . C27A C 0.3421(3) 0.54001(19) 0.8168(3) 0.0454(6) Uani 0.827(3) 1 d PDU B 1 C27B C 0.5777(3) 0.24761(16) 0.8636(5) 0.0422(4) Uani 0.515(3) 1 d PD A 2 C28 C 0.82428(15) 0.04223(17) 0.20617(11) 0.0306(4) Uani 1 1 d . . . C29 C 0.87008(15) -0.08545(16) 0.16877(11) 0.0292(4) Uani 1 1 d . . . C30 C 0.94480(16) -0.14861(17) 0.23313(11) 0.0316(4) Uani 1 1 d . . . C31 C 0.97147(18) -0.08402(19) 0.33574(12) 0.0400(4) Uani 1 1 d . . . C32 C 0.92404(19) 0.04247(19) 0.37161(12) 0.0430(5) Uani 1 1 d . . . C33 C 0.85065(17) 0.10769(18) 0.30856(12) 0.0373(4) Uani 1 1 d . . . H1 H 0.4891 0.1027 0.0705 0.041 Uiso 1 1 calc R . . H2 H 0.5379 0.1517 0.2425 0.037 Uiso 1 1 calc R . . H4 H 0.1373 0.0632 0.2427 0.038 Uiso 1 1 calc R . . H5 H 0.1029 0.0069 0.0707 0.042 Uiso 1 1 calc R . . H6 H 0.2846 0.1398 0.4034 0.036 Uiso 1 1 calc R . . H7 H 0.5628 0.1586 0.4042 0.035 Uiso 1 1 calc R . . H9 H 0.7107 0.2118 0.5636 0.039 Uiso 1 1 calc R A . H10 H 0.7511 0.2511 0.7369 0.043 Uiso 1 1 calc R . . H12 H 0.3464 0.1862 0.7337 0.043 Uiso 1 1 calc R . . H13 H 0.3063 0.1475 0.5605 0.039 Uiso 1 1 calc R A . H14 H 0.2434 0.4266 0.0028 0.054 Uiso 1 1 calc R . . H15 H 0.3249 0.4766 0.1714 0.051 Uiso 1 1 calc R . . H17 H -0.0404 0.3251 0.2087 0.045 Uiso 1 1 calc R . . H18 H -0.1113 0.2816 0.0382 0.048 Uiso 1 1 calc R . . H19 H 0.2941 0.4901 0.3397 0.044 Uiso 1 1 calc R . . H1O H 0.7418 0.0563 0.0849 0.056 Uiso 1 1 calc R . . H20 H 0.0604 0.3573 0.3664 0.043 Uiso 1 1 calc R . . H22 H 0.3824 0.544 0.4982 0.044 Uiso 1 1 calc R B . H23 H 0.4582 0.5957 0.6699 0.044 Uiso 1 1 calc R . . H25 H 0.1103 0.4057 0.7034 0.045 Uiso 1 1 calc R . . H26 H 0.0352 0.3541 0.5322 0.045 Uiso 1 1 calc R B . H27A H 0.2747 0.5014 0.8485 0.068 Uiso 0.827(3) 1 calc PR B 1 H27B H 0.3547 0.6397 0.8455 0.068 Uiso 0.827(3) 1 calc PR B 1 H27C H 0.4292 0.5009 0.8288 0.068 Uiso 0.827(3) 1 calc PR B 1 H27D H 0.5701 0.3446 0.896 0.063 Uiso 0.515(3) 1 calc PR A 2 H27E H 0.6694 0.2236 0.885 0.063 Uiso 0.515(3) 1 calc PR A 2 H27F H 0.5099 0.1912 0.8829 0.063 Uiso 0.515(3) 1 calc PR A 2 H29 H 0.8503 -0.13 0.0988 0.035 Uiso 1 1 calc R . . H2O H 0.98 -0.2963 0.1365 0.058 Uiso 1 1 calc R . . H31 H 1.0217 -0.1264 0.3805 0.048 Uiso 1 1 calc R . . H32 H 0.9422 0.0863 0.4417 0.052 Uiso 1 1 calc R . . H33 H 0.8192 0.1949 0.3347 0.045 Uiso 1 1 calc R . . N1 N 0.29228(14) 0.04615(14) 0.05288(10) 0.0349(3) Uani 1 1 d . . . N2 N 0.05894(16) 0.34950(15) 0.00360(10) 0.0412(4) Uani 1 1 d . . . O1 O 0.75326(12) 0.10669(12) 0.14426(8) 0.0374(3) Uani 1 1 d . . . O2 O 0.99523(12) -0.27140(12) 0.19950(8) 0.0389(3) Uani 1 1 d . . . Cl1A Cl 0.58205(12) 0.25217(8) 0.88254(11) 0.0422(4) Uani 0.485(3) 1 d PD A 1 Cl1B Cl 0.3543(4) 0.5477(3) 0.8343(3) 0.0454(6) Uani 0.173(3) 1 d PDU B 2 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 0.0334(9) 0.0361(9) 0.0306(9) 0.0074(7) 0.0053(7) 0.0017(7) C2 0.0279(8) 0.0328(9) 0.0292(9) 0.0052(7) 0.0008(7) 0.0010(7) C3 0.0309(8) 0.0226(8) 0.0285(8) 0.0064(6) 0.0020(7) 0.0038(6) C4 0.0286(8) 0.0340(9) 0.0330(9) 0.0093(7) 0.0032(7) 0.0022(7) C5 0.0307(9) 0.0387(9) 0.0329(9) 0.0089(7) -0.0034(7) 0.0014(7) C6 0.0301(9) 0.0310(8) 0.0276(8) 0.0069(7) 0.0048(7) 0.0031(7) C7 0.0309(9) 0.0276(8) 0.0298(8) 0.0084(7) 0.0061(7) 0.0025(7) C8 0.0324(8) 0.0234(8) 0.0277(8) 0.0066(6) 0.0022(7) 0.0023(6) C9 0.0323(9) 0.0331(9) 0.0331(9) 0.0095(7) 0.0048(7) 0.0021(7) C10 0.0371(9) 0.0324(9) 0.0338(9) 0.0080(7) -0.0042(7) 0.0002(7) C11 0.0465(10) 0.0255(8) 0.0270(8) 0.0069(7) 0.0010(7) 0.0055(7) C12 0.0412(10) 0.0337(9) 0.0328(9) 0.0095(7) 0.0096(8) 0.0053(7) C13 0.0305(9) 0.0340(9) 0.0320(9) 0.0095(7) 0.0019(7) 0.0033(7) C14 0.0563(12) 0.0434(10) 0.0366(10) 0.0100(8) 0.0143(9) 0.0020(9) C15 0.0444(10) 0.0394(10) 0.0392(10) 0.0064(8) 0.0067(8) -0.0023(8) C16 0.0452(10) 0.0272(8) 0.0330(8) 0.0063(7) 0.0072(7) 0.0074(7) C17 0.0417(10) 0.0355(9) 0.0358(10) 0.0087(7) 0.0098(8) 0.0058(8) C18 0.0418(10) 0.0366(9) 0.0382(10) 0.0061(8) 0.0036(8) 0.0085(8) C19 0.0381(9) 0.0334(9) 0.0369(9) 0.0069(7) 0.0061(7) 0.0010(7) C20 0.0367(9) 0.0315(9) 0.0386(8) 0.0077(7) 0.0044(7) 0.0024(7) C21 0.0395(9) 0.0268(8) 0.0349(8) 0.0082(7) 0.0079(7) 0.0069(7) C22 0.0413(9) 0.0339(9) 0.0372(10) 0.0126(7) 0.0126(7) 0.0048(7) C23 0.0371(9) 0.0331(9) 0.0386(10) 0.0088(7) 0.0060(8) 0.0036(7) C24 0.0439(10) 0.0298(9) 0.0332(8) 0.0089(7) 0.0087(7) 0.0107(7) C25 0.0431(10) 0.0356(9) 0.0386(10) 0.0140(8) 0.0134(8) 0.0068(8) C26 0.0374(9) 0.0324(9) 0.0416(10) 0.0091(7) 0.0076(8) 0.0015(7) C27A 0.0574(10) 0.0456(9) 0.0325(10) 0.0084(6) 0.0092(7) 0.0084(6) C27B 0.0623(6) 0.0405(5) 0.0228(8) 0.0104(3) 0.0011(4) 0.0041(4) C28 0.0242(8) 0.0396(9) 0.0273(8) 0.0089(7) 0.0047(6) -0.0038(7) C29 0.0259(8) 0.0380(9) 0.0219(8) 0.0068(7) 0.0026(6) -0.0037(7) C30 0.0292(8) 0.0386(9) 0.0271(8) 0.0104(7) 0.0048(7) -0.0037(7) C31 0.0455(10) 0.0492(11) 0.0259(9) 0.0147(8) 0.0017(7) -0.0029(8) C32 0.0514(11) 0.0531(11) 0.0200(8) 0.0056(8) 0.0041(8) -0.0074(9) C33 0.0388(9) 0.0398(9) 0.0291(9) 0.0018(7) 0.0092(7) -0.0036(8) N1 0.0378(8) 0.0364(8) 0.0286(7) 0.0088(6) -0.0003(6) 0.0044(6) N2 0.0527(9) 0.0368(8) 0.0334(8) 0.0080(6) 0.0062(7) 0.0105(7) O1 0.0376(7) 0.0407(7) 0.0299(6) 0.0054(5) 0.0013(5) 0.0058(5) O2 0.0440(7) 0.0441(7) 0.0298(6) 0.0136(5) 0.0030(5) 0.0057(6) Cl1A 0.0623(6) 0.0405(5) 0.0228(8) 0.0104(3) 0.0011(4) 0.0041(4) Cl1B 0.0574(10) 0.0456(9) 0.0325(10) 0.0084(6) 0.0092(7) 0.0084(6) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 1.376(2) . ? C1 H1 0.95 . ? C2 H2 0.95 . ? C3 C2 1.396(2) . ? C3 C4 1.395(2) . ? C3 C6 1.461(2) . ? C4 C5 1.372(2) . ? C4 H4 0.95 . ? C5 H5 0.95 . ? C6 H6 0.95 . ? C7 C6 1.328(2) . ? C7 H7 0.95 . ? C8 C13 1.398(2) . ? C8 C7 1.468(2) . ? C8 C9 1.390(2) . ? C9 C10 1.386(2) . ? C9 H9 0.95 . ? C10 H10 0.95 . ? C11 C10 1.383(2) . ? C11 C12 1.385(2) . ? C12 C13 1.384(2) . ? C12 H12 0.95 . ? C13 H13 0.95 . ? C14 H14 0.95 . ? C15 C14 1.374(3) . ? C15 H15 0.95 . ? C16 C15 1.389(2) . ? C16 C17 1.397(2) . ? C17 H17 0.95 . ? C18 C17 1.380(2) . ? C18 H18 0.95 . ? C19 C16 1.461(2) . ? C19 C20 1.325(2) . ? C19 H19 0.95 . ? C20 C21 1.467(2) . ? C20 H20 0.95 . ? C21 C22 1.394(2) . ? C21 C26 1.392(2) . ? C22 H22 0.95 . ? C23 C22 1.387(2) . ? C23 H23 0.95 . ? C24 C23 1.393(2) . ? C24 C25 1.386(2) . ? C25 C26 1.383(2) . ? C25 H25 0.95 . ? C26 H26 0.95 . ? C27A C24 1.516(4) . ? C27A H27A 0.98 . ? C27A H27B 0.98 . ? C27A H27C 0.98 . ? C27B C11 1.499(7) . ? C27B H27D 0.98 . ? C27B H27E 0.98 . ? C27B H27F 0.98 . ? C28 C29 1.388(2) . ? C28 O1 1.360(2) . ? C29 H29 0.95 . ? C30 C29 1.392(2) . ? C30 C31 1.392(2) . ? C30 O2 1.3571(19) . ? C31 C32 1.381(3) . ? C31 H31 0.95 . ? C32 H32 0.95 . ? C33 C28 1.391(2) . ? C33 C32 1.387(3) . ? C33 H33 0.95 . ? N1 C1 1.343(2) . ? N1 C5 1.339(2) . ? N2 C14 1.333(2) . ? N2 C18 1.340(2) . ? O1 H1O 0.84 . ? O2 H2O 0.84 . ? Cl1A C11 1.752(2) . ? Cl1B C24 1.759(5) . ? 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 C1 C2 C3 119.68(15) . . ? C1 C2 H2 120.2 . . ? C2 C1 H1 118 . . ? C2 C3 C6 124.26(14) . . ? C3 C2 H2 120.2 . . ? C3 C4 H4 120 . . ? C3 C6 H6 116.7 . . ? C4 C3 C2 116.28(14) . . ? C4 C3 C6 119.45(14) . . ? C4 C5 H5 118.1 . . ? C5 C4 C3 120.04(15) . . ? C5 C4 H4 120 . . ? C5 N1 C1 116.08(14) . . ? C6 C7 C8 126.77(14) . . ? C6 C7 H7 116.6 . . ? C7 C6 C3 126.66(14) . . ? C7 C6 H6 116.7 . . ? C8 C13 H13 119.5 . . ? C8 C7 H7 116.6 . . ? C8 C9 H9 119.1 . . ? C9 C10 H10 120.2 . . ? C9 C8 C13 117.49(14) . . ? C9 C8 C7 119.80(14) . . ? C10 C11 C12 119.72(15) . . ? C10 C11 C27B 120.20(15) . . ? C10 C11 Cl1A 120.15(14) . . ? C10 C9 C8 121.83(15) . . ? C10 C9 H9 119.1 . . ? C11 C10 C9 119.64(15) . . ? C11 C10 H10 120.2 . . ? C11 C12 H12 119.9 . . ? C11 C27B H27D 109.5 . . ? C11 C27B H27E 109.5 . . ? C11 C27B H27F 109.5 . . ? C12 C11 C27B 120.08(15) . . ? C12 C11 Cl1A 120.13(14) . . ? C12 C13 C8 121.10(15) . . ? C12 C13 H13 119.5 . . ? C13 C12 C11 120.22(15) . . ? C13 C12 H12 119.9 . . ? C13 C8 C7 122.67(14) . . ? C14 C15 C16 120.01(17) . . ? C14 C15 H15 120 . . ? C14 N2 C18 116.34(15) . . ? C15 C14 H14 118 . . ? C15 C16 C17 116.33(15) . . ? C15 C16 C19 119.12(16) . . ? C16 C15 H15 120 . . ? C16 C17 H17 120.2 . . ? C16 C19 H19 116.7 . . ? C17 C16 C19 124.55(15) . . ? C17 C18 H18 118.2 . . ? C18 C17 C16 119.65(16) . . ? C18 C17 H17 120.2 . . ? C19 C20 C21 126.89(16) . . ? C19 C20 H20 116.6 . . ? C20 C19 C16 126.51(16) . . ? C20 C19 H19 116.7 . . ? C21 C20 H20 116.6 . . ? C21 C22 H22 119.4 . . ? C21 C26 H26 119.1 . . ? C22 C21 C20 123.46(15) . . ? C22 C23 C24 120.84(16) . . ? C22 C23 H23 119.6 . . ? C23 C22 C21 121.21(15) . . ? C23 C22 H22 119.4 . . ? C23 C24 C27A 120.66(16) . . ? C23 C24 Cl1B 119.1(2) . . ? C24 C23 H23 119.6 . . ? C24 C25 H25 119.6 . . ? C24 C27A H27A 109.5 . . ? C24 C27A H27B 109.5 . . ? C24 C27A H27C 109.5 . . ? C25 C24 C23 118.22(15) . . ? C25 C24 C27A 121.12(15) . . ? C25 C24 Cl1B 122.7(2) . . ? C25 C26 C21 121.75(16) . . ? C25 C26 H26 119.1 . . ? C26 C21 C20 119.26(15) . . ? C26 C21 C22 117.28(15) . . ? C26 C25 C24 120.70(15) . . ? C26 C25 H25 119.6 . . ? C28 C29 C30 120.39(14) . . ? C28 C29 H29 119.8 . . ? C28 C33 H33 120.8 . . ? C28 O1 H1O 109.5 . . ? C29 C28 C33 120.40(15) . . ? C30 C29 H29 119.8 . . ? C30 C31 H31 120.4 . . ? C30 O2 H2O 109.5 . . ? C31 C30 C29 119.62(16) . . ? C31 C32 C33 122.10(16) . . ? C31 C32 H32 118.9 . . ? C32 C31 C30 119.12(16) . . ? C32 C31 H31 120.4 . . ? C32 C33 C28 118.36(16) . . ? C32 C33 H33 120.8 . . ? C33 C32 H32 118.9 . . ? H27D C27B H27E 109.5 . . ? H27D C27B H27F 109.5 . . ? H27E C27B H27F 109.5 . . ? N1 C1 C2 123.95(15) . . ? N1 C1 H1 118 . . ? N1 C5 C4 123.88(15) . . ? N1 C5 H5 118.1 . . ? N2 C14 C15 124.01(17) . . ? N2 C14 H14 118 . . ? N2 C18 C17 123.65(17) . . ? N2 C18 H18 118.2 . . ? O1 C28 C29 121.25(14) . . ? O1 C28 C33 118.36(15) . . ? O2 C30 C29 122.39(14) . . ? O2 C30 C31 117.98(15) . . ? #------------------ SECTION 2. COMPOUND(S) DETAILS -------------------------# data_3 _database_code_depnum_ccdc_archive 'CCDC 809486' #TrackingRef '3.cif' _audit_creation_date 2011-09-30T11:44:51-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_formula_sum 'C26.93 H26.05 Br2 Cl1.07 N2 O0.63' _chemical_formula_moiety ; C26.93 H24.79 Cl1.07 N2, 0.63(H2 O), 2(Br) ; _chemical_formula_weight 585.54 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _cell_length_a 18.3233(19) _cell_length_b 9.8023(11) _cell_length_c 14.3984(15) _cell_angle_alpha 90 _cell_angle_beta 93.253(5) _cell_angle_gamma 90 _cell_volume 2581.9(5) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.88 _cell_measurement_reflns_used 10729 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.506 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1179.5 #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 3.271 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'HKL Scalepack (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.4410 _exptl_absorpt_correction_T_max 0.8538 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_reflns_av_R_equivalents 0.0385 _diffrn_reflns_av_unetI/netI 0.0434 _diffrn_reflns_number 11967 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 5.85 _diffrn_reflns_theta_max 25 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 0.986 _diffrn_measured_fraction_theta_max 0.986 _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD phi and omega scans' _diffrn_detector_area_resol_mean 9 _reflns_number_total 4489 _reflns_number_gt 3339 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL Denzo, Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL (Sheldrick, 2008)' _computing_molecular_graphics 'Rastop (Valadon, 2004)' _computing_publication_material 'WinGX (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # 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^ > 2\s(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. A total of 31 geometrical restraints (i.e. SADI, DFIX, FLAT) and constraints (i.e. EADP) were utilized to model the 4-chlorophenyl and 4-methylphenyl groups. The positions of two C-H H-atoms were refined. Calculated "riding" positions are not sufficient for these two H-atoms since calculated positions result in unreasonable short H-H distances owing to the highly strained molecular structure of the cyclobutane derivative. ; _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^)+(0.0401P)^2^+3.1919P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 4489 _refine_ls_number_parameters 326 _refine_ls_number_restraints 31 _refine_ls_R_factor_all 0.0733 _refine_ls_R_factor_gt 0.0484 _refine_ls_wR_factor_ref 0.1096 _refine_ls_wR_factor_gt 0.1023 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.03 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.532 _refine_diff_density_min -0.493 _refine_diff_density_rms 0.058 #----------------------------------------------------------------------------# # 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 '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 0.0173(2) 0.0481(5) 0.6225(3) 0.0582(11) Uani 1 1 d . . . C2 C 0.0906(2) 0.0837(5) 0.6288(3) 0.0578(11) Uani 1 1 d . . . C3 C 0.1108(2) 0.2156(4) 0.6588(3) 0.0462(10) Uani 1 1 d . . . C4 C 0.0552(2) 0.3042(4) 0.6799(3) 0.0524(10) Uani 1 1 d . . . C5 C -0.0155(2) 0.2637(5) 0.6717(3) 0.0585(11) Uani 1 1 d . . . C6 C 0.1891(2) 0.2613(4) 0.6726(3) 0.0486(10) Uani 1 1 d D . . C7 C 0.2398(2) 0.1777(4) 0.7436(3) 0.0463(9) Uani 1 1 d . . . C8 C 0.2761(2) 0.1073(4) 0.6623(3) 0.0478(10) Uani 1 1 d . . . C9 C 0.2402(2) 0.2183(4) 0.5952(3) 0.0460(9) Uani 1 1 d . . . C10 C 0.29289(18) 0.3256(4) 0.5631(2) 0.0465(9) Uani 1 1 d D . . C11 C 0.33253(19) 0.2932(5) 0.4877(3) 0.0551(11) Uani 1 1 d D . . C12 C 0.37888(19) 0.3879(5) 0.4507(3) 0.0622(12) Uani 1 1 d D B . C13 C 0.38638(18) 0.5147(5) 0.4891(3) 0.0646(13) Uani 1 1 d D . . C14 C 0.3477(2) 0.5498(5) 0.5645(3) 0.0672(13) Uani 1 1 d D B . C15 C 0.3004(2) 0.4537(5) 0.6024(3) 0.0591(11) Uani 1 1 d D . . C16A C 0.4363(5) 0.6188(15) 0.4493(10) 0.0934(16) Uani 0.553(9) 1 d PD B 1 C16B C 0.5912(6) 0.0241(18) 0.6561(8) 0.0756(10) Uani 0.377(9) 1 d PD A 2 C17 C 0.2080(2) 0.0917(4) 0.8180(3) 0.0500(10) Uani 1 1 d . . . C18 C 0.1534(2) 0.1407(5) 0.8698(3) 0.0561(11) Uani 1 1 d . . . C19 C 0.1264(3) 0.0623(6) 0.9378(3) 0.0660(13) Uani 1 1 d . . . C20 C 0.2068(3) -0.1132(5) 0.9079(4) 0.0733(14) Uani 1 1 d . . . C21 C 0.2345(3) -0.0372(5) 0.8372(3) 0.0646(12) Uani 1 1 d . . . C22 C 0.3581(2) 0.0840(4) 0.6653(2) 0.0483(10) Uani 1 1 d D A . C23 C 0.3865(3) -0.0262(4) 0.6201(2) 0.0625(12) Uani 1 1 d D . . C24 C 0.4611(3) -0.0455(5) 0.6171(3) 0.0694(13) Uani 1 1 d D A . C25 C 0.5099(2) 0.0455(4) 0.6596(2) 0.0574(11) Uani 1 1 d D . . C26 C 0.4827(2) 0.1564(4) 0.7053(2) 0.0558(11) Uani 1 1 d D A . C27 C 0.4065(2) 0.1740(4) 0.7074(2) 0.0525(10) Uani 1 1 d D . . H1 H 0.0029 -0.041 0.6032 0.07 Uiso 1 1 calc R . . H2 H 0.1268 0.0197 0.6131 0.069 Uiso 1 1 calc R . . H4 H 0.0668 0.3942 0.7003 0.063 Uiso 1 1 calc R . . H5 H -0.0531 0.3255 0.6863 0.07 Uiso 1 1 calc R . . H6 H 0.190(3) 0.3583(14) 0.689(3) 0.098 Uiso 1 1 d D . . H7 H 0.2761 0.2419 0.7743 0.056 Uiso 1 1 calc R . . H8 H 0.251 0.0181 0.6494 0.057 Uiso 1 1 calc R . . H9 H 0.212 0.1754 0.5413 0.055 Uiso 1 1 calc R . . H11 H 0.328 0.2049 0.4608 0.066 Uiso 1 1 calc R . . H12 H 0.4056 0.3644 0.3984 0.075 Uiso 1 1 calc R . . H14 H 0.3528 0.6383 0.591 0.081 Uiso 1 1 calc R . . H15 H 0.277(3) 0.485(5) 0.654(2) 0.098 Uiso 1 1 d D . . H16A H 0.4451 0.5948 0.3848 0.14 Uiso 0.553(9) 1 calc PR B 1 H16B H 0.4829 0.6204 0.4862 0.14 Uiso 0.553(9) 1 calc PR B 1 H16C H 0.4135 0.7091 0.4509 0.14 Uiso 0.553(9) 1 calc PR B 1 H16D H 0.614 0.1079 0.6345 0.113 Uiso 0.377(9) 1 calc PR A 2 H16E H 0.6006 -0.0507 0.6132 0.113 Uiso 0.377(9) 1 calc PR A 2 H16F H 0.6119 0.0011 0.7184 0.113 Uiso 0.377(9) 1 calc PR A 2 H18 H 0.1343 0.2296 0.8583 0.067 Uiso 1 1 calc R . . H19 H 0.0878 0.0962 0.9727 0.079 Uiso 1 1 calc R . . H1N H -0.0840(5) 0.127(6) 0.641(4) 0.123 Uiso 1 1 d D . . H20 H 0.2256 -0.2016 0.9223 0.088 Uiso 1 1 calc R . . H21 H 0.272 -0.074 0.8017 0.077 Uiso 1 1 calc R . . H23 H 0.3542 -0.0904 0.5904 0.075 Uiso 1 1 calc R A . H24 H 0.4791 -0.1224 0.5854 0.083 Uiso 1 1 calc R . . H26 H 0.5151 0.2203 0.7352 0.067 Uiso 1 1 calc R . . H27 H 0.3882 0.2508 0.739 0.063 Uiso 1 1 calc R . . H2N H 0.1304 -0.105(5) 1.005(2) 0.123 Uiso 1 1 d D . . H111 H 0.177(3) 0.770(8) 0.703(6) 0.123 Uiso 0.631(15) 1 d PD . . H222 H 0.233(3) 0.667(7) 0.726(6) 0.123 Uiso 0.631(15) 1 d PD . . N1 N -0.03256(19) 0.1391(4) 0.6436(2) 0.0541(9) Uani 1 1 d D . . N2 N 0.1530(2) -0.0601(5) 0.9558(3) 0.0717(12) Uani 1 1 d D . . Cl1A Cl 0.60452(13) 0.0217(3) 0.65578(17) 0.0756(10) Uani 0.623(9) 1 d PD A 1 Cl1B Cl 0.44311(19) 0.6370(5) 0.4448(4) 0.0934(16) Uani 0.447(9) 1 d PD B 2 Br1 Br 0.19285(2) 0.51508(5) 0.87740(3) 0.06494(18) Uani 1 1 d . . . Br2 Br 0.94693(3) 0.19206(6) 0.89810(3) 0.0819(2) Uani 1 1 d . . . O1 O 0.2210(5) 0.7369(7) 0.6874(5) 0.114(4) Uani 0.631(15) 1 d PD . . 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 0.057(3) 0.052(3) 0.066(3) 0.002(2) 0.004(2) -0.012(2) C2 0.050(3) 0.054(3) 0.071(3) -0.004(2) 0.009(2) -0.003(2) C3 0.045(2) 0.050(3) 0.044(2) 0.0100(18) 0.0065(17) -0.0111(19) C4 0.061(3) 0.053(3) 0.044(2) 0.0075(19) 0.0055(18) 0.005(2) C5 0.055(3) 0.069(3) 0.051(2) 0.009(2) 0.0051(19) 0.009(2) C6 0.052(2) 0.040(2) 0.055(2) 0.0001(18) 0.0120(18) -0.0038(19) C7 0.050(2) 0.047(2) 0.043(2) -0.0011(17) 0.0078(17) -0.0087(19) C8 0.056(2) 0.038(2) 0.051(2) -0.0014(17) 0.0096(18) -0.0058(19) C9 0.047(2) 0.044(2) 0.048(2) -0.0004(17) 0.0055(17) -0.0072(18) C10 0.047(2) 0.045(3) 0.047(2) 0.0121(18) 0.0007(17) -0.0052(18) C11 0.050(2) 0.066(3) 0.050(2) 0.003(2) 0.0047(19) -0.006(2) C12 0.055(3) 0.082(4) 0.051(2) 0.013(2) 0.0089(19) -0.011(2) C13 0.050(3) 0.066(3) 0.077(3) 0.025(3) 0.003(2) -0.016(2) C14 0.066(3) 0.047(3) 0.089(3) 0.009(2) -0.001(3) -0.017(2) C15 0.054(3) 0.061(3) 0.062(3) 0.008(2) 0.007(2) -0.006(2) C16A 0.081(2) 0.089(3) 0.112(2) 0.0471(16) 0.0253(14) -0.0285(15) C16B 0.0606(15) 0.0843(16) 0.0824(14) 0.0101(9) 0.0080(9) 0.0233(11) C17 0.053(2) 0.052(3) 0.045(2) 0.0017(19) 0.0003(18) -0.015(2) C18 0.061(3) 0.064(3) 0.044(2) -0.002(2) 0.0083(19) -0.014(2) C19 0.064(3) 0.091(4) 0.044(2) -0.003(2) 0.007(2) -0.025(3) C20 0.082(4) 0.062(3) 0.076(3) 0.015(3) -0.001(3) -0.013(3) C21 0.065(3) 0.066(3) 0.064(3) 0.008(2) 0.014(2) -0.011(2) C22 0.057(3) 0.042(2) 0.046(2) 0.0057(18) 0.0109(18) -0.001(2) C23 0.067(3) 0.046(3) 0.075(3) -0.011(2) 0.007(2) 0.009(2) C24 0.070(3) 0.060(3) 0.079(3) -0.012(2) 0.011(2) 0.024(3) C25 0.060(3) 0.060(3) 0.053(2) 0.014(2) 0.016(2) 0.019(2) C26 0.060(3) 0.057(3) 0.052(2) 0.008(2) 0.0128(19) -0.004(2) C27 0.055(3) 0.055(3) 0.049(2) -0.0007(19) 0.0173(19) 0.007(2) N1 0.048(2) 0.068(3) 0.0467(19) 0.0138(18) 0.0048(16) -0.002(2) N2 0.076(3) 0.090(3) 0.049(2) 0.015(2) 0.001(2) -0.041(3) Cl1A 0.0606(15) 0.0843(16) 0.0824(14) 0.0101(9) 0.0080(9) 0.0233(11) Cl1B 0.081(2) 0.089(3) 0.112(2) 0.0471(16) 0.0253(14) -0.0285(15) Br1 0.0504(3) 0.0579(3) 0.0864(3) -0.0066(2) 0.0023(2) 0.0059(2) Br2 0.1110(5) 0.0773(4) 0.0605(3) 0.0080(2) 0.0306(3) -0.0312(3) O1 0.147(8) 0.078(5) 0.120(6) -0.022(4) 0.035(5) -0.025(4) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 1.385(6) . ? C1 H1 0.95 . ? C2 H2 0.95 . ? C3 C2 1.406(6) . ? C3 C4 1.385(6) . ? C3 C6 1.507(5) . ? C4 H4 0.95 . ? C5 C4 1.353(6) . ? C5 H5 0.95 . ? C6 H6 0.9800(11) . ? C7 C6 1.572(6) . ? C7 H7 1 . ? C8 C7 1.542(5) . ? C8 H8 1 . ? C9 C6 1.554(5) . ? C9 C8 1.574(5) . ? C9 H9 1 . ? C10 C11 1.377(5) . ? C10 C15 1.381(6) . ? C10 C9 1.518(5) . ? C11 C12 1.385(6) . ? C11 H11 0.95 . ? C12 C13 1.364(6) . ? C12 H12 0.95 . ? C13 C14 1.374(7) . ? C14 H14 0.95 . ? C15 C14 1.410(6) . ? C15 H15 0.9300(10) . ? C16A C13 1.506(10) . ? C16A H16A 0.98 . ? C16A H16B 0.98 . ? C16A H16C 0.98 . ? C16B C25 1.509(10) . ? C16B H16D 0.98 . ? C16B H16E 0.98 . ? C16B H16F 0.98 . ? C17 C21 1.376(6) . ? C17 C7 1.506(5) . ? C18 C17 1.369(6) . ? C18 C19 1.360(6) . ? C18 H18 0.95 . ? C19 H19 0.95 . ? C19 N2 1.316(7) . ? C20 H20 0.95 . ? C21 C20 1.382(6) . ? C21 H21 0.95 . ? C22 C23 1.378(6) . ? C22 C27 1.368(6) . ? C22 C8 1.517(6) . ? C23 H23 0.95 . ? C24 C23 1.383(6) . ? C24 H24 0.95 . ? C25 C24 1.380(7) . ? C26 C25 1.378(6) . ? C26 H26 0.95 . ? C27 C26 1.409(6) . ? C27 H27 0.95 . ? N1 C1 1.324(6) . ? N1 C5 1.319(6) . ? N1 H1N 0.950(2) . ? N2 C20 1.340(7) . ? N2 H2N 0.950(2) . ? O1 H111 0.9000(11) . ? O1 H222 0.9000(10) . ? Cl1A C25 1.754(5) . ? Cl1B C13 1.732(5) . ? 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 C1 C2 C3 119.2(4) . . ? C1 C2 H2 120.4 . . ? C1 N1 H1N 127(4) . . ? C2 C1 H1 120.2 . . ? C2 C3 C6 123.1(4) . . ? C3 C2 H2 120.4 . . ? C3 C4 H4 119.7 . . ? C3 C6 C7 117.0(3) . . ? C3 C6 C9 115.6(3) . . ? C3 C6 H6 109(3) . . ? C4 C3 C2 117.4(4) . . ? C4 C3 C6 119.4(4) . . ? C4 C5 H5 119.7 . . ? C5 C4 C3 120.6(4) . . ? C5 C4 H4 119.7 . . ? C5 N1 C1 122.6(4) . . ? C5 N1 H1N 110(4) . . ? C6 C7 H7 108.2 . . ? C6 C9 C8 89.7(3) . . ? C6 C9 H9 111.4 . . ? C7 C6 H6 110(3) . . ? C7 C8 C9 88.4(3) . . ? C7 C8 H8 108.5 . . ? C8 C7 C6 90.3(3) . . ? C8 C7 H7 108.2 . . ? C8 C9 H9 111.4 . . ? C9 C6 C7 88.1(3) . . ? C9 C6 H6 116(3) . . ? C9 C8 H8 108.5 . . ? C10 C11 C12 120.7(4) . . ? C10 C11 H11 119.6 . . ? C10 C15 C14 119.9(4) . . ? C10 C15 H15 126(3) . . ? C10 C9 C6 116.7(3) . . ? C10 C9 C8 114.5(3) . . ? C10 C9 H9 111.4 . . ? C11 C10 C15 119.2(4) . . ? C11 C10 C9 116.9(4) . . ? C11 C12 H12 119.8 . . ? C12 C11 H11 119.6 . . ? C12 C13 C14 120.3(4) . . ? C12 C13 C16A 120.9(8) . . ? C12 C13 Cl1B 122.0(4) . . ? C13 C12 C11 120.3(4) . . ? C13 C12 H12 119.8 . . ? C13 C14 C15 119.6(4) . . ? C13 C14 H14 120.2 . . ? C13 C16A H16A 109.5 . . ? C13 C16A H16B 109.5 . . ? C13 C16A H16C 109.5 . . ? C14 C13 C16A 118.9(8) . . ? C14 C13 Cl1B 117.7(5) . . ? C14 C15 H15 114(3) . . ? C15 C10 C9 123.8(4) . . ? C15 C14 H14 120.2 . . ? C17 C18 H18 119.9 . . ? C17 C21 C20 120.2(5) . . ? C17 C21 H21 119.9 . . ? C17 C7 C6 121.1(3) . . ? C17 C7 C8 119.4(3) . . ? C17 C7 H7 108.2 . . ? C18 C17 C21 118.2(4) . . ? C18 C17 C7 121.1(4) . . ? C18 C19 H19 119.6 . . ? C19 C18 C17 120.1(5) . . ? C19 C18 H18 119.9 . . ? C19 N2 C20 121.9(4) . . ? C19 N2 H2N 113(3) . . ? C20 C21 H21 119.9 . . ? C20 N2 H2N 125(3) . . ? C21 C17 C7 120.7(4) . . ? C21 C20 H20 120.6 . . ? C22 C23 C24 121.5(4) . . ? C22 C23 H23 119.2 . . ? C22 C27 C26 122.0(4) . . ? C22 C27 H27 119 . . ? C22 C8 C7 121.0(3) . . ? C22 C8 C9 120.0(3) . . ? C22 C8 H8 108.5 . . ? C23 C22 C8 120.3(4) . . ? C23 C24 H24 119.5 . . ? C24 C23 H23 119.2 . . ? C24 C25 C16B 120.8(9) . . ? C24 C25 Cl1A 121.1(4) . . ? C25 C16B H16D 109.5 . . ? C25 C16B H16E 109.5 . . ? C25 C16B H16F 109.5 . . ? C25 C24 C23 120.9(4) . . ? C25 C24 H24 119.5 . . ? C25 C26 C27 119.5(4) . . ? C25 C26 H26 120.3 . . ? C26 C25 C16B 120.6(9) . . ? C26 C25 C24 118.6(4) . . ? C26 C25 Cl1A 120.3(4) . . ? C26 C27 H27 119 . . ? C27 C22 C23 117.5(4) . . ? C27 C22 C8 122.1(4) . . ? C27 C26 H26 120.3 . . ? H16D C16B H16E 109.5 . . ? H16D C16B H16F 109.5 . . ? H16E C16B H16F 109.5 . . ? H222 O1 H111 107.32(17) . . ? N1 C1 C2 119.7(4) . . ? N1 C1 H1 120.2 . . ? N1 C5 C4 120.5(4) . . ? N1 C5 H5 119.7 . . ? N2 C19 C18 120.7(5) . . ? N2 C19 H19 119.6 . . ? N2 C20 C21 118.8(5) . . ? N2 C20 H20 120.6 . . ? #------------------ SECTION 2. COMPOUND(S) DETAILS -------------------------# data_Cl-PE _database_code_depnum_ccdc_archive 'CCDC 809487' #TrackingRef 'ClPE.cif' _audit_creation_date 2011-01-23T18:28:33-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_formula_sum 'C13 H10 Cl N' _chemical_formula_moiety 'C13 H10 Cl N' _chemical_formula_weight 215.67 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _cell_length_a 9.4815(10) _cell_length_b 9.6019(12) _cell_length_c 14.2885(18) _cell_angle_alpha 71.745(5) _cell_angle_beta 76.746(6) _cell_angle_gamma 62.801(5) _cell_volume 1093.0(2) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 25.35 _cell_measurement_reflns_used 3523 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.08 _exptl_crystal_density_diffrn 1.311 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.312 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'HKL Scalepack (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.9345 _exptl_absorpt_correction_T_max 0.9754 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_reflns_av_R_equivalents 0.0641 _diffrn_reflns_av_unetI/netI 0.093 _diffrn_reflns_number 6753 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 24.99 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.98 _diffrn_measured_fraction_theta_max 0.98 _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD phi and omega scans' _diffrn_detector_area_resol_mean 9 _reflns_number_total 3773 _reflns_number_gt 1760 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL Denzo, Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL (Sheldrick, 2008)' _computing_molecular_graphics 'Mercury (Macrae, 2008)' _computing_publication_material 'WinGX (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # 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^ > 2\s(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. A total of 91 geometrical restraints (i.e. SAME, SADI, DFIX, DELU) and constraints (i.e. EADP) were utilized to model both crystallographically independent olefins. A checkCIF report revealed a series of level-C alerts that are attributed to the poor diffractibility of the investigated single crystal. Numerous attempts to growth sizable single crystals of better quality were unsuccessful. ; _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^)+(0.1737P)^2^+0.5511P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 3773 _refine_ls_number_parameters 293 _refine_ls_number_restraints 91 _refine_ls_R_factor_all 0.2106 _refine_ls_R_factor_gt 0.1168 _refine_ls_wR_factor_ref 0.3451 _refine_ls_wR_factor_gt 0.2928 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.051 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.412 _refine_diff_density_min -0.371 _refine_diff_density_rms 0.08 #----------------------------------------------------------------------------# # 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 C1 C 0.3936(7) 0.6439(9) -0.4154(5) 0.093(2) Uani 1 1 d D C . C2 C 0.3816(6) 0.6643(8) -0.3235(4) 0.0800(19) Uani 1 1 d D . . C3 C 0.2342(6) 0.7536(7) -0.2797(4) 0.0732(17) Uani 1 1 d DU C . C4 C 0.1057(6) 0.8191(8) -0.3351(4) 0.084(2) Uani 1 1 d D . . C5 C 0.1313(7) 0.7900(8) -0.4264(5) 0.092(2) Uani 1 1 d D C . C6 C 0.2117(7) 0.7704(7) -0.1758(4) 0.0853(19) Uani 1 1 d DU . . C7 C 0.3156(7) 0.7265(7) -0.1194(5) 0.0764(17) Uani 1 1 d DU C . C8 C 0.2970(8) 0.7368(7) -0.0156(5) 0.0724(16) Uani 1 1 d U C . C9 C 0.4297(7) 0.6958(7) 0.0299(4) 0.0727(17) Uani 1 1 d D C . C10 C 0.4164(7) 0.7064(7) 0.1233(5) 0.0728(17) Uani 1 1 d . C . C11 C 0.2719(8) 0.7610(7) 0.1773(5) 0.0732(17) Uani 1 1 d . C . C12 C 0.1351(8) 0.8016(8) 0.1331(5) 0.0839(19) Uani 1 1 d U C . C13 C 0.1496(7) 0.7918(8) 0.0365(5) 0.0864(19) Uani 1 1 d DU C . C14A C 0.1313(15) 0.4109(12) 0.8909(6) 0.066(2) Uani 0.625(6) 1 d PDU B 1 C14B C 0.143(3) 0.395(2) 0.9161(12) 0.066(2) Uani 0.375(6) 1 d PDU B 2 C15A C 0.158(4) 0.3873(10) 0.7981(8) 0.066(2) Uani 0.625(6) 1 d PDU B 1 C15B C 0.144(7) 0.418(2) 0.8169(13) 0.066(2) Uani 0.375(6) 1 d PD B 2 C16A C 0.249(2) 0.2321(9) 0.7840(5) 0.064(2) Uani 0.625(6) 1 d PD B 1 C16B C 0.224(4) 0.2849(17) 0.7754(10) 0.064(2) Uani 0.375(6) 1 d PD B 2 C17A C 0.3082(14) 0.1118(10) 0.8674(5) 0.068(2) Uani 0.625(6) 1 d PDU B 1 C17B C 0.303(3) 0.1380(17) 0.8391(11) 0.068(2) Uani 0.375(6) 1 d PDU B 2 C18A C 0.276(4) 0.1494(16) 0.9563(8) 0.076(3) Uani 0.625(6) 1 d PD B 1 C18B C 0.294(8) 0.129(3) 0.9370(14) 0.076(3) Uani 0.375(6) 1 d PD B 2 C19A C 0.2706(12) 0.1960(8) 0.6856(5) 0.069(3) Uani 0.625(6) 1 d PD B 1 C19B C 0.231(2) 0.3020(17) 0.6667(9) 0.069(3) Uani 0.375(6) 1 d PD B 2 C20A C 0.2238(11) 0.3043(10) 0.6041(4) 0.066(2) Uani 0.625(6) 1 d PD B 1 C20B C 0.265(2) 0.1884(17) 0.6231(10) 0.066(2) Uani 0.375(6) 1 d PD B 2 C21A C 0.2457(17) 0.2723(12) 0.5043(5) 0.066(3) Uani 0.625(6) 1 d PGD B 1 C21B C 0.246(3) 0.212(2) 0.5172(8) 0.066(3) Uani 0.375(6) 1 d PGD B 2 C22A C 0.2012(18) 0.4077(11) 0.4257(6) 0.069(3) Uani 0.625(6) 1 d PG B 1 C22B C 0.196(3) 0.363(2) 0.4508(9) 0.069(3) Uani 0.375(6) 1 d PG B 2 C23A C 0.2022(15) 0.3913(10) 0.3322(5) 0.078(2) Uani 0.625(6) 1 d PGDU B 1 C23B C 0.212(3) 0.3739(19) 0.3498(9) 0.078(2) Uani 0.375(6) 1 d PGDU B 2 C24A C 0.2477(10) 0.2395(11) 0.3174(5) 0.0657(18) Uani 0.625(6) 1 d PGD B 1 C24B C 0.2795(18) 0.235(2) 0.3152(9) 0.0657(18) Uani 0.375(6) 1 d PGD B 2 C25A C 0.2922(15) 0.1041(10) 0.3961(6) 0.072(3) Uani 0.625(6) 1 d PGD B 1 C25B C 0.330(3) 0.0841(19) 0.3816(12) 0.072(3) Uani 0.375(6) 1 d PGD B 2 C26A C 0.2912(17) 0.1205(11) 0.4895(5) 0.076(3) Uani 0.625(6) 1 d PG B 1 C26B C 0.313(3) 0.073(2) 0.4826(11) 0.076(3) Uani 0.375(6) 1 d PG B 2 H1 H 0.4943 0.5843 -0.4431 0.112 Uiso 1 1 calc R . . H2 H 0.4719 0.6184 -0.2901 0.096 Uiso 1 1 calc R C . H4 H 0.0039 0.8817 -0.3103 0.1 Uiso 1 1 calc R C . H5 H 0.0435 0.8346 -0.4619 0.11 Uiso 1 1 calc R . . H6 H 0.1066 0.8199 -0.1498 0.102 Uiso 1 1 calc R A . H7 H 0.4204 0.6804 -0.1469 0.092 Uiso 1 1 calc R C . H9 H 0.5302 0.6602 -0.005 0.087 Uiso 1 1 calc R C . H10 H 0.5082 0.6757 0.1519 0.087 Uiso 1 1 calc R C . H12 H 0.0351 0.835 0.169 0.101 Uiso 1 1 calc R C . H13 H 0.0589 0.8227 0.0067 0.104 Uiso 1 1 calc R C . H14A H 0.0699 0.5156 0.8984 0.08 Uiso 0.625(6) 1 calc PR B 1 H14B H 0.0849 0.4849 0.9427 0.08 Uiso 0.375(6) 1 calc PR B 2 H15A H 0.1154 0.4735 0.745 0.08 Uiso 0.625(6) 1 calc PR B 1 H15B H 0.0914 0.5202 0.7777 0.08 Uiso 0.375(6) 1 calc PR B 2 H17A H 0.3697 0.0057 0.8625 0.082 Uiso 0.625(6) 1 calc PR B 1 H17B H 0.362 0.0459 0.8149 0.082 Uiso 0.375(6) 1 calc PR B 2 H18A H 0.3196 0.0665 1.0106 0.091 Uiso 0.625(6) 1 calc PR B 1 H18B H 0.3424 0.0281 0.9786 0.091 Uiso 0.375(6) 1 calc PR B 2 H19A H 0.3211 0.0884 0.6826 0.083 Uiso 0.625(6) 1 calc PR B 1 H19B H 0.2073 0.4051 0.6261 0.083 Uiso 0.375(6) 1 calc PR B 2 H20A H 0.172 0.4114 0.608 0.079 Uiso 0.625(6) 1 calc PR B 1 H20B H 0.3061 0.0827 0.661 0.079 Uiso 0.375(6) 1 calc PR B 2 H22A H 0.1708 0.5093 0.4355 0.082 Uiso 0.625(6) 1 calc PR B 1 H22B H 0.1507 0.4562 0.474 0.082 Uiso 0.375(6) 1 calc PR B 2 H23A H 0.1725 0.4819 0.2796 0.093 Uiso 0.625(6) 1 calc PR B 1 H23B H 0.179 0.4746 0.3054 0.093 Uiso 0.375(6) 1 calc PR B 2 H25A H 0.3226 0.0025 0.3862 0.086 Uiso 0.625(6) 1 calc PR B 1 H25B H 0.3745 -0.0091 0.3585 0.086 Uiso 0.375(6) 1 calc PR B 2 H26A H 0.3209 0.0299 0.5421 0.091 Uiso 0.625(6) 1 calc PR B 1 H26B H 0.3462 -0.0275 0.527 0.091 Uiso 0.375(6) 1 calc PR B 2 N1 N 0.2713(7) 0.7033(8) -0.4686(4) 0.0931(18) Uani 1 1 d D . . N2A N 0.186(4) 0.2967(16) 0.9713(8) 0.072(3) Uani 0.625(6) 1 d PD B 1 N2B N 0.220(7) 0.256(3) 0.9775(14) 0.072(3) Uani 0.375(6) 1 d PD B 2 Cl1 Cl 0.2576(2) 0.7694(2) 0.29823(13) 0.0982(8) Uani 1 1 d . C . Cl2A Cl 0.261(2) 0.2177(17) 0.1990(5) 0.094(2) Uani 0.625(6) 1 d PD B 1 Cl2B Cl 0.274(4) 0.249(3) 0.1917(10) 0.094(2) Uani 0.375(6) 1 d PD B 2 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 0.079(5) 0.122(6) 0.091(5) -0.046(5) -0.001(4) -0.043(4) C2 0.068(4) 0.085(5) 0.089(5) -0.022(4) -0.017(3) -0.028(4) C3 0.079(4) 0.067(4) 0.084(4) -0.023(3) -0.002(3) -0.038(3) C4 0.059(4) 0.085(5) 0.105(6) -0.016(4) -0.015(4) -0.029(3) C5 0.095(6) 0.102(6) 0.084(5) -0.006(4) -0.030(4) -0.047(5) C6 0.095(5) 0.077(5) 0.091(4) -0.029(4) -0.011(4) -0.036(4) C7 0.078(4) 0.079(4) 0.084(4) -0.019(4) -0.014(3) -0.040(4) C8 0.082(4) 0.067(4) 0.075(3) -0.007(3) -0.014(3) -0.042(3) C9 0.071(4) 0.077(4) 0.073(4) -0.018(3) -0.007(3) -0.033(3) C10 0.067(4) 0.073(4) 0.076(4) -0.015(3) -0.008(3) -0.028(3) C11 0.082(4) 0.063(4) 0.081(4) -0.020(3) 0.001(4) -0.038(3) C12 0.067(4) 0.084(5) 0.101(4) -0.020(4) 0.000(4) -0.038(4) C13 0.070(3) 0.090(5) 0.104(4) -0.017(4) -0.021(3) -0.037(4) C14A 0.067(2) 0.067(2) 0.066(3) -0.0161(14) -0.0074(14) -0.0278(15) C14B 0.067(2) 0.067(2) 0.066(3) -0.0161(14) -0.0074(14) -0.0278(15) C15A 0.068(7) 0.062(6) 0.072(5) -0.024(4) -0.006(7) -0.026(7) C15B 0.068(7) 0.062(6) 0.072(5) -0.024(4) -0.006(7) -0.026(7) C16A 0.055(7) 0.071(8) 0.075(5) -0.024(5) -0.006(4) -0.031(7) C16B 0.055(7) 0.071(8) 0.075(5) -0.024(5) -0.006(4) -0.031(7) C17A 0.068(2) 0.068(2) 0.068(3) -0.0158(15) -0.0076(14) -0.0286(15) C17B 0.068(2) 0.068(2) 0.068(3) -0.0158(15) -0.0076(14) -0.0286(15) C18A 0.088(10) 0.068(6) 0.076(7) -0.017(5) -0.014(9) -0.035(6) C18B 0.088(10) 0.068(6) 0.076(7) -0.017(5) -0.014(9) -0.035(6) C19A 0.081(6) 0.052(6) 0.084(7) -0.031(6) -0.002(5) -0.030(6) C19B 0.081(6) 0.052(6) 0.084(7) -0.031(6) -0.002(5) -0.030(6) C20A 0.068(6) 0.060(6) 0.077(6) -0.017(6) -0.012(5) -0.030(6) C20B 0.068(6) 0.060(6) 0.077(6) -0.017(6) -0.012(5) -0.030(6) C21A 0.065(4) 0.083(11) 0.073(6) -0.015(6) 0.000(4) -0.055(7) C21B 0.065(4) 0.083(11) 0.073(6) -0.015(6) 0.000(4) -0.055(7) C22A 0.082(5) 0.077(8) 0.060(7) -0.013(6) 0.012(5) -0.055(6) C22B 0.082(5) 0.077(8) 0.060(7) -0.013(6) 0.012(5) -0.055(6) C23A 0.077(2) 0.078(2) 0.078(2) -0.0179(14) -0.0083(13) -0.0327(15) C23B 0.077(2) 0.078(2) 0.078(2) -0.0179(14) -0.0083(13) -0.0327(15) C24A 0.045 0.094(5) 0.066(4) -0.013(4) 0.004(3) -0.044(3) C24B 0.045 0.094(5) 0.066(4) -0.013(4) 0.004(3) -0.044(3) C25A 0.043(7) 0.074(5) 0.088(6) -0.034(4) 0.020(5) -0.020(4) C25B 0.043(7) 0.074(5) 0.088(6) -0.034(4) 0.020(5) -0.020(4) C26A 0.067(6) 0.077(8) 0.075(5) -0.021(5) -0.004(4) -0.023(7) C26B 0.067(6) 0.077(8) 0.075(5) -0.021(5) -0.004(4) -0.023(7) N1 0.097(5) 0.121(5) 0.073(4) -0.033(3) -0.004(3) -0.051(4) N2A 0.072(14) 0.064(9) 0.080(4) -0.015(5) -0.013(4) -0.027(8) N2B 0.072(14) 0.064(9) 0.080(4) -0.015(5) -0.013(4) -0.027(8) Cl1 0.1238(16) 0.0983(14) 0.0813(13) -0.0338(10) 0.0015(10) -0.0512(12) Cl2A 0.099(3) 0.128(5) 0.0740(16) -0.033(2) 0.0080(19) -0.066(4) Cl2B 0.099(3) 0.128(5) 0.0740(16) -0.033(2) 0.0080(19) -0.066(4) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 N1 1.333(6) . ? C2 C1 1.359(6) . ? C3 C2 1.385(6) . ? C3 C4 1.392(6) . ? C5 C4 1.363(6) . ? C6 C3 1.500(8) . ? C6 C7 1.253(7) . ? C7 C8 1.482(9) . ? C9 C8 1.387(8) . ? C10 C11 1.363(8) . ? C10 C9 1.342(8) . ? C12 C11 1.411(9) . ? C12 C13 1.385(9) . ? C13 C8 1.371(8) . ? C14A C15A 1.363(6) . ? C14B C15B 1.363(6) . ? C16A C15A 1.392(6) . ? C16A C17A 1.385(6) . ? C16B C15B 1.392(6) . ? C16B C17B 1.385(6) . ? C17A C18A 1.359(6) . ? C17B C18B 1.360(6) . ? C18A N2A 1.333(6) . ? C18B N2B 1.333(6) . ? C19A C16A 1.4996(9) . ? C19A C20A 1.3000(9) . ? C19B C16B 1.4995(9) . ? C19B C20B 1.3000(9) . ? C20A C21A 1.4999 . ? C20B C21B 1.4999 . ? C21A C22A 1.39 . ? C21A C26A 1.39 . ? C21B C22B 1.39 . ? C21B C26B 1.39 . ? C22A C23A 1.39 . ? C22B C23B 1.39 . ? C23A C24A 1.39 . ? C23B C24B 1.39 . ? C24A C25A 1.39 . ? C24A Cl2A 1.7397(10) . ? C24B C25B 1.39 . ? C24B Cl2B 1.7398(11) . ? C25A C26A 1.39 . ? C25B C26B 1.39 . ? N1 C5 1.325(6) . ? N2A C14A 1.325(6) . ? N2B C14B 1.325(6) . ? Cl1 C11 1.727(7) . ? 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 C1 C2 C3 119.7(5) . . ? C2 C3 C4 116.4(4) . . ? C2 C3 C6 122.1(4) . . ? C4 C3 C6 121.5(4) . . ? C5 C4 C3 119.0(4) . . ? C5 N1 C1 115.1(4) . . ? C6 C7 C8 129.8(6) . . ? C7 C6 C3 128.6(5) . . ? C8 C13 C12 120.4(6) . . ? C9 C10 C11 121.8(6) . . ? C9 C8 C7 120.1(5) . . ? C10 C11 C12 117.9(6) . . ? C10 C11 Cl1 121.1(5) . . ? C10 C9 C8 121.5(6) . . ? C12 C11 Cl1 121.0(5) . . ? C13 C12 C11 120.0(6) . . ? C13 C8 C7 121.4(5) . . ? C13 C8 C9 118.4(6) . . ? C14A C15A C16A 119.0(4) . . ? C14A N2A C18A 115.1(5) . . ? C14B C15B C16B 118.9(5) . . ? C14B N2B C18B 115.1(5) . . ? C15A C16A C19A 121.4(4) . . ? C15B C16B C19B 121.5(4) . . ? C17A C16A C15A 116.4(4) . . ? C17A C16A C19A 122.0(4) . . ? C17B C16B C15B 116.4(4) . . ? C17B C16B C19B 122.0(4) . . ? C18A C17A C16A 119.7(5) . . ? C18B C17B C16B 119.7(5) . . ? C19A C20A C21A 126.1(8) . . ? C19B C20B C21B 125.8(15) . . ? C20A C19A C16A 124.8(6) . . ? C20B C19B C16B 127.1(13) . . ? C21B C22B C23B 120 . . ? C22A C21A C20A 115.9(6) . . ? C22A C21A C26A 120 . . ? C22A C23A C24A 120 . . ? C22B C21B C20B 123.1(11) . . ? C22B C21B C26B 120 . . ? C22B C23B C24B 120 . . ? C23A C22A C21A 120 . . ? C23A C24A Cl2A 119.9 . . ? C23B C24B Cl2B 119.66(14) . . ? C24A C25A C26A 120 . . ? C25A C24A C23A 120 . . ? C25A C24A Cl2A 119.9 . . ? C25A C26A C21A 120 . . ? C25B C24B C23B 120 . . ? C25B C24B Cl2B 119.66(14) . . ? C25B C26B C21B 120 . . ? C26A C21A C20A 123.8(6) . . ? C26B C21B C20B 115.6(12) . . ? C26B C25B C24B 120 . . ? N1 C1 C2 124.6(5) . . ? N1 C5 C4 125.3(5) . . ? N2A C14A C15A 125.2(5) . . ? N2A C18A C17A 124.6(5) . . ? N2B C14B C15B 125.2(5) . . ? N2B C18B C17B 124.5(5) . . ? #------------------ SECTION 2. COMPOUND(S) DETAILS -------------------------# data_Me-PE _database_code_depnum_ccdc_archive 'CCDC 809488' #TrackingRef 'MePE.cif' _audit_creation_date 2011-01-19T13:17:54-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_formula_sum 'C14 H13 N' _chemical_formula_moiety 'C14 H13 N' _chemical_formula_weight 195.25 _chemical_absolute_configuration unk #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' _cell_length_a 6.0339(7) _cell_length_b 7.6092(9) _cell_length_c 23.135(3) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1062.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 25.35 _cell_measurement_reflns_used 3667 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.03 _exptl_crystal_density_diffrn 1.221 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 416 #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.071 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'HKL Scalepack (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.9756 _exptl_absorpt_correction_T_max 0.9979 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_reflns_av_R_equivalents 0.0379 _diffrn_reflns_av_unetI/netI 0.0231 _diffrn_reflns_number 6496 _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 -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.82 _diffrn_reflns_theta_max 24.99 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD phi and omega scans' _diffrn_detector_area_resol_mean 9 _reflns_number_total 1117 _reflns_number_gt 933 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL Denzo, Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL (Sheldrick, 2008)' _computing_molecular_graphics 'Mercury (Macrae, 2008)' _computing_publication_material 'WinGX (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # 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^ > 2\s(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^)+(0.0603P)^2^+0.0108P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 1117 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0486 _refine_ls_R_factor_gt 0.038 _refine_ls_wR_factor_ref 0.0973 _refine_ls_wR_factor_gt 0.0929 _refine_ls_goodness_of_fit_ref 1.151 _refine_ls_restrained_S_all 1.151 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.15 _refine_diff_density_min -0.168 _refine_diff_density_rms 0.036 #----------------------------------------------------------------------------# # 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' 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 1.0410(4) 0.2885(3) 0.55524(9) 0.0362(6) Uani 1 1 d . . . C2 C 0.8924(4) 0.2685(3) 0.59953(8) 0.0333(6) Uani 1 1 d . . . C3 C 0.9415(3) 0.3313(3) 0.65472(8) 0.0287(5) Uani 1 1 d . . . C4 C 1.1463(3) 0.4158(3) 0.66043(8) 0.0309(5) Uani 1 1 d . . . C5 C 1.2841(4) 0.4316(3) 0.61321(8) 0.0352(6) Uani 1 1 d . . . C6 C 0.7840(3) 0.3075(3) 0.70217(8) 0.0306(5) Uani 1 1 d . . . C7 C 0.7968(3) 0.3801(2) 0.75438(8) 0.0306(5) Uani 1 1 d . . . C8 C 0.6373(3) 0.3632(3) 0.80182(8) 0.0276(5) Uani 1 1 d . . . C9 C 0.4319(3) 0.2799(3) 0.79575(8) 0.0314(5) Uani 1 1 d . . . C10 C 0.2893(4) 0.2633(3) 0.84191(8) 0.0313(5) Uani 1 1 d . . . C11 C 0.3445(3) 0.3251(3) 0.89668(8) 0.0305(5) Uani 1 1 d . . . C12 C 0.5453(3) 0.4116(3) 0.90257(8) 0.0331(5) Uani 1 1 d . . . C13 C 0.6893(4) 0.4310(3) 0.85627(8) 0.0324(5) Uani 1 1 d . . . C14 C 0.1937(4) 0.2952(3) 0.94745(9) 0.0414(6) Uani 1 1 d . . . H1 H 1.0018 0.2428 0.5184 0.043 Uiso 1 1 calc R . . H2 H 0.7549 0.2115 0.5926 0.04 Uiso 1 1 calc R . . H4 H 1.1903 0.4621 0.6968 0.037 Uiso 1 1 calc R . . H5 H 1.4209 0.4914 0.6184 0.042 Uiso 1 1 calc R . . H6 H 0.6607 0.233 0.695 0.037 Uiso 1 1 calc R . . H7 H 0.9235 0.4508 0.7617 0.037 Uiso 1 1 calc R . . H9 H 0.39 0.234 0.7592 0.038 Uiso 1 1 calc R . . H10 H 0.1497 0.2083 0.8362 0.038 Uiso 1 1 calc R . . h12 H 0.5852 0.4587 0.9391 0.04 Uiso 1 1 calc R . . H13 H 0.8255 0.4914 0.8617 0.039 Uiso 1 1 calc R . . H14A H 0.2596 0.3474 0.9822 0.062 Uiso 0.5 1 calc PR . . H14B H 0.1736 0.1687 0.9534 0.062 Uiso 0.5 1 calc PR . . H14C H 0.0497 0.35 0.9399 0.062 Uiso 0.5 1 calc PR . . H14D H 0.0623 0.23 0.9348 0.062 Uiso 0.5 1 calc PR . . H14E H 0.1483 0.4087 0.9636 0.062 Uiso 0.5 1 calc PR . . H14F H 0.2723 0.2274 0.9771 0.062 Uiso 0.5 1 calc PR . . N1 N 1.2383(3) 0.3686(2) 0.56047(7) 0.0383(5) 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 0.0398(13) 0.0374(13) 0.0315(11) -0.0017(10) -0.0027(11) 0.0020(12) C2 0.0315(12) 0.0343(12) 0.0341(12) -0.0009(9) -0.0049(10) -0.0019(10) C3 0.0290(11) 0.0247(11) 0.0325(11) 0.0017(9) -0.0027(9) 0.0024(10) C4 0.0342(12) 0.0291(12) 0.0293(11) -0.0008(9) -0.0022(10) 0.0007(10) C5 0.0341(12) 0.0312(12) 0.0402(12) 0.0001(10) 0.0010(11) -0.0035(11) C6 0.0288(11) 0.0274(10) 0.0355(11) 0.0025(9) -0.0008(10) -0.0022(10) C7 0.0277(11) 0.0262(10) 0.0378(11) 0.0027(10) -0.0030(9) -0.0012(10) C8 0.0284(11) 0.0246(10) 0.0299(11) 0.0031(9) -0.0014(9) 0.0025(9) C9 0.0342(12) 0.0296(12) 0.0305(11) -0.0007(9) -0.0044(10) -0.0013(10) C10 0.0269(10) 0.0293(11) 0.0377(11) 0.0027(9) -0.0025(10) -0.0022(10) C11 0.0313(12) 0.0279(12) 0.0324(11) 0.0027(9) -0.0006(9) 0.0038(10) C12 0.0352(12) 0.0348(13) 0.0292(11) -0.0031(10) -0.0033(10) -0.0006(11) C13 0.0286(11) 0.0297(12) 0.0389(12) -0.0017(9) -0.0032(10) -0.0011(10) C14 0.0412(13) 0.0441(13) 0.0390(12) 0.0020(10) 0.0039(11) -0.0031(12) N1 0.0409(11) 0.0391(11) 0.0349(10) -0.0003(9) 0.0032(9) -0.0007(10) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 H1 0.95 . ? C2 C1 1.370(3) . ? C2 C3 1.395(3) . ? C2 H2 0.95 . ? C4 C3 1.399(3) . ? C4 C5 1.378(3) . ? C4 H4 0.95 . ? C5 H5 0.95 . ? C5 N1 1.340(2) . ? C6 C3 1.463(3) . ? C6 C7 1.330(3) . ? C6 H6 0.95 . ? C7 H7 0.95 . ? C8 C7 1.466(3) . ? C9 C8 1.399(3) . ? C9 H9 0.95 . ? C10 C11 1.392(3) . ? C10 C9 1.377(3) . ? C10 H10 0.95 . ? C11 C12 1.385(3) . ? C11 C14 1.503(3) . ? C12 h12 0.95 . ? C13 C12 1.387(3) . ? C13 C8 1.397(3) . ? C13 H13 0.95 . ? C14 H14A 0.98 . ? C14 H14B 0.98 . ? C14 H14C 0.98 . ? C14 H14D 0.98 . ? C14 H14E 0.98 . ? C14 H14F 0.98 . ? N1 C1 1.343(3) . ? 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 C1 C2 C3 120.5(2) . . ? C1 C2 H2 119.7 . . ? C2 C1 H1 117.9 . . ? C2 C3 C4 115.54(19) . . ? C2 C3 C6 120.44(19) . . ? C3 C2 H2 119.7 . . ? C3 C4 H4 120.1 . . ? C3 C6 H6 116.9 . . ? C4 C3 C6 124.03(17) . . ? C4 C5 H5 117.8 . . ? C5 C4 C3 119.88(18) . . ? C5 C4 H4 120.1 . . ? C5 N1 C1 115.30(19) . . ? C6 C7 C8 127.24(19) . . ? C6 C7 H7 116.4 . . ? C7 C6 C3 126.29(19) . . ? C7 C6 H6 116.9 . . ? C8 C13 H13 119.5 . . ? C8 C7 H7 116.4 . . ? C8 C9 H9 119.4 . . ? C9 C10 C11 121.7(2) . . ? C9 C10 H10 119.2 . . ? C9 C8 C7 123.13(18) . . ? C10 C11 C14 121.01(19) . . ? C10 C9 C8 121.14(19) . . ? C10 C9 H9 119.4 . . ? C11 C10 H10 119.2 . . ? C11 C12 C13 121.49(18) . . ? C11 C12 h12 119.3 . . ? C11 C14 H14A 109.5 . . ? C11 C14 H14B 109.5 . . ? C11 C14 H14C 109.5 . . ? C11 C14 H14D 109.5 . . ? C11 C14 H14E 109.5 . . ? C11 C14 H14F 109.5 . . ? C12 C11 C10 117.35(18) . . ? C12 C11 C14 121.62(17) . . ? C12 C13 C8 121.1(2) . . ? C12 C13 H13 119.5 . . ? C13 C12 h12 119.3 . . ? C13 C8 C7 119.70(19) . . ? C13 C8 C9 117.17(18) . . ? H14A C14 H14B 109.5 . . ? H14A C14 H14C 109.5 . . ? H14A C14 H14D 141.1 . . ? H14A C14 H14E 56.3 . . ? H14A C14 H14F 56.3 . . ? H14B C14 H14C 109.5 . . ? H14B C14 H14D 56.3 . . ? H14B C14 H14E 141.1 . . ? H14B C14 H14F 56.3 . . ? H14C C14 H14D 56.3 . . ? H14C C14 H14E 56.3 . . ? H14C C14 H14F 141.1 . . ? H14D C14 H14E 109.5 . . ? H14D C14 H14F 109.5 . . ? H14E C14 H14F 109.5 . . ? N1 C1 C2 124.27(19) . . ? N1 C1 H1 117.9 . . ? N1 C5 C4 124.5(2) . . ? N1 C5 H5 117.8 . . ?