# Supplementary Material (ESI) for New Journal of Chemistry # This journal is (c) The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2006 data_global _journal_name_full 'New J.Chem.(Nouv.J.Chim.)' _journal_coden_Cambridge 0440 _audit_update_record ; August 22, 2005 Checkcif ; _publ_contact_author_name 'Pierangelo Metrangolo' _publ_contact_author_address ; NFMLab-DCMIC "G. Natta" Milan 20131 ITALY ; _publ_contact_author_email PIERANGELO.METRANGOLO@POLIMI.IT _publ_section_title ; Solid state synthesis under supramolecular control of a 2D heterotetratopic self-complementary tecton tailored to halogen bonding ; loop_ _publ_author_name 'Pierangelo Metrangolo' 'Giovanni Marras' 'Franck Meyer' 'Tullio Pilati' 'Giuseppe Resnati' # Attachment 'B605958A_Cpd5_revised.CIF' data_re143 _database_code_depnum_ccdc_archive 'CCDC 604217' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ; 1alpha,2alpha,3beta,4beta-1,3-bis(2,3,5,6-tetrafluoro-4-iodo- phenyl)-2,4-bis(4-phenyl-dimethylamine)cyclobutane ; _chemical_formula_moiety '(C32 H24 F8 I2 N2), 2(C H Cl3)' _chemical_formula_sum 'C34 H26 Cl6 F8 I2 N2' _chemical_formula_weight 1081.07 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 '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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.1825(8) _cell_length_b 18.9953(15) _cell_length_c 16.605(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.930(4) _cell_angle_gamma 90.00 _cell_volume 1949.8(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 8139 _cell_measurement_theta_min 2.459 _cell_measurement_theta_max 30.576 _exptl_crystal_description Prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.841 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1048 _exptl_absorpt_coefficient_mu 2.091 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.830425 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details ; SADABS - Bruker/Siemens area detector absorption and other corrections - V2.03 ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD area detector' _diffrn_measurement_method '\w and \f scans' _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 40089 _diffrn_reflns_av_R_equivalents 0.0212 _diffrn_reflns_av_sigmaI/netI 0.0175 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.63 _diffrn_reflns_theta_max 30.59 _reflns_number_total 5976 _reflns_number_gt 5206 _reflns_threshold_expression >2s\(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SIR-92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPIII (Burnett & Johnson,1996)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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. Aromatic H atoms were refined with some restraints (SADI routine of SHELX-97) ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0440P)^2^+0.6752P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5976 _refine_ls_number_parameters 279 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0327 _refine_ls_R_factor_gt 0.0281 _refine_ls_wR_factor_ref 0.0801 _refine_ls_wR_factor_gt 0.0770 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I -0.36432(2) 0.096010(6) 0.398511(7) 0.04766(6) Uani 1 d . . . C1 C 0.0490(3) -0.00564(8) 0.06408(10) 0.0342(3) Uani 1 d . . . H1 H 0.189(3) -0.0296(11) 0.0758(12) 0.034(5) Uiso 1 d . . . C2 C -0.0925(3) -0.05008(8) 0.00480(10) 0.0343(3) Uani 1 d . . . H2 H -0.246(3) -0.0481(11) 0.0186(12) 0.033(5) Uiso 1 d . . . C3 C -0.0509(3) 0.01741(8) 0.14147(10) 0.0342(3) Uani 1 d . . . C4 C 0.0522(3) 0.00639(9) 0.21550(11) 0.0376(3) Uani 1 d . . . C5 C -0.0350(3) 0.02690(10) 0.28747(11) 0.0414(4) Uani 1 d . . . C6 C -0.2334(3) 0.06022(9) 0.29060(11) 0.0409(4) Uani 1 d . . . C7 C -0.3401(3) 0.07109(9) 0.21780(11) 0.0400(3) Uani 1 d . . . C8 C -0.2520(3) 0.04967(9) 0.14618(10) 0.0377(3) Uani 1 d . . . C9 C -0.0430(3) -0.12732(8) -0.00759(10) 0.0351(3) Uani 1 d . . . C10 C 0.1358(4) -0.16179(10) 0.02339(16) 0.0553(5) Uani 1 d D . . H10 H 0.237(4) -0.1367(14) 0.0507(17) 0.071(8) Uiso 1 d D . . C11 C 0.1695(4) -0.23354(11) 0.01086(17) 0.0579(6) Uani 1 d D . . H11 H 0.294(4) -0.2528(17) 0.032(2) 0.088(10) Uiso 1 d D . . C12 C 0.0248(3) -0.27362(8) -0.03374(10) 0.0369(3) Uani 1 d . . . C13 C -0.1572(4) -0.23939(10) -0.06389(14) 0.0513(5) Uani 1 d D . . H13 H -0.258(4) -0.2639(14) -0.0929(16) 0.067(8) Uiso 1 d D . . C14 C -0.1891(3) -0.16792(10) -0.05095(14) 0.0490(5) Uani 1 d D . . H14 H -0.311(4) -0.1468(15) -0.0721(17) 0.072(8) Uiso 1 d D . . N1 N 0.0545(3) -0.34668(8) -0.04388(10) 0.0424(3) Uani 1 d . . . C15 C -0.0759(5) -0.38160(12) -0.10628(16) 0.0648(6) Uani 1 d . . . H15A H -0.0412 -0.4308 -0.1073 0.097 Uiso 1 calc R . . H15B H -0.0457 -0.3611 -0.1577 0.097 Uiso 1 calc R . . H15C H -0.2266 -0.3758 -0.0948 0.097 Uiso 1 calc R . . C16 C 0.2768(4) -0.37303(12) -0.0385(2) 0.0702(7) Uani 1 d . . . H16A H 0.2770 -0.4231 -0.0463 0.105 Uiso 1 calc R . . H16B H 0.3372 -0.3622 0.0137 0.105 Uiso 1 calc R . . H16C H 0.3620 -0.3511 -0.0792 0.105 Uiso 1 calc R . . F1 F 0.24531(19) -0.02670(7) 0.21801(7) 0.0518(3) Uani 1 d . . . F2 F 0.0767(2) 0.01332(8) 0.35589(7) 0.0618(3) Uani 1 d . . . F3 F -0.5331(2) 0.10377(7) 0.21602(9) 0.0546(3) Uani 1 d . . . F4 F -0.3718(2) 0.05971(7) 0.07816(7) 0.0522(3) Uani 1 d . . . C1A C 0.2549(3) 0.70552(9) 0.69060(11) 0.0643(17) Uani 0.50 d P A 1 H1A H 0.2844 0.7283 0.6390 0.11(5) Uiso 0.50 calc PR A 1 Cl1A Cl 0.1149(3) 0.62693(9) 0.66901(11) 0.0606(4) Uani 0.50 d PR A 1 Cl2A Cl 0.1041(3) 0.76512(9) 0.74757(11) 0.1278(13) Uani 0.50 d PR A 1 Cl3A Cl 0.5008(3) 0.68852(9) 0.73651(11) 0.1282(11) Uani 0.50 d PR A 1 C1B C 0.2242(4) 0.71999(12) 0.68189(15) 0.0659(17) Uani 0.50 d P B 2 H1B H 0.2719 0.7347 0.6285 0.10(4) Uiso 0.50 calc PR B 2 Cl1B Cl 0.1343(4) 0.63511(12) 0.67801(15) 0.1193(14) Uani 0.50 d PR B 2 Cl2B Cl 0.0079(4) 0.77088(12) 0.71090(15) 0.1056(8) Uani 0.50 d PR B 2 Cl3B Cl 0.4323(4) 0.72579(12) 0.74873(15) 0.1587(17) Uani 0.50 d PR 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 I1 0.06292(10) 0.03971(8) 0.04067(8) -0.00548(4) 0.01095(6) -0.00119(5) C1 0.0402(8) 0.0276(7) 0.0347(7) -0.0043(6) -0.0015(6) 0.0065(6) C2 0.0396(8) 0.0280(7) 0.0354(7) -0.0040(6) 0.0000(6) 0.0042(6) C3 0.0403(8) 0.0265(6) 0.0356(7) -0.0030(6) -0.0010(6) 0.0042(6) C4 0.0398(8) 0.0331(7) 0.0399(8) -0.0033(6) -0.0034(6) 0.0057(6) C5 0.0491(9) 0.0405(9) 0.0344(8) -0.0019(6) -0.0056(7) 0.0022(7) C6 0.0503(9) 0.0354(8) 0.0372(8) -0.0048(6) 0.0028(7) 0.0010(7) C7 0.0421(9) 0.0343(8) 0.0435(9) -0.0040(7) 0.0011(7) 0.0068(7) C8 0.0422(8) 0.0337(7) 0.0369(8) -0.0033(6) -0.0055(6) 0.0069(6) C9 0.0429(8) 0.0266(7) 0.0360(8) -0.0021(6) 0.0018(6) 0.0034(6) C10 0.0566(11) 0.0331(9) 0.0752(15) -0.0102(9) -0.0244(11) 0.0053(8) C11 0.0559(12) 0.0337(9) 0.0833(16) -0.0075(9) -0.0243(11) 0.0115(8) C12 0.0475(9) 0.0274(7) 0.0359(8) -0.0005(6) 0.0064(6) 0.0019(6) C13 0.0572(11) 0.0337(9) 0.0626(12) -0.0105(8) -0.0164(9) 0.0025(8) C14 0.0519(10) 0.0333(8) 0.0613(12) -0.0076(8) -0.0175(9) 0.0069(7) N1 0.0515(8) 0.0274(6) 0.0486(8) -0.0030(6) 0.0072(7) 0.0032(6) C15 0.0987(19) 0.0386(10) 0.0571(13) -0.0105(10) -0.0012(12) -0.0007(11) C16 0.0586(13) 0.0388(11) 0.114(2) -0.0050(12) 0.0175(14) 0.0118(9) F1 0.0466(6) 0.0589(7) 0.0496(6) -0.0044(5) -0.0083(5) 0.0197(5) F2 0.0690(8) 0.0784(9) 0.0374(6) -0.0023(6) -0.0125(5) 0.0169(7) F3 0.0478(6) 0.0601(7) 0.0561(7) -0.0068(5) 0.0026(5) 0.0199(5) F4 0.0546(6) 0.0608(7) 0.0409(6) -0.0057(5) -0.0108(5) 0.0223(6) C1A 0.083(4) 0.048(3) 0.063(3) 0.015(2) 0.023(3) 0.002(3) Cl1A 0.0675(9) 0.0488(7) 0.0658(9) -0.0090(7) 0.0088(7) -0.0100(6) Cl2A 0.171(3) 0.0496(9) 0.166(3) -0.0193(13) 0.094(2) -0.0150(13) Cl3A 0.0905(14) 0.188(3) 0.1053(17) 0.0041(19) -0.0234(12) -0.0222(18) C1B 0.083(4) 0.045(3) 0.069(4) 0.017(3) 0.005(3) -0.015(3) Cl1B 0.163(3) 0.0799(16) 0.116(2) -0.0387(15) 0.036(2) -0.0396(17) Cl2B 0.1126(17) 0.0736(11) 0.132(2) -0.0006(12) 0.0401(15) -0.0094(11) Cl3B 0.146(3) 0.140(3) 0.187(3) 0.047(2) -0.084(3) -0.053(2) _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 I1 C6 2.0918(18) . ? C1 C3 1.500(2) . ? C1 C2 1.555(2) . ? C1 C2 1.585(2) 3 ? C1 H1 1.00(2) . ? C2 C9 1.514(2) . ? C2 C1 1.585(2) 3 ? C2 H2 0.98(2) . ? C3 C8 1.390(2) . ? C3 C4 1.391(2) . ? C4 F1 1.349(2) . ? C4 C5 1.375(3) . ? C5 F2 1.345(2) . ? C5 C6 1.382(3) . ? C6 C7 1.383(3) . ? C7 F3 1.345(2) . ? C7 C8 1.377(2) . ? C8 F4 1.3543(19) . ? C9 C10 1.377(3) . ? C9 C14 1.381(2) . ? C10 C11 1.395(3) . ? C10 H10 0.902(19) . ? C11 C12 1.381(3) . ? C11 H11 0.917(19) . ? C12 C13 1.386(3) . ? C12 N1 1.410(2) . ? C13 C14 1.389(3) . ? C13 H13 0.911(18) . ? C14 H14 0.919(18) . ? N1 C15 1.462(3) . ? N1 C16 1.464(3) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C1A Cl3A 1.7202 . ? C1A Cl2A 1.7535 . ? C1A Cl1A 1.7598 . ? C1A H1A 0.9800 . ? C1B Cl3B 1.6891 . ? C1B Cl1B 1.7063 . ? C1B Cl2B 1.7251 . ? C1B H1B 0.9800 . ? 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 C3 C1 C2 117.75(14) . . ? C3 C1 C2 120.03(13) . 3 ? C2 C1 C2 90.34(12) . 3 ? C3 C1 H1 109.6(12) . . ? C2 C1 H1 110.8(12) . . ? C2 C1 H1 106.8(12) 3 . ? C9 C2 C1 119.96(13) . . ? C9 C2 C1 120.82(14) . 3 ? C1 C2 C1 89.66(12) . 3 ? C9 C2 H2 105.5(12) . . ? C1 C2 H2 111.6(12) . . ? C1 C2 H2 108.6(12) 3 . ? C8 C3 C4 114.46(15) . . ? C8 C3 C1 123.93(15) . . ? C4 C3 C1 121.59(14) . . ? F1 C4 C5 117.65(15) . . ? F1 C4 C3 119.33(15) . . ? C5 C4 C3 123.01(16) . . ? F2 C5 C4 118.48(17) . . ? F2 C5 C6 119.99(17) . . ? C4 C5 C6 121.53(16) . . ? C5 C6 C7 116.53(16) . . ? C5 C6 I1 122.49(13) . . ? C7 C6 I1 120.95(14) . . ? F3 C7 C8 118.71(16) . . ? F3 C7 C6 119.91(17) . . ? C8 C7 C6 121.38(16) . . ? F4 C8 C7 117.39(15) . . ? F4 C8 C3 119.54(15) . . ? C7 C8 C3 123.06(16) . . ? C10 C9 C14 116.32(16) . . ? C10 C9 C2 124.96(15) . . ? C14 C9 C2 118.69(15) . . ? C9 C10 C11 121.99(18) . . ? C9 C10 H10 118.8(19) . . ? C11 C10 H10 119.1(19) . . ? C12 C11 C10 121.44(18) . . ? C12 C11 H11 121(2) . . ? C10 C11 H11 117(2) . . ? C11 C12 C13 116.75(16) . . ? C11 C12 N1 121.46(17) . . ? C13 C12 N1 121.68(17) . . ? C12 C13 C14 121.26(18) . . ? C12 C13 H13 119.8(18) . . ? C14 C13 H13 118.9(18) . . ? C9 C14 C13 122.22(18) . . ? C9 C14 H14 118.8(19) . . ? C13 C14 H14 119.0(19) . . ? C12 N1 C15 117.36(17) . . ? C12 N1 C16 116.95(17) . . ? C15 N1 C16 113.3(2) . . ? N1 C15 H15A 109.5 . . ? N1 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? N1 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N1 C16 H16A 109.5 . . ? N1 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? N1 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? Cl3A C1A Cl2A 110.9 . . ? Cl3A C1A Cl1A 111.1 . . ? Cl2A C1A Cl1A 113.2 . . ? Cl3A C1A H1A 107.1 . . ? Cl2A C1A H1A 107.1 . . ? Cl1A C1A H1A 107.1 . . ? Cl3B C1B Cl1B 109.3 . . ? Cl3B C1B Cl2B 111.4 . . ? Cl1B C1B Cl2B 106.7 . . ? Cl3B C1B H1B 109.8 . . ? Cl1B C1B H1B 109.8 . . ? Cl2B C1B H1B 109.8 . . ? 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 C3 C1 C2 C9 -109.33(17) . . . . ? C2 C1 C2 C9 126.02(18) 3 . . . ? C3 C1 C2 C1 124.65(16) . . . 3 ? C2 C1 C2 C1 0.0 3 . . 3 ? C2 C1 C3 C8 -49.3(2) . . . . ? C2 C1 C3 C8 58.9(2) 3 . . . ? C2 C1 C3 C4 129.41(17) . . . . ? C2 C1 C3 C4 -122.42(18) 3 . . . ? C8 C3 C4 F1 177.83(16) . . . . ? C1 C3 C4 F1 -1.0(3) . . . . ? C8 C3 C4 C5 -1.2(3) . . . . ? C1 C3 C4 C5 179.97(17) . . . . ? F1 C4 C5 F2 0.4(3) . . . . ? C3 C4 C5 F2 179.44(17) . . . . ? F1 C4 C5 C6 -179.09(17) . . . . ? C3 C4 C5 C6 0.0(3) . . . . ? F2 C5 C6 C7 -178.78(17) . . . . ? C4 C5 C6 C7 0.7(3) . . . . ? F2 C5 C6 I1 3.3(3) . . . . ? C4 C5 C6 I1 -177.26(14) . . . . ? C5 C6 C7 F3 -179.41(17) . . . . ? I1 C6 C7 F3 -1.5(3) . . . . ? C5 C6 C7 C8 0.0(3) . . . . ? I1 C6 C7 C8 177.95(14) . . . . ? F3 C7 C8 F4 -3.4(3) . . . . ? C6 C7 C8 F4 177.21(17) . . . . ? F3 C7 C8 C3 178.05(17) . . . . ? C6 C7 C8 C3 -1.4(3) . . . . ? C4 C3 C8 F4 -176.63(16) . . . . ? C1 C3 C8 F4 2.1(3) . . . . ? C4 C3 C8 C7 1.9(3) . . . . ? C1 C3 C8 C7 -179.34(17) . . . . ? C1 C2 C9 C10 -7.4(3) . . . . ? C1 C2 C9 C10 102.2(2) 3 . . . ? C1 C2 C9 C14 170.47(18) . . . . ? C1 C2 C9 C14 -79.9(2) 3 . . . ? C14 C9 C10 C11 0.8(4) . . . . ? C2 C9 C10 C11 178.8(2) . . . . ? C9 C10 C11 C12 0.3(4) . . . . ? C10 C11 C12 C13 -1.3(4) . . . . ? C10 C11 C12 N1 -177.6(2) . . . . ? C11 C12 C13 C14 1.3(3) . . . . ? N1 C12 C13 C14 177.5(2) . . . . ? C10 C9 C14 C13 -0.9(3) . . . . ? C2 C9 C14 C13 -179.0(2) . . . . ? C12 C13 C14 C9 -0.2(4) . . . . ? C11 C12 N1 C15 -166.2(2) . . . . ? C13 C12 N1 C15 17.8(3) . . . . ? C11 C12 N1 C16 -26.5(3) . . . . ? C13 C12 N1 C16 157.4(2) . . . . ? _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 30.59 _diffrn_measured_fraction_theta_full 0.972 _refine_diff_density_max 0.668 _refine_diff_density_min -0.471 _refine_diff_density_rms 0.081 data_re142 _database_code_depnum_ccdc_archive 'CCDC 604218' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C16 H12 F4 I N' _chemical_formula_sum 'C16 H12 F4 I N' _chemical_formula_weight 421.17 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-P 2ybc' 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 10.174(2) _cell_length_b 11.671(2) _cell_length_c 13.043(4) _cell_angle_alpha 90.00 _cell_angle_beta 103.26(3) _cell_angle_gamma 90.00 _cell_volume 1507.4(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6324 _cell_measurement_theta_min 2.371 _cell_measurement_theta_max 30.574 _exptl_crystal_description prism _exptl_crystal_colour orange-yellow _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.14 _exptl_crystal_density_diffrn 1.856 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 2.162 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.416301 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details ; SADABS - Bruker/Siemens area detector absorption and other corrections - V2.03 ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD area detector' _diffrn_measurement_method '\w and \f scans' _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 28489 _diffrn_reflns_av_R_equivalents 0.0297 _diffrn_reflns_av_sigmaI/netI 0.0316 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 30.67 _reflns_number_total 4649 _reflns_number_gt 3733 _reflns_threshold_expression >2s\(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SIR-92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPIII (Burnett & Johnson,1996)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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. H atoms were refined with some restraints (SADI routine of SHELX-97) ; _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^)+(0.0699P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 4649 _refine_ls_number_parameters 217 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.0423 _refine_ls_R_factor_gt 0.0361 _refine_ls_wR_factor_ref 0.1048 _refine_ls_wR_factor_gt 0.0996 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.791357(16) 0.589776(12) 0.670903(13) 0.05796(8) Uani 1 d . . . C7 C 0.4312(2) 0.1639(2) 0.46540(19) 0.0553(5) Uani 1 d D . . H7 H 0.447(3) 0.134(3) 0.403(2) 0.066 Uiso 1 d D . . C8 C 0.3498(3) 0.09897(19) 0.5073(2) 0.0531(5) Uani 1 d D . . H8 H 0.349(3) 0.102(2) 0.576(2) 0.064 Uiso 1 d D . . C6 C 0.5089(2) 0.26205(18) 0.51746(17) 0.0490(4) Uani 1 d . . . C1 C 0.4988(2) 0.3144(2) 0.61160(18) 0.0533(5) Uani 1 d . . . C2 C 0.5755(3) 0.40737(18) 0.65308(19) 0.0516(5) Uani 1 d . . . C3 C 0.6675(2) 0.45445(18) 0.60298(16) 0.0485(4) Uani 1 d . . . C4 C 0.6789(3) 0.40479(19) 0.5100(2) 0.0556(5) Uani 1 d . . . C5 C 0.6017(2) 0.3116(2) 0.46865(17) 0.0567(5) Uani 1 d . . . F1 F 0.41084(18) 0.27416(16) 0.66606(13) 0.0812(5) Uani 1 d . . . F2 F 0.5593(2) 0.45186(16) 0.74410(14) 0.0795(5) Uani 1 d . . . F3 F 0.7663(2) 0.44808(18) 0.45596(14) 0.0875(5) Uani 1 d . . . F4 F 0.6195(2) 0.26966(17) 0.37676(13) 0.0852(5) Uani 1 d . . . C9 C 0.2684(2) 0.00402(18) 0.44713(17) 0.0510(4) Uani 1 d . . . C10 C 0.1737(3) -0.0478(2) 0.49189(19) 0.0591(5) Uani 1 d D . . H10 H 0.177(3) -0.027(3) 0.5596(16) 0.071 Uiso 1 d D . . C11 C 0.0903(3) -0.1334(2) 0.44252(17) 0.0560(5) Uani 1 d D . . H11 H 0.039(3) -0.174(2) 0.4781(19) 0.067 Uiso 1 d D . . C12 C 0.0987(2) -0.17438(17) 0.34364(14) 0.0442(4) Uani 1 d . . . C13 C 0.1970(2) -0.1256(2) 0.29802(18) 0.0513(4) Uani 1 d D . . H13 H 0.202(3) -0.154(2) 0.2343(15) 0.062 Uiso 1 d D . . C14 C 0.2791(2) -0.0381(2) 0.34922(19) 0.0550(5) Uani 1 d D . . H14 H 0.338(3) -0.016(2) 0.313(2) 0.066 Uiso 1 d D . . N1 N 0.0085(2) -0.25646(17) 0.29209(15) 0.0568(4) Uani 1 d . . . C15 C -0.0672(3) -0.3247(3) 0.3520(2) 0.0707(7) Uani 1 d . . . H15A H -0.1248 -0.3772 0.3057 0.106 Uiso 1 calc R . . H15B H -0.1212 -0.2751 0.3844 0.106 Uiso 1 calc R . . H15C H -0.0055 -0.3668 0.4056 0.106 Uiso 1 calc R . . C16 C 0.0375(3) -0.3099(2) 0.19890(19) 0.0670(6) Uani 1 d . . . H16A H -0.0318 -0.3646 0.1707 0.100 Uiso 1 calc R . . H16B H 0.1232 -0.3480 0.2176 0.100 Uiso 1 calc R . . H16C H 0.0401 -0.2522 0.1469 0.100 Uiso 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 I1 0.06053(12) 0.04083(11) 0.06876(13) -0.00026(5) 0.00711(8) -0.00692(5) C7 0.0599(12) 0.0456(11) 0.0584(12) -0.0004(9) 0.0092(10) -0.0033(9) C8 0.0614(13) 0.0482(12) 0.0517(11) 0.0004(8) 0.0170(10) -0.0030(9) C6 0.0484(10) 0.0400(9) 0.0541(10) 0.0020(8) 0.0024(8) 0.0001(8) C1 0.0504(10) 0.0501(11) 0.0601(11) 0.0043(9) 0.0142(9) -0.0056(9) C2 0.0545(12) 0.0500(12) 0.0512(11) -0.0039(8) 0.0140(9) -0.0003(8) C3 0.0503(10) 0.0419(10) 0.0511(10) 0.0021(8) 0.0073(8) -0.0001(8) C4 0.0582(13) 0.0542(13) 0.0557(12) 0.0013(9) 0.0160(10) -0.0090(9) C5 0.0639(13) 0.0553(13) 0.0514(11) -0.0058(9) 0.0143(10) -0.0073(10) F1 0.0852(11) 0.0863(12) 0.0824(10) -0.0131(8) 0.0406(9) -0.0345(9) F2 0.0937(12) 0.0802(10) 0.0755(10) -0.0251(9) 0.0421(9) -0.0247(9) F3 0.1005(13) 0.0992(12) 0.0746(10) -0.0164(9) 0.0441(10) -0.0438(11) F4 0.1025(13) 0.0937(12) 0.0678(9) -0.0282(8) 0.0370(9) -0.0323(10) C9 0.0521(10) 0.0415(10) 0.0558(11) 0.0035(8) 0.0052(8) 0.0023(8) C10 0.0757(15) 0.0522(13) 0.0496(11) -0.0093(10) 0.0147(10) -0.0083(11) C11 0.0702(14) 0.0561(13) 0.0450(10) -0.0054(9) 0.0202(9) -0.0151(11) C12 0.0509(10) 0.0395(9) 0.0420(8) 0.0015(7) 0.0103(7) 0.0007(7) C13 0.0547(11) 0.0549(12) 0.0475(9) 0.0008(10) 0.0182(8) 0.0022(9) C14 0.0490(11) 0.0541(13) 0.0661(13) 0.0105(10) 0.0222(10) -0.0011(9) N1 0.0654(11) 0.0528(11) 0.0527(9) -0.0102(8) 0.0145(8) -0.0123(8) C15 0.0740(16) 0.0597(15) 0.0791(17) -0.0028(13) 0.0188(13) -0.0176(13) C16 0.0836(17) 0.0561(14) 0.0571(13) -0.0172(11) 0.0075(12) 0.0082(12) _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 I1 C3 2.087(2) . ? C7 C8 1.330(3) . ? C7 C6 1.466(3) . ? C7 H7 0.93(2) . ? C8 C9 1.494(3) . ? C8 H8 0.90(2) . ? C6 C5 1.382(3) . ? C6 C1 1.396(3) . ? C1 F1 1.349(3) . ? C1 C2 1.373(3) . ? C2 F2 1.340(3) . ? C2 C3 1.373(3) . ? C3 C4 1.373(3) . ? C4 F3 1.353(3) . ? C4 C5 1.377(3) . ? C5 F4 1.345(3) . ? C9 C10 1.375(3) . ? C9 C14 1.396(3) . ? C10 C11 1.372(3) . ? C10 H10 0.911(19) . ? C11 C12 1.396(3) . ? C11 H11 0.906(19) . ? C12 N1 1.389(3) . ? C12 C13 1.397(3) . ? C13 C14 1.390(4) . ? C13 H13 0.904(18) . ? C14 H14 0.885(18) . ? N1 C15 1.454(3) . ? N1 C16 1.455(3) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? 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 C8 C7 C6 125.1(2) . . ? C8 C7 H7 113.3(19) . . ? C6 C7 H7 120.8(19) . . ? C7 C8 C9 122.0(2) . . ? C7 C8 H8 122.0(19) . . ? C9 C8 H8 115.4(18) . . ? C5 C6 C1 114.69(19) . . ? C5 C6 C7 117.8(2) . . ? C1 C6 C7 127.5(2) . . ? F1 C1 C2 117.0(2) . . ? F1 C1 C6 120.1(2) . . ? C2 C1 C6 122.9(2) . . ? F2 C2 C1 118.8(2) . . ? F2 C2 C3 120.1(2) . . ? C1 C2 C3 121.1(2) . . ? C2 C3 C4 117.2(2) . . ? C2 C3 I1 120.80(16) . . ? C4 C3 I1 121.93(16) . . ? F3 C4 C3 120.1(2) . . ? F3 C4 C5 118.3(2) . . ? C3 C4 C5 121.5(2) . . ? F4 C5 C4 117.1(2) . . ? F4 C5 C6 120.3(2) . . ? C4 C5 C6 122.6(2) . . ? C10 C9 C14 116.3(2) . . ? C10 C9 C8 117.5(2) . . ? C14 C9 C8 126.3(2) . . ? C11 C10 C9 122.6(2) . . ? C11 C10 H10 122(2) . . ? C9 C10 H10 115(2) . . ? C10 C11 C12 121.4(2) . . ? C10 C11 H11 120.4(18) . . ? C12 C11 H11 117.3(18) . . ? N1 C12 C11 120.65(19) . . ? N1 C12 C13 122.21(19) . . ? C11 C12 C13 117.1(2) . . ? C14 C13 C12 120.3(2) . . ? C14 C13 H13 123.7(18) . . ? C12 C13 H13 115.9(18) . . ? C13 C14 C9 122.3(2) . . ? C13 C14 H14 111.3(19) . . ? C9 C14 H14 126.5(19) . . ? C12 N1 C15 119.34(19) . . ? C12 N1 C16 117.5(2) . . ? C15 N1 C16 116.6(2) . . ? N1 C15 H15A 109.5 . . ? N1 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? N1 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N1 C16 H16A 109.5 . . ? N1 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? N1 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? 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 C6 C7 C8 C9 176.8(2) . . . . ? C8 C7 C6 C5 172.0(2) . . . . ? C8 C7 C6 C1 -9.3(4) . . . . ? C5 C6 C1 F1 179.5(2) . . . . ? C7 C6 C1 F1 0.8(4) . . . . ? C5 C6 C1 C2 -0.4(3) . . . . ? C7 C6 C1 C2 -179.1(2) . . . . ? F1 C1 C2 F2 0.3(3) . . . . ? C6 C1 C2 F2 -179.8(2) . . . . ? F1 C1 C2 C3 -179.8(2) . . . . ? C6 C1 C2 C3 0.1(4) . . . . ? F2 C2 C3 C4 -180.0(2) . . . . ? C1 C2 C3 C4 0.1(3) . . . . ? F2 C2 C3 I1 3.4(3) . . . . ? C1 C2 C3 I1 -176.46(17) . . . . ? C2 C3 C4 F3 179.1(2) . . . . ? I1 C3 C4 F3 -4.4(3) . . . . ? C2 C3 C4 C5 -0.1(4) . . . . ? I1 C3 C4 C5 176.5(2) . . . . ? F3 C4 C5 F4 0.3(4) . . . . ? C3 C4 C5 F4 179.4(2) . . . . ? F3 C4 C5 C6 -179.4(2) . . . . ? C3 C4 C5 C6 -0.2(4) . . . . ? C1 C6 C5 F4 -179.2(2) . . . . ? C7 C6 C5 F4 -0.4(3) . . . . ? C1 C6 C5 C4 0.4(4) . . . . ? C7 C6 C5 C4 179.3(2) . . . . ? C7 C8 C9 C10 -171.3(2) . . . . ? C7 C8 C9 C14 8.9(4) . . . . ? C14 C9 C10 C11 -2.3(4) . . . . ? C8 C9 C10 C11 177.9(3) . . . . ? C9 C10 C11 C12 1.1(4) . . . . ? C10 C11 C12 N1 -176.3(2) . . . . ? C10 C11 C12 C13 1.0(4) . . . . ? N1 C12 C13 C14 175.6(2) . . . . ? C11 C12 C13 C14 -1.7(3) . . . . ? C12 C13 C14 C9 0.4(4) . . . . ? C10 C9 C14 C13 1.5(3) . . . . ? C8 C9 C14 C13 -178.7(2) . . . . ? C11 C12 N1 C15 -18.6(3) . . . . ? C13 C12 N1 C15 164.3(2) . . . . ? C11 C12 N1 C16 -169.3(2) . . . . ? C13 C12 N1 C16 13.6(3) . . . . ? _diffrn_measured_fraction_theta_max 0.952 _diffrn_reflns_theta_full 30.67 _diffrn_measured_fraction_theta_full 0.952 _refine_diff_density_max 0.934 _refine_diff_density_min -1.299 _refine_diff_density_rms 0.093 _chemical_name_common ;dimethyl-(4-(2-(2,3,5,6-tetrafluoro-4-iodo-phenyl)-vinyl)- phenyl)-amine ;