# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Kazuki Sada' _publ_contact_author_address ; Department of Chemistry and Biochemistry Kyushu University Graduate School of Engineering 744 Motooka, Nishi-ku Fukuoka 819-0395 JAPAN ; _publ_contact_author_email SADATCM@MBOX.NC.KYUSHU-U.AC.JP _publ_section_title ; Face-Selective Decoration of an Organic Single Crystal toward Photochemical Devices ; loop_ _publ_author_name 'Kazuki Sada' 'Yuzo Fujiki' S.Shinkai 'Nami Tokunaga' data_fujiki1 _database_code_depnum_ccdc_archive 'CCDC 606956' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H14 Cl N' _chemical_formula_weight 267.74 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_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' _cell_length_a 4.8026(15) _cell_length_b 7.891(3) _cell_length_c 35.162(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1332.6(7) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2925 _cell_measurement_theta_min 2.32 _cell_measurement_theta_max 25.52 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.75 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.335 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 560 _exptl_absorpt_coefficient_mu 0.271 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8227 _exptl_absorpt_correction_T_max 0.9839 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.366 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10531 _diffrn_reflns_av_R_equivalents 0.0323 _diffrn_reflns_av_sigmaI/netI 0.0413 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 49 _diffrn_reflns_theta_min 1.16 _diffrn_reflns_theta_max 30.37 _reflns_number_total 3736 _reflns_number_gt 2732 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0884P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.05(10) _refine_ls_number_reflns 3736 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0871 _refine_ls_R_factor_gt 0.0629 _refine_ls_wR_factor_ref 0.1606 _refine_ls_wR_factor_gt 0.1427 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.072 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.68641(16) 0.80894(9) 0.779552(19) 0.0535(2) Uani 1 1 d . . . C2 C 0.1285(5) 0.2159(3) 0.85941(7) 0.0383(5) Uani 1 1 d . . . C17 C -0.1662(6) 0.2917(3) 0.80293(7) 0.0447(6) Uani 1 1 d . . . H17A H -0.1243 0.1807 0.7925 0.054 Uiso 1 1 calc R . . H17B H -0.3446 0.2840 0.8157 0.054 Uiso 1 1 calc R . . C15 C 0.3294(5) 0.2567(3) 0.88750(7) 0.0397(5) Uani 1 1 d . . . C16 C 0.4049(6) 0.1356(3) 0.91555(7) 0.0439(6) Uani 1 1 d . . . C1 C 0.0550(5) 0.3365(3) 0.83202(7) 0.0388(5) Uani 1 1 d . . . C13 C 0.3782(6) 0.5357(3) 0.86003(8) 0.0509(7) Uani 1 1 d . . . H13 H 0.4607 0.6423 0.8597 0.061 Uiso 1 1 calc R . . C14 C 0.1816(6) 0.4960(3) 0.83282(8) 0.0467(6) Uani 1 1 d . . . H14 H 0.1326 0.5766 0.8147 0.056 Uiso 1 1 calc R . . C3 C 0.0067(6) 0.0490(3) 0.86031(8) 0.0457(6) Uani 1 1 d . . . H3 H -0.1250 0.0193 0.8421 0.055 Uiso 1 1 calc R . . C5 C 0.2825(7) -0.0279(4) 0.91536(8) 0.0515(7) Uani 1 1 d . . . C11 C 0.6554(7) 0.4574(4) 0.91665(9) 0.0579(8) Uani 1 1 d . . . H11 H 0.7375 0.5641 0.9173 0.070 Uiso 1 1 calc R . . C9 C 0.6077(6) 0.1775(4) 0.94356(8) 0.0553(8) Uani 1 1 d . . . C12 C 0.4552(6) 0.4203(4) 0.88774(7) 0.0443(6) Uani 1 1 d . . . C4 C 0.0795(7) -0.0641(4) 0.88683(8) 0.0539(7) Uani 1 1 d . . . H4 H -0.0052 -0.1701 0.8867 0.065 Uiso 1 1 calc R . . C10 C 0.7282(7) 0.3411(5) 0.94302(9) 0.0658(9) Uani 1 1 d . . . H10 H 0.8607 0.3692 0.9613 0.079 Uiso 1 1 calc R . . C6 C 0.3634(8) -0.1445(4) 0.94264(9) 0.0690(10) Uani 1 1 d . . . H6 H 0.2828 -0.2517 0.9429 0.083 Uiso 1 1 calc R . . C7 C 0.5616(9) -0.1040(6) 0.96946(10) 0.0777(11) Uani 1 1 d . . . H7 H 0.6145 -0.1851 0.9872 0.093 Uiso 1 1 calc R . . C8 C 0.6822(9) 0.0525(6) 0.97050(8) 0.0712(10) Uani 1 1 d . . . H8 H 0.8141 0.0771 0.9891 0.085 Uiso 1 1 calc R . . N1 N -0.1908(5) 0.4139(3) 0.77121(6) 0.0514(6) Uani 1 1 d . . . H1A H -0.0395 0.4079 0.7567 0.077 Uiso 1 1 calc R . . H1B H -0.2074 0.5183 0.7805 0.077 Uiso 1 1 calc R . . H1C H -0.3404 0.3890 0.7574 0.077 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0543(4) 0.0513(3) 0.0551(4) 0.0026(3) -0.0091(3) 0.0014(3) C2 0.0346(12) 0.0401(12) 0.0401(12) -0.0059(10) 0.0017(9) 0.0021(10) C17 0.0459(14) 0.0426(13) 0.0455(13) -0.0009(10) -0.0071(12) 0.0012(13) C15 0.0336(12) 0.0466(13) 0.0391(12) -0.0091(10) 0.0031(10) 0.0060(11) C16 0.0407(14) 0.0545(14) 0.0367(12) -0.0044(11) 0.0058(10) 0.0098(11) C1 0.0357(13) 0.0399(12) 0.0408(12) -0.0070(10) 0.0007(10) 0.0020(10) C13 0.0498(16) 0.0407(13) 0.0623(17) -0.0080(12) -0.0029(13) -0.0082(12) C14 0.0473(14) 0.0415(12) 0.0512(14) 0.0031(11) -0.0053(14) 0.0013(13) C3 0.0470(15) 0.0392(13) 0.0509(15) -0.0043(12) -0.0041(12) -0.0016(11) C5 0.0527(17) 0.0586(16) 0.0431(13) 0.0069(12) 0.0103(13) 0.0141(14) C11 0.0481(17) 0.0628(17) 0.0629(17) -0.0206(15) -0.0078(15) -0.0018(15) C9 0.0462(16) 0.079(2) 0.0402(13) -0.0068(14) -0.0002(12) 0.0162(15) C12 0.0370(13) 0.0509(14) 0.0451(14) -0.0105(12) 0.0011(12) 0.0002(12) C4 0.0585(18) 0.0454(14) 0.0577(16) 0.0034(13) 0.0070(15) -0.0027(14) C10 0.0514(19) 0.096(3) 0.0494(16) -0.0217(17) -0.0078(14) 0.0048(17) C6 0.076(2) 0.073(2) 0.0584(18) 0.0205(16) 0.0147(17) 0.0216(18) C7 0.084(3) 0.095(3) 0.0541(19) 0.0224(19) 0.0030(19) 0.032(2) C8 0.065(2) 0.108(3) 0.0406(15) 0.0027(17) 0.0015(16) 0.029(2) N1 0.0492(13) 0.0500(12) 0.0548(13) -0.0008(10) -0.0138(12) 0.0038(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 C2 C1 1.400(3) . ? C2 C15 1.418(4) . ? C2 C3 1.441(4) . ? C17 N1 1.479(3) . ? C17 C1 1.516(4) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C15 C16 1.421(4) . ? C15 C12 1.425(4) . ? C16 C5 1.418(4) . ? C16 C9 1.424(4) . ? C1 C14 1.398(4) . ? C13 C14 1.380(4) . ? C13 C12 1.384(4) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C3 C4 1.337(4) . ? C3 H3 0.9300 . ? C5 C6 1.385(4) . ? C5 C4 1.427(5) . ? C11 C10 1.351(5) . ? C11 C12 1.429(4) . ? C11 H11 0.9300 . ? C9 C8 1.414(5) . ? C9 C10 1.414(5) . ? C4 H4 0.9300 . ? C10 H10 0.9300 . ? C6 C7 1.378(6) . ? C6 H6 0.9300 . ? C7 C8 1.364(6) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? N1 H1A 0.8900 . ? N1 H1B 0.8900 . ? N1 H1C 0.8900 . ? 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 C15 119.7(2) . . ? C1 C2 C3 122.3(2) . . ? C15 C2 C3 118.0(2) . . ? N1 C17 C1 114.4(2) . . ? N1 C17 H17A 108.7 . . ? C1 C17 H17A 108.7 . . ? N1 C17 H17B 108.7 . . ? C1 C17 H17B 108.7 . . ? H17A C17 H17B 107.6 . . ? C2 C15 C16 120.3(2) . . ? C2 C15 C12 119.9(2) . . ? C16 C15 C12 119.8(2) . . ? C5 C16 C15 120.2(2) . . ? C5 C16 C9 119.9(3) . . ? C15 C16 C9 119.9(3) . . ? C14 C1 C2 119.3(2) . . ? C14 C1 C17 121.9(2) . . ? C2 C1 C17 118.8(2) . . ? C14 C13 C12 121.5(3) . . ? C14 C13 H13 119.3 . . ? C12 C13 H13 119.3 . . ? C13 C14 C1 121.0(2) . . ? C13 C14 H14 119.5 . . ? C1 C14 H14 119.5 . . ? C4 C3 C2 121.2(3) . . ? C4 C3 H3 119.4 . . ? C2 C3 H3 119.4 . . ? C6 C5 C16 119.0(3) . . ? C6 C5 C4 123.1(3) . . ? C16 C5 C4 117.9(2) . . ? C10 C11 C12 121.6(3) . . ? C10 C11 H11 119.2 . . ? C12 C11 H11 119.2 . . ? C8 C9 C10 122.8(3) . . ? C8 C9 C16 118.3(3) . . ? C10 C9 C16 118.9(3) . . ? C13 C12 C15 118.6(2) . . ? C13 C12 C11 123.1(3) . . ? C15 C12 C11 118.3(3) . . ? C3 C4 C5 122.4(3) . . ? C3 C4 H4 118.8 . . ? C5 C4 H4 118.8 . . ? C11 C10 C9 121.6(3) . . ? C11 C10 H10 119.2 . . ? C9 C10 H10 119.2 . . ? C7 C6 C5 120.9(4) . . ? C7 C6 H6 119.5 . . ? C5 C6 H6 119.5 . . ? C8 C7 C6 121.5(3) . . ? C8 C7 H7 119.3 . . ? C6 C7 H7 119.3 . . ? C7 C8 C9 120.4(3) . . ? C7 C8 H8 119.8 . . ? C9 C8 H8 119.8 . . ? C17 N1 H1A 109.5 . . ? C17 N1 H1B 109.5 . . ? H1A N1 H1B 109.5 . . ? C17 N1 H1C 109.5 . . ? H1A N1 H1C 109.5 . . ? H1B N1 H1C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.950 _diffrn_reflns_theta_full 30.37 _diffrn_measured_fraction_theta_full 0.950 _refine_diff_density_max 0.413 _refine_diff_density_min -0.240 _refine_diff_density_rms 0.067