# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name _publ_author_address F.Hof ;Department of Chemistry, University of Victoria PO Box 3065, Victoria, BC, V8W 3V6 (Canada) ; D.Mahnke ;Department of Chemistry, University of Victoria PO Box 3065, Victoria, BC, V8W 3V6 (Canada) ; R.McDonald ;Department of Chemistry, University of Alberta 11227 Saskatchewan Dr., Edmonton, AB, T6G 2G2 (Canada) ; _publ_contact_author_address ;Department of Chemistry, University of Victoria PO Box 3065, Victoria, BC, V8W 3V6 (Canada) ; _publ_contact_author_email fhof@uvic.ca _publ_contact_author_fax '1 250 721 7147' _publ_contact_author_phone '1 250 721 7193' _publ_contact_author_name 'Fraser Hof' _publ_requested_journal 'Chemical Communications' _publ_section_title ; A shape-dependent hydrophobic effect for tetrazoles in water ; data_vic0611 _database_code_depnum_ccdc_archive 'CCDC 637204' _audit_creation_method SHELXL-97 _chemical_name_systematic '1,3,5-tris(1H-tetrazol-5-yl)methyl-2,4,6-triethyl benzene' _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H24 N12, C H4 O, H2 O' _chemical_formula_sum 'C19 H30 N12 O2' _chemical_formula_weight 458.55 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'C m c 21' _symmetry_int_tables_number 36 _symmetry_space_group_name_Hall 'C 2c -2' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x, -y, z+1/2' '-x, y, z' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1/2, z' _cell_length_a 11.9746(7) _cell_length_b 18.4624(11) _cell_length_c 10.3004(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2277.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 7740 _cell_measurement_theta_min 2.21 _cell_measurement_theta_max 26.33 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.65 _exptl_crystal_size_mid 0.41 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.337 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 976 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9412 _exptl_absorpt_correction_T_max 0.9632 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(2) _diffrn_radiation_probe ? _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker PLATFORM diffractometer/SMART 1000 CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8.192 _diffrn_standards_number 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 8287 _diffrn_reflns_av_R_equivalents 0.0124 _diffrn_reflns_av_sigmaI/netI 0.0119 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 26.38 _reflns_number_total 2437 _reflns_number_gt 2386 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART (Bruker, 1997)' _computing_cell_refinement 'Bruker SAINT (Bruker, 1997)' _computing_data_reduction 'Bruker SAINT (Bruker, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL (Bruker, 1997)' _computing_publication_material 'Bruker SHELXTL (Bruker, 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. ; _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^)+(0.0425P)^2^+0.6614P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.3(10) _refine_ls_number_reflns 2437 _refine_ls_number_parameters 183 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0268 _refine_ls_R_factor_gt 0.0262 _refine_ls_wR_factor_ref 0.0709 _refine_ls_wR_factor_gt 0.0696 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _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 N11 N 0.0000 0.27083(8) 0.31550(16) 0.0280(3) Uani 1 2 d S . . H11N H 0.0000 0.2220(14) 0.296(3) 0.043(6) Uiso 1 2 d S . . N12 N 0.0000 0.28768(9) 0.44276(16) 0.0343(3) Uani 1 2 d S . . N13 N 0.0000 0.35776(9) 0.44922(16) 0.0346(4) Uani 1 2 d S . . N14 N 0.0000 0.38721(8) 0.32789(16) 0.0309(3) Uani 1 2 d S . . N21 N 0.31006(10) 0.01657(6) 0.00464(11) 0.0312(2) Uani 1 1 d . . . H21N H 0.3522(14) 0.0041(10) -0.0597(19) 0.042(4) Uiso 1 1 d . . . N22 N 0.31564(10) -0.01906(6) 0.11853(11) 0.0359(3) Uani 1 1 d . . . N23 N 0.24908(10) 0.01417(6) 0.19585(12) 0.0339(3) Uani 1 1 d . . . N24 N 0.19972(9) 0.07132(5) 0.13527(11) 0.0301(2) Uani 1 1 d . . . C1 C 0.0000 0.26472(8) 0.03470(16) 0.0225(3) Uani 1 2 d S . . C2 C 0.10210(9) 0.23090(5) 0.00603(11) 0.0221(2) Uani 1 1 d . . . C3 C 0.10131(9) 0.16408(6) -0.05898(11) 0.0219(2) Uani 1 1 d . . . C4 C 0.0000 0.13069(8) -0.09235(16) 0.0231(3) Uani 1 2 d S . . C5 C 0.21161(11) 0.26675(6) 0.04353(12) 0.0276(3) Uani 1 1 d . . . H5A H 0.2674 0.2288 0.0636 0.033 Uiso 1 1 calc R . . H5B H 0.2001 0.2959 0.1231 0.033 Uiso 1 1 calc R . . C6 C 0.25748(12) 0.31578(7) -0.06390(15) 0.0355(3) Uani 1 1 d . . . H6A H 0.3278 0.3377 -0.0351 0.043 Uiso 1 1 calc R . . H6B H 0.2032 0.3540 -0.0830 0.043 Uiso 1 1 calc R . . H6C H 0.2708 0.2870 -0.1423 0.043 Uiso 1 1 calc R . . C7 C 0.0000 0.06032(9) -0.16907(16) 0.0263(3) Uani 1 2 d S . . H7A H -0.0669 0.0316 -0.1459 0.032 Uiso 0.50 1 calc PR . . H7B H 0.0669 0.0316 -0.1459 0.032 Uiso 0.50 1 calc PR . . C8 C 0.0000 0.07497(11) -0.31526(19) 0.0374(4) Uani 1 2 d S . . H8A H 0.0000 0.0288 -0.3623 0.045 Uiso 1 2 calc SR . . H8B H 0.0668 0.1027 -0.3385 0.045 Uiso 0.50 1 calc PR . . H8C H -0.0668 0.1027 -0.3385 0.045 Uiso 0.50 1 calc PR . . C10 C 0.0000 0.33763(9) 0.10196(17) 0.0258(3) Uani 1 2 d S . . H10A H 0.0668 0.3652 0.0741 0.031 Uiso 0.50 1 calc PR . . H10B H -0.0668 0.3652 0.0741 0.031 Uiso 0.50 1 calc PR . . C11 C 0.0000 0.33203(9) 0.24702(18) 0.0255(3) Uani 1 2 d S . . C20 C 0.21049(10) 0.12548(6) -0.08844(12) 0.0245(2) Uani 1 1 d . . . H20A H 0.2042 0.1001 -0.1728 0.029 Uiso 1 1 calc R . . H20B H 0.2713 0.1616 -0.0956 0.029 Uiso 1 1 calc R . . C21 C 0.23891(9) 0.07179(6) 0.01568(11) 0.0239(2) Uani 1 1 d . . . O1S O 0.0000 0.53670(8) 0.35163(13) 0.0365(3) Uani 1 2 d S . . H1SO H 0.0000 0.499(2) 0.307(3) 0.067(9) Uiso 1 2 d S . . C1S C 0.0000 0.59664(12) 0.2631(2) 0.0433(5) Uani 1 2 d S . . H1SA H -0.0764 0.6058 0.2332 0.052 Uiso 0.50 1 calc PR . . H1SB H 0.0476 0.5853 0.1885 0.052 Uiso 0.50 1 calc PR . . H1SC H 0.0288 0.6398 0.3072 0.052 Uiso 0.50 1 calc PR . . O2S O 0.0000 0.12944(7) 0.26395(13) 0.0307(3) Uani 1 2 d S . . H2SO H 0.0617(15) 0.1116(9) 0.2196(17) 0.048(5) Uiso 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 N11 0.0279(7) 0.0274(7) 0.0286(7) -0.0028(6) 0.000 0.000 N12 0.0323(8) 0.0405(8) 0.0301(8) -0.0035(7) 0.000 0.000 N13 0.0316(8) 0.0400(8) 0.0323(8) -0.0080(7) 0.000 0.000 N14 0.0308(7) 0.0298(7) 0.0320(8) -0.0071(6) 0.000 0.000 N21 0.0358(5) 0.0276(5) 0.0302(6) 0.0025(4) 0.0071(5) 0.0077(4) N22 0.0410(6) 0.0299(5) 0.0367(6) 0.0066(4) 0.0038(5) 0.0072(5) N23 0.0356(6) 0.0335(6) 0.0327(6) 0.0066(5) 0.0013(4) 0.0048(5) N24 0.0306(5) 0.0303(5) 0.0294(5) 0.0039(4) 0.0027(4) 0.0072(4) C1 0.0258(8) 0.0200(7) 0.0218(8) 0.0016(6) 0.000 0.000 C2 0.0225(6) 0.0217(5) 0.0220(5) 0.0025(4) -0.0003(4) -0.0019(4) C3 0.0229(5) 0.0214(5) 0.0216(5) 0.0028(4) 0.0010(4) 0.0019(4) C4 0.0265(8) 0.0200(7) 0.0228(8) 0.0023(6) 0.000 0.000 C5 0.0240(5) 0.0267(6) 0.0320(6) -0.0025(5) -0.0015(5) -0.0006(4) C6 0.0300(6) 0.0318(6) 0.0447(7) -0.0006(6) 0.0063(5) -0.0072(5) C7 0.0255(8) 0.0241(7) 0.0294(9) -0.0050(7) 0.000 0.000 C8 0.0432(11) 0.0410(10) 0.0281(9) -0.0070(8) 0.000 0.000 C10 0.0277(8) 0.0208(7) 0.0288(8) -0.0022(6) 0.000 0.000 C11 0.0191(7) 0.0265(9) 0.0309(9) -0.0049(7) 0.000 0.000 C20 0.0238(5) 0.0237(5) 0.0258(5) 0.0001(5) 0.0020(4) 0.0010(4) C21 0.0210(5) 0.0217(5) 0.0291(6) -0.0013(4) 0.0003(5) -0.0001(4) O1S 0.0502(8) 0.0310(7) 0.0282(6) -0.0011(5) 0.000 0.000 C1S 0.0477(12) 0.0441(12) 0.0382(10) 0.0054(9) 0.000 0.000 O2S 0.0314(6) 0.0269(6) 0.0337(7) -0.0025(5) 0.000 0.000 _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 N11 C11 1.332(2) . ? N11 N12 1.347(2) . ? N12 N13 1.295(2) . ? N13 N14 1.363(2) . ? N14 C11 1.316(2) . ? N21 C21 1.3334(16) . ? N21 N22 1.3466(15) . ? N22 N23 1.2829(16) . ? N23 N24 1.3608(15) . ? N24 C21 1.3182(16) . ? C1 C2 1.4042(13) 4 ? C1 C2 1.4042(13) . ? C1 C10 1.514(2) . ? C2 C3 1.4038(15) . ? C2 C5 1.5188(16) . ? C3 C4 1.4035(13) . ? C3 C20 1.5196(15) . ? C4 C3 1.4035(13) 4 ? C4 C7 1.521(2) . ? C5 C6 1.5316(18) . ? C7 C8 1.530(3) . ? C10 C11 1.498(2) . ? C20 C21 1.4995(16) . ? O1S C1S 1.434(2) . ? 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 C11 N11 N12 108.63(15) . . ? N13 N12 N11 106.30(15) . . ? N12 N13 N14 110.57(15) . . ? C11 N14 N13 105.76(15) . . ? C21 N21 N22 109.32(10) . . ? N23 N22 N21 106.05(10) . . ? N22 N23 N24 110.85(11) . . ? C21 N24 N23 106.20(10) . . ? C2 C1 C2 121.07(14) 4 . ? C2 C1 C10 119.45(7) 4 . ? C2 C1 C10 119.45(7) . . ? C3 C2 C1 119.03(10) . . ? C3 C2 C5 120.67(10) . . ? C1 C2 C5 120.30(10) . . ? C4 C3 C2 120.57(10) . . ? C4 C3 C20 119.27(10) . . ? C2 C3 C20 120.10(10) . . ? C3 C4 C3 119.63(14) . 4 ? C3 C4 C7 120.16(7) . . ? C3 C4 C7 120.16(7) 4 . ? C2 C5 C6 112.54(11) . . ? C4 C7 C8 111.13(14) . . ? C11 C10 C1 113.27(14) . . ? N14 C11 N11 108.75(16) . . ? N14 C11 C10 125.31(16) . . ? N11 C11 C10 125.94(15) . . ? C21 C20 C3 111.25(10) . . ? N24 C21 N21 107.58(10) . . ? N24 C21 C20 126.30(10) . . ? N21 C21 C20 126.11(11) . . ? 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 C11 N11 N12 N13 0.0 . . . . ? N11 N12 N13 N14 0.0 . . . . ? N12 N13 N14 C11 0.0 . . . . ? C21 N21 N22 N23 0.08(15) . . . . ? N21 N22 N23 N24 -0.17(14) . . . . ? N22 N23 N24 C21 0.19(14) . . . . ? C2 C1 C2 C3 3.6(2) 4 . . . ? C10 C1 C2 C3 -178.57(13) . . . . ? C2 C1 C2 C5 -177.11(9) 4 . . . ? C10 C1 C2 C5 0.69(19) . . . . ? C1 C2 C3 C4 -1.40(17) . . . . ? C5 C2 C3 C4 179.34(12) . . . . ? C1 C2 C3 C20 -178.59(12) . . . . ? C5 C2 C3 C20 2.14(16) . . . . ? C2 C3 C4 C3 -0.8(2) . . . 4 ? C20 C3 C4 C3 176.45(9) . . . 4 ? C2 C3 C4 C7 176.73(12) . . . . ? C20 C3 C4 C7 -6.0(2) . . . . ? C3 C2 C5 C6 88.68(13) . . . . ? C1 C2 C5 C6 -90.57(14) . . . . ? C3 C4 C7 C8 -88.75(13) . . . . ? C3 C4 C7 C8 88.75(13) 4 . . . ? C2 C1 C10 C11 88.92(12) 4 . . . ? C2 C1 C10 C11 -88.92(12) . . . . ? N13 N14 C11 N11 0.0 . . . . ? N13 N14 C11 C10 180.0 . . . . ? N12 N11 C11 N14 0.0 . . . . ? N12 N11 C11 C10 180.0 . . . . ? C1 C10 C11 N14 180.0 . . . . ? C1 C10 C11 N11 0.0 . . . . ? C4 C3 C20 C21 -83.21(14) . . . . ? C2 C3 C20 C21 94.02(12) . . . . ? N23 N24 C21 N21 -0.14(14) . . . . ? N23 N24 C21 C20 -179.04(11) . . . . ? N22 N21 C21 N24 0.04(15) . . . . ? N22 N21 C21 C20 178.94(11) . . . . ? C3 C20 C21 N24 -20.36(16) . . . . ? C3 C20 C21 N21 160.94(12) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N11 H11N O2S 0.92(3) 1.74(3) 2.664(2) 179(3) . N21 H21N O1S 0.864(19) 2.129(18) 2.9367(14) 155.3(16) 6_554 O1S H1SO N14 0.84(4) 2.07(4) 2.771(2) 141(3) . O2S H2SO N24 0.929(18) 2.010(18) 2.9374(13) 176.1(16) . _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.38 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.168 _refine_diff_density_min -0.176 _refine_diff_density_rms 0.037 _exptl_crystal_recrystallization_method 'Slow evaporation from wet MeOH'