Electronic Supplementary Material for CrystEngComm This Journal is © The Royal Society of Chemistry 2004 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Dr Noor Shahina Begum' _publ_contact_author_address ; Department of Chemistry Bangalore University Central College Campus Bangalore Karnataka 560 001 INDIA ; _publ_contact_author_email NOORSB@REDIFFMAIL.COM _publ_section_title ; The Influence of Trimethylsilyl Group: Helical Self-Assembly of Syn-7-Trimethylsilyl-5-norbornene-endo-2,3-dicarboxylic Acid ; loop_ _publ_author_name 'Noor Shahina Begum' C.R.Girija 'Gopalpur Nagendrappa' data_gir1 _database_code_depnum_ccdc_archive 'CCDC 224414' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'syn-7-trimethyl-silyl-5 Norbornene-2,3-endo -dicarboxylic acid' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H18 O4 Si' _chemical_formula_weight 254.35 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pna21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 22.5962(5) _cell_length_b 8.1506(2) _cell_length_c 7.69640(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1417.47(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.192 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 0.166 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _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 'Siemens SMART CCD area detector' _diffrn_measurement_method ' \W scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5612 _diffrn_reflns_av_R_equivalents 0.0608 _diffrn_reflns_av_sigmaI/netI 0.0514 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 23.25 _reflns_number_total 2007 _reflns_number_gt 1866 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens SMART' _computing_cell_refinement 'Siemens SMART' _computing_data_reduction 'Siemens SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement '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. ; _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^)+(0.0893P)^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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.015(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.41(19) _refine_ls_number_reflns 2007 _refine_ls_number_parameters 157 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0410 _refine_ls_R_factor_gt 0.0383 _refine_ls_wR_factor_ref 0.1133 _refine_ls_wR_factor_gt 0.1103 _refine_ls_goodness_of_fit_ref 0.890 _refine_ls_restrained_S_all 0.889 _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 Si1 Si 0.17978(4) 0.55953(11) 0.50148(13) 0.0676(3) Uani 1 1 d . . . O1 O 0.01735(9) 0.2320(3) -0.1143(3) 0.0670(6) Uani 1 1 d . . . H1 H 0.0103 0.1458 -0.1652 0.101 Uiso 1 1 calc R . . O2 O 0.09925(8) 0.0996(3) -0.0282(3) 0.0650(6) Uani 1 1 d . . . O3 O -0.05105(10) 0.2048(3) 0.4197(4) 0.0758(7) Uani 1 1 d . . . H3 H -0.0690 0.1179 0.4298 0.114 Uiso 1 1 calc R . . O4 O -0.00012(10) 0.0603(2) 0.2234(3) 0.0688(6) Uani 1 1 d . . . C1 C 0.13224(11) 0.3649(3) 0.2095(4) 0.0520(6) Uani 1 1 d . . . H1' H 0.1649 0.3983 0.1334 0.062 Uiso 1 1 calc R . . C6 C 0.07013(11) 0.3499(3) 0.1191(4) 0.0505(7) Uani 1 1 d . . . H6 H 0.0628 0.4531 0.0573 0.061 Uiso 1 1 calc R . . C5 C 0.02662(11) 0.3437(3) 0.2774(4) 0.0511(6) Uani 1 1 d . . . H5 H -0.0003 0.4377 0.2715 0.061 Uiso 1 1 calc R . . C4 C 0.07040(12) 0.3673(4) 0.4364(4) 0.0533(7) Uani 1 1 d . . . H4 H 0.0521 0.4040 0.5451 0.064 Uiso 1 1 calc R . . C3 C 0.10659(13) 0.2115(4) 0.4483(4) 0.0587(7) Uani 1 1 d . . . H3' H 0.1041 0.1320 0.5346 0.070 Uiso 1 1 calc R . . C2 C 0.14257(12) 0.2100(4) 0.3122(4) 0.0578(7) Uani 1 1 d . . . H2 H 0.1695 0.1277 0.2848 0.069 Uiso 1 1 calc R . . C7 C 0.11675(12) 0.4866(4) 0.3559(4) 0.0538(7) Uani 1 1 d . . . H7 H 0.0963 0.5818 0.3064 0.065 Uiso 1 1 calc R . . C8 C 0.06453(11) 0.2122(3) -0.0118(4) 0.0525(7) Uani 1 1 d . . . C9 C -0.00905(11) 0.1884(4) 0.3001(4) 0.0547(7) Uani 1 1 d . . . C10 C 0.25136(18) 0.4764(11) 0.4288(9) 0.173(4) Uani 1 1 d . . . H10A H 0.2579 0.5058 0.3095 0.260 Uiso 1 1 calc R . . H10B H 0.2510 0.3591 0.4397 0.260 Uiso 1 1 calc R . . H10C H 0.2825 0.5210 0.4992 0.260 Uiso 1 1 calc R . . C11 C 0.1817(3) 0.7872(6) 0.4817(10) 0.164(3) Uani 1 1 d . . . H11A H 0.1883 0.8169 0.3626 0.246 Uiso 1 1 calc R . . H11B H 0.2132 0.8300 0.5522 0.246 Uiso 1 1 calc R . . H11C H 0.1447 0.8320 0.5201 0.246 Uiso 1 1 calc R . . C12 C 0.16702(18) 0.5035(6) 0.7343(6) 0.0929(11) Uani 1 1 d . . . H12A H 0.1302 0.5496 0.7728 0.139 Uiso 1 1 calc R . . H12B H 0.1987 0.5458 0.8041 0.139 Uiso 1 1 calc R . . H12C H 0.1656 0.3862 0.7454 0.139 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 Si1 0.0687(5) 0.0823(6) 0.0518(5) -0.0120(4) 0.0010(4) -0.0222(4) O1 0.0714(12) 0.0704(12) 0.0593(13) -0.0006(10) -0.0168(10) -0.0053(11) O2 0.0472(10) 0.0778(12) 0.0700(14) -0.0215(11) 0.0011(9) -0.0012(9) O3 0.0669(13) 0.0674(14) 0.0932(18) -0.0029(12) 0.0353(13) -0.0025(9) O4 0.0769(13) 0.0636(13) 0.0659(14) -0.0081(10) 0.0206(12) -0.0166(11) C1 0.0461(13) 0.0636(15) 0.0461(14) -0.0008(12) 0.0016(11) -0.0105(11) C6 0.0519(15) 0.0536(16) 0.0459(16) 0.0025(11) 0.0015(12) -0.0048(12) C5 0.0482(13) 0.0528(14) 0.0523(15) 0.0014(12) 0.0045(12) 0.0022(11) C4 0.0548(15) 0.0597(16) 0.0453(15) -0.0056(12) 0.0072(12) -0.0022(12) C3 0.0597(15) 0.0658(17) 0.0506(17) 0.0062(13) -0.0026(13) -0.0043(13) C2 0.0480(14) 0.0687(17) 0.0568(19) -0.0081(14) -0.0065(14) 0.0026(13) C7 0.0576(15) 0.0551(15) 0.0488(15) -0.0024(13) 0.0050(13) -0.0059(13) C8 0.0462(14) 0.0647(17) 0.0467(15) 0.0020(14) 0.0046(13) -0.0074(13) C9 0.0449(14) 0.0646(18) 0.0545(17) 0.0004(14) 0.0039(14) -0.0001(11) C10 0.056(2) 0.316(9) 0.148(6) -0.134(6) 0.011(3) -0.034(4) C11 0.256(8) 0.099(3) 0.138(5) 0.020(3) -0.077(6) -0.078(4) C12 0.097(3) 0.110(3) 0.071(3) 0.004(2) -0.0123(19) -0.016(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 Si1 C10 1.841(5) . ? Si1 C11 1.862(5) . ? Si1 C12 1.871(4) . ? Si1 C7 1.907(3) . ? O1 C8 1.336(3) . ? O1 H1 0.8200 . ? O2 C8 1.214(4) . ? O3 C9 1.329(4) . ? O3 H3 0.8200 . ? O4 C9 1.217(3) . ? C1 C2 1.507(4) . ? C1 C7 1.541(4) . ? C1 C6 1.571(3) . ? C1 H1 0.9800 . ? C6 C8 1.514(4) . ? C6 C5 1.566(4) . ? C6 H6 0.9800 . ? C5 C9 1.511(4) . ? C5 C4 1.586(4) . ? C5 H5 0.9800 . ? C4 C3 1.513(4) . ? C4 C7 1.557(4) . ? C4 H4 0.9800 . ? C3 C2 1.326(4) . ? C3 H3 0.9300 . ? C2 H2 0.9300 . ? C7 H7 0.9800 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 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 C10 Si1 C11 108.7(4) . . ? C10 Si1 C12 109.7(3) . . ? C11 Si1 C12 109.0(3) . . ? C10 Si1 C7 111.28(18) . . ? C11 Si1 C7 106.3(2) . . ? C12 Si1 C7 111.79(15) . . ? C8 O1 H1 109.5 . . ? C9 O3 H3 109.5 . . ? C2 C1 C7 101.0(3) . . ? C2 C1 C6 107.8(2) . . ? C7 C1 C6 99.8(2) . . ? C2 C1 H1 115.4 . . ? C7 C1 H1 115.4 . . ? C6 C1 H1 115.4 . . ? C8 C6 C5 116.2(2) . . ? C8 C6 C1 115.3(2) . . ? C5 C6 C1 102.7(2) . . ? C8 C6 H6 107.4 . . ? C5 C6 H6 107.4 . . ? C1 C6 H6 107.4 . . ? C9 C5 C6 116.9(2) . . ? C9 C5 C4 110.2(2) . . ? C6 C5 C4 101.82(18) . . ? C9 C5 H5 109.2 . . ? C6 C5 H5 109.2 . . ? C4 C5 H5 109.2 . . ? C3 C4 C7 100.6(2) . . ? C3 C4 C5 106.4(2) . . ? C7 C4 C5 100.8(2) . . ? C3 C4 H4 115.6 . . ? C7 C4 H4 115.6 . . ? C5 C4 H4 115.6 . . ? C2 C3 C4 106.9(3) . . ? C2 C3 H3 126.5 . . ? C4 C3 H3 126.5 . . ? C3 C2 C1 108.2(2) . . ? C3 C2 H2 125.9 . . ? C1 C2 H2 125.9 . . ? C1 C7 C4 92.4(2) . . ? C1 C7 Si1 117.42(18) . . ? C4 C7 Si1 117.6(2) . . ? C1 C7 H7 109.4 . . ? C4 C7 H7 109.4 . . ? Si1 C7 H7 109.4 . . ? O2 C8 O1 123.1(3) . . ? O2 C8 C6 125.2(3) . . ? O1 C8 C6 111.7(2) . . ? O4 C9 O3 122.7(3) . . ? O4 C9 C5 125.1(2) . . ? O3 C9 C5 112.2(2) . . ? Si1 C10 H10A 109.5 . . ? Si1 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? Si1 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? Si1 C11 H11A 109.5 . . ? Si1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? Si1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? Si1 C12 H12A 109.5 . . ? Si1 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? Si1 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 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 C2 C1 C6 C8 -63.1(3) . . . . ? C7 C1 C6 C8 -168.1(2) . . . . ? C2 C1 C6 C5 64.2(3) . . . . ? C7 C1 C6 C5 -40.8(3) . . . . ? C8 C6 C5 C9 10.0(3) . . . . ? C1 C6 C5 C9 -116.7(3) . . . . ? C8 C6 C5 C4 130.1(2) . . . . ? C1 C6 C5 C4 3.4(2) . . . . ? C9 C5 C4 C3 54.8(3) . . . . ? C6 C5 C4 C3 -69.9(2) . . . . ? C9 C5 C4 C7 159.4(2) . . . . ? C6 C5 C4 C7 34.7(2) . . . . ? C7 C4 C3 C2 -34.5(3) . . . . ? C5 C4 C3 C2 70.2(3) . . . . ? C4 C3 C2 C1 1.2(3) . . . . ? C7 C1 C2 C3 33.0(3) . . . . ? C6 C1 C2 C3 -71.2(3) . . . . ? C2 C1 C7 C4 -49.6(2) . . . . ? C6 C1 C7 C4 60.8(2) . . . . ? C2 C1 C7 Si1 73.3(2) . . . . ? C6 C1 C7 Si1 -176.24(19) . . . . ? C3 C4 C7 C1 50.4(2) . . . . ? C5 C4 C7 C1 -58.8(2) . . . . ? C3 C4 C7 Si1 -72.5(3) . . . . ? C5 C4 C7 Si1 178.40(18) . . . . ? C10 Si1 C7 C1 3.4(4) . . . . ? C11 Si1 C7 C1 121.6(3) . . . . ? C12 Si1 C7 C1 -119.6(3) . . . . ? C10 Si1 C7 C4 112.4(4) . . . . ? C11 Si1 C7 C4 -129.4(3) . . . . ? C12 Si1 C7 C4 -10.7(3) . . . . ? C5 C6 C8 O2 -106.5(3) . . . . ? C1 C6 C8 O2 13.6(4) . . . . ? C5 C6 C8 O1 76.0(3) . . . . ? C1 C6 C8 O1 -163.8(2) . . . . ? C6 C5 C9 O4 12.2(4) . . . . ? C4 C5 C9 O4 -103.4(3) . . . . ? C6 C5 C9 O3 -169.9(2) . . . . ? C4 C5 C9 O3 74.6(3) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 23.25 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.185 _refine_diff_density_min -0.191 _refine_diff_density_rms 0.037