# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2002 data_baq _database_code_CSD 174509 _audit_creation_method SHELXL-97 _journal_coden_Cambridge 182 _publ_requested_journal 'Chemical Communications' loop_ _publ_author_name 'Ramana, Chepuri Venkata' 'Baquer, Syed M.' 'Gonnade, Rajesh G.' 'Gurjar, M. K.' _publ_contact_author_name 'Dr Chepuri Venkata Ramana' _publ_contact_author_address ; Division of Organic Chemistry: Technology National Chemical Laboratory Dr. Homi Babha Road Pune Maharashtra 411 008 INDIA ; _publ_contact_author_email 'CHEPURI@DALTON.NCL.RES.IN' _publ_section_title ; An expedient synthesis of tetrakis(cyclopropylmethyl)methane ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'tetrakis (Cyclopropylmethyl) Methane' _chemical_melting_point ? _chemical_formula_moiety 'C17 H28' _chemical_formula_sum 'C17 H28' _chemical_formula_weight 232.39 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' _symmetry_cell_setting 'Monoclinic' _symmetry_space_group_name_H-M P21/n 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 8.8129(7) _cell_length_b 10.3361(8) _cell_length_c 16.6850(13) _cell_angle_alpha 90.00 _cell_angle_beta 100.8580(10) _cell_angle_gamma 90.00 _cell_volume 1492.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2200 _cell_measurement_theta_min 2.33 _cell_measurement_theta_max 24.52 _exptl_crystal_description 'Thin needle' _exptl_crystal_colour 'Colourless' _exptl_crystal_size_max 0.77 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.034 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 0.057 _exptl_absorpt_correction_type 'emperical' _exptl_absorpt_correction_T_min 0.9574 _exptl_absorpt_correction_T_max 0.9958 _exptl_absorpt_process_details 'Bruker SADABS' _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 'CCD Area Detector' _diffrn_measurement_device 'Bruker Smart APEX' _diffrn_measurement_method 'Omega Scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7607 _diffrn_reflns_av_R_equivalents 0.1354 _diffrn_reflns_av_sigmaI/netI 0.1056 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.33 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2620 _reflns_number_gt 2019 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SAINT' _computing_data_reduction 'BRUKER SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL' _computing_publication_material '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^)+(0.0467P)^2^+0.1801P] 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 0.002(2) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2620 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0785 _refine_ls_R_factor_gt 0.0614 _refine_ls_wR_factor_ref 0.1549 _refine_ls_wR_factor_gt 0.1449 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _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 C1 C 0.05642(18) 0.27352(16) 0.18504(9) 0.0385(4) Uani 1 1 d . . . C6 C 0.1659(2) 0.22437(18) 0.26178(10) 0.0463(5) Uani 1 1 d . . . H6A H 0.1882 0.1341 0.2532 0.056 Uiso 1 1 calc R . . H6B H 0.2625 0.2714 0.2667 0.056 Uiso 1 1 calc R . . C10 C 0.0287(2) 0.41939(16) 0.19436(10) 0.0444(5) Uani 1 1 d . . . H10A H -0.0150 0.4318 0.2430 0.053 Uiso 1 1 calc R . . H10B H 0.1283 0.4624 0.2036 0.053 Uiso 1 1 calc R . . C14 C -0.10060(19) 0.20145(17) 0.17388(10) 0.0424(4) Uani 1 1 d . . . H14A H -0.1503 0.2249 0.2190 0.051 Uiso 1 1 calc R . . H14B H -0.1656 0.2332 0.1243 0.051 Uiso 1 1 calc R . . C2 C 0.13179(19) 0.24646(17) 0.10957(10) 0.0438(5) Uani 1 1 d . . . H2A H 0.1474 0.1539 0.1062 0.053 Uiso 1 1 calc R . . H2B H 0.0589 0.2718 0.0610 0.053 Uiso 1 1 calc R . . C15 C -0.0963(2) 0.05573(18) 0.16909(11) 0.0480(5) Uani 1 1 d . . . H15 H -0.0283 0.0132 0.2147 0.058 Uiso 1 1 calc R . . C11 C -0.0748(2) 0.48655(18) 0.12442(11) 0.0493(5) Uani 1 1 d . . . H11 H -0.0495 0.4711 0.0705 0.059 Uiso 1 1 calc R . . C3 C 0.2840(2) 0.3128(2) 0.10763(11) 0.0528(5) Uani 1 1 d . . . H3 H 0.2839 0.4072 0.1131 0.063 Uiso 1 1 calc R . . C16 C -0.2405(2) -0.0166(2) 0.13480(12) 0.0625(6) Uani 1 1 d . . . H16A H -0.3327 0.0333 0.1139 0.075 Uiso 1 1 calc R . . H16B H -0.2588 -0.0980 0.1603 0.075 Uiso 1 1 calc R . . C17 C -0.1100(2) -0.0110(2) 0.08875(13) 0.0637(6) Uani 1 1 d . . . H17A H -0.0497 -0.0889 0.0865 0.076 Uiso 1 1 calc R . . H17B H -0.1235 0.0423 0.0401 0.076 Uiso 1 1 calc R . . C7 C 0.1116(2) 0.23507(19) 0.34245(11) 0.0533(5) Uani 1 1 d . . . H7 H 0.0089 0.1992 0.3433 0.064 Uiso 1 1 calc R . . C12 C -0.1366(3) 0.61792(19) 0.13670(14) 0.0642(6) Uani 1 1 d . . . H12A H -0.1108 0.6555 0.1908 0.077 Uiso 1 1 calc R . . H12B H -0.1441 0.6794 0.0922 0.077 Uiso 1 1 calc R . . C8 C 0.2269(3) 0.2195(2) 0.41906(12) 0.0686(7) Uani 1 1 d . . . H8A H 0.1951 0.1735 0.4638 0.082 Uiso 1 1 calc R . . H8B H 0.3340 0.2070 0.4145 0.082 Uiso 1 1 calc R . . C5 C 0.4324(2) 0.2473(2) 0.14236(13) 0.0683(7) Uani 1 1 d . . . H5A H 0.5171 0.3008 0.1695 0.082 Uiso 1 1 calc R . . H5B H 0.4270 0.1622 0.1661 0.082 Uiso 1 1 calc R . . C9 C 0.1568(3) 0.3476(2) 0.39675(12) 0.0689(6) Uani 1 1 d . . . H9A H 0.2212 0.4135 0.3786 0.083 Uiso 1 1 calc R . . H9B H 0.0823 0.3799 0.4279 0.083 Uiso 1 1 calc R . . C13 C -0.2427(3) 0.5054(2) 0.12528(16) 0.0654(6) Uani 1 1 d . . . C4 C 0.3861(2) 0.2594(2) 0.05233(12) 0.0666(6) Uani 1 1 d . . . H4A H 0.3519 0.1818 0.0214 0.080 Uiso 1 1 calc R . . H4B H 0.4421 0.3206 0.0248 0.080 Uiso 1 1 calc R . . H13A H -0.313(3) 0.500(2) 0.0748(16) 0.098(8) Uiso 1 1 d . . . H13B H -0.282(3) 0.469(2) 0.1718(15) 0.099(8) 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 C1 0.0363(9) 0.0400(10) 0.0381(9) -0.0045(7) 0.0042(7) 0.0016(7) C6 0.0410(10) 0.0488(11) 0.0475(10) -0.0032(8) 0.0043(8) 0.0029(8) C10 0.0425(10) 0.0425(11) 0.0471(10) -0.0057(8) 0.0056(8) -0.0021(8) C14 0.0392(9) 0.0448(10) 0.0430(9) -0.0039(8) 0.0067(7) 0.0016(8) C2 0.0396(9) 0.0483(11) 0.0426(10) -0.0037(8) 0.0057(8) 0.0022(8) C15 0.0504(10) 0.0428(11) 0.0506(10) 0.0020(8) 0.0086(9) -0.0028(8) C11 0.0606(12) 0.0451(11) 0.0425(9) 0.0004(8) 0.0107(9) 0.0036(9) C3 0.0537(11) 0.0502(11) 0.0577(11) 0.0017(9) 0.0183(9) -0.0025(9) C16 0.0594(12) 0.0505(12) 0.0815(14) -0.0096(10) 0.0230(11) -0.0143(10) C17 0.0711(14) 0.0519(12) 0.0731(13) -0.0145(10) 0.0270(11) -0.0094(10) C7 0.0461(10) 0.0677(14) 0.0453(10) 0.0065(9) 0.0069(9) -0.0010(9) C12 0.0760(14) 0.0450(12) 0.0663(13) 0.0006(10) 0.0001(11) 0.0063(11) C8 0.0658(14) 0.0920(18) 0.0458(11) 0.0157(11) 0.0047(10) 0.0122(12) C5 0.0435(11) 0.0942(18) 0.0666(14) 0.0058(12) 0.0087(10) -0.0073(11) C9 0.0748(14) 0.0837(17) 0.0461(11) -0.0069(11) 0.0056(10) 0.0102(12) C13 0.0566(13) 0.0613(15) 0.0733(15) 0.0083(12) -0.0008(12) 0.0044(11) C4 0.0539(12) 0.0892(17) 0.0617(13) 0.0053(11) 0.0235(11) -0.0014(11) _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 C1 C6 1.537(2) . ? C1 C10 1.540(2) . ? C1 C14 1.552(2) . ? C1 C2 1.556(2) . ? C6 C7 1.515(2) . ? C10 C11 1.508(2) . ? C14 C15 1.509(2) . ? C2 C3 1.513(2) . ? C15 C17 1.492(3) . ? C15 C16 1.492(2) . ? C11 C12 1.491(3) . ? C11 C13 1.495(3) . ? C3 C5 1.489(3) . ? C3 C4 1.509(3) . ? C16 C17 1.499(3) . ? C7 C9 1.482(3) . ? C7 C8 1.484(3) . ? C12 C13 1.482(3) . ? C8 C9 1.479(3) . ? C5 C4 1.486(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 C6 C1 C10 109.03(13) . . ? C6 C1 C14 110.30(13) . . ? C10 C1 C14 109.12(13) . . ? C6 C1 C2 108.55(13) . . ? C10 C1 C2 110.96(13) . . ? C14 C1 C2 108.88(13) . . ? C7 C6 C1 117.52(14) . . ? C11 C10 C1 117.18(14) . . ? C15 C14 C1 117.07(14) . . ? C3 C2 C1 116.83(15) . . ? C17 C15 C16 60.33(12) . . ? C17 C15 C14 120.68(16) . . ? C16 C15 C14 119.51(16) . . ? C12 C11 C13 59.49(14) . . ? C12 C11 C10 119.74(16) . . ? C13 C11 C10 120.53(17) . . ? C5 C3 C4 59.40(13) . . ? C5 C3 C2 120.17(17) . . ? C4 C3 C2 118.69(17) . . ? C15 C16 C17 59.82(12) . . ? C15 C17 C16 59.85(12) . . ? C9 C7 C8 59.80(14) . . ? C9 C7 C6 120.43(17) . . ? C8 C7 C6 118.52(17) . . ? C13 C12 C11 60.39(14) . . ? C9 C8 C7 60.04(13) . . ? C4 C5 C3 60.97(13) . . ? C8 C9 C7 60.16(14) . . ? C12 C13 C11 60.12(14) . . ? C5 C4 C3 59.64(13) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.207 _refine_diff_density_min -0.157 _refine_diff_density_rms 0.042