# Supplementary Material (ESI) for ChemComm # This journal is © The Royal Society of Chemistry 1999 # CCDC Number: 182/1476 data_global _publ_contact_author ; James R. Green Chemistry and Biochemistry School of Physical Sciences University of Windsor 401 Sunset Ave Windsor, Ontario, Canada N9B 3P4 ; _publ_contact_author_phone '+ 519 2533000 ext 3545' _publ_contact_author_fax '+ 519 9737098 ' _publ_contact_author_email 'jgreen@uwindsor.ca' _publ_requested_journal 'ChemComm' _publ_requested_coeditor_name ? _publ_section_title ; One step synthesis of [7]metacyclophanediyne complexes form bis(propargyldicobalt) dication equivalents ; loop_ _publ_author_name _publ_author_address 'Green, James R.' ; Chemistry and Biochemistry School of Physical Sciences University of Windsor 401 Sunset Ave Windsor, Ontario, Canada N9B 3P4 ; 'xxxx, xxxxx x.' ; Chemistry and Biochemistry School of Physical Sciences University of Windsor 401 Sunset Ave Windsor, Ontario, Canada N9B 3P4 ; data_diethynylcyclophane _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C16 H16 O3' _chemical_formula_weight 256.30 _chemical_melting_point ? _chemical_compound_source ? 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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.836(3) _cell_length_b 7.925(4) _cell_length_c 11.378(7) _cell_angle_alpha 101.66(4) _cell_angle_beta 98.03(3) _cell_angle_gamma 95.35(5) _cell_volume 679.8(6) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 'reflections from 60 data frames' _cell_measurement_theta_min 1.47 _cell_measurement_theta_max 25 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.34 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.252 _exptl_crystal_density_method ? _exptl_crystal_F_000 272 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.09399 _exptl_absorpt_correction_T_max 0.2627 _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 'Siemens SMART CCD' _diffrn_measurement_method 'hemisphere scans' _diffrn_standards_number '50 standard frames at start and end' _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% <1 _diffrn_reflns_number 3594 _diffrn_reflns_av_R_equivalents 0.0157 _diffrn_reflns_av_sigmaI/netI 0.0322 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2341 _reflns_number_observed 1727 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Siemens SMART' _computing_cell_refinement 'Siemens SAINT' _computing_data_reduction 'Siemens SHELXTL XPREP' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Siemens SHELXTL XP' _computing_publication_material 'Siemens SHELXTL XCIF' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 3 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.1000P)^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 idealized _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2338 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0657 _refine_ls_R_factor_obs 0.0476 _refine_ls_wR_factor_all 0.1535 _refine_ls_wR_factor_obs 0.1355 _refine_ls_goodness_of_fit_all 1.003 _refine_ls_goodness_of_fit_obs 1.103 _refine_ls_restrained_S_all 1.063 _refine_ls_restrained_S_obs 1.103 _refine_ls_shift/esd_max -0.001 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O 0.1141(2) 0.6863(2) 0.88821(12) 0.0551(4) Uani 1 d . . O2 O 0.3825(2) 0.2430(2) 1.05668(11) 0.0549(4) Uani 1 d . . O3 O 0.0869(2) 0.1178(2) 0.65241(11) 0.0540(4) Uani 1 d . . C1 C 0.1047(2) 0.4058(2) 0.7698(2) 0.0447(5) Uani 1 d . . C2 C 0.1407(2) 0.2348(2) 0.76181(15) 0.0410(4) Uani 1 d . . C3 C 0.2461(2) 0.1836(2) 0.8537(2) 0.0403(4) Uani 1 d . . C4 C 0.2858(2) 0.3000(2) 0.96578(15) 0.0408(4) Uani 1 d . . C5 C 0.2323(2) 0.4649(2) 0.9828(2) 0.0423(5) Uani 1 d . . H5A H 0.2509(2) 0.5376(2) 1.0598(2) 0.051 Uiso 1 calc R . C6 C 0.1507(2) 0.5189(2) 0.8827(2) 0.0423(4) Uani 1 d . . C7 C 0.1625(3) 0.8073(2) 1.0016(2) 0.0578(5) Uani 1 d . . H7A H 0.1299(3) 0.9186(2) 0.9931(2) 0.087 Uiso 1 calc R . H7B H 0.2859(3) 0.8175(2) 1.0265(2) 0.087 Uiso 1 calc R . H7C H 0.1045(3) 0.7676(2) 1.0618(2) 0.087 Uiso 1 calc R . C8 C 0.4119(3) 0.3495(3) 1.1760(2) 0.0731(7) Uani 1 d . . H8A H 0.4809(3) 0.2948(3) 1.2303(2) 0.110 Uiso 1 calc R . H8B H 0.3026(3) 0.3654(3) 1.2029(2) 0.110 Uiso 1 calc R . H8C H 0.4721(3) 0.4604(3) 1.1753(2) 0.110 Uiso 1 calc R . C9 C -0.0594(4) -0.0015(4) 0.6513(2) 0.1010(10) Uani 1 d . . H9A H -0.0891(4) -0.0783(4) 0.5726(2) 0.152 Uiso 1 calc R . H9B H -0.1556(4) 0.0606(4) 0.6686(2) 0.152 Uiso 1 calc R . H9C H -0.0327(4) -0.0678(4) 0.7119(2) 0.152 Uiso 1 calc R . C10 C 0.0673(3) 0.4659(3) 0.6512(2) 0.0590(6) Uani 1 d . . H10A H -0.0388(3) 0.4021(3) 0.6015(2) 0.071 Uiso 1 calc R . H10B H 0.0562(3) 0.5889(3) 0.6665(2) 0.071 Uiso 1 calc R . C11 C 0.2202(3) 0.4287(3) 0.5909(2) 0.0567(5) Uani 1 d . . C12 C 0.3478(3) 0.3703(3) 0.5639(2) 0.0581(6) Uani 1 d . . C13 C 0.4966(3) 0.2706(3) 0.5570(2) 0.0694(7) Uani 1 d . . H13A H 0.6048(3) 0.3482(3) 0.5758(2) 0.083 Uiso 1 calc R . H13B H 0.4887(3) 0.1988(3) 0.4761(2) 0.083 Uiso 1 calc R . C14 C 0.4887(3) 0.1604(3) 0.6484(2) 0.0590(6) Uani 1 d . . C15 C 0.4452(3) 0.0887(3) 0.7233(2) 0.0528(5) Uani 1 d . . C16 C 0.3512(2) 0.0347(2) 0.8156(2) 0.0469(5) Uani 1 d . . H16A H 0.4316(2) 0.0191(2) 0.8844(2) 0.056 Uiso 1 calc R . H16B H 0.2753(2) -0.0731(2) 0.7815(2) 0.056 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 O1 0.0686(9) 0.0427(7) 0.0607(9) 0.0191(6) 0.0129(7) 0.0211(6) O2 0.0720(9) 0.0493(8) 0.0429(7) 0.0124(6) -0.0039(6) 0.0200(7) O3 0.0544(8) 0.0575(8) 0.0436(7) 0.0054(6) 0.0033(6) -0.0067(6) C1 0.0406(10) 0.0502(11) 0.0461(10) 0.0168(8) 0.0047(8) 0.0100(8) C2 0.0386(10) 0.0459(10) 0.0376(9) 0.0082(8) 0.0068(7) 0.0012(8) C3 0.0428(10) 0.0349(9) 0.0446(10) 0.0104(8) 0.0094(8) 0.0042(8) C4 0.0432(10) 0.0425(10) 0.0391(9) 0.0152(8) 0.0039(8) 0.0078(8) C5 0.0470(10) 0.0402(10) 0.0402(10) 0.0079(8) 0.0089(8) 0.0072(8) C6 0.0425(10) 0.0393(9) 0.0508(10) 0.0169(8) 0.0116(8) 0.0126(8) C7 0.0658(13) 0.0385(10) 0.0745(14) 0.0131(10) 0.0246(11) 0.0131(9) C8 0.096(2) 0.081(2) 0.0410(12) 0.0111(11) -0.0038(11) 0.0336(14) C9 0.102(2) 0.103(2) 0.075(2) -0.0065(15) 0.0123(15) -0.046(2) C10 0.0632(13) 0.0670(13) 0.0517(12) 0.0247(10) 0.0016(10) 0.0193(11) C11 0.0742(15) 0.0551(12) 0.0420(11) 0.0211(9) 0.0017(10) 0.0034(11) C12 0.0745(15) 0.0545(12) 0.0480(12) 0.0186(9) 0.0138(11) -0.0011(11) C13 0.082(2) 0.0650(14) 0.0690(14) 0.0180(11) 0.0371(12) 0.0034(12) C14 0.0611(13) 0.0549(12) 0.0662(13) 0.0112(11) 0.0264(11) 0.0142(10) C15 0.0546(12) 0.0456(11) 0.0617(12) 0.0090(10) 0.0188(10) 0.0156(9) C16 0.0534(11) 0.0380(9) 0.0513(10) 0.0111(8) 0.0101(9) 0.0104(8) _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 O1 C6 1.375(2) . ? O1 C7 1.423(2) . ? O2 C4 1.372(2) . ? O2 C8 1.422(3) . ? O3 C2 1.378(2) . ? O3 C9 1.414(3) . ? C1 C6 1.389(3) . ? C1 C2 1.398(3) . ? C1 C10 1.519(3) . ? C2 C3 1.390(3) . ? C3 C4 1.391(3) . ? C3 C16 1.527(2) . ? C4 C5 1.394(2) . ? C5 C6 1.391(2) . ? C10 C11 1.486(3) . ? C11 C12 1.193(3) . ? C12 C13 1.471(3) . ? C13 C14 1.491(3) . ? C14 C15 1.186(3) . ? C15 C16 1.472(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 O1 C7 117.85(15) . . ? C4 O2 C8 118.1(2) . . ? C2 O3 C9 114.2(2) . . ? C6 C1 C2 117.1(2) . . ? C6 C1 C10 123.4(2) . . ? C2 C1 C10 117.1(2) . . ? O3 C2 C3 118.7(2) . . ? O3 C2 C1 118.1(2) . . ? C3 C2 C1 122.8(2) . . ? C2 C3 C4 116.9(2) . . ? C2 C3 C16 117.2(2) . . ? C4 C3 C16 123.3(2) . . ? O2 C4 C3 115.8(2) . . ? O2 C4 C5 122.7(2) . . ? C3 C4 C5 121.5(2) . . ? C6 C5 C4 118.9(2) . . ? O1 C6 C1 116.1(2) . . ? O1 C6 C5 122.6(2) . . ? C1 C6 C5 121.3(2) . . ? C11 C10 C1 104.3(2) . . ? C12 C11 C10 162.4(2) . . ? C11 C12 C13 163.8(2) . . ? C12 C13 C14 106.1(2) . . ? C15 C14 C13 164.0(2) . . ? C14 C15 C16 162.9(2) . . ? C15 C16 C3 104.31(15) . . ? _refine_diff_density_max 0.162 _refine_diff_density_min -0.238 _refine_diff_density_rms 0.042