Supplementary Material (ESI) for J. Mater. Chem. This journal is (C) The Royal Society of Chemistry 2003 data_x: _database_code_CSD 195726 _journal_coden_Cambridge 1145 loop_ _publ_author_name 'Carsten Tschierske' 'Peter R. Ashton' 'Torsten Hegmann' 'Bernhard Neumann' 'Christoph Wagner' 'Raik Wolf' _publ_contact_author_name 'Prof Carsten Tschierske' _publ_contact_author_address ; Department of Organic Chemistry Martin Luther University Halle Wittenberg Kurt-Mothe Str. 2 Halle D-06120 GERMANY ; _publ_contact_author_email 'TSCHIERSKE@CHEMIE.UNI-HALLE.DE' _publ_requested_journal 'Journal of Materials Chemistry' _publ_section_title ; Liquid crystalline macrocycles containing phenylpyrimidine units ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H44 N4 O10' _chemical_formula_weight 692.75 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' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pcab loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y+1/2, z+1/2' 'x+1/2, -y, -z+1/2' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x, y-1/2, -z-1/2' '-x-1/2, y, z-1/2' 'x-1/2, -y-1/2, z' _cell_length_a 8.9755(15) _cell_length_b 16.220(3) _cell_length_c 23.691(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3449.0(14) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2000 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.334 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1472 _exptl_absorpt_coefficient_mu 0.098 _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 STOE-IPDS _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11807 _diffrn_reflns_av_R_equivalents 0.1987 _diffrn_reflns_av_sigmaI/netI 0.1686 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 24.00 _reflns_number_total 2616 _reflns_number_gt 1015 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0368P)^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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2616 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1691 _refine_ls_R_factor_gt 0.0547 _refine_ls_wR_factor_ref 0.1237 _refine_ls_wR_factor_gt 0.0914 _refine_ls_goodness_of_fit_ref 0.830 _refine_ls_restrained_S_all 0.830 _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 1.2402(6) 0.6091(3) 0.44052(19) 0.0424(13) Uani 1 1 d . . . C2 C 0.9963(6) 0.6398(3) 0.44989(18) 0.0496(14) Uani 1 1 d . . . H2 H 0.9069 0.6581 0.4345 0.060 Uiso 1 1 calc R . . C3 C 0.9988(6) 0.6197(2) 0.50801(17) 0.0349(12) Uani 1 1 d . . . C4 C 1.1358(6) 0.5927(3) 0.52695(18) 0.0431(13) Uani 1 1 d . . . H4 H 1.1437 0.5777 0.5647 0.052 Uiso 1 1 calc R . . C5 C 0.8688(6) 0.6270(3) 0.54569(17) 0.0361(12) Uani 1 1 d . . . C6 C 0.8645(6) 0.5848(3) 0.59761(17) 0.0433(13) Uani 1 1 d . . . H6 H 0.9449 0.5519 0.6080 0.052 Uiso 1 1 calc R . . C7 C 0.7441(6) 0.5910(3) 0.63327(17) 0.0431(13) Uani 1 1 d . . . H7 H 0.7442 0.5631 0.6676 0.052 Uiso 1 1 calc R . . C8 C 0.6233(6) 0.6387(3) 0.61818(17) 0.0367(12) Uani 1 1 d . . . C9 C 0.6226(6) 0.6811(3) 0.56741(16) 0.0358(12) Uani 1 1 d . . . H9 H 0.5412 0.7132 0.5571 0.043 Uiso 1 1 calc R . . C10 C 0.7456(6) 0.6747(3) 0.53216(18) 0.0397(13) Uani 1 1 d . . . H10 H 0.7454 0.7035 0.4982 0.048 Uiso 1 1 calc R . . C11 C 0.3760(6) 0.6846(3) 0.64145(18) 0.0425(13) Uani 1 1 d . . . H11A H 0.3393 0.6661 0.6051 0.051 Uiso 1 1 calc R . . H11B H 0.3974 0.7431 0.6391 0.051 Uiso 1 1 calc R . . C12 C 0.2612(6) 0.6684(3) 0.68679(18) 0.0443(13) Uani 1 1 d . . . H12A H 0.3052 0.6768 0.7237 0.053 Uiso 1 1 calc R . . H12B H 0.1785 0.7065 0.6827 0.053 Uiso 1 1 calc R . . C13 C 0.1176(6) 0.5621(3) 0.72893(18) 0.0511(15) Uani 1 1 d . . . H13A H 0.0310 0.5977 0.7313 0.061 Uiso 1 1 calc R . . H13B H 0.1735 0.5673 0.7638 0.061 Uiso 1 1 calc R . . C14 C 0.0697(6) 0.4750(3) 0.7208(2) 0.0549(15) Uani 1 1 d . . . H14A H 0.0053 0.4585 0.7517 0.066 Uiso 1 1 calc R . . H14B H 0.0137 0.4702 0.6860 0.066 Uiso 1 1 calc R . . C15 C 0.1628(6) 0.3408(3) 0.70027(19) 0.0540(15) Uani 1 1 d . . . H15A H 0.0833 0.3419 0.6725 0.065 Uiso 1 1 calc R . . H15B H 0.1300 0.3077 0.7320 0.065 Uiso 1 1 calc R . . C16 C 0.2999(7) 0.3034(3) 0.67475(19) 0.0582(15) Uani 1 1 d . . . H16A H 0.3824 0.3114 0.7006 0.070 Uiso 1 1 calc R . . H16B H 0.2843 0.2445 0.6709 0.070 Uiso 1 1 calc R . . C17 C 0.3905(6) 0.4192(3) 0.62033(19) 0.0503(14) Uani 1 1 d . . . H17A H 0.4339 0.4335 0.6565 0.060 Uiso 1 1 calc R . . H17B H 0.3073 0.4559 0.6132 0.060 Uiso 1 1 calc R . . C18 C 0.5052(6) 0.4281(3) 0.57436(17) 0.0472(14) Uani 1 1 d . . . H18A H 0.4735 0.3989 0.5407 0.057 Uiso 1 1 calc R . . H18B H 0.5190 0.4857 0.5649 0.057 Uiso 1 1 calc R . . O1 O 0.5063(4) 0.64031(19) 0.65644(11) 0.0443(9) Uani 1 1 d . . . O2 O 0.2093(4) 0.58626(19) 0.68184(11) 0.0458(9) Uani 1 1 d . . . O3 O 0.1947(4) 0.4232(2) 0.71883(12) 0.0489(9) Uani 1 1 d . . . O4 O 0.3405(4) 0.3359(2) 0.62114(13) 0.0540(10) Uani 1 1 d . . . O5 O 0.6420(4) 0.39353(19) 0.59555(12) 0.0497(9) Uani 1 1 d . . . N1 N 1.2604(5) 0.5864(2) 0.49428(15) 0.0473(11) Uani 1 1 d . . . N2 N 1.1149(5) 0.6342(3) 0.41559(15) 0.0515(12) Uani 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 0.038(4) 0.047(3) 0.042(3) -0.002(2) 0.000(3) -0.004(3) C2 0.046(4) 0.065(3) 0.038(3) 0.008(3) -0.003(3) 0.004(3) C3 0.039(4) 0.029(3) 0.036(3) -0.006(2) -0.004(3) -0.005(2) C4 0.029(4) 0.066(3) 0.035(3) -0.002(2) 0.001(3) -0.002(3) C5 0.040(4) 0.035(3) 0.033(3) 0.000(2) -0.004(2) 0.000(3) C6 0.043(4) 0.046(3) 0.040(3) 0.011(2) -0.004(3) 0.004(3) C7 0.044(4) 0.053(3) 0.032(3) 0.015(2) -0.002(2) 0.003(3) C8 0.035(4) 0.040(3) 0.036(3) 0.008(2) 0.000(2) -0.005(2) C9 0.041(4) 0.035(3) 0.031(3) 0.005(2) -0.004(2) 0.003(2) C10 0.043(4) 0.043(3) 0.033(3) 0.007(2) -0.007(2) 0.001(3) C11 0.033(4) 0.049(3) 0.046(3) 0.006(2) 0.000(2) 0.004(3) C12 0.049(4) 0.038(3) 0.046(3) -0.002(2) 0.000(2) 0.009(3) C13 0.042(4) 0.067(4) 0.045(3) 0.011(3) 0.018(3) 0.012(3) C14 0.058(4) 0.060(4) 0.047(3) 0.013(3) 0.008(3) 0.007(3) C15 0.065(5) 0.052(3) 0.045(3) 0.006(3) 0.003(3) -0.009(3) C16 0.072(5) 0.052(3) 0.051(3) 0.001(3) -0.006(3) 0.004(3) C17 0.047(4) 0.058(3) 0.046(3) 0.002(3) 0.002(3) 0.004(3) C18 0.042(4) 0.061(3) 0.039(3) -0.002(3) 0.000(3) -0.002(3) O1 0.037(2) 0.060(2) 0.0358(17) 0.0098(16) 0.0028(16) 0.0037(19) O2 0.051(3) 0.048(2) 0.0375(17) 0.0049(16) 0.0131(15) -0.0016(18) O3 0.052(3) 0.053(2) 0.0412(19) 0.0045(17) 0.0016(16) 0.0055(19) O4 0.060(3) 0.055(2) 0.047(2) -0.0004(18) 0.0082(17) -0.0098(19) O5 0.042(3) 0.072(2) 0.0352(18) 0.0074(17) 0.0024(17) 0.0068(19) N1 0.049(3) 0.059(3) 0.035(2) 0.004(2) -0.009(2) 0.002(2) N2 0.038(4) 0.077(3) 0.040(2) 0.012(2) 0.003(2) 0.008(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 C1 N2 1.334(6) . ? C1 N1 1.338(5) . ? C1 O5 1.360(6) 5_766 ? C2 N2 1.342(6) . ? C2 C3 1.415(5) . ? C3 C4 1.380(6) . ? C3 C5 1.474(7) . ? C4 N1 1.364(6) . ? C5 C10 1.387(6) . ? C5 C6 1.409(6) . ? C6 C7 1.376(6) . ? C7 C8 1.380(6) . ? C8 C9 1.385(5) . ? C8 O1 1.387(5) . ? C9 C10 1.388(6) . ? C11 O1 1.418(5) . ? C11 C12 1.511(6) . ? C12 O2 1.417(5) . ? C13 O2 1.440(5) . ? C13 C14 1.489(6) . ? C14 O3 1.403(5) . ? C15 O3 1.436(5) . ? C15 C16 1.499(7) . ? C16 O4 1.422(5) . ? C17 O4 1.424(5) . ? C17 C18 1.505(6) . ? C18 O5 1.440(6) . ? O5 C1 1.360(6) 5_766 ? 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 N2 C1 N1 128.3(5) . . ? N2 C1 O5 112.8(4) . 5_766 ? N1 C1 O5 118.9(5) . 5_766 ? N2 C2 C3 124.1(5) . . ? C4 C3 C2 113.8(4) . . ? C4 C3 C5 122.2(4) . . ? C2 C3 C5 123.9(5) . . ? N1 C4 C3 124.7(4) . . ? C10 C5 C6 116.8(5) . . ? C10 C5 C3 122.4(4) . . ? C6 C5 C3 120.8(5) . . ? C7 C6 C5 121.5(5) . . ? C6 C7 C8 120.0(4) . . ? C7 C8 C9 120.4(4) . . ? C7 C8 O1 115.9(4) . . ? C9 C8 O1 123.7(4) . . ? C8 C9 C10 118.8(4) . . ? C5 C10 C9 122.5(4) . . ? O1 C11 C12 107.3(4) . . ? O2 C12 C11 109.2(4) . . ? O2 C13 C14 108.9(4) . . ? O3 C14 C13 110.0(4) . . ? O3 C15 C16 109.6(4) . . ? O4 C16 C15 114.9(4) . . ? O4 C17 C18 108.5(4) . . ? O5 C18 C17 107.1(4) . . ? C8 O1 C11 118.0(3) . . ? C12 O2 C13 112.3(3) . . ? C14 O3 C15 114.1(4) . . ? C16 O4 C17 116.4(4) . . ? C1 O5 C18 117.1(4) 5_766 . ? C1 N1 C4 114.1(4) . . ? C1 N2 C2 114.9(4) . . ? _diffrn_measured_fraction_theta_max 0.966 _diffrn_reflns_theta_full 24.00 _diffrn_measured_fraction_theta_full 0.966 _refine_diff_density_max 0.190 _refine_diff_density_min -0.226 _refine_diff_density_rms 0.048