# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. #TrackingRef '- C2CC30410D_ccdc_863773_cif.txt' _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dr Naseer, Muhammad' _publ_contact_author_email moazzam@qau.edu.pk _publ_section_title ; Layer-by-layer pyramid-like assembly of supramolecular hexagonal blocks, driven by p-p stacking of electron-rich and -deficient aromatic rings ; _publ_author_name M.Naseer # Attachment '- sx2610.cif' data_a #TrackingRef '- C2CC30410D_ccdc_863773_cif.txt' _database_code_depnum_ccdc_archive 'CCDC 863773' #TrackingRef '- sx2610.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H27 N3 O6' _chemical_formula_sum 'C30 H27 N3 O6' _chemical_formula_weight 525.55 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 trigonal _symmetry_space_group_name_H-M R-3 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 17.693(3) _cell_length_b 17.693(3) _cell_length_c 13.907(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 3770.4(11) _cell_formula_units_Z 6 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 638 _cell_measurement_theta_min 2.17 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.46 _exptl_crystal_size_min 0.46 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.389 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1656 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9481 _exptl_absorpt_correction_T_max 0.9563 _exptl_absorpt_process_details 'ABSCOR by T.Higashi 8 March, 1995' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku raxis Rapid IP Area Detector' _diffrn_measurement_method '\w scans at fixed \c = 45\%' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3139 _diffrn_reflns_av_R_equivalents 0.0214 _diffrn_reflns_av_sigmaI/netI 0.0517 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.04 _diffrn_reflns_theta_max 25.49 _reflns_number_total 1570 _reflns_number_gt 1195 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Rapid Auto(Rigaku 2001)' _computing_cell_refinement 'Rapid Auto(Rigaku 2001)' _computing_data_reduction 'Rapid Auto(Rigaku 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP in Siemens SHELXTL (Sheldrick, 1994)' _computing_publication_material 'SHELX97 (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^)+(0.0462P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1570 _refine_ls_number_parameters 118 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0701 _refine_ls_R_factor_gt 0.0401 _refine_ls_wR_factor_ref 0.0989 _refine_ls_wR_factor_gt 0.0892 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.012 _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 O1 O 0.08161(8) 0.43243(8) 0.09258(9) 0.0381(4) Uani 1 1 d . . . H1A H 0.1271 0.4638 0.0607 0.057 Uiso 1 1 calc R . . O2 O 0.19945(7) 0.69013(7) 0.03152(8) 0.0303(3) Uani 1 1 d . . . N1 N 0.34328(9) 0.74907(9) 0.03729(9) 0.0245(4) Uani 1 1 d . . . C1 C 0.06879(11) 0.34956(11) 0.09912(12) 0.0277(4) Uani 1 1 d . . . C2 C -0.00419(11) 0.28867(11) 0.14973(13) 0.0299(4) Uani 1 1 d . . . H2A H -0.0431 0.3050 0.1772 0.036 Uiso 1 1 calc R . . C3 C -0.01990(11) 0.20418(11) 0.15993(12) 0.0262(4) Uani 1 1 d . . . H3A H -0.0697 0.1631 0.1951 0.031 Uiso 1 1 calc R . . C4 C 0.03542(10) 0.17798(10) 0.11994(10) 0.0214(4) Uani 1 1 d . . . C5 C 0.10850(11) 0.24058(11) 0.06979(11) 0.0246(4) Uani 1 1 d . . . H5A H 0.1477 0.2246 0.0422 0.030 Uiso 1 1 calc R . . C6 C 0.12499(11) 0.32518(11) 0.05952(12) 0.0279(4) Uani 1 1 d . . . H6A H 0.1751 0.3667 0.0251 0.033 Uiso 1 1 calc R . . C7 C 0.01743(10) 0.08673(10) 0.12681(11) 0.0211(4) Uani 1 1 d . . . C8 C -0.06806(10) 0.01741(10) 0.12735(10) 0.0225(4) Uani 1 1 d . . . H8A H -0.1148 0.0293 0.1281 0.027 Uiso 1 1 calc R . . C9 C 0.11203(11) 0.61622(12) 0.02135(14) 0.0344(5) Uani 1 1 d . . . H9A H 0.0700 0.6369 0.0191 0.052 Uiso 1 1 calc R . . H9B H 0.0988 0.5769 0.0763 0.052 Uiso 1 1 calc R . . H9C H 0.1082 0.5849 -0.0382 0.052 Uiso 1 1 calc R . . C10 C 0.26551(11) 0.67513(11) 0.03590(11) 0.0241(4) 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 O1 0.0371(8) 0.0217(7) 0.0562(9) 0.0039(6) 0.0052(6) 0.0152(6) O2 0.0209(7) 0.0242(7) 0.0477(8) 0.0000(5) 0.0023(5) 0.0126(6) N1 0.0217(8) 0.0229(8) 0.0283(8) -0.0008(6) -0.0003(6) 0.0107(6) C1 0.0310(10) 0.0199(9) 0.0318(10) -0.0030(7) -0.0060(7) 0.0125(8) C2 0.0277(10) 0.0269(10) 0.0389(11) -0.0030(7) 0.0023(8) 0.0166(8) C3 0.0234(9) 0.0232(9) 0.0298(9) -0.0004(7) 0.0020(7) 0.0100(8) C4 0.0222(9) 0.0211(9) 0.0204(8) -0.0028(6) -0.0048(7) 0.0105(7) C5 0.0227(9) 0.0246(9) 0.0272(9) -0.0020(7) -0.0003(7) 0.0123(8) C6 0.0241(9) 0.0225(9) 0.0318(9) 0.0025(7) 0.0002(7) 0.0077(8) C7 0.0242(9) 0.0223(9) 0.0169(8) -0.0018(6) -0.0008(6) 0.0118(7) C8 0.0227(9) 0.0258(9) 0.0214(9) -0.0005(6) -0.0002(7) 0.0139(8) C9 0.0199(9) 0.0289(10) 0.0545(12) -0.0015(8) 0.0022(8) 0.0122(8) C10 0.0252(9) 0.0264(9) 0.0215(9) 0.0003(7) 0.0017(7) 0.0135(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 C1 1.3702(19) . ? O1 H1A 0.8400 . ? O2 C10 1.3231(19) . ? O2 C9 1.449(2) . ? N1 C10 1.322(2) 3_565 ? N1 C10 1.344(2) . ? C1 C6 1.381(2) . ? C1 C2 1.390(2) . ? C2 C3 1.385(2) . ? C2 H2A 0.9500 . ? C3 C4 1.391(2) . ? C3 H3A 0.9500 . ? C4 C5 1.397(2) . ? C4 C7 1.484(2) . ? C5 C6 1.382(2) . ? C5 H5A 0.9500 . ? C6 H6A 0.9500 . ? C7 C8 1.392(2) . ? C7 C8 1.399(2) 3 ? C8 C7 1.399(2) 2 ? C8 H8A 0.9500 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 N1 1.322(2) 2_665 ? 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 C1 O1 H1A 109.5 . . ? C10 O2 C9 118.35(13) . . ? C10 N1 C10 112.75(16) 3_565 . ? O1 C1 C6 123.23(16) . . ? O1 C1 C2 117.10(15) . . ? C6 C1 C2 119.67(15) . . ? C3 C2 C1 119.72(16) . . ? C3 C2 H2A 120.1 . . ? C1 C2 H2A 120.1 . . ? C2 C3 C4 121.60(16) . . ? C2 C3 H3A 119.2 . . ? C4 C3 H3A 119.2 . . ? C3 C4 C5 117.49(15) . . ? C3 C4 C7 122.19(15) . . ? C5 C4 C7 120.30(14) . . ? C6 C5 C4 121.38(16) . . ? C6 C5 H5A 119.3 . . ? C4 C5 H5A 119.3 . . ? C1 C6 C5 120.14(16) . . ? C1 C6 H6A 119.9 . . ? C5 C6 H6A 119.9 . . ? C8 C7 C8 118.44(16) . 3 ? C8 C7 C4 120.43(14) . . ? C8 C7 C4 121.03(14) 3 . ? C7 C8 C7 121.55(16) . 2 ? C7 C8 H8A 119.2 . . ? C7 C8 H8A 119.2 2 . ? O2 C9 H9A 109.5 . . ? O2 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? O2 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N1 C10 O2 120.29(15) 2_665 . ? N1 C10 N1 127.21(16) 2_665 . ? O2 C10 N1 112.50(14) . . ? 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 O1 C1 C2 C3 -179.09(15) . . . . ? C6 C1 C2 C3 0.0(3) . . . . ? C1 C2 C3 C4 -0.5(3) . . . . ? C2 C3 C4 C5 0.8(2) . . . . ? C2 C3 C4 C7 -177.40(15) . . . . ? C3 C4 C5 C6 -0.5(2) . . . . ? C7 C4 C5 C6 177.71(15) . . . . ? O1 C1 C6 C5 179.31(15) . . . . ? C2 C1 C6 C5 0.3(3) . . . . ? C4 C5 C6 C1 0.0(3) . . . . ? C3 C4 C7 C8 32.7(2) . . . . ? C5 C4 C7 C8 -145.40(16) . . . . ? C3 C4 C7 C8 -150.94(15) . . . 3 ? C5 C4 C7 C8 30.9(2) . . . 3 ? C8 C7 C8 C7 -1.1(3) 3 . . 2 ? C4 C7 C8 C7 175.35(10) . . . 2 ? C9 O2 C10 N1 -4.4(2) . . . 2_665 ? C9 O2 C10 N1 174.86(14) . . . . ? C10 N1 C10 N1 2.9(3) 3_565 . . 2_665 ? C10 N1 C10 O2 -176.23(8) 3_565 . . . ? 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 O1 H1A N1 0.84 2.27 3.0305(19) 149.8 2_665 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.49 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.261 _refine_diff_density_min -0.196 _refine_diff_density_rms 0.041