# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_rafqm68aa _database_code_depnum_ccdc_archive 'CCDC 905203' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '3(C15 H12 N2 O), H2 O' _chemical_formula_sum 'C45 H38 N6 O4' _chemical_formula_weight 726.81 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 35.272(10) _cell_length_b 35.272(10) _cell_length_c 5.2820(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 5691(3) _cell_formula_units_Z 6 _cell_measurement_temperature 290(2) _cell_measurement_reflns_used 1099 _cell_measurement_theta_min 3 _cell_measurement_theta_max 31 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.272 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2292 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.89 _exptl_absorpt_correction_T_max 0.90 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 290(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 'MAR345 with image plate detector' _diffrn_measurement_method 'phi scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13324 _diffrn_reflns_av_R_equivalents 0.0473 _diffrn_reflns_av_sigmaI/netI 0.0304 _diffrn_reflns_limit_h_min -50 _diffrn_reflns_limit_h_max 52 _diffrn_reflns_limit_k_min -48 _diffrn_reflns_limit_k_max 48 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 32.25 _reflns_number_total 3163 _reflns_number_gt 2280 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'MARXDS (Claudio Klein, 2005)' _computing_cell_refinement 'AUTOMAR (Claudio Klein, 2007)' _computing_data_reduction 'MARSCALE (Claudio Klein, 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP (Brueggermann and Smith, 1990)' _computing_publication_material 'PLATON (Spek, 1990)' _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^)+(0.0722P)^2^+2.0180P] 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 3163 _refine_ls_number_parameters 171 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.1145 _refine_ls_R_factor_gt 0.0762 _refine_ls_wR_factor_ref 0.1954 _refine_ls_wR_factor_gt 0.1766 _refine_ls_goodness_of_fit_ref 1.210 _refine_ls_restrained_S_all 1.212 _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 0.45338(5) 0.46395(5) 0.6936(3) 0.0745(5) Uani 1 1 d U . . N1 N 0.42580(5) 0.49968(5) 0.9203(3) 0.0563(4) Uani 1 1 d . . . N2 N 0.49046(6) 0.53770(7) 0.7028(4) 0.0762(6) Uani 1 1 d . . . H2A H 0.5108 0.5391 0.6070 0.091 Uiso 1 1 calc R . . H2B H 0.4918 0.5614 0.7570 0.091 Uiso 1 1 calc R . . C1 C 0.42459(7) 0.53895(7) 0.9722(4) 0.0602(5) Uani 1 1 d . . . C2 C 0.45048(9) 0.56697(9) 1.1585(5) 0.0790(7) Uani 1 1 d . . . H2 H 0.4685 0.5604 1.2547 0.095 Uiso 1 1 calc R . . C3 C 0.44947(11) 0.60557(10) 1.2025(6) 0.0960(9) Uani 1 1 d . . . H3 H 0.4671 0.6250 1.3271 0.115 Uiso 1 1 calc R . . C4 C 0.42283(11) 0.61443(10) 1.0640(7) 0.0991(9) Uani 1 1 d . . . H4 H 0.4218 0.6398 1.0961 0.119 Uiso 1 1 calc R . . C5 C 0.39719(10) 0.58656(9) 0.8762(6) 0.0887(8) Uani 1 1 d U . . H5 H 0.3799 0.5940 0.7790 0.106 Uiso 1 1 calc R . . C6 C 0.39638(7) 0.54744(8) 0.8275(4) 0.0661(6) Uani 1 1 d U . . C7 C 0.36704(8) 0.51742(9) 0.6327(5) 0.0735(6) Uani 1 1 d . . . H7 H 0.3621 0.5303 0.4928 0.088 Uiso 1 1 calc R . . C8 C 0.34693(7) 0.47432(8) 0.6330(4) 0.0659(6) Uani 1 1 d . . . H8 H 0.3294 0.4602 0.4934 0.079 Uiso 1 1 calc R . . C9 C 0.34923(7) 0.44619(7) 0.8309(4) 0.0581(5) Uani 1 1 d U . . C10 C 0.31276(8) 0.40569(8) 0.8820(5) 0.0697(6) Uani 1 1 d U . . H10 H 0.2877 0.3961 0.7835 0.084 Uiso 1 1 calc R . . C11 C 0.31274(8) 0.37937(8) 1.0758(5) 0.0714(6) Uani 1 1 d . . . H11 H 0.2880 0.3524 1.1073 0.086 Uiso 1 1 calc R . . C12 C 0.34969(8) 0.39339(8) 1.2215(5) 0.0709(6) Uani 1 1 d . . . H12 H 0.3498 0.3759 1.3527 0.085 Uiso 1 1 calc R . . C13 C 0.38635(7) 0.43300(7) 1.1749(4) 0.0634(6) Uani 1 1 d . . . H13 H 0.4110 0.4426 1.2763 0.076 Uiso 1 1 calc R . . C14 C 0.38648(6) 0.45869(6) 0.9761(3) 0.0515(5) Uani 1 1 d . . . C15 C 0.45700(6) 0.49919(7) 0.7668(4) 0.0561(5) Uani 1 1 d U . . O1W O 0.3333 0.6667 0.1667 0.68(6) Uani 1 6 d SD . . H1WO H 0.343(17) 0.657(17) 0.2975(16) 0.822 Uiso 0.33 1 d PD . . O2W O 0.3333 0.6667 0.6667 0.68(6) Uani 1 6 d SD . . H2WO H 0.324(17) 0.676(17) 0.7975(16) 0.822 Uiso 0.33 1 d PD . . 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 0.0733(10) 0.0713(10) 0.0789(11) -0.0006(8) 0.0088(8) 0.0361(9) N1 0.0499(9) 0.0560(10) 0.0588(10) -0.0021(7) 0.0024(7) 0.0234(8) N2 0.0639(12) 0.0713(13) 0.0863(14) -0.0023(10) 0.0123(10) 0.0285(10) C1 0.0575(12) 0.0625(13) 0.0572(12) -0.0007(9) 0.0047(9) 0.0274(10) C2 0.0779(17) 0.0750(16) 0.0737(16) -0.0064(12) 0.0006(12) 0.0304(14) C3 0.099(2) 0.083(2) 0.091(2) -0.0125(15) 0.0046(16) 0.0342(17) C4 0.105(2) 0.0775(19) 0.112(2) -0.0041(17) 0.0194(19) 0.0432(18) C5 0.0924(19) 0.0744(15) 0.102(2) 0.0024(14) 0.0099(15) 0.0439(16) C6 0.0645(13) 0.0676(13) 0.0650(13) 0.0040(10) 0.0073(10) 0.0321(11) C7 0.0704(15) 0.0779(16) 0.0733(15) 0.0060(11) 0.0005(11) 0.0378(13) C8 0.0617(13) 0.0676(14) 0.0657(13) -0.0006(10) -0.0039(10) 0.0304(12) C9 0.0540(11) 0.0622(11) 0.0572(11) -0.0013(9) -0.0008(8) 0.0283(8) C10 0.0571(12) 0.0669(13) 0.0780(15) 0.0001(10) -0.0010(10) 0.0258(9) C11 0.0655(15) 0.0653(14) 0.0785(15) 0.0024(11) 0.0073(11) 0.0289(12) C12 0.0750(16) 0.0691(15) 0.0693(14) 0.0036(11) 0.0040(11) 0.0365(13) C13 0.0629(13) 0.0660(14) 0.0613(13) -0.0003(10) -0.0016(9) 0.0323(11) C14 0.0480(11) 0.0546(11) 0.0505(10) -0.0014(8) 0.0019(8) 0.0246(9) C15 0.0497(11) 0.0645(11) 0.0513(11) -0.0004(8) -0.0018(8) 0.0264(10) O1W 0.366(9) 0.366(9) 1.32(19) 0.000 0.000 0.183(4) O2W 0.366(9) 0.366(9) 1.32(19) 0.000 0.000 0.183(4) _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 C15 1.246(3) . ? N1 C15 1.374(3) . ? N1 C1 1.433(3) . ? N1 C14 1.447(2) . ? N2 C15 1.322(3) . ? N2 H2A 0.8600 . ? N2 H2B 0.8600 . ? C1 C2 1.370(3) . ? C1 C6 1.401(3) . ? C2 C3 1.399(4) . ? C2 H2 0.9300 . ? C3 C4 1.345(5) . ? C3 H3 0.9300 . ? C4 C5 1.371(4) . ? C4 H4 0.9300 . ? C5 C6 1.390(3) . ? C5 H5 0.9300 . ? C6 C7 1.468(3) . ? C7 C8 1.318(3) . ? C7 H7 0.9300 . ? C8 C9 1.471(3) . ? C8 H8 0.9300 . ? C9 C14 1.389(3) . ? C9 C10 1.389(3) . ? C10 C11 1.381(3) . ? C10 H10 0.9300 . ? C11 C12 1.375(3) . ? C11 H11 0.9300 . ? C12 C13 1.370(3) . ? C12 H12 0.9300 . ? C13 C14 1.386(3) . ? C13 H13 0.9300 . ? O1W H1WO 0.903(10) . ? O2W H2WO 0.902(10) . ? 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 C15 N1 C1 122.41(17) . . ? C15 N1 C14 118.75(17) . . ? C1 N1 C14 116.72(16) . . ? C15 N2 H2A 120.0 . . ? C15 N2 H2B 120.0 . . ? H2A N2 H2B 120.0 . . ? C2 C1 C6 121.7(2) . . ? C2 C1 N1 120.2(2) . . ? C6 C1 N1 118.04(19) . . ? C1 C2 C3 119.3(3) . . ? C1 C2 H2 120.3 . . ? C3 C2 H2 120.3 . . ? C4 C3 C2 119.8(3) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C3 C4 C5 120.9(3) . . ? C3 C4 H4 119.5 . . ? C5 C4 H4 119.5 . . ? C4 C5 C6 121.6(3) . . ? C4 C5 H5 119.2 . . ? C6 C5 H5 119.2 . . ? C5 C6 C1 116.6(2) . . ? C5 C6 C7 120.2(2) . . ? C1 C6 C7 123.2(2) . . ? C8 C7 C6 127.6(2) . . ? C8 C7 H7 116.2 . . ? C6 C7 H7 116.2 . . ? C7 C8 C9 126.8(2) . . ? C7 C8 H8 116.6 . . ? C9 C8 H8 116.6 . . ? C14 C9 C10 117.50(19) . . ? C14 C9 C8 122.72(19) . . ? C10 C9 C8 119.77(19) . . ? C11 C10 C9 121.6(2) . . ? C11 C10 H10 119.2 . . ? C9 C10 H10 119.2 . . ? C12 C11 C10 119.4(2) . . ? C12 C11 H11 120.3 . . ? C10 C11 H11 120.3 . . ? C13 C12 C11 120.5(2) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C12 C13 C14 119.7(2) . . ? C12 C13 H13 120.1 . . ? C14 C13 H13 120.1 . . ? C13 C14 C9 121.16(19) . . ? C13 C14 N1 119.70(18) . . ? C9 C14 N1 119.13(17) . . ? O1 C15 N2 122.63(19) . . ? O1 C15 N1 120.83(19) . . ? N2 C15 N1 116.54(19) . . ? _diffrn_measured_fraction_theta_max 0.707 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.948 _refine_diff_density_max 0.512 _refine_diff_density_min -0.360 _refine_diff_density_rms 0.048 #--END