# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # 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_sad _audit_creation_date 2013-05-24T14:52:33-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #------------------ CHEMICAL INFORMATION ------------------------------------# _chemical_formula_moiety 'C34 H32 N2' _chemical_formula_sum 'C34 H32 N2' _chemical_formula_weight 468.62 #------------------ UNIT CELL INFORMATION -----------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 36.831(3) _cell_length_b 6.1181(4) _cell_length_c 12.2456(12) _cell_angle_alpha 90 _cell_angle_beta 99.224(7) _cell_angle_gamma 90 _cell_volume 2723.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2306 _cell_measurement_theta_min 3.98 _cell_measurement_theta_max 27.04 #------------------ CRYSTAL INFORMATION -------------------------------------# _exptl_crystal_description lozenge _exptl_crystal_colour colorless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.143 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1000 _exptl_absorpt_coefficient_mu 0.066 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.849 _exptl_absorpt_correction_T_max 0.997 _exptl_absorpt_process_details ; '(SADABS (Sheldrick, Bruker, 2008))' ; #------------------ DATA COLLECTION INFORMATION -----------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_probe x-ray _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 9 _diffrn_reflns_number 22778 _diffrn_reflns_av_R_equivalents 0.0829 _diffrn_reflns_limit_h_min -46 _diffrn_reflns_limit_h_max 46 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.98 _diffrn_reflns_theta_max 27.04 _diffrn_reflns_theta_full 27.04 _diffrn_measured_fraction_theta_max 0.983 _diffrn_measured_fraction_theta_full 0.983 _reflns_number_total 2941 _reflns_number_gt 1422 _reflns_threshold_expression >2sigma(I) #------------------ COMPUTER PROGRAMS USED ----------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs 1990-2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND 3.2g (Crystal Impact GbR 2005)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #------------------ REFINEMENT INFORMATION ----------------------------------# _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^)+(0.0601P)^2^+0.9632P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_number_reflns 2941 _refine_ls_number_parameters 227 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1565 _refine_ls_R_factor_gt 0.059 _refine_ls_wR_factor_gt 0.1181 _refine_ls_wR_factor_ref 0.1512 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _refine_ls_shift/su_max 0 _refine_diff_density_max 0.151 _refine_diff_density_min -0.148 #------------------ ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS --------# 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 0 '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' 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_group _atom_site_disorder_assembly C1 C 0.28634(7) 0.2068(6) 0.9192(2) 0.0840(9) Uani 1 d . . . C2 C 0.27330(7) -0.1282(5) 0.8452(3) 0.0798(8) Uani 1 d . . . C3 C 0.31251(6) 0.2438(5) 0.8534(2) 0.0657(7) Uani 1 d . . . C4 C 0.29872(6) -0.1058(5) 0.7757(2) 0.0654(7) Uani 1 d . . . C5 C 0.31931(5) 0.0844(4) 0.77893(16) 0.0526(6) Uani 1 d . . . C6 C 0.34703(6) 0.1152(4) 0.70974(17) 0.0567(6) Uani 1 d . . . C7 C 0.37072(6) 0.1415(4) 0.65439(16) 0.0541(6) Uani 1 d . . . C8 C 0.39739(5) 0.1690(3) 0.57847(15) 0.0460(5) Uani 1 d . . . C9 C 0.38013(6) 0.3117(4) 0.48020(19) 0.0553(6) Uani 1 d . . . C10 C 0.43300(6) 0.2798(5) 0.63401(17) 0.0549(6) Uani 1 d . . . C11 C 0.40712(7) -0.0551(4) 0.5340(2) 0.0559(6) Uani 1 d . . . C12 C 0.40606(6) 0.3308(5) 0.39486(19) 0.0581(6) Uani 1 d . . . C13 C 0.45899(7) 0.3142(5) 0.54936(18) 0.0584(6) Uani 1 d . . . C14 C 0.44265(5) 0.2150(3) 0.43673(15) 0.0452(5) Uani 1 d . . . C15 C 0.43483(8) -0.0281(4) 0.4544(2) 0.0576(6) Uani 1 d . . . C16 C 0.46804(6) 0.2353(4) 0.35649(16) 0.0513(6) Uani 1 d . . . C17 C 0.48826(5) 0.2421(4) 0.28893(15) 0.0507(6) Uani 1 d . . . N1 N 0.26661(6) 0.0235(5) 0.9172(2) 0.0895(8) Uani 1 d . . . H1 H 0.2811(7) 0.318(5) 0.970(2) 0.094(9) Uiso 1 d . . . H2 H 0.2591(7) -0.266(5) 0.841(2) 0.096(9) Uiso 1 d . . . H3 H 0.3253(6) 0.385(4) 0.8578(18) 0.079(8) Uiso 1 d . . . H4 H 0.3026(6) -0.219(4) 0.7260(18) 0.068(7) Uiso 1 d . . . H5 H 0.3555(6) 0.247(4) 0.4487(17) 0.076(7) Uiso 1 d . . . H6 H 0.3738(6) 0.459(4) 0.5080(17) 0.071(7) Uiso 1 d . . . H7 H 0.4262(6) 0.420(4) 0.6664(19) 0.084(8) Uiso 1 d . . . H8 H 0.4457(6) 0.182(4) 0.6971(17) 0.067(6) Uiso 1 d . . . H9 H 0.4172(6) -0.144(4) 0.5978(18) 0.068(7) Uiso 1 d . . . H10 H 0.3843(7) -0.128(4) 0.4982(18) 0.082(8) Uiso 1 d . . . H11 H 0.3951(6) 0.264(4) 0.323(2) 0.084(8) Uiso 1 d . . . H12 H 0.4101(7) 0.486(5) 0.381(2) 0.095(9) Uiso 1 d . . . H13 H 0.4629(6) 0.478(4) 0.5382(18) 0.082(8) Uiso 1 d . . . H14 H 0.4829(7) 0.248(4) 0.5763(18) 0.079(7) Uiso 1 d . . . H15 H 0.4576(7) -0.101(4) 0.483(2) 0.093(9) Uiso 1 d . . . H16 H 0.4243(6) -0.090(4) 0.384(2) 0.084(8) Uiso 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 0.0735(18) 0.103(2) 0.0831(18) -0.0193(18) 0.0355(15) -0.0027(17) C2 0.0558(16) 0.081(2) 0.107(2) 0.0001(18) 0.0265(15) -0.0128(15) C3 0.0545(14) 0.0755(19) 0.0700(15) -0.0102(14) 0.0190(12) -0.0077(14) C4 0.0513(13) 0.0723(19) 0.0753(16) -0.0075(15) 0.0184(12) -0.0055(13) C5 0.0369(11) 0.0707(16) 0.0505(12) 0.0030(12) 0.0079(9) 0.0020(11) C6 0.0480(12) 0.0667(16) 0.0560(13) 0.0031(12) 0.0102(11) 0.0027(11) C7 0.0474(12) 0.0604(15) 0.0552(12) 0.0020(11) 0.0109(11) 0.0010(11) C8 0.0431(11) 0.0505(13) 0.0462(11) 0.0006(10) 0.0132(9) -0.0013(10) C9 0.0499(14) 0.0587(16) 0.0576(14) 0.0063(12) 0.0098(11) 0.0077(12) C10 0.0503(13) 0.0704(17) 0.0449(12) -0.0055(13) 0.0108(10) -0.0058(12) C11 0.0596(15) 0.0461(15) 0.0646(15) 0.0034(12) 0.0183(12) -0.0002(12) C12 0.0611(15) 0.0613(17) 0.0526(14) 0.0097(13) 0.0109(11) 0.0054(12) C13 0.0530(15) 0.0776(19) 0.0464(12) -0.0092(12) 0.0134(11) -0.0120(14) C14 0.0479(12) 0.0492(13) 0.0402(10) -0.0012(9) 0.0125(9) -0.0017(10) C15 0.0673(16) 0.0488(15) 0.0613(15) -0.0020(12) 0.0235(13) -0.0003(12) C16 0.0566(13) 0.0534(15) 0.0453(11) -0.0022(10) 0.0124(11) -0.0035(11) C17 0.0536(12) 0.0567(15) 0.0425(11) -0.0012(10) 0.0099(9) -0.0005(11) N1 0.0696(15) 0.106(2) 0.1023(17) -0.0041(16) 0.0433(12) -0.0116(14) #------------------ MOLECULAR GEOMETRY --------------------------------------# _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 N1 1.334(4) . ? C1 C3 1.370(3) . ? C1 H1 0.96(3) . ? C2 N1 1.330(4) . ? C2 C4 1.369(3) . ? C2 H2 0.99(3) . ? C3 C5 1.386(3) . ? C3 H3 0.98(2) . ? C4 C5 1.386(3) . ? C4 H4 0.95(2) . ? C5 C6 1.440(3) . ? C6 C7 1.198(3) . ? C7 C8 1.467(3) . ? C8 C10 1.535(3) . ? C8 C11 1.539(3) . ? C8 C9 1.539(3) . ? C9 C12 1.529(3) . ? C9 H5 1.01(2) . ? C9 H6 1.01(2) . ? C10 C13 1.534(3) . ? C10 H7 0.99(3) . ? C10 H8 1.03(2) . ? C11 C15 1.529(3) . ? C11 H9 0.98(2) . ? C11 H10 0.99(2) . ? C12 C14 1.536(3) . ? C12 H11 1.00(2) . ? C12 H12 0.98(3) . ? C13 C14 1.539(3) . ? C13 H13 1.02(3) . ? C13 H14 0.98(2) . ? C14 C16 1.466(3) . ? C14 C15 1.537(3) . ? C15 H15 0.97(3) . ? C15 H16 0.96(3) . ? C16 C17 1.199(2) . ? C17 C17 1.386(4) 2_655 ? 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 N1 C1 C3 124.1(3) . . ? N1 C1 H1 116.0(15) . . ? C3 C1 H1 119.9(16) . . ? N1 C2 C4 124.0(3) . . ? N1 C2 H2 118.3(15) . . ? C4 C2 H2 117.7(15) . . ? C1 C3 C5 119.3(3) . . ? C1 C3 H3 119.3(13) . . ? C5 C3 H3 121.4(13) . . ? C2 C4 C5 119.5(3) . . ? C2 C4 H4 120.9(13) . . ? C5 C4 H4 119.6(13) . . ? C3 C5 C4 117.0(2) . . ? C3 C5 C6 121.0(2) . . ? C4 C5 C6 122.0(2) . . ? C7 C6 C5 178.4(2) . . ? C6 C7 C8 175.2(2) . . ? C7 C8 C10 112.42(16) . . ? C7 C8 C11 109.88(17) . . ? C10 C8 C11 108.64(18) . . ? C7 C8 C9 109.01(16) . . ? C10 C8 C9 108.20(19) . . ? C11 C8 C9 108.59(18) . . ? C12 C9 C8 110.65(17) . . ? C12 C9 H5 113.0(12) . . ? C8 C9 H5 108.2(13) . . ? C12 C9 H6 111.5(12) . . ? C8 C9 H6 109.6(12) . . ? H5 C9 H6 103.7(18) . . ? C13 C10 C8 110.04(17) . . ? C13 C10 H7 112.1(14) . . ? C8 C10 H7 107.8(14) . . ? C13 C10 H8 109.2(11) . . ? C8 C10 H8 109.3(12) . . ? H7 C10 H8 108.4(17) . . ? C15 C11 C8 110.28(18) . . ? C15 C11 H9 111.2(12) . . ? C8 C11 H9 107.2(12) . . ? C15 C11 H10 111.9(13) . . ? C8 C11 H10 109.3(13) . . ? H9 C11 H10 106.8(19) . . ? C9 C12 C14 110.32(18) . . ? C9 C12 H11 111.4(13) . . ? C14 C12 H11 108.3(14) . . ? C9 C12 H12 109.0(15) . . ? C14 C12 H12 110.8(15) . . ? H11 C12 H12 107(2) . . ? C10 C13 C14 110.77(18) . . ? C10 C13 H13 109.9(13) . . ? C14 C13 H13 108.0(13) . . ? C10 C13 H14 109.9(13) . . ? C14 C13 H14 109.9(13) . . ? H13 C13 H14 108(2) . . ? C16 C14 C12 110.92(16) . . ? C16 C14 C15 109.27(17) . . ? C12 C14 C15 108.62(19) . . ? C16 C14 C13 111.55(16) . . ? C12 C14 C13 108.27(19) . . ? C15 C14 C13 108.1(2) . . ? C11 C15 C14 110.69(18) . . ? C11 C15 H15 110.5(14) . . ? C14 C15 H15 109.0(15) . . ? C11 C15 H16 108.1(14) . . ? C14 C15 H16 108.2(15) . . ? H15 C15 H16 110(2) . . ? C17 C16 C14 176.8(2) . . ? C16 C17 C17 178.00(15) . 2_655 ? C2 N1 C1 116.2(2) . . ? _database_code_depnum_ccdc_archive 'CCDC 965633'