Light-driven molecular motors ter Wiel, Matthijs K. J.; Meetsma, A; van Delden, Richard A.; Feringa, B.L.

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1 University of Groningen Light-driven molecular motors ter Wiel, Matthijs K. J. Meetsma, A van Delden, Richard A. Feringa, B.L. Published in: Journal of the American Chemical Society DOI: /ja052201e IMPORTANT NOTE: You are advised to consult the publisher's version (publisher's PDF) if you wish to cite from it. Please check the document version below. Document Version Publisher's PDF, also known as Version of record Publication date: 2005 Link to publication in University of Groningen/UMCG research database Citation for published version (APA): ter Wiel, M. K. J., Meetsma, A., van Delden, R. A., & Feringa, B. (2005). Light-driven molecular motors: Stepwise thermal helix inversion during unidirectional rotation of sterically overcrowded biphenanthrylidenes. Journal of the American Chemical Society, 127(41), DOI: /ja052201e Copyright Other than for strictly personal use, it is not permitted to download or to forward/distribute the text or part of it without the consent of the author(s) and/or copyright holder(s), unless the work is under an open content license (like Creative Commons). Take-down policy If you believe that this document breaches copyright please contact us providing details, and we will remove access to the work immediately and investigate your claim. Downloaded from the University of Groningen/UMCG research database (Pure): For technical reasons the number of authors shown on this cover page is limited to 10 maximum. Download date:

2 # CIF-file generated for C34H36 CP820 #============================================================================== data_global #============================================================================== # 0. AUDIT DETAILS _audit_creation_date _audit_creation_method PLATON <TABLE ACC> option SHELXL97-2 & Manual Editing _audit_update_record? ' :55:13' # 1. SUBMISSION DETAILS _publ_contact_author_name # Name of author for correspondence Drs. A. Meetsma _publ_contact_author_address # Address of author for correspondence Crystal Structure Center, Inorganic Solid State Chemistry Laboratory Chemical Physics, Materials Science Center, Groningen University, Nijenborgh 4, NL-9747 AG Groningen, The Netherlands. _publ_contact_author_ A.Meetsma@rug.nl _publ_contact_author_fax ' ' _publ_contact_author_phone ' ' _publ_requested_journal 'J. Am. Chem. Soc.' # Publication choise FI FM FO CI CM CO _publ_requested_category? _publ_requested_coeditor_name? _publ_contact_letter # Include date of submission Date of submission : :36:13 Consider this CIF submission for deposition of the third X-ray structure of a manuscript to be submitted to : J. Am. Chem. Soc. (Our Compound_Identification_Code : CP820) # 2. PROCESSING SUMMARY (JOURNAL OFFICE ONLY) _journal_date_recd_electronic? _journal_date_to_coeditor? _journal_date_from_coeditor? _journal_date_accepted? _journal_date_printers_first?

3 _journal_date_printers_final? _journal_date_proofs_out? _journal_date_proofs_in? _journal_coeditor_name? _journal_coeditor_code? _journal_coeditor_notes? _journal_techeditor_code? _journal_techeditor_notes? _journal_coden_astm? _journal_name_full? _journal_year? _journal_volume? _journal_issue? _journal_page_first? _journal_page_last? _journal_suppl_publ_number? _journal_suppl_publ_pages? # 3. TITLE AND AUTHOR LIST _publ_section_title? _publ_section_title_footnote? # The loop structure below should contain the names and adresses of all # authors, in the required order of publication. Repeat as necessary. _publ_author_name _publ_author_footnote _publ_author_address 'Meetsma, Auke'? # author related footnote Crystal Structure Center, Inorganic Solid State Chemistry Laboratory Chemical Physics, Materials Science Center, Groningen University, Nijenborgh 4, NL-9747 AG Groningen, The Netherlands.

4 # 4. TEXT _publ_section_synopsis? _publ_section_abstract? # Insert blank lines between paragraphs _publ_section_comment? _publ_section_exptl_prep? _publ_section_exptl_refinement? # Insert blank lines between references _publ_section_references Altomare, A., Burla, M.C., Camalli, M., Cascarano, G.L., Giacovazzo, C. Guagliardi, A., Moliterni, A.G.G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, Boeyens, J.C.A. (1978). J.Cryst.Mol.Struct. 8, Bondi, A. (1964). J. Phys. Chem. 68, Bruker, (2000). SMART, SAINT, SADABS, XPREP and SHELXTL/NT. Software Reference Manual Bruker AXS Inc. Madison, Wisconsin, USA. International Tables for Crystallography (1983). Vol. A. Space-group symmetry, edited by T. Hahn. Dordrecht: Reidel. (Present distributor Kluwer Academic Publishers, Dordrecht). International Tables for Crystallography (1992). Vol. C. Edited by A.J.C Wilson, Kluwer Academic Publishers, Dordrecht, The Netherlands. Le Page, Y. (1987). J. Appl. Cryst. 20, Le Page, Y. (1988). J. Appl. Cryst. 21, Meetsma, A. (2003). Extended version of the program PLUTO. Groningen University, The Netherlands. (unpublished). Sheldrick, G.M. SHELXL97. Program for Crystal Structure Refinement. University of G\"ottingen, Germany, Sheldrick, G.M. SADABS. Version 2. Multi-Scan Absorption Correction Program. University of G\"ottingen, Germany, 2001 Spek, A.L. (1987). Acta Cryst. C43, Spek, A.L. (1988). J. Appl. Cryst. 21,

5 Spek, A.L. (1990). Acta Cryst. A46, C-34. Spek, A.L. (1994). Am. Crystallogr. Assoc.-Abstracts, 22, 66. _publ_section_figure_captions Fig. 1. Chemical structural diagram (scheme 1) of the title compound Fig. 2. Perspective PLUTO drawing of the molecule illustrating the configuration and the adopted numbering scheme. Fig. 3. Molecular packing viewed down unit cell axes. Fig. 4. Perspective ORTEP drawing of the title compound. Displacement ellipsoids for non-h are represented at the 50% probability level. The H-atoms are drawn with an arbitrary radius. # 5. CHEMICAL DATA _chemical_name_systematic? _chemical_name_common? _chemical_melting_point? _chemical_formula_moiety 'C34 H36' # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_structural? _chemical_formula_sum 'C34 H36' _chemical_formula_iupac? _chemical_formula_weight _chemical_compound_source 'see text' _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source H H 'International Tables Vol C Tables and ' C C 'International Tables Vol C Tables and ' # 6. CRYSTAL DATA _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_hall '-P 2ac 2ab' _symmetry_space_group_name_h-m 'P b c a' _symmetry_int_tables_number 61 _symmetry_equiv_pos_as_xyz x,y,z 1/2-x,-y,1/2+z 1/2+x,1/2-y,-z -x,1/2+y,1/2-z

6 -x,-y,-z 1/2+x,y,1/2-z 1/2-x,1/2+y,z x,1/2-y,1/2+z _cell_length_a (6) _cell_length_b (8) _cell_length_c (1) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume (4) _cell_formula_units_z 8 _cell_measurement_temperature 100(1) _cell_measurement_reflns_used 5489 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max _cell_special_details The final unit cell was obtained from the xyz centroids of 5489 reflections after integration using the SAINT software package (Bruker, 2000). _exptl_crystal_description 'platelet' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.07 _exptl_crystal_size_rad? _exptl_crystal_density_meas? _exptl_crystal_density_diffrn _exptl_crystal_density_method 'not measured' _exptl_crystal_f_ _exptl_absorpt_coefficient_mu _exptl_absorpt_correction_type 'Multi-Scan' _exptl_absorpt_process_details '(SADABS, Sheldrick, Bruker, 2000))' _exptl_absorpt_correction_t_min _exptl_absorpt_correction_t_max # 7. EXPERIMENTAL DATA _exptl_special_details? _diffrn_ambient_temperature 100(1) _diffrn_radiation_wavelength _diffrn_radiation_type 'MoK\a' _diffrn_radiation_source 'fine focus sealed Siemens Mo tube ' _diffrn_radiation_monochromator 'parallel mounted graphite' _diffrn_radiation_detector CCD area-detector _diffrn_measurement_device_type Bruker Smart Apex _diffrn_measurement_method 'phi and omega scans' _diffrn_special_details Crystal into the cold nitrogen stream of the low-temparature unit (KRYOFLEX, (Bruker, 2000)).

7 _diffrn_detector_area_resol_mean '4096x4096 / 62x62 (binned 512)' _diffrn_standards_number? _diffrn_standards_interval_count? _diffrn_standards_interval_time? _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l??? # number of measured reflections (redundant set) _diffrn_reflns_number _diffrn_reflns_av_r_equivalents _diffrn_reflns_av_sigmai/neti _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 2.26 _diffrn_reflns_theta_max _diffrn_measured_fraction_theta_max _diffrn_reflns_theta_full _diffrn_measured_fraction_theta_full _diffrn_reflns_reduction_process Intensity data were corrected for Lorentz and polarization effects, decay and absorption and reduced to F~o~^2^ using SAINT (Bruker, 2000) and SADABS (Sheldrick, 2001) # number of unique reflections _reflns_number_total 5539 _reflns_number_gt 3977 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART, Bruker Version 5.624, 2001' _computing_cell_refinement 'SAINT, Bruker Version 6.02A, 2000' _computing_data_reduction 'XPREP, Bruker Version 5.1/NT, 2000' _computing_structure_solution SIR-97 (Altomare et al., 1997) _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics PLUTO (Meetsma, 2003) PLATON (Spek, 1994) _computing_publication_material 'PLATON (Spek, 1990)' # 8. REFINEMENT DATA _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

8 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^)+(0.0397p)^2^ p] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary direct _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef? _refine_ls_abs_structure_details? _chemical_absolute_configuration? _refine_ls_abs_structure_flack? _refine_ls_number_reflns 5539 _refine_ls_number_parameters 451 _refine_ls_number_restraints 0 _refine_ls_number_constraints? _refine_ls_r_factor_all _refine_ls_r_factor_gt _refine_ls_wr_factor_ref _refine_ls_wr_factor_gt _refine_ls_goodness_of_fit_ref _refine_ls_restrained_s_all _refine_ls_shift/su_max _refine_ls_shift/su_mean _refine_diff_density_max _refine_diff_density_min _refine_diff_density_rms _vrn_publ_code_void_volume 0.0 _vrn_publ_code_frame_time_sec 10.0 _vrn_publ_code_meas_time_hour 8.0 # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_u_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags C1 C Uani (12) (9) (6) (4).. C2 C Uani (13) (9) (6) (5).. C3 C Uani (14) (11) (8) (6).. C4 C Uani (14) (11) (7) (5).. C5 C Uani (12) (9) (6) (5).. C6 C Uani (13) (9) (7) (5).. C7 C Uani (14) (10) (7) (5)..

9 C8 C Uani (12) (9) (6) (5).. C9 C Uani (14) (10) (6) (5).. C10 C Uani (14) (10) (6) (5).. C11 C Uani (14) (10) (6) (5).. C12 C Uani (13) (9) (6) (5).. C13 C Uani (13) (9) (6) (5).. C14 C Uani (12) (9) (6) (4).. C15 C Uani (15) (10) (7) (5).. C16 C Uani (15) (11) (7) (5).. C17 C Uani (18) (14) (7) (6).. C18 C Uani (12) (9) (6) (4).. C19 C Uani (13) (9) (6) (5).. C20 C Uani (14) (10) (6) (5).. C21 C Uani (14) (10) (6) (5).. C22 C Uani (13) (9) (6) (5).. C23 C Uani (15) (10) (6) (5).. C24 C Uani (15) (10) (6) (5).. C25 C Uani (13) (9) (6) (5).. C26 C Uani (14) (10) (7) (5).. C27 C Uani (14) (10) (6) (5).. C28 C Uani (13) (10) (7) (5).. C29 C Uani (13) (9) (6) (5).. C30 C Uani (13) (9) (6) (4).. C31 C Uani (13) (9) (6) (4).. C32 C Uani (14) (10) (6) (5).. C33 C Uani (15) (11) (7) (5).. C34 C Uani (15) (13) (8) (6).. H2 H Uiso (3) (13).. H3 H Uiso (4) (16).. H3' H Uiso (3) (16).. H4 H Uiso (3) (14).. H4' H Uiso (3) (14).. H6 H Uiso (3) (14).. H7 H Uiso (3) (14).. H9 H Uiso (3) (14).. H11 H Uiso (3) (13).. H12 H Uiso (3) (14).. H15 H Uiso (3) (15).. H15' H Uiso (3) (15).. H16 H Uiso (3) (16).. H16' H Uiso (3) (16).. H16" H Uiso (3) (16).. H17 H Uiso (4) (19).. H17' H Uiso (4) (18).. H17" H Uiso (4) 0.072(2).. H19 H Uiso (3) (13).. H20 H Uiso (3) (14).. H20' H Uiso (3) (15).. H21 H Uiso (3) (14).. H21' H Uiso (3) (13).. H23 H Uiso (3) (14).. H24 H Uiso (3) (14).. H26 H Uiso (3) (14).. H28 H Uiso (3) (13).. H29 H Uiso (3) (13).. H32 H Uiso (3) (15).. H32' H Uiso (3) (14).. H33 H Uiso (3) (15).. H33' H Uiso (3) (15).. H33" H Uiso (3) (15).. H34 H Uiso (4) (18).. H34' H Uiso (4) (16).. H34" H Uiso (3) (17).. _atom_site_aniso_label

10 _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 C (7) (8) (7) (6) (6) (6) C (8) (8) (8) (6) (6) (6) C (9) (10) (10) (9) (8) (7) C (8) (9) (9) (7) (7) (7) C (8) (8) (8) (6) (6) (6) C (8) (8) (9) (7) (7) (6) C (8) (8) (9) (7) (7) (6) C (8) (8) (8) (6) (6) (6) C (9) (8) (9) (7) (7) (7) C (9) (9) (8) (7) (7) (7) C (8) (8) (8) (7) (7) (7) C (8) (8) (8) (7) (7) (6) C (8) (8) (8) (6) (6) (6) C (8) (7) (8) (6) (6) (6) C (9) (9) (9) (7) (7) (7) C (9) (9) (10) (8) (8) (7) C (11) (12) (9) (9) (8) (9) C (7) (8) (7) (6) (6) (6) C (8) (8) (8) (6) (6) (6) C (9) (9) (9) (7) (7) (7) C (8) (9) (9) (7) (7) (7) C (8) (8) (8) (6) (6) (6) C (9) (9) (8) (7) (7) (7) C (9) (9) (8) (7) (7) (7) C (8) (8) (8) (6) (7) (7) C (9) (9) (9) (7) (7) (7) C (9) (8) (9) (7) (7) (7) C (9) (9) (9) (7) (7) (7) C (8) (8) (8) (7) (6) (6) C (8) (7) (7) (6) (6) (6) C (8) (7) (7) (6) (6) (6) C (9) (8) (8) (7) (7) (7) C (9) (10) (9) (8) (7) (8) C (10) (12) (11) (9) (8) (8) # 10. MOLECULAR GEOMETRY _geom_special_details Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All esds are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C (2).. no C1 C (2).. no C1 C (2).. no C2 C (2).. no C2 C (2).. no

11 C3 C (2).. no C4 C (2).. no C5 C (2).. no C5 C (2).. no C6 C (3).. no C7 C (2).. no C8 C (2).. no C8 C (2).. no C9 C (2).. no C10 C (2).. no C10 C (2).. no C11 C (2).. no C12 C (2).. no C13 C (2).. no C15 C (2).. no C18 C (2).. no C18 C (2).. no C19 C (2).. no C19 C (2).. no C20 C (2).. no C21 C (2).. no C22 C (2).. no C22 C (2).. no C23 C (3).. no C24 C (2).. no C25 C (2).. no C25 C (2).. no C26 C (2).. no C27 C (2).. no C27 C (2).. no C28 C (2).. no C29 C (2).. no C30 C (2).. no C32 C (2).. no C2 H no C3 H no C3 H3' no C4 H no C4 H4' no C6 H no C7 H no C9 H no C11 H no C12 H no C15 H no C15 H15' no C16 H no C16 H16' no C16 H16" no C17 H no C17 H17' no C17 H17" no C19 H no C20 H no C20 H20' no C21 H no C21 H21' no C23 H no C24 H no C26 H no C28 H no C29 H no C32 H no C32 H32' no C33 H no C33 H33' no

12 C33 H33" no C34 H no C34 H34' no C34 H34" no _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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C (12)... no C2 C1 C (13)... no C14 C1 C (14)... no C1 C2 C (13)... no C1 C2 C (13)... no C3 C2 C (13)... no C2 C3 C (15)... no C3 C4 C (14)... no C4 C5 C (14)... no C4 C5 C (13)... no C6 C5 C (14)... no C5 C6 C (15)... no C6 C7 C (15)... no C7 C8 C (14)... no C7 C8 C (14)... no C9 C8 C (14)... no C8 C9 C (15)... no C9 C10 C (14)... no C9 C10 C (15)... no C11 C10 C (15)... no C10 C11 C (15)... no C11 C12 C (14)... no C8 C13 C (14)... no C8 C13 C (13)... no C12 C13 C (14)... no C1 C14 C (13)... no C1 C14 C (13)... no C5 C14 C (14)... no C2 C15 C (14)... no C1 C18 C (13)... no C1 C18 C (14)... no C19 C18 C (12)... no C18 C19 C (12)... no C18 C19 C (13)... no C20 C19 C (12)... no C19 C20 C (13)... no C20 C21 C (13)... no C21 C22 C (14)... no C21 C22 C (14)... no C23 C22 C (15)... no C22 C23 C (15)... no C23 C24 C (15)... no C24 C25 C (14)... no C24 C25 C (14)... no C26 C25 C (14)... no C25 C26 C (15)... no C26 C27 C (15)... no C26 C27 C (15)... no C28 C27 C (15)... no C27 C28 C (15)... no C28 C29 C (14)... no C25 C30 C (14)... no

13 C25 C30 C (14)... no C29 C30 C (14)... no C18 C31 C (13)... no C18 C31 C (13)... no C22 C31 C (14)... no C19 C32 C (14)... no C1 C2 H no C3 C2 H no C15 C2 H no C2 C3 H no C2 C3 H3' no C4 C3 H no C4 C3 H3' no H3 C3 H3' no C3 C4 H no C3 C4 H4' no C5 C4 H no C5 C4 H4' no H4 C4 H4' no C5 C6 H no C7 C6 H no C6 C7 H no C8 C7 H no C8 C9 H no C10 C9 H no C10 C11 H no C12 C11 H no C11 C12 H no C13 C12 H no C2 C15 H no C2 C15 H15' no C16 C15 H no C16 C15 H15' no H15 C15 H15' no C15 C16 H no C15 C16 H16' no C15 C16 H16" no H16 C16 H16' no H16 C16 H16" no H16' C16 H16" no C10 C17 H no C10 C17 H17' no C10 C17 H17" no H17 C17 H17' no H17 C17 H17" no H17' C17 H17" no C18 C19 H no C20 C19 H no C32 C19 H no C19 C20 H no C19 C20 H20' no C21 C20 H no C21 C20 H20' no H20 C20 H20' no C20 C21 H no C20 C21 H21' no C22 C21 H no C22 C21 H21' no H21 C21 H21' no C22 C23 H no C24 C23 H no C23 C24 H no C25 C24 H no C25 C26 H no C27 C26 H no C27 C28 H no

14 C29 C28 H no C28 C29 H no C30 C29 H no C19 C32 H no C19 C32 H32' no C33 C32 H no C33 C32 H32' no H32 C32 H32' no C32 C33 H no C32 C33 H33' no C32 C33 H33" no H33 C33 H33' no H33 C33 H33" no H33' C33 H33" no C27 C34 H no C27 C34 H34' no C27 C34 H34" no H34 C34 H34' no H34 C34 H34" no H34' C34 H34" no _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 C14 C1 C2 C (18).... no C14 C1 C2 C (15).... no C18 C1 C2 C (15).... no C18 C1 C2 C (17).... no C2 C1 C14 C (18).... no C2 C1 C14 C (15).... no C18 C1 C14 C (16).... no C18 C1 C14 C (2).... no C2 C1 C18 C19 4.5(2).... no C2 C1 C18 C (14).... no C14 C1 C18 C (14).... no C14 C1 C18 C31-1.7(2).... no C1 C2 C3 C4-15.1(2).... no C15 C2 C3 C (15).... no C1 C2 C15 C (13).... no C3 C2 C15 C (19).... no C2 C3 C4 C (19).... no C3 C4 C5 C (16).... no C3 C4 C5 C (19).... no C4 C5 C6 C (15).... no C14 C5 C6 C7 0.5(2).... no C4 C5 C14 C1-5.2(2).... no C4 C5 C14 C (14).... no C6 C5 C14 C (13).... no C6 C5 C14 C13-4.6(2).... no C5 C6 C7 C8 2.8(2).... no C6 C7 C8 C (15).... no C6 C7 C8 C13-1.9(2).... no C7 C8 C9 C (16).... no C13 C8 C9 C10 1.3(2).... no C7 C8 C13 C (14).... no C7 C8 C13 C14-2.3(2).... no C9 C8 C13 C12-2.2(2).... no C9 C8 C13 C (14).... no

15 C8 C9 C10 C11 0.0(2).... no C8 C9 C10 C (17).... no C9 C10 C11 C12-0.4(2).... no C17 C10 C11 C (17).... no C10 C11 C12 C13-0.6(2).... no C11 C12 C13 C8 1.9(2).... no C11 C12 C13 C (15).... no C8 C13 C14 C (14).... no C8 C13 C14 C5 5.5(2).... no C12 C13 C14 C1 6.2(2).... no C12 C13 C14 C (14).... no C1 C18 C19 C (15).... no C1 C18 C19 C (17).... no C31 C18 C19 C (17).... no C31 C18 C19 C (16).... no C1 C18 C31 C (16).... no C1 C18 C31 C (2).... no C19 C18 C31 C (18).... no C19 C18 C31 C (15).... no C18 C19 C20 C (18).... no C32 C19 C20 C (14).... no C18 C19 C32 C (17).... no C20 C19 C32 C (13).... no C19 C20 C21 C (17).... no C20 C21 C22 C (16).... no C20 C21 C22 C (19).... no C21 C22 C23 C (15).... no C31 C22 C23 C24-0.3(2).... no C21 C22 C31 C18-3.5(2).... no C21 C22 C31 C (14).... no C23 C22 C31 C (14).... no C23 C22 C31 C30-3.3(2).... no C22 C23 C24 C25 2.6(2).... no C23 C24 C25 C (16).... no C23 C24 C25 C30-1.3(2).... no C24 C25 C26 C (16).... no C30 C25 C26 C27 1.4(2).... no C24 C25 C30 C (14).... no C24 C25 C30 C31-2.2(2).... no C26 C25 C30 C29-2.2(2).... no C26 C25 C30 C (14).... no C25 C26 C27 C28 0.3(2).... no C25 C26 C27 C (16).... no C26 C27 C28 C29-1.3(2).... no C34 C27 C28 C (16).... no C27 C28 C29 C30 0.5(2).... no C28 C29 C30 C25 1.3(2).... no C28 C29 C30 C (15).... no C25 C30 C31 C (14).... no C25 C30 C31 C22 4.4(2).... no C29 C30 C31 C18 6.2(2).... no C29 C30 C31 C (15).... no _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag C1 C (2).. no C1 C (2).. no C2 C (2).. no C5 C (2).. no C7 C (2). 6_455 no C11 C (2). 6_555 no

16 C12 C (2).. no C12 C (2).. no C12 C (2).. no C12 C (2).. no C13 C (2).. no C13 C (2).. no C14 C (2).. no C14 C (2).. no C18 C (2).. no C22 C (2).. no C29 C (2).. no C29 C (2).. no C29 C (2).. no C30 C (2).. no C30 C (2).. no C30 C (2).. no C31 C (2).. no C31 C (2).. no C33 C (2).. no C33 C (2).. no C1 H4' no C1 H no C1 H no C1 H no C2 H no C2 H no C3 H16" no C4 H _455 no C4 H no C5 H no C7 H _455 no C7 H _555 no C8 H _555 no C9 H _555 no C11 H34" _555 no C11 H _555 no C14 H15' no C14 H no C14 H no C15 H no C16 H no C18 H no C18 H21' no C18 H no C18 H no C19 H no C19 H _555 no C21 H no C22 H no C24 H15' _545 no C25 H15' _545 no C27 H16' _545 no C28 H16' _545 no C29 H _455 no C31 H no C31 H no C32 H _555 no C33 H no C34 H33' _555 no H2 C no H2 C no H2 H no H2 H no H2 H no H2 H33" no H3 C no

17 H3 C no H3 H15' no H3 H16" no H3 H _555 no H3 H _555 no H4 H no H4 C _455 no H4 C _455 no H4 H _455 no H4 H32' _455 no H4 H _555 no H4' C no H4' H no H6 H no H6 H33" _455 no H7 H no H7 H _555 no H7 C _455 no H9 H no H9 H no H11 H17' no H11 C _555 no H12 C no H12 C no H12 C no H12 C no H12 C no H12 H21' no H15 H _555 no H15' C no H15' H no H15' C _555 no H15' C _555 no H16 H no H16 C _555 no H16 H _555 no H16' H33' _555 no H16' C _555 no H16' C _555 no H16" C no H16" H no H16" H _555 no H17 H no H17 H _455 no H17' H no H17' H33" _555 no H19 C no H19 C no H19 H no H19 H33" no H19 C _555 no H19 H _555 no H20 H no H20 H32' no H20 H _545 no H20 H _545 no H21 H no H21' C no H21' H no H23 H no H23 H _555 no H23 C _545 no H23 C _545 no H24 H no H24 H _545 no H26 H no

18 H26 H no H26 C _545 no H26 H _455 no H28 H34' no H29 C no H29 C no H29 C no H29 C no H29 C no H29 H4' no H29 H _455 no H32 C no H32 H no H32 H _545 no H32 H16" _545 no H32' H no H32' H _555 no H33 C no H33 C no H33 C no H33 H no H33' H16' _455 no H33' C _555 no H33' H34' _555 no H33" H no H33" H no H33" H _555 no H33" H17' _554 no H34 H no H34' H no H34' H33' _555 no H34" C _455 no #===END of Crystallographic Information File