Supplementary Material (ESI) for Photochemical & Photobiological Sciences This journal is © The Royal Society of Chemistry and Owner Societies 2003 data_global _publ_contact_author_email d.bassani@lcoo.u-bordeaux1.fr _publ_contact_author_name 'Dario M. Bassani' _journal_name_full Photochem.Photobiol.Sci. _journal_coden_cambridge 0171 _journal_coden_ASTM ? _journal_coeditor_code ? _journal_coeditor_name ? _journal_coeditor_notes ; ? ; _journal_date_accepted ? _journal_date_from_coeditor ? _journal_date_printers_final ? _journal_date_printers_first ? _journal_date_proofs_in ? _journal_date_proofs_out ? _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? _journal_techeditor_code ? _journal_techeditor_notes ; ? ; _journal_volume ? _journal_year ? _publ_contact_author_address ; Groupe de Chimie Supramoleculaire, Biomimetisme et Nanosciences, LCOO UMR 5802 Universite Bordeaux I, 33405 Talence, France ; _publ_contact_author_fax ? _publ_contact_author_phone ? _publ_contact_letter ; ; _publ_requested_category CO _publ_requested_coeditor_name ? _publ_section_title ; Supramolecular Control of [2+2] Photodimerization via Hydrogen-Bonding ; # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_address _publ_author_footnote 'Vincent Darcos' ; Groupe de Chimie Supramoleculaire, Biomimetisme et Nanosciences, LCOO UMR 5802 Universite Bordeaux I, 33405 Talence, France ; ; ? #footnote for author 1 ; 'Kirsten Griffith ' ; Groupe de Chimie Supramoleculaire, Biomimetisme et Nanosciences, LCOO UMR 5802 Universite Bordeaux I, 33405 Talence, France ; ; ? # footnote 2 ; 'Xavier Sallenave' ; Groupe de Chimie Supramoleculaire, Biomimetisme et Nanosciences, LCOO UMR 5802 Universite Bordeaux I, 33405 Talence, France ; ; ? # footnote 2 ; 'Jean-Pierre Desvergne' ; Groupe de Chimie Supramoleculaire, Biomimetisme et Nanosciences, LCOO UMR 5802 Universite Bordeaux I, 33405 Talence, France ; ; ? # footnote 2 ; ; C.Guyard-Duhayon ; ; Laboratoire de Chimie Inorganique et Materiaux Moleculaires, Universite Pierre et Marie Curie, bat F, Case 42 4 place Jussieu 75252 Paris France ; ; ? # footnote 2 ; 'Bernold Hasenknopf' ; Laboratoire de Chimie Inorganique et Materiaux Moleculaires, Universite Pierre et Marie Curie, bat F, Case 42 4 place Jussieu 75252 Paris France ; ; ? # footnote 2 ; 'Dario M. Bassani' ; Groupe de Chimie Supramoleculaire, Biomimetisme et Nanosciences, LCOO UMR 5802 Universite Bordeaux I, 33405 Talence, France ; ; ? # footnote 2 ; data_CRYSTALS_cif _database_code_CSD 213543 _audit_creation_date 03-23-06 #============================================================================== # 4. TEXT _publ_section_abstract #Text of the abstract ; ? ; _publ_section_comment #Text of the paper ; ? ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions #Captions to figures ; ? ; _publ_section_exptl_refinement # see also _refine_ls_hydrogen for refinement keywords. ; H atoms were introduced in calculated positions ; _publ_section_exptl_prep ; poor quality cristal ; #========================================================================== _chemical_name_systematic # IUPAC name, in full ; ? ; _chemical_melting_point ? # choose from 'full, fullcycle, atomblock, userblock, diagonal, sparse' _refine_ls_matrix_type full # choose from 'heavy, direct, difmap, geom' _atom_sites_solution_primary direct # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom # choose from 'none, undef, noref, refall, refxyz, refU, constr, mixed' _refine_ls_hydrogen_treatment refU #**************************************************************************** # General computing #============================================================= _computing_structure_refinement ; CRYSTALS (Watkin et al 2001) ; _computing_publication_material ; CRYSTALS (Watkin et al 2001) ; _computing_molecular_graphics ; CAMERON (Watkin et al 1996) ; #============================================================= _cell_length_a 11.154(4) _cell_angle_alpha 73.76(4) _cell_length_b 12.559(2) _cell_angle_beta 74.41(6) _cell_length_c 14.720(13) _cell_angle_gamma 82.10(2) _cell_volume 1903(2) _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1 ' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z # choose from: rm (reference molecule of # known chirality), ad (anomolous # dispersion - ie. Flack param), rmad # (both rm and ad), syn (known from # synthetic pathway), unk (unknown) # or . (not applicable). _chemical_absolute_configuration . loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 International_Tables_Vol_IV_Table_2.2B 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 International_Tables_Vol_IV_Table_2.2B 'N ' 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 International_Tables_Vol_IV_Table_2.2B 'O ' 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 International_Tables_Vol_IV_Table_2.2B _cell_formula_units_Z 2 _chemical_formula_sum ' C34 H46 N7 O8 ' _chemical_formula_moiety ' (C8 H12 N2 O3) (C26 H30 N5 O3) (H4 O2)' _chemical_compound_source ; ? ; _chemical_formula_weight 680.78 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 11.94 _cell_measurement_theta_max 12.19 _cell_measurement_temperature 295 _exptl_crystal_description ' block ' _exptl_crystal_colour ' colourless ' _exptl_crystal_size_min 0.25 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_max 0.45 _exptl_crystal_density_diffrn 1.19 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 712.000 _exptl_absorpt_coefficient_mu 0.086 _diffrn_measurement_device_type ; Enraf-nonius Cad-4 ; _diffrn_radiation_monochromator graphite _computing_data_collection ; DATA COLLECTION ; _computing_data_reduction ; USER DEFINED 5 ; _computing_cell_refinement ; USER DEFINED 6 ; _computing_structure_solution ; USER DEFINED STRUCTURE SOLUTION ; _diffrn_measurement_method \w/2\q _exptl_absorpt_correction_type refdelf _exptl_absorpt_process_details ; DIFABS (Walker & Stuart, 1983) ; _exptl_absorpt_correction_T_min 0.80 _exptl_absorpt_correction_T_max 0.99 _diffrn_standards_interval_time '3600 ' _diffrn_standards_number 2 _diffrn_standards_decay_% 19.81 _diffrn_ambient_temperature 295 _diffrn_reflns_number 7056 _reflns_number_total 6679 _diffrn_reflns_av_R_equivalents 0.03 # Number of reflections with Friedels Law is 6679 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 6669 _diffrn_reflns_theta_min 1.485 _diffrn_reflns_theta_max 24.972 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.972 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _reflns_limit_h_min -12 _reflns_limit_h_max 13 _reflns_limit_k_min -14 _reflns_limit_k_max 14 _reflns_limit_l_min 0 _reflns_limit_l_max 17 _refine_diff_density_min -0.35 _refine_diff_density_max 1.86 _refine_ls_number_reflns 2689 _refine_ls_number_parameters 461 #_refine_ls_R_factor_ref 0.1391 _refine_ls_wR_factor_ref 0.1461 _refine_ls_goodness_of_fit_ref 0.9413 #_reflns_number_all 6679 _refine_ls_R_factor_all 0.2604 _refine_ls_wR_factor_all 0.2282 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>1.80u(I) _reflns_number_gt 2689 _refine_ls_R_factor_gt 0.1391 _refine_ls_wR_factor_gt 0.1461 _refine_ls_shift/su_max 0.001042 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method = Prince modified Chebychev polynomial, (Watkin, 1994) W = [weight] * [1-(deltaF/6*sigmaF)^2]^2 4.08 3.33 2.42 ; _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 ## -------------------REFERENCES ----------------------## ## Insert your own references - in alphabetic order _publ_section_references ; User-defined structure solution reference User-defined data collection reference Spare 5 Spare 6 Walker, N., and Stuart, D. Acta Cryst, (1983) A39, 158-166 Watkin D.J. (1994), Acta Cryst, A50, 411-437 Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin, D.J., Prout, C.K., Carruthers, J.R., Betteridge, P.W. & Cooper R.I. (2001) CRYSTALS Issue 11. Chemical Crystallography Laboratory, OXFORD, UK. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996) CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 # Replace trailing . with the number of unfound # hydrogen atoms attaced to relavent atom 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_occupancy _atom_site_adp_type _atom_site_attached_hydrogens C1 C -0.3869(13) 0.0701(11) 1.1993(12) 0.1056 1.0000 Uani . C2 C -0.2447(12) 0.190(1) 1.1956(11) 0.0771 1.0000 Uani . C3 C -0.1365(11) 0.2486(9) 1.1387(8) 0.0707 1.0000 Uani . C4 C -0.0829(11) 0.3124(9) 1.1704(8) 0.0690 1.0000 Uani . C5 C 0.030(1) 0.3717(8) 1.1187(8) 0.0613 1.0000 Uani . C6 C 0.0767(11) 0.433(1) 1.1636(8) 0.0725 1.0000 Uani . C7 C 0.180(1) 0.4906(9) 1.1199(7) 0.0672 1.0000 Uani . C8 C 0.2402(9) 0.4919(7) 1.0247(7) 0.0484 1.0000 Uani . C9 C 0.1938(9) 0.4324(8) 0.9782(7) 0.0593 1.0000 Uani . C10 C 0.0901(11) 0.3729(9) 1.0270(8) 0.0648 1.0000 Uani . C11 C 0.4095(9) 0.6206(8) 0.9907(7) 0.0454 1.0000 Uani . C12 C 0.4469(9) 0.7028(8) 1.0934(6) 0.0488 1.0000 Uani . C13 C 0.481(1) 0.7953(8) 1.2052(7) 0.0579 1.0000 Uani . C14 C 0.3947(13) 0.8188(12) 1.2960(9) 0.0966 1.0000 Uani . C15 C 0.6087(12) 0.752(1) 1.2168(9) 0.0798 1.0000 Uani . C16 C 0.5576(8) 0.7397(7) 0.9414(6) 0.0435 1.0000 Uani . C17 C 0.7230(8) 0.8760(7) 0.8630(6) 0.0454 1.0000 Uani . C18 C 0.7041(11) 0.938(1) 0.9316(8) 0.0762 1.0000 Uani . C19 C 0.7818(12) 1.0209(9) 0.9149(8) 0.0751 1.0000 Uani . C20 C 0.881(1) 1.0449(8) 0.8355(7) 0.0567 1.0000 Uani . C21 C 0.8956(11) 0.984(1) 0.7697(8) 0.0739 1.0000 Uani . C22 C 0.820(1) 0.9004(9) 0.7828(8) 0.0672 1.0000 Uani . C23 C 0.9643(11) 1.136(1) 0.8193(9) 0.0710 1.0000 Uani . C24 C 0.938(3) 1.234(2) 0.727(2) 0.0931 0.5000 Uani . C25 C 0.943(3) 1.187(3) 0.905(2) 0.0839 0.5000 Uani . C26 C 1.095(3) 1.099(3) 0.793(3) 0.0838 0.5000 Uani . C27 C 1.071(4) 1.151(3) 0.734(3) 0.1159 0.5000 Uani . C28 C 0.901(3) 1.228(3) 0.846(3) 0.1039 0.5000 Uani . C29 C 1.049(3) 1.098(3) 0.900(2) 0.0979 0.5000 Uani . C101 C 0.6042(11) 0.5967(9) 0.5369(7) 0.0653 1.0000 Uani . C102 C 0.4835(11) 0.5661(8) 0.7053(7) 0.0563 1.0000 Uani . C103 C 0.659(1) 0.6809(9) 0.6579(7) 0.0579 1.0000 Uani . C104 C 0.690(1) 0.6653(9) 0.5549(7) 0.0595 1.0000 Uani . C105 C 0.6873(17) 0.7811(12) 0.4851(8) 0.0978 1.0000 Uani . C106 C 0.564(2) 0.8482(15) 0.4989(14) 0.1402 1.0000 Uani . C107 C 0.8225(12) 0.6068(13) 0.537(1) 0.0912 1.0000 Uani . C108 C 0.8366(16) 0.4971(17) 0.6022(13) 0.1278 1.0000 Uani . N1 N 0.3457(7) 0.5508(6) 0.9686(5) 0.0485 1.0000 Uani . N2 N 0.4986(7) 0.6682(6) 0.9195(5) 0.0459 1.0000 Uani . N3 N 0.3841(7) 0.6292(6) 1.0809(5) 0.0490 1.0000 Uani . N4 N 0.5371(7) 0.7601(6) 1.0271(5) 0.0506 1.0000 Uani . N5 N 0.6508(7) 0.7907(6) 0.8677(5) 0.0501 1.0000 Uani . N101 N 0.5066(9) 0.5559(7) 0.6129(6) 0.0652 1.0000 Uani . N102 N 0.5593(8) 0.6303(7) 0.7232(5) 0.0572 1.0000 Uani . O1 O -0.2840(8) 0.1343(7) 1.1481(7) 0.0909 1.0000 Uani . O2 O -0.298(1) 0.1936(9) 1.2786(8) 0.1198 1.0000 Uani . O3 O 0.4224(6) 0.7112(6) 1.1836(4) 0.0618 1.0000 Uani . O101 O 0.6180(8) 0.5796(7) 0.4588(5) 0.0884 1.0000 Uani . O102 O 0.3922(7) 0.5292(6) 0.7675(5) 0.0713 1.0000 Uani . O103 O 0.7177(7) 0.7377(7) 0.6804(5) 0.0751 1.0000 Uani . O200 O 0.8302(15) 0.2971(13) 0.4544(11) 0.182(6) 1.0000 Uiso . O300 O 0.1913(14) 0.9591(12) 0.4836(11) 0.177(5) 1.0000 Uiso . H11 H -0.4101 0.0314 1.1557 0.170(12) 1.0000 Uiso . H12 H -0.3685 0.0132 1.2575 0.170(12) 1.0000 Uiso . H13 H -0.4624 0.1196 1.2227 0.170(12) 1.0000 Uiso . H31 H -0.1005 0.2395 1.0699 0.170(12) 1.0000 Uiso . H41 H -0.1244 0.3222 1.2377 0.170(12) 1.0000 Uiso . H61 H 0.0308 0.4373 1.2317 0.170(12) 1.0000 Uiso . H71 H 0.2131 0.5325 1.1565 0.170(12) 1.0000 Uiso . H91 H 0.2367 0.4319 0.9087 0.170(12) 1.0000 Uiso . H101 H 0.0601 0.3265 0.9920 0.170(12) 1.0000 Uiso . H131 H 0.4938 0.8659 1.1513 0.170(12) 1.0000 Uiso . H141 H 0.3109 0.8474 1.2845 0.170(12) 1.0000 Uiso . H142 H 0.4297 0.8751 1.3171 0.170(12) 1.0000 Uiso . H143 H 0.3860 0.7482 1.3503 0.170(12) 1.0000 Uiso . H150 H 0.6501 0.8098 1.2306 0.170(12) 1.0000 Uiso . H151 H 0.6037 0.6836 1.2716 0.170(12) 1.0000 Uiso . H152 H 0.6605 0.7336 1.1549 0.170(12) 1.0000 Uiso . H181 H 0.6344 0.9213 0.9925 0.170(12) 1.0000 Uiso . H191 H 0.7655 1.0662 0.9645 0.170(12) 1.0000 Uiso . H211 H 0.9662 1.0002 0.7092 0.170(12) 1.0000 Uiso . H221 H 0.8374 0.8557 0.7328 0.170(12) 1.0000 Uiso . H240 H 0.9891 1.2980 0.7141 0.170(12) 0.5000 Uiso . H241 H 0.8457 1.2625 0.7418 0.170(12) 0.5000 Uiso . H242 H 0.9548 1.2056 0.6677 0.170(12) 0.5000 Uiso . H250 H 1.0007 1.2481 0.8882 0.170(12) 0.5000 Uiso . H251 H 0.9579 1.1295 0.9636 0.170(12) 0.5000 Uiso . H252 H 0.8543 1.2201 0.9204 0.170(12) 0.5000 Uiso . H260 H 1.1509 1.1597 0.7806 0.170(12) 0.5000 Uiso . H261 H 1.1175 1.0337 0.8441 0.170(12) 0.5000 Uiso . H262 H 1.1135 1.0734 0.7294 0.170(12) 0.5000 Uiso . H270 H 1.1198 1.2151 0.7295 0.170(12) 0.5000 Uiso . H271 H 1.1292 1.0822 0.7368 0.170(12) 0.5000 Uiso . H272 H 1.0421 1.1677 0.6713 0.170(12) 0.5000 Uiso . H280 H 0.9578 1.2873 0.8330 0.170(12) 0.5000 Uiso . H281 H 0.8550 1.2087 0.9160 0.170(12) 0.5000 Uiso . H282 H 0.8357 1.2585 0.8055 0.170(12) 0.5000 Uiso . H290 H 1.1063 1.1578 0.8914 0.170(12) 0.5000 Uiso . H291 H 0.9954 1.0831 0.9684 0.170(12) 0.5000 Uiso . H292 H 1.1030 1.0280 0.8920 0.170(12) 0.5000 Uiso . H1051 H 0.7523 0.8245 0.4928 0.170(12) 1.0000 Uiso . H1052 H 0.7129 0.7724 0.4158 0.170(12) 1.0000 Uiso . H1061 H 0.5668 0.9243 0.4502 0.170(12) 1.0000 Uiso . H1062 H 0.5348 0.8611 0.5662 0.170(12) 1.0000 Uiso . H1063 H 0.4953 0.8091 0.4893 0.170(12) 1.0000 Uiso . H1071 H 0.8822 0.6562 0.5451 0.170(12) 1.0000 Uiso . H1072 H 0.8488 0.6010 0.4674 0.170(12) 1.0000 Uiso . H1081 H 0.9234 0.4621 0.5878 0.170(12) 1.0000 Uiso . H1082 H 0.8118 0.4997 0.6727 0.170(12) 1.0000 Uiso . H1083 H 0.7784 0.4446 0.5951 0.170(12) 1.0000 Uiso . H1021 H 0.5392 0.6413 0.7912 0.170(12) 1.0000 Uiso . H1011 H 0.4459 0.5136 0.5988 0.170(12) 1.0000 Uiso . 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 0.084(9) 0.079(9) 0.147(13) 0.008(8) -0.042(9) -0.032(8) C2 0.062(8) 0.067(8) 0.10(1) -0.010(8) -0.029(8) -0.011(7) C3 0.062(7) 0.064(7) 0.080(8) -0.006(6) -0.018(6) -0.011(6) C4 0.068(7) 0.065(7) 0.072(7) -0.006(6) -0.022(6) -0.012(6) C5 0.056(7) 0.059(7) 0.065(7) -0.006(5) -0.012(5) -0.016(6) C6 0.076(8) 0.086(8) 0.055(6) -0.006(6) -0.012(6) -0.036(7) C7 0.061(7) 0.079(8) 0.061(7) -0.011(6) -0.007(5) -0.037(6) C8 0.060(6) 0.038(5) 0.049(5) -0.006(4) -0.024(5) 0.000(5) C9 0.057(7) 0.056(6) 0.069(6) -0.007(5) -0.025(5) -0.019(6) C10 0.070(7) 0.055(7) 0.073(7) -0.012(6) -0.025(6) -0.010(6) C11 0.044(5) 0.048(6) 0.045(5) -0.008(4) -0.015(5) -0.005(5) C12 0.051(6) 0.051(6) 0.042(5) -0.005(4) -0.012(5) -0.008(5) C13 0.061(7) 0.062(7) 0.058(6) -0.018(5) -0.018(5) -0.012(6) C14 0.10(1) 0.131(11) 0.074(8) -0.057(8) 0.003(7) -0.035(9) C15 0.087(9) 0.079(8) 0.082(8) -0.015(6) -0.037(7) -0.012(7) C16 0.047(5) 0.042(5) 0.039(5) -0.002(4) -0.016(4) -0.000(5) C17 0.047(5) 0.045(6) 0.042(5) -0.002(4) -0.011(4) -0.014(5) C18 0.083(8) 0.084(9) 0.059(7) -0.019(6) 0.001(6) -0.033(7) C19 0.086(8) 0.069(8) 0.076(7) -0.028(6) -0.008(7) -0.027(7) C20 0.057(6) 0.050(6) 0.061(6) -0.008(5) -0.015(5) -0.011(5) C21 0.075(8) 0.077(8) 0.063(7) -0.020(6) 0.006(6) -0.024(7) C22 0.063(7) 0.065(7) 0.071(7) -0.021(6) -0.000(6) -0.019(6) C23 0.066(8) 0.058(8) 0.091(9) -0.018(6) -0.019(7) -0.014(7) C24 0.09(2) 0.066(16) 0.11(2) 0.015(14) -0.035(16) -0.043(16) C25 0.11(2) 0.08(2) 0.070(17) -0.014(15) -0.029(16) -0.039(19) C26 0.056(17) 0.07(2) 0.12(3) -0.013(18) -0.025(18) -0.007(15) C27 0.12(3) 0.11(3) 0.11(3) -0.03(2) 0.00(2) -0.04(3) C28 0.12(3) 0.07(2) 0.11(3) -0.003(19) -0.02(2) -0.04(2) C29 0.09(2) 0.09(2) 0.12(2) -0.038(18) -0.028(18) -0.001(18) C101 0.085(8) 0.068(7) 0.047(6) -0.019(5) -0.015(6) -0.015(6) C102 0.075(7) 0.051(6) 0.045(5) -0.013(5) -0.013(5) -0.010(6) C103 0.068(7) 0.059(7) 0.048(6) -0.011(5) -0.013(5) -0.015(6) C104 0.067(7) 0.061(7) 0.047(6) -0.006(5) -0.011(5) -0.013(6) C105 0.154(14) 0.09(1) 0.053(7) -0.005(7) -0.022(8) -0.04(1) C106 0.19(2) 0.108(13) 0.120(13) -0.021(11) -0.046(13) 0.013(14) C107 0.073(9) 0.114(11) 0.083(9) -0.027(8) -0.011(7) -0.003(8) C108 0.122(14) 0.150(16) 0.107(12) -0.048(11) -0.04(1) 0.055(12) N1 0.048(5) 0.048(5) 0.048(4) 0.000(4) -0.015(4) -0.015(4) N2 0.045(5) 0.047(5) 0.045(4) -0.008(4) -0.012(4) -0.008(4) N3 0.046(5) 0.056(5) 0.047(5) -0.007(4) -0.014(4) -0.016(4) N4 0.047(5) 0.056(5) 0.051(5) -0.014(4) -0.012(4) -0.008(4) N5 0.054(5) 0.053(5) 0.041(4) -0.005(4) -0.010(4) -0.016(4) N101 0.078(6) 0.067(6) 0.054(5) -0.019(4) -0.015(5) -0.014(5) N102 0.065(5) 0.069(6) 0.042(4) -0.016(4) -0.013(4) -0.017(5) O1 0.072(6) 0.069(5) 0.128(7) -0.011(5) -0.025(5) -0.021(5) O2 0.115(8) 0.136(9) 0.107(8) -0.022(7) -0.008(6) -0.060(7) O3 0.064(4) 0.081(5) 0.045(4) -0.015(3) -0.012(3) -0.024(4) O101 0.113(7) 0.109(7) 0.056(5) -0.034(4) -0.011(4) -0.041(5) O102 0.082(5) 0.079(5) 0.054(4) -0.019(4) -0.004(4) -0.029(4) O103 0.087(6) 0.091(6) 0.055(4) -0.025(4) -0.011(4) -0.030(5) _refine_ls_extinction_coef 141.5 _refine_ls_extinction_method 'Larson 1970 Crystallographic Computing eq 22' loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 . O1 . 1.409(14) yes C1 . H11 . 1.007 no C1 . H12 . 1.000 no C1 . H13 . 1.017 no C2 . C3 . 1.432(16) yes C2 . O1 . 1.304(15) yes C2 . O2 . 1.217(15) yes C3 . C4 . 1.307(15) yes C3 . H31 . 1.016 no C4 . C5 . 1.462(14) yes C4 . H41 . 1.009 no C5 . C6 . 1.377(14) yes C5 . C10 . 1.334(14) yes C6 . C7 . 1.355(13) yes C6 . H61 . 1.007 no C7 . C8 . 1.377(13) yes C7 . H71 . 1.009 no C8 . C9 . 1.370(12) yes C8 . N1 . 1.411(11) yes C9 . C10 . 1.380(13) yes C9 . H91 . 1.008 no C10 . H101 . 1.015 no C11 . N1 . 1.355(11) yes C11 . N2 . 1.303(11) yes C11 . N3 . 1.313(11) yes C12 . N3 . 1.312(11) yes C12 . N4 . 1.328(11) yes C12 . O3 . 1.31(1) yes C13 . C14 . 1.501(15) yes C13 . C15 . 1.487(16) yes C13 . O3 . 1.461(11) yes C13 . H131 . 1.008 no C14 . H141 . 0.994 no C14 . H142 . 1.007 no C14 . H143 . 1.010 no C15 . H150 . 1.000 no C15 . H151 . 1.000 no C15 . H152 . 1.009 no C16 . N2 . 1.335(11) yes C16 . N4 . 1.311(11) yes C16 . N5 . 1.362(11) yes C17 . C18 . 1.397(13) yes C17 . C22 . 1.365(13) yes C17 . N5 . 1.40(1) yes C18 . C19 . 1.374(14) yes C18 . H181 . 1.008 no C19 . C20 . 1.372(14) yes C19 . H191 . 1.011 no C20 . C21 . 1.363(14) yes C20 . C23 . 1.496(14) yes C21 . C22 . 1.371(14) yes C21 . H211 . 1.011 no C22 . H221 . 1.009 no C23 . C24 . 1.62(3) yes C23 . C25 . 1.52(3) yes C23 . C26 . 1.45(3) yes C23 . C27 . 1.47(4) yes C23 . C28 . 1.37(4) yes C23 . C29 . 1.64(3) yes C24 . C27 . 1.70(5) yes C24 . C28 . 1.66(5) yes C24 . H240 . 0.991 no C24 . H241 . 1.026 no C24 . H242 . 1.004 no C25 . C28 . 1.08(4) yes C25 . C29 . 1.50(4) yes C25 . H250 . 1.003 no C25 . H251 . 0.990 no C25 . H252 . 1.017 no C25 . H281 . 0.970 no C26 . C27 . 1.01(4) yes C26 . C29 . 1.52(5) yes C26 . H260 . 0.996 no C26 . H261 . 0.999 no C26 . H262 . 1.034 no C26 . H271 . 0.883 no C27 . H262 . 1.038 no C27 . H270 . 1.005 no C27 . H271 . 1.007 no C27 . H272 . 1.016 no C28 . H252 . 1.063 no C28 . H280 . 0.989 no C28 . H281 . 0.999 no C28 . H282 . 1.029 no C29 . H251 . 1.282 no C29 . H290 . 1.007 no C29 . H291 . 1.003 no C29 . H292 . 1.016 no C101 . C104 . 1.490(14) yes C101 . N101 . 1.370(13) yes C101 . O101 . 1.194(11) yes C102 . N101 . 1.355(12) yes C102 . N102 . 1.362(12) yes C102 . O102 . 1.217(11) yes C103 . C104 . 1.524(13) yes C103 . N102 . 1.358(12) yes C103 . O103 . 1.194(11) yes C104 . C105 . 1.530(17) yes C104 . C107 . 1.547(17) yes C105 . C106 . 1.51(2) yes C105 . H1051 . 1.012 no C105 . H1052 . 1.015 no C106 . H1061 . 1.020 no C106 . H1062 . 1.009 no C106 . H1063 . 1.022 no C107 . C108 . 1.46(2) yes C107 . H1071 . 1.019 no C107 . H1072 . 1.008 no C108 . H1081 . 1.001 no C108 . H1082 . 1.008 no C108 . H1083 . 1.030 no N101 . H1011 . 1.010 no N102 . H1021 . 1.011 no H251 . H291 . 0.667 no H252 . H281 . 0.170 no H261 . H292 . 0.665 no H262 . H271 . 0.278 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O1 . C1 . H11 . 110.595 no O1 . C1 . H12 . 111.171 no H11 . C1 . H12 . 108.974 no O1 . C1 . H13 . 110.256 no H11 . C1 . H13 . 107.607 no H12 . C1 . H13 . 108.133 no C3 . C2 . O1 . 112.9(13) yes C3 . C2 . O2 . 124.9(12) yes O1 . C2 . O2 . 122.2(11) yes C2 . C3 . C4 . 123.6(12) yes C2 . C3 . H31 . 117.497 no C4 . C3 . H31 . 118.930 no C3 . C4 . C5 . 127.2(11) yes C3 . C4 . H41 . 116.264 no C5 . C4 . H41 . 116.583 no C4 . C5 . C6 . 120.1(10) yes C4 . C5 . C10 . 123.6(10) yes C6 . C5 . C10 . 116.3(9) yes C5 . C6 . C7 . 123.2(10) yes C5 . C6 . H61 . 118.347 no C7 . C6 . H61 . 118.488 no C6 . C7 . C8 . 119.4(9) yes C6 . C7 . H71 . 120.327 no C8 . C7 . H71 . 120.222 no C7 . C8 . C9 . 118.3(9) yes C7 . C8 . N1 . 125.9(8) yes C9 . C8 . N1 . 115.8(8) yes C8 . C9 . C10 . 119.9(9) yes C8 . C9 . H91 . 119.475 no C10 . C9 . H91 . 120.614 no C5 . C10 . C9 . 122.8(9) yes C5 . C10 . H101 . 118.806 no C9 . C10 . H101 . 118.361 no N1 . C11 . N2 . 115.2(8) yes N1 . C11 . N3 . 119.1(8) yes N2 . C11 . N3 . 125.5(8) yes N3 . C12 . N4 . 126.6(9) yes N3 . C12 . O3 . 114.4(8) yes N4 . C12 . O3 . 118.8(8) yes C14 . C13 . C15 . 113.6(10) yes C14 . C13 . O3 . 104.9(8) yes C15 . C13 . O3 . 109.6(9) yes C14 . C13 . H131 . 110.267 no C15 . C13 . H131 . 104.836 no O3 . C13 . H131 . 113.815 no C13 . C14 . H141 . 110.551 no C13 . C14 . H142 . 110.116 no H141 . C14 . H142 . 109.392 no C13 . C14 . H143 . 109.491 no H141 . C14 . H143 . 109.106 no H142 . C14 . H143 . 108.141 no C13 . C15 . H150 . 110.205 no C13 . C15 . H151 . 109.731 no H150 . C15 . H151 . 109.483 no C13 . C15 . H152 . 109.843 no H150 . C15 . H152 . 108.791 no H151 . C15 . H152 . 108.761 no N2 . C16 . N4 . 125.8(8) yes N2 . C16 . N5 . 115.4(8) yes N4 . C16 . N5 . 118.7(8) yes C18 . C17 . C22 . 117.6(8) yes C18 . C17 . N5 . 126.3(8) yes C22 . C17 . N5 . 116.1(8) yes C17 . C18 . C19 . 119.1(9) yes C17 . C18 . H181 . 120.004 no C19 . C18 . H181 . 120.937 no C18 . C19 . C20 . 123.8(10) yes C18 . C19 . H191 . 118.046 no C20 . C19 . H191 . 118.115 no C19 . C20 . C21 . 115.3(9) yes C19 . C20 . C23 . 122.7(9) yes C21 . C20 . C23 . 121.9(9) yes C20 . C21 . C22 . 123.0(9) yes C20 . C21 . H211 . 117.865 no C22 . C21 . H211 . 119.173 no C17 . C22 . C21 . 121.1(9) yes C17 . C22 . H221 . 119.408 no C21 . C22 . H221 . 119.477 no C20 . C23 . C24 . 107.8(11) yes C20 . C23 . C25 . 114.6(12) yes C24 . C23 . C25 . 107.3(20) yes C20 . C23 . C26 . 111.9(15) yes C24 . C23 . C26 . 106.6(18) yes C25 . C23 . C26 . 108.3(21) yes C20 . C23 . C27 . 118.2(17) yes C24 . C23 . C27 . 66.6(22) yes C25 . C23 . C27 . 126.0(19) yes C26 . C23 . C27 . 40.5(17) yes C20 . C23 . C28 . 113.0(15) yes C24 . C23 . C28 . 66.9(20) yes C25 . C23 . C28 . 43.3(16) yes C26 . C23 . C28 . 134.4(19) yes C27 . C23 . C28 . 118.4(22) yes C20 . C23 . C29 . 108.8(13) yes C24 . C23 . C29 . 143.4(14) yes C25 . C23 . C29 . 56.6(17) yes C26 . C23 . C29 . 58.4(18) yes C27 . C23 . C29 . 95.3(22) yes C28 . C23 . C29 . 98.8(21) yes C23 . C24 . C27 . 52.5(15) yes C23 . C24 . C28 . 49.3(15) yes C27 . C24 . C28 . 93.0(23) yes C23 . C24 . H240 . 111.537 no C27 . C24 . H240 . 86.810 no C28 . C24 . H240 . 90.257 no C23 . C24 . H241 . 109.767 no C27 . C24 . H241 . 161.104 no C28 . C24 . H241 . 75.773 no H240 . C24 . H241 . 108.077 no C23 . C24 . H242 . 110.431 no C27 . C24 . H242 . 77.421 no C28 . C24 . H242 . 156.923 no H240 . C24 . H242 . 109.838 no H241 . C24 . H242 . 107.058 no C23 . C25 . C28 . 60.8(24) yes C23 . C25 . C29 . 65.7(18) yes C28 . C25 . C29 . 124.6(36) yes C23 . C25 . H250 . 109.957 no C28 . C25 . H250 . 91.665 no C29 . C25 . H250 . 93.335 no C23 . C25 . H251 . 110.495 no C28 . C25 . H251 . 158.275 no C29 . C25 . H251 . 57.527 no H250 . C25 . H251 . 110.019 no C23 . C25 . H252 . 109.520 no C28 . C25 . H252 . 60.953 no C29 . C25 . H252 . 158.277 no H250 . C25 . H252 . 107.878 no H251 . C25 . H252 . 108.921 no C23 . C25 . H281 . 101.474 no C28 . C25 . H281 . 58.173 no C29 . C25 . H281 . 150.518 no H250 . C25 . H281 . 116.147 no H251 . C25 . H281 . 108.430 no H252 . C25 . H281 . 9.444 no C23 . C26 . C27 . 70.8(32) yes C23 . C26 . C29 . 67.0(20) yes C27 . C26 . C29 . 130.0(45) yes C23 . C26 . H260 . 111.954 no C27 . C26 . H260 . 80.101 no C29 . C26 . H260 . 91.618 no C23 . C26 . H261 . 111.402 no C27 . C26 . H261 . 166.807 no C29 . C26 . H261 . 59.998 no H260 . C26 . H261 . 109.934 no C23 . C26 . H262 . 109.251 no C27 . C26 . H262 . 60.942 no C29 . C26 . H262 . 160.441 no H260 . C26 . H262 . 107.146 no H261 . C26 . H262 . 106.935 no C23 . C26 . H271 . 121.401 no C27 . C26 . H271 . 63.780 no C29 . C26 . H271 . 165.801 no H260 . C26 . H271 . 94.931 no H261 . C26 . H271 . 105.858 no H262 . C26 . H271 . 14.013 no C23 . C27 . C24 . 60.9(19) yes C23 . C27 . C26 . 68.7(30) yes C24 . C27 . C26 . 128.7(42) yes C23 . C27 . H262 . 107.636 no C24 . C27 . H262 . 143.758 no C26 . C27 . H262 . 60.550 no C23 . C27 . H270 . 111.395 no C24 . C27 . H270 . 92.649 no C26 . C27 . H270 . 97.241 no H262 . C27 . H270 . 122.541 no C23 . C27 . H271 . 110.639 no C24 . C27 . H271 . 158.741 no C26 . C27 . H271 . 51.849 no H262 . C27 . H271 . 15.512 no H270 . C27 . H271 . 108.543 no C23 . C27 . H272 . 110.650 no C24 . C27 . H272 . 62.522 no C26 . C27 . H272 . 152.450 no H262 . C27 . H272 . 95.466 no H270 . C27 . H272 . 107.840 no H271 . C27 . H272 . 107.644 no C23 . C28 . C24 . 63.8(20) yes C23 . C28 . C25 . 75.9(31) yes C24 . C28 . C25 . 134.1(41) yes C23 . C28 . H252 . 118.229 no C24 . C28 . H252 . 165.125 no C25 . C28 . H252 . 56.772 no C23 . C28 . H280 . 111.304 no C24 . C28 . H280 . 89.538 no C25 . C28 . H280 . 85.336 no H252 . C28 . H280 . 102.501 no C23 . C28 . H281 . 110.743 no C24 . C28 . H281 . 159.449 no C25 . C28 . H281 . 55.612 no H252 . C28 . H281 . 8.775 no H280 . C28 . H281 . 110.443 no C23 . C28 . H282 . 108.954 no C24 . C28 . H282 . 59.984 no C25 . C28 . H282 . 161.947 no H252 . C28 . H282 . 107.302 no H280 . C28 . H282 . 108.008 no H281 . C28 . H282 . 107.252 no C23 . C29 . C25 . 57.6(15) yes C23 . C29 . C26 . 54.5(16) yes C25 . C29 . C26 . 105.8(25) yes C23 . C29 . H251 . 90.127 no C25 . C29 . H251 . 40.648 no C26 . C29 . H251 . 144.188 no C23 . C29 . H290 . 111.058 no C25 . C29 . H290 . 87.301 no C26 . C29 . H290 . 91.032 no H251 . C29 . H290 . 97.611 no C23 . C29 . H291 . 111.410 no C25 . C29 . H291 . 71.259 no C26 . C29 . H291 . 159.714 no H251 . C29 . H291 . 30.957 no H290 . C29 . H291 . 108.632 no C23 . C29 . H292 . 110.053 no C25 . C29 . H292 . 164.025 no C26 . C29 . H292 . 69.180 no H251 . C29 . H292 . 138.304 no H290 . C29 . H292 . 107.623 no H291 . C29 . H292 . 107.934 no C104 . C101 . N101 . 117.5(9) yes C104 . C101 . O101 . 121.5(10) yes N101 . C101 . O101 . 121.0(9) yes N101 . C102 . N102 . 117.0(9) yes N101 . C102 . O102 . 121.7(9) yes N102 . C102 . O102 . 120.9(9) yes C104 . C103 . N102 . 117.6(9) yes C104 . C103 . O103 . 121.7(9) yes N102 . C103 . O103 . 120.7(9) yes C101 . C104 . C103 . 115.3(8) yes C101 . C104 . C105 . 108.8(10) yes C103 . C104 . C105 . 107.2(9) yes C101 . C104 . C107 . 108.0(10) yes C103 . C104 . C107 . 106.7(9) yes C105 . C104 . C107 . 111.0(11) yes C104 . C105 . C106 . 115.6(12) yes C104 . C105 . H1051 . 108.286 no C106 . C105 . H1051 . 108.352 no C104 . C105 . H1052 . 108.174 no C106 . C105 . H1052 . 108.714 no H1051 . C105 . H1052 . 107.378 no C105 . C106 . H1061 . 112.443 no C105 . C106 . H1062 . 112.101 no H1061 . C106 . H1062 . 107.234 no C105 . C106 . H1063 . 111.384 no H1061 . C106 . H1063 . 106.245 no H1062 . C106 . H1063 . 107.078 no C104 . C107 . C108 . 115.5(11) yes C104 . C107 . H1071 . 107.992 no C108 . C107 . H1071 . 107.735 no C104 . C107 . H1072 . 108.685 no C108 . C107 . H1072 . 109.300 no H1071 . C107 . H1072 . 107.318 no C107 . C108 . H1081 . 112.838 no C107 . C108 . H1082 . 111.572 no H1081 . C108 . H1082 . 108.785 no C107 . C108 . H1083 . 109.742 no H1081 . C108 . H1083 . 107.083 no H1082 . C108 . H1083 . 106.531 no C8 . N1 . C11 . 130.5(8) yes C11 . N2 . C16 . 114.5(8) yes C11 . N3 . C12 . 114.1(7) yes C12 . N4 . C16 . 113.0(7) yes C16 . N5 . C17 . 130.1(8) yes C101 . N101 . C102 . 126.6(9) yes C101 . N101 . H1011 . 116.853 no C102 . N101 . H1011 . 116.589 no C102 . N102 . C103 . 126.0(9) yes C102 . N102 . H1021 . 117.008 no C103 . N102 . H1021 . 117.004 no C1 . O1 . C2 . 117.2(11) yes C12 . O3 . C13 . 119.2(7) yes C25 . H251 . C29 . 81.825 no C25 . H251 . H291 . 131.553 no C29 . H251 . H291 . 50.739 no C25 . H252 . C28 . 62.274 no C25 . H252 . H281 . 69.476 no C28 . H252 . H281 . 63.708 no C26 . H261 . H292 . 127.291 no C26 . H262 . C27 . 58.507 no C26 . H262 . H271 . 50.361 no C27 . H262 . H271 . 75.996 no C26 . H271 . C27 . 64.371 no C26 . H271 . H262 . 115.627 no C27 . H271 . H262 . 88.492 no C25 . H281 . C28 . 66.215 no C25 . H281 . H252 . 101.081 no C28 . H281 . H252 . 107.516 no C29 . H291 . H251 . 98.305 no C29 . H292 . H261 . 103.434 no