# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_year 2009 _journal_page_first 1350 _journal_volume ? _publ_contact_author_name 'Graeme Cooke' _publ_contact_author_email GRAEMEC@CHEM.GLA.AC.UK _publ_section_title ; Model systems for flavoenzyme activity: an investigation of the role functionality attached to the C(7) position of the flavin unit has on redox and molecular recognition properties. ; _publ_requested_category FO loop_ _publ_author_name 'Stuart T. Caldwell' L.J.Farrugia 'Shanika Gunatilaka Hewage' 'Nadiya Kryvokhyzha' V.M.Rotello 'Graeme Cooke' # Attachment 'archive.cif' data_cooke001 _database_code_depnum_ccdc_archive 'CCDC 715445' _audit_creation_date 2009-01-07T11:02:46-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety '4(C16 H19 N5 O2), C7 H8' _chemical_formula_sum 'C71 H84 N20 O8' _chemical_formula_weight 1345.58 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _space_group_crystal_system triclinic _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' _space_group_IT_number 2 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.3010(4) _cell_length_b 11.8400(5) _cell_length_c 16.1447(7) _cell_angle_alpha 106.983(2) _cell_angle_beta 108.228(2) _cell_angle_gamma 106.322(2) _cell_volume 1631.48(12) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6782 _cell_measurement_theta_min 2 _cell_measurement_theta_max 20 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour black _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.37 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 714 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2004/1 - Bruker Nonius area detector scaling and absorption correction ; _exptl_absorpt_correction_T_min 0.774 _exptl_absorpt_correction_T_max 0.995 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'sealed x-ray tube' _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'APEX-II CCD' _diffrn_orient_matrix_type 'x-axis to radiation source' _diffrn_orient_matrix_ub_11 -0.321152E-1 _diffrn_orient_matrix_ub_12 -0.796841E-1 _diffrn_orient_matrix_ub_13 0.115356E-1 _diffrn_orient_matrix_ub_21 -0.337713E-1 _diffrn_orient_matrix_ub_22 0.439275E-1 _diffrn_orient_matrix_ub_23 0.468442E-1 _diffrn_orient_matrix_ub_31 -0.101905 _diffrn_orient_matrix_ub_32 -0.330896E-1 _diffrn_orient_matrix_ub_33 -0.530997E-1 _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Bruker APEX-II' _diffrn_measurement_method '\f or \w oscillation scans' _diffrn_reflns_av_R_equivalents 0.0412 _diffrn_reflns_av_unetI/netI 0.0508 _diffrn_reflns_number 39465 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.46 _diffrn_reflns_theta_max 25.24 _diffrn_reflns_theta_full 25.24 _diffrn_measured_fraction_theta_full 0.982 _diffrn_measured_fraction_theta_max 0.982 _reflns_number_total 5795 _reflns_number_gt 4155 _reflns_threshold_expression >2\s(I) _diffrn_reflns_reduction_process ; Scaled and merged with Sortav R.H. Blessing, (1987) Cryst. Rev. 1, 3-58 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397 ; #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker APEX-2 software (2007)' _computing_cell_refinement 'SAINT integration software (2007)' _computing_data_reduction 'SORTAV (Blessing, 1995)' _computing_structure_solution 'SUPERFLIP (Palatinus & Chapius, 2007)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^ > 2\s(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^)+(0.0452P)^2^+0.2218P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 5795 _refine_ls_number_parameters 460 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0682 _refine_ls_R_factor_gt 0.0414 _refine_ls_wR_factor_ref 0.1041 _refine_ls_wR_factor_gt 0.096 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.182 _refine_diff_density_min -0.216 _refine_diff_density_rms 0.037 #----------------------------------------------------------------------------# # 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 O O 0.0106 0.006 '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' 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' 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 O18 O 0.90037(15) 0.77530(12) 0.65173(9) 0.0428(3) Uani 1 1 d . . . O19 O 0.46502(16) 0.49278(16) 0.39178(9) 0.0526(4) Uani 1 1 d . . . N10 N 0.83156(18) 0.73397(15) 0.33539(10) 0.0364(4) Uani 1 1 d . . . N11 N 1.01952(19) 0.85201(15) 0.53298(10) 0.0354(4) Uani 1 1 d . . . N12 N 0.64324(19) 0.60837(17) 0.35952(11) 0.0407(4) Uani 1 1 d . . . N13 N 0.68507(18) 0.63211(16) 0.51920(10) 0.0383(4) Uani 1 1 d . . . H13 H 0.6477 0.605 0.5554 0.046 Uiso 1 1 calc R . . N100 N 1.4102(2) 1.12195(16) 0.48634(12) 0.0573(5) Uani 1 1 d . . . C10 C 1.2697(2) 1.02600(18) 0.45032(14) 0.0423(5) Uani 1 1 d . . . C11 C 1.1735(3) 0.96795(19) 0.35052(14) 0.0435(5) Uani 1 1 d . . . H11 H 1.2093 0.9957 0.3092 0.052 Uiso 1 1 calc R . . C12 C 1.0316(2) 0.87381(19) 0.31147(14) 0.0417(5) Uani 1 1 d . . . H12 H 0.9713 0.8379 0.2443 0.05 Uiso 1 1 calc R . . C13 C 0.9744(2) 0.82993(18) 0.37022(13) 0.0370(5) Uani 1 1 d . . . C14 C 1.0678(2) 0.88683(18) 0.47006(13) 0.0349(4) Uani 1 1 d . . . C15 C 1.2133(2) 0.98248(18) 0.50846(13) 0.0378(5) Uani 1 1 d . . . H15 H 1.2745 1.0183 0.5754 0.045 Uiso 1 1 calc R . . C16 C 0.7813(2) 0.69851(19) 0.39673(13) 0.0362(5) Uani 1 1 d . . . C17 C 0.8835(2) 0.76402(18) 0.49734(13) 0.0347(4) Uani 1 1 d . . . C18 C 0.8281(2) 0.72689(18) 0.56504(13) 0.0359(5) Uani 1 1 d . . . C19 C 0.5930(2) 0.5745(2) 0.42110(13) 0.0409(5) Uani 1 1 d . . . C100 C 1.4699(3) 1.1584(2) 0.42255(16) 0.0616(7) Uani 1 1 d . . . H10L H 1.4769 1.0838 0.3807 0.092 Uiso 1 1 calc R . . H10M H 1.5697 1.2295 0.4608 0.092 Uiso 1 1 calc R . . H10N H 1.4031 1.1863 0.3833 0.092 Uiso 1 1 calc R . . C101 C 1.5121(2) 1.17220(19) 0.58625(14) 0.0485(5) Uani 1 1 d . . . H10D H 1.4646 1.2038 0.6265 0.073 Uiso 1 1 calc R . . H10E H 1.6039 1.2436 0.6007 0.073 Uiso 1 1 calc R . . H10F H 1.537 1.1033 0.5994 0.073 Uiso 1 1 calc R . . C102 C 0.7312(2) 0.66260(19) 0.23077(12) 0.0393(5) Uani 1 1 d . . . H10J H 0.7628 0.7148 0.197 0.047 Uiso 1 1 calc R . . H10K H 0.6274 0.6507 0.2203 0.047 Uiso 1 1 calc R . . C103 C 0.7341(2) 0.53028(19) 0.18829(13) 0.0380(5) Uani 1 1 d . . . H103 H 0.7036 0.4795 0.2239 0.046 Uiso 1 1 calc R . . C104 C 0.6189(2) 0.4588(2) 0.08366(14) 0.0489(5) Uani 1 1 d . . . H10G H 0.645 0.5082 0.0477 0.073 Uiso 1 1 calc R . . H10H H 0.5193 0.4492 0.0799 0.073 Uiso 1 1 calc R . . H10I H 0.6183 0.373 0.0561 0.073 Uiso 1 1 calc R . . C105 C 0.8881(2) 0.5395(2) 0.19695(14) 0.0451(5) Uani 1 1 d . . . H10A H 0.8838 0.4522 0.1695 0.068 Uiso 1 1 calc R . . H10B H 0.9599 0.5835 0.2648 0.068 Uiso 1 1 calc R . . H10C H 0.9201 0.5886 0.1622 0.068 Uiso 1 1 calc R . . O28 O 0.74405(12) 0.81826(10) 0.06498(8) 0.0293(3) Uani 1 1 d . . . O29 O 0.62968(12) 1.15504(10) 0.04539(8) 0.0288(3) Uani 1 1 d . . . N20 N 1.04283(14) 0.96439(12) 0.11429(9) 0.0214(3) Uani 1 1 d . . . N21 N 1.12572(14) 1.22689(12) 0.15189(9) 0.0215(3) Uani 1 1 d . . . N22 N 0.87710(14) 1.19778(12) 0.10268(9) 0.0240(3) Uani 1 1 d . . . N23 N 0.68886(14) 0.98555(12) 0.04720(9) 0.0233(3) Uani 1 1 d . . . H23 H 0.5923 0.9356 0.0188 0.028 Uiso 1 1 calc R . . N200 N 1.55220(14) 1.01272(12) 0.19779(10) 0.0252(3) Uani 1 1 d . . . C20 C 1.44620(17) 1.06390(15) 0.18699(11) 0.0218(4) Uani 1 1 d . . . C21 C 1.48779(18) 1.19757(15) 0.20719(11) 0.0246(4) Uani 1 1 d . . . H21 H 1.5904 1.251 0.2289 0.03 Uiso 1 1 calc R . . C22 C 1.38701(17) 1.25282(15) 0.19680(11) 0.0232(4) Uani 1 1 d . . . H22 H 1.4205 1.3427 0.2116 0.028 Uiso 1 1 calc R . . C23 C 1.23410(17) 1.17715(14) 0.16429(11) 0.0210(3) Uani 1 1 d . . . C24 C 1.18956(17) 1.04392(14) 0.14331(11) 0.0206(3) Uani 1 1 d . . . C25 C 1.29505(17) 0.98895(15) 0.15508(11) 0.0217(4) Uani 1 1 d . . . H25 H 1.2624 0.8993 0.141 0.026 Uiso 1 1 calc R . . C26 C 0.97805(17) 1.14802(15) 0.11780(11) 0.0221(4) Uani 1 1 d . . . C27 C 0.94427(17) 1.01455(14) 0.10187(11) 0.0208(3) Uani 1 1 d . . . C28 C 0.78455(17) 0.92858(15) 0.07024(11) 0.0227(4) Uani 1 1 d . . . C29 C 0.73037(18) 1.11638(15) 0.06468(11) 0.0240(4) Uani 1 1 d . . . C200 C 1.70883(18) 1.09721(16) 0.26264(12) 0.0298(4) Uani 1 1 d . . . H20D H 1.7457 1.1624 0.24 0.045 Uiso 1 1 calc R . . H20E H 1.7684 1.0456 0.2642 0.045 Uiso 1 1 calc R . . H20F H 1.7177 1.1404 0.3273 0.045 Uiso 1 1 calc R . . C201 C 1.50423(18) 0.87664(15) 0.17905(13) 0.0285(4) Uani 1 1 d . . . H20A H 1.4698 0.8617 0.2266 0.043 Uiso 1 1 calc R . . H20B H 1.5884 0.8519 0.1833 0.043 Uiso 1 1 calc R . . H20C H 1.422 0.8245 0.1146 0.043 Uiso 1 1 calc R . . C202 C 1.17170(18) 1.36792(14) 0.18103(12) 0.0241(4) Uani 1 1 d . . . H20G H 1.2647 1.4143 0.2416 0.029 Uiso 1 1 calc R . . H20H H 1.0929 1.3914 0.1941 0.029 Uiso 1 1 calc R . . C203 C 1.19910(18) 1.41448(14) 0.10655(12) 0.0247(4) Uani 1 1 d . . . H203 H 1.27 1.3817 0.0881 0.03 Uiso 1 1 calc R . . C204 C 1.05574(19) 1.36477(16) 0.01620(12) 0.0296(4) Uani 1 1 d . . . H20I H 1.0145 1.2701 -0.0152 0.044 Uiso 1 1 calc R . . H20J H 1.0779 1.4008 -0.0277 0.044 Uiso 1 1 calc R . . H20K H 0.9824 1.3915 0.0333 0.044 Uiso 1 1 calc R . . C205 C 1.2741(2) 1.56191(16) 0.15360(13) 0.0362(4) Uani 1 1 d . . . H20L H 1.2956 1.5938 0.1077 0.054 Uiso 1 1 calc R . . H20M H 1.3679 1.5908 0.2099 0.054 Uiso 1 1 calc R . . H20N H 1.2071 1.5959 0.1734 0.054 Uiso 1 1 calc R . . C30 C 0.9371(3) 0.4537(2) 0.40216(19) 0.0673(8) Uani 1 1 d . . . H30 H 0.8936 0.4202 0.3341 0.081 Uiso 1 1 calc R . . C31 C 0.8487(3) 0.4261(2) 0.4484(2) 0.0691(8) Uani 1 1 d . . . H31 H 0.7438 0.3763 0.4122 0.083 Uiso 1 1 calc R A 1 C32A C 0.9108(3) 0.4699(2) 0.54559(18) 0.0601(7) Uani 0.5 1 d P . 1 C33 C 0.8277(4) 0.4413(4) 0.5878(3) 0.0419(9) Uani 0.5 1 d P B 1 H33A H 0.7246 0.4244 0.548 0.063 Uiso 0.5 1 calc PR B 1 H33B H 0.8654 0.5138 0.65 0.063 Uiso 0.5 1 calc PR B 1 H33C H 0.8297 0.3639 0.5978 0.063 Uiso 0.5 1 calc PR B 1 C32B C 0.9108(3) 0.4699(2) 0.54559(18) 0.0601(7) Uani 0.5 1 d P . 2 H32B H 0.8504 0.4481 0.5773 0.072 Uiso 0.5 1 calc PR . 2 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 O18 0.0644(9) 0.0441(8) 0.0271(8) 0.0188(6) 0.0238(7) 0.0232(7) O19 0.0375(9) 0.1014(12) 0.0326(8) 0.0361(8) 0.0191(7) 0.0338(9) N10 0.0529(11) 0.0564(10) 0.0299(8) 0.0278(8) 0.0279(8) 0.0411(9) N11 0.0536(11) 0.0469(9) 0.0322(9) 0.0255(8) 0.0276(9) 0.0368(9) N12 0.0466(11) 0.0734(12) 0.0304(9) 0.0315(8) 0.0255(9) 0.0421(10) N13 0.0458(11) 0.0636(11) 0.0284(9) 0.0285(8) 0.0240(8) 0.0344(9) N100 0.0951(15) 0.0404(10) 0.0365(10) 0.0187(8) 0.0383(11) 0.0138(10) C10 0.0749(15) 0.0363(11) 0.0384(11) 0.0224(9) 0.0361(12) 0.0330(11) C11 0.0764(16) 0.0467(12) 0.0394(12) 0.0291(10) 0.0394(12) 0.0402(12) C12 0.0682(15) 0.0538(12) 0.0337(11) 0.0280(10) 0.0338(11) 0.0425(12) C13 0.0597(14) 0.0495(12) 0.0331(11) 0.0264(9) 0.0314(10) 0.0420(11) C14 0.0573(13) 0.0470(11) 0.0330(10) 0.0271(9) 0.0315(10) 0.0410(11) C15 0.0625(14) 0.0430(11) 0.0315(10) 0.0228(9) 0.0289(11) 0.0361(11) C16 0.0500(13) 0.0582(12) 0.0324(11) 0.0293(10) 0.0277(10) 0.0432(11) C17 0.0535(13) 0.0495(12) 0.0304(10) 0.0260(9) 0.0272(10) 0.0404(11) C18 0.0550(14) 0.0459(11) 0.0312(11) 0.0243(9) 0.0266(11) 0.0356(11) C19 0.0439(13) 0.0747(14) 0.0307(11) 0.0305(10) 0.0231(11) 0.0434(12) C100 0.0966(19) 0.0543(14) 0.0494(14) 0.0289(11) 0.0480(14) 0.0256(13) C101 0.0712(15) 0.0424(12) 0.0436(12) 0.0216(10) 0.0366(12) 0.0219(11) C102 0.0519(13) 0.0667(13) 0.0289(10) 0.0307(10) 0.0248(10) 0.0444(11) C103 0.0490(12) 0.0584(12) 0.0310(10) 0.0272(9) 0.0243(10) 0.0382(10) C104 0.0539(14) 0.0687(14) 0.0391(12) 0.0278(11) 0.0226(11) 0.0366(12) C105 0.0567(14) 0.0639(13) 0.0379(11) 0.0263(10) 0.0270(11) 0.0434(11) O28 0.0228(6) 0.0283(7) 0.0414(7) 0.0189(5) 0.0154(6) 0.0106(5) O29 0.0207(6) 0.0349(7) 0.0401(7) 0.0223(6) 0.0143(6) 0.0155(5) N20 0.0188(8) 0.0265(7) 0.0217(7) 0.0123(6) 0.0096(6) 0.0095(6) N21 0.0198(8) 0.0242(7) 0.0253(7) 0.0133(6) 0.0116(6) 0.0100(6) N22 0.0196(8) 0.0287(8) 0.0302(8) 0.0167(6) 0.0125(7) 0.0120(6) N23 0.0155(7) 0.0285(8) 0.0300(8) 0.0164(6) 0.0111(6) 0.0088(6) N200 0.0182(7) 0.0271(7) 0.0328(8) 0.0152(6) 0.0106(7) 0.0101(6) C20 0.0204(9) 0.0284(9) 0.0227(9) 0.0143(7) 0.0113(8) 0.0120(7) C21 0.0175(9) 0.0298(9) 0.0268(9) 0.0136(7) 0.0101(8) 0.0076(7) C22 0.0214(9) 0.0231(8) 0.0267(9) 0.0131(7) 0.0106(8) 0.0083(7) C23 0.0205(9) 0.0257(9) 0.0199(8) 0.0117(7) 0.0095(7) 0.0105(7) C24 0.0192(9) 0.0247(8) 0.0177(8) 0.0092(7) 0.0081(7) 0.0078(7) C25 0.0236(9) 0.0237(8) 0.0226(9) 0.0126(7) 0.0121(8) 0.0106(7) C26 0.0217(9) 0.0287(9) 0.0217(9) 0.0139(7) 0.0124(8) 0.0113(7) C27 0.0208(9) 0.0272(9) 0.0193(8) 0.0132(7) 0.0101(7) 0.0111(7) C28 0.0216(9) 0.0279(9) 0.0233(9) 0.0132(7) 0.0119(8) 0.0114(7) C29 0.0233(10) 0.0305(9) 0.0272(9) 0.0169(8) 0.0147(8) 0.0138(8) C200 0.0207(9) 0.0357(10) 0.0333(10) 0.0139(8) 0.0108(8) 0.0133(8) C201 0.0252(10) 0.0301(9) 0.0393(10) 0.0192(8) 0.0168(9) 0.0152(8) C202 0.0227(9) 0.0225(8) 0.0280(9) 0.0101(7) 0.0112(8) 0.0105(7) C203 0.0248(9) 0.0226(8) 0.0304(9) 0.0122(7) 0.0147(8) 0.0105(7) C204 0.0347(10) 0.0291(9) 0.0317(10) 0.0174(8) 0.0169(9) 0.0144(8) C205 0.0378(11) 0.0273(9) 0.0391(11) 0.0137(8) 0.0152(9) 0.0090(8) C30 0.0624(17) 0.0339(12) 0.0610(16) 0.0103(12) -0.0167(15) 0.0182(12) C31 0.0553(16) 0.0355(13) 0.0734(19) 0.0110(13) -0.0110(15) 0.0163(12) C32A 0.0527(16) 0.0390(12) 0.0573(16) 0.0156(11) -0.0103(13) 0.0197(11) C33 0.031(2) 0.042(2) 0.043(2) 0.0187(19) 0.011(2) 0.0074(18) C32B 0.0527(16) 0.0390(12) 0.0573(16) 0.0156(11) -0.0103(13) 0.0197(11) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O18 C18 1.217(2) . ? O19 C19 1.234(2) . ? N10 C16 1.366(2) . ? N10 C13 1.394(2) . ? N10 C102 1.489(2) . ? N11 C17 1.306(2) . ? N11 C14 1.376(2) . ? N12 C16 1.327(2) . ? N12 C19 1.362(2) . ? N13 C18 1.372(2) . ? N13 C19 1.392(2) . ? N13 H13 0.88 . ? N100 C10 1.373(3) . ? N100 C101 1.445(3) . ? N100 C100 1.460(2) . ? C10 C15 1.393(2) . ? C10 C11 1.422(3) . ? C11 C12 1.369(3) . ? C11 H11 0.95 . ? C12 C13 1.408(2) . ? C12 H12 0.95 . ? C13 C14 1.417(3) . ? C14 C15 1.403(3) . ? C15 H15 0.95 . ? C16 C17 1.443(3) . ? C17 C18 1.497(2) . ? C100 H10L 0.98 . ? C100 H10M 0.98 . ? C100 H10N 0.98 . ? C101 H10D 0.98 . ? C101 H10E 0.98 . ? C101 H10F 0.98 . ? C102 C103 1.529(2) . ? C102 H10J 0.99 . ? C102 H10K 0.99 . ? C103 C105 1.518(2) . ? C103 C104 1.524(3) . ? C103 H103 1 . ? C104 H10G 0.98 . ? C104 H10H 0.98 . ? C104 H10I 0.98 . ? C105 H10A 0.98 . ? C105 H10B 0.98 . ? C105 H10C 0.98 . ? O28 C28 1.2224(18) . ? O29 C29 1.2371(18) . ? N20 C27 1.3057(19) . ? N20 C24 1.3747(19) . ? N21 C26 1.3663(19) . ? N21 C23 1.3899(19) . ? N21 C202 1.4802(19) . ? N22 C26 1.3257(19) . ? N22 C29 1.359(2) . ? N23 C28 1.3623(19) . ? N23 C29 1.3996(19) . ? N23 H23 0.88 . ? N200 C20 1.3800(19) . ? N200 C201 1.4512(19) . ? N200 C200 1.457(2) . ? C20 C25 1.390(2) . ? C20 C21 1.423(2) . ? C21 C22 1.368(2) . ? C21 H21 0.95 . ? C22 C23 1.405(2) . ? C22 H22 0.95 . ? C23 C24 1.413(2) . ? C24 C25 1.408(2) . ? C25 H25 0.95 . ? C26 C27 1.443(2) . ? C27 C28 1.494(2) . ? C200 H20D 0.98 . ? C200 H20E 0.98 . ? C200 H20F 0.98 . ? C201 H20A 0.98 . ? C201 H20B 0.98 . ? C201 H20C 0.98 . ? C202 C203 1.530(2) . ? C202 H20G 0.99 . ? C202 H20H 0.99 . ? C203 C204 1.522(2) . ? C203 C205 1.524(2) . ? C203 H203 1 . ? C204 H20I 0.98 . ? C204 H20J 0.98 . ? C204 H20K 0.98 . ? C205 H20L 0.98 . ? C205 H20M 0.98 . ? C205 H20N 0.98 . ? C30 C31 1.375(4) . ? C30 C32B 1.384(3) 2_766 ? C30 C32A 1.384(3) 2_766 ? C30 H30 0.95 . ? C31 C32A 1.361(3) . ? C31 H31 0.95 . ? C32A C33 1.285(4) . ? C32A C30 1.384(3) 2_766 ? C33 H33A 0.98 . ? C33 H33B 0.98 . ? C33 H33C 0.98 . ? 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 C16 N10 C13 120.53(16) . . ? C16 N10 C102 117.63(17) . . ? C13 N10 C102 121.78(14) . . ? C17 N11 C14 117.49(16) . . ? C16 N12 C19 117.55(16) . . ? C18 N13 C19 126.55(16) . . ? C18 N13 H13 116.7 . . ? C19 N13 H13 116.7 . . ? C10 N100 C101 120.22(16) . . ? C10 N100 C100 120.98(17) . . ? C101 N100 C100 117.84(19) . . ? N100 C10 C15 122.53(18) . . ? N100 C10 C11 120.62(17) . . ? C15 C10 C11 116.83(19) . . ? C12 C11 C10 122.80(17) . . ? C12 C11 H11 118.6 . . ? C10 C11 H11 118.6 . . ? C11 C12 C13 120.38(18) . . ? C11 C12 H12 119.8 . . ? C13 C12 H12 119.8 . . ? N10 C13 C12 123.51(17) . . ? N10 C13 C14 118.58(16) . . ? C12 C13 C14 117.91(19) . . ? N11 C14 C15 117.50(16) . . ? N11 C14 C13 121.75(18) . . ? C15 C14 C13 120.74(16) . . ? C10 C15 C14 121.32(18) . . ? C10 C15 H15 119.3 . . ? C14 C15 H15 119.3 . . ? N12 C16 N10 117.77(16) . . ? N12 C16 C17 125.49(16) . . ? N10 C16 C17 116.74(18) . . ? N11 C17 C16 124.87(16) . . ? N11 C17 C18 118.17(16) . . ? C16 C17 C18 116.95(18) . . ? O18 C18 N13 122.75(16) . . ? O18 C18 C17 124.39(19) . . ? N13 C18 C17 112.85(16) . . ? O19 C19 N12 121.14(17) . . ? O19 C19 N13 118.27(16) . . ? N12 C19 N13 120.59(19) . . ? N100 C100 H10L 109.5 . . ? N100 C100 H10M 109.5 . . ? H10L C100 H10M 109.5 . . ? N100 C100 H10N 109.5 . . ? H10L C100 H10N 109.5 . . ? H10M C100 H10N 109.5 . . ? N100 C101 H10D 109.5 . . ? N100 C101 H10E 109.5 . . ? H10D C101 H10E 109.5 . . ? N100 C101 H10F 109.5 . . ? H10D C101 H10F 109.5 . . ? H10E C101 H10F 109.5 . . ? N10 C102 C103 112.06(13) . . ? N10 C102 H10J 109.2 . . ? C103 C102 H10J 109.2 . . ? N10 C102 H10K 109.2 . . ? C103 C102 H10K 109.2 . . ? H10J C102 H10K 107.9 . . ? C105 C103 C104 110.72(15) . . ? C105 C103 C102 112.91(17) . . ? C104 C103 C102 108.84(14) . . ? C105 C103 H103 108.1 . . ? C104 C103 H103 108.1 . . ? C102 C103 H103 108.1 . . ? C103 C104 H10G 109.5 . . ? C103 C104 H10H 109.5 . . ? H10G C104 H10H 109.5 . . ? C103 C104 H10I 109.5 . . ? H10G C104 H10I 109.5 . . ? H10H C104 H10I 109.5 . . ? C103 C105 H10A 109.5 . . ? C103 C105 H10B 109.5 . . ? H10A C105 H10B 109.5 . . ? C103 C105 H10C 109.5 . . ? H10A C105 H10C 109.5 . . ? H10B C105 H10C 109.5 . . ? C27 N20 C24 117.73(13) . . ? C26 N21 C23 120.71(12) . . ? C26 N21 C202 119.58(12) . . ? C23 N21 C202 119.61(12) . . ? C26 N22 C29 117.95(13) . . ? C28 N23 C29 125.82(13) . . ? C28 N23 H23 117.1 . . ? C29 N23 H23 117.1 . . ? C20 N200 C201 118.42(12) . . ? C20 N200 C200 119.64(13) . . ? C201 N200 C200 117.01(12) . . ? N200 C20 C25 122.49(14) . . ? N200 C20 C21 120.77(13) . . ? C25 C20 C21 116.73(14) . . ? C22 C21 C20 123.08(14) . . ? C22 C21 H21 118.5 . . ? C20 C21 H21 118.5 . . ? C21 C22 C23 120.28(14) . . ? C21 C22 H22 119.9 . . ? C23 C22 H22 119.9 . . ? N21 C23 C22 123.28(13) . . ? N21 C23 C24 118.89(13) . . ? C22 C23 C24 117.83(13) . . ? N20 C24 C25 117.56(13) . . ? N20 C24 C23 121.31(13) . . ? C25 C24 C23 121.08(14) . . ? C20 C25 C24 120.99(14) . . ? C20 C25 H25 119.5 . . ? C24 C25 H25 119.5 . . ? N22 C26 N21 118.99(13) . . ? N22 C26 C27 124.71(14) . . ? N21 C26 C27 116.29(13) . . ? N20 C27 C26 124.90(14) . . ? N20 C27 C28 118.00(13) . . ? C26 C27 C28 117.09(13) . . ? O28 C28 N23 123.58(14) . . ? O28 C28 C27 123.40(14) . . ? N23 C28 C27 113.02(13) . . ? O29 C29 N22 121.54(14) . . ? O29 C29 N23 117.91(14) . . ? N22 C29 N23 120.54(13) . . ? N200 C200 H20D 109.5 . . ? N200 C200 H20E 109.5 . . ? H20D C200 H20E 109.5 . . ? N200 C200 H20F 109.5 . . ? H20D C200 H20F 109.5 . . ? H20E C200 H20F 109.5 . . ? N200 C201 H20A 109.5 . . ? N200 C201 H20B 109.5 . . ? H20A C201 H20B 109.5 . . ? N200 C201 H20C 109.5 . . ? H20A C201 H20C 109.5 . . ? H20B C201 H20C 109.5 . . ? N21 C202 C203 114.24(12) . . ? N21 C202 H20G 108.7 . . ? C203 C202 H20G 108.7 . . ? N21 C202 H20H 108.7 . . ? C203 C202 H20H 108.7 . . ? H20G C202 H20H 107.6 . . ? C204 C203 C205 111.42(13) . . ? C204 C203 C202 112.46(13) . . ? C205 C203 C202 108.07(13) . . ? C204 C203 H203 108.3 . . ? C205 C203 H203 108.3 . . ? C202 C203 H203 108.3 . . ? C203 C204 H20I 109.5 . . ? C203 C204 H20J 109.5 . . ? H20I C204 H20J 109.5 . . ? C203 C204 H20K 109.5 . . ? H20I C204 H20K 109.5 . . ? H20J C204 H20K 109.5 . . ? C203 C205 H20L 109.5 . . ? C203 C205 H20M 109.5 . . ? H20L C205 H20M 109.5 . . ? C203 C205 H20N 109.5 . . ? H20L C205 H20N 109.5 . . ? H20M C205 H20N 109.5 . . ? C31 C30 C32B 120.3(2) . 2_766 ? C31 C30 C32A 120.3(2) . 2_766 ? C32B C30 C32A 0.0(3) 2_766 2_766 ? C31 C30 H30 119.9 . . ? C32B C30 H30 119.9 2_766 . ? C32A C30 H30 119.9 2_766 . ? C32A C31 C30 120.3(2) . . ? C32A C31 H31 119.8 . . ? C30 C31 H31 119.8 . . ? C33 C32A C31 119.8(3) . . ? C33 C32A C30 120.8(3) . 2_766 ? C31 C32A C30 119.4(3) . 2_766 ? # END of CIF