# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_coden_cambridge 182 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name 'Jason J. Shiers' 'Guy J. Clarkson' 'Michael Shipman' 'Jerome F. Hayes' _publ_contact_author_name 'Mike Shipman' _publ_contact_author_address ; Department of Chemistry University of Warwick Gibbet Hill Road Coventry CV4 7AL UNITED KINGDOM ; _publ_contact_author_email M.SHIPMAN@WARWICK.AC.UK _publ_requested_journal 'Chemical Communications' _publ_section_title ; Rapid Generation of Molecular Complexity using Hybrid Multi-Component Reactions (MCRs): Application to the Synthesis of ?-Amino Nitriles and 1,2-Diamines ; data_js1 _database_code_depnum_ccdc_archive 'CCDC 286808' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H22 N2 O' _chemical_formula_weight 246.35 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.149(6) _cell_length_b 10.559(5) _cell_length_c 11.588(6) _cell_angle_alpha 90.00 _cell_angle_beta 100.508(8) _cell_angle_gamma 90.00 _cell_volume 1341.3(12) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 5555 _cell_measurement_theta_min 2.62 _cell_measurement_theta_max 29.12 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.220 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 536 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7642 _exptl_absorpt_correction_T_max 0.9863 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; The temperature of the crystal was controlled using the Oxford Cryosystem Cryostream Cooler (Cosier & Glazer, 1986). The data collection nominally covered over a hemisphere of Reciprocal space, by a combination of three sets of exposures with different \f angles for the crystal; each 10 s exposure covered 0.3\% in \w. The crystal-to-detector distance was 5.0 cm. Coverage of the unique Set is over 97% complete to at least 26\% in \q. Crystal decay was found to be negligible by by repeating the initial frames at the end of data collection and analyzing the duplicate reflections. Hydrogen atoms were added at calculated positions and refined using a riding model. Anisotropic displacement parameters were used for all non-H atoms; H-atoms were given isotropic displacement parameter equal to 1.2 (or 1.5 for methyl H-atoms) times the equivalent isotropic displacement parameter of the atom to which they are attached. ; _diffrn_ambient_temperature 180(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 'Siemens SMART diffractometer' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8.192 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% nil _diffrn_reflns_number 8760 _diffrn_reflns_av_R_equivalents 0.0453 _diffrn_reflns_av_sigmaI/netI 0.0486 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.33 _diffrn_reflns_theta_max 29.13 _reflns_number_total 3310 _reflns_number_gt 2810 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Siemens, 1994)' _computing_cell_refinement 'SAINT (Siemens, 1995)' _computing_data_reduction 'SAINT (Siemens, 1995)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 1997)' _computing_publication_material 'SHELXTL (Sheldrick, 1997)' _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^)+(0.0857P)^2^+0.2130P] 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 3310 _refine_ls_number_parameters 170 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0548 _refine_ls_R_factor_gt 0.0478 _refine_ls_wR_factor_ref 0.1415 _refine_ls_wR_factor_gt 0.1354 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _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 N1 N 0.92514(10) 0.03612(9) 0.35434(9) 0.0278(2) Uani 1 1 d . . . H1A H 0.9659(15) -0.0249(16) 0.4001(14) 0.042 Uiso 1 1 d . . . H1B H 0.9015(16) 0.0302(16) 0.2766(15) 0.042 Uiso 1 1 d . . . O2 O 0.95259(8) 0.17376(8) 0.50687(7) 0.0294(2) Uani 1 1 d . . . C2 C 0.91319(10) 0.14980(10) 0.40247(9) 0.0219(2) Uani 1 1 d . . . C3 C 0.83681(9) 0.24697(10) 0.31916(9) 0.0199(2) Uani 1 1 d . . . N4 N 0.86678(8) 0.22486(9) 0.20080(7) 0.0208(2) Uani 1 1 d . . . C5 C 0.99338(10) 0.26701(11) 0.19907(10) 0.0241(2) Uani 1 1 d . . . H5A H 1.0112 0.2526 0.1195 0.029 Uiso 1 1 calc R . . H5B H 1.0503 0.2138 0.2544 0.029 Uiso 1 1 calc R . . C6 C 1.01808(11) 0.40585(11) 0.23165(11) 0.0301(3) Uani 1 1 d . . . H6A H 1.1042 0.4267 0.2293 0.036 Uiso 1 1 calc R . . H6B H 0.9652 0.4608 0.1745 0.036 Uiso 1 1 calc R . . C8 C 0.86422(10) 0.38307(10) 0.36414(9) 0.0237(2) Uani 1 1 d . . . H8A H 0.8033 0.4410 0.3189 0.028 Uiso 1 1 calc R . . H8B H 0.8549 0.3873 0.4474 0.028 Uiso 1 1 calc R . . C7 C 0.99232(11) 0.42947(11) 0.35434(11) 0.0292(3) Uani 1 1 d . . . H7A H 0.9991 0.5212 0.3720 0.035 Uiso 1 1 calc R . . H7B H 1.0537 0.3846 0.4126 0.035 Uiso 1 1 calc R . . C9 C 0.70093(10) 0.21461(11) 0.31951(10) 0.0242(2) Uani 1 1 d . . . H9A H 0.6494 0.2807 0.2745 0.029 Uiso 1 1 calc R . . H9B H 0.6815 0.1333 0.2778 0.029 Uiso 1 1 calc R . . C10 C 0.66625(12) 0.20408(13) 0.44056(11) 0.0338(3) Uani 1 1 d . . . H10A H 0.5783 0.1894 0.4318 0.051 Uiso 1 1 calc R . . H10B H 0.6877 0.2829 0.4842 0.051 Uiso 1 1 calc R . . H10C H 0.7105 0.1333 0.4835 0.051 Uiso 1 1 calc R . . C11 C 0.77878(10) 0.27653(11) 0.10145(9) 0.0252(2) Uani 1 1 d . . . H11A H 0.7797 0.3702 0.1057 0.030 Uiso 1 1 calc R . . H11B H 0.6956 0.2473 0.1070 0.030 Uiso 1 1 calc R . . C12 C 0.80914(10) 0.23499(11) -0.01495(9) 0.0232(2) Uani 1 1 d . . . C13 C 0.84210(11) 0.10997(11) -0.03354(10) 0.0294(3) Uani 1 1 d . . . H13A H 0.8463 0.0498 0.0280 0.035 Uiso 1 1 calc R . . C14 C 0.86875(12) 0.07273(13) -0.14056(11) 0.0350(3) Uani 1 1 d . . . H14A H 0.8923 -0.0123 -0.1515 0.042 Uiso 1 1 calc R . . C15 C 0.86116(12) 0.15911(14) -0.23205(11) 0.0354(3) Uani 1 1 d . . . H15A H 0.8788 0.1334 -0.3057 0.042 Uiso 1 1 calc R . . C16 C 0.82778(12) 0.28277(14) -0.21498(11) 0.0343(3) Uani 1 1 d . . . H16A H 0.8221 0.3422 -0.2773 0.041 Uiso 1 1 calc R . . C17 C 0.80249(11) 0.32059(11) -0.10685(10) 0.0287(3) Uani 1 1 d . . . H17A H 0.7804 0.4060 -0.0958 0.034 Uiso 1 1 calc R . . 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 N1 0.0370(5) 0.0215(5) 0.0237(5) 0.0016(4) 0.0027(4) 0.0046(4) O2 0.0390(5) 0.0282(4) 0.0197(4) 0.0014(3) 0.0020(3) 0.0061(3) C2 0.0233(5) 0.0223(5) 0.0209(5) 0.0023(4) 0.0057(4) 0.0010(4) C3 0.0228(5) 0.0206(5) 0.0166(5) 0.0005(4) 0.0046(4) 0.0016(4) N4 0.0211(4) 0.0250(5) 0.0166(4) 0.0005(3) 0.0043(3) 0.0022(3) C5 0.0225(5) 0.0271(6) 0.0237(5) 0.0016(4) 0.0068(4) 0.0015(4) C6 0.0288(6) 0.0280(6) 0.0352(6) 0.0032(5) 0.0099(5) -0.0041(4) C8 0.0276(5) 0.0205(5) 0.0228(5) -0.0012(4) 0.0043(4) 0.0017(4) C7 0.0304(6) 0.0240(5) 0.0322(6) -0.0017(5) 0.0033(5) -0.0038(4) C9 0.0227(5) 0.0271(5) 0.0235(5) -0.0009(4) 0.0063(4) 0.0001(4) C10 0.0318(6) 0.0444(7) 0.0282(6) 0.0000(5) 0.0135(5) -0.0027(5) C11 0.0268(5) 0.0294(6) 0.0190(5) 0.0005(4) 0.0033(4) 0.0061(4) C12 0.0227(5) 0.0272(5) 0.0192(5) 0.0000(4) 0.0025(4) 0.0004(4) C13 0.0358(6) 0.0278(6) 0.0251(6) 0.0004(4) 0.0064(5) 0.0018(5) C14 0.0379(7) 0.0353(7) 0.0318(6) -0.0092(5) 0.0065(5) 0.0041(5) C15 0.0318(6) 0.0532(8) 0.0220(6) -0.0076(5) 0.0067(5) -0.0015(5) C16 0.0357(6) 0.0461(7) 0.0211(6) 0.0059(5) 0.0056(5) -0.0036(5) C17 0.0327(6) 0.0291(6) 0.0234(6) 0.0025(4) 0.0027(5) 0.0000(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 N1 C2 1.3405(15) . ? N1 H1A 0.903(18) . ? N1 H1B 0.894(17) . ? O2 C2 1.2356(14) . ? C2 C3 1.5525(15) . ? C3 N4 1.4881(14) . ? C3 C8 1.5401(16) . ? C3 C9 1.5537(16) . ? N4 C11 1.4743(14) . ? N4 C5 1.4835(15) . ? C5 C6 1.5263(18) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.5215(18) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C8 C7 1.5336(17) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C9 C10 1.5256(16) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.5142(16) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C17 1.3884(16) . ? C12 C13 1.3975(17) . ? C13 C14 1.3839(17) . ? C13 H13A 0.9500 . ? C14 C15 1.389(2) . ? C14 H14A 0.9500 . ? C15 C16 1.382(2) . ? C15 H15A 0.9500 . ? C16 C17 1.3921(17) . ? C16 H16A 0.9500 . ? C17 H17A 0.9500 . ? 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 C2 N1 H1A 118.2(10) . . ? C2 N1 H1B 116.7(11) . . ? H1A N1 H1B 124.5(15) . . ? O2 C2 N1 123.11(10) . . ? O2 C2 C3 122.03(10) . . ? N1 C2 C3 114.70(10) . . ? N4 C3 C8 113.22(8) . . ? N4 C3 C2 106.23(8) . . ? C8 C3 C2 110.71(9) . . ? N4 C3 C9 110.54(8) . . ? C8 C3 C9 109.74(8) . . ? C2 C3 C9 106.11(9) . . ? C11 N4 C5 112.19(9) . . ? C11 N4 C3 115.61(9) . . ? C5 N4 C3 109.85(8) . . ? N4 C5 C6 114.46(9) . . ? N4 C5 H5A 108.6 . . ? C6 C5 H5A 108.6 . . ? N4 C5 H5B 108.6 . . ? C6 C5 H5B 108.6 . . ? H5A C5 H5B 107.6 . . ? C7 C6 C5 109.41(9) . . ? C7 C6 H6A 109.8 . . ? C5 C6 H6A 109.8 . . ? C7 C6 H6B 109.8 . . ? C5 C6 H6B 109.8 . . ? H6A C6 H6B 108.2 . . ? C7 C8 C3 113.77(9) . . ? C7 C8 H8A 108.8 . . ? C3 C8 H8A 108.8 . . ? C7 C8 H8B 108.8 . . ? C3 C8 H8B 108.8 . . ? H8A C8 H8B 107.7 . . ? C6 C7 C8 110.73(9) . . ? C6 C7 H7A 109.5 . . ? C8 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? C8 C7 H7B 109.5 . . ? H7A C7 H7B 108.1 . . ? C10 C9 C3 115.42(9) . . ? C10 C9 H9A 108.4 . . ? C3 C9 H9A 108.4 . . ? C10 C9 H9B 108.4 . . ? C3 C9 H9B 108.4 . . ? H9A C9 H9B 107.5 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N4 C11 C12 111.31(9) . . ? N4 C11 H11A 109.4 . . ? C12 C11 H11A 109.4 . . ? N4 C11 H11B 109.4 . . ? C12 C11 H11B 109.4 . . ? H11A C11 H11B 108.0 . . ? C17 C12 C13 118.38(11) . . ? C17 C12 C11 120.36(11) . . ? C13 C12 C11 121.25(10) . . ? C14 C13 C12 120.80(11) . . ? C14 C13 H13A 119.6 . . ? C12 C13 H13A 119.6 . . ? C13 C14 C15 120.27(12) . . ? C13 C14 H14A 119.9 . . ? C15 C14 H14A 119.9 . . ? C16 C15 C14 119.45(12) . . ? C16 C15 H15A 120.3 . . ? C14 C15 H15A 120.3 . . ? C15 C16 C17 120.26(12) . . ? C15 C16 H16A 119.9 . . ? C17 C16 H16A 119.9 . . ? C12 C17 C16 120.83(12) . . ? C12 C17 H17A 119.6 . . ? C16 C17 H17A 119.6 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1B N4 0.894(17) 2.241(17) 2.6717(16) 109.2(13) . N1 H1A O2 0.903(18) 2.025(18) 2.9251(16) 174.6(16) 3_756 _diffrn_measured_fraction_theta_max 0.919 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.340 _refine_diff_density_min -0.301 _refine_diff_density_rms 0.053 # Attachment 'JS3.CIF' data_js3 _database_code_depnum_ccdc_archive 'CCDC 286809' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H30 N2 O' _chemical_formula_weight 350.49 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 27.33(2) _cell_length_b 13.742(10) _cell_length_c 11.347(8) _cell_angle_alpha 90.00 _cell_angle_beta 101.470(13) _cell_angle_gamma 90.00 _cell_volume 4176(5) _cell_formula_units_Z 8 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 7286 _cell_measurement_theta_min 2.281 _cell_measurement_theta_max 26.824 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.115 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1520 _exptl_absorpt_coefficient_mu 0.068 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8185 _exptl_absorpt_correction_T_max 0.9879 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; The temperature of the crystal was controlled using the Oxford Cryosystem Cryostream Cooler (Cosier & Glazer, 1986). The data collection nominally covered over a hemisphere of Reciprocal space, by a combination of three sets of exposures with different \f angles for the crystal; each 10 s exposure covered 0.3\% in \w. The crystal-to-detector distance was 5.0 cm. Coverage of the unique Set is over 97% complete to at least 26\% in \q. Crystal decay was found to be negligible by by repeating the initial frames at the end of data collection and analyzing the duplicate reflections. Hydrogen atoms were added at calculated positions and refined using a riding model. Anisotropic displacement parameters were used for all non-H atoms; H-atoms were given isotropic displacement parameter equal to 1.2 (or 1.5 for methyl H-atoms) times the equivalent isotropic displacement parameter of the atom to which they are attached. ; _diffrn_ambient_temperature 180(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 'Siemens SMART diffractometer' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8.192 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% nil _diffrn_reflns_number 26328 _diffrn_reflns_av_R_equivalents 0.0747 _diffrn_reflns_av_sigmaI/netI 0.1010 _diffrn_reflns_limit_h_min -36 _diffrn_reflns_limit_h_max 35 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 29.17 _reflns_number_total 10240 _reflns_number_gt 5389 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Siemens, 1994)' _computing_cell_refinement 'SAINT (Siemens, 1995)' _computing_data_reduction 'SAINT (Siemens, 1995)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 1997)' _computing_publication_material 'SHELXTL (Sheldrick, 1997)' _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^)+(0.0921P)^2^+1.0608P] 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 10240 _refine_ls_number_parameters 477 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1525 _refine_ls_R_factor_gt 0.0772 _refine_ls_wR_factor_ref 0.2203 _refine_ls_wR_factor_gt 0.1880 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.012 _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 C101 C 0.12308(11) 0.1929(2) 0.3747(2) 0.0572(7) Uani 1 1 d . . . H10A H 0.1036 0.1494 0.4115 0.069 Uiso 1 1 calc R . . C102 C 0.17381(12) 0.1993(3) 0.4183(3) 0.0760(10) Uani 1 1 d . . . H10B H 0.1889 0.1587 0.4832 0.091 Uiso 1 1 calc R . . C103 C 0.20311(12) 0.2636(3) 0.3696(3) 0.0786(10) Uani 1 1 d . . . H10C H 0.2379 0.2682 0.4012 0.094 Uiso 1 1 calc R . . C104 C 0.18090(11) 0.3209(3) 0.2742(3) 0.0722(9) Uani 1 1 d . . . H10D H 0.2004 0.3661 0.2399 0.087 Uiso 1 1 calc R . . C105 C 0.13023(10) 0.3126(2) 0.2285(2) 0.0578(8) Uani 1 1 d . . . H10E H 0.1156 0.3515 0.1615 0.069 Uiso 1 1 calc R . . C106 C 0.10009(9) 0.24905(18) 0.2775(2) 0.0419(6) Uani 1 1 d . . . C107 C 0.04445(9) 0.24078(17) 0.2281(2) 0.0401(6) Uani 1 1 d . . . H10F H 0.0396 0.2106 0.1474 0.048 Uiso 1 1 calc R . . H10G H 0.0301 0.1959 0.2804 0.048 Uiso 1 1 calc R . . N108 N 0.01602(7) 0.33179(14) 0.21763(16) 0.0377(5) Uani 1 1 d . . . O109 O 0.02948(6) 0.37587(12) 0.03111(13) 0.0418(4) Uani 1 1 d . . . C109 C 0.01183(8) 0.39222(16) 0.12214(19) 0.0349(5) Uani 1 1 d . . . N110 N -0.01401(8) 0.47191(16) 0.14238(18) 0.0439(5) Uani 1 1 d . . . H110 H -0.0214(11) 0.517(2) 0.089(3) 0.066 Uiso 1 1 d . . . C111 C -0.03276(10) 0.46503(18) 0.2513(2) 0.0441(6) Uani 1 1 d . . . H11E H -0.0695 0.4573 0.2339 0.053 Uiso 1 1 calc R . . H11F H -0.0238 0.5235 0.3019 0.053 Uiso 1 1 calc R . . C112 C -0.00664(9) 0.37281(17) 0.31405(19) 0.0375(5) Uani 1 1 d . . . C113 C -0.04458(9) 0.30316(18) 0.3527(2) 0.0428(6) Uani 1 1 d . . . H11G H -0.0258 0.2520 0.4041 0.051 Uiso 1 1 calc R . . H11H H -0.0638 0.3402 0.4032 0.051 Uiso 1 1 calc R . . C114 C -0.08184(10) 0.2532(2) 0.2526(2) 0.0538(7) Uani 1 1 d . . . H11I H -0.0986 0.3030 0.1954 0.065 Uiso 1 1 calc R . . H11J H -0.0636 0.2085 0.2080 0.065 Uiso 1 1 calc R . . C115 C -0.12083(10) 0.1964(2) 0.3018(3) 0.0559(7) Uani 1 1 d . . . C116 C -0.17033(13) 0.2255(3) 0.2823(4) 0.0983(13) Uani 1 1 d . . . H11A H -0.1807 0.2811 0.2340 0.118 Uiso 1 1 calc R . . C117 C -0.20500(15) 0.1742(4) 0.3326(6) 0.1237(18) Uani 1 1 d . . . H11B H -0.2388 0.1949 0.3189 0.148 Uiso 1 1 calc R . . C118 C -0.19029(17) 0.0931(3) 0.4025(5) 0.1078(15) Uani 1 1 d . . . H11C H -0.2140 0.0580 0.4366 0.129 Uiso 1 1 calc R . . C119 C -0.14200(14) 0.0637(3) 0.4224(3) 0.0789(10) Uani 1 1 d . . . H11D H -0.1319 0.0078 0.4704 0.095 Uiso 1 1 calc R . . C120 C -0.10731(12) 0.1152(2) 0.3727(3) 0.0651(8) Uani 1 1 d . . . H12B H -0.0735 0.0942 0.3879 0.078 Uiso 1 1 calc R . . C121 C 0.03449(9) 0.39715(17) 0.4240(2) 0.0401(6) Uani 1 1 d . . . H12F H 0.0179 0.4200 0.4890 0.048 Uiso 1 1 calc R . . H12G H 0.0520 0.3358 0.4521 0.048 Uiso 1 1 calc R . . C122 C 0.07390(10) 0.4722(2) 0.4095(2) 0.0499(7) Uani 1 1 d . . . H12H H 0.0589 0.5380 0.4056 0.060 Uiso 1 1 calc R . . H12I H 0.0849 0.4603 0.3327 0.060 Uiso 1 1 calc R . . C123 C 0.11924(11) 0.4686(2) 0.5128(3) 0.0652(8) Uani 1 1 d . . . H12J H 0.1076 0.4774 0.5894 0.078 Uiso 1 1 calc R . . H12K H 0.1344 0.4031 0.5145 0.078 Uiso 1 1 calc R . . C124 C 0.15886(13) 0.5431(3) 0.5069(4) 0.0876(11) Uani 1 1 d . . . H12L H 0.1446 0.6091 0.5093 0.105 Uiso 1 1 calc R . . H12M H 0.1704 0.5361 0.4299 0.105 Uiso 1 1 calc R . . C125 C 0.20448(14) 0.5309(4) 0.6144(4) 0.1138(16) Uani 1 1 d . . . H12C H 0.2315 0.5744 0.6028 0.171 Uiso 1 1 calc R . . H12D H 0.2162 0.4633 0.6176 0.171 Uiso 1 1 calc R . . H12E H 0.1942 0.5472 0.6900 0.171 Uiso 1 1 calc R . . C201 C 0.38153(11) 0.1838(2) 0.2554(2) 0.0540(7) Uani 1 1 d . . . H20A H 0.4019 0.1440 0.3138 0.065 Uiso 1 1 calc R . . C202 C 0.33043(11) 0.1830(3) 0.2466(3) 0.0686(9) Uani 1 1 d . . . H20B H 0.3162 0.1410 0.2972 0.082 Uiso 1 1 calc R . . C203 C 0.29981(11) 0.2418(3) 0.1660(3) 0.0709(9) Uani 1 1 d . . . H20C H 0.2647 0.2411 0.1608 0.085 Uiso 1 1 calc R . . C204 C 0.32094(11) 0.3015(3) 0.0930(3) 0.0739(10) Uani 1 1 d . . . H20D H 0.3004 0.3437 0.0379 0.089 Uiso 1 1 calc R . . C205 C 0.37235(10) 0.3004(2) 0.0995(3) 0.0606(8) Uani 1 1 d . . . H20E H 0.3864 0.3408 0.0469 0.073 Uiso 1 1 calc R . . C206 C 0.40358(9) 0.24131(17) 0.1813(2) 0.0405(6) Uani 1 1 d . . . C207 C 0.45993(9) 0.23816(17) 0.1875(2) 0.0400(6) Uani 1 1 d . . . H20F H 0.4749 0.1948 0.2547 0.048 Uiso 1 1 calc R . . H20G H 0.4660 0.2081 0.1124 0.048 Uiso 1 1 calc R . . N208 N 0.48611(7) 0.33116(13) 0.20373(15) 0.0369(5) Uani 1 1 d . . . O209 O 0.47259(6) 0.37403(12) 0.00394(13) 0.0423(4) Uani 1 1 d . . . C209 C 0.48977(8) 0.39175(16) 0.11187(19) 0.0347(5) Uani 1 1 d . . . N210 N 0.51386(9) 0.47335(16) 0.15607(17) 0.0465(6) Uani 1 1 d . . . H210 H 0.5201(11) 0.519(2) 0.114(3) 0.070 Uiso 1 1 d . . . C211 C 0.53287(10) 0.46726(18) 0.2832(2) 0.0452(6) Uani 1 1 d . . . H21E H 0.5235 0.5255 0.3250 0.054 Uiso 1 1 calc R . . H21F H 0.5697 0.4609 0.3008 0.054 Uiso 1 1 calc R . . C212 C 0.50771(9) 0.37406(17) 0.32185(19) 0.0377(5) Uani 1 1 d . . . C213 C 0.54614(9) 0.30668(18) 0.3978(2) 0.0431(6) Uani 1 1 d . . . H21G H 0.5278 0.2541 0.4300 0.052 Uiso 1 1 calc R . . H21H H 0.5641 0.3445 0.4675 0.052 Uiso 1 1 calc R . . C214 C 0.58557(10) 0.2588(2) 0.3354(2) 0.0552(7) Uani 1 1 d . . . H21I H 0.5686 0.2153 0.2704 0.066 Uiso 1 1 calc R . . H21J H 0.6032 0.3100 0.2986 0.066 Uiso 1 1 calc R . . C215 C 0.62290(10) 0.2011(2) 0.4234(3) 0.0573(7) Uani 1 1 d . . . C216 C 0.67136(14) 0.2322(3) 0.4603(4) 0.1016(13) Uani 1 1 d . . . H21A H 0.6820 0.2900 0.4270 0.122 Uiso 1 1 calc R . . C217 C 0.70526(17) 0.1805(5) 0.5459(6) 0.139(2) Uani 1 1 d . . . H21B H 0.7386 0.2029 0.5703 0.167 Uiso 1 1 calc R . . C218 C 0.6898(2) 0.0967(4) 0.5945(5) 0.1197(17) Uani 1 1 d . . . H21C H 0.7124 0.0619 0.6544 0.144 Uiso 1 1 calc R . . C219 C 0.64258(16) 0.0641(3) 0.5567(4) 0.0937(12) Uani 1 1 d . . . H21D H 0.6324 0.0050 0.5881 0.112 Uiso 1 1 calc R . . C220 C 0.60910(12) 0.1158(2) 0.4732(3) 0.0675(9) Uani 1 1 d . . . H22A H 0.5759 0.0925 0.4492 0.081 Uiso 1 1 calc R . . C221 C 0.46594(10) 0.39636(17) 0.3900(2) 0.0415(6) Uani 1 1 d . . . H22E H 0.4493 0.3342 0.4022 0.050 Uiso 1 1 calc R . . H22F H 0.4816 0.4212 0.4706 0.050 Uiso 1 1 calc R . . C222 C 0.42551(10) 0.4686(2) 0.3336(2) 0.0499(7) Uani 1 1 d . . . H22G H 0.4154 0.4550 0.2465 0.060 Uiso 1 1 calc R . . H22H H 0.4392 0.5354 0.3431 0.060 Uiso 1 1 calc R . . C223 C 0.37957(11) 0.4624(2) 0.3918(3) 0.0623(8) Uani 1 1 d . . . H22I H 0.3664 0.3952 0.3824 0.075 Uiso 1 1 calc R . . H22J H 0.3902 0.4751 0.4790 0.075 Uiso 1 1 calc R . . C224 C 0.33761(13) 0.5323(3) 0.3409(4) 0.0900(11) Uani 1 1 d . . . H22K H 0.3271 0.5217 0.2532 0.108 Uiso 1 1 calc R . . H22L H 0.3497 0.6001 0.3539 0.108 Uiso 1 1 calc R . . C225 C 0.29169(15) 0.5168(4) 0.4030(5) 0.1204(17) Uani 1 1 d . . . H22B H 0.2653 0.5633 0.3700 0.181 Uiso 1 1 calc R . . H22C H 0.3021 0.5272 0.4899 0.181 Uiso 1 1 calc R . . H22D H 0.2790 0.4503 0.3879 0.181 Uiso 1 1 calc R . . 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 C101 0.0601(17) 0.0637(19) 0.0480(16) 0.0176(14) 0.0110(13) 0.0052(15) C102 0.067(2) 0.094(3) 0.063(2) 0.0387(19) 0.0019(16) 0.0114(19) C103 0.0506(17) 0.112(3) 0.071(2) 0.024(2) 0.0061(16) 0.0106(19) C104 0.0565(18) 0.095(3) 0.067(2) 0.0297(18) 0.0169(16) 0.0014(17) C105 0.0556(17) 0.072(2) 0.0470(16) 0.0241(14) 0.0130(13) 0.0078(15) C106 0.0552(15) 0.0410(14) 0.0317(12) 0.0016(10) 0.0138(11) 0.0065(12) C107 0.0569(15) 0.0358(13) 0.0287(12) 0.0021(10) 0.0112(11) 0.0071(11) N108 0.0553(12) 0.0346(11) 0.0247(9) 0.0030(8) 0.0112(8) 0.0087(9) O109 0.0571(10) 0.0435(10) 0.0260(8) 0.0016(7) 0.0110(7) 0.0087(8) C109 0.0426(13) 0.0344(13) 0.0266(11) 0.0010(9) 0.0041(9) 0.0011(10) N110 0.0622(13) 0.0416(12) 0.0312(11) 0.0105(9) 0.0169(9) 0.0166(11) C111 0.0608(16) 0.0415(14) 0.0322(12) 0.0032(11) 0.0147(11) 0.0108(12) C112 0.0556(14) 0.0330(12) 0.0263(11) 0.0019(9) 0.0142(10) 0.0073(11) C113 0.0545(15) 0.0419(14) 0.0332(12) 0.0038(11) 0.0118(11) 0.0054(12) C114 0.0597(17) 0.0576(17) 0.0420(15) 0.0029(13) 0.0048(12) 0.0033(14) C115 0.0545(17) 0.0543(18) 0.0586(17) -0.0038(14) 0.0103(13) -0.0051(14) C116 0.064(2) 0.085(3) 0.141(4) 0.017(3) 0.011(2) 0.004(2) C117 0.058(2) 0.114(4) 0.201(6) 0.014(4) 0.033(3) -0.004(3) C118 0.090(3) 0.083(3) 0.160(5) 0.016(3) 0.047(3) -0.019(2) C119 0.086(3) 0.058(2) 0.097(3) 0.0070(18) 0.026(2) -0.0078(19) C120 0.0610(18) 0.061(2) 0.074(2) 0.0003(16) 0.0148(16) 0.0028(16) C121 0.0573(15) 0.0352(13) 0.0303(12) -0.0010(10) 0.0147(11) 0.0045(11) C122 0.0640(17) 0.0489(15) 0.0388(14) -0.0050(12) 0.0149(12) -0.0021(13) C123 0.0582(18) 0.077(2) 0.0634(19) -0.0262(16) 0.0181(15) -0.0091(16) C124 0.081(2) 0.101(3) 0.085(3) -0.027(2) 0.030(2) -0.025(2) C125 0.064(2) 0.155(4) 0.118(4) -0.053(3) 0.006(2) -0.023(3) C201 0.0623(17) 0.0581(18) 0.0410(14) 0.0116(13) 0.0090(13) 0.0014(14) C202 0.0601(19) 0.086(2) 0.0626(19) 0.0230(17) 0.0178(15) -0.0066(17) C203 0.0508(17) 0.095(3) 0.064(2) 0.0154(18) 0.0041(15) -0.0059(17) C204 0.0576(19) 0.096(3) 0.0610(19) 0.0304(18) -0.0066(15) -0.0039(18) C205 0.0565(17) 0.072(2) 0.0485(16) 0.0237(15) -0.0022(13) -0.0115(15) C206 0.0563(15) 0.0367(13) 0.0257(11) 0.0003(10) 0.0012(10) -0.0085(11) C207 0.0592(15) 0.0305(13) 0.0280(12) -0.0004(9) 0.0029(10) -0.0026(11) N208 0.0556(12) 0.0296(10) 0.0232(9) 0.0002(8) 0.0023(8) -0.0058(9) O209 0.0601(10) 0.0416(10) 0.0237(8) -0.0011(7) 0.0049(7) -0.0091(8) C209 0.0430(13) 0.0354(13) 0.0257(11) 0.0002(9) 0.0069(9) -0.0024(10) N210 0.0706(15) 0.0400(12) 0.0259(10) 0.0038(9) 0.0024(9) -0.0175(11) C211 0.0682(17) 0.0359(13) 0.0281(12) 0.0026(10) 0.0015(11) -0.0108(12) C212 0.0556(14) 0.0328(12) 0.0223(10) -0.0004(9) 0.0020(10) -0.0057(11) C213 0.0561(15) 0.0403(14) 0.0297(12) 0.0007(10) 0.0008(11) -0.0062(12) C214 0.0581(16) 0.0559(17) 0.0509(16) 0.0066(13) 0.0094(13) -0.0013(14) C215 0.0525(16) 0.0574(18) 0.0582(17) -0.0050(14) 0.0019(13) 0.0030(14) C216 0.071(2) 0.090(3) 0.135(4) 0.001(3) 0.000(2) -0.009(2) C217 0.066(3) 0.134(5) 0.189(6) -0.018(4) -0.046(3) 0.014(3) C218 0.106(4) 0.109(4) 0.123(4) 0.002(3) -0.028(3) 0.037(3) C219 0.103(3) 0.078(3) 0.093(3) 0.014(2) 0.001(2) 0.025(2) C220 0.0639(19) 0.062(2) 0.071(2) 0.0091(16) 0.0004(16) 0.0065(16) C221 0.0622(15) 0.0345(13) 0.0257(11) -0.0021(10) 0.0034(10) -0.0065(12) C222 0.0692(18) 0.0419(15) 0.0371(14) -0.0015(11) 0.0071(12) 0.0049(13) C223 0.0631(18) 0.0547(18) 0.0662(19) -0.0145(15) 0.0057(15) 0.0045(15) C224 0.082(2) 0.084(3) 0.102(3) -0.004(2) 0.014(2) 0.017(2) C225 0.076(3) 0.122(4) 0.169(5) -0.006(3) 0.040(3) 0.018(3) _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 C101 C102 1.379(4) . ? C101 C106 1.389(4) . ? C101 H10A 0.9500 . ? C102 C103 1.379(5) . ? C102 H10B 0.9500 . ? C103 C104 1.378(4) . ? C103 H10C 0.9500 . ? C104 C105 1.383(4) . ? C104 H10D 0.9500 . ? C105 C106 1.390(4) . ? C105 H10E 0.9500 . ? C106 C107 1.517(4) . ? C107 N108 1.465(3) . ? C107 H10F 0.9900 . ? C107 H10G 0.9900 . ? N108 C109 1.352(3) . ? N108 C112 1.472(3) . ? O109 C109 1.244(3) . ? C109 N110 1.347(3) . ? N110 C111 1.432(3) . ? N110 H110 0.86(3) . ? C111 C112 1.556(3) . ? C111 H11E 0.9900 . ? C111 H11F 0.9900 . ? C112 C113 1.538(3) . ? C112 C121 1.541(3) . ? C113 C114 1.530(4) . ? C113 H11G 0.9900 . ? C113 H11H 0.9900 . ? C114 C115 1.514(4) . ? C114 H11I 0.9900 . ? C114 H11J 0.9900 . ? C115 C120 1.382(4) . ? C115 C116 1.386(5) . ? C116 C117 1.392(6) . ? C116 H11A 0.9500 . ? C117 C118 1.380(6) . ? C117 H11B 0.9500 . ? C118 C119 1.355(5) . ? C118 H11C 0.9500 . ? C119 C120 1.390(5) . ? C119 H11D 0.9500 . ? C120 H12B 0.9500 . ? C121 C122 1.524(4) . ? C121 H12F 0.9900 . ? C121 H12G 0.9900 . ? C122 C123 1.528(4) . ? C122 H12H 0.9900 . ? C122 H12I 0.9900 . ? C123 C124 1.501(5) . ? C123 H12J 0.9900 . ? C123 H12K 0.9900 . ? C124 C125 1.570(6) . ? C124 H12L 0.9900 . ? C124 H12M 0.9900 . ? C125 H12C 0.9800 . ? C125 H12D 0.9800 . ? C125 H12E 0.9800 . ? C201 C206 1.377(4) . ? C201 C202 1.380(4) . ? C201 H20A 0.9500 . ? C202 C203 1.373(4) . ? C202 H20B 0.9500 . ? C203 C204 1.372(4) . ? C203 H20C 0.9500 . ? C204 C205 1.392(4) . ? C204 H20D 0.9500 . ? C205 C206 1.391(4) . ? C205 H20E 0.9500 . ? C206 C207 1.528(4) . ? C207 N208 1.458(3) . ? C207 H20F 0.9900 . ? C207 H20G 0.9900 . ? N208 C209 1.353(3) . ? N208 C212 1.476(3) . ? O209 C209 1.245(3) . ? C209 N210 1.346(3) . ? N210 C211 1.435(3) . ? N210 H210 0.83(3) . ? C211 C212 1.557(3) . ? C211 H21E 0.9900 . ? C211 H21F 0.9900 . ? C212 C213 1.531(3) . ? C212 C221 1.532(4) . ? C213 C214 1.549(4) . ? C213 H21G 0.9900 . ? C213 H21H 0.9900 . ? C214 C215 1.504(4) . ? C214 H21I 0.9900 . ? C214 H21J 0.9900 . ? C215 C216 1.375(5) . ? C215 C220 1.386(4) . ? C216 C217 1.395(6) . ? C216 H21A 0.9500 . ? C217 C218 1.379(7) . ? C217 H21B 0.9500 . ? C218 C219 1.354(6) . ? C218 H21C 0.9500 . ? C219 C220 1.377(5) . ? C219 H21D 0.9500 . ? C220 H22A 0.9500 . ? C221 C222 1.528(4) . ? C221 H22E 0.9900 . ? C221 H22F 0.9900 . ? C222 C223 1.533(4) . ? C222 H22G 0.9900 . ? C222 H22H 0.9900 . ? C223 C224 1.519(4) . ? C223 H22I 0.9900 . ? C223 H22J 0.9900 . ? C224 C225 1.571(6) . ? C224 H22K 0.9900 . ? C224 H22L 0.9900 . ? C225 H22B 0.9800 . ? C225 H22C 0.9800 . ? C225 H22D 0.9800 . ? 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 C102 C101 C106 120.9(3) . . ? C102 C101 H10A 119.6 . . ? C106 C101 H10A 119.6 . . ? C101 C102 C103 121.3(3) . . ? C101 C102 H10B 119.4 . . ? C103 C102 H10B 119.4 . . ? C104 C103 C102 118.7(3) . . ? C104 C103 H10C 120.6 . . ? C102 C103 H10C 120.6 . . ? C103 C104 C105 119.9(3) . . ? C103 C104 H10D 120.0 . . ? C105 C104 H10D 120.0 . . ? C104 C105 C106 122.0(3) . . ? C104 C105 H10E 119.0 . . ? C106 C105 H10E 119.0 . . ? C101 C106 C105 117.1(3) . . ? C101 C106 C107 120.9(2) . . ? C105 C106 C107 121.9(2) . . ? N108 C107 C106 116.3(2) . . ? N108 C107 H10F 108.2 . . ? C106 C107 H10F 108.2 . . ? N108 C107 H10G 108.2 . . ? C106 C107 H10G 108.2 . . ? H10F C107 H10G 107.4 . . ? C109 N108 C107 123.25(19) . . ? C109 N108 C112 112.29(19) . . ? C107 N108 C112 124.17(18) . . ? O109 C109 N110 126.2(2) . . ? O109 C109 N108 124.7(2) . . ? N110 C109 N108 109.1(2) . . ? C109 N110 C111 112.52(19) . . ? C109 N110 H110 122(2) . . ? C111 N110 H110 125(2) . . ? N110 C111 C112 103.80(19) . . ? N110 C111 H11E 111.0 . . ? C112 C111 H11E 111.0 . . ? N110 C111 H11F 111.0 . . ? C112 C111 H11F 111.0 . . ? H11E C111 H11F 109.0 . . ? N108 C112 C113 112.39(19) . . ? N108 C112 C121 109.8(2) . . ? C113 C112 C121 109.17(19) . . ? N108 C112 C111 101.19(17) . . ? C113 C112 C111 111.3(2) . . ? C121 C112 C111 112.8(2) . . ? C114 C113 C112 117.0(2) . . ? C114 C113 H11G 108.0 . . ? C112 C113 H11G 108.0 . . ? C114 C113 H11H 108.0 . . ? C112 C113 H11H 108.0 . . ? H11G C113 H11H 107.3 . . ? C115 C114 C113 111.7(2) . . ? C115 C114 H11I 109.3 . . ? C113 C114 H11I 109.3 . . ? C115 C114 H11J 109.3 . . ? C113 C114 H11J 109.3 . . ? H11I C114 H11J 107.9 . . ? C120 C115 C116 117.7(3) . . ? C120 C115 C114 120.3(3) . . ? C116 C115 C114 121.9(3) . . ? C115 C116 C117 120.7(4) . . ? C115 C116 H11A 119.6 . . ? C117 C116 H11A 119.6 . . ? C118 C117 C116 120.1(4) . . ? C118 C117 H11B 120.0 . . ? C116 C117 H11B 120.0 . . ? C119 C118 C117 120.0(4) . . ? C119 C118 H11C 120.0 . . ? C117 C118 H11C 120.0 . . ? C118 C119 C120 120.0(4) . . ? C118 C119 H11D 120.0 . . ? C120 C119 H11D 120.0 . . ? C115 C120 C119 121.5(3) . . ? C115 C120 H12B 119.2 . . ? C119 C120 H12B 119.2 . . ? C122 C121 C112 118.4(2) . . ? C122 C121 H12F 107.7 . . ? C112 C121 H12F 107.7 . . ? C122 C121 H12G 107.7 . . ? C112 C121 H12G 107.7 . . ? H12F C121 H12G 107.1 . . ? C121 C122 C123 112.2(2) . . ? C121 C122 H12H 109.2 . . ? C123 C122 H12H 109.2 . . ? C121 C122 H12I 109.2 . . ? C123 C122 H12I 109.2 . . ? H12H C122 H12I 107.9 . . ? C124 C123 C122 115.2(3) . . ? C124 C123 H12J 108.5 . . ? C122 C123 H12J 108.5 . . ? C124 C123 H12K 108.5 . . ? C122 C123 H12K 108.5 . . ? H12J C123 H12K 107.5 . . ? C123 C124 C125 111.1(4) . . ? C123 C124 H12L 109.4 . . ? C125 C124 H12L 109.4 . . ? C123 C124 H12M 109.4 . . ? C125 C124 H12M 109.4 . . ? H12L C124 H12M 108.0 . . ? C124 C125 H12C 109.5 . . ? C124 C125 H12D 109.5 . . ? H12C C125 H12D 109.5 . . ? C124 C125 H12E 109.5 . . ? H12C C125 H12E 109.5 . . ? H12D C125 H12E 109.5 . . ? C206 C201 C202 121.3(3) . . ? C206 C201 H20A 119.3 . . ? C202 C201 H20A 119.3 . . ? C203 C202 C201 121.1(3) . . ? C203 C202 H20B 119.4 . . ? C201 C202 H20B 119.4 . . ? C204 C203 C202 118.7(3) . . ? C204 C203 H20C 120.7 . . ? C202 C203 H20C 120.7 . . ? C203 C204 C205 120.2(3) . . ? C203 C204 H20D 119.9 . . ? C205 C204 H20D 119.9 . . ? C206 C205 C204 121.4(3) . . ? C206 C205 H20E 119.3 . . ? C204 C205 H20E 119.3 . . ? C201 C206 C205 117.2(2) . . ? C201 C206 C207 121.0(2) . . ? C205 C206 C207 121.8(2) . . ? N208 C207 C206 116.5(2) . . ? N208 C207 H20F 108.2 . . ? C206 C207 H20F 108.2 . . ? N208 C207 H20G 108.2 . . ? C206 C207 H20G 108.2 . . ? H20F C207 H20G 107.3 . . ? C209 N208 C207 123.47(18) . . ? C209 N208 C212 112.11(19) . . ? C207 N208 C212 124.22(17) . . ? O209 C209 N210 126.2(2) . . ? O209 C209 N208 124.5(2) . . ? N210 C209 N208 109.34(19) . . ? C209 N210 C211 112.24(19) . . ? C209 N210 H210 124(2) . . ? C211 N210 H210 123(2) . . ? N210 C211 C212 103.84(18) . . ? N210 C211 H21E 111.0 . . ? C212 C211 H21E 111.0 . . ? N210 C211 H21F 111.0 . . ? C212 C211 H21F 111.0 . . ? H21E C211 H21F 109.0 . . ? N208 C212 C213 112.06(19) . . ? N208 C212 C221 109.57(19) . . ? C213 C212 C221 109.47(19) . . ? N208 C212 C211 101.06(17) . . ? C213 C212 C211 111.3(2) . . ? C221 C212 C211 113.1(2) . . ? C212 C213 C214 117.5(2) . . ? C212 C213 H21G 107.9 . . ? C214 C213 H21G 107.9 . . ? C212 C213 H21H 107.9 . . ? C214 C213 H21H 107.9 . . ? H21G C213 H21H 107.2 . . ? C215 C214 C213 111.2(2) . . ? C215 C214 H21I 109.4 . . ? C213 C214 H21I 109.4 . . ? C215 C214 H21J 109.4 . . ? C213 C214 H21J 109.4 . . ? H21I C214 H21J 108.0 . . ? C216 C215 C220 117.5(3) . . ? C216 C215 C214 121.6(3) . . ? C220 C215 C214 120.9(3) . . ? C215 C216 C217 121.3(4) . . ? C215 C216 H21A 119.3 . . ? C217 C216 H21A 119.3 . . ? C218 C217 C216 119.4(4) . . ? C218 C217 H21B 120.3 . . ? C216 C217 H21B 120.3 . . ? C219 C218 C217 119.9(4) . . ? C219 C218 H21C 120.1 . . ? C217 C218 H21C 120.1 . . ? C218 C219 C220 120.5(4) . . ? C218 C219 H21D 119.7 . . ? C220 C219 H21D 119.7 . . ? C219 C220 C215 121.3(3) . . ? C219 C220 H22A 119.3 . . ? C215 C220 H22A 119.3 . . ? C222 C221 C212 117.9(2) . . ? C222 C221 H22E 107.8 . . ? C212 C221 H22E 107.8 . . ? C222 C221 H22F 107.8 . . ? C212 C221 H22F 107.8 . . ? H22E C221 H22F 107.2 . . ? C221 C222 C223 111.7(2) . . ? C221 C222 H22G 109.3 . . ? C223 C222 H22G 109.3 . . ? C221 C222 H22H 109.3 . . ? C223 C222 H22H 109.3 . . ? H22G C222 H22H 107.9 . . ? C224 C223 C222 115.0(3) . . ? C224 C223 H22I 108.5 . . ? C222 C223 H22I 108.5 . . ? C224 C223 H22J 108.5 . . ? C222 C223 H22J 108.5 . . ? H22I C223 H22J 107.5 . . ? C223 C224 C225 110.7(3) . . ? C223 C224 H22K 109.5 . . ? C225 C224 H22K 109.5 . . ? C223 C224 H22L 109.5 . . ? C225 C224 H22L 109.5 . . ? H22K C224 H22L 108.1 . . ? C224 C225 H22B 109.5 . . ? C224 C225 H22C 109.5 . . ? H22B C225 H22C 109.5 . . ? C224 C225 H22D 109.5 . . ? H22B C225 H22D 109.5 . . ? H22C C225 H22D 109.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N110 H110 O109 0.86(3) 1.99(3) 2.846(3) 173(3) 3_565 N210 H210 O209 0.83(3) 2.02(3) 2.846(3) 173(3) 3_665 _diffrn_measured_fraction_theta_max 0.907 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.326 _refine_diff_density_min -0.225 _refine_diff_density_rms 0.045