# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_cd212477 _database_code_depnum_ccdc_archive 'CCDC 902498' #TrackingRef 'cd212477.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H10 Br N3 O' _chemical_formula_weight 280.13 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 5.6282(9) _cell_length_b 9.0457(14) _cell_length_c 22.768(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1159.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2087 _cell_measurement_theta_min 4.845 _cell_measurement_theta_max 43.706 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.276 _exptl_crystal_size_mid 0.211 _exptl_crystal_size_min 0.143 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.605 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 560 _exptl_absorpt_coefficient_mu 3.528 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.42118 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6749 _diffrn_reflns_av_R_equivalents 0.0442 _diffrn_reflns_av_sigmaI/netI 0.0534 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.42 _diffrn_reflns_theta_max 25.49 _reflns_number_total 2154 _reflns_number_gt 1804 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0648P)^2^+0.3193P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.008(16) _chemical_absolute_configuration ad _refine_ls_number_reflns 2154 _refine_ls_number_parameters 149 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0557 _refine_ls_R_factor_gt 0.0462 _refine_ls_wR_factor_ref 0.1220 _refine_ls_wR_factor_gt 0.1173 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _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 Br1 Br -0.34735(14) 1.41914(7) 0.88430(3) 0.0927(3) Uani 1 1 d . . . N1 N 0.3261(6) 0.8464(4) 0.77585(15) 0.0374(7) Uani 1 1 d D . . N2 N 0.1313(5) 0.9013(3) 0.80990(13) 0.0327(7) Uani 1 1 d . . . N3 N 0.4310(9) 0.7416(5) 0.9250(2) 0.0668(12) Uani 1 1 d . . . O1 O 0.4860(6) 0.6346(3) 0.74116(15) 0.0531(8) Uani 1 1 d . . . C1 C 0.3347(8) 0.7011(4) 0.76897(18) 0.0387(9) Uani 1 1 d . . . C2 C 0.1194(8) 0.6368(5) 0.7988(2) 0.0452(10) Uani 1 1 d . . . H2A H 0.1638 0.5830 0.8340 0.054 Uiso 1 1 calc R . . H2B H 0.0340 0.5708 0.7727 0.054 Uiso 1 1 calc R . . C3 C -0.0289(7) 0.7712(5) 0.8138(2) 0.0427(10) Uani 1 1 d . . . H3A H -0.1596 0.7812 0.7863 0.051 Uiso 1 1 calc R . . H3B H -0.0935 0.7623 0.8531 0.051 Uiso 1 1 calc R . . C4 C 0.2239(7) 0.9556(4) 0.86668(16) 0.0327(9) Uani 1 1 d . . . H4 H 0.3445 1.0308 0.8582 0.039 Uiso 1 1 calc R . . C5 C 0.0266(7) 1.0297(4) 0.90075(16) 0.0332(8) Uani 1 1 d . . . C6 C -0.0719(9) 0.9675(5) 0.95050(19) 0.0466(11) Uani 1 1 d . . . H6 H -0.0126 0.8791 0.9653 0.056 Uiso 1 1 calc R . . C7 C -0.2594(9) 1.0378(5) 0.9780(2) 0.0501(11) Uani 1 1 d . . . H7 H -0.3279 0.9948 1.0110 0.060 Uiso 1 1 calc R . . C8 C -0.3455(9) 1.1685(5) 0.95785(19) 0.0500(11) Uani 1 1 d . . . H8 H -0.4728 1.2147 0.9763 0.060 Uiso 1 1 calc R . . C9 C -0.2393(9) 1.2311(5) 0.9093(2) 0.0464(11) Uani 1 1 d . . . C10 C -0.0552(8) 1.1647(5) 0.88055(19) 0.0430(10) Uani 1 1 d . . . H10 H 0.0142 1.2094 0.8480 0.052 Uiso 1 1 calc R . . C11 C 0.3408(8) 0.8361(5) 0.90099(17) 0.0413(10) Uani 1 1 d . . . H1 H 0.411(6) 0.910(3) 0.7607(16) 0.029(10) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.1179(6) 0.0670(4) 0.0933(5) 0.0179(3) 0.0289(4) 0.0560(4) N1 0.0393(19) 0.0271(16) 0.0457(19) 0.0011(14) 0.0108(16) 0.0033(16) N2 0.0308(16) 0.0333(16) 0.0341(17) -0.0013(13) 0.0052(13) 0.0102(15) N3 0.083(3) 0.047(2) 0.070(3) 0.005(2) -0.026(2) 0.016(2) O1 0.0513(18) 0.0441(16) 0.064(2) -0.0139(15) 0.0097(16) 0.0131(15) C1 0.039(2) 0.037(2) 0.040(2) -0.0077(16) -0.0003(19) 0.0043(19) C2 0.045(2) 0.037(2) 0.054(3) -0.0123(19) 0.000(2) -0.0102(19) C3 0.032(2) 0.045(2) 0.051(2) -0.014(2) 0.0014(18) -0.0039(19) C4 0.035(2) 0.0276(17) 0.035(2) -0.0010(15) -0.0022(16) -0.0013(16) C5 0.036(2) 0.0302(18) 0.033(2) -0.0052(15) -0.0029(17) 0.0000(17) C6 0.063(3) 0.036(2) 0.041(2) 0.0021(18) 0.006(2) 0.001(2) C7 0.056(3) 0.049(3) 0.046(3) -0.003(2) 0.014(2) -0.008(2) C8 0.043(2) 0.061(3) 0.047(3) -0.017(2) 0.011(2) -0.004(2) C9 0.058(3) 0.038(2) 0.043(2) -0.0024(19) -0.002(2) 0.015(2) C10 0.053(2) 0.041(2) 0.035(2) -0.0022(18) 0.005(2) 0.0118(19) C11 0.047(2) 0.039(2) 0.038(2) -0.0027(17) -0.007(2) 0.003(2) _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 Br1 C9 1.894(4) . ? N1 C1 1.325(5) . ? N1 N2 1.432(4) . ? N1 H1 0.821(19) . ? N2 C4 1.478(5) . ? N2 C3 1.485(5) . ? N3 C11 1.135(5) . ? O1 C1 1.219(5) . ? C1 C2 1.507(6) . ? C2 C3 1.513(6) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C11 1.487(6) . ? C4 C5 1.511(6) . ? C4 H4 0.9800 . ? C5 C6 1.381(6) . ? C5 C10 1.384(6) . ? C6 C7 1.383(7) . ? C6 H6 0.9300 . ? C7 C8 1.358(7) . ? C7 H7 0.9300 . ? C8 C9 1.379(7) . ? C8 H8 0.9300 . ? C9 C10 1.365(6) . ? C10 H10 0.9300 . ? 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 C1 N1 N2 115.9(3) . . ? C1 N1 H1 128(3) . . ? N2 N1 H1 116(3) . . ? N1 N2 C4 108.6(3) . . ? N1 N2 C3 102.8(3) . . ? C4 N2 C3 115.2(3) . . ? O1 C1 N1 125.2(4) . . ? O1 C1 C2 127.3(4) . . ? N1 C1 C2 107.5(4) . . ? C1 C2 C3 103.6(3) . . ? C1 C2 H2A 111.0 . . ? C3 C2 H2A 111.0 . . ? C1 C2 H2B 111.0 . . ? C3 C2 H2B 111.0 . . ? H2A C2 H2B 109.0 . . ? N2 C3 C2 106.8(3) . . ? N2 C3 H3A 110.4 . . ? C2 C3 H3A 110.4 . . ? N2 C3 H3B 110.4 . . ? C2 C3 H3B 110.4 . . ? H3A C3 H3B 108.6 . . ? N2 C4 C11 112.0(3) . . ? N2 C4 C5 109.7(3) . . ? C11 C4 C5 112.2(3) . . ? N2 C4 H4 107.6 . . ? C11 C4 H4 107.6 . . ? C5 C4 H4 107.6 . . ? C6 C5 C10 119.9(4) . . ? C6 C5 C4 122.4(4) . . ? C10 C5 C4 117.7(3) . . ? C5 C6 C7 119.4(4) . . ? C5 C6 H6 120.3 . . ? C7 C6 H6 120.3 . . ? C8 C7 C6 121.3(4) . . ? C8 C7 H7 119.3 . . ? C6 C7 H7 119.3 . . ? C7 C8 C9 118.3(4) . . ? C7 C8 H8 120.8 . . ? C9 C8 H8 120.8 . . ? C10 C9 C8 122.2(4) . . ? C10 C9 Br1 119.7(4) . . ? C8 C9 Br1 118.1(3) . . ? C9 C10 C5 118.8(4) . . ? C9 C10 H10 120.6 . . ? C5 C10 H10 120.6 . . ? N3 C11 C4 177.1(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 N1 N2 C4 109.2(4) . . . . ? C1 N1 N2 C3 -13.2(5) . . . . ? N2 N1 C1 O1 179.5(4) . . . . ? N2 N1 C1 C2 2.3(5) . . . . ? O1 C1 C2 C3 -167.6(4) . . . . ? N1 C1 C2 C3 9.5(5) . . . . ? N1 N2 C3 C2 18.2(4) . . . . ? C4 N2 C3 C2 -99.7(4) . . . . ? C1 C2 C3 N2 -17.2(4) . . . . ? N1 N2 C4 C11 -61.0(4) . . . . ? C3 N2 C4 C11 53.6(4) . . . . ? N1 N2 C4 C5 173.7(3) . . . . ? C3 N2 C4 C5 -71.6(4) . . . . ? N2 C4 C5 C6 109.1(4) . . . . ? C11 C4 C5 C6 -16.0(5) . . . . ? N2 C4 C5 C10 -71.0(4) . . . . ? C11 C4 C5 C10 163.9(4) . . . . ? C10 C5 C6 C7 3.1(6) . . . . ? C4 C5 C6 C7 -177.0(4) . . . . ? C5 C6 C7 C8 -1.4(7) . . . . ? C6 C7 C8 C9 -0.7(7) . . . . ? C7 C8 C9 C10 1.3(7) . . . . ? C7 C8 C9 Br1 -176.2(4) . . . . ? C8 C9 C10 C5 0.4(7) . . . . ? Br1 C9 C10 C5 177.8(3) . . . . ? C6 C5 C10 C9 -2.6(6) . . . . ? C4 C5 C10 C9 177.5(4) . . . . ? N2 C4 C11 N3 20(10) . . . . ? C5 C4 C11 N3 144(10) . . . . ? 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 H1 O1 0.821(19) 2.12(3) 2.840(4) 147(4) 3_656 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.49 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.719 _refine_diff_density_min -0.746 _refine_diff_density_rms 0.070 data_cd212479 _database_code_depnum_ccdc_archive 'CCDC 902501' #TrackingRef 'cd212479.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H10 Br N3 O' _chemical_formula_weight 280.13 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 5.5927(10) _cell_length_b 9.9073(17) _cell_length_c 11.448(2) _cell_angle_alpha 113.882(4) _cell_angle_beta 91.874(4) _cell_angle_gamma 99.063(4) _cell_volume 569.50(18) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1064 _cell_measurement_theta_min 4.577 _cell_measurement_theta_max 44.165 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.265 _exptl_crystal_size_mid 0.145 _exptl_crystal_size_min 0.112 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.634 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 280 _exptl_absorpt_coefficient_mu 3.591 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.36709 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3448 _diffrn_reflns_av_R_equivalents 0.0186 _diffrn_reflns_av_sigmaI/netI 0.0567 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2757 _reflns_number_gt 2043 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0404P)^2^+0.0000P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.006(7) _chemical_absolute_configuration ad _refine_ls_number_reflns 2757 _refine_ls_number_parameters 324 _refine_ls_number_restraints 44 _refine_ls_R_factor_all 0.0523 _refine_ls_R_factor_gt 0.0355 _refine_ls_wR_factor_ref 0.0880 _refine_ls_wR_factor_gt 0.0814 _refine_ls_goodness_of_fit_ref 0.947 _refine_ls_restrained_S_all 0.947 _refine_ls_shift/su_max 0.001 _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 Br1 Br 0.72132(11) 1.37024(6) 1.37563(6) 0.0815(3) Uani 1 1 d . A . Br1' Br 0.40691(9) -0.56708(5) 0.10809(5) 0.0808(3) Uani 1 1 d . . . N1 N 0.2415(12) 0.7774(7) 0.7765(6) 0.0586(17) Uani 1 1 d D A . N2 N 0.4359(11) 0.7269(6) 0.8203(5) 0.0526(14) Uani 1 1 d . A . N3 N -0.0504(15) 0.6057(8) 0.9497(7) 0.076(2) Uani 1 1 d . . . N1' N 0.8340(12) 0.0047(7) 0.7126(6) 0.0606(17) Uani 1 1 d D B . N2' N 0.6121(10) 0.0508(6) 0.6878(5) 0.0577(16) Uani 1 1 d D . . N3' N 0.2321(13) 0.1822(8) 0.5478(8) 0.0707(18) Uani 1 1 d . . . O1 O -0.0510(11) 0.7053(7) 0.6091(6) 0.0696(16) Uani 1 1 d . A . O1' O 1.1321(12) 0.0682(7) 0.8722(6) 0.083(2) Uani 1 1 d . B . C1 C 0.1184(13) 0.6806(7) 0.6678(7) 0.0524(17) Uani 1 1 d . . . C2 C 0.187(3) 0.5281(14) 0.6391(14) 0.058(4) Uani 0.65 1 d PU A 1 H2A H 0.0675 0.4663 0.6652 0.069 Uiso 0.65 1 calc PR A 1 H2B H 0.2039 0.4747 0.5486 0.069 Uiso 0.65 1 calc PR A 1 C2A C 0.275(5) 0.567(4) 0.610(3) 0.062(8) Uani 0.35 1 d PU A 2 H2A1 H 0.1764 0.4680 0.5637 0.075 Uiso 0.35 1 calc PR A 2 H2A2 H 0.3751 0.5925 0.5517 0.075 Uiso 0.35 1 calc PR A 2 C3 C 0.4252(15) 0.5734(9) 0.7196(8) 0.066(2) Uani 1 1 d . . . H3A H 0.4389 0.5041 0.7588 0.080 Uiso 0.65 1 calc PR A 1 H3B H 0.5581 0.5722 0.6671 0.080 Uiso 0.65 1 calc PR A 1 H3C H 0.3623 0.5011 0.7523 0.080 Uiso 0.35 1 d PR A 2 H3D H 0.5857 0.5609 0.6955 0.080 Uiso 0.35 1 d PR A 2 C4 C 0.3975(11) 0.7292(6) 0.9472(6) 0.0457(15) Uani 1 1 d . . . H4 H 0.5079 0.6703 0.9644 0.055 Uiso 1 1 calc R A . C5 C 0.4652(13) 0.8900(7) 1.0516(7) 0.0458(16) Uani 1 1 d . A . C6 C 0.3144(14) 0.9544(9) 1.1424(7) 0.0580(19) Uani 1 1 d . . . H6 H 0.1593 0.9021 1.1396 0.070 Uiso 1 1 calc R A . C7 C 0.3925(15) 1.0947(9) 1.2365(7) 0.064(2) Uani 1 1 d . A . H7 H 0.2897 1.1362 1.2983 0.077 Uiso 1 1 calc R . . C8 C 0.6200(16) 1.1775(9) 1.2432(8) 0.063(2) Uani 1 1 d . . . C9 C 0.7684(15) 1.1132(9) 1.1508(9) 0.070(2) Uani 1 1 d . A . H9 H 0.9215 1.1670 1.1524 0.084 Uiso 1 1 calc R . . C10 C 0.6927(14) 0.9686(8) 1.0548(8) 0.063(2) Uani 1 1 d . . . H10 H 0.7953 0.9256 0.9935 0.076 Uiso 1 1 calc R A . C11 C 0.1478(12) 0.6597(6) 0.9521(6) 0.0546(15) Uani 1 1 d . A . C1' C 0.9572(15) 0.0918(8) 0.8226(8) 0.061(2) Uani 1 1 d . . . C2' C 0.801(3) 0.2169(18) 0.8990(14) 0.058(4) Uani 0.55 1 d PDU B 1 H2'1 H 0.6932 0.1852 0.9516 0.070 Uiso 0.55 1 calc PR B 1 H2'2 H 0.9041 0.3128 0.9519 0.070 Uiso 0.55 1 calc PR B 1 C3' C 0.662(4) 0.222(2) 0.7852(19) 0.058(6) Uani 0.55 1 d PDU B 1 H3'1 H 0.7590 0.2842 0.7506 0.070 Uiso 0.55 1 calc PR B 1 H3'2 H 0.5110 0.2580 0.8079 0.070 Uiso 0.55 1 calc PR B 1 C2" C 0.888(4) 0.239(2) 0.855(2) 0.062(6) Uani 0.45 1 d PDU B 2 H2"1 H 0.9719 0.2929 0.8096 0.074 Uiso 0.45 1 calc PR B 2 H2"2 H 0.9135 0.3014 0.9470 0.074 Uiso 0.45 1 calc PR B 2 C3" C 0.618(4) 0.182(3) 0.806(3) 0.063(7) Uani 0.45 1 d PDU B 2 H3"1 H 0.5284 0.1555 0.8673 0.075 Uiso 0.45 1 calc PR B 2 H3"2 H 0.5473 0.2572 0.7905 0.075 Uiso 0.45 1 calc PR B 2 C4' C 0.6046(12) 0.0570(6) 0.5606(6) 0.0504(16) Uani 1 1 d . B . H4' H 0.7562 0.1178 0.5550 0.060 Uiso 1 1 calc R . . C5' C 0.5658(12) -0.0963(7) 0.4514(6) 0.0475(17) Uani 1 1 d . . . C6' C 0.7275(15) -0.1372(9) 0.3626(8) 0.0545(17) Uani 1 1 d . B . H6' H 0.8690 -0.0692 0.3707 0.065 Uiso 1 1 calc R . . C7' C 0.6861(16) -0.2777(11) 0.2605(9) 0.069(2) Uani 1 1 d . . . H7' H 0.7988 -0.3053 0.2012 0.083 Uiso 1 1 calc R B . C8' C 0.4767(15) -0.3737(7) 0.2497(7) 0.053(2) Uani 1 1 d . B . C9' C 0.3092(15) -0.3384(8) 0.3364(7) 0.064(2) Uani 1 1 d . . . H9' H 0.1676 -0.4067 0.3272 0.076 Uiso 1 1 calc R B . C10' C 0.3566(13) -0.1981(7) 0.4381(7) 0.0589(18) Uani 1 1 d . B . H10' H 0.2457 -0.1720 0.4986 0.071 Uiso 1 1 calc R . . C11' C 0.3977(11) 0.1309(6) 0.5542(6) 0.0532(14) Uani 1 1 d . . . H1' H 0.848(18) -0.082(4) 0.666(7) 0.12(4) Uiso 1 1 d D . . H1 H 0.275(12) 0.868(3) 0.798(6) 0.048(19) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0920(6) 0.0563(5) 0.0697(6) 0.0047(4) -0.0221(5) 0.0053(4) Br1' 0.1043(7) 0.0567(5) 0.0606(5) -0.0002(4) -0.0124(5) 0.0290(4) N1 0.075(4) 0.046(4) 0.055(4) 0.020(3) -0.007(3) 0.020(3) N2 0.060(3) 0.039(3) 0.053(3) 0.013(2) 0.003(3) 0.013(2) N3 0.071(5) 0.054(4) 0.089(5) 0.018(4) 0.011(4) 0.006(3) N1' 0.071(4) 0.044(4) 0.052(4) 0.000(3) 0.002(3) 0.028(3) N2' 0.065(4) 0.053(3) 0.049(3) 0.009(3) 0.007(3) 0.029(3) N3' 0.063(4) 0.053(4) 0.088(5) 0.018(3) -0.003(3) 0.020(3) O1 0.071(4) 0.064(3) 0.067(4) 0.018(3) -0.010(3) 0.024(3) O1' 0.086(4) 0.057(3) 0.079(4) -0.003(3) -0.024(3) 0.031(3) C1 0.063(4) 0.037(3) 0.049(4) 0.010(3) 0.003(3) 0.009(3) C2 0.060(9) 0.041(6) 0.068(8) 0.014(5) 0.006(6) 0.021(6) C2A 0.052(14) 0.070(15) 0.064(14) 0.024(11) 0.011(11) 0.021(11) C3 0.069(5) 0.053(5) 0.061(5) 0.003(4) 0.003(4) 0.027(4) C4 0.046(4) 0.041(3) 0.050(4) 0.016(3) -0.003(3) 0.015(3) C5 0.050(4) 0.037(3) 0.047(4) 0.012(3) -0.004(3) 0.014(3) C6 0.038(4) 0.065(5) 0.062(5) 0.018(4) -0.001(3) 0.010(3) C7 0.056(5) 0.061(4) 0.049(4) -0.002(3) -0.009(3) 0.005(4) C8 0.065(6) 0.063(6) 0.063(5) 0.024(4) 0.002(4) 0.024(4) C9 0.048(4) 0.053(5) 0.100(7) 0.025(5) -0.005(4) 0.004(3) C10 0.051(5) 0.055(5) 0.079(5) 0.021(4) 0.019(4) 0.014(4) C11 0.054(4) 0.045(3) 0.064(4) 0.022(3) 0.002(3) 0.010(3) C1' 0.067(5) 0.045(4) 0.068(5) 0.017(4) 0.008(4) 0.019(3) C2' 0.066(9) 0.042(7) 0.047(8) -0.005(5) 0.005(7) 0.022(7) C3' 0.082(12) 0.034(9) 0.051(10) 0.002(7) 0.010(8) 0.030(8) C2" 0.064(12) 0.039(9) 0.054(11) -0.009(8) 0.010(9) 0.006(8) C3" 0.074(13) 0.055(14) 0.066(12) 0.023(9) 0.009(9) 0.036(10) C4' 0.048(4) 0.036(3) 0.058(4) 0.011(3) 0.001(3) 0.007(3) C5' 0.049(4) 0.049(4) 0.050(4) 0.022(3) 0.007(3) 0.018(3) C6' 0.048(4) 0.045(4) 0.062(4) 0.013(3) 0.011(3) 0.011(3) C7' 0.067(5) 0.073(6) 0.070(5) 0.027(4) 0.021(4) 0.025(4) C8' 0.064(5) 0.036(4) 0.045(4) 0.004(3) -0.013(4) 0.012(3) C9' 0.060(5) 0.039(4) 0.072(5) 0.004(3) 0.006(4) 0.004(3) C10' 0.058(4) 0.043(4) 0.068(4) 0.014(3) 0.022(3) 0.009(3) C11' 0.053(4) 0.037(3) 0.060(4) 0.013(3) -0.001(3) 0.006(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 Br1 C8 1.877(9) . ? Br1' C8' 1.913(7) . ? N1 C1 1.309(9) . ? N1 N2 1.421(8) . ? N1 H1 0.82(2) . ? N2 C4 1.467(8) . ? N2 C3 1.481(9) . ? N3 C11 1.147(9) . ? N1' C1' 1.297(10) . ? N1' N2' 1.446(7) . ? N1' H1' 0.83(2) . ? N2' C3" 1.44(3) . ? N2' C4' 1.482(9) . ? N2' C3' 1.58(2) . ? N3' C11' 1.138(8) . ? O1 C1 1.254(9) . ? O1' C1' 1.215(9) . ? C1 C2A 1.48(3) . ? C1 C2 1.524(15) . ? C2 C3 1.493(16) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C2A C3 1.46(3) . ? C2A H2A1 0.9700 . ? C2A H2A2 0.9700 . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C3 H3C 0.9602 . ? C3 H3D 0.9599 . ? C4 C11 1.470(10) . ? C4 C5 1.533(9) . ? C4 H4 0.9800 . ? C5 C10 1.374(10) . ? C5 C6 1.374(9) . ? C6 C7 1.360(11) . ? C6 H6 0.9300 . ? C7 C8 1.383(11) . ? C7 H7 0.9300 . ? C8 C9 1.375(11) . ? C9 C10 1.394(11) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C1' C2" 1.47(2) . ? C1' C2' 1.606(16) . ? C2' C3' 1.518(16) . ? C2' H2'1 0.9700 . ? C2' H2'2 0.9700 . ? C3' H3'1 0.9700 . ? C3' H3'2 0.9700 . ? C2" C3" 1.530(18) . ? C2" H2"1 0.9700 . ? C2" H2"2 0.9700 . ? C3" H3"1 0.9700 . ? C3" H3"2 0.9700 . ? C4' C11' 1.479(9) . ? C4' C5' 1.503(9) . ? C4' H4' 0.9800 . ? C5' C6' 1.363(11) . ? C5' C10' 1.379(9) . ? C6' C7' 1.386(12) . ? C6' H6' 0.9300 . ? C7' C8' 1.355(12) . ? C7' H7' 0.9300 . ? C8' C9' 1.367(11) . ? C9' C10' 1.382(10) . ? C9' H9' 0.9300 . ? C10' H10' 0.9300 . ? 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 C1 N1 N2 114.9(6) . . ? C1 N1 H1 125(5) . . ? N2 N1 H1 110(5) . . ? N1 N2 C4 109.7(5) . . ? N1 N2 C3 103.5(5) . . ? C4 N2 C3 112.9(6) . . ? C1' N1' N2' 114.4(6) . . ? C1' N1' H1' 127(7) . . ? N2' N1' H1' 117(7) . . ? C3" N2' N1' 100.4(10) . . ? C3" N2' C4' 122.5(10) . . ? N1' N2' C4' 109.8(5) . . ? C3" N2' C3' 21.1(14) . . ? N1' N2' C3' 101.7(9) . . ? C4' N2' C3' 103.3(8) . . ? O1 C1 N1 125.2(7) . . ? O1 C1 C2A 126.3(14) . . ? N1 C1 C2A 105.0(14) . . ? O1 C1 C2 126.3(8) . . ? N1 C1 C2 107.7(8) . . ? C2A C1 C2 28.7(10) . . ? C3 C2 C1 101.3(9) . . ? C3 C2 H2A 111.5 . . ? C1 C2 H2A 111.5 . . ? C3 C2 H2B 111.5 . . ? C1 C2 H2B 111.5 . . ? H2A C2 H2B 109.3 . . ? C3 C2A C1 104.7(19) . . ? C3 C2A H2A1 110.8 . . ? C1 C2A H2A1 110.8 . . ? C3 C2A H2A2 110.8 . . ? C1 C2A H2A2 110.8 . . ? H2A1 C2A H2A2 108.9 . . ? C2A C3 N2 104.7(14) . . ? C2A C3 C2 29.3(10) . . ? N2 C3 C2 107.7(7) . . ? C2A C3 H3A 134.7 . . ? N2 C3 H3A 110.2 . . ? C2 C3 H3A 110.2 . . ? C2A C3 H3B 84.8 . . ? N2 C3 H3B 110.2 . . ? C2 C3 H3B 110.2 . . ? H3A C3 H3B 108.5 . . ? C2A C3 H3C 114.7 . . ? N2 C3 H3C 109.4 . . ? C2 C3 H3C 86.9 . . ? H3A C3 H3C 25.5 . . ? H3B C3 H3C 128.8 . . ? C2A C3 H3D 108.7 . . ? N2 C3 H3D 109.4 . . ? C2 C3 H3D 130.5 . . ? H3A C3 H3D 86.2 . . ? H3B C3 H3D 24.9 . . ? H3C C3 H3D 109.8 . . ? N2 C4 C11 112.3(5) . . ? N2 C4 C5 110.5(5) . . ? C11 C4 C5 111.2(6) . . ? N2 C4 H4 107.5 . . ? C11 C4 H4 107.5 . . ? C5 C4 H4 107.5 . . ? C10 C5 C6 119.9(7) . . ? C10 C5 C4 116.8(7) . . ? C6 C5 C4 123.2(7) . . ? C7 C6 C5 119.9(8) . . ? C7 C6 H6 120.1 . . ? C5 C6 H6 120.1 . . ? C6 C7 C8 122.0(8) . . ? C6 C7 H7 119.0 . . ? C8 C7 H7 119.0 . . ? C9 C8 C7 117.8(8) . . ? C9 C8 Br1 121.7(7) . . ? C7 C8 Br1 120.6(7) . . ? C8 C9 C10 121.0(8) . . ? C8 C9 H9 119.5 . . ? C10 C9 H9 119.5 . . ? C5 C10 C9 119.4(7) . . ? C5 C10 H10 120.3 . . ? C9 C10 H10 120.3 . . ? N3 C11 C4 176.3(7) . . ? O1' C1' N1' 127.0(7) . . ? O1' C1' C2" 126.0(10) . . ? N1' C1' C2" 104.9(10) . . ? O1' C1' C2' 123.8(9) . . ? N1' C1' C2' 107.7(8) . . ? C2" C1' C2' 28.9(8) . . ? C3' C2' C1' 99.0(13) . . ? C3' C2' H2'1 112.0 . . ? C1' C2' H2'1 112.0 . . ? C3' C2' H2'2 112.0 . . ? C1' C2' H2'2 112.0 . . ? H2'1 C2' H2'2 109.6 . . ? C2' C3' N2' 101.3(12) . . ? C2' C3' H3'1 111.5 . . ? N2' C3' H3'1 111.5 . . ? C2' C3' H3'2 111.5 . . ? N2' C3' H3'2 111.5 . . ? H3'1 C3' H3'2 109.3 . . ? C1' C2" C3" 97.3(15) . . ? C1' C2" H2"1 112.3 . . ? C3" C2" H2"1 112.3 . . ? C1' C2" H2"2 112.3 . . ? C3" C2" H2"2 112.3 . . ? H2"1 C2" H2"2 109.9 . . ? N2' C3" C2" 105(2) . . ? N2' C3" H3"1 110.8 . . ? C2" C3" H3"1 110.8 . . ? N2' C3" H3"2 110.8 . . ? C2" C3" H3"2 110.8 . . ? H3"1 C3" H3"2 108.9 . . ? C11' C4' N2' 105.8(5) . . ? C11' C4' C5' 109.6(5) . . ? N2' C4' C5' 112.5(5) . . ? C11' C4' H4' 109.6 . . ? N2' C4' H4' 109.6 . . ? C5' C4' H4' 109.6 . . ? C6' C5' C10' 118.6(7) . . ? C6' C5' C4' 122.2(7) . . ? C10' C5' C4' 119.1(6) . . ? C5' C6' C7' 121.6(8) . . ? C5' C6' H6' 119.2 . . ? C7' C6' H6' 119.2 . . ? C8' C7' C6' 118.1(8) . . ? C8' C7' H7' 121.0 . . ? C6' C7' H7' 121.0 . . ? C7' C8' C9' 122.6(8) . . ? C7' C8' Br1' 119.7(7) . . ? C9' C8' Br1' 117.6(6) . . ? C8' C9' C10' 118.0(7) . . ? C8' C9' H9' 121.0 . . ? C10' C9' H9' 121.0 . . ? C5' C10' C9' 121.1(7) . . ? C5' C10' H10' 119.5 . . ? C9' C10' H10' 119.5 . . ? N3' C11' C4' 177.1(6) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 N1 N2 C4 -120.8(6) . . . . ? C1 N1 N2 C3 -0.1(8) . . . . ? C1' N1' N2' C3" -1.6(13) . . . . ? C1' N1' N2' C4' 128.7(6) . . . . ? C1' N1' N2' C3' 19.9(11) . . . . ? N2 N1 C1 O1 -176.0(7) . . . . ? N2 N1 C1 C2A -16.1(14) . . . . ? N2 N1 C1 C2 13.7(10) . . . . ? O1 C1 C2 C3 168.9(8) . . . . ? N1 C1 C2 C3 -20.9(11) . . . . ? C2A C1 C2 C3 68(3) . . . . ? O1 C1 C2A C3 -174.6(10) . . . . ? N1 C1 C2A C3 26(2) . . . . ? C2 C1 C2A C3 -74(3) . . . . ? C1 C2A C3 N2 -26(2) . . . . ? C1 C2A C3 C2 75(3) . . . . ? N1 N2 C3 C2A 16.4(14) . . . . ? C4 N2 C3 C2A 135.0(13) . . . . ? N1 N2 C3 C2 -13.9(9) . . . . ? C4 N2 C3 C2 104.7(9) . . . . ? C1 C2 C3 C2A -68(3) . . . . ? C1 C2 C3 N2 20.8(11) . . . . ? N1 N2 C4 C11 47.3(6) . . . . ? C3 N2 C4 C11 -67.6(7) . . . . ? N1 N2 C4 C5 -77.5(6) . . . . ? C3 N2 C4 C5 167.6(6) . . . . ? N2 C4 C5 C10 -53.0(8) . . . . ? C11 C4 C5 C10 -178.4(6) . . . . ? N2 C4 C5 C6 129.6(6) . . . . ? C11 C4 C5 C6 4.2(8) . . . . ? C10 C5 C6 C7 -1.1(11) . . . . ? C4 C5 C6 C7 176.3(7) . . . . ? C5 C6 C7 C8 1.1(12) . . . . ? C6 C7 C8 C9 -0.1(13) . . . . ? C6 C7 C8 Br1 -179.5(6) . . . . ? C7 C8 C9 C10 -0.8(13) . . . . ? Br1 C8 C9 C10 178.5(6) . . . . ? C6 C5 C10 C9 0.1(11) . . . . ? C4 C5 C10 C9 -177.4(7) . . . . ? C8 C9 C10 C5 0.9(12) . . . . ? N2 C4 C11 N3 -13(11) . . . . ? C5 C4 C11 N3 111(11) . . . . ? N2' N1' C1' O1' 170.6(8) . . . . ? N2' N1' C1' C2" -25.4(12) . . . . ? N2' N1' C1' C2' 4.6(11) . . . . ? O1' C1' C2' C3' 165.6(12) . . . . ? N1' C1' C2' C3' -27.9(15) . . . . ? C2" C1' C2' C3' 61(2) . . . . ? C1' C2' C3' N2' 37.3(17) . . . . ? C3" N2' C3' C2' 52(3) . . . . ? N1' N2' C3' C2' -36.3(16) . . . . ? C4' N2' C3' C2' -150.2(13) . . . . ? O1' C1' C2" C3" -156.9(15) . . . . ? N1' C1' C2" C3" 38.9(18) . . . . ? C2' C1' C2" C3" -61(2) . . . . ? N1' N2' C3" C2" 26.8(18) . . . . ? C4' N2' C3" C2" -94.9(17) . . . . ? C3' N2' C3" C2" -69(4) . . . . ? C1' C2" C3" N2' -40(2) . . . . ? C3" N2' C4' C11' -52.7(14) . . . . ? N1' N2' C4' C11' -169.9(5) . . . . ? C3' N2' C4' C11' -62.1(10) . . . . ? C3" N2' C4' C5' -172.3(12) . . . . ? N1' N2' C4' C5' 70.5(7) . . . . ? C3' N2' C4' C5' 178.3(10) . . . . ? C11' C4' C5' C6' 121.3(7) . . . . ? N2' C4' C5' C6' -121.4(7) . . . . ? C11' C4' C5' C10' -56.9(8) . . . . ? N2' C4' C5' C10' 60.4(8) . . . . ? C10' C5' C6' C7' -0.1(12) . . . . ? C4' C5' C6' C7' -178.3(7) . . . . ? C5' C6' C7' C8' 1.1(13) . . . . ? C6' C7' C8' C9' -1.4(13) . . . . ? C6' C7' C8' Br1' 178.4(6) . . . . ? C7' C8' C9' C10' 0.6(12) . . . . ? Br1' C8' C9' C10' -179.2(6) . . . . ? C6' C5' C10' C9' -0.7(11) . . . . ? C4' C5' C10' C9' 177.6(7) . . . . ? C8' C9' C10' C5' 0.5(12) . . . . ? N2' C4' C11' N3' -82(14) . . . . ? C5' C4' C11' N3' 39(14) . . . . ? 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' H1' O1 0.83(2) 2.11(4) 2.902(8) 159(9) 1_645 N1 H1 O1' 0.82(2) 2.12(4) 2.814(9) 143(6) 1_465 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.332 _refine_diff_density_min -0.344 _refine_diff_density_rms 0.058