# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year 2011 #TrackingRef '- Global CIF with all 3 structures in one.cif' # Person for contact _publ_contact_author_name 'Prof. Dr. Jose G. Fernandez-Bolanos' _publ_contact_author_address ; Prof. Dr. Jos\'e G. Fern\'andez-Bola\~nos Departamento de Qu\'imica Org\'anica, Facultad de Qu\'imica, Universidad de Sevilla, c/Profesor Garc\'ia Gonz\'alez 1, E-41012, Seville, Spain ; _publ_contact_author_phone '+34 954550996' _publ_contact_author_fax '+34 954624960' _publ_contact_author_email bolanos@us.es _publ_author_address ; Departamento de Qu\'imica Org\'anica, Facultad de Qu\'imica, Universidad de Sevilla, c/Profesor Garc\'ia Gonz\'alez 1, E-41012, Seville, Spain Instituto de Investigaciones Qu\'imicas - Departamento de Qu\'imica Inorg\'anica, Consejo Superior de Investigaciones Cient\'ificas - Universidad de Sevilla, Avda. Am\'erico Vespucio s/n, 41092, Sevilla, Spain ; _publ_section_title ; Alkoxyamine-cyanoboranes: efficient cyanoborane transfer agents ; _journal_volume ? _journal_page_first ? _journal_page_last ? loop_ _publ_author_name J.M.Marquez E.Martinez-Castro O.Lopez "In\'es Maya" 'Manuel Angulo' ; E.Alvarez ; J.G.Fernandez-Bolanos #========================================================================= # Three crystal structures follow, separated/terminaed by #===END. #========================================================================= #=============================================================================80 # Data for compound 6 (local labelling ea09707a) #=============================================================================80 data_6 _database_code_depnum_ccdc_archive 'CCDC 816969' #TrackingRef '- Global CIF with all 3 structures in one.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C4 H10 B Cl N2 O' _chemical_formula_sum 'C4 H10 B Cl N2 O' _chemical_formula_weight 148.40 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' B B 0.0013 0.0007 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.2785(6) _cell_length_b 6.5034(6) _cell_length_c 9.6048(9) _cell_angle_alpha 83.088(3) _cell_angle_beta 87.368(4) _cell_angle_gamma 78.440(3) _cell_volume 381.34(6) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2149 _cell_measurement_theta_min 3.31 _cell_measurement_theta_max 29.78 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.292 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 156 _exptl_absorpt_coefficient_mu 0.424 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8171 _exptl_absorpt_correction_T_max 0.9276 _exptl_absorpt_process_details ; SADABS, Bruker (2006). APEX 2. Version 2.1. Bruker Analytical X-ray Solutions, Madison, Wisconsin, USA. ; _diffrn_ambient_temperature 173(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 ; Bruker-Nonius X8kappa APEX II CCD area detector' ; _diffrn_measurement_method 'phi and omega scans with narrow frames' _diffrn_detector_area_resol_mean 8.26 _diffrn_standards_decay_% 0 _diffrn_reflns_number 6575 _diffrn_reflns_av_R_equivalents 0.0335 _diffrn_reflns_av_sigmaI/netI 0.0445 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 30.59 _reflns_number_total 2301 _reflns_number_gt 1660 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker (2006). APEX 2. Version 2.1.' _computing_cell_refinement 'Bruker (2006). APEX 2. Version 2.1.' _computing_data_reduction 'Bruker (2006). APEX 2. Version 2.1.' _computing_structure_solution 'Bruker (2006). APEX 2. Version 2.1.' _computing_structure_refinement 'XL, SHELXTL v. 6.14 (Bruker, 2003)' _computing_molecular_graphics 'XP, SHELXTL v. 6.14 (Bruker, 2003)' _computing_publication_material 'XCIF, SHELXTL v. 6.14 (Bruker, 2003)' _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^)+(0.0455P)^2^+0.2800P] 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 2301 _refine_ls_number_parameters 92 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0566 _refine_ls_R_factor_gt 0.0405 _refine_ls_wR_factor_ref 0.1140 _refine_ls_wR_factor_gt 0.0956 _refine_ls_goodness_of_fit_ref 1.095 _refine_ls_restrained_S_all 1.095 _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 Cl1 Cl 0.38153(7) 1.25261(8) 0.11643(5) 0.02084(15) Uani 1 1 d . . . O1 O 0.7998(2) 0.9729(2) 0.38756(14) 0.0188(3) Uani 1 1 d . . . N1 N 0.7899(2) 0.9012(3) 0.25137(16) 0.0133(3) Uani 1 1 d . . . H1N H 0.674(4) 0.870(4) 0.252(2) 0.016 Uiso 1 1 d . . . N2 N 1.3711(3) 0.7546(3) 0.2688(2) 0.0247(4) Uani 1 1 d . . . C1 C 0.8131(3) 1.0873(3) 0.1512(2) 0.0171(4) Uani 1 1 d . . . H1A H 0.8068 1.0503 0.0547 0.021 Uiso 1 1 calc R . . H1B H 0.9585 1.1198 0.1621 0.021 Uiso 1 1 calc R . . C2 C 0.6428(3) 1.2841(3) 0.1683(2) 0.0195(4) Uani 1 1 d . . . H2A H 0.6851 1.4066 0.1101 0.023 Uiso 1 1 calc R . . H2B H 0.6345 1.3128 0.2675 0.023 Uiso 1 1 calc R . . C3 C 0.7681(4) 0.8167(4) 0.5008(2) 0.0268(5) Uani 1 1 d . . . H3A H 0.6398 0.7598 0.4836 0.040 Uiso 1 1 calc R . . H3B H 0.7466 0.8813 0.5888 0.040 Uiso 1 1 calc R . . H3C H 0.8964 0.7021 0.5076 0.040 Uiso 1 1 calc R . . C4 C 1.1987(3) 0.7309(3) 0.2519(2) 0.0173(4) Uani 1 1 d . . . B1 B 0.9629(3) 0.6926(3) 0.2246(2) 0.0166(4) Uani 1 1 d . . . H1 H 0.950(4) 0.676(4) 0.114(2) 0.020 Uiso 1 1 d . . . H2 H 0.921(4) 0.555(4) 0.299(2) 0.020 Uiso 1 1 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 Cl1 0.0135(2) 0.0195(3) 0.0289(3) -0.00032(19) -0.00499(17) -0.00205(16) O1 0.0223(7) 0.0193(7) 0.0152(7) -0.0023(5) -0.0017(5) -0.0047(5) N1 0.0088(7) 0.0169(8) 0.0148(7) -0.0008(6) -0.0015(5) -0.0041(6) N2 0.0137(8) 0.0212(9) 0.0390(11) -0.0052(8) -0.0011(7) -0.0023(6) C1 0.0107(8) 0.0179(10) 0.0218(9) 0.0033(8) -0.0002(7) -0.0040(7) C2 0.0134(9) 0.0163(10) 0.0288(11) 0.0015(8) -0.0060(7) -0.0042(7) C3 0.0331(12) 0.0283(12) 0.0172(10) 0.0036(9) -0.0019(8) -0.0049(9) C4 0.0145(9) 0.0125(9) 0.0240(10) -0.0017(8) -0.0006(7) -0.0005(7) B1 0.0101(9) 0.0158(11) 0.0241(11) -0.0028(9) -0.0022(8) -0.0024(7) _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 Cl1 C2 1.7930(19) . ? O1 C3 1.432(3) . ? O1 N1 1.448(2) . ? N1 C1 1.480(2) . ? N1 B1 1.598(3) . ? N1 H1N 0.79(2) . ? N2 C4 1.145(3) . ? C1 C2 1.515(3) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 B1 1.588(3) . ? B1 H1 1.09(2) . ? B1 H2 1.14(2) . ? 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 C3 O1 N1 112.64(15) . . ? O1 N1 C1 103.88(14) . . ? O1 N1 B1 115.05(14) . . ? C1 N1 B1 113.47(15) . . ? O1 N1 H1N 103.8(16) . . ? C1 N1 H1N 114.3(17) . . ? B1 N1 H1N 106.1(17) . . ? N1 C1 C2 114.72(15) . . ? N1 C1 H1A 108.6 . . ? C2 C1 H1A 108.6 . . ? N1 C1 H1B 108.6 . . ? C2 C1 H1B 108.6 . . ? H1A C1 H1B 107.6 . . ? C1 C2 Cl1 110.81(13) . . ? C1 C2 H2A 109.5 . . ? Cl1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? Cl1 C2 H2B 109.5 . . ? H2A C2 H2B 108.1 . . ? O1 C3 H3A 109.5 . . ? O1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? O1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? N2 C4 B1 178.0(2) . . ? C4 B1 N1 108.34(15) . . ? C4 B1 H1 109.4(12) . . ? N1 B1 H1 105.2(12) . . ? C4 B1 H2 111.5(12) . . ? N1 B1 H2 108.4(11) . . ? H1 B1 H2 113.7(16) . . ? 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 C3 O1 N1 C1 176.83(15) . . . . ? C3 O1 N1 B1 -58.5(2) . . . . ? O1 N1 C1 C2 -57.94(18) . . . . ? B1 N1 C1 C2 176.41(15) . . . . ? N1 C1 C2 Cl1 -69.56(19) . . . . ? O1 N1 B1 C4 -54.7(2) . . . . ? C1 N1 B1 C4 64.8(2) . . . . ? 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 H1N N2 0.79(2) 2.17(2) 2.962(2) 174(2) 1_455 _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.683 _refine_diff_density_min -0.386 _refine_diff_density_rms 0.082 ###END #=============================================================================80 # Data for compound 7 (local labelling ea09507a) #=============================================================================80 data_7 _database_code_depnum_ccdc_archive 'CCDC 816970' #TrackingRef '- Global CIF with all 3 structures in one.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H14 B Cl N2 O' _chemical_formula_sum 'C10 H14 B Cl N2 O' _chemical_formula_weight 224.49 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' B B 0.0013 0.0007 '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' Cl Cl 0.1484 0.1585 '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 _symmetry_space_group_name_Hall '-P 2ybc' 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 9.5051(4) _cell_length_b 12.3772(5) _cell_length_c 9.9685(4) _cell_angle_alpha 90.00 _cell_angle_beta 92.1500(10) _cell_angle_gamma 90.00 _cell_volume 1171.93(8) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 8972 _cell_measurement_theta_min 2.14 _cell_measurement_theta_max 30.15 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.272 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 472 _exptl_absorpt_coefficient_mu 0.300 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8643 _exptl_absorpt_correction_T_max 0.9341 _exptl_absorpt_process_details ; SADABS, Bruker (2006). APEX 2. Version 2.1. Bruker Analytical X-ray Solutions, Madison, Wisconsin, USA. ; _diffrn_ambient_temperature 173(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 ; Bruker-Nonius X8kappa APEX II CCD area detector' ; _diffrn_measurement_method 'phi and omega scans with narrow frames' _diffrn_detector_area_resol_mean 8.26 _diffrn_standards_decay_% 0 _diffrn_reflns_number 33074 _diffrn_reflns_av_R_equivalents 0.0320 _diffrn_reflns_av_sigmaI/netI 0.0202 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.44 _diffrn_reflns_theta_max 30.53 _reflns_number_total 3579 _reflns_number_gt 2931 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker (2006). APEX 2. Version 2.1.' _computing_cell_refinement 'Bruker (2006). APEX 2. Version 2.1.' _computing_data_reduction 'Bruker (2006). APEX 2. Version 2.1.' _computing_structure_solution 'Bruker (2006). APEX 2. Version 2.1.' _computing_structure_refinement 'XL, SHELXTL v. 6.14 (Bruker, 2003)' _computing_molecular_graphics 'XP, SHELXTL v. 6.14 (Bruker, 2003)' _computing_publication_material 'XCIF, SHELXTL v. 6.14 (Bruker, 2003)' _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^)+(0.0488P)^2^+0.2392P] 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 3579 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0412 _refine_ls_R_factor_gt 0.0317 _refine_ls_wR_factor_ref 0.0893 _refine_ls_wR_factor_gt 0.0851 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _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 Cl1 Cl 0.79235(3) 0.52089(2) 0.48279(3) 0.03210(9) Uani 1 1 d . . . O1 O 0.70929(7) 0.35193(5) 0.20057(7) 0.01640(14) Uani 1 1 d . . . N1 N 0.59125(8) 0.38557(6) 0.27833(8) 0.01484(15) Uani 1 1 d . . . H1N H 0.5886(13) 0.4580(10) 0.2776(12) 0.018 Uiso 1 1 d . . . N2 N 0.46293(10) 0.11886(7) 0.23018(9) 0.02569(19) Uani 1 1 d . . . C1 C 0.61907(10) 0.34972(8) 0.41908(10) 0.01996(18) Uani 1 1 d . . . H1A H 0.6077 0.2703 0.4228 0.024 Uiso 1 1 calc R . . H1B H 0.5469 0.3820 0.4758 0.024 Uiso 1 1 calc R . . C2 C 0.76253(11) 0.37828(8) 0.47855(10) 0.0234(2) Uani 1 1 d . . . H2A H 0.8355 0.3436 0.4249 0.028 Uiso 1 1 calc R . . H2B H 0.7717 0.3493 0.5710 0.028 Uiso 1 1 calc R . . C3 C 0.74473(11) 0.43683(8) 0.10788(11) 0.0243(2) Uani 1 1 d . . . H3A H 0.7730 0.5032 0.1574 0.029 Uiso 1 1 calc R . . H3B H 0.6630 0.4539 0.0472 0.029 Uiso 1 1 calc R . . C4 C 0.86477(10) 0.39487(7) 0.02923(10) 0.01834(18) Uani 1 1 d . . . C5 C 0.98548(10) 0.35517(8) 0.09572(10) 0.02067(19) Uani 1 1 d . . . H5 H 0.9928 0.3567 0.1910 0.025 Uiso 1 1 calc R . . C6 C 1.09517(10) 0.31328(8) 0.02354(10) 0.02167(19) Uani 1 1 d . . . H6 H 1.1759 0.2841 0.0694 0.026 Uiso 1 1 calc R . . C7 C 1.08654(10) 0.31407(8) -0.11578(11) 0.0222(2) Uani 1 1 d . . . H7 H 1.1612 0.2851 -0.1654 0.027 Uiso 1 1 calc R . . C8 C 0.96886(11) 0.35722(8) -0.18239(10) 0.0226(2) Uani 1 1 d . . . H8 H 0.9646 0.3602 -0.2777 0.027 Uiso 1 1 calc R . . C9 C 0.85703(10) 0.39619(8) -0.11050(10) 0.02069(19) Uani 1 1 d . . . H9 H 0.7754 0.4237 -0.1567 0.025 Uiso 1 1 calc R . . C10 C 0.45768(10) 0.21121(8) 0.22209(10) 0.01974(18) Uani 1 1 d . . . B1 B 0.44883(11) 0.33945(9) 0.21174(11) 0.0187(2) Uani 1 1 d . . . H1 H 0.3622(13) 0.3699(10) 0.2742(13) 0.022 Uiso 1 1 d . . . H2 H 0.4411(13) 0.3649(10) 0.1086(13) 0.022 Uiso 1 1 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 Cl1 0.03293(15) 0.02167(14) 0.04097(17) -0.00788(10) -0.00820(11) -0.00036(10) O1 0.0167(3) 0.0129(3) 0.0201(3) 0.0018(2) 0.0074(2) 0.0021(2) N1 0.0156(3) 0.0118(3) 0.0174(3) 0.0002(3) 0.0045(3) 0.0011(3) N2 0.0303(5) 0.0190(4) 0.0281(5) -0.0030(3) 0.0057(3) -0.0064(3) C1 0.0241(4) 0.0194(4) 0.0165(4) 0.0018(3) 0.0018(3) -0.0009(3) C2 0.0279(5) 0.0196(5) 0.0223(5) -0.0011(4) -0.0035(4) 0.0032(4) C3 0.0283(5) 0.0145(4) 0.0312(5) 0.0070(4) 0.0151(4) 0.0035(3) C4 0.0195(4) 0.0116(4) 0.0243(5) 0.0013(3) 0.0068(3) -0.0012(3) C5 0.0240(5) 0.0177(4) 0.0205(4) 0.0022(3) 0.0032(3) -0.0010(3) C6 0.0174(4) 0.0192(4) 0.0285(5) 0.0004(4) 0.0007(3) -0.0011(3) C7 0.0189(4) 0.0194(4) 0.0288(5) -0.0057(4) 0.0071(4) -0.0026(3) C8 0.0240(5) 0.0238(5) 0.0203(5) -0.0052(4) 0.0027(3) -0.0037(4) C9 0.0187(4) 0.0183(4) 0.0251(5) 0.0001(3) 0.0011(3) -0.0015(3) C10 0.0190(4) 0.0204(4) 0.0201(4) -0.0025(3) 0.0051(3) -0.0044(3) B1 0.0165(4) 0.0161(5) 0.0235(5) -0.0001(4) 0.0012(4) -0.0008(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 Cl1 C2 1.7879(11) . ? O1 C3 1.4474(11) . ? O1 N1 1.4485(9) . ? N1 C1 1.4858(12) . ? N1 B1 1.5911(13) . ? N1 H1N 0.897(13) . ? N2 C10 1.1468(13) . ? C1 C2 1.5084(14) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.5011(13) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C9 1.3922(14) . ? C4 C5 1.3929(14) . ? C5 C6 1.3891(14) . ? C5 H5 0.9500 . ? C6 C7 1.3882(15) . ? C6 H6 0.9500 . ? C7 C8 1.3862(15) . ? C7 H7 0.9500 . ? C8 C9 1.3904(14) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C10 B1 1.5927(14) . ? B1 H1 1.116(12) . ? B1 H2 1.075(13) . ? 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 C3 O1 N1 109.66(6) . . ? O1 N1 C1 107.79(7) . . ? O1 N1 B1 109.73(7) . . ? C1 N1 B1 113.91(7) . . ? O1 N1 H1N 107.8(8) . . ? C1 N1 H1N 108.1(8) . . ? B1 N1 H1N 109.4(8) . . ? N1 C1 C2 115.30(8) . . ? N1 C1 H1A 108.4 . . ? C2 C1 H1A 108.4 . . ? N1 C1 H1B 108.4 . . ? C2 C1 H1B 108.4 . . ? H1A C1 H1B 107.5 . . ? C1 C2 Cl1 112.39(7) . . ? C1 C2 H2A 109.1 . . ? Cl1 C2 H2A 109.1 . . ? C1 C2 H2B 109.1 . . ? Cl1 C2 H2B 109.1 . . ? H2A C2 H2B 107.9 . . ? O1 C3 C4 106.37(7) . . ? O1 C3 H3A 110.5 . . ? C4 C3 H3A 110.5 . . ? O1 C3 H3B 110.5 . . ? C4 C3 H3B 110.5 . . ? H3A C3 H3B 108.6 . . ? C9 C4 C5 119.47(9) . . ? C9 C4 C3 120.38(9) . . ? C5 C4 C3 120.15(9) . . ? C6 C5 C4 120.40(9) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C7 C6 C5 119.89(9) . . ? C7 C6 H6 120.1 . . ? C5 C6 H6 120.1 . . ? C8 C7 C6 119.88(9) . . ? C8 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? C7 C8 C9 120.37(9) . . ? C7 C8 H8 119.8 . . ? C9 C8 H8 119.8 . . ? C8 C9 C4 119.93(9) . . ? C8 C9 H9 120.0 . . ? C4 C9 H9 120.0 . . ? N2 C10 B1 179.37(11) . . ? N1 B1 C10 106.77(7) . . ? N1 B1 H1 106.2(7) . . ? C10 B1 H1 109.8(6) . . ? N1 B1 H2 108.7(7) . . ? C10 B1 H2 110.8(7) . . ? H1 B1 H2 114.1(10) . . ? 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 C3 O1 N1 C1 -139.27(8) . . . . ? C3 O1 N1 B1 96.17(9) . . . . ? O1 N1 C1 C2 49.44(10) . . . . ? B1 N1 C1 C2 171.45(8) . . . . ? N1 C1 C2 Cl1 60.40(10) . . . . ? N1 O1 C3 C4 -178.62(7) . . . . ? O1 C3 C4 C9 127.15(9) . . . . ? O1 C3 C4 C5 -53.44(12) . . . . ? C9 C4 C5 C6 -2.50(14) . . . . ? C3 C4 C5 C6 178.08(9) . . . . ? C4 C5 C6 C7 2.06(14) . . . . ? C5 C6 C7 C8 0.37(14) . . . . ? C6 C7 C8 C9 -2.34(15) . . . . ? C7 C8 C9 C4 1.89(15) . . . . ? C5 C4 C9 C8 0.53(14) . . . . ? C3 C4 C9 C8 179.94(9) . . . . ? O1 N1 B1 C10 64.41(9) . . . . ? C1 N1 B1 C10 -56.52(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 H1N N2 0.897(13) 2.051(13) 2.9337(11) 167.7(11) 2_655 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 30.53 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.397 _refine_diff_density_min -0.274 _refine_diff_density_rms 0.046 ###END #=============================================================================80 # Data for compound 8 (local labelling ea10707a) #=============================================================================80 data_8 _database_code_depnum_ccdc_archive 'CCDC 816971' #TrackingRef '- Global CIF with all 3 structures in one.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H14 B Br N2 O' _chemical_formula_sum 'C10 H14 B Br N2 O' _chemical_formula_weight 268.95 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' B B 0.0013 0.0007 '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 Monoclinic _symmetry_space_group_name_H-M P2(1)/c _symmetry_space_group_name_Hall '-P 2ybc' 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 9.6308(3) _cell_length_b 12.4411(4) _cell_length_c 9.9555(4) _cell_angle_alpha 90.00 _cell_angle_beta 92.716(2) _cell_angle_gamma 90.00 _cell_volume 1191.51(7) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4146 _cell_measurement_theta_min 2.62 _cell_measurement_theta_max 27.51 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.499 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 3.425 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2091 _exptl_absorpt_correction_T_max 0.3464 _exptl_absorpt_process_details ; SADABS, Bruker (2006). APEX 2. Version 2.1. Bruker Analytical X-ray Solutions, Madison, Wisconsin, USA. ; _diffrn_ambient_temperature 173(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 ; Bruker-Nonius X8kappa APEX II CCD area detector' ; _diffrn_measurement_method 'phi and omega scans with narrow frames' _diffrn_detector_area_resol_mean 8.26 _diffrn_standards_decay_% 0 _diffrn_reflns_number 15111 _diffrn_reflns_av_R_equivalents 0.0399 _diffrn_reflns_av_sigmaI/netI 0.0378 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.31 _diffrn_reflns_theta_max 28.82 _reflns_number_total 3094 _reflns_number_gt 2282 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker (2006). APEX 2. Version 2.1.' _computing_cell_refinement 'Bruker (2006). APEX 2. Version 2.1.' _computing_data_reduction 'Bruker (2006). APEX 2. Version 2.1.' _computing_structure_solution 'Bruker (2006). APEX 2. Version 2.1.' _computing_structure_refinement 'XL, SHELXTL v. 6.14 (Bruker, 2003)' _computing_molecular_graphics 'XP, SHELXTL v. 6.14 (Bruker, 2003)' _computing_publication_material 'XCIF, SHELXTL v. 6.14 (Bruker, 2003)' _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^)+(0.0311P)^2^+0.9782P] 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 3094 _refine_ls_number_parameters 139 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0632 _refine_ls_R_factor_gt 0.0369 _refine_ls_wR_factor_ref 0.0829 _refine_ls_wR_factor_gt 0.0736 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _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 0.20321(3) 1.03411(2) 0.01155(3) 0.04245(11) Uani 1 1 d . . . O1 O 0.28576(15) 0.85127(11) 0.29621(16) 0.0220(3) Uani 1 1 d . . . N1 N 0.40386(18) 0.88286(15) 0.22100(19) 0.0208(4) Uani 1 1 d D . . H1N H 0.409(3) 0.9564(13) 0.226(3) 0.025 Uiso 1 1 d D . . N2 N 0.5268(2) 0.61447(17) 0.2629(2) 0.0381(5) Uani 1 1 d . . . C1 C 0.3762(2) 0.85056(19) 0.0788(2) 0.0261(5) Uani 1 1 d . . . H1A H 0.3878 0.7717 0.0723 0.031 Uiso 1 1 calc R . . H1B H 0.4475 0.8842 0.0239 0.031 Uiso 1 1 calc R . . C2 C 0.2346(3) 0.8797(2) 0.0182(3) 0.0314(5) Uani 1 1 d . . . H2A H 0.1625 0.8459 0.0718 0.038 Uiso 1 1 calc R . . H2B H 0.2249 0.8503 -0.0742 0.038 Uiso 1 1 calc R . . C3 C 0.2525(3) 0.93485(19) 0.3908(3) 0.0322(6) Uani 1 1 d . . . H3A H 0.2271 1.0022 0.3426 0.039 Uiso 1 1 calc R . . H3B H 0.3331 0.9493 0.4536 0.039 Uiso 1 1 calc R . . C4 C 0.1323(2) 0.89397(17) 0.4655(2) 0.0240(5) Uani 1 1 d . . . C5 C 0.0108(2) 0.86086(18) 0.3972(3) 0.0276(5) Uani 1 1 d . . . H5 H 0.0027 0.8658 0.3019 0.033 Uiso 1 1 calc R . . C6 C -0.0987(2) 0.82063(19) 0.4672(3) 0.0313(6) Uani 1 1 d . . . H6 H -0.1807 0.7965 0.4197 0.038 Uiso 1 1 calc R . . C7 C -0.0888(2) 0.81556(19) 0.6060(3) 0.0313(6) Uani 1 1 d . . . H7 H -0.1634 0.7872 0.6541 0.038 Uiso 1 1 calc R . . C8 C 0.0298(3) 0.85184(19) 0.6741(3) 0.0300(5) Uani 1 1 d . . . H8 H 0.0354 0.8510 0.7696 0.036 Uiso 1 1 calc R . . C9 C 0.1409(2) 0.88953(19) 0.6048(2) 0.0272(5) Uani 1 1 d . . . H9 H 0.2233 0.9124 0.6527 0.033 Uiso 1 1 calc R . . C10 C 0.5314(2) 0.70585(19) 0.2728(2) 0.0271(5) Uani 1 1 d . . . B1 B 0.5419(3) 0.8333(2) 0.2875(3) 0.0268(6) Uani 1 1 d . . . H1C H 0.5517 0.8536 0.3837 0.032 Uiso 1 1 calc R . . H1D H 0.6238 0.8605 0.2416 0.032 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 Br1 0.04057(15) 0.02966(15) 0.0561(2) 0.01247(13) -0.00869(12) -0.00010(11) O1 0.0238(7) 0.0163(7) 0.0267(9) -0.0037(6) 0.0096(6) -0.0033(6) N1 0.0230(8) 0.0161(9) 0.0239(10) 0.0006(7) 0.0068(7) -0.0028(7) N2 0.0467(13) 0.0280(11) 0.0401(14) 0.0050(10) 0.0057(11) 0.0142(10) C1 0.0320(11) 0.0243(11) 0.0223(12) -0.0008(9) 0.0033(10) 0.0021(9) C2 0.0396(13) 0.0270(12) 0.0272(14) 0.0000(10) -0.0039(11) -0.0043(10) C3 0.0411(13) 0.0192(11) 0.0378(15) -0.0091(10) 0.0179(12) -0.0020(10) C4 0.0272(10) 0.0138(10) 0.0318(13) -0.0034(9) 0.0085(10) 0.0026(9) C5 0.0347(12) 0.0226(11) 0.0257(13) -0.0028(9) 0.0029(10) 0.0030(9) C6 0.0251(11) 0.0267(12) 0.0419(16) -0.0037(11) -0.0013(10) 0.0024(9) C7 0.0278(11) 0.0247(12) 0.0426(16) 0.0040(11) 0.0129(11) 0.0030(9) C8 0.0371(12) 0.0287(12) 0.0244(13) 0.0050(10) 0.0051(10) 0.0034(10) C9 0.0264(10) 0.0244(12) 0.0306(14) -0.0007(10) -0.0005(10) 0.0032(9) C10 0.0275(11) 0.0318(13) 0.0226(13) 0.0072(10) 0.0073(9) 0.0099(10) B1 0.0238(11) 0.0282(13) 0.0286(15) 0.0001(11) 0.0042(10) 0.0004(10) _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 C2 1.945(3) . ? O1 N1 1.446(2) . ? O1 C3 1.449(3) . ? N1 C1 1.484(3) . ? N1 B1 1.582(3) . ? N1 H1N 0.917(16) . ? N2 C10 1.142(3) . ? C1 C2 1.509(3) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.495(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.388(3) . ? C4 C9 1.386(3) . ? C5 C6 1.385(3) . ? C5 H5 0.9500 . ? C6 C7 1.382(4) . ? C6 H6 0.9500 . ? C7 C8 1.377(4) . ? C7 H7 0.9500 . ? C8 C9 1.382(3) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C10 B1 1.595(4) . ? B1 H1C 0.9900 . ? B1 H1D 0.9900 . ? 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 N1 O1 C3 110.20(15) . . ? O1 N1 C1 108.10(16) . . ? O1 N1 B1 110.07(16) . . ? C1 N1 B1 113.77(17) . . ? O1 N1 H1N 106.8(16) . . ? C1 N1 H1N 109.0(16) . . ? B1 N1 H1N 108.9(16) . . ? N1 C1 C2 115.74(19) . . ? N1 C1 H1A 108.3 . . ? C2 C1 H1A 108.3 . . ? N1 C1 H1B 108.3 . . ? C2 C1 H1B 108.3 . . ? H1A C1 H1B 107.4 . . ? C1 C2 Br1 112.78(16) . . ? C1 C2 H2A 109.0 . . ? Br1 C2 H2A 109.0 . . ? C1 C2 H2B 109.0 . . ? Br1 C2 H2B 109.0 . . ? H2A C2 H2B 107.8 . . ? O1 C3 C4 106.25(18) . . ? O1 C3 H3A 110.5 . . ? C4 C3 H3A 110.5 . . ? O1 C3 H3B 110.5 . . ? C4 C3 H3B 110.5 . . ? H3A C3 H3B 108.7 . . ? C5 C4 C9 119.2(2) . . ? C5 C4 C3 120.8(2) . . ? C9 C4 C3 120.0(2) . . ? C6 C5 C4 120.4(2) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C7 C6 C5 120.1(2) . . ? C7 C6 H6 120.0 . . ? C5 C6 H6 120.0 . . ? C8 C7 C6 119.6(2) . . ? C8 C7 H7 120.2 . . ? C6 C7 H7 120.2 . . ? C7 C8 C9 120.6(2) . . ? C7 C8 H8 119.7 . . ? C9 C8 H8 119.7 . . ? C8 C9 C4 120.1(2) . . ? C8 C9 H9 119.9 . . ? C4 C9 H9 119.9 . . ? N2 C10 B1 178.6(3) . . ? N1 B1 C10 107.53(19) . . ? N1 B1 H1C 110.2 . . ? C10 B1 H1C 110.2 . . ? N1 B1 H1D 110.2 . . ? C10 B1 H1D 110.2 . . ? H1C B1 H1D 108.5 . . ? 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 C3 O1 N1 C1 -138.88(19) . . . . ? C3 O1 N1 B1 96.3(2) . . . . ? O1 N1 C1 C2 47.3(2) . . . . ? B1 N1 C1 C2 169.86(19) . . . . ? N1 C1 C2 Br1 62.6(2) . . . . ? N1 O1 C3 C4 -178.64(18) . . . . ? O1 C3 C4 C5 -55.5(3) . . . . ? O1 C3 C4 C9 125.0(2) . . . . ? C9 C4 C5 C6 -2.1(3) . . . . ? C3 C4 C5 C6 178.4(2) . . . . ? C4 C5 C6 C7 1.5(3) . . . . ? C5 C6 C7 C8 0.7(3) . . . . ? C6 C7 C8 C9 -2.4(4) . . . . ? C7 C8 C9 C4 1.8(4) . . . . ? C5 C4 C9 C8 0.4(3) . . . . ? C3 C4 C9 C8 179.9(2) . . . . ? O1 N1 B1 C10 65.3(2) . . . . ? C1 N1 B1 C10 -56.2(2) . . . . ? 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 H1N N2 0.917(16) 2.063(17) 2.960(3) 166(2) 2_655 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 28.82 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.626 _refine_diff_density_min -0.615 _refine_diff_density_rms 0.075 ###END