data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 #TrackingRef 'anti.cif' _audit_creation_method 'APEX2 v2011.8-0' _publ_contact_author_name ' Ji-Cheng Zhao' _publ_contact_author_address ; ; _publ_contact_author_email zhao.199@osu.edu _publ_contact_author_fax ? _publ_contact_author_phone ? _publ_section_title ; ; _publ_section_abstract ; ; _publ_section_references ; ; _publ_section_comment ; ; _publ_requested_category FO _publ_author_name 'Ji-Cheng Zhao' data_Zhao1785 _database_code_depnum_ccdc_archive 'CCDC 882868' #TrackingRef '- gauchechunk.cif' _audit_creation_date 2012-03-27T15:06:55-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_name_common zhao1785 _chemical_formula_moiety 'C12 H24 O6, B2 H10 N2' _chemical_formula_sum 'C12 H34 B2 N2 O6' _chemical_formula_weight 324.03 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration unk #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P212121 _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_Int_Tables_number 19 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 8.8717(1) _cell_length_b 11.6178(1) _cell_length_c 18.2118(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1877.08(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1932 _cell_measurement_theta_min 2.263 _cell_measurement_theta_max 25.028 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description chunk _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.27 _exptl_crystal_density_diffrn 1.147 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 712 _exptl_special_details ;All work was done at 150 K using an Oxford Cryosystems Cryostream Cooler. ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.870 _exptl_absorpt_correction_T_max 0.977 _exptl_absorpt_process_details 'HKL Scalepack (Otwinowski & Minor, 1997)' #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 -0.574771E-1 _diffrn_orient_matrix_ub_12 -0.152292E-1 _diffrn_orient_matrix_ub_13 0.462244E-1 _diffrn_orient_matrix_ub_21 -0.878175E-1 _diffrn_orient_matrix_ub_22 -0.275352E-1 _diffrn_orient_matrix_ub_23 -0.296045E-1 _diffrn_orient_matrix_ub_31 0.411074E-1 _diffrn_orient_matrix_ub_32 -0.801171E-1 _diffrn_orient_matrix_ub_33 0.13881E-2 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'CCD rotation images, 1 degree frames' _diffrn_reflns_av_unetI/netI ? _diffrn_reflns_av_R_equivalents 0.031 _diffrn_reflns_number 51930 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.55 _diffrn_reflns_theta_max 25.01 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 3319 _reflns_number_gt 3004 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0530P)^2^+0.1597P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.0092(16) _refine_ls_number_reflns 3319 _refine_ls_number_parameters 240 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.037 _refine_ls_R_factor_gt 0.0314 _refine_ls_wR_factor_ref 0.0832 _refine_ls_wR_factor_gt 0.0799 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.011 _refine_ls_shift/su_mean 0.001 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1.2(8) _refine_diff_density_max 0.131 _refine_diff_density_min -0.138 _refine_diff_density_rms 0.029 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.14294(14) 0.47312(9) 0.94432(7) 0.0294(3) Uani 1 1 d . . . HN1 H 0.055(2) 0.4922(15) 0.9645(9) 0.046(5) Uiso 1 1 d . . . HN2 H 0.1376(19) 0.4942(14) 0.8993(10) 0.041(4) Uiso 1 1 d . . . HN3 H 0.214(2) 0.5253(16) 0.9666(10) 0.049(5) Uiso 1 1 d . . . N2 N 0.33357(14) 0.31169(11) 0.92301(7) 0.0342(3) Uani 1 1 d . . . HN4 H 0.354(2) 0.2384(18) 0.9333(10) 0.054(5) Uiso 1 1 d . . . HN5 H 0.411(2) 0.3517(18) 0.9511(11) 0.062(5) Uiso 1 1 d . . . B1 B 0.17594(19) 0.34018(13) 0.95673(10) 0.0346(4) Uani 1 1 d . . . HB1 H 0.0900(19) 0.2910(15) 0.9280(9) 0.045(4) Uiso 1 1 d . . . HB2 H 0.1791(19) 0.3229(14) 1.0176(9) 0.045(4) Uiso 1 1 d . . . B2 B 0.3580(2) 0.33453(15) 0.83718(10) 0.0410(4) Uani 1 1 d . . . HB3 H 0.362(2) 0.4280(17) 0.8285(10) 0.061(5) Uiso 1 1 d . . . HB4 H 0.270(2) 0.298(2) 0.8088(12) 0.076(6) Uiso 1 1 d . . . HB5 H 0.463(3) 0.2961(19) 0.8238(11) 0.076(6) Uiso 1 1 d . . . O1 O -0.19423(12) 0.52378(9) 0.89617(6) 0.0453(3) Uani 1 1 d . . . O2 O 0.04617(13) 0.59696(9) 0.80376(6) 0.0444(3) Uani 1 1 d . . . O3 O 0.29491(11) 0.70721(9) 0.86968(6) 0.0389(3) Uani 1 1 d . . . O4 O 0.38410(12) 0.62438(9) 1.01243(6) 0.0415(3) Uani 1 1 d . . . O5 O 0.13720(12) 0.56110(8) 1.10510(5) 0.0399(3) Uani 1 1 d . . . O6 O -0.12698(11) 0.45930(8) 1.04530(6) 0.0388(2) Uani 1 1 d . . . C1 C -0.1779(2) 0.49044(16) 0.82162(10) 0.0569(5) Uani 1 1 d . . . H1A H -0.2781 0.4735 0.8002 0.068 Uiso 1 1 calc R . . H1B H -0.1156 0.42 0.8184 0.068 Uiso 1 1 calc R . . C2 C -0.1049(2) 0.58523(16) 0.78010(9) 0.0559(5) Uani 1 1 d . . . H2A H -0.1074 0.568 0.7269 0.067 Uiso 1 1 calc R . . H2B H -0.1601 0.6581 0.7885 0.067 Uiso 1 1 calc R . . C3 C 0.1207(2) 0.69114(13) 0.77071(8) 0.0460(4) Uani 1 1 d . . . H3A H 0.0737 0.7642 0.7868 0.055 Uiso 1 1 calc R . . H3B H 0.1121 0.6859 0.7166 0.055 Uiso 1 1 calc R . . C4 C 0.2811(2) 0.68908(14) 0.79244(8) 0.0483(4) Uani 1 1 d . . . H4A H 0.3259 0.6139 0.7792 0.058 Uiso 1 1 calc R . . H4B H 0.3366 0.75 0.7657 0.058 Uiso 1 1 calc R . . C5 C 0.44652(18) 0.69233(14) 0.89279(10) 0.0479(4) Uani 1 1 d . . . H5A H 0.5131 0.7459 0.8657 0.058 Uiso 1 1 calc R . . H5B H 0.4799 0.6127 0.8824 0.058 Uiso 1 1 calc R . . C6 C 0.45564(18) 0.71559(13) 0.97253(10) 0.0496(4) Uani 1 1 d . . . H6A H 0.5626 0.7217 0.9876 0.06 Uiso 1 1 calc R . . H6B H 0.4053 0.7896 0.9838 0.06 Uiso 1 1 calc R . . C7 C 0.3787(2) 0.64701(15) 1.08859(9) 0.0529(5) Uani 1 1 d . . . H7A H 0.3302 0.7225 1.0973 0.063 Uiso 1 1 calc R . . H7B H 0.4824 0.6502 1.1086 0.063 Uiso 1 1 calc R . . C8 C 0.2913(2) 0.55444(16) 1.12682(9) 0.0524(5) Uani 1 1 d . . . H8A H 0.3328 0.478 1.1138 0.063 Uiso 1 1 calc R . . H8B H 0.2995 0.5643 1.1807 0.063 Uiso 1 1 calc R . . C9 C 0.0445(2) 0.48353(14) 1.14487(8) 0.0484(4) Uani 1 1 d . . . H9A H 0.0509 0.5008 1.198 0.058 Uiso 1 1 calc R . . H9B H 0.0801 0.4037 1.1371 0.058 Uiso 1 1 calc R . . C10 C -0.1152(2) 0.49427(13) 1.11974(9) 0.0489(4) Uani 1 1 d . . . H10A H -0.1811 0.4455 1.1507 0.059 Uiso 1 1 calc R . . H10B H -0.1489 0.5751 1.1247 0.059 Uiso 1 1 calc R . . C11 C -0.27452(18) 0.47239(15) 1.01570(12) 0.0561(5) Uani 1 1 d . . . H11A H -0.3075 0.5534 1.0206 0.067 Uiso 1 1 calc R . . H11B H -0.3463 0.4232 1.0431 0.067 Uiso 1 1 calc R . . C12 C -0.27347(19) 0.43913(15) 0.93765(12) 0.0578(5) Uani 1 1 d . . . H12A H -0.2239 0.3633 0.9319 0.069 Uiso 1 1 calc R . . H12B H -0.3782 0.4326 0.9194 0.069 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 0.0318(7) 0.0273(6) 0.0291(6) 0.0007(5) 0.0011(5) 0.0003(5) N2 0.0326(7) 0.0326(7) 0.0372(7) -0.0012(5) 0.0019(5) 0.0010(5) B1 0.0314(9) 0.0264(7) 0.0461(10) 0.0011(7) 0.0080(7) 0.0018(6) B2 0.0520(11) 0.0341(9) 0.0370(9) -0.0034(7) 0.0082(9) 0.0011(8) O1 0.0400(6) 0.0342(5) 0.0618(7) 0.0076(5) -0.0156(5) -0.0067(5) O2 0.0609(7) 0.0371(6) 0.0354(5) 0.0061(4) -0.0125(5) -0.0011(5) O3 0.0373(6) 0.0339(5) 0.0455(6) -0.0023(4) 0.0116(5) -0.0022(4) O4 0.0367(6) 0.0348(5) 0.0529(6) -0.0080(4) -0.0099(5) -0.0029(5) O5 0.0522(6) 0.0375(5) 0.0298(5) 0.0040(4) -0.0048(5) 0.0102(5) O6 0.0318(5) 0.0352(5) 0.0493(6) 0.0071(4) 0.0117(5) 0.0047(4) C1 0.0567(11) 0.0507(10) 0.0634(11) -0.0103(9) -0.0296(9) -0.0063(8) C2 0.0684(12) 0.0613(11) 0.0379(9) -0.0025(8) -0.0265(8) 0.0039(9) C3 0.0804(13) 0.0320(7) 0.0256(7) 0.0048(6) 0.0083(8) 0.0063(8) C4 0.0722(12) 0.0343(8) 0.0384(9) 0.0056(7) 0.0279(8) 0.0025(8) C5 0.0345(8) 0.0310(8) 0.0783(12) 0.0026(8) 0.0142(8) -0.0026(6) C6 0.0301(8) 0.0288(8) 0.0900(13) -0.0007(8) -0.0109(8) -0.0039(6) C7 0.0473(10) 0.0556(10) 0.0559(10) -0.0202(8) -0.0233(9) 0.0085(8) C8 0.0596(10) 0.0628(11) 0.0348(8) -0.0077(8) -0.0205(8) 0.0245(9) C9 0.0793(12) 0.0393(8) 0.0266(7) 0.0056(6) 0.0084(7) 0.0149(8) C10 0.0627(11) 0.0354(8) 0.0485(9) 0.0084(7) 0.0327(9) 0.0082(8) C11 0.0272(8) 0.0438(9) 0.0973(15) 0.0285(10) 0.0124(8) 0.0017(7) C12 0.0371(9) 0.0446(9) 0.0918(15) 0.0241(10) -0.0197(9) -0.0138(7) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 B1 1.5881(18) . ? N1 HN1 0.89(2) . ? N1 HN2 0.858(18) . ? N1 HN3 0.97(2) . ? N2 B1 1.563(2) . ? N2 B2 1.600(2) . ? N2 HN4 0.89(2) . ? N2 HN5 0.97(2) . ? B1 HB1 1.086(17) . ? B1 HB2 1.127(16) . ? B2 HB3 1.098(19) . ? B2 HB4 1.03(2) . ? B2 HB5 1.06(2) . ? O1 C1 1.419(2) . ? O1 C12 1.425(2) . ? O2 C3 1.4132(19) . ? O2 C2 1.414(2) . ? O3 C5 1.420(2) . ? O3 C4 1.4277(19) . ? O4 C7 1.4125(19) . ? O4 C6 1.433(2) . ? O5 C9 1.419(2) . ? O5 C8 1.425(2) . ? O6 C10 1.419(2) . ? O6 C11 1.424(2) . ? C1 C2 1.485(3) . ? C1 H1A 0.99 . ? C1 H1B 0.99 . ? C2 H2A 0.99 . ? C2 H2B 0.99 . ? C3 C4 1.477(3) . ? C3 H3A 0.99 . ? C3 H3B 0.99 . ? C4 H4A 0.99 . ? C4 H4B 0.99 . ? C5 C6 1.479(2) . ? C5 H5A 0.99 . ? C5 H5B 0.99 . ? C6 H6A 0.99 . ? C6 H6B 0.99 . ? C7 C8 1.498(3) . ? C7 H7A 0.99 . ? C7 H7B 0.99 . ? C8 H8A 0.99 . ? C8 H8B 0.99 . ? C9 C10 1.494(3) . ? C9 H9A 0.99 . ? C9 H9B 0.99 . ? C10 H10A 0.99 . ? C10 H10B 0.99 . ? C11 C12 1.473(3) . ? C11 H11A 0.99 . ? C11 H11B 0.99 . ? C12 H12A 0.99 . ? C12 H12B 0.99 . ? 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 B1 N1 HN1 110.2(11) . . ? B1 N1 HN2 115.1(11) . . ? HN1 N1 HN2 105.9(15) . . ? B1 N1 HN3 115.5(10) . . ? HN1 N1 HN3 104.2(15) . . ? HN2 N1 HN3 105.1(15) . . ? B1 N2 B2 118.03(13) . . ? B1 N2 HN4 107.6(12) . . ? B2 N2 HN4 109.7(12) . . ? B1 N2 HN5 108.7(11) . . ? B2 N2 HN5 109.9(12) . . ? HN4 N2 HN5 101.7(17) . . ? N2 B1 N1 108.36(12) . . ? N2 B1 HB1 109.1(9) . . ? N1 B1 HB1 108.3(9) . . ? N2 B1 HB2 109.0(9) . . ? N1 B1 HB2 108.6(8) . . ? HB1 B1 HB2 113.4(12) . . ? N2 B2 HB3 108.0(9) . . ? N2 B2 HB4 108.5(13) . . ? HB3 B2 HB4 111.3(17) . . ? N2 B2 HB5 105.8(11) . . ? HB3 B2 HB5 110.7(16) . . ? HB4 B2 HB5 112.1(16) . . ? C1 O1 C12 111.65(14) . . ? C3 O2 C2 112.85(13) . . ? C5 O3 C4 110.83(12) . . ? C7 O4 C6 112.04(12) . . ? C9 O5 C8 112.33(12) . . ? C10 O6 C11 113.49(13) . . ? O1 C1 C2 109.23(13) . . ? O1 C1 H1A 109.8 . . ? C2 C1 H1A 109.8 . . ? O1 C1 H1B 109.8 . . ? C2 C1 H1B 109.8 . . ? H1A C1 H1B 108.3 . . ? O2 C2 C1 109.27(13) . . ? O2 C2 H2A 109.8 . . ? C1 C2 H2A 109.8 . . ? O2 C2 H2B 109.8 . . ? C1 C2 H2B 109.8 . . ? H2A C2 H2B 108.3 . . ? O2 C3 C4 108.91(13) . . ? O2 C3 H3A 109.9 . . ? C4 C3 H3A 109.9 . . ? O2 C3 H3B 109.9 . . ? C4 C3 H3B 109.9 . . ? H3A C3 H3B 108.3 . . ? O3 C4 C3 110.16(12) . . ? O3 C4 H4A 109.6 . . ? C3 C4 H4A 109.6 . . ? O3 C4 H4B 109.6 . . ? C3 C4 H4B 109.6 . . ? H4A C4 H4B 108.1 . . ? O3 C5 C6 108.69(13) . . ? O3 C5 H5A 110 . . ? C6 C5 H5A 110 . . ? O3 C5 H5B 110 . . ? C6 C5 H5B 110 . . ? H5A C5 H5B 108.3 . . ? O4 C6 C5 109.78(12) . . ? O4 C6 H6A 109.7 . . ? C5 C6 H6A 109.7 . . ? O4 C6 H6B 109.7 . . ? C5 C6 H6B 109.7 . . ? H6A C6 H6B 108.2 . . ? O4 C7 C8 109.89(13) . . ? O4 C7 H7A 109.7 . . ? C8 C7 H7A 109.7 . . ? O4 C7 H7B 109.7 . . ? C8 C7 H7B 109.7 . . ? H7A C7 H7B 108.2 . . ? O5 C8 C7 109.20(13) . . ? O5 C8 H8A 109.8 . . ? C7 C8 H8A 109.8 . . ? O5 C8 H8B 109.8 . . ? C7 C8 H8B 109.8 . . ? H8A C8 H8B 108.3 . . ? O5 C9 C10 109.90(12) . . ? O5 C9 H9A 109.7 . . ? C10 C9 H9A 109.7 . . ? O5 C9 H9B 109.7 . . ? C10 C9 H9B 109.7 . . ? H9A C9 H9B 108.2 . . ? O6 C10 C9 109.77(12) . . ? O6 C10 H10A 109.7 . . ? C9 C10 H10A 109.7 . . ? O6 C10 H10B 109.7 . . ? C9 C10 H10B 109.7 . . ? H10A C10 H10B 108.2 . . ? O6 C11 C12 109.37(14) . . ? O6 C11 H11A 109.8 . . ? C12 C11 H11A 109.8 . . ? O6 C11 H11B 109.8 . . ? C12 C11 H11B 109.8 . . ? H11A C11 H11B 108.2 . . ? O1 C12 C11 109.48(14) . . ? O1 C12 H12A 109.8 . . ? C11 C12 H12A 109.8 . . ? O1 C12 H12B 109.8 . . ? C11 C12 H12B 109.8 . . ? H12A C12 H12B 108.2 . . ? 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 N2 HN4 O6 0.89(2) 2.34(2) 3.2198(16) 171.9(17) 4_557 N1 HN1 O6 0.89(2) 2.22(2) 3.0236(16) 150.2(15) . N1 HN1 O1 0.89(2) 2.561(18) 3.1723(17) 126.3(13) . N1 HN2 O2 0.858(18) 2.260(19) 3.0594(16) 155.1(15) . N1 HN3 O4 0.97(2) 2.07(2) 3.0338(15) 174.0(15) . # END of CIF # Attachment '- gaucheneedle.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2012-02-29 at 17:38:23 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.4 # Request file : c:\wingx\files\archive.reqdat # CIF files read : shelxl dreduc import struct #------------------ SECTION 1. GLOBAL INFORMATION ---------------------------# data_Zhao1786 _database_code_depnum_ccdc_archive 'CCDC 882869' #TrackingRef '- gaucheneedle.cif' _audit_creation_date 2012-02-29T17:38:23-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_name_common zhao1786 _chemical_formula_moiety 'C12 H24 O6, B2 H10 N2' _chemical_formula_sum 'C12 H34 B2 N2 O6' _chemical_formula_weight 324.03 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration unk #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P212121 _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_Int_Tables_number 19 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 8.3112(1) _cell_length_b 13.0955(2) _cell_length_c 16.7666(3) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1824.87(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3458 _cell_measurement_theta_min 2.037 _cell_measurement_theta_max 25.028 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_diffrn 1.179 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 712 _exptl_special_details ;All work was done at 150 K using an Oxford Cryosystems Cryostream Cooler. ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.904 _exptl_absorpt_correction_T_max 0.993 _exptl_absorpt_process_details 'HKL Scalepack (Otwinowski & Minor, 1997)' #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 -0.700208E-1 _diffrn_orient_matrix_ub_12 0.479248E-1 _diffrn_orient_matrix_ub_13 0.13639E-2 _diffrn_orient_matrix_ub_21 -0.210899E-1 _diffrn_orient_matrix_ub_22 -0.812792E-1 _diffrn_orient_matrix_ub_23 0.407699E-1 _diffrn_orient_matrix_ub_31 0.219881E-1 _diffrn_orient_matrix_ub_32 0.746572E-1 _diffrn_orient_matrix_ub_33 0.435106E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'CCD rotation images, 1 degree frames' _diffrn_reflns_av_R_equivalents 0.066 _diffrn_reflns_av_unetI/netI ? _diffrn_reflns_number 28432 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.74 _diffrn_reflns_theta_max 25.04 _diffrn_reflns_theta_full 25.04 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 3225 _reflns_number_gt 2423 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0353P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 3225 _refine_ls_number_parameters 239 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0631 _refine_ls_R_factor_gt 0.0356 _refine_ls_wR_factor_ref 0.072 _refine_ls_wR_factor_gt 0.0656 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -1.1(8) _refine_diff_density_max 0.137 _refine_diff_density_min -0.153 _refine_diff_density_rms 0.035 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 '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' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O4 O 1.03450(13) 0.51950(9) 0.48309(7) 0.0275(3) Uani 1 1 d . . . O1 O 0.63247(13) 0.25681(9) 0.65710(7) 0.0275(3) Uani 1 1 d . . . O2 O 0.52908(13) 0.34550(9) 0.50583(6) 0.0259(3) Uani 1 1 d . . . O5 O 1.14126(14) 0.43488(9) 0.63254(7) 0.0267(3) Uani 1 1 d . . . O6 O 0.89921(13) 0.34809(9) 0.73332(7) 0.0281(3) Uani 1 1 d . . . O3 O 0.76524(13) 0.43317(9) 0.40983(7) 0.0273(3) Uani 1 1 d . . . C6 C 1.0193(2) 0.51580(15) 0.39867(10) 0.0301(5) Uani 1 1 d . . . H6A H 1.068 0.452 0.3781 0.036 Uiso 1 1 calc R . . H6B H 1.0767 0.5743 0.3745 0.036 Uiso 1 1 calc R . . C3 C 0.5272(2) 0.33433(14) 0.42153(10) 0.0276(4) Uani 1 1 d . . . H3A H 0.4151 0.3264 0.4026 0.033 Uiso 1 1 calc R . . H3B H 0.5883 0.2725 0.4061 0.033 Uiso 1 1 calc R . . C12 C 0.6466(2) 0.26284(14) 0.74161(10) 0.0288(5) Uani 1 1 d . . . H12A H 0.5892 0.2048 0.7666 0.035 Uiso 1 1 calc R . . H12B H 0.5971 0.327 0.7609 0.035 Uiso 1 1 calc R . . C7 C 1.19892(19) 0.51565(15) 0.50802(11) 0.0318(5) Uani 1 1 d . . . H7A H 1.2597 0.5722 0.483 0.038 Uiso 1 1 calc R . . H7B H 1.2479 0.4504 0.4908 0.038 Uiso 1 1 calc R . . C8 C 1.2077(2) 0.52446(15) 0.59615(11) 0.0314(5) Uani 1 1 d . . . H8A H 1.3212 0.5328 0.6128 0.038 Uiso 1 1 calc R . . H8B H 1.147 0.5854 0.6139 0.038 Uiso 1 1 calc R . . C9 C 1.1421(2) 0.44279(14) 0.71712(10) 0.0290(5) Uani 1 1 d . . . H9A H 1.0823 0.5046 0.7336 0.035 Uiso 1 1 calc R . . H9B H 1.2543 0.4493 0.7364 0.035 Uiso 1 1 calc R . . C11 C 0.8208(2) 0.26002(13) 0.76455(11) 0.0298(5) Uani 1 1 d . . . H11A H 0.8311 0.2588 0.8234 0.036 Uiso 1 1 calc R . . H11B H 0.8717 0.1975 0.743 0.036 Uiso 1 1 calc R . . N1 N 0.7697(2) 0.47964(14) 0.59629(11) 0.0294(4) Uani 1 1 d . . . C5 C 0.8445(2) 0.51976(14) 0.37650(11) 0.0308(5) Uani 1 1 d . . . H5A H 0.7954 0.5833 0.3973 0.037 Uiso 1 1 calc R . . H5B H 0.8329 0.5193 0.3177 0.037 Uiso 1 1 calc R . . C4 C 0.6016(2) 0.42666(14) 0.38415(11) 0.0290(5) Uani 1 1 d . . . H4A H 0.5968 0.4212 0.3253 0.035 Uiso 1 1 calc R . . H4B H 0.5422 0.4888 0.4005 0.035 Uiso 1 1 calc R . . C10 C 1.06578(19) 0.35019(14) 0.75350(11) 0.0293(5) Uani 1 1 d . . . H10A H 1.1193 0.2878 0.7333 0.035 Uiso 1 1 calc R . . H10B H 1.0784 0.3521 0.8122 0.035 Uiso 1 1 calc R . . C2 C 0.4567(2) 0.26003(14) 0.54398(10) 0.0284(4) Uani 1 1 d . . . H2A H 0.5116 0.1965 0.5272 0.034 Uiso 1 1 calc R . . H2B H 0.3422 0.2551 0.5283 0.034 Uiso 1 1 calc R . . C1 C 0.4693(2) 0.27199(14) 0.63214(11) 0.0290(5) Uani 1 1 d . . . H1A H 0.4333 0.3412 0.6477 0.035 Uiso 1 1 calc R . . H1B H 0.3987 0.2216 0.6588 0.035 Uiso 1 1 calc R . . N2 N 0.7432(2) 0.67188(14) 0.57280(11) 0.0394(4) Uani 1 1 d . . . B1 B 0.7503(3) 0.58647(17) 0.63896(14) 0.0370(6) Uani 1 1 d . . . B2 B 0.5778(3) 0.6837(2) 0.52455(16) 0.0415(7) Uani 1 1 d . . . HB2 H 0.639(2) 0.5826(12) 0.6721(9) 0.020(4) Uiso 1 1 d . . . HB1 H 0.858(2) 0.5985(12) 0.6788(10) 0.026(4) Uiso 1 1 d . . . HN3 H 0.790(2) 0.4317(14) 0.6297(11) 0.025(6) Uiso 1 1 d . . . HN2 H 0.690(3) 0.4593(14) 0.5686(11) 0.039(6) Uiso 1 1 d . . . HN1 H 0.857(3) 0.4782(16) 0.5612(13) 0.056(7) Uiso 1 1 d . . . HB3 H 0.543(2) 0.6029(16) 0.5039(11) 0.052(6) Uiso 1 1 d . . . HB4 H 0.489(2) 0.7193(13) 0.5681(11) 0.042(5) Uiso 1 1 d . . . HN4 H 0.762(3) 0.7408(19) 0.5994(13) 0.072(7) Uiso 1 1 d . . . HB5 H 0.600(2) 0.7371(15) 0.4713(12) 0.056(6) Uiso 1 1 d . . . HN5 H 0.827(3) 0.6668(19) 0.5305(15) 0.081(8) 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 O4 0.0206(6) 0.0341(7) 0.0276(8) 0.0023(6) 0.0010(5) -0.0022(6) O1 0.0252(7) 0.0335(7) 0.0238(7) -0.0016(6) 0.0013(5) -0.0006(6) O2 0.0271(7) 0.0270(7) 0.0237(7) -0.0006(6) -0.0001(5) -0.0047(6) O5 0.0253(7) 0.0291(7) 0.0256(7) -0.0021(6) -0.0001(5) -0.0017(5) O6 0.0240(7) 0.0305(7) 0.0298(7) 0.0057(6) -0.0032(5) 0.0000(6) O3 0.0227(7) 0.0293(7) 0.0300(7) 0.0074(6) -0.0028(6) -0.0004(5) C6 0.0325(11) 0.0348(11) 0.0231(12) 0.0045(9) 0.0055(9) -0.0036(9) C3 0.0231(9) 0.0330(11) 0.0266(11) -0.0039(9) -0.0030(8) 0.0004(9) C12 0.0347(10) 0.0308(11) 0.0209(11) -0.0008(9) 0.0043(8) -0.0059(9) C7 0.0207(11) 0.0406(13) 0.0342(12) 0.0069(10) 0.0009(8) -0.0026(9) C8 0.0246(10) 0.0332(11) 0.0364(13) 0.0014(9) -0.0025(9) -0.0071(9) C9 0.0259(10) 0.0351(11) 0.0259(12) -0.0050(9) -0.0040(8) 0.0016(9) C11 0.0397(11) 0.0259(11) 0.0240(11) 0.0038(9) 0.0003(8) 0.0003(9) N1 0.0256(10) 0.0343(11) 0.0284(11) 0.0030(9) -0.0024(9) 0.0007(8) C5 0.0350(11) 0.0312(11) 0.0261(11) 0.0069(9) -0.0015(9) -0.0027(9) C4 0.0253(10) 0.0350(11) 0.0268(11) -0.0010(9) -0.0059(9) 0.0031(9) C10 0.0252(10) 0.0388(11) 0.0240(11) -0.0011(9) -0.0055(8) 0.0071(9) C2 0.0241(10) 0.0273(10) 0.0339(12) 0.0016(9) -0.0006(8) -0.0058(9) C1 0.0222(10) 0.0309(11) 0.0339(12) 0.0015(9) 0.0038(8) -0.0041(8) N2 0.0361(10) 0.0387(11) 0.0432(11) 0.0005(9) -0.0047(9) -0.0013(9) B1 0.0421(15) 0.0382(15) 0.0308(14) -0.0018(11) -0.0015(12) 0.0094(12) B2 0.0316(14) 0.0480(17) 0.0449(17) 0.0028(14) -0.0020(12) 0.0025(12) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O4 C6 1.422(2) . ? O4 C7 1.4299(19) . ? O1 C12 1.424(2) . ? O1 C1 1.433(2) . ? O2 C3 1.421(2) . ? O2 C2 1.423(2) . ? O5 C9 1.422(2) . ? O5 C8 1.433(2) . ? O6 C11 1.425(2) . ? O6 C10 1.4254(19) . ? O3 C5 1.425(2) . ? O3 C4 1.4293(19) . ? C6 C5 1.500(2) . ? C6 H6A 0.99 . ? C6 H6B 0.99 . ? C3 C4 1.495(2) . ? C3 H3A 0.99 . ? C3 H3B 0.99 . ? C12 C11 1.498(2) . ? C12 H12A 0.99 . ? C12 H12B 0.99 . ? C7 C8 1.484(2) . ? C7 H7A 0.99 . ? C7 H7B 0.99 . ? C8 H8A 0.99 . ? C8 H8B 0.99 . ? C9 C10 1.498(2) . ? C9 H9A 0.99 . ? C9 H9B 0.99 . ? C11 H11A 0.99 . ? C11 H11B 0.99 . ? N1 B1 1.579(3) . ? N1 HN3 0.859(19) . ? N1 HN2 0.85(2) . ? N1 HN1 0.94(2) . ? C5 H5A 0.99 . ? C5 H5B 0.99 . ? C4 H4A 0.99 . ? C4 H4B 0.99 . ? C10 H10A 0.99 . ? C10 H10B 0.99 . ? C2 C1 1.490(3) . ? C2 H2A 0.99 . ? C2 H2B 0.99 . ? C1 H1A 0.99 . ? C1 H1B 0.99 . ? N2 B1 1.576(3) . ? N2 B2 1.603(3) . ? N2 HN4 1.02(2) . ? N2 HN5 1.00(3) . ? B1 HB2 1.077(16) . ? B1 HB1 1.129(17) . ? B2 HB3 1.15(2) . ? B2 HB4 1.138(19) . ? B2 HB5 1.15(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 C6 O4 C7 112.02(12) . . ? C12 O1 C1 111.15(12) . . ? C3 O2 C2 111.21(12) . . ? C9 O5 C8 111.29(13) . . ? C11 O6 C10 111.90(12) . . ? C5 O3 C4 111.66(13) . . ? O4 C6 C5 109.37(14) . . ? O4 C6 H6A 109.8 . . ? C5 C6 H6A 109.8 . . ? O4 C6 H6B 109.8 . . ? C5 C6 H6B 109.8 . . ? H6A C6 H6B 108.2 . . ? O2 C3 C4 109.22(14) . . ? O2 C3 H3A 109.8 . . ? C4 C3 H3A 109.8 . . ? O2 C3 H3B 109.8 . . ? C4 C3 H3B 109.8 . . ? H3A C3 H3B 108.3 . . ? O1 C12 C11 109.48(14) . . ? O1 C12 H12A 109.8 . . ? C11 C12 H12A 109.8 . . ? O1 C12 H12B 109.8 . . ? C11 C12 H12B 109.8 . . ? H12A C12 H12B 108.2 . . ? O4 C7 C8 109.58(14) . . ? O4 C7 H7A 109.8 . . ? C8 C7 H7A 109.8 . . ? O4 C7 H7B 109.8 . . ? C8 C7 H7B 109.8 . . ? H7A C7 H7B 108.2 . . ? O5 C8 C7 109.97(15) . . ? O5 C8 H8A 109.7 . . ? C7 C8 H8A 109.7 . . ? O5 C8 H8B 109.7 . . ? C7 C8 H8B 109.7 . . ? H8A C8 H8B 108.2 . . ? O5 C9 C10 110.18(15) . . ? O5 C9 H9A 109.6 . . ? C10 C9 H9A 109.6 . . ? O5 C9 H9B 109.6 . . ? C10 C9 H9B 109.6 . . ? H9A C9 H9B 108.1 . . ? O6 C11 C12 109.15(14) . . ? O6 C11 H11A 109.9 . . ? C12 C11 H11A 109.9 . . ? O6 C11 H11B 109.9 . . ? C12 C11 H11B 109.9 . . ? H11A C11 H11B 108.3 . . ? B1 N1 HN3 111.9(12) . . ? B1 N1 HN2 116.4(13) . . ? HN3 N1 HN2 106.4(17) . . ? B1 N1 HN1 112.5(13) . . ? HN3 N1 HN1 103.9(17) . . ? HN2 N1 HN1 104.8(18) . . ? O3 C5 C6 108.83(14) . . ? O3 C5 H5A 109.9 . . ? C6 C5 H5A 109.9 . . ? O3 C5 H5B 109.9 . . ? C6 C5 H5B 109.9 . . ? H5A C5 H5B 108.3 . . ? O3 C4 C3 108.37(14) . . ? O3 C4 H4A 110 . . ? C3 C4 H4A 110 . . ? O3 C4 H4B 110 . . ? C3 C4 H4B 110 . . ? H4A C4 H4B 108.4 . . ? O6 C10 C9 109.28(14) . . ? O6 C10 H10A 109.8 . . ? C9 C10 H10A 109.8 . . ? O6 C10 H10B 109.8 . . ? C9 C10 H10B 109.8 . . ? H10A C10 H10B 108.3 . . ? O2 C2 C1 109.49(14) . . ? O2 C2 H2A 109.8 . . ? C1 C2 H2A 109.8 . . ? O2 C2 H2B 109.8 . . ? C1 C2 H2B 109.8 . . ? H2A C2 H2B 108.2 . . ? O1 C1 C2 109.98(14) . . ? O1 C1 H1A 109.7 . . ? C2 C1 H1A 109.7 . . ? O1 C1 H1B 109.7 . . ? C2 C1 H1B 109.7 . . ? H1A C1 H1B 108.2 . . ? B1 N2 B2 117.10(17) . . ? B1 N2 HN4 108.3(13) . . ? B2 N2 HN4 105.6(12) . . ? B1 N2 HN5 115.3(15) . . ? B2 N2 HN5 104.4(15) . . ? HN4 N2 HN5 105.2(19) . . ? N2 B1 N1 108.27(17) . . ? N2 B1 HB2 111.3(8) . . ? N1 B1 HB2 106.2(9) . . ? N2 B1 HB1 110.3(8) . . ? N1 B1 HB1 108.1(8) . . ? HB2 B1 HB1 112.4(11) . . ? N2 B2 HB3 106.2(10) . . ? N2 B2 HB4 105.8(9) . . ? HB3 B2 HB4 114.0(14) . . ? N2 B2 HB5 108.3(10) . . ? HB3 B2 HB5 111.5(14) . . ? HB4 B2 HB5 110.6(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 HN2 O2 0.85(2) 2.26(2) 3.063(2) 156.8(17) . N1 HN1 O4 0.94(2) 2.04(2) 2.953(2) 163.2(18) . N1 HN3 O6 0.859(19) 2.244(19) 3.067(2) 160.4(16) . # END of CIF data_I _database_code_depnum_ccdc_archive 'CCDC 896621' #TrackingRef 'anti.cif' _chemical_name_systematic ? _chemical_name_common OSU2 _chemical_formula_moiety 'B2 H10 N2' _chemical_formula_sum 'B2 H10 N2' _chemical_formula_iupac ? _chemical_formula_weight 59.72 _chemical_absolute_configuration unk _chemical_melting_point ? _space_group_crystal_system monoclinic _space_group_name_H-M_alt 'P 1 n 1' _space_group_name_Hall 'P -2yac' loop_ _space_group_symop_operation_xyz 'x, y, z' 'x+1/2, -y, z+1/2' _cell_length_a 7.3061(8) _cell_length_b 4.4678(5) _cell_length_c 7.3183(8) _cell_angle_alpha 90 _cell_angle_beta 117.245(7) _cell_angle_gamma 90 _cell_volume 212.38(4) _cell_formula_units_Z 2 _cell_measurement_reflns_used 1310 _cell_measurement_theta_min 7.0944 _cell_measurement_theta_max 66.2774 _cell_measurement_temperature 100.(2) _exptl_crystal_description powder _exptl_crystal_colour colorless _exptl_crystal_size_max 0.103 _exptl_crystal_size_mid 0.074 _exptl_crystal_size_min 0.069 _exptl_crystal_density_diffrn 0.934 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 68 _exptl_absorpt_coefficient_mu 0.410 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _exptl_absorpt_correction_T_min 0.800 _exptl_absorpt_correction_T_max 0.972 _exptl_special_details ; ; _diffrn_ambient_temperature 100.(2) _diffrn_source 'ImuS micro-focus source with Quazar MX optics' _diffrn_source_type ? _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_monochromator ? _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean 8.3333 _diffrn_reflns_number 1719 _diffrn_reflns_av_R_equivalents 0.0243 _diffrn_reflns_av_sigmaI/netI 0.0285 _diffrn_reflns_theta_min 6.80 _diffrn_reflns_theta_max 66.26 _diffrn_reflns_theta_full 66.26 _diffrn_measured_fraction_theta_max 0.968 _diffrn_measured_fraction_theta_full 0.968 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _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. ; _reflns_number_total 693 _reflns_number_gt 662 _reflns_threshold_expression >2sigma(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0386 _refine_ls_R_factor_gt 0.0366 _refine_ls_wR_factor_gt 0.0966 _refine_ls_wR_factor_ref 0.0990 _refine_ls_goodness_of_fit_ref 1.105 _refine_ls_restrained_S_all 1.103 _refine_ls_number_reflns 693 _refine_ls_number_parameters 50 _refine_ls_number_restraints 2 _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0701P)^2^+0.0007P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.172 _refine_diff_density_min -0.147 _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 -0.2(7) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source B B 0.0090 0.0039 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_data_collection 'Bruker Instrument Service v2011.8.0.0' _computing_cell_refinement 'SAINT V7.68A (Bruker AXS, 2009)' _computing_data_reduction 'SAINT V7.68A (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group N N1 0.7461(3) 0.7551(3) 0.3912(3) 0.0249(9) Uani d . 1 . . H H1NA 0.7775 0.6739 0.2949 0.034(7) Uiso calc R 1 . . H H1NB 0.8405 0.6948 0.5185 0.045(9) Uiso calc R 1 . . H H1NC 0.7479 0.9582 0.3834 0.054(9) Uiso calc R 1 . . B B1 0.5224(4) 0.6468(6) 0.3503(4) 0.0245(11) Uani d . 1 . . H H1BA 0.4181 0.7268 0.2169 0.039(9) Uiso calc R 1 . . H H1BB 0.5155 0.4255 0.3432 0.016(6) Uiso calc R 1 . . N N2 0.4751(3) 0.7568(3) 0.5243(3) 0.0262(11) Uani d . 1 . . H H2NA 0.4829 0.9624 0.5305 0.033(7) Uiso calc R 1 . . H H2NB 0.5735 0.6832 0.6477 0.015(6) Uiso calc R 1 . . B B2 0.2523(4) 0.6551(6) 0.4926(4) 0.0258(11) Uani d . 1 . . H H2BA 0.2295 0.7319 0.6059 0.094(18) Uiso calc R 1 . . H H2BB 0.2445 0.4361 0.4902 0.054(11) Uiso calc R 1 . . H H2BC 0.1466 0.7351 0.3621 0.040(9) Uiso calc R 1 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 N1 0.028(3) 0.0217(19) 0.0241(18) 0.0007(7) 0.0113(17) -0.0002(7) B1 0.028(3) 0.021(2) 0.0197(18) -0.0015(12) 0.0069(17) 0.0005(11) N2 0.027(3) 0.023(2) 0.0226(18) 0.0011(8) 0.0069(17) 0.0025(7) B2 0.026(3) 0.025(2) 0.025(2) 0.0019(11) 0.0099(19) 0.0024(11) _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_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N1 B1 . 1.596(4) ? B1 N2 . 1.545(3) ? N2 B2 . 1.601(4) ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag N2 B1 N1 . . 110.2(2) ? B1 N2 B2 . . 112.7(2) ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag N1 B1 N2 B2 . . . . -179.94(19) ?