Electronic Supplementary Material for CrystEngComm This journal is © The Royal SOciety of Chemistry 2006 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Kenneth E. Maly' _publ_contact_author_address ; Departement de Chimie Universite de Montreal Montreal, Quebec, H3C 3J7 Canada ; _publ_contact_author_email james.d.wuest@umontreal.ca loop_ _publ_author_name _publ_author_address K.E.Maly ; Departement de Chimie Universite de Montreal Montreal, Quebec, H3C 3J7 Canada ; T.Maris ; Departement de Chimie Universite de Montreal Montreal, Quebec, H3C 3J7 Canada ; J.D.Wuest ; Departement de Chimie Universite de Montreal Montreal, Quebec, H3C 3J7 Canada ; _publ_section_title ; Two-Dimensional Hydrogen-Bonded Networks in Crystals of Diboronic Acids ; data_jiw897 _database_code_depnum_ccdc_archive 'CCDC 283685' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H12 B2 O4, 3(C4 H8 O)' _chemical_formula_sum 'C26 H36 B2 O7' _chemical_formula_weight 482.17 _chemical_compound_source 'Synthesized by the authors. See text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 '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 6.5411(6) _cell_length_b 9.4198(9) _cell_length_c 10.8119(11) _cell_angle_alpha 92.161(5) _cell_angle_beta 104.384(6) _cell_angle_gamma 96.514(5) _cell_volume 639.63(11) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2877 _cell_measurement_theta_min 4.23 _cell_measurement_theta_max 67.41 _exptl_crystal_description block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.252 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 258 _exptl_absorpt_coefficient_mu 0.715 _exptl_absorpt_correction_Type multi-scan _exptl_absorpt_correction_T_min 0.9200 _exptl_absorpt_correction_T_max 0.9600 _exptl_absorpt_process_details 'Sadabs (Sheldrick,1996)' _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator 'Montel 200 optics' _diffrn_measurement_device_type 'Bruker Smart 6000' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 5.5 _diffrn_standards_number 44 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 1440 _diffrn_standards_decay_% -0.90 _diffrn_reflns_number 7257 _diffrn_reflns_av_R_equivalents 0.062 _diffrn_reflns_av_sigmaI/netI 0.0517 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 4.23 _diffrn_reflns_theta_max 67.38 _reflns_number_total 2147 _reflns_number_gt 1546 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2003)' _computing_cell_refinement 'SMART (Bruker, 2003)' _computing_data_reduction 'SAINT (Bruker, 2004)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 1997)' _computing_publication_material 'UdMX (local program)' _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^)+(0.1010P)^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_number_reflns 2147 _refine_ls_number_parameters 146 _refine_ls_number_restraints 22 _refine_ls_R_factor_all 0.0749 _refine_ls_R_factor_gt 0.0719 _refine_ls_wR_factor_ref 0.1764 _refine_ls_wR_factor_gt 0.1756 _refine_ls_goodness_of_fit_ref 1.113 _refine_ls_restrained_S_all 1.254 _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 B1 B 0.1289(9) 1.3770(5) 0.3829(5) 0.0411(13) Uani 1 1 d . . . O1 O -0.0414(5) 1.3152(3) 0.4195(3) 0.0433(9) Uani 1 1 d . . . H1 H -0.073(7) 1.372(5) 0.490(4) 0.041(12) Uiso 1 1 d . . . O2 O 0.2075(5) 1.5160(3) 0.4256(3) 0.0418(9) Uani 1 1 d . . . H2 H 0.306(8) 1.563(6) 0.414(5) 0.042(14) Uiso 1 1 d . . . C1 C 0.4661(7) 1.0331(5) 0.0377(4) 0.0406(11) Uani 1 1 d . . . C2 C 0.3866(7) 1.1163(4) 0.1255(4) 0.0398(12) Uani 1 1 d . . . C3 C 0.1896(7) 1.0742(5) 0.1487(4) 0.0438(12) Uani 1 1 d . . . H3 H 0.1073 0.9882 0.1070 0.053 Uiso 1 1 calc . . . C4 C 0.1113(7) 1.1554(5) 0.2315(5) 0.0437(12) Uani 1 1 d . . . H4 H -0.0234 1.1243 0.2462 0.052 Uiso 1 1 calc . . . C5 C 0.2285(7) 1.2830(4) 0.2938(4) 0.0395(12) Uani 1 1 d . . . C6 C 0.4278(7) 1.3224(5) 0.2734(4) 0.0444(12) Uani 1 1 d . . . H6 H 0.5108 1.4078 0.3160 0.053 Uiso 1 1 calc . . . C7 C 0.5085(8) 1.2403(5) 0.1922(5) 0.0473(13) Uani 1 1 d . . . H7 H 0.6471 1.2682 0.1818 0.057 Uiso 1 1 calc . . . C10 C 0.4996(8) 0.1660(5) 0.6114(5) 0.0566(15) Uani 1 1 d . . . H10A H 0.6097 0.1388 0.6842 0.068 Uiso 1 1 calc R . . H10B H 0.5434 0.1502 0.5311 0.068 Uiso 1 1 calc R . . O10 O 0.4624(5) 0.3084(3) 0.6293(3) 0.0531(10) Uani 1 1 d D . . C11 C 0.2903(8) 0.0867(5) 0.6044(5) 0.0521(13) Uani 1 1 d D . . H11A H 0.3046 -0.0131 0.6276 0.063 Uiso 1 1 calc R . . H11B H 0.1968 0.0845 0.5168 0.063 Uiso 1 1 calc R . . C12 C 0.2014(8) 0.1631(5) 0.6962(5) 0.0538(14) Uani 1 1 d D . . H12A H 0.2293 0.1186 0.7793 0.065 Uiso 1 1 calc R . . H12B H 0.0459 0.1621 0.6628 0.065 Uiso 1 1 calc R . . C13 C 0.3135(7) 0.3130(5) 0.7107(4) 0.0511(13) Uani 1 1 d D . . H13A H 0.2115 0.3822 0.6812 0.061 Uiso 1 1 calc R . . H13B H 0.3906 0.3401 0.8010 0.061 Uiso 1 1 calc R . . O30 O 0.8273(7) 0.4168(5) 0.9787(4) 0.079(2) Uiso 0.25 1 d PRD A -1 C30 C 0.8797(7) 0.4861(5) 1.0964(4) 0.079(2) Uiso 0.25 1 d PRD A -1 H30A H 0.7532 0.5015 1.1275 0.095 Uiso 0.25 1 calc PR B -1 H30B H 0.9789 0.4372 1.1604 0.095 Uiso 0.25 1 calc PR C -1 C31 C 0.9679(7) 0.5990(5) 1.0658(4) 0.079(2) Uiso 0.25 1 d PRD A -1 H31A H 0.9994 0.6713 1.1391 0.095 Uiso 0.25 1 calc PR D -1 H31B H 0.8666 0.6356 0.9939 0.095 Uiso 0.25 1 calc PR E -1 C32 C 1.1750(7) 0.5845(5) 1.0264(4) 0.079(2) Uiso 0.25 1 d PRD A -1 H32A H 1.2990 0.5765 1.0989 0.095 Uiso 0.25 1 calc PR F -1 H32B H 1.2100 0.6573 0.9686 0.095 Uiso 0.25 1 calc PR G -1 C33 C 1.0343(7) 0.4023(5) 0.9393(4) 0.079(2) Uiso 0.25 1 d PRD A -1 H33A H 1.0158 0.4000 0.8455 0.095 Uiso 0.25 1 calc PR H -1 H33B H 1.1043 0.3197 0.9750 0.095 Uiso 0.25 1 calc PR I -1 O40 O 0.9776(7) 0.4005(5) 0.9253(4) 0.072(3) Uiso 0.25 1 d PRD J -2 C40 C 1.1226(7) 0.5152(5) 0.9087(4) 0.072(3) Uiso 0.25 1 d PRD J -2 H40A H 1.0353 0.5918 0.8766 0.086 Uiso 0.25 1 calc PR K -2 H40B H 1.1778 0.4825 0.8366 0.086 Uiso 0.25 1 calc PR L -2 C41 C 1.3104(7) 0.5883(5) 1.0049(4) 0.072(3) Uiso 0.25 1 d PRD J -2 H41A H 1.3708 0.6815 0.9814 0.086 Uiso 0.25 1 calc PR M -2 H41B H 1.4219 0.5269 1.0392 0.086 Uiso 0.25 1 calc PR N -2 C42 C 1.1125(7) 0.5987(5) 1.0972(4) 0.072(3) Uiso 0.25 1 d PRD J -2 H42A H 1.0981 0.7008 1.1134 0.086 Uiso 0.25 1 calc PR O -2 H42B H 1.1660 0.5596 1.1812 0.086 Uiso 0.25 1 calc PR P -2 C43 C 0.8399(7) 0.5002(5) 1.0188(4) 0.072(3) Uiso 0.25 1 d PRD J -2 H43A H 0.7744 0.4424 1.0767 0.086 Uiso 0.25 1 calc PR Q -2 H43B H 0.7393 0.5603 0.9684 0.086 Uiso 0.25 1 calc PR R -2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 B1 0.044(3) 0.035(3) 0.053(3) 0.001(2) 0.024(3) 0.015(2) O1 0.0461(19) 0.0324(17) 0.063(2) -0.0008(14) 0.0331(17) 0.0103(14) O2 0.048(2) 0.0285(17) 0.061(2) 0.0009(13) 0.0354(17) 0.0108(14) C1 0.038(3) 0.034(2) 0.055(3) 0.0023(19) 0.018(2) 0.0139(19) C2 0.044(3) 0.034(2) 0.051(3) 0.009(2) 0.024(2) 0.018(2) C3 0.052(3) 0.035(2) 0.052(3) 0.003(2) 0.024(2) 0.014(2) C4 0.049(3) 0.034(2) 0.061(3) 0.004(2) 0.033(2) 0.015(2) C5 0.047(3) 0.032(2) 0.051(3) 0.012(2) 0.027(2) 0.018(2) C6 0.045(3) 0.042(3) 0.055(3) 0.000(2) 0.025(2) 0.017(2) C7 0.052(3) 0.044(3) 0.059(3) 0.005(2) 0.032(2) 0.021(2) C10 0.066(3) 0.044(3) 0.079(4) 0.016(2) 0.043(3) 0.028(3) O10 0.061(2) 0.0337(17) 0.081(2) 0.0055(16) 0.0474(19) 0.0115(15) C11 0.060(3) 0.039(3) 0.071(3) 0.015(2) 0.035(3) 0.016(2) C12 0.053(3) 0.056(3) 0.062(3) 0.016(2) 0.029(3) 0.015(2) C13 0.053(3) 0.045(3) 0.067(3) 0.002(2) 0.032(3) 0.015(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_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag B1 O1 . . 1.351(6) Y B1 O2 . . 1.369(6) Y B1 C5 . . 1.586(6) Y O1 H1 . . 0.99(5) ? O2 H2 . . 0.78(5) ? C1 C1 . 2_675 1.206(9) Y C1 C2 . . 1.438(6) Y C2 C3 . . 1.391(6) Y C2 C7 . . 1.400(7) Y C3 C4 . . 1.383(6) Y C3 H3 . . 0.95 ? C4 C5 . . 1.400(7) Y C4 H4 . . 0.95 ? C5 C6 . . 1.388(6) Y C6 C7 . . 1.385(6) Y C6 H6 . . 0.95 ? C7 H7 . . 0.95 ? C10 O10 . . 1.405(6) Y C10 C11 . . 1.467(7) Y C10 H10a . . 0.99 ? C10 H10b . . 0.99 ? O10 C13 . . 1.469(5) Y C11 C12 . . 1.473(6) Y C11 H11a . . 0.99 ? C11 H11b . . 0.99 ? C12 C13 . . 1.499(6) Y C12 H12a . . 0.99 ? C12 H12b . . 0.99 ? C13 H13a . . 0.99 ? C13 H13b . . 0.99 ? O30 C30 . . 1.354 Y O30 C33 . . 1.536 Y C30 C31 . . 1.247 Y C30 H30a . . 0.99 ? C30 H30b . . 0.99 ? C31 C32 . . 1.5359 Y C31 H31a . . 0.99 ? C31 H31b . . 0.99 ? C32 H32a . . 0.99 ? C32 H32b . . 0.99 ? C33 H33a . . 0.99 ? C33 H33b . . 0.99 ? O40 C40 . . 1.402 Y C40 C41 . . 1.478 Y C40 H40a . . 0.99 ? C40 H40b . . 0.99 ? C41 H41a . . 0.99 ? C41 H41b . . 0.99 ? C42 H42a . . 0.99 ? C42 H42b . . 0.99 ? C43 H43a . . 0.99 ? C43 H43b . . 0.99 ? 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_2 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O1 B1 O2 . . . 118.6(4) Y O1 B1 C5 . . . 117.8(4) Y O2 B1 C5 . . . 123.6(4) Y B1 O1 H1 . . . 113(3) ? B1 O2 H2 . . . 129(4) ? C1 C1 C2 2_675 . . 178.1(6) Y C3 C2 C7 . . . 118.3(4) Y C3 C2 C1 . . . 121.1(4) Y C7 C2 C1 . . . 120.6(4) Y C4 C3 C2 . . . 121.1(4) Y C4 C3 H3 . . . 119.4 ? C2 C3 H3 . . . 119.4 ? C3 C4 C5 . . . 120.7(4) Y C3 C4 H4 . . . 119.6 ? C5 C4 H4 . . . 119.6 ? C6 C5 C4 . . . 117.9(4) Y C6 C5 B1 . . . 122.8(4) Y C4 C5 B1 . . . 119.3(4) Y C7 C6 C5 . . . 121.6(5) Y C7 C6 H6 . . . 119.2 ? C5 C6 H6 . . . 119.2 ? C6 C7 C2 . . . 120.3(4) Y C6 C7 H7 . . . 119.9 ? C2 C7 H7 . . . 119.9 ? O10 C10 C11 . . . 101.9(3) Y O10 C10 H10A . . . 111.4 ? C11 C10 H10A . . . 111.4 ? O10 C10 H10B . . . 111.4 ? C11 C10 H10B . . . 111.4 ? H10A C10 H10B . . . 109.3 ? C10 O10 C13 . . . 109.0(3) Y C10 C11 C12 . . . 106.2(4) Y C10 C11 H11A . . . 110.5 ? C12 C11 H11A . . . 110.5 ? C10 C11 H11B . . . 110.5 ? C12 C11 H11B . . . 110.5 ? H11A C11 H11B . . . 108.7 ? C11 C12 C13 . . . 104.8(4) Y C11 C12 H12A . . . 110.8 ? C13 C12 H12A . . . 110.8 ? C11 C12 H12B . . . 110.8 ? C13 C12 H12B . . . 110.8 ? H12A C12 H12B . . . 108.9 ? O10 C13 C12 . . . 104.0(3) Y O10 C13 H13A . . . 111 ? C12 C13 H13A . . . 111 ? O10 C13 H13B . . . 111 ? C12 C13 H13B . . . 111 ? H13A C13 H13B . . . 109 ? C30 O30 C33 . . . 107.9 Y C31 C30 O30 . . . 96.5 Y C31 C30 H30A . . . 112.5 ? O30 C30 H30A . . . 112.5 ? C31 C30 H30B . . . 112.5 ? O30 C30 H30B . . . 112.5 ? H30A C30 H30B . . . 110 ? C30 C31 C32 . . . 115.1 Y C30 C31 H31A . . . 108.5 ? C32 C31 H31A . . . 108.5 ? C30 C31 H31B . . . 108.5 ? C32 C31 H31B . . . 108.5 ? H31A C31 H31B . . . 107.5 ? C31 C32 C33 . . . 86.7 Y C31 C32 H32A . . . 114.2 ? C33 C32 H32A . . . 114.2 ? C31 C32 H32B . . . 114.2 ? C33 C32 H32B . . . 114.2 ? H32A C32 H32B . . . 111.4 ? O30 C33 C32 . . . 93.3 Y O30 C33 H33A . . . 113 ? C32 C33 H33A . . . 113 ? O30 C33 H33B . . . 113 ? C32 C33 H33B . . . 113 ? H33A C33 H33B . . . 110.4 ? C40 O40 C43 . . . 97.3 Y O40 C40 C41 . . . 127.7 Y O40 C40 H40A . . . 105.4 ? C41 C40 H40A . . . 105.4 ? O40 C40 H40B . . . 105.4 ? C41 C40 H40B . . . 105.4 ? H40A C40 H40B . . . 106 ? C40 C41 C42 . . . 81.6 Y C40 C41 H41A . . . 115 ? C42 C41 H41A . . . 115 ? C40 C41 H41B . . . 115 ? C42 C41 H41B . . . 115 ? H41A C41 H41B . . . 112.1 ? C41 C42 C43 . . . 115 Y C41 C42 H42A . . . 108.5 ? C43 C42 H42A . . . 108.5 ? C41 C42 H42B . . . 108.5 ? C43 C42 H42B . . . 108.5 ? H42A C42 H42B . . . 107.5 ? O40 C43 C42 . . . 85.1 Y O40 C43 H43A . . . 114.5 ? C42 C43 H43A . . . 114.5 ? O40 C43 H43B . . . 114.5 ? C42 C43 H43B . . . 114.5 ? H43A C43 H43B . . . 111.6 ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C7 C2 C3 C4 . . . . 2.6(7) Y C1 C2 C3 C4 . . . . -178.9(4) Y C2 C3 C4 C5 . . . . 0.3(7) Y C3 C4 C5 C6 . . . . -2.2(7) Y C3 C4 C5 B1 . . . . 177.1(4) Y O1 B1 C5 C6 . . . . -165.3(4) Y O2 B1 C5 C6 . . . . 13.8(7) Y O1 B1 C5 C4 . . . . 15.4(7) Y O2 B1 C5 C4 . . . . -165.4(4) Y C4 C5 C6 C7 . . . . 1.1(7) Y B1 C5 C6 C7 . . . . -178.2(4) Y C5 C6 C7 C2 . . . . 1.8(7) Y C3 C2 C7 C6 . . . . -3.7(7) Y C1 C2 C7 C6 . . . . 177.8(4) Y C11 C10 O10 C13 . . . . 36.1(5) Y O10 C10 C11 C12 . . . . -36.6(5) Y C10 C11 C12 C13 . . . . 23.6(5) Y C10 O10 C13 C12 . . . . -21.8(5) Y C11 C12 C13 O10 . . . . -1.9(5) Y C33 O30 C30 C31 . . . . 61 Y O30 C30 C31 C32 . . . . -66.8 Y C30 C31 C32 C33 . . . . 39.7 Y C30 O30 C33 C32 . . . . -34 Y C31 C32 C33 O30 . . . . 0 Y C43 O40 C40 C41 . . . . 73.4 Y O40 C40 C41 C42 . . . . -51.3 Y C40 C41 C42 C43 . . . . 5.9 Y C40 O40 C43 C42 . . . . -38.7 Y C41 C42 C43 O40 . . . . 20.6 Y 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 O1 H1 O2 0.99(5) 1.81(5) 2.759(4) 161(4) 2_586 O2 H2 O10 0.78(5) 1.99(5) 2.767(4) 174(5) 2_676 _diffrn_measured_fraction_theta_max 0.935 _diffrn_reflns_theta_full 67.38 _diffrn_measured_fraction_theta_full 0.935 _refine_diff_density_max 0.263 _refine_diff_density_min -0.338 _refine_diff_density_rms 0.073 data_jiw890 _database_code_depnum_ccdc_archive 'CCDC 283686' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H12 B2 O4, 3(C4 H8 O2)' _chemical_formula_sum 'C26 H36 B2 O10' _chemical_formula_weight 530.17 _chemical_compound_source 'Synthesized by the authors. See text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 '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 6.7104(4) _cell_length_b 7.4452(4) _cell_length_c 14.1376(8) _cell_angle_alpha 94.672(2) _cell_angle_beta 102.780(3) _cell_angle_gamma 98.325(3) _cell_volume 676.83(7) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5344 _cell_measurement_theta_min 3.23 _cell_measurement_theta_max 68.18 _exptl_crystal_description block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.301 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 282 _exptl_absorpt_coefficient_mu 0.810 _exptl_absorpt_correction_Type multi-scan _exptl_absorpt_correction_T_min 0.840 _exptl_absorpt_correction_T_max 0.930 _exptl_absorpt_process_details 'Sadabs (Sheldrick,1996)' _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator 'Montel 200 Optics' _diffrn_measurement_device_type 'Bruker Smart 6000' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 5.5 _diffrn_standards_number 33 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 1440 _diffrn_standards_decay_% 1.63 _diffrn_reflns_number 8385 _diffrn_reflns_av_R_equivalents 0.065 _diffrn_reflns_av_sigmaI/netI 0.0395 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.23 _diffrn_reflns_theta_max 68.20 _diffrn_measured_fraction_theta_max 0.960 _diffrn_reflns_theta_full 68.20 _diffrn_measured_fraction_theta_full 0.960 _reflns_number_total 2359 _reflns_number_gt 2062 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2003)' _computing_cell_refinement 'SMART (Bruker, 2003)' _computing_data_reduction 'SAINT (Bruker, 2004)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 1997)' _computing_publication_material 'UdMX (local program)' _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^)+(0.1556P)^2^+0.0764P] 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 2359 _refine_ls_number_parameters 198 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0773 _refine_ls_R_factor_gt 0.0725 _refine_ls_wR_factor_ref 0.2043 _refine_ls_wR_factor_gt 0.1930 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _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 B1 B 0.3584(4) 0.4774(3) 0.61470(14) 0.0362(5) Uani 1 1 d . . . O1 O 0.2945(2) 0.57211(17) 0.53760(8) 0.0378(4) Uani 1 1 d . . . H1 H 0.198(4) 0.645(4) 0.542(2) 0.064(7) Uiso 1 1 d . . . O2 O 0.5149(2) 0.38162(19) 0.61382(9) 0.0434(4) Uani 1 1 d . . . H2 H 0.562(4) 0.385(4) 0.556(2) 0.078(9) Uiso 1 1 d . . . C1 C 0.0300(3) 0.4973(2) 0.96262(12) 0.0316(5) Uani 1 1 d . . . C2 C 0.1059(3) 0.4906(2) 0.87586(11) 0.0298(5) Uani 1 1 d . . . C3 C -0.0085(3) 0.5380(2) 0.78935(12) 0.0316(4) Uani 1 1 d . . . H3 H -0.1390 0.5748 0.7874 0.038 Uiso 1 1 calc . . . C4 C 0.0692(3) 0.5314(2) 0.70569(12) 0.0328(5) Uani 1 1 d . . . H4 H -0.0097 0.5634 0.6469 0.039 Uiso 1 1 calc . . . C5 C 0.2621(3) 0.4783(2) 0.70676(12) 0.0334(5) Uani 1 1 d . . . C6 C 0.3725(3) 0.4288(2) 0.79338(12) 0.0337(5) Uani 1 1 d . . . H6 H 0.5025 0.3911 0.7953 0.040 Uiso 1 1 calc . . . C7 C 0.2966(3) 0.4333(2) 0.87709(12) 0.0312(4) Uani 1 1 d . . . H7 H 0.3738 0.3975 0.9353 0.037 Uiso 1 1 calc . . . C10 C 0.1637(3) 0.0068(3) 0.16191(16) 0.0453(5) Uani 1 1 d . . . H10A H 0.0371 0.0623 0.1443 0.054 Uiso 1 1 calc R . . H10B H 0.1240 -0.1145 0.1826 0.054 Uiso 1 1 calc R . . O10 O 0.3077(2) 0.11938(18) 0.24082(10) 0.0431(4) Uani 1 1 d . . . C11 C 0.2534(3) -0.0169(3) 0.07359(14) 0.0449(5) Uani 1 1 d . . . H11A H 0.1509 -0.0988 0.0207 0.054 Uiso 1 1 calc R . . H11B H 0.2834 0.1031 0.0497 0.054 Uiso 1 1 calc R . . C12 C 0.5825(3) 0.0233(3) 0.17479(15) 0.0440(5) Uani 1 1 d . . . H12A H 0.6175 0.1451 0.1536 0.053 Uiso 1 1 calc R . . H12B H 0.7115 -0.0290 0.1918 0.053 Uiso 1 1 calc R . . O12 O 0.4383(2) -0.09211(17) 0.09731(9) 0.0414(4) Uani 1 1 d . . . C13 C 0.4936(3) 0.0436(3) 0.26333(14) 0.0428(5) Uani 1 1 d . . . H13A H 0.4639 -0.0775 0.2861 0.051 Uiso 1 1 calc R . . H13B H 0.5964 0.1241 0.3167 0.051 Uiso 1 1 calc R . . O13 O 0.0366(3) 0.82369(19) 0.51385(12) 0.0637(6) Uani 1 1 d . . . C20 C 0.0533(9) 0.9071(6) 0.4230(3) 0.0406(10) Uani 0.50 1 d P . 1 H20A H 0.1453 0.8479 0.3891 0.049 Uiso 0.50 1 calc PR . 1 H20B H -0.0847 0.8962 0.3778 0.049 Uiso 0.50 1 calc PR . 1 C21 C -0.1414(9) 0.9018(6) 0.5425(3) 0.0434(10) Uani 0.50 1 d P . 1 H21A H -0.2607 0.8912 0.4856 0.052 Uiso 0.50 1 calc PR . 1 H21B H -0.1871 0.8385 0.5948 0.052 Uiso 0.50 1 calc PR . 1 C22 C -0.0148(7) 0.9466(5) 0.5911(3) 0.0308(8) Uani 0.50 1 d P . 2 H22A H 0.1101 1.0312 0.6290 0.037 Uiso 0.50 1 calc PR . 2 H22B H -0.0777 0.8751 0.6363 0.037 Uiso 0.50 1 calc PR . 2 C23 C 0.1692(7) 0.9502(5) 0.4678(3) 0.0271(7) Uani 0.50 1 d P . 2 H23A H 0.2380 0.8818 0.4250 0.033 Uiso 0.50 1 calc PR . 2 H23B H 0.2761 1.0343 0.5178 0.033 Uiso 0.50 1 calc PR . 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 B1 0.0554(13) 0.0430(11) 0.0210(9) 0.0096(8) 0.0250(9) 0.0158(9) O1 0.0604(9) 0.0456(8) 0.0230(7) 0.0135(5) 0.0301(6) 0.0233(7) O2 0.0641(10) 0.0600(9) 0.0263(7) 0.0209(6) 0.0344(6) 0.0309(7) C1 0.0510(11) 0.0306(9) 0.0204(8) 0.0046(6) 0.0216(7) 0.0092(7) C2 0.0493(11) 0.0290(8) 0.0195(8) 0.0051(6) 0.0233(7) 0.0091(7) C3 0.0468(11) 0.0348(9) 0.0223(8) 0.0067(7) 0.0233(7) 0.0115(7) C4 0.0512(11) 0.0393(9) 0.0172(8) 0.0103(6) 0.0203(7) 0.0153(7) C5 0.0525(11) 0.0374(9) 0.0211(9) 0.0091(7) 0.0247(8) 0.0152(8) C6 0.0488(11) 0.0381(9) 0.0244(9) 0.0093(7) 0.0241(8) 0.0141(8) C7 0.0487(11) 0.0345(9) 0.0174(8) 0.0082(6) 0.0178(7) 0.0120(7) C10 0.0489(12) 0.0431(10) 0.0504(12) 0.0035(9) 0.0222(9) 0.0137(8) O10 0.0590(9) 0.0409(7) 0.0388(8) 0.0020(6) 0.0269(7) 0.0164(6) C11 0.0633(14) 0.0416(10) 0.0347(10) 0.0058(8) 0.0131(9) 0.0213(9) C12 0.0501(12) 0.0407(10) 0.0501(12) 0.0086(8) 0.0260(9) 0.0130(8) O12 0.0624(9) 0.0418(7) 0.0311(7) 0.0083(6) 0.0242(6) 0.0223(6) C13 0.0585(13) 0.0401(10) 0.0331(10) 0.0017(8) 0.0154(9) 0.0138(8) O13 0.1206(14) 0.0433(8) 0.0696(11) 0.0338(8) 0.0810(10) 0.0466(9) C20 0.066(3) 0.043(2) 0.028(2) 0.0128(17) 0.032(2) 0.020(2) C21 0.067(3) 0.045(2) 0.035(2) 0.0105(18) 0.038(2) 0.021(2) C22 0.051(2) 0.0359(19) 0.0173(17) 0.0097(14) 0.0216(17) 0.0211(17) C23 0.040(2) 0.0310(18) 0.0204(18) 0.0098(14) 0.0203(16) 0.0144(15) _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_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag B1 O2 . . 1.354(2) Y B1 O1 . . 1.369(2) Y B1 C5 . . 1.576(2) Y O1 H1 . . 0.91(3) ? O2 H2 . . 0.94(3) ? C1 C1 . 2_567 1.211(3) Y C1 C2 . . 1.429(2) Y C2 C3 . . 1.394(3) Y C2 C7 . . 1.403(3) Y C3 C4 . . 1.394(2) Y C3 H3 . . 0.95 ? C4 C5 . . 1.404(3) Y C4 H4 . . 0.95 ? C5 C6 . . 1.391(3) Y C6 C7 . . 1.388(2) Y C6 H6 . . 0.95 ? C7 H7 . . 0.95 ? C10 O10 . . 1.420(2) Y C10 C11 . . 1.510(3) Y C10 H10a . . 0.99 ? C10 H10b . . 0.99 ? O10 C13 . . 1.426(2) Y C11 O12 . . 1.419(2) Y C11 H11a . . 0.99 ? C11 H11b . . 0.99 ? C12 O12 . . 1.418(2) Y C12 C13 . . 1.507(3) Y C12 H12a . . 0.99 ? C12 H12b . . 0.99 ? C13 H13a . . 0.99 ? C13 H13b . . 0.99 ? O13 C23 . . 1.489(4) Y O13 C20 . . 1.490(4) Y O13 C22 . . 1.498(3) Y O13 C21 . . 1.518(4) Y C20 C21 . 2_576 1.458(7) Y C20 H20a . . 0.99 ? C20 H20b . . 0.99 ? C21 C20 . 2_576 1.458(7) Y C21 H21a . . 0.99 ? C21 H21b . . 0.99 ? C22 C23 . 2_576 1.520(5) Y C22 H22a . . 0.99 ? C22 H22b . . 0.99 ? C23 C22 . 2_576 1.520(5) Y C23 H23a . . 0.99 ? C23 H23b . . 0.99 ? 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_2 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O2 B1 O1 . . . 119.09(15) Y O2 B1 C5 . . . 117.82(16) Y O1 B1 C5 . . . 123.07(17) Y B1 O1 H1 . . . 118.0(17) ? B1 O2 H2 . . . 113.0(17) ? C1 C1 C2 2_567 . . 178.5(3) Y C3 C2 C7 . . . 119.44(14) Y C3 C2 C1 . . . 120.78(16) Y C7 C2 C1 . . . 119.77(15) Y C2 C3 C4 . . . 119.77(16) Y C2 C3 H3 . . . 120.1 ? C4 C3 H3 . . . 120.1 ? C3 C4 C5 . . . 121.22(16) Y C3 C4 H4 . . . 119.4 ? C5 C4 H4 . . . 119.4 ? C6 C5 C4 . . . 118.12(15) Y C6 C5 B1 . . . 119.46(17) Y C4 C5 B1 . . . 122.41(16) Y C7 C6 C5 . . . 121.40(17) Y C7 C6 H6 . . . 119.3 ? C5 C6 H6 . . . 119.3 ? C6 C7 C2 . . . 120.02(16) Y C6 C7 H7 . . . 120 ? C2 C7 H7 . . . 120 ? O10 C10 C11 . . . 111.58(16) Y O10 C10 H10A . . . 109.3 ? C11 C10 H10A . . . 109.3 ? O10 C10 H10B . . . 109.3 ? C11 C10 H10B . . . 109.3 ? H10A C10 H10B . . . 108 ? C10 O10 C13 . . . 109.28(13) Y O12 C11 C10 . . . 110.58(16) Y O12 C11 H11A . . . 109.5 ? C10 C11 H11A . . . 109.5 ? O12 C11 H11B . . . 109.5 ? C10 C11 H11B . . . 109.5 ? H11A C11 H11B . . . 108.1 ? O12 C12 C13 . . . 110.63(16) Y O12 C12 H12A . . . 109.5 ? C13 C12 H12A . . . 109.5 ? O12 C12 H12B . . . 109.5 ? C13 C12 H12B . . . 109.5 ? H12A C12 H12B . . . 108.1 ? C12 O12 C11 . . . 109.27(14) Y O10 C13 C12 . . . 110.60(16) Y O10 C13 H13A . . . 109.5 ? C12 C13 H13A . . . 109.5 ? O10 C13 H13B . . . 109.5 ? C12 C13 H13B . . . 109.5 ? H13A C13 H13B . . . 108.1 ? C23 O13 C22 . . . 103.6(2) Y C20 O13 C22 . . . 114.9(2) Y C23 O13 C21 . . . 114.6(2) Y C20 O13 C21 . . . 102.9(3) Y C21 C20 O13 2_576 . . 104.0(3) Y C21 C20 H20A 2_576 . . 111 ? O13 C20 H20A . . . 111 ? C21 C20 H20B 2_576 . . 111 ? O13 C20 H20B . . . 111 ? H20A C20 H20B . . . 109 ? C20 C21 O13 2_576 . . 103.6(4) Y C20 C21 H21A 2_576 . . 111 ? O13 C21 H21A . . . 111 ? C20 C21 H21B 2_576 . . 111 ? O13 C21 H21B . . . 111 ? H21A C21 H21B . . . 109 ? O13 C22 C23 . . 2_576 102.9(3) Y O13 C22 H22A . . . 111.2 ? C23 C22 H22A 2_576 . . 111.2 ? O13 C22 H22B . . . 111.2 ? C23 C22 H22B 2_576 . . 111.2 ? H22A C22 H22B . . . 109.1 ? O13 C23 C22 . . 2_576 102.9(3) Y O13 C23 H23A . . . 111.2 ? C22 C23 H23A 2_576 . . 111.2 ? O13 C23 H23B . . . 111.2 ? C22 C23 H23B 2_576 . . 111.2 ? H23A C23 H23B . . . 109.1 ? 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 C7 C2 C3 C4 . . . . -1.2(3) Y C1 C2 C3 C4 . . . . 179.67(16) Y C2 C3 C4 C5 . . . . -0.3(3) Y C3 C4 C5 C6 . . . . 1.2(3) Y C3 C4 C5 B1 . . . . -177.35(16) Y O2 B1 C5 C6 . . . . 18.1(3) Y O1 B1 C5 C6 . . . . -160.2(2) Y O2 B1 C5 C4 . . . . -163.29(18) Y O1 B1 C5 C4 . . . . 18.4(3) Y C4 C5 C6 C7 . . . . -0.7(3) Y B1 C5 C6 C7 . . . . 177.91(16) Y C5 C6 C7 C2 . . . . -0.7(3) Y C3 C2 C7 C6 . . . . 1.7(3) Y C1 C2 C7 C6 . . . . -179.15(15) Y C11 C10 O10 C13 . . . . -56.4(2) Y O10 C10 C11 O12 . . . . 57.5(2) Y C13 C12 O12 C11 . . . . 58.9(2) Y C10 C11 O12 C12 . . . . -57.7(2) Y C10 O10 C13 C12 . . . . 57.1(2) Y O12 C12 C13 O10 . . . . -59.4(2) Y C23 O13 C20 C21 . . . 2_576 -42.8(4) Y C22 O13 C20 C21 . . . 2_576 34.8(5) Y C21 O13 C20 C21 . . . 2_576 72.2(5) Y C23 O13 C21 C20 . . . 2_576 -37.3(5) Y C20 O13 C21 C20 . . . 2_576 -71.9(5) Y C22 O13 C21 C20 . . . 2_576 42.6(4) Y C23 O13 C22 C23 . . . 2_576 73.1(4) Y C20 O13 C22 C23 . . . 2_576 38.3(5) Y C21 O13 C22 C23 . . . 2_576 -39.8(3) Y C20 O13 C23 C22 . . . 2_576 41.2(3) Y C22 O13 C23 C22 . . . 2_576 -73.1(4) Y C21 O13 C23 C22 . . . 2_576 -35.3(5) Y 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 O1 H1 O13 0.91(3) 1.85(3) 2.7206(19) 159(3) . O2 H2 O1 0.94(3) 1.82(3) 2.7458(15) 167(3) 2_666 _refine_diff_density_max 0.348 _refine_diff_density_min -0.547 _refine_diff_density_rms 0.125 data_jiw973 _database_code_depnum_ccdc_archive 'CCDC 283687' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H12 B2 O4' _chemical_formula_sum 'C14 H12 B2 O4' _chemical_formula_weight 265.86 _chemical_compound_source 'Synthesized by the authors. See text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n _symmetry_space_group_name_hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.3430(2) _cell_length_b 5.0685(1) _cell_length_c 11.5810(2) _cell_angle_alpha 90.00 _cell_angle_beta 103.737(1) _cell_angle_gamma 90.00 _cell_volume 646.77(2) _cell_formula_units_Z 2 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 5237 _cell_measurement_theta_min 4.91 _cell_measurement_theta_max 68.82 _exptl_crystal_description block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.365 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 276 _exptl_absorpt_coefficient_mu 0.793 _exptl_absorpt_correction_Type multi-scan _exptl_absorpt_correction_T_min 0.9300 _exptl_absorpt_correction_T_max 0.9600 _exptl_absorpt_process_details 'Sadabs (Sheldrick,1996)' _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator 'Montel 200 optics' _diffrn_measurement_device_type 'Bruker Smart 6000' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 5.5 _diffrn_standards_number 51 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 1.03 _diffrn_reflns_number 8809 _diffrn_reflns_av_R_equivalents 0.026 _diffrn_reflns_av_sigmaI/netI 0.0134 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 4.91 _diffrn_reflns_theta_max 68.81 _reflns_number_total 1179 _reflns_number_gt 1090 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2003)' _computing_cell_refinement 'SMART (Bruker, 2003)' _computing_data_reduction 'SAINT (Bruker, 2004)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 1997)' _computing_publication_material 'UdMX (local program)' _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^)+(0.0747P)^2^+0.0720P] 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 refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0074(16) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1179 _refine_ls_number_parameters 116 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0367 _refine_ls_R_factor_gt 0.0353 _refine_ls_wR_factor_ref 0.1048 _refine_ls_wR_factor_gt 0.1030 _refine_ls_goodness_of_fit_ref 1.088 _refine_ls_restrained_S_all 1.088 _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 B1 B 0.31037(10) 0.5772(2) -0.06722(10) 0.0277(3) Uani 1 1 d . . . O8 O 0.31139(8) 0.81833(15) -0.11796(7) 0.0354(3) Uani 1 1 d . . . H8 H 0.2857(16) 0.819(4) -0.1976(18) 0.067(5) Uiso 1 1 d . . . O9 O 0.26118(7) 0.36813(16) -0.13776(6) 0.0332(3) Uani 1 1 d . . . H9 H 0.2738(16) 0.206(4) -0.1041(16) 0.062(5) Uiso 1 1 d . . . C1 C 0.36175(9) 0.5493(2) 0.07057(9) 0.0267(3) Uani 1 1 d . . . C2 C 0.44272(10) 0.7354(2) 0.13382(9) 0.0304(3) Uani 1 1 d . . . H2 H 0.4705(13) 0.881(3) 0.0899(12) 0.040(3) Uiso 1 1 d . . . C3 C 0.48564(10) 0.7205(2) 0.25596(9) 0.0326(3) Uani 1 1 d . . . H3 H 0.5407(13) 0.854(3) 0.2979(13) 0.042(4) Uiso 1 1 d . . . C4 C 0.44640(10) 0.5174(2) 0.31957(9) 0.0303(3) Uani 1 1 d . . . C5 C 0.36562(11) 0.3293(2) 0.25764(10) 0.0335(3) Uani 1 1 d . . . H5 H 0.3345(13) 0.187(3) 0.2992(13) 0.042(4) Uiso 1 1 d . . . C6 C 0.32513(10) 0.3452(2) 0.13506(9) 0.0310(3) Uani 1 1 d . . . H6 H 0.2695(13) 0.215(3) 0.0944(13) 0.037(3) Uiso 1 1 d . . . C7 C 0.48535(10) 0.5050(2) 0.44690(9) 0.0344(3) Uani 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 B1 0.0319(6) 0.0289(6) 0.0210(6) -0.0009(4) 0.0036(4) 0.0027(4) O8 0.0549(6) 0.0284(5) 0.0188(4) 0.0007(3) 0.0003(3) -0.0027(3) O9 0.0494(5) 0.0272(5) 0.0192(4) -0.0003(3) 0.0006(3) -0.0007(3) C1 0.0317(5) 0.0277(6) 0.0199(5) -0.0002(4) 0.0044(4) 0.0036(4) C2 0.0359(6) 0.0315(6) 0.0226(5) 0.0023(4) 0.0047(4) -0.0014(4) C3 0.0351(6) 0.0361(7) 0.0235(6) -0.0024(4) 0.0006(4) -0.0026(4) C4 0.0353(6) 0.0352(6) 0.0190(6) 0.0008(4) 0.0034(4) 0.0069(4) C5 0.0454(7) 0.0325(6) 0.0225(6) 0.0039(4) 0.0080(5) -0.0006(5) C6 0.0388(6) 0.0302(6) 0.0224(6) -0.0014(4) 0.0038(4) -0.0027(4) C7 0.0397(7) 0.0387(7) 0.0227(5) 0.0011(4) 0.0035(4) 0.0050(5) _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_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag B1 O8 . . 1.3575(15) Y B1 O9 . . 1.3728(14) Y B1 C1 . . 1.5698(14) Y O8 H8 . . 0.90(2) ? O9 H9 . . 0.907(19) ? C1 C6 . . 1.3960(15) Y C1 C2 . . 1.3965(15) Y C2 C3 . . 1.3843(15) Y C2 H2 . . 0.989(14) ? C3 C4 . . 1.3987(16) Y C3 H3 . . 0.970(15) ? C4 C5 . . 1.3968(16) Y C4 C7 . . 1.4368(15) Y C5 C6 . . 1.3867(15) Y C5 H5 . . 0.977(15) ? C6 H6 . . 0.955(15) ? C7 C7 . 3_666 1.196(2) Y 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_2 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O8 B1 O9 . . . 118.78(9) Y O8 B1 C1 . . . 118.79(9) Y O9 B1 C1 . . . 122.4(1) Y B1 O8 H8 . . . 114.4(13) ? B1 O9 H9 . . . 116.3(12) ? C6 C1 C2 . . . 117.53(10) Y C6 C1 B1 . . . 121.65(9) Y C2 C1 B1 . . . 120.78(9) Y C3 C2 C1 . . . 121.81(10) Y C3 C2 H2 . . . 119.2(8) ? C1 C2 H2 . . . 119.0(8) ? C2 C3 C4 . . . 119.97(10) Y C2 C3 H3 . . . 120.1(9) ? C4 C3 H3 . . . 119.9(8) ? C5 C4 C3 . . . 118.95(9) Y C5 C4 C7 . . . 120.1(1) Y C3 C4 C7 . . . 120.93(10) Y C6 C5 C4 . . . 120.23(10) Y C6 C5 H5 . . . 118.5(9) ? C4 C5 H5 . . . 121.3(8) ? C5 C6 C1 . . . 121.5(1) Y C5 C6 H6 . . . 118.9(8) ? C1 C6 H6 . . . 119.6(8) ? C7 C7 C4 3_666 . . 178.27(15) Y 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 O8 B1 C1 C6 . . . . 155.83(11) Y O9 B1 C1 C6 . . . . -22.21(15) Y O8 B1 C1 C2 . . . . -21.67(15) Y O9 B1 C1 C2 . . . . 160.29(10) Y C6 C1 C2 C3 . . . . -0.09(16) Y B1 C1 C2 C3 . . . . 177.50(9) Y C1 C2 C3 C4 . . . . -1.04(17) Y C2 C3 C4 C5 . . . . 1.15(16) Y C2 C3 C4 C7 . . . . -177.1(1) Y C3 C4 C5 C6 . . . . -0.13(16) Y C7 C4 C5 C6 . . . . 178.12(10) Y C4 C5 C6 C1 . . . . -1.03(17) Y C2 C1 C6 C5 . . . . 1.13(16) Y B1 C1 C6 C5 . . . . -176.44(10) Y 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 O8 H8 O9 0.90(2) 1.87(2) 2.7638(10) 172.20(18) 2_554 O9 H9 O8 0.907(19) 2.024(19) 2.8426(11) 149.40(16) 1_545 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 68.81 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.232 _refine_diff_density_min -0.153 _refine_diff_density_rms 0.044