#------------------------------------------------------------------------------ #$Date: 2012-02-03 17:16:24 +0000 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/90/2009020.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2009020 loop_ _publ_author_name 'Robinson, Paul D.' 'Groziak, Michael P.' _publ_section_title ; A boron-containing estrogen mimic ; _journal_issue 10 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1701 _journal_page_last 1704 _journal_volume 55 _journal_year 1999 _chemical_formula_moiety 'C13 H12 B N3 O3, H2 O' _chemical_formula_sum 'C13 H14 B N3 O4' _chemical_formula_weight 287.08 _chemical_name_systematic ; 1,2-Dihydro-1,6-dihydroxy-2-(2-methoxy-6-pyridyl)-2,3,1-benzodiazaborine ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _cell_angle_alpha 111.952(11) _cell_angle_beta 98.61(3) _cell_angle_gamma 103.04(3) _cell_formula_units_Z 2 _cell_length_a 8.885(3) _cell_length_b 10.2996(19) _cell_length_c 8.5543(15) _cell_measurement_reflns_used 23 _cell_measurement_temperature 296 _cell_measurement_theta_max 14.8 _cell_measurement_theta_min 6.3 _cell_volume 683.2(3) _computing_cell_refinement 'MSC/AFC Diffractometer Control Software' _computing_data_collection ; MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1996) ; _computing_data_reduction ; PROCESS in TEXSAN (Molecular Structure Corporation, 1997) ; _computing_molecular_graphics 'ORTEP (Johnson, 1965) in TEXSAN' _computing_publication_material ; TEXSAN, SHELXL97 and PLATON (Spek, 1990) ; _computing_structure_refinement 'LS in TEXSAN and SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 296 _diffrn_measurement_device_type 'Rigaku AFC-5S diffractometer' _diffrn_measurement_method '\w (rate 4\% min^-1^ in \w)' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71069 _diffrn_reflns_av_R_equivalents 0.008 _diffrn_reflns_av_sigmaI/netI 0.0216 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 2585 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 2.24 _diffrn_standards_decay_% 0.40 _diffrn_standards_interval_count 150 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_type none _exptl_crystal_colour 'pale brown' _exptl_crystal_density_diffrn 1.396 _exptl_crystal_density_meas 'not measured' _exptl_crystal_description 'irregular fragment' _exptl_crystal_F_000 300 _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.24 _refine_diff_density_max 0.144 _refine_diff_density_min -0.144 _refine_ls_extinction_coef 0.009(3) _refine_ls_extinction_method 'SHELXL97 (Sheldrick, 1997)' _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 206 _refine_ls_number_reflns 2416 _refine_ls_number_restraints 4 _refine_ls_restrained_S_all 1.029 _refine_ls_R_factor_all 0.067 _refine_ls_R_factor_gt 0.036 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0640P)^2^+0.0583P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.118 _reflns_number_gt 1582 _reflns_number_total 2416 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file fg1557.cif _[local]_cod_data_source_block default _cod_database_code 2009020 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' loop_ _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 _atom_site_type_symbol O1 .74521(17) .66309(14) -.09367(16) .0621(4) Uani d . 1 . . O B1 .7605(2) .5404(2) -.0755(2) .0476(5) Uani d . 1 . . B N2 .72545(16) .51123(14) .07114(17) .0475(4) Uani d . 1 . . N N3 .74239(18) .38762(16) .09353(18) .0554(4) Uani d . 1 . . N C4 .7923(2) .29686(19) -.0204(2) .0538(5) Uani d . 1 . . C C4a .83296(19) .30593(18) -.1747(2) .0465(4) Uani d . 1 . . C C5 .8859(2) .19768(19) -.2879(2) .0517(4) Uani d . 1 . . C C6 .9211(2) .21005(19) -.4341(2) .0516(4) Uani d . 1 . . C O6 .97582(18) .10754(15) -.54486(18) .0642(4) Uani d D 1 . . O C7 .9009(2) .32667(19) -.4712(2) .0573(5) Uani d . 1 . . C C8 .8508(2) .43286(19) -.3586(2) .0554(5) Uani d . 1 . . C C8a .81630(19) .42612(17) -.2070(2) .0467(4) Uani d . 1 . . C C9 .67492(19) .60424(19) .2093(2) .0481(4) Uani d . 1 . . C C10 .6495(2) .5742(2) .3494(2) .0582(5) Uani d . 1 . . C C11 .6032(2) .6753(2) .4779(3) .0663(5) Uani d . 1 . . C C12 .5823(2) .7986(2) .4652(3) .0656(5) Uani d . 1 . . C C13 .6093(2) .8179(2) .3189(2) .0559(5) Uani d . 1 . . C O13 .58729(17) .93918(15) .30460(17) .0706(4) Uani d . 1 . . O C14 .6203(3) .9634(2) .1584(3) .0799(6) Uani d . 1 . . C N14 .65527(17) .72507(16) .19423(18) .0511(4) Uani d . 1 . . N O15 .9529(3) .8790(2) -.1581(3) .0990(6) Uani d D 1 . . O H1 .7073 .7088 -.0170 .093 Uiso calc R 1 . . H H4 .8036 .2159 -.0015 .065 Uiso calc R 1 . . H H5 .8971 .1186 -.2646 .062 Uiso calc R 1 . . H H6a .992(6) .054(5) -.497(6) .096 Uiso d PD .52(3) A 1 H H6b 1.001(6) .126(5) -.628(5) .096 Uiso d PD .48(3) A 2 H H7 .9212 .3325 -.5723 .069 Uiso calc R 1 . . H H8 .8396 .5112 -.3835 .066 Uiso calc R 1 . . H H10 .6627 .4897 .3575 .070 Uiso calc R 1 . . H H11 .5862 .6585 .5743 .080 Uiso calc R 1 . . H H12 .5514 .8664 .5509 .079 Uiso calc R 1 . . H H14a .7293 .9680 .1574 .120 Uiso calc R 1 . . H H14b .6040 1.0544 .1662 .120 Uiso calc R 1 . . H H14c .5500 .8840 .0530 .120 Uiso calc R 1 . . H H15a .891(3) .811(3) -.151(4) .148 Uiso d D 1 . . H H15b .885(3) .915(4) -.141(5) .148 Uiso d D 1 . . H 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 O1 .0918(10) .0547(7) .0581(8) .0331(7) .0333(7) .0318(6) B1 .0501(11) .0451(11) .0474(10) .0097(9) .0089(9) .0236(9) N2 .0531(9) .0473(8) .0454(7) .0163(6) .0147(6) .0218(6) N3 .0708(10) .0558(9) .0536(8) .0250(8) .0225(8) .0323(7) C4 .0679(12) .0518(10) .0523(10) .0230(9) .0200(9) .0289(9) C4a .0483(10) .0461(9) .0442(9) .0114(8) .0099(7) .0207(7) C5 .0600(11) .0484(10) .0520(9) .0190(8) .0174(8) .0245(8) O6 .0909(10) .0612(8) .0571(8) .0366(7) .0362(7) .0286(6) C6 .0569(11) .0490(10) .0477(9) .0157(8) .0160(8) .0186(8) C7 .0749(12) .0554(11) .0480(9) .0203(9) .0238(9) .0254(9) C8 .0722(12) .0498(10) .0516(10) .0200(9) .0193(9) .0273(8) C8a .0495(10) .0448(9) .0436(9) .0096(7) .0088(7) .0205(7) C9 .0424(9) .0524(10) .0470(9) .0118(7) .0098(7) .0208(8) C10 .0631(12) .0661(12) .0553(10) .0229(9) .0227(9) .0319(9) C11 .0694(13) .0816(14) .0558(11) .0245(11) .0283(9) .0322(10) C12 .0692(13) .0714(13) .0596(11) .0288(10) .0299(10) .0224(10) C13 .0506(10) .0581(11) .0571(11) .0199(9) .0144(8) .0201(9) O13 .0857(10) .0680(9) .0713(9) .0398(7) .0304(7) .0303(7) C14 .1071(18) .0718(14) .0751(13) .0415(13) .0240(13) .0382(12) N14 .0503(8) .0535(8) .0488(8) .0173(7) .0130(6) .0200(7) O15 .1260(16) .0745(11) .0908(11) .0074(10) .0339(11) .0402(10) 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 B1 O1 . 1.363(2) yes C6 O6 . 1.368(2) yes O13 C13 . 1.353(2) no O13 C14 . 1.422(2) no N2 N3 . 1.3930(19) yes N2 C9 . 1.422(2) yes B1 N2 . 1.455(2) yes N3 C4 . 1.287(2) yes N14 C13 . 1.328(2) no N14 C9 . 1.344(2) no C4a C8a . 1.399(2) yes C4a C5 . 1.403(2) no C5 C6 . 1.377(2) no C4 C4a . 1.449(2) yes C6 C7 . 1.394(2) no C7 C8 . 1.372(2) no C8 C8a . 1.398(2) no C8a B1 . 1.529(3) yes C9 C10 . 1.382(2) no C10 C11 . 1.390(3) no C11 C12 . 1.364(3) no C12 C13 . 1.386(3) no C4 H4 . .9300 no C5 H5 . .9300 no C7 H7 . .9300 no C8 H8 . .9300 no C10 H10 . .9300 no C11 H11 . .9300 no C12 H12 . .9300 no C14 H14a . .9600 no C14 H14b . .9600 no C14 H14c . .9600 no 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' O O 0.0106 0.0060 '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' loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 0 -1 1 2 -1 1 0 1 2 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C13 O13 C14 117.84(15) no N3 N2 C9 111.99(13) yes N3 N2 B1 122.73(14) yes C9 N2 B1 125.26(14) yes C4 N3 N2 118.01(13) yes C13 N14 C9 118.30(15) no N3 C4 C4a 127.65(15) yes C8a C4a C5 121.27(15) no C8a C4a C4 117.49(15) yes C5 C4a C4 121.23(15) no C6 C5 C4a 119.13(16) no O6 C6 C5 120.31(15) no O6 C6 C7 119.25(15) no C5 C6 C7 120.44(16) no C8 C7 C6 119.93(16) no C7 C8 C8a 121.56(16) no C8 C8a C4a 117.62(15) no C8 C8a B1 124.45(14) yes C4a C8a B1 117.93(14) yes N14 C9 C10 122.36(16) no N14 C9 N2 114.73(14) no C10 C9 N2 122.91(16) no C9 C10 C11 117.40(18) no C12 C11 C10 121.28(18) no N14 C13 O13 119.02(16) no N14 C13 C12 123.76(18) no O13 C13 C12 117.23(16) no C11 C12 C13 116.90(17) no O1 B1 N2 121.79(16) yes C8a B1 O1 122.04(15) yes N2 B1 C8a 116.17(14) yes C6 O6 H6A 106(4) no C6 O6 H6B 115(3) no H6A O6 H6B 138(5) no H15A O15 H15B 83(3) no B1 O1 H1 109.5 no N3 C4 H4 116.2 no C4a C4 H4 116.2 no C6 C5 H5 120.4 no C4a C5 H5 120.4 no C8 C7 H7 120.0 no C6 C7 H7 120.0 no C7 C8 H8 119.2 no C8a C8 H8 119.2 no C9 C10 H10 121.3 no C11 C10 H10 121.3 no C12 C11 H11 119.4 no C10 C11 H11 119.4 no C11 C12 H12 121.6 no C13 C12 H12 121.6 no O13 C14 H14A 109.5 no O13 C14 H14B 109.5 no H14A C14 H14B 109.5 no O13 C14 H14C 109.5 no H14A C14 H14C 109.5 no H14B C14 H14C 109.5 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag O1 H1 N14 . 0.82 1.89 2.599(2) 144 yes O6 H6A O6 2_754 0.82(2) 1.90(5) 2.699(2) 163(5) yes O6 H6B O15 2_764 0.84(2) 1.92(4) 2.754(3) 167(5) yes O15 H15A O1 . 0.82(3) 2.02(3) 2.833(3) 171(3) yes O15 H15B O15 2_775 0.78(3) 2.57(4) 2.751(3) 95(3) yes 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_publ_flag C9 N2 N3 C4 -177.96(15) yes B1 N2 N3 C4 0.5(2) yes N2 N3 C4 C4a -0.7(3) yes N3 C4 C4a C8a -0.4(3) yes N3 C4 C4a C5 -179.89(18) no C8a C4a C5 C6 -0.4(3) no C4 C4a C5 C6 179.16(16) no C4a C5 C6 O6 178.78(16) no C4a C5 C6 C7 -1.5(3) no O6 C6 C7 C8 -177.99(17) no C5 C6 C7 C8 2.3(3) no C6 C7 C8 C8a -1.2(3) no C7 C8 C8a C4a -0.6(3) no C7 C8 C8a B1 179.85(17) no C5 C4a C8a C8 1.4(2) no C4 C4a C8a C8 -178.11(15) no C5 C4a C8a B1 -179.04(16) no C4 C4a C8a B1 1.4(2) yes C13 N14 C9 C10 -0.2(2) no C13 N14 C9 N2 -179.52(15) no N3 N2 C9 N14 -179.52(13) yes B1 N2 C9 N14 2.1(2) yes N3 N2 C9 C10 1.1(2) no B1 N2 C9 C10 -177.28(16) no N14 C9 C10 C11 -0.5(3) no N2 C9 C10 C11 178.76(16) no C9 C10 C11 C12 0.6(3) no C10 C11 C12 C13 0.0(3) no C9 N14 C13 O13 -179.26(15) no C9 N14 C13 C12 0.9(3) no C14 O13 C13 N14 -2.2(3) yes C14 O13 C13 C12 177.69(18) no C11 C12 C13 N14 -0.8(3) no C11 C12 C13 O13 179.36(17) no N3 N2 B1 O1 -179.08(15) no O1 B1 N2 C9 -0.8(3) yes N3 N2 B1 C8a 0.5(2) no C9 N2 B1 C8a 178.81(14) no C8 C8a B1 O1 -2.4(3) yes C4a C8a B1 O1 178.11(16) yes C8 C8a B1 N2 177.99(15) yes C4a C8a B1 N2 -1.5(2) yes