# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 188/233 data_3_4-Dihydroxy_buzaldehyde #------------------------------------------------------------------------------ _audit_creation_date '1999-10-14' _audit_creation_method 'by teXsan v1.8' _audit_update_record ; ? ; #------------------------------------------------------------------------------ _publ_requested_journal ' ENTER JOURNAL NAME HERE' _publ_requested_category ' CHOOSE FI FM FO CI CM CO or AD' _publ_contact_author_name ' ENTER CONTACT NAME HERE' _publ_contact_author_address ; ENTER ADDRESS ; _publ_contact_letter ; ENTER TEXT OF LETTER ; _publ_requested_coeditor_name ? _publ_contact_author_phone ' ENTER PHONE NUMBER ' _publ_contact_author_fax ' ENTER FAX NUMBER ' _publ_contact_author_email ' ENTER EMAIL ADDRESS ' loop_ _publ_author_name _publ_author_footnote _publ_author_address ' FIRST AUTHORS NAME ' ; FIRST AUTHORS FOOTNOTES ; ; FIRST AUTHORS ADDRESS ; _publ_section_title ; ENTER SECTION TITLE ; _publ_section_title_footnote ' ENTER ANY FOOTNOTES TO TITLE ' _publ_section_abstract ; ENTER ABSTRACT ; _publ_section_exptl_refinement ; ENTER EXPERIMENTAL SECTION ; _publ_section_comment ; ENTER TEXT ; _publ_section_references ; ENTER OTHER REFERENCES Molecular Structure Corporation. (1992-1997). teXsan. Single Crystal Structure Analysis Software. Version 1.7. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. Zachariasen, W. H. (1967). Acta Cryst. 23, 558-564. Altomare, A., Cascarano, M., Giacovazzo, C., Guagliardi, A. (1993). J. Appl. Cryst., 26, 343. ; _publ_section_acknowledgements ; ENTER ACKNOWLEDGEMENTS ; _publ_section_table_legends ; ENTER TABLE LEGENDS ; _publ_section_figure_captions ; ENTER FIGURE CAPTIONS ; #------------------------------------------------------------------------------ loop_ _publ_manuscript_incl_extra_item '_geom_extra_table_head_3' '_geom_bond_atom_site_label_D' '_geom_bond_atom_site_label_H' '_geom_contact_atom_site_label_A' '_geom_bond_distance_DH' '_geom_contact_distance_HA' '_geom_contact_distance_DA' '_geom_angle_DHA' '_geom_contact_site_symmetry_A' # # #------------------------------------------------------------------------------ _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan (MSC, 1992-1997)' _computing_structure_solution ; SIR92 (Altomare, et. al. 1993) ; _computing_structure_refinement 'teXsan (MSC, 1992-1997)' _computing_publication_material 'teXsan (MSC, 1992-1997)' #------------------------------------------------------------------------------ _cell_length_a 3.780(1) _cell_length_b 7.621(1) _cell_length_c 10.581(2) _cell_angle_alpha 90.00(1) _cell_angle_beta 90.20(1) _cell_angle_gamma 90.00(1) _cell_volume 304.81(9) _cell_formula_units_Z 2 _cell_measurement_temperature 273.2 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0.0 _cell_measurement_theta_max 0.0 #------------------------------------------------------------------------------ _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21 ' _symmetry_Int_Tables_number 4 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' ' -x,1/2+y, -z' #------------------------------------------------------------------------------ _publ_section_exptl_prep ; ENTER EXPERIMENTAL SECTION ; _exptl_crystal_description 'irregular' _exptl_crystal_colour 'clear' _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.06 _exptl_crystal_density_diffrn 1.505 _exptl_crystal_density_meas 'not measured' _chemical_formula_weight 138.12 _chemical_formula_analytical ? _chemical_formula_sum 'C7 H6 O3 ' _chemical_formula_moiety 'C7 H6 O3 ' _chemical_formula_structural ? _chemical_compound_source ? _exptl_crystal_F_000 144.00 _exptl_absorpt_coefficient_mu 0.119 _exptl_absorpt_correction_type none _exptl_special_details ; ? ; #------------------------------------------------------------------------------ _diffrn_special_details ; ? ; _diffrn_ambient_temperature 273.2 _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'CCD' _diffrn_measurement_device_type 'Quantum CCD' _diffrn_detector_area_resol_mean ? _diffrn_measurement_method ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_decay_% 0.00 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? _diffrn_reflns_number 1939 _reflns_number_total 772 _reflns_number_gt 654 _reflns_threshold_expression I>3.00\s(I) _diffrn_reflns_av_R_equivalents 0.04429 _diffrn_reflns_av_sigmaI/netI 0.020 _diffrn_reflns_theta_full ? _diffrn_measured_fraction_theta_max ? _diffrn_measured_fraction_theta_full ? _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 28.25 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_orient_matrix_UB_11 0.00000 _diffrn_orient_matrix_UB_12 0.00000 _diffrn_orient_matrix_UB_13 0.00000 _diffrn_orient_matrix_UB_21 0.00000 _diffrn_orient_matrix_UB_22 0.00000 _diffrn_orient_matrix_UB_23 0.00000 _diffrn_orient_matrix_UB_31 0.00000 _diffrn_orient_matrix_UB_32 0.00000 _diffrn_orient_matrix_UB_33 0.00000 #------------------------------------------------------------------------------ loop_ _atom_type_symbol _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O 0 6 0.008 0.006 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; C 0 14 0.002 0.002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; H 0 12 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; #------------------------------------------------------------------------------ loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_refinement_flags _atom_site_adp_type _atom_site_calc_flag _atom_site_calc_attached_atom O(3) 0.3848(3) 0.2285(2) 0.42825(9) 0.0317(3) 1.000 D Uani d ? O(4) 0.5477(3) 0.1226(2) 0.19561(9) 0.0305(3) 1.000 D Uani d ? O(11) -0.1716(3) 0.8576(2) 0.34433(8) 0.0293(3) 1.000 . Uani d ? C(1) 0.1024(3) 0.6132(3) 0.2411(1) 0.0213(3) 1.000 . Uani d ? C(2) 0.1597(3) 0.5060(3) 0.3473(1) 0.0220(3) 1.000 D Uani d ? C(3) 0.3095(3) 0.3431(3) 0.3329(1) 0.0218(3) 1.000 . Uani d ? C(4) 0.4023(4) 0.2824(3) 0.2109(1) 0.0228(3) 1.000 . Uani d ? C(5) 0.3426(3) 0.3875(3) 0.1064(1) 0.0249(4) 1.000 D Uani d ? C(6) 0.1958(3) 0.5526(3) 0.1206(1) 0.0239(3) 1.000 D Uani d ? C(11) -0.0503(3) 0.7869(3) 0.2499(1) 0.0231(3) 1.000 D Uani d ? H(2) 0.0848 0.5607 0.4242 0.025 1.000 D Uiso c ? H(3) 0.2957 0.2672 0.4969 0.076 1.000 D Uiso c ? H(4) 0.5966 0.0801 0.2680 0.031 1.000 D Uiso c ? H(5) 0.3980 0.3423 0.0252 0.041 1.000 D Uiso c ? H(6) 0.1327 0.6204 0.0479 0.027 1.000 D Uiso c ? H(11) -0.0506 0.8385 0.1676 0.024 1.000 D Uiso c ? 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 O(3) 0.0489(6) 0.0249(6) 0.0212(5) 0.0079(5) 0.0027(4) 0.0050(5) O(4) 0.0434(6) 0.0232(6) 0.0249(5) 0.0101(5) 0.0003(4) -0.0007(6) O(11) 0.0373(5) 0.0252(6) 0.0254(5) 0.0031(5) 0.0026(4) -0.0022(6) C(1) 0.0191(6) 0.0222(7) 0.0226(6) -0.0004(6) -0.0003(5) -0.0001(6) C(2) 0.0249(7) 0.0217(8) 0.0195(6) -0.0010(6) 0.0015(5) 0.0005(6) C(3) 0.0218(6) 0.0232(7) 0.0205(6) 0.0003(6) 0.0002(5) 0.0024(6) C(4) 0.0250(6) 0.0192(8) 0.0242(6) 0.0011(6) -0.0003(5) -0.0034(6) C(5) 0.0278(7) 0.0277(9) 0.0191(6) 0.0017(6) 0.0020(5) -0.0033(7) C(6) 0.0236(6) 0.0285(8) 0.0197(6) 0.0012(6) -0.0007(5) 0.0024(7) C(11) 0.0242(7) 0.0214(8) 0.0237(6) 0.0000(6) 0.0000(5) 0.0022(6) #------------------------------------------------------------------------------ _refine_special_details ; ? ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme 'w = 1/[\s^2^(Fo)]' _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method 'Zachariasen (1967)' _refine_ls_extinction_coef 0.0000184(3) _refine_ls_extinction_expression 'equ(3) Acta Cryst.(1968) A24, p213.' _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 654 _refine_ls_number_parameters 92 _refine_ls_number_restraints 6 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.0399 _refine_ls_R_factor_gt 0.0399 _refine_ls_wR_factor_all 0.0307 _refine_ls_wR_factor_ref 0.0307 _refine_ls_goodness_of_fit_all 2.777 _refine_ls_goodness_of_fit_ref 2.777 _refine_ls_shift/esd_max 0.3911 _refine_ls_shift/esd_mean 0.0000 _refine_diff_density_min -0.51 _refine_diff_density_max 0.42 #------------------------------------------------------------------------------ _geom_special_details ; ? ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O(3) C(3) 1.364(3) . . yes O(3) H(3) 0.85 . . no O(4) C(4) 1.346(3) . . yes O(4) H(4) 0.85 . . no O(11) C(11) 1.225(3) . . yes C(1) C(2) 1.406(3) . . yes C(1) C(6) 1.402(3) . . yes C(1) C(11) 1.448(3) . . yes C(2) C(3) 1.373(4) . . yes C(2) H(2) 0.96 . . no C(3) C(4) 1.416(3) . . yes C(4) C(5) 1.384(3) . . yes C(5) C(6) 1.384(4) . . yes C(5) H(5) 0.95 . . no C(6) H(6) 0.96 . . no C(11) H(11) 0.96 . . no #------------------------------------------------------------------------------ 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C(3) O(3) H(3) 109.0 . . . no C(4) O(4) H(4) 108.9 . . . no C(2) C(1) C(6) 119.8(2) . . . yes C(2) C(1) C(11) 122.7(2) . . . yes C(6) C(1) C(11) 117.5(2) . . . yes C(1) C(2) C(3) 119.9(2) . . . yes C(1) C(2) H(2) 112.4 . . . no C(3) C(2) H(2) 127.7 . . . no O(3) C(3) C(2) 125.6(2) . . . yes O(3) C(3) C(4) 114.4(2) . . . yes C(2) C(3) C(4) 120.1(2) . . . yes O(4) C(4) C(3) 120.5(2) . . . yes O(4) C(4) C(5) 119.6(2) . . . yes C(3) C(4) C(5) 119.9(2) . . . yes C(4) C(5) C(6) 120.3(2) . . . yes C(4) C(5) H(5) 118.5 . . . no C(6) C(5) H(5) 121.2 . . . no C(1) C(6) C(5) 120.0(2) . . . yes C(1) C(6) H(6) 119.4 . . . no C(5) C(6) H(6) 120.2 . . . no O(11) C(11) C(1) 127.2(2) . . . yes O(11) C(11) H(11) 124.3 . . . no C(1) C(11) H(11) 108.4 . . . no #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O(3) O(11) 2.724(2) . 2_546 no O(3) C(2) 3.384(3) . 2_646 no O(3) O(11) 3.406(3) . 1_645 no O(3) C(2) 3.576(3) . 2_546 no O(4) O(11) 2.769(2) . 1_645 no O(4) C(11) 3.029(3) . 1_645 no O(4) C(4) 3.455(3) . 1_655 no O(4) C(11) 3.463(3) . 1_545 no O(4) C(6) 3.527(3) . 2_645 no O(11) C(2) 3.453(3) . 2_556 no O(11) C(3) 3.459(3) . 2_556 no O(11) C(1) 3.489(3) . 1_455 no O(11) C(11) 3.507(3) . 1_455 no C(1) C(11) 3.467(3) . 1_655 no C(2) C(3) 3.448(3) . 1_455 no C(5) C(6) 3.465(3) . 1_655 no #------------------------------------------------------------------------------ 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 O(3) C(3) C(2) C(1) . . . . 178.7(2) no O(3) C(3) C(4) O(4) . . . . 0.8(3) no O(3) C(3) C(4) C(5) . . . . -179.3(2) no O(4) C(4) C(3) C(2) . . . . -179.7(2) no O(4) C(4) C(5) C(6) . . . . -179.5(2) no O(11) C(11) C(1) C(2) . . . . -5.9(4) no O(11) C(11) C(1) C(6) . . . . 174.3(2) no C(1) C(2) C(3) C(4) . . . . -0.8(3) no C(1) C(6) C(5) C(4) . . . . -0.9(3) no C(2) C(1) C(6) C(5) . . . . 0.2(3) no C(2) C(3) C(4) C(5) . . . . 0.2(3) no C(3) C(2) C(1) C(6) . . . . 0.6(3) no C(3) C(2) C(1) C(11) . . . . -179.2(2) no C(3) C(4) C(5) C(6) . . . . 0.7(3) no C(5) C(6) C(1) C(11) . . . . -180.0(2) no #------------------------------------------------------------------------------ loop_ _geom_bond_atom_site_label_D _geom_bond_atom_site_label_H _geom_contact_atom_site_label_A _geom_bond_distance_DH _geom_contact_distance_HA _geom_contact_distance_DA _geom_angle_DHA _geom_contact_site_symmetry_A 'O(3)' 'H(3)' 'O(11)' '0.85' '1.88' '2.724(2)' '171.2' '2_546' 'O(4)' 'H(4)' 'O(11)' '0.85' '2.07' '2.769(2)' '138.8' '1_645' 'O(4)' 'H(4)' 'O(3)' '0.85' '2.19' '2.665(2)' '114.9' '.'