# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 182 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name _publ_author_footnote _publ_author_address 'Kotaro Fujii' ; ? ; ; ? ; 'Yasunari Ashida' '' '' 'Hidehiro Uekusa' '' '' 'Fang Guo.' '' '' 'Kenneth Harris' '' '' _publ_contact_author_name 'Kenneth Harris' _publ_contact_author_email HarrisKDM@cardiff.ac.uk _publ_section_title ; Selective transformation pathways between crystalline forms of an organic material established from powder X-ray diffraction analysis ; _journal_coden_ASTM ? _journal_coeditor_code ? _journal_coeditor_name ? _journal_coeditor_notes ; ? ; #============================================================================== # 2. PROCESSING SUMMARY (IUCr Office Use Only) _journal_data_validation_number ? _journal_date_accepted ? _journal_date_from_coeditor ? _journal_date_printers_final ? _journal_date_printers_first ? _journal_date_proofs_in ? _journal_date_proofs_out ? _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_issue ? _journal_name_full ? _journal_page_last ? _journal_paper_category ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? _journal_techeditor_code ? _journal_techeditor_notes ; ? ; _publ_contact_author_address # Address of author for correspondence ; ? ; _publ_contact_author_fax ? _publ_contact_author_phone ? _publ_contact_letter ; ? ; _publ_requested_category ? # Acta C: one of CI/CM/CO/FI/FM/FO _publ_requested_coeditor_name ? _publ_requested_journal ? # Attachment 'PA-MeOH.cif.txt' data_pam _database_code_depnum_ccdc_archive 'CCDC 768534' #TrackingRef 'PA-MeOH.cif.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H6 O8 . 2(C H4 O)' _chemical_formula_sum 'C12 H14 O10' _chemical_formula_weight 318.23 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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_int_tables_number 2 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 3.8860(3) _cell_length_b 11.0240(9) _cell_length_c 15.9140(13) _cell_angle_alpha 89.827(2) _cell_angle_beta 88.318(2) _cell_angle_gamma 89.997(2) _cell_volume 681.45(9) _cell_formula_units_Z 2 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 9230 _cell_measurement_theta_min 1.28 _cell_measurement_theta_max 27.53 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.551 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 332 _exptl_absorpt_coefficient_mu 0.138 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.808366 _exptl_absorpt_correction_T_max 1.0 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71075 _diffrn_source 'rotating anode X-ray tube' _diffrn_source_type 'Rigaku Ultrax18' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD area detector system' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9230 _diffrn_reflns_av_R_equivalents 0.0258 _diffrn_reflns_av_sigmaI/netI 0.0246 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.28 _diffrn_reflns_theta_max 27.53 _reflns_number_total 3119 _reflns_number_gt 2918 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement SAINT _computing_data_reduction SAINT _computing_structure_solution 'SIR2004(Burla et al.,2004)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0190P)^2^+0.9256P] 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 3119 _refine_ls_number_parameters 209 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0479 _refine_ls_R_factor_gt 0.0453 _refine_ls_wR_factor_ref 0.1069 _refine_ls_wR_factor_gt 0.1056 _refine_ls_goodness_of_fit_ref 1.185 _refine_ls_restrained_S_all 1.185 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O8 O 0.9118(3) -0.71668(12) 0.67701(8) 0.0154(3) Uani 1 1 d . . . O5 O 0.5053(3) -0.50735(12) 0.69877(8) 0.0155(3) Uani 1 1 d . . . H5 H 0.4388 -0.4809 0.7460 0.023 Uiso 1 1 calc R . . O7 O 0.5796(3) -0.77523(11) 0.57091(8) 0.0153(3) Uani 1 1 d . . . H7 H 0.5322 -0.8338 0.6031 0.023 Uiso 1 1 calc R . . O6 O 0.8419(4) -0.34201(12) 0.69904(8) 0.0174(3) Uani 1 1 d . . . O4 O 0.5912(3) -0.19324(12) 0.81485(8) 0.0158(3) Uani 1 1 d . . . H4 H 0.6644 -0.2527 0.7867 0.024 Uiso 1 1 calc R . . O1 O 0.9949(3) 0.01659(12) 0.79802(8) 0.0154(3) Uani 1 1 d . . . O2 O 0.6537(4) 0.18024(11) 0.81292(8) 0.0168(3) Uani 1 1 d . . . H2 H 0.7449 0.2001 0.7664 0.025 Uiso 1 1 calc R . . O10 O 0.2829(4) -0.46360(12) 0.84768(9) 0.0196(3) Uani 1 1 d . . . O3 O 0.9316(4) -0.26959(11) 0.91373(8) 0.0161(3) Uani 1 1 d . . . O9 O 0.3430(4) 0.03824(12) 0.64570(10) 0.0253(3) Uani 1 1 d . . . C5 C 0.7365(4) -0.19247(15) 0.88808(10) 0.0105(3) Uani 1 1 d . . . C2 C 0.6222(4) -0.08902(15) 0.94384(10) 0.0092(3) Uani 1 1 d . . . C6 C 0.8801(4) -0.47424(15) 0.58202(10) 0.0095(3) Uani 1 1 d . . . C3 C 0.4996(4) -0.12082(15) 1.02385(10) 0.0094(3) Uani 1 1 d . . . H3 H 0.4999 -0.2037 1.0404 0.011 Uiso 1 1 calc R . . C1 C 0.6240(4) 0.03336(15) 0.91959(10) 0.0091(3) Uani 1 1 d . . . C7 C 0.8837(4) -0.59410(15) 0.55316(10) 0.0095(3) Uani 1 1 d . . . C8 C 1.0025(4) -0.61828(15) 0.47143(10) 0.0102(3) Uani 1 1 d . . . H8 H 1.0034 -0.6995 0.4517 0.012 Uiso 1 1 calc R . . C9 C 0.7411(4) -0.43588(15) 0.66680(10) 0.0104(3) Uani 1 1 d . . . C10 C 0.7895(4) -0.70112(15) 0.60791(10) 0.0107(3) Uani 1 1 d . . . C4 C 0.7767(4) 0.07441(15) 0.83668(10) 0.0100(3) Uani 1 1 d . . . C11 C 0.4735(6) -0.07847(18) 0.62573(14) 0.0257(4) Uani 1 1 d . . . H11A H 0.6799 -0.0940 0.6580 0.039 Uiso 1 1 calc R . . H11B H 0.5324 -0.0823 0.5655 0.039 Uiso 1 1 calc R . . H11C H 0.2984 -0.1398 0.6399 0.039 Uiso 1 1 calc R . . C12 C 0.1295(6) -0.56800(19) 0.88609(15) 0.0261(5) Uani 1 1 d . . . H12A H 0.1940 -0.5724 0.9451 0.039 Uiso 1 1 calc R . . H12B H 0.2104 -0.6410 0.8566 0.039 Uiso 1 1 calc R . . H12C H -0.1215 -0.5625 0.8831 0.039 Uiso 1 1 calc R . . H9 H 0.218(8) 0.037(3) 0.692(2) 0.045(8) Uiso 1 1 d . . . H10 H 0.160(9) -0.399(3) 0.865(2) 0.056(10) 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 O8 0.0215(7) 0.0144(6) 0.0101(6) 0.0054(5) 0.0002(5) -0.0016(5) O5 0.0189(7) 0.0167(6) 0.0106(6) -0.0011(5) 0.0068(5) -0.0021(5) O7 0.0227(7) 0.0097(6) 0.0135(6) 0.0026(5) 0.0002(5) -0.0050(5) O6 0.0259(7) 0.0140(6) 0.0121(6) -0.0050(5) 0.0045(5) -0.0018(5) O4 0.0234(7) 0.0143(6) 0.0096(6) -0.0051(5) -0.0001(5) 0.0036(5) O1 0.0170(6) 0.0170(6) 0.0116(6) 0.0016(5) 0.0060(5) 0.0028(5) O2 0.0287(7) 0.0115(6) 0.0097(6) 0.0051(5) 0.0079(5) 0.0038(5) O10 0.0303(8) 0.0122(6) 0.0159(7) 0.0010(5) 0.0093(6) 0.0047(5) O3 0.0222(7) 0.0113(6) 0.0146(6) -0.0021(5) 0.0015(5) 0.0052(5) O9 0.0428(9) 0.0112(6) 0.0209(7) 0.0002(5) 0.0169(7) -0.0020(6) C5 0.0141(8) 0.0078(7) 0.0093(7) -0.0001(6) 0.0044(6) -0.0014(6) C2 0.0113(8) 0.0086(7) 0.0076(7) -0.0015(6) 0.0002(6) 0.0011(6) C6 0.0118(8) 0.0104(8) 0.0062(7) 0.0002(6) 0.0004(6) 0.0010(6) C3 0.0126(8) 0.0074(7) 0.0083(7) 0.0014(6) 0.0005(6) 0.0002(6) C1 0.0106(8) 0.0098(8) 0.0069(7) 0.0001(6) 0.0004(6) 0.0001(6) C7 0.0113(8) 0.0097(7) 0.0074(7) 0.0009(6) 0.0007(6) 0.0000(6) C8 0.0132(8) 0.0080(7) 0.0092(8) -0.0003(6) 0.0015(6) 0.0006(6) C9 0.0143(8) 0.0098(7) 0.0069(7) 0.0008(6) 0.0011(6) 0.0037(6) C10 0.0127(8) 0.0093(7) 0.0097(7) 0.0002(6) 0.0044(6) 0.0023(6) C4 0.0139(8) 0.0086(7) 0.0075(7) -0.0003(6) 0.0005(6) -0.0017(6) C11 0.0365(12) 0.0147(9) 0.0255(10) -0.0046(8) 0.0052(9) 0.0003(8) C12 0.0282(11) 0.0175(10) 0.0320(11) 0.0075(8) 0.0116(9) 0.0038(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O8 C10 1.222(2) . ? O5 C9 1.300(2) . ? O5 H5 0.8400 . ? O7 C10 1.308(2) . ? O7 H7 0.8400 . ? O6 C9 1.226(2) . ? O4 C5 1.310(2) . ? O4 H4 0.8400 . ? O1 C4 1.215(2) . ? O2 C4 1.319(2) . ? O2 H2 0.8400 . ? O10 C12 1.424(2) . ? O10 H10 0.90(4) . ? O3 C5 1.217(2) . ? O9 C11 1.416(2) . ? O9 H9 0.88(3) . ? C5 C2 1.506(2) . ? C2 C3 1.390(2) . ? C2 C1 1.402(2) . ? C6 C8 1.394(2) 2_746 ? C6 C7 1.400(2) . ? C6 C9 1.500(2) . ? C3 C1 1.396(2) 2_657 ? C3 H3 0.9500 . ? C1 C3 1.396(2) 2_657 ? C1 C4 1.499(2) . ? C7 C8 1.394(2) . ? C7 C10 1.503(2) . ? C8 C6 1.394(2) 2_746 ? C8 H8 0.9500 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? 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 C9 O5 H5 109.5 . . ? C10 O7 H7 109.5 . . ? C5 O4 H4 109.5 . . ? C4 O2 H2 109.5 . . ? C12 O10 H10 107(2) . . ? C11 O9 H9 111(2) . . ? O3 C5 O4 125.53(16) . . ? O3 C5 C2 120.52(15) . . ? O4 C5 C2 113.82(14) . . ? C3 C2 C1 119.38(15) . . ? C3 C2 C5 115.94(15) . . ? C1 C2 C5 124.65(15) . . ? C8 C6 C7 119.28(15) 2_746 . ? C8 C6 C9 116.34(15) 2_746 . ? C7 C6 C9 124.31(15) . . ? C2 C3 C1 121.31(15) . 2_657 ? C2 C3 H3 119.3 . . ? C1 C3 H3 119.3 2_657 . ? C3 C1 C2 119.30(15) 2_657 . ? C3 C1 C4 118.67(15) 2_657 . ? C2 C1 C4 121.90(15) . . ? C8 C7 C6 119.30(15) . . ? C8 C7 C10 117.20(15) . . ? C6 C7 C10 123.34(15) . . ? C7 C8 C6 121.41(15) . 2_746 ? C7 C8 H8 119.3 . . ? C6 C8 H8 119.3 2_746 . ? O6 C9 O5 125.30(16) . . ? O6 C9 C6 120.40(15) . . ? O5 C9 C6 114.26(15) . . ? O8 C10 O7 125.66(16) . . ? O8 C10 C7 122.31(16) . . ? O7 C10 C7 111.95(14) . . ? O1 C4 O2 124.97(16) . . ? O1 C4 C1 122.73(15) . . ? O2 C4 C1 112.28(14) . . ? O9 C11 H11A 109.5 . . ? O9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? O9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? O10 C12 H12A 109.5 . . ? O10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O3 C5 C2 C3 -49.5(2) . . . . ? O4 C5 C2 C3 126.63(16) . . . . ? O3 C5 C2 C1 132.22(18) . . . . ? O4 C5 C2 C1 -51.7(2) . . . . ? C1 C2 C3 C1 0.4(3) . . . 2_657 ? C5 C2 C3 C1 -177.96(15) . . . 2_657 ? C3 C2 C1 C3 -0.4(3) . . . 2_657 ? C5 C2 C1 C3 177.82(16) . . . 2_657 ? C3 C2 C1 C4 175.40(15) . . . . ? C5 C2 C1 C4 -6.3(3) . . . . ? C8 C6 C7 C8 -0.4(3) 2_746 . . . ? C9 C6 C7 C8 176.57(16) . . . . ? C8 C6 C7 C10 174.96(16) 2_746 . . . ? C9 C6 C7 C10 -8.0(3) . . . . ? C6 C7 C8 C6 0.4(3) . . . 2_746 ? C10 C7 C8 C6 -175.23(15) . . . 2_746 ? C8 C6 C9 O6 -27.0(2) 2_746 . . . ? C7 C6 C9 O6 155.94(17) . . . . ? C8 C6 C9 O5 150.67(16) 2_746 . . . ? C7 C6 C9 O5 -26.4(2) . . . . ? C8 C7 C10 O8 125.98(18) . . . . ? C6 C7 C10 O8 -49.5(2) . . . . ? C8 C7 C10 O7 -51.0(2) . . . . ? C6 C7 C10 O7 133.49(17) . . . . ? C3 C1 C4 O1 152.24(17) 2_657 . . . ? C2 C1 C4 O1 -23.6(3) . . . . ? C3 C1 C4 O2 -26.0(2) 2_657 . . . ? C2 C1 C4 O2 158.11(16) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.53 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.345 _refine_diff_density_min -0.307 _refine_diff_density_rms 0.062