Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _publ_section_title ;An investigation in to the factors favouring solid state [2+2] cycloaddition reactions; the [2+2] cycloaddition reaction of coumarin-3-carboxylic acid ; _publ_contact_author_name 'Prof. P. Raithby' _publ_contact_author_email P.R.RAITHBY@BATH.AC.UK loop_ _publ_author_name 'P. Raithby' 'M. Mahon' 'Hazel A. Sparkes' # Attachment 'K03HAS1_1a.CIF' data_e:\hazel\papers\coumar~1\k03has1\k03has1 _database_code_depnum_ccdc_archive 'CCDC 664449' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H6 O4' _chemical_formula_sum 'C10 H6 O4' _chemical_formula_weight 190.15 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 monoclinic _symmetry_space_group_name_H-M 'P 21/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 11.2410(7) _cell_length_b 5.4821(4) _cell_length_c 13.7463(12) _cell_angle_alpha 90.00 _cell_angle_beta 107.108(3) _cell_angle_gamma 90.00 _cell_volume 809.62(11) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3490 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 26.373 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.560 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 392 _exptl_absorpt_coefficient_mu 0.123 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.899 _exptl_absorpt_correction_T_max 0.966 _exptl_absorpt_process_details 'Sortav (Blessing 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'Nonius KappaCCD' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4016 _diffrn_reflns_av_R_equivalents 0.0531 _diffrn_reflns_av_sigmaI/netI 0.0750 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.79 _diffrn_reflns_theta_max 26.37 _reflns_number_total 1617 _reflns_number_gt 1014 _reflns_threshold_expression >2sigma(I) _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 'SIR92 (Altomare, 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'POV-Ray (Cason, 1991)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0598P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1617 _refine_ls_number_parameters 128 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0967 _refine_ls_R_factor_gt 0.0494 _refine_ls_wR_factor_ref 0.1230 _refine_ls_wR_factor_gt 0.1058 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _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 O1 O 0.60016(13) 0.1982(2) 0.24595(10) 0.0259(4) Uani 1 1 d . . . O2 O 0.72692(13) 0.3045(2) 0.15852(11) 0.0327(4) Uani 1 1 d . . . O3 O 0.76158(15) 0.0284(2) 0.01586(11) 0.0401(5) Uani 1 1 d . . . H3A H 0.7677 0.1473 0.0556 0.048 Uiso 1 1 calc R . . O4 O 0.64418(14) -0.2987(2) -0.02817(11) 0.0357(4) Uani 1 1 d . . . C1 C 0.51892(18) 0.0352(3) 0.26944(15) 0.0235(5) Uani 1 1 d . . . C2 C 0.47625(19) 0.0911(4) 0.35118(15) 0.0286(5) Uani 1 1 d . . . H2 H 0.5026 0.2358 0.3895 0.034 Uiso 1 1 calc R . . C3 C 0.39463(19) -0.0676(4) 0.37584(16) 0.0307(5) Uani 1 1 d . . . H3 H 0.3648 -0.0323 0.4322 0.037 Uiso 1 1 calc R . . C4 C 0.35518(19) -0.2790(4) 0.31937(16) 0.0299(5) Uani 1 1 d . . . H4 H 0.2983 -0.3860 0.3369 0.036 Uiso 1 1 calc R . . C5 C 0.39849(19) -0.3329(3) 0.23844(16) 0.0282(5) Uani 1 1 d . . . H5 H 0.3713 -0.4772 0.2001 0.034 Uiso 1 1 calc R . . C6 C 0.48279(18) -0.1763(3) 0.21179(15) 0.0236(5) Uani 1 1 d . . . C7 C 0.53472(19) -0.2236(3) 0.13073(16) 0.0249(5) Uani 1 1 d . . . H7 H 0.5103 -0.3657 0.0902 0.030 Uiso 1 1 calc R . . C8 C 0.61795(18) -0.0692(3) 0.11079(14) 0.0224(5) Uani 1 1 d . . . C9 C 0.65342(19) 0.1510(3) 0.17089(15) 0.0251(5) Uani 1 1 d . . . C10 C 0.6747(2) -0.1248(4) 0.02752(16) 0.0280(5) 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 O1 0.0266(8) 0.0241(7) 0.0280(8) -0.0028(6) 0.0095(7) -0.0002(6) O2 0.0317(9) 0.0305(8) 0.0358(9) -0.0007(6) 0.0099(8) -0.0062(7) O3 0.0449(10) 0.0447(10) 0.0384(10) -0.0088(7) 0.0241(8) -0.0128(8) O4 0.0416(10) 0.0374(8) 0.0319(9) -0.0087(7) 0.0165(8) -0.0041(7) C1 0.0207(11) 0.0238(10) 0.0253(12) 0.0032(8) 0.0055(10) 0.0014(9) C2 0.0291(13) 0.0304(11) 0.0246(12) -0.0033(9) 0.0054(10) 0.0050(10) C3 0.0280(13) 0.0393(12) 0.0259(12) 0.0028(10) 0.0095(10) 0.0067(10) C4 0.0242(12) 0.0361(12) 0.0311(13) 0.0054(10) 0.0107(10) 0.0018(9) C5 0.0244(12) 0.0277(10) 0.0309(13) 0.0004(9) 0.0056(10) 0.0003(9) C6 0.0205(11) 0.0245(10) 0.0248(12) 0.0011(8) 0.0052(9) 0.0031(9) C7 0.0250(12) 0.0238(10) 0.0239(12) -0.0010(8) 0.0042(9) 0.0037(9) C8 0.0211(11) 0.0243(10) 0.0215(11) 0.0011(8) 0.0057(9) 0.0026(9) C9 0.0238(12) 0.0269(11) 0.0224(12) 0.0033(8) 0.0035(10) 0.0008(9) C10 0.0261(12) 0.0300(11) 0.0273(12) 0.0028(10) 0.0070(10) -0.0003(10) _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 O1 C9 1.361(2) . ? O1 C1 1.382(2) . ? O2 C9 1.226(2) . ? O3 C10 1.333(2) . ? O3 H3A 0.8400 . ? O4 C10 1.208(2) . ? C1 C2 1.380(3) . ? C1 C6 1.395(3) . ? C2 C3 1.377(3) . ? C2 H2 0.9500 . ? C3 C4 1.393(3) . ? C3 H3 0.9500 . ? C4 C5 1.371(3) . ? C4 H4 0.9500 . ? C5 C6 1.405(3) . ? C5 H5 0.9500 . ? C6 C7 1.426(3) . ? C7 C8 1.348(3) . ? C7 H7 0.9500 . ? C8 C9 1.451(3) . ? C8 C10 1.496(3) . ? 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 O1 C1 121.46(15) . . ? C10 O3 H3A 109.5 . . ? C2 C1 O1 117.27(17) . . ? C2 C1 C6 122.30(18) . . ? O1 C1 C6 120.43(17) . . ? C3 C2 C1 118.45(18) . . ? C3 C2 H2 120.8 . . ? C1 C2 H2 120.8 . . ? C2 C3 C4 120.96(18) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C5 C4 C3 120.03(19) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C4 C5 C6 120.50(19) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C1 C6 C5 117.74(19) . . ? C1 C6 C7 118.51(17) . . ? C5 C6 C7 123.73(18) . . ? C8 C7 C6 120.87(18) . . ? C8 C7 H7 119.6 . . ? C6 C7 H7 119.6 . . ? C7 C8 C9 119.82(18) . . ? C7 C8 C10 120.36(17) . . ? C9 C8 C10 119.81(16) . . ? O2 C9 O1 116.05(17) . . ? O2 C9 C8 125.15(18) . . ? O1 C9 C8 118.78(16) . . ? O4 C10 O3 120.17(18) . . ? O4 C10 C8 122.68(18) . . ? O3 C10 C8 117.14(17) . . ? 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 O3 H3A O2 0.84 1.83 2.5955(18) 151.4 . _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.270 _refine_diff_density_min -0.245 _refine_diff_density_rms 0.079 # Attachment 'H03HAS1_1b_single_crystal.CIF' data_h03has1(2) _database_code_depnum_ccdc_archive 'CCDC 664450' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H12 O8' _chemical_formula_sum 'C20 H12 O8' _chemical_formula_weight 380.30 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 monoclinic _symmetry_space_group_name_H-M 'P 21/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 11.348(3) _cell_length_b 5.881(3) _cell_length_c 12.376(5) _cell_angle_alpha 90.00 _cell_angle_beta 113.236(13) _cell_angle_gamma 90.00 _cell_volume 758.9(5) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 12869 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.485 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.664 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 392 _exptl_absorpt_coefficient_mu 0.131 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.653 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'Sortav (Blessing 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'Nonius KappaCCD' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2945 _diffrn_reflns_av_R_equivalents 0.1044 _diffrn_reflns_av_sigmaI/netI 0.1655 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.58 _diffrn_reflns_theta_max 27.65 _reflns_number_total 1409 _reflns_number_gt 674 _reflns_threshold_expression >2sigma(I) _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 'SIR-97 (Altomare, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'POV-Ray (Cason, 1991)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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. Completeness of data are low because the crystal had undergone a [2+2] cycloaddition reaction upon irradiation which resulted in degradation of the single crystal and this structure was recorded straight after irradiation without recrystallization. The structure reported here is consistent with an independently determined powder diffraction structure of the irradiation product. ; _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^)+(0.0919P)^2^+0.2893P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1409 _refine_ls_number_parameters 128 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1911 _refine_ls_R_factor_gt 0.0847 _refine_ls_wR_factor_ref 0.2273 _refine_ls_wR_factor_gt 0.1815 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _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 O1 O 0.5786(3) 0.2377(5) 0.7212(3) 0.0485(10) Uani 1 1 d . . . O2 O 0.7293(3) 0.3470(6) 0.6655(3) 0.0563(11) Uani 1 1 d . . . O3 O 0.8141(3) 0.0592(6) 0.5496(3) 0.0592(11) Uani 1 1 d . . . H3A H 0.7980 0.1943 0.5611 0.071 Uiso 1 1 calc R . . O4 O 0.7074(3) -0.2623(7) 0.4992(3) 0.0578(11) Uani 1 1 d . . . C1 C 0.5050(5) 0.0628(8) 0.7398(4) 0.0463(13) Uani 1 1 d . . . C2 C 0.4719(5) 0.0888(9) 0.8337(4) 0.0531(14) Uani 1 1 d . . . H2 H 0.4963 0.2220 0.8808 0.064 Uiso 1 1 calc R . . C3 C 0.4026(5) -0.0801(9) 0.8597(5) 0.0574(15) Uani 1 1 d . . . H3 H 0.3778 -0.0623 0.9241 0.069 Uiso 1 1 calc R . . C4 C 0.3693(5) -0.2757(10) 0.7916(4) 0.0539(14) Uani 1 1 d . . . H4 H 0.3247 -0.3949 0.8112 0.065 Uiso 1 1 calc R . . C5 C 0.4010(5) -0.2967(8) 0.6954(4) 0.0509(13) Uani 1 1 d . . . H5 H 0.3761 -0.4295 0.6480 0.061 Uiso 1 1 calc R . . C6 C 0.4687(4) -0.1273(9) 0.6663(4) 0.0476(13) Uani 1 1 d . . . C7 C 0.5026(4) -0.1395(9) 0.5611(4) 0.0477(13) Uani 1 1 d . . . H7 H 0.5267 -0.2977 0.5483 0.057 Uiso 1 1 calc R . . C8 C 0.6033(4) 0.0343(8) 0.5586(4) 0.0452(12) Uani 1 1 d . . . C9 C 0.6442(5) 0.2141(9) 0.6546(4) 0.0468(13) Uani 1 1 d . . . C10 C 0.7138(5) -0.0706(10) 0.5357(4) 0.0467(12) 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 O1 0.051(2) 0.054(2) 0.0389(17) -0.0054(14) 0.0163(16) -0.0047(16) O2 0.053(2) 0.063(2) 0.049(2) -0.0046(17) 0.0162(17) -0.011(2) O3 0.049(2) 0.072(2) 0.055(2) -0.0002(19) 0.0189(18) 0.0002(19) O4 0.056(2) 0.067(3) 0.050(2) 0.0006(18) 0.0195(17) 0.0075(18) C1 0.042(3) 0.051(3) 0.041(3) 0.007(2) 0.010(2) 0.002(2) C2 0.049(3) 0.065(4) 0.038(3) -0.002(2) 0.010(2) 0.001(3) C3 0.049(3) 0.075(4) 0.043(3) 0.005(3) 0.012(2) -0.003(3) C4 0.043(3) 0.068(4) 0.046(3) 0.004(3) 0.013(2) -0.005(2) C5 0.044(3) 0.058(3) 0.043(3) 0.001(2) 0.008(2) -0.002(3) C6 0.041(3) 0.058(3) 0.039(3) -0.002(2) 0.010(2) 0.001(2) C7 0.042(3) 0.056(3) 0.038(3) 0.000(2) 0.008(2) 0.003(2) C8 0.037(3) 0.058(3) 0.037(3) -0.006(2) 0.010(2) -0.005(2) C9 0.048(3) 0.052(3) 0.035(3) 0.004(2) 0.011(2) 0.000(3) C10 0.042(3) 0.057(3) 0.038(3) 0.002(2) 0.013(2) 0.002(3) _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 O1 C9 1.318(6) . ? O1 C1 1.400(5) . ? O2 C9 1.208(6) . ? O3 C10 1.325(6) . ? O3 H3A 0.8400 . ? O4 C10 1.206(6) . ? C1 C2 1.364(7) . ? C1 C6 1.396(7) . ? C2 C3 1.381(7) . ? C2 H2 0.9500 . ? C3 C4 1.388(8) . ? C3 H3 0.9500 . ? C4 C5 1.379(7) . ? C4 H4 0.9500 . ? C5 C6 1.389(7) . ? C5 H5 0.9500 . ? C6 C7 1.498(7) . ? C7 C8 1.543(7) . ? C7 C8 1.617(7) 3_656 ? C7 H7 1.0000 . ? C8 C9 1.520(7) . ? C8 C10 1.521(7) . ? C8 C7 1.617(7) 3_656 ? 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 O1 C1 123.1(4) . . ? C10 O3 H3A 109.5 . . ? C2 C1 C6 122.3(5) . . ? C2 C1 O1 116.1(4) . . ? C6 C1 O1 121.6(5) . . ? C1 C2 C3 119.4(5) . . ? C1 C2 H2 120.3 . . ? C3 C2 H2 120.3 . . ? C2 C3 C4 119.9(5) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C5 C4 C3 119.8(5) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? C4 C5 C6 121.3(5) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? C5 C6 C1 117.2(5) . . ? C5 C6 C7 123.3(5) . . ? C1 C6 C7 119.5(5) . . ? C6 C7 C8 115.6(4) . . ? C6 C7 C8 115.2(4) . 3_656 ? C8 C7 C8 91.0(3) . 3_656 ? C6 C7 H7 111.2 . . ? C8 C7 H7 111.2 . . ? C8 C7 H7 111.2 3_656 . ? C9 C8 C10 114.1(4) . . ? C9 C8 C7 116.5(4) . . ? C10 C8 C7 114.0(4) . . ? C9 C8 C7 109.7(4) . 3_656 ? C10 C8 C7 110.7(4) . 3_656 ? C7 C8 C7 89.0(3) . 3_656 ? O2 C9 O1 119.1(4) . . ? O2 C9 C8 121.4(5) . . ? O1 C9 C8 119.2(4) . . ? O4 C10 O3 120.6(5) . . ? O4 C10 C8 121.1(5) . . ? O3 C10 C8 118.1(5) . . ? 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 O3 H3A O2 0.84 1.97 2.634(5) 135.3 . _diffrn_measured_fraction_theta_max 0.794 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.830 _refine_diff_density_max 0.268 _refine_diff_density_min -0.250 _refine_diff_density_rms 0.074 # Attachment 'Photoproduct_1b_powder.cif' data_1b_powder _database_code_depnum_ccdc_archive 'CCDC 664451' _chemical_name_systematic ; ; _chemical_name_common ? _chemical_formula_moiety 'C20 H12 O8' _chemical_formula_sum 'C20 H12 O8' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_weight 380.31 _chemical_melting_point ? _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +x,+y,+z 2 -x+1/2,+y+1/2,-z+1/2 -1 -x,-y,-z -2 +x+1/2,-y+1/2,+z+1/2 _cell_length_a 11.3948(4) _cell_length_b 5.97016(19) _cell_length_c 12.4931(5) _cell_angle_alpha 90 _cell_angle_beta 112.8586(20) _cell_angle_gamma 90 _cell_volume 783.14453 _cell_formula_units_Z 4 _cell_measurement_temperature 300 _cell_special_details ; ? ; _exptl_crystal_density_diffrn ? _exptl_absorpt_coefficient_mu ? _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 300 _diffrn_radiation_type 'Cu K\a~1~' _diffrn_radiation_wavelength 1.54056 _diffrn_radiation_source 'sealed X-ray tube' _diffrn_radiation_monochromator Ge _diffrn_measurement_device 'scintillation counter' _diffrn_measurement_method 'Debye Scherrer' _diffrn_reflns_limit_h_min ? _diffrn_reflns_limit_h_max ? _diffrn_reflns_limit_k_min ? _diffrn_reflns_limit_k_max ? _diffrn_reflns_limit_l_min ? _diffrn_reflns_limit_l_max ? _refine_special_details ; ? ; _refine_ls_structure_factor_coef ? _refine_ls_matrix_type full _refine_ls_R_factor_all ? _refine_ls_goodness_of_fit_all 0.48 _refine_ls_restrained_S_all ? _refine_ls_restrained_S_obs ? _refine_ls_number_reflns 240 _refine_ls_number_parameters 26 _refine_ls_number_restraints 44 _refine_ls_number_constraints ? _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme ? _refine_ls_shift/esd_max 0.01 _refine_ls_shift/esd_mean 0.00 _refine_ls_extinction_method ? _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? 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' O O 0.0106 0.0060 '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' _computing_data_collection 'Bruker D8 Advance' _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'Dash (David et al. 1998)' _computing_structure_refinement 'GSAS (Larson et al. 1994)' _computing_molecular_graphics ? _computing_publication_material 'Encifer (CCDC)' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_thermal_displace_type _atom_site_U_iso_or_equiv _atom_site_symmetry_multiplicity C5 -0.09505 0.30452 0.19343 1.0 Uiso 0.01 4 C4 -0.12875 0.28458 0.28949 1.0 Uiso 0.01 4 C6 -0.02778 0.1316 0.16639 1.0 Uiso 0.01 4 C3 -0.09279 0.08953 0.35672 1.0 Uiso 0.01 4 C7 0.00033 0.13913 0.05894 1.0 Uiso 0.01 4 C2 -0.02994 -0.07203 0.33202 1.0 Uiso 0.01 4 C1 0.0043 -0.06198 0.23602 1.0 Uiso 0.01 4 O1 0.08262 -0.22787 0.22708 1.0 Uiso 0.01 4 C8 0.09916 -0.03306 0.05481 1.0 Uiso 0.01 4 C10 0.20829 0.07754 0.03225 1.0 Uiso 0.01 4 C9 0.13794 -0.2073 0.14909 1.0 Uiso 0.01 4 O3 0.31164 -0.05801 0.05077 1.0 Uiso 0.01 4 O2 0.22518 -0.3381 0.16409 1.0 Uiso 0.01 4 O4 0.20531 0.26268 -0.00297 1.0 Uiso 0.01 4 H5 -0.12063 0.45654 0.13976 1.0 Uiso 0.025 4 H4 -0.18001 0.42134 0.31158 1.0 Uiso 0.025 4 H3a -0.11729 0.06793 0.43295 1.0 Uiso 0.025 4 H7 0.02922 0.31124 0.04325 1.0 Uiso 0.025 4 H2 -0.00537 -0.22335 0.38684 1.0 Uiso 0.025 4 H3 0.30367 -0.19481 0.08929 1.0 Uiso 0.025 4 _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 C5 C4 1.39994(5) . 1_555 N C5 C6 1.403060(30) . 1_555 N C5 H5 1.098380(30) . 1_555 N C4 C5 1.39994(5) . 1_555 N C4 C3 1.40072(4) . 1_555 N C4 H4 1.099600(20) . 1_555 N C6 C5 1.403060(30) . 1_555 N C6 C7 1.49693(5) . 1_555 N C6 C1 1.40673(4) . 1_555 N C3 C4 1.40072(4) . 1_555 N C3 C2 1.307680(30) . 1_555 N C3 H3a 1.09921(4) . 1_555 N C3 H2 2.08128(6) . 1_555 N C7 C6 1.49693(5) . 1_555 N C7 C7 2.21813(6) . -1_555 N C7 C8 1.54033(4) . 1_555 N C7 C8 1.56661(5) . -1_555 N C7 H7 1.119240(30) . 1_555 N C2 C3 1.307680(30) . 1_555 N C2 C1 1.39925(5) . 1_555 N C2 H3a 2.06257(5) . 1_555 N C2 H2 1.102090(30) . 1_555 N C1 C6 1.40673(4) . 1_555 N C1 C2 1.39925(5) . 1_555 N C1 O1 1.366380(30) . 1_555 N O1 C1 1.366380(30) . 1_555 N O1 C9 1.35616(4) . 1_555 N O1 O2 2.16441(6) . 1_555 N C8 C7 1.54033(4) . 1_555 N C8 C7 1.56661(5) . -1_555 N C8 C8 2.17569(8) . -1_555 N C8 C10 1.52781(4) . 1_555 N C8 C9 1.50340(4) . 1_555 N C10 C8 1.52781(4) . 1_555 N C10 O3 1.37242(4) . 1_555 N C10 O4 1.185270(30) . 1_555 N C10 H3 1.93161(5) . 1_555 N C9 O1 1.35616(4) . 1_555 N C9 C8 1.50340(4) . 1_555 N C9 O2 1.220030(30) . 1_555 N O3 C10 1.37242(4) . 1_555 N O3 H3 0.969970(20) . 1_555 N O2 O1 2.16441(6) . 1_555 N O2 C9 1.220030(30) . 1_555 N O2 H3 1.74762(4) . 1_555 N O4 C10 1.185270(30) . 1_555 N H5 C5 1.098380(30) . 1_555 N H4 C4 1.099600(20) . 1_555 N H3a C3 1.09921(4) . 1_555 N H3a C2 2.06257(5) . 1_555 N H7 C7 1.119240(30) . 1_555 N H2 C3 2.08128(6) . 1_555 N H2 C2 1.102090(30) . 1_555 N H3 C10 1.93161(5) . 1_555 N H3 O3 0.969970(20) . 1_555 N H3 O2 1.74762(4) . 1_555 N 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 C4 C5 C6 120.0835(13) 1_555 . 1_555 N C4 C5 H5 119.8357(14) 1_555 . 1_555 N C6 C5 H5 120.0784(21) 1_555 . 1_555 N C5 C4 C3 118.0928(14) 1_555 . 1_555 N C5 C4 H4 120.0882(13) 1_555 . 1_555 N C3 C4 H4 121.8035(21) 1_555 . 1_555 N C5 C6 C7 121.4042(12) 1_555 . 1_555 N C5 C6 C1 119.3878(21) 1_555 . 1_555 N C7 C6 C1 118.9720(15) 1_555 . 1_555 N C4 C3 C2 122.0849(21) 1_555 . 1_555 N C4 C3 H3a 120.2245(14) 1_555 . 1_555 N C2 C3 H3a 117.6905(14) 1_555 . 1_555 N C6 C7 C8 115.0831(14) 1_555 . 1_555 N C6 C7 C8 118.0227(25) 1_555 . -1_555 N C6 C7 H7 111.3829(8) 1_555 . 1_555 N C8 C7 C8 88.8928(24) 1_555 . -1_555 N C8 C7 H7 109.7691(22) 1_555 . 1_555 N C8 C7 H7 111.7540(17) -1_555 . 1_555 N C3 C2 C1 122.0933(12) 1_555 . 1_555 N C3 C2 H2 119.2211(21) 1_555 . 1_555 N C1 C2 H2 118.6616(15) 1_555 . 1_555 N C6 C1 C2 118.2382(15) 1_555 . 1_555 N C6 C1 O1 124.4809(18) 1_555 . 1_555 N C2 C1 O1 116.5751(13) 1_555 . 1_555 N C1 O1 C9 119.5784(14) 1_555 . 1_555 N C7 C8 C7 91.1072(24) 1_555 . -1_555 N C7 C8 C10 112.0743(24) 1_555 . 1_555 N C7 C8 C9 115.5784(19) 1_555 . 1_555 N C7 C8 C10 111.1853(25) -1_555 . 1_555 N C7 C8 C9 108.6538(26) -1_555 . 1_555 N C10 C8 C9 115.5306(20) 1_555 . 1_555 N C8 C10 O3 114.8768(24) 1_555 . 1_555 N C8 C10 O4 124.2977(11) 1_555 . 1_555 N O3 C10 O4 120.7611(15) 1_555 . 1_555 N O1 C9 C8 123.2559(18) 1_555 . 1_555 N O1 C9 O2 114.2106(18) 1_555 . 1_555 N C8 C9 O2 122.4932(16) 1_555 . 1_555 N C10 O3 H3 109.9119(19) 1_555 . 1_555 N