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


