# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_rtm1s
_database_code_depnum_ccdc_archive 'CCDC 1499424'
_audit_update_record             
;
2016-08-16 deposited with the CCDC.
2016-11-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
5-methyl-8-(propan-2-yl)hexahydro-4,7-ethano-2-benzofuran-1,3-dione
_chemical_name_common            'phellandrene anhydride'
_chemical_melting_point          399
_chemical_formula_moiety         'C14 H18 O3'
_chemical_formula_sum            'C14 H18 O3'
_chemical_formula_weight         234.28

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           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.8700(18)
_cell_length_b                   8.309(2)
_cell_length_c                   22.230(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1268.9(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2539
_cell_measurement_theta_min      2.612
_cell_measurement_theta_max      28.250

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_F_000             504
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9758
_exptl_absorpt_correction_T_max  0.9849
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.34
_diffrn_reflns_number            8269
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_av_sigmaI/netI    0.0251
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.83
_diffrn_reflns_theta_max         28.36
_reflns_number_total             3065
_reflns_number_gt                2479
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0679P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.3(14)
_refine_ls_number_reflns         3065
_refine_ls_number_parameters     157
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0453
_refine_ls_wR_factor_ref         0.1179
_refine_ls_wR_factor_gt          0.1109
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_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
C1 C 0.9314(3) 0.7633(2) 0.04114(7) 0.0519(4) Uani 1 1 d . . .
C2 C 0.9458(2) 0.59578(18) 0.06553(6) 0.0441(3) Uani 1 1 d . . .
H2 H 1.0168 0.5261 0.0375 0.053 Uiso 1 1 calc R . .
C3 C 1.0586(2) 0.6143(2) 0.12447(7) 0.0502(4) Uani 1 1 d . . .
H3 H 1.1821 0.5556 0.1223 0.060 Uiso 1 1 calc R . .
C4 C 1.0956(3) 0.7910(2) 0.12924(8) 0.0602(5) Uani 1 1 d . . .
C5 C 0.9341(3) 0.5496(2) 0.17672(6) 0.0504(4) Uani 1 1 d . . .
H5 H 1.0024 0.5614 0.2152 0.060 Uiso 1 1 calc R . .
C6 C 0.7443(2) 0.64216(19) 0.17703(6) 0.0441(3) Uani 1 1 d . . .
C7 C 0.6477(2) 0.62989(18) 0.12571(6) 0.0393(3) Uani 1 1 d . . .
H7 H 0.5297 0.6821 0.1193 0.047 Uiso 1 1 calc R . .
C8 C 0.7411(2) 0.52625(17) 0.07871(5) 0.0392(3) Uani 1 1 d . . .
H8 H 0.6618 0.5228 0.0421 0.047 Uiso 1 1 calc R . .
C9 C 0.7708(2) 0.35521(18) 0.10487(6) 0.0445(3) Uani 1 1 d . . .
H9 H 0.8493 0.2934 0.0762 0.053 Uiso 1 1 calc R . .
C10 C 0.8892(3) 0.3728(2) 0.16369(7) 0.0571(5) Uani 1 1 d . . .
H10A H 0.8158 0.3276 0.1969 0.069 Uiso 1 1 calc R . .
H10B H 1.0101 0.3133 0.1601 0.069 Uiso 1 1 calc R . .
C11 C 0.6806(3) 0.7323(2) 0.23182(7) 0.0678(5) Uani 1 1 d . . .
H11A H 0.7686 0.8200 0.2391 0.102 Uiso 1 1 calc R . .
H11B H 0.6807 0.6612 0.2659 0.102 Uiso 1 1 calc R . .
H11C H 0.5517 0.7737 0.2257 0.102 Uiso 1 1 calc R . .
C12 C 0.5774(3) 0.26458(18) 0.11455(7) 0.0510(4) Uani 1 1 d . . .
H12 H 0.5075 0.3170 0.1476 0.061 Uiso 1 1 calc R . .
C13 C 0.6181(4) 0.0905(2) 0.13292(11) 0.0865(7) Uani 1 1 d . . .
H13A H 0.4973 0.0366 0.1411 0.130 Uiso 1 1 calc R . .
H13B H 0.6979 0.0893 0.1684 0.130 Uiso 1 1 calc R . .
H13C H 0.6847 0.0362 0.1008 0.130 Uiso 1 1 calc R . .
C14 C 0.4474(3) 0.2672(3) 0.05969(9) 0.0760(6) Uani 1 1 d . . .
H14A H 0.5183 0.2273 0.0256 0.114 Uiso 1 1 calc R . .
H14B H 0.4058 0.3755 0.0520 0.114 Uiso 1 1 calc R . .
H14C H 0.3358 0.2003 0.0667 0.114 Uiso 1 1 calc R . .
O1 O 1.1716(3) 0.8644(2) 0.16863(7) 0.0909(5) Uani 1 1 d . . .
O2 O 1.02161(18) 0.87067(16) 0.07931(6) 0.0609(3) Uani 1 1 d . . .
O3 O 0.8537(2) 0.81070(16) -0.00332(6) 0.0694(4) Uani 1 1 d . . .


_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
C1 O3 1.190(2) . ?
C1 O2 1.379(2) . ?
C1 C2 1.497(2) . ?
C2 C3 1.530(2) . ?
C2 C8 1.549(2) . ?
C2 H2 0.9800 . ?
C3 C4 1.494(3) . ?
C3 C5 1.539(2) . ?
C3 H3 0.9800 . ?
C4 O1 1.188(2) . ?
C4 O2 1.389(2) . ?
C5 C6 1.514(3) . ?
C5 C10 1.529(3) . ?
C5 H5 0.9800 . ?
C6 C7 1.324(2) . ?
C6 C11 1.495(2) . ?
C7 C8 1.498(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.549(2) . ?
C8 H8 0.9800 . ?
C9 C10 1.547(2) . ?
C9 C12 1.542(2) . ?
C9 H9 0.9800 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C14 1.511(3) . ?
C12 C13 1.529(2) . ?
C12 H12 0.9800 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

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
O3 C1 O2 119.90(16) . . ?
O3 C1 C2 129.65(16) . . ?
O2 C1 C2 110.43(14) . . ?
C1 C2 C3 104.50(13) . . ?
C1 C2 C8 110.81(13) . . ?
C3 C2 C8 109.61(11) . . ?
C1 C2 H2 110.6 . . ?
C3 C2 H2 110.6 . . ?
C8 C2 H2 110.6 . . ?
C4 C3 C2 104.22(14) . . ?
C4 C3 C5 112.58(14) . . ?
C2 C3 C5 109.25(13) . . ?
C4 C3 H3 110.2 . . ?
C2 C3 H3 110.2 . . ?
C5 C3 H3 110.2 . . ?
O1 C4 O2 120.3(2) . . ?
O1 C4 C3 129.18(19) . . ?
O2 C4 C3 110.47(14) . . ?
C6 C5 C10 108.37(14) . . ?
C6 C5 C3 107.77(12) . . ?
C10 C5 C3 107.73(13) . . ?
C6 C5 H5 110.9 . . ?
C10 C5 H5 110.9 . . ?
C3 C5 H5 110.9 . . ?
C7 C6 C11 126.43(15) . . ?
C7 C6 C5 112.88(13) . . ?
C11 C6 C5 120.67(13) . . ?
C6 C7 C8 115.50(14) . . ?
C6 C7 H7 122.2 . . ?
C8 C7 H7 122.2 . . ?
C7 C8 C9 108.78(11) . . ?
C7 C8 C2 107.85(12) . . ?
C9 C8 C2 107.06(13) . . ?
C7 C8 H8 111.0 . . ?
C9 C8 H8 111.0 . . ?
C2 C8 H8 111.0 . . ?
C10 C9 C12 112.43(12) . . ?
C10 C9 C8 107.45(12) . . ?
C12 C9 C8 112.74(13) . . ?
C10 C9 H9 108.0 . . ?
C12 C9 H9 108.0 . . ?
C8 C9 H9 108.0 . . ?
C5 C10 C9 110.93(12) . . ?
C5 C10 H10A 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 108.0 . . ?
C6 C11 H11A 109.5 . . ?
C6 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C6 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C14 C12 C13 109.70(16) . . ?
C14 C12 C9 112.91(13) . . ?
C13 C12 C9 109.96(16) . . ?
C14 C12 H12 108.0 . . ?
C13 C12 H12 108.0 . . ?
C9 C12 H12 108.0 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C1 O2 C4 110.36(14) . . ?

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 C1 C2 C3 -178.52(17) . . . . ?
O2 C1 C2 C3 -0.12(17) . . . . ?
O3 C1 C2 C8 -60.5(2) . . . . ?
O2 C1 C2 C8 117.86(14) . . . . ?
C1 C2 C3 C4 1.04(16) . . . . ?
C8 C2 C3 C4 -117.75(14) . . . . ?
C1 C2 C3 C5 121.57(14) . . . . ?
C8 C2 C3 C5 2.78(17) . . . . ?
C2 C3 C4 O1 176.65(18) . . . . ?
C5 C3 C4 O1 58.4(3) . . . . ?
C2 C3 C4 O2 -1.67(18) . . . . ?
C5 C3 C4 O2 -119.94(14) . . . . ?
C4 C3 C5 C6 57.68(17) . . . . ?
C2 C3 C5 C6 -57.59(17) . . . . ?
C4 C3 C5 C10 174.41(14) . . . . ?
C2 C3 C5 C10 59.14(16) . . . . ?
C10 C5 C6 C7 -58.19(16) . . . . ?
C3 C5 C6 C7 58.12(18) . . . . ?
C10 C5 C6 C11 120.64(16) . . . . ?
C3 C5 C6 C11 -123.05(15) . . . . ?
C11 C6 C7 C8 -177.59(15) . . . . ?
C5 C6 C7 C8 1.17(19) . . . . ?
C6 C7 C8 C9 57.62(18) . . . . ?
C6 C7 C8 C2 -58.17(16) . . . . ?
C1 C2 C8 C7 -61.92(15) . . . . ?
C3 C2 C8 C7 52.90(15) . . . . ?
C1 C2 C8 C9 -178.83(12) . . . . ?
C3 C2 C8 C9 -64.01(15) . . . . ?
C7 C8 C9 C10 -55.23(16) . . . . ?
C2 C8 C9 C10 61.07(14) . . . . ?
C7 C8 C9 C12 69.19(15) . . . . ?
C2 C8 C9 C12 -174.51(11) . . . . ?
C6 C5 C10 C9 54.59(17) . . . . ?
C3 C5 C10 C9 -61.75(17) . . . . ?
C12 C9 C10 C5 -123.79(15) . . . . ?
C8 C9 C10 C5 0.83(18) . . . . ?
C10 C9 C12 C14 171.80(15) . . . . ?
C8 C9 C12 C14 50.15(17) . . . . ?
C10 C9 C12 C13 -65.33(18) . . . . ?
C8 C9 C12 C13 173.03(14) . . . . ?
O3 C1 O2 C4 177.62(15) . . . . ?
C2 C1 O2 C4 -0.96(18) . . . . ?
O1 C4 O2 C1 -176.81(16) . . . . ?
C3 C4 O2 C1 1.68(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.963
_diffrn_reflns_theta_full        28.36
_diffrn_measured_fraction_theta_full 0.963
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.052
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_rtm2s
_database_code_depnum_ccdc_archive 'CCDC 1499425'
_audit_update_record             
;
2016-08-16 deposited with the CCDC.
2016-11-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
5-methyl-8-(propan-2-yl)-3a,4,7,7a-tetrahydro-4,7-ethano-2-benzofuran-1,3-dione
_chemical_name_common            ?
_chemical_melting_point          363
_chemical_formula_moiety         'C14 H20 O3'
_chemical_formula_sum            'C14 H20 O3'
_chemical_formula_weight         236.30

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           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.9562(18)
_cell_length_b                   8.559(2)
_cell_length_c                   21.752(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1295.0(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2369
_cell_measurement_theta_min      2.554
_cell_measurement_theta_max      23.977

_exptl_crystal_description       cubical
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_F_000             512
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9843
_exptl_absorpt_correction_T_max  0.9876
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.34
_diffrn_reflns_number            7213
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_sigmaI/netI    0.0453
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.87
_diffrn_reflns_theta_max         28.31
_reflns_number_total             2952
_reflns_number_gt                2074
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0745P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -4.0(18)
_refine_ls_number_reflns         2952
_refine_ls_number_parameters     157
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0496
_refine_ls_wR_factor_ref         0.1413
_refine_ls_wR_factor_gt          0.1315
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.003

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
C1 C 0.9010(3) 0.7646(3) 0.04109(9) 0.0647(6) Uani 1 1 d . . .
C2 C 0.9147(3) 0.6013(2) 0.06468(8) 0.0534(5) Uani 1 1 d . . .
H2 H 0.9823 0.5356 0.0348 0.064 Uiso 1 1 calc R . .
C3 C 1.0337(3) 0.6148(3) 0.12361(8) 0.0617(6) Uani 1 1 d . . .
H3 H 1.1536 0.5561 0.1186 0.074 Uiso 1 1 calc R . .
C4 C 1.0785(3) 0.7836(3) 0.12827(10) 0.0727(7) Uani 1 1 d . . .
C5 C 0.9186(3) 0.5448(3) 0.17691(8) 0.0659(6) Uani 1 1 d . . .
H5 H 0.9929 0.5514 0.2151 0.079 Uiso 1 1 calc R . .
C6 C 0.7275(3) 0.6308(3) 0.18412(9) 0.0742(7) Uani 1 1 d . . .
H6 H 0.6555 0.5480 0.2050 0.089 Uiso 1 1 calc R . .
C7 C 0.6230(2) 0.6314(3) 0.12730(7) 0.0513(5) Uani 1 1 d . . .
H7A H 0.6137 0.7378 0.1123 0.062 Uiso 1 1 calc R . .
H7B H 0.4935 0.5936 0.1346 0.062 Uiso 1 1 calc R . .
C8 C 0.7173(2) 0.5311(2) 0.07890(7) 0.0486(4) Uani 1 1 d . . .
H8 H 0.6381 0.5288 0.0416 0.058 Uiso 1 1 calc R . .
C9 C 0.8763(3) 0.3764(3) 0.16167(9) 0.0737(6) Uani 1 1 d . . .
H9A H 0.8116 0.3274 0.1961 0.088 Uiso 1 1 calc R . .
H9B H 0.9960 0.3211 0.1546 0.088 Uiso 1 1 calc R . .
C10 C 0.7473(3) 0.3645(2) 0.10336(7) 0.0568(5) Uani 1 1 d . . .
H10 H 0.8202 0.3068 0.0722 0.068 Uiso 1 1 calc R . .
C11 C 0.7028(5) 0.7530(3) 0.22972(10) 0.1022(10) Uani 1 1 d . . .
H11A H 0.7665 0.8463 0.2161 0.153 Uiso 1 1 calc R . .
H11B H 0.7574 0.7197 0.2681 0.153 Uiso 1 1 calc R . .
H11C H 0.5683 0.7739 0.2352 0.153 Uiso 1 1 calc R . .
C12 C 0.5596(3) 0.2744(2) 0.11474(9) 0.0658(6) Uani 1 1 d . . .
H12 H 0.4918 0.3252 0.1488 0.079 Uiso 1 1 calc R . .
C13 C 0.6024(5) 0.1073(4) 0.13372(15) 0.1165(11) Uani 1 1 d . . .
H13A H 0.4846 0.0555 0.1444 0.175 Uiso 1 1 calc R . .
H13B H 0.6871 0.1075 0.1686 0.175 Uiso 1 1 calc R . .
H13C H 0.6625 0.0532 0.1002 0.175 Uiso 1 1 calc R . .
C14 C 0.4287(4) 0.2768(3) 0.05929(11) 0.0917(8) Uani 1 1 d . . .
H14A H 0.4960 0.2354 0.0244 0.137 Uiso 1 1 calc R . .
H14B H 0.3901 0.3824 0.0509 0.137 Uiso 1 1 calc R . .
H14C H 0.3170 0.2142 0.0674 0.137 Uiso 1 1 calc R . .
O1 O 1.1674(3) 0.8516(3) 0.16668(8) 0.1060(7) Uani 1 1 d . . .
O2 O 0.99662(19) 0.86528(19) 0.07972(7) 0.0732(5) Uani 1 1 d . . .
O3 O 0.8202(3) 0.8141(2) -0.00279(7) 0.0854(5) Uani 1 1 d . . .


_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
C1 O3 1.186(2) . ?
C1 O2 1.375(2) . ?
C1 C2 1.492(3) . ?
C2 C3 1.530(3) . ?
C2 C8 1.531(3) . ?
C2 H2 0.9800 . ?
C3 C4 1.481(3) . ?
C3 C5 1.531(3) . ?
C3 H3 0.9800 . ?
C4 O1 1.191(2) . ?
C4 O2 1.389(3) . ?
C5 C9 1.508(3) . ?
C5 C6 1.528(3) . ?
C5 H5 0.9800 . ?
C6 C7 1.434(3) . ?
C6 C11 1.451(3) . ?
C6 H6 0.9800 . ?
C7 C8 1.509(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C10 1.536(3) . ?
C8 H8 0.9800 . ?
C9 C10 1.557(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C12 1.537(3) . ?
C10 H10 0.9800 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C14 1.511(3) . ?
C12 C13 1.518(4) . ?
C12 H12 0.9800 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

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
O3 C1 O2 119.8(2) . . ?
O3 C1 C2 129.9(2) . . ?
O2 C1 C2 110.25(18) . . ?
C1 C2 C3 104.59(16) . . ?
C1 C2 C8 112.33(16) . . ?
C3 C2 C8 110.23(14) . . ?
C1 C2 H2 109.9 . . ?
C3 C2 H2 109.9 . . ?
C8 C2 H2 109.9 . . ?
C4 C3 C2 104.17(17) . . ?
C4 C3 C5 116.10(18) . . ?
C2 C3 C5 108.77(15) . . ?
C4 C3 H3 109.2 . . ?
C2 C3 H3 109.2 . . ?
C5 C3 H3 109.2 . . ?
O1 C4 O2 120.0(2) . . ?
O1 C4 C3 129.3(2) . . ?
O2 C4 C3 110.66(17) . . ?
C9 C5 C6 108.28(17) . . ?
C9 C5 C3 108.04(17) . . ?
C6 C5 C3 110.12(18) . . ?
C9 C5 H5 110.1 . . ?
C6 C5 H5 110.1 . . ?
C3 C5 H5 110.1 . . ?
C7 C6 C11 121.8(2) . . ?
C7 C6 C5 110.74(15) . . ?
C11 C6 C5 121.3(2) . . ?
C7 C6 H6 98.3 . . ?
C11 C6 H6 98.3 . . ?
C5 C6 H6 98.3 . . ?
C6 C7 C8 112.29(16) . . ?
C6 C7 H7A 109.1 . . ?
C8 C7 H7A 109.1 . . ?
C6 C7 H7B 109.1 . . ?
C8 C7 H7B 109.1 . . ?
H7A C7 H7B 107.9 . . ?
C7 C8 C2 107.92(15) . . ?
C7 C8 C10 110.23(14) . . ?
C2 C8 C10 108.18(15) . . ?
C7 C8 H8 110.2 . . ?
C2 C8 H8 110.2 . . ?
C10 C8 H8 110.2 . . ?
C5 C9 C10 110.72(16) . . ?
C5 C9 H9A 109.5 . . ?
C10 C9 H9A 109.5 . . ?
C5 C9 H9B 109.5 . . ?
C10 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
C8 C10 C12 113.95(16) . . ?
C8 C10 C9 107.46(16) . . ?
C12 C10 C9 113.03(16) . . ?
C8 C10 H10 107.4 . . ?
C12 C10 H10 107.4 . . ?
C9 C10 H10 107.4 . . ?
C6 C11 H11A 109.5 . . ?
C6 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C6 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C14 C12 C13 110.4(2) . . ?
C14 C12 C10 112.10(16) . . ?
C13 C12 C10 110.5(2) . . ?
C14 C12 H12 107.9 . . ?
C13 C12 H12 107.9 . . ?
C10 C12 H12 107.9 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C1 O2 C4 110.32(18) . . ?

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 C1 C2 C3 -178.5(2) . . . . ?
O2 C1 C2 C3 -0.21(19) . . . . ?
O3 C1 C2 C8 -58.9(3) . . . . ?
O2 C1 C2 C8 119.33(16) . . . . ?
C1 C2 C3 C4 -0.39(19) . . . . ?
C8 C2 C3 C4 -121.33(16) . . . . ?
C1 C2 C3 C5 124.03(19) . . . . ?
C8 C2 C3 C5 3.1(2) . . . . ?
C2 C3 C4 O1 179.6(2) . . . . ?
C5 C3 C4 O1 60.0(3) . . . . ?
C2 C3 C4 O2 0.9(2) . . . . ?
C5 C3 C4 O2 -118.69(18) . . . . ?
C4 C3 C5 C9 176.19(16) . . . . ?
C2 C3 C5 C9 59.2(2) . . . . ?
C4 C3 C5 C6 58.1(2) . . . . ?
C2 C3 C5 C6 -58.9(2) . . . . ?
C9 C5 C6 C7 -63.5(2) . . . . ?
C3 C5 C6 C7 54.4(3) . . . . ?
C9 C5 C6 C11 143.6(2) . . . . ?
C3 C5 C6 C11 -98.5(3) . . . . ?
C11 C6 C7 C8 159.9(2) . . . . ?
C5 C6 C7 C8 7.1(3) . . . . ?
C6 C7 C8 C2 -63.3(2) . . . . ?
C6 C7 C8 C10 54.7(2) . . . . ?
C1 C2 C8 C7 -60.18(19) . . . . ?
C3 C2 C8 C7 56.0(2) . . . . ?
C1 C2 C8 C10 -179.43(14) . . . . ?
C3 C2 C8 C10 -63.23(19) . . . . ?
C6 C5 C9 C10 55.9(2) . . . . ?
C3 C5 C9 C10 -63.3(2) . . . . ?
C7 C8 C10 C12 66.90(19) . . . . ?
C2 C8 C10 C12 -175.32(14) . . . . ?
C7 C8 C10 C9 -59.2(2) . . . . ?
C2 C8 C10 C9 58.63(18) . . . . ?
C5 C9 C10 C8 3.4(2) . . . . ?
C5 C9 C10 C12 -123.22(19) . . . . ?
C8 C10 C12 C14 51.8(2) . . . . ?
C9 C10 C12 C14 174.82(19) . . . . ?
C8 C10 C12 C13 175.33(19) . . . . ?
C9 C10 C12 C13 -61.6(2) . . . . ?
O3 C1 O2 C4 179.25(19) . . . . ?
C2 C1 O2 C4 0.8(2) . . . . ?
O1 C4 O2 C1 -179.93(19) . . . . ?
C3 C4 O2 C1 -1.1(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.944
_diffrn_reflns_theta_full        28.31
_diffrn_measured_fraction_theta_full 0.944
_refine_diff_density_max         0.134
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.035
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_rtm3s
_database_code_depnum_ccdc_archive 'CCDC 1499426'
_audit_update_record             
;
2016-08-16 deposited with the CCDC.
2016-11-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'Bicyclo[2.2.2]oct-5-ene-2,3-dicarboxylic anhydride'
_chemical_name_common            ?
_chemical_melting_point          419.5
_chemical_formula_moiety         'C10 H10 O3'
_chemical_formula_sum            'C10 H10 O3'
_chemical_formula_weight         178.18

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   P2(1)/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.5300(15)
_cell_length_b                   10.411(2)
_cell_length_c                   12.121(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.062(4)
_cell_angle_gamma                90.00
_cell_volume                     817.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    203(2)
_cell_measurement_reflns_used    1511
_cell_measurement_theta_min      2.587
_cell_measurement_theta_max      27.694

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_F_000             376
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9768
_exptl_absorpt_correction_T_max  0.9862
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      203(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.34
_diffrn_reflns_number            3852
_diffrn_reflns_av_R_equivalents  0.0151
_diffrn_reflns_av_sigmaI/netI    0.0248
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.59
_diffrn_reflns_theta_max         28.26
_reflns_number_total             1998
_reflns_number_gt                1710
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2001)'
_computing_cell_refinement       'SAINTPlus, v. 6.2 (Bruker, 2001)'
_computing_data_reduction        'SAINTPlus, v. 6.2 (Bruker, 2001)'
_computing_structure_solution    'SHELXTL, v. 6.12 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL, v. 6.12 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL, v. 6.12 (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL, v. 6.12 (Sheldrick, 2008)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0673P)²+0.1915P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1998
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0466
_refine_ls_wR_factor_ref         0.1233
_refine_ls_wR_factor_gt          0.1180
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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
C1 C 0.3299(2) 0.03179(13) 0.70050(11) 0.0311(3) Uani 1 1 d . . .
C2 C 0.36961(19) 0.16869(11) 0.67033(10) 0.0255(3) Uani 1 1 d . . .
H2 H 0.4877 0.2040 0.7202 0.031 Uiso 1 1 calc R . .
C3 C 0.17070(19) 0.23980(12) 0.68720(10) 0.0260(3) Uani 1 1 d . . .
H3 H 0.1996 0.3073 0.7445 0.031 Uiso 1 1 calc R . .
C4 C 0.0341(2) 0.13794(13) 0.72698(11) 0.0315(3) Uani 1 1 d . . .
C5 C 0.0742(2) 0.29982(12) 0.57624(11) 0.0293(3) Uani 1 1 d . . .
H5 H -0.0586 0.3425 0.5843 0.035 Uiso 1 1 calc R . .
C6 C 0.2343(2) 0.39651(12) 0.54210(13) 0.0360(3) Uani 1 1 d . . .
H6A H 0.1790 0.4397 0.4729 0.043 Uiso 1 1 calc R . .
H6B H 0.2632 0.4619 0.6001 0.043 Uiso 1 1 calc R . .
C7 C 0.4348(2) 0.32499(13) 0.52531(13) 0.0360(3) Uani 1 1 d . . .
H7A H 0.5498 0.3594 0.5763 0.043 Uiso 1 1 calc R . .
H7B H 0.4662 0.3378 0.4491 0.043 Uiso 1 1 calc R . .
C8 C 0.4090(2) 0.18032(12) 0.54754(11) 0.0286(3) Uani 1 1 d . . .
H8 H 0.5329 0.1312 0.5332 0.034 Uiso 1 1 calc R . .
C9 C 0.2195(2) 0.13386(12) 0.47572(10) 0.0310(3) Uani 1 1 d . . .
H9 H 0.2231 0.0664 0.4244 0.037 Uiso 1 1 calc R . .
C10 C 0.0472(2) 0.19506(13) 0.49020(11) 0.0313(3) Uani 1 1 d . . .
H10 H -0.0813 0.1748 0.4501 0.038 Uiso 1 1 calc R . .
O1 O -0.13774(16) 0.14453(12) 0.74849(10) 0.0501(3) Uani 1 1 d . . .
O2 O 0.13717(16) 0.02078(9) 0.73637(8) 0.0370(3) Uani 1 1 d . . .
O3 O 0.43525(18) -0.06097(10) 0.69602(10) 0.0478(3) Uani 1 1 d . . .


_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
C1 O3 1.1907(17) . ?
C1 O2 1.3859(17) . ?
C1 C2 1.5018(18) . ?
C2 C3 1.5305(17) . ?
C2 C8 1.5459(17) . ?
C2 H2 0.9900 . ?
C3 C4 1.5027(18) . ?
C3 C5 1.5452(18) . ?
C3 H3 0.9900 . ?
C4 O1 1.1851(16) . ?
C4 O2 1.3909(17) . ?
C5 C10 1.5043(18) . ?
C5 C6 1.5440(19) . ?
C5 H5 0.9900 . ?
C6 C7 1.542(2) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C7 C8 1.5429(18) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C8 C9 1.5026(19) . ?
C8 H8 0.9900 . ?
C9 C10 1.3239(19) . ?
C9 H9 0.9400 . ?
C10 H10 0.9400 . ?

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
O3 C1 O2 119.94(13) . . ?
O3 C1 C2 129.84(13) . . ?
O2 C1 C2 110.21(11) . . ?
C1 C2 C3 104.58(10) . . ?
C1 C2 C8 111.28(10) . . ?
C3 C2 C8 109.58(10) . . ?
C1 C2 H2 110.4 . . ?
C3 C2 H2 110.4 . . ?
C8 C2 H2 110.4 . . ?
C4 C3 C2 104.38(10) . . ?
C4 C3 C5 111.72(11) . . ?
C2 C3 C5 109.96(10) . . ?
C4 C3 H3 110.2 . . ?
C2 C3 H3 110.2 . . ?
C5 C3 H3 110.2 . . ?
O1 C4 O2 119.64(13) . . ?
O1 C4 C3 130.18(13) . . ?
O2 C4 C3 110.18(11) . . ?
C10 C5 C6 108.21(11) . . ?
C10 C5 C3 108.11(10) . . ?
C6 C5 C3 106.25(11) . . ?
C10 C5 H5 111.4 . . ?
C6 C5 H5 111.4 . . ?
C3 C5 H5 111.4 . . ?
C7 C6 C5 109.55(10) . . ?
C7 C6 H6A 109.8 . . ?
C5 C6 H6A 109.8 . . ?
C7 C6 H6B 109.8 . . ?
C5 C6 H6B 109.8 . . ?
H6A C6 H6B 108.2 . . ?
C6 C7 C8 109.61(11) . . ?
C6 C7 H7A 109.7 . . ?
C8 C7 H7A 109.7 . . ?
C6 C7 H7B 109.7 . . ?
C8 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?
C9 C8 C7 108.23(11) . . ?
C9 C8 C2 108.05(10) . . ?
C7 C8 C2 106.22(11) . . ?
C9 C8 H8 111.4 . . ?
C7 C8 H8 111.4 . . ?
C2 C8 H8 111.4 . . ?
C10 C9 C8 114.92(12) . . ?
C10 C9 H9 122.5 . . ?
C8 C9 H9 122.5 . . ?
C9 C10 C5 114.30(12) . . ?
C9 C10 H10 122.8 . . ?
C5 C10 H10 122.8 . . ?
C1 O2 C4 110.52(10) . . ?

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 C1 C2 C3 176.31(15) . . . . ?
O2 C1 C2 C3 -2.60(14) . . . . ?
O3 C1 C2 C8 58.08(19) . . . . ?
O2 C1 C2 C8 -120.83(11) . . . . ?
C1 C2 C3 C4 0.64(13) . . . . ?
C8 C2 C3 C4 120.02(11) . . . . ?
C1 C2 C3 C5 -119.33(11) . . . . ?
C8 C2 C3 C5 0.05(13) . . . . ?
C2 C3 C4 O1 -177.67(14) . . . . ?
C5 C3 C4 O1 -58.89(19) . . . . ?
C2 C3 C4 O2 1.49(13) . . . . ?
C5 C3 C4 O2 120.27(11) . . . . ?
C4 C3 C5 C10 -61.02(13) . . . . ?
C2 C3 C5 C10 54.39(13) . . . . ?
C4 C3 C5 C6 -176.97(10) . . . . ?
C2 C3 C5 C6 -61.57(13) . . . . ?
C10 C5 C6 C7 -54.72(14) . . . . ?
C3 C5 C6 C7 61.17(14) . . . . ?
C5 C6 C7 C8 0.31(16) . . . . ?
C6 C7 C8 C9 54.03(15) . . . . ?
C6 C7 C8 C2 -61.79(14) . . . . ?
C1 C2 C8 C9 60.87(13) . . . . ?
C3 C2 C8 C9 -54.30(13) . . . . ?
C1 C2 C8 C7 176.81(11) . . . . ?
C3 C2 C8 C7 61.64(13) . . . . ?
C7 C8 C9 C10 -57.28(15) . . . . ?
C2 C8 C9 C10 57.34(14) . . . . ?
C8 C9 C10 C5 -0.04(17) . . . . ?
C6 C5 C10 C9 57.50(15) . . . . ?
C3 C5 C10 C9 -57.17(15) . . . . ?
O3 C1 O2 C4 -175.34(13) . . . . ?
C2 C1 O2 C4 3.69(14) . . . . ?
O1 C4 O2 C1 176.01(13) . . . . ?
C3 C4 O2 C1 -3.25(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        28.26
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.050
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_rtm4m
_database_code_depnum_ccdc_archive 'CCDC 1499427'
_audit_update_record             
;
2016-08-16 deposited with the CCDC.
2016-11-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'Bicyclo[2.2.2]octane-2-endo,3-endo-dicarboxylic acid anhydride'
_chemical_name_common            ?
_chemical_melting_point          463
_chemical_formula_moiety         '2(C10 H12 O3)'
_chemical_formula_sum            'C10 H12 O3'
_chemical_formula_weight         180.20

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   P2(1)/n

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                   14.472(3)
_cell_length_b                   8.1530(17)
_cell_length_c                   14.494(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.730(4)
_cell_angle_gamma                90.00
_cell_volume                     1709.4(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    203(2)
_cell_measurement_reflns_used    2857
_cell_measurement_theta_min      2.812
_cell_measurement_theta_max      26.649

_exptl_crystal_description       pyramid
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_F_000             768
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9797
_exptl_absorpt_correction_T_max  0.9857
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      203(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  'Bruker SMART-APEX area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.34
_diffrn_reflns_number            10819
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_av_sigmaI/netI    0.0263
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.02
_diffrn_reflns_theta_max         28.37
_reflns_number_total             4107
_reflns_number_gt                2984
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2001)'
_computing_cell_refinement       'SAINTPlus, v. 6.2 (Bruker, 2001)'
_computing_data_reduction        'SAINTPlus, v. 6.2 (Bruker, 2001)'
_computing_structure_solution    'SHELXTL, v. 6.12 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL, v. 6.12 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL, v. 6.12 (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL, v. 6.12 (Sheldrick, 2008)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0729P)²+0.1496P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4107
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0697
_refine_ls_R_factor_gt           0.0506
_refine_ls_wR_factor_ref         0.1359
_refine_ls_wR_factor_gt          0.1247
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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
C1 C 0.42443(14) 0.5023(2) 0.62478(12) 0.0561(4) Uani 1 1 d . . .
C2 C 0.37716(10) 0.36344(16) 0.67199(10) 0.0380(3) Uani 1 1 d . . .
H2 H 0.3604 0.3972 0.7342 0.046 Uiso 1 1 calc R . .
C3 C 0.45004(9) 0.22817(17) 0.67836(9) 0.0372(3) Uani 1 1 d . . .
H3 H 0.4623 0.1987 0.7431 0.045 Uiso 1 1 calc R . .
C4 C 0.53431(11) 0.3025(2) 0.63903(11) 0.0531(4) Uani 1 1 d . . .
C5 C 0.41585(10) 0.07715(17) 0.62416(11) 0.0422(3) Uani 1 1 d . . .
H5 H 0.4632 -0.0089 0.6265 0.051 Uiso 1 1 calc R . .
C6 C 0.32850(12) 0.0169(2) 0.66940(14) 0.0554(4) Uani 1 1 d . . .
H6A H 0.3430 -0.0155 0.7326 0.067 Uiso 1 1 calc R . .
H6B H 0.3045 -0.0783 0.6364 0.067 Uiso 1 1 calc R . .
C7 C 0.25549(10) 0.1523(2) 0.66835(12) 0.0524(4) Uani 1 1 d . . .
H7A H 0.1993 0.1132 0.6374 0.063 Uiso 1 1 calc R . .
H7B H 0.2409 0.1813 0.7312 0.063 Uiso 1 1 calc R . .
C8 C 0.29118(9) 0.30269(19) 0.61841(10) 0.0425(3) Uani 1 1 d . . .
H8 H 0.2438 0.3885 0.6163 0.051 Uiso 1 1 calc R . .
C9 C 0.31745(11) 0.2557(2) 0.52055(10) 0.0509(4) Uani 1 1 d . . .
H9A H 0.3387 0.3521 0.4882 0.061 Uiso 1 1 calc R . .
H9B H 0.2637 0.2127 0.4871 0.061 Uiso 1 1 calc R . .
C10 C 0.39416(11) 0.1259(2) 0.52421(11) 0.0505(4) Uani 1 1 d . . .
H10A H 0.3745 0.0300 0.4891 0.061 Uiso 1 1 calc R . .
H10B H 0.4493 0.1694 0.4967 0.061 Uiso 1 1 calc R . .
C11 C 0.37718(10) -0.02774(19) 0.07076(12) 0.0466(4) Uani 1 1 d . . .
C12 C 0.32906(9) 0.10796(15) 0.11993(10) 0.0361(3) Uani 1 1 d . . .
H12 H 0.2671 0.0718 0.1364 0.043 Uiso 1 1 calc R . .
C13 C 0.32120(9) 0.24669(17) 0.04874(9) 0.0365(3) Uani 1 1 d . . .
H13 H 0.2560 0.2732 0.0362 0.044 Uiso 1 1 calc R . .
C14 C 0.36256(10) 0.1773(2) -0.03596(10) 0.0483(4) Uani 1 1 d . . .
C15 C 0.37255(10) 0.39934(17) 0.08553(10) 0.0425(3) Uani 1 1 d . . .
H15 H 0.3688 0.4875 0.0396 0.051 Uiso 1 1 calc R . .
C16 C 0.32587(12) 0.45262(19) 0.17349(12) 0.0513(4) Uani 1 1 d . . .
H16A H 0.2619 0.4811 0.1594 0.062 Uiso 1 1 calc R . .
H16B H 0.3567 0.5490 0.1988 0.062 Uiso 1 1 calc R . .
C17 C 0.33000(11) 0.3135(2) 0.24477(10) 0.0478(4) Uani 1 1 d . . .
H17A H 0.3608 0.3518 0.3011 0.057 Uiso 1 1 calc R . .
H17B H 0.2678 0.2804 0.2595 0.057 Uiso 1 1 calc R . .
C18 C 0.38232(10) 0.16700(18) 0.20668(10) 0.0403(3) Uani 1 1 d . . .
H18 H 0.3861 0.0790 0.2527 0.048 Uiso 1 1 calc R . .
C19 C 0.47916(10) 0.22055(19) 0.18078(11) 0.0464(4) Uani 1 1 d . . .
H19A H 0.5126 0.1274 0.1569 0.056 Uiso 1 1 calc R . .
H19B H 0.5126 0.2605 0.2353 0.056 Uiso 1 1 calc R . .
C20 C 0.47357(10) 0.3567(2) 0.10739(12) 0.0489(4) Uani 1 1 d . . .
H20A H 0.5061 0.4533 0.1300 0.059 Uiso 1 1 calc R . .
H20B H 0.5029 0.3200 0.0517 0.059 Uiso 1 1 calc R . .
O1 O 0.60929(8) 0.2466(2) 0.63102(10) 0.0830(5) Uani 1 1 d . . .
O2 O 0.51568(9) 0.46091(16) 0.60927(9) 0.0672(4) Uani 1 1 d . . .
O3 O 0.39543(14) 0.63194(15) 0.60117(11) 0.0921(5) Uani 1 1 d . . .
O4 O 0.37065(9) 0.2377(2) -0.10982(8) 0.0783(4) Uani 1 1 d . . .
O5 O 0.39349(7) 0.01882(15) -0.01942(8) 0.0550(3) Uani 1 1 d . . .
O6 O 0.40108(10) -0.15933(14) 0.09741(11) 0.0733(4) Uani 1 1 d . . .


_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
C1 O3 1.184(2) . ?
C1 O2 1.388(2) . ?
C1 C2 1.499(2) . ?
C2 C3 1.5269(19) . ?
C2 C8 1.529(2) . ?
C2 H2 0.9800 . ?
C3 C4 1.490(2) . ?
C3 C5 1.534(2) . ?
C3 H3 0.9800 . ?
C4 O1 1.186(2) . ?
C4 O2 1.386(2) . ?
C5 C6 1.523(2) . ?
C5 C10 1.526(2) . ?
C5 H5 0.9800 . ?
C6 C7 1.528(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.522(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.528(2) . ?
C8 H8 0.9800 . ?
C9 C10 1.534(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 O6 1.188(2) . ?
C11 O5 1.388(2) . ?
C11 C12 1.499(2) . ?
C12 C18 1.5324(19) . ?
C12 C13 1.5329(19) . ?
C12 H12 0.9800 . ?
C13 C14 1.493(2) . ?
C13 C15 1.537(2) . ?
C13 H13 0.9800 . ?
C14 O4 1.1873(19) . ?
C14 O5 1.386(2) . ?
C15 C16 1.524(2) . ?
C15 C20 1.527(2) . ?
C15 H15 0.9800 . ?
C16 C17 1.534(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.526(2) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.526(2) . ?
C18 H18 0.9800 . ?
C19 C20 1.538(2) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?

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
O3 C1 O2 120.09(18) . . ?
O3 C1 C2 130.1(2) . . ?
O2 C1 C2 109.85(14) . . ?
C1 C2 C3 104.44(13) . . ?
C1 C2 C8 112.86(12) . . ?
C3 C2 C8 110.29(11) . . ?
C1 C2 H2 109.7 . . ?
C3 C2 H2 109.7 . . ?
C8 C2 H2 109.7 . . ?
C4 C3 C2 104.78(13) . . ?
C4 C3 C5 112.66(12) . . ?
C2 C3 C5 109.70(11) . . ?
C4 C3 H3 109.9 . . ?
C2 C3 H3 109.9 . . ?
C5 C3 H3 109.9 . . ?
O1 C4 O2 119.82(17) . . ?
O1 C4 C3 130.06(18) . . ?
O2 C4 C3 110.13(14) . . ?
C6 C5 C10 110.07(13) . . ?
C6 C5 C3 107.30(12) . . ?
C10 C5 C3 109.35(12) . . ?
C6 C5 H5 110.0 . . ?
C10 C5 H5 110.0 . . ?
C3 C5 H5 110.0 . . ?
C5 C6 C7 110.21(13) . . ?
C5 C6 H6A 109.6 . . ?
C7 C6 H6A 109.6 . . ?
C5 C6 H6B 109.6 . . ?
C7 C6 H6B 109.6 . . ?
H6A C6 H6B 108.1 . . ?
C8 C7 C6 110.01(12) . . ?
C8 C7 H7A 109.7 . . ?
C6 C7 H7A 109.7 . . ?
C8 C7 H7B 109.7 . . ?
C6 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?
C7 C8 C9 109.69(13) . . ?
C7 C8 C2 107.58(12) . . ?
C9 C8 C2 109.34(12) . . ?
C7 C8 H8 110.1 . . ?
C9 C8 H8 110.1 . . ?
C2 C8 H8 110.1 . . ?
C8 C9 C10 109.94(12) . . ?
C8 C9 H9A 109.7 . . ?
C10 C9 H9A 109.7 . . ?
C8 C9 H9B 109.7 . . ?
C10 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
C5 C10 C9 109.90(12) . . ?
C5 C10 H10A 109.7 . . ?
C9 C10 H10A 109.7 . . ?
C5 C10 H10B 109.7 . . ?
C9 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
O6 C11 O5 119.80(15) . . ?
O6 C11 C12 130.29(17) . . ?
O5 C11 C12 109.91(13) . . ?
C11 C12 C18 113.11(12) . . ?
C11 C12 C13 104.52(12) . . ?
C18 C12 C13 110.23(11) . . ?
C11 C12 H12 109.6 . . ?
C18 C12 H12 109.6 . . ?
C13 C12 H12 109.6 . . ?
C14 C13 C12 104.51(12) . . ?
C14 C13 C15 112.97(12) . . ?
C12 C13 C15 109.79(11) . . ?
C14 C13 H13 109.8 . . ?
C12 C13 H13 109.8 . . ?
C15 C13 H13 109.8 . . ?
O4 C14 O5 120.16(15) . . ?
O4 C14 C13 129.58(17) . . ?
O5 C14 C13 110.25(13) . . ?
C16 C15 C20 109.71(13) . . ?
C16 C15 C13 107.41(12) . . ?
C20 C15 C13 109.74(12) . . ?
C16 C15 H15 110.0 . . ?
C20 C15 H15 110.0 . . ?
C13 C15 H15 110.0 . . ?
C15 C16 C17 110.08(12) . . ?
C15 C16 H16A 109.6 . . ?
C17 C16 H16A 109.6 . . ?
C15 C16 H16B 109.6 . . ?
C17 C16 H16B 109.6 . . ?
H16A C16 H16B 108.2 . . ?
C18 C17 C16 110.15(12) . . ?
C18 C17 H17A 109.6 . . ?
C16 C17 H17A 109.6 . . ?
C18 C17 H17B 109.6 . . ?
C16 C17 H17B 109.6 . . ?
H17A C17 H17B 108.1 . . ?
C19 C18 C17 109.54(12) . . ?
C19 C18 C12 109.33(12) . . ?
C17 C18 C12 107.45(11) . . ?
C19 C18 H18 110.2 . . ?
C17 C18 H18 110.2 . . ?
C12 C18 H18 110.2 . . ?
C18 C19 C20 110.32(12) . . ?
C18 C19 H19A 109.6 . . ?
C20 C19 H19A 109.6 . . ?
C18 C19 H19B 109.6 . . ?
C20 C19 H19B 109.6 . . ?
H19A C19 H19B 108.1 . . ?
C15 C20 C19 109.75(12) . . ?
C15 C20 H20A 109.7 . . ?
C19 C20 H20A 109.7 . . ?
C15 C20 H20B 109.7 . . ?
C19 C20 H20B 109.7 . . ?
H20A C20 H20B 108.2 . . ?
C4 O2 C1 110.71(13) . . ?
C14 O5 C11 110.77(12) . . ?

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 C1 C2 C3 176.85(18) . . . . ?
O2 C1 C2 C3 -3.07(15) . . . . ?
O3 C1 C2 C8 57.0(2) . . . . ?
O2 C1 C2 C8 -122.89(14) . . . . ?
C1 C2 C3 C4 2.82(14) . . . . ?
C8 C2 C3 C4 124.35(12) . . . . ?
C1 C2 C3 C5 -118.35(13) . . . . ?
C8 C2 C3 C5 3.17(16) . . . . ?
C2 C3 C4 O1 178.10(17) . . . . ?
C5 C3 C4 O1 -62.7(2) . . . . ?
C2 C3 C4 O2 -1.76(15) . . . . ?
C5 C3 C4 O2 117.44(13) . . . . ?
C4 C3 C5 C6 -178.29(13) . . . . ?
C2 C3 C5 C6 -62.00(15) . . . . ?
C4 C3 C5 C10 -58.93(16) . . . . ?
C2 C3 C5 C10 57.36(15) . . . . ?
C10 C5 C6 C7 -60.17(17) . . . . ?
C3 C5 C6 C7 58.72(17) . . . . ?
C5 C6 C7 C8 2.6(2) . . . . ?
C6 C7 C8 C9 57.25(17) . . . . ?
C6 C7 C8 C2 -61.59(17) . . . . ?
C1 C2 C8 C7 174.56(13) . . . . ?
C3 C2 C8 C7 58.17(15) . . . . ?
C1 C2 C8 C9 55.50(17) . . . . ?
C3 C2 C8 C9 -60.89(15) . . . . ?
C7 C8 C9 C10 -60.82(16) . . . . ?
C2 C8 C9 C10 56.92(16) . . . . ?
C6 C5 C10 C9 56.40(16) . . . . ?
C3 C5 C10 C9 -61.24(15) . . . . ?
C8 C9 C10 C5 3.43(18) . . . . ?
O6 C11 C12 C18 58.1(2) . . . . ?
O5 C11 C12 C18 -121.94(13) . . . . ?
O6 C11 C12 C13 177.98(15) . . . . ?
O5 C11 C12 C13 -2.01(14) . . . . ?
C11 C12 C13 C14 1.76(13) . . . . ?
C18 C12 C13 C14 123.60(12) . . . . ?
C11 C12 C13 C15 -119.68(12) . . . . ?
C18 C12 C13 C15 2.16(15) . . . . ?
C12 C13 C14 O4 178.52(16) . . . . ?
C15 C13 C14 O4 -62.2(2) . . . . ?
C12 C13 C14 O5 -1.00(14) . . . . ?
C15 C13 C14 O5 118.31(13) . . . . ?
C14 C13 C15 C16 -177.73(12) . . . . ?
C12 C13 C15 C16 -61.51(14) . . . . ?
C14 C13 C15 C20 -58.52(16) . . . . ?
C12 C13 C15 C20 57.70(15) . . . . ?
C20 C15 C16 C17 -60.05(16) . . . . ?
C13 C15 C16 C17 59.18(16) . . . . ?
C15 C16 C17 C18 1.84(18) . . . . ?
C16 C17 C18 C19 57.51(16) . . . . ?
C16 C17 C18 C12 -61.16(15) . . . . ?
C11 C12 C18 C19 56.48(16) . . . . ?
C13 C12 C18 C19 -60.11(14) . . . . ?
C11 C12 C18 C17 175.29(12) . . . . ?
C13 C12 C18 C17 58.70(15) . . . . ?
C17 C18 C19 C20 -59.61(15) . . . . ?
C12 C18 C19 C20 57.89(15) . . . . ?
C16 C15 C20 C19 57.85(16) . . . . ?
C13 C15 C20 C19 -59.93(16) . . . . ?
C18 C19 C20 C15 1.71(17) . . . . ?
O1 C4 O2 C1 179.96(15) . . . . ?
C3 C4 O2 C1 -0.16(17) . . . . ?
O3 C1 O2 C4 -177.84(16) . . . . ?
C2 C1 O2 C4 2.10(17) . . . . ?
O4 C14 O5 C11 -179.83(14) . . . . ?
C13 C14 O5 C11 -0.25(15) . . . . ?
O6 C11 O5 C14 -178.52(13) . . . . ?
C12 C11 O5 C14 1.47(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.962
_diffrn_reflns_theta_full        28.37
_diffrn_measured_fraction_theta_full 0.962
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.050
