# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_DCM_0m
_database_code_depnum_ccdc_archive 'CCDC 1457371'
_audit_update_record             
;
2016-03-03 deposited with the CCDC.
2018-01-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H16 O3'
_chemical_formula_sum            'C14 H16 O3'
_chemical_formula_weight         232.27

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   21.1661(9)
_cell_length_b                   6.9223(3)
_cell_length_c                   23.4838(9)
_cell_angle_alpha                90
_cell_angle_beta                 91.652(2)
_cell_angle_gamma                90
_cell_volume                     3439.4(2)
_cell_formula_units_Z            12
_cell_measurement_temperature    373(2)
_cell_measurement_reflns_used    9891
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      31.44

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_F_000             1488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.490
_exptl_crystal_size_min          0.420
_exptl_absorpt_coefficient_mu    0.094
_shelx_estimated_absorpt_T_min   0.950
_shelx_estimated_absorpt_T_max   0.962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.950
_exptl_absorpt_correction_T_max  0.962
_exptl_absorpt_process_details   'bruker SADABS'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      373(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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            46855
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.735
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.970
_reflns_number_total             6049
_reflns_number_gt                5207
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0341P)²+2.8380P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6049
_refine_ls_number_parameters     463
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0641
_refine_ls_R_factor_gt           0.0528
_refine_ls_wR_factor_ref         0.1099
_refine_ls_wR_factor_gt          0.1050
_refine_ls_goodness_of_fit_ref   1.164
_refine_ls_restrained_S_all      1.164
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1A O 0.39529(6) 0.27498(19) 0.08330(5) 0.0131(3) Uani 1 1 d . . . . .
C2A C 0.35722(9) 0.3073(3) 0.03105(8) 0.0128(4) Uani 1 1 d . . . . .
C3A C 0.29878(9) 0.4224(3) 0.04662(8) 0.0155(4) Uani 1 1 d . . . . .
H3A1 H 0.2751 0.4550 0.0120 0.019 Uiso 1 1 calc R U . . .
H3A2 H 0.2720 0.3419 0.0696 0.019 Uiso 1 1 calc R U . . .
C4A C 0.31404(9) 0.6056(3) 0.07887(8) 0.0127(4) Uani 1 1 d . . . . .
C5A C 0.39549(9) 0.7732(3) 0.14006(8) 0.0144(4) Uani 1 1 d . . . . .
H5A H 0.3708 0.8843 0.1391 0.017 Uiso 1 1 calc R U . . .
C6A C 0.45244(9) 0.7722(3) 0.17026(8) 0.0144(4) Uani 1 1 d . . . . .
C7A C 0.48870(9) 0.6028(3) 0.17258(8) 0.0147(4) Uani 1 1 d . . . . .
H7A H 0.5266 0.6011 0.1936 0.018 Uiso 1 1 calc R U . . .
C8A C 0.46878(9) 0.4386(3) 0.14406(8) 0.0134(4) Uani 1 1 d . . . . .
H8A H 0.4931 0.3268 0.1461 0.016 Uiso 1 1 calc R U . . .
C9A C 0.41228(9) 0.4400(3) 0.11214(8) 0.0132(4) Uani 1 1 d . . . . .
C10A C 0.37483(9) 0.6077(3) 0.11086(8) 0.0124(4) Uani 1 1 d . . . . .
C11A C 0.39784(9) 0.4112(3) -0.01244(8) 0.0146(4) Uani 1 1 d . . . . .
H11A H 0.3723 0.4385 -0.0464 0.017 Uiso 1 1 calc R U . . .
H11B H 0.4122 0.5334 0.0034 0.017 Uiso 1 1 calc R U . . .
C12A C 0.45501(9) 0.2910(3) -0.02862(8) 0.0161(4) Uani 1 1 d . . . . .
H12A H 0.4789 0.3600 -0.0568 0.019 Uiso 1 1 calc R U . . .
H12B H 0.4823 0.2714 0.0048 0.019 Uiso 1 1 calc R U . . .
C13A C 0.43437(10) 0.0958(3) -0.05266(9) 0.0185(5) Uani 1 1 d . . . . .
H13B H 0.4099 0.1150 -0.0878 0.022 Uiso 1 1 calc R U . . .
H13A H 0.4714 0.0199 -0.0614 0.022 Uiso 1 1 calc R U . . .
C14A C 0.39465(9) -0.0134(3) -0.01022(9) 0.0182(5) Uani 1 1 d . . . . .
H14A H 0.4210 -0.0490 0.0226 0.022 Uiso 1 1 calc R U . . .
H14B H 0.3788 -0.1314 -0.0278 0.022 Uiso 1 1 calc R U . . .
C15A C 0.33878(9) 0.1075(3) 0.00958(9) 0.0157(4) Uani 1 1 d . . . . .
H15A H 0.3084 0.1213 -0.0219 0.019 Uiso 1 1 calc R U . . .
H15B H 0.3181 0.0386 0.0398 0.019 Uiso 1 1 calc R U . . .
O16A O 0.27713(6) 0.7422(2) 0.07926(6) 0.0155(3) Uani 1 1 d . . . . .
O17A O 0.47584(6) 0.9298(2) 0.19892(6) 0.0210(3) Uani 1 1 d . . . . .
H17A H 0.4472 1.0070 0.2041 0.031 Uiso 1 1 calc R U . . .
O1B O 0.27691(6) 0.65844(19) 0.24363(5) 0.0132(3) Uani 1 1 d . . . . .
C2B C 0.31553(9) 0.6008(3) 0.29370(8) 0.0127(4) Uani 1 1 d . . . . .
C3B C 0.36716(9) 0.4650(3) 0.27382(8) 0.0155(4) Uani 1 1 d . . . . .
H3B2 H 0.3966 0.5378 0.2513 0.019 Uiso 1 1 calc R U . . .
H3B1 H 0.3902 0.4149 0.3069 0.019 Uiso 1 1 calc R U . . .
C4B C 0.34207(9) 0.2982(3) 0.23888(8) 0.0120(4) Uani 1 1 d . . . . .
C5B C 0.24834(9) 0.1710(3) 0.18345(8) 0.0132(4) Uani 1 1 d . . . . .
H5B H 0.2664 0.0486 0.1836 0.016 Uiso 1 1 calc R U . . .
C6B C 0.19107(9) 0.2028(3) 0.15530(8) 0.0122(4) Uani 1 1 d . . . . .
C7B C 0.16656(9) 0.3913(3) 0.15226(8) 0.0140(4) Uani 1 1 d . . . . .
H7B H 0.1300 0.4150 0.1305 0.017 Uiso 1 1 calc R U . . .
C8B C 0.19600(9) 0.5425(3) 0.18117(8) 0.0145(4) Uani 1 1 d . . . . .
H8B H 0.1789 0.6662 0.1793 0.017 Uiso 1 1 calc R U . . .
C9B C 0.25113(9) 0.5081(3) 0.21300(8) 0.0116(4) Uani 1 1 d . . . . .
C10B C 0.27903(9) 0.3239(3) 0.21178(8) 0.0117(4) Uani 1 1 d . . . . .
C11B C 0.34310(9) 0.7886(3) 0.31747(9) 0.0164(4) Uani 1 1 d . . . . .
H11C H 0.3665 0.8526 0.2880 0.020 Uiso 1 1 calc R U . . .
H11D H 0.3725 0.7589 0.3487 0.020 Uiso 1 1 calc R U . . .
C12B C 0.29236(10) 0.9259(3) 0.33868(9) 0.0193(5) Uani 1 1 d . . . . .
H12C H 0.3126 1.0380 0.3560 0.023 Uiso 1 1 calc R U . . .
H12D H 0.2665 0.9700 0.3065 0.023 Uiso 1 1 calc R U . . .
C13B C 0.25014(10) 0.8299(3) 0.38201(9) 0.0222(5) Uani 1 1 d . . . . .
H13C H 0.2165 0.9178 0.3919 0.027 Uiso 1 1 calc R U . . .
H13D H 0.2748 0.8011 0.4164 0.027 Uiso 1 1 calc R U . . .
C14B C 0.22157(9) 0.6429(3) 0.35765(9) 0.0180(5) Uani 1 1 d . . . . .
H14C H 0.1973 0.5793 0.3866 0.022 Uiso 1 1 calc R U . . .
H14D H 0.1931 0.6736 0.3259 0.022 Uiso 1 1 calc R U . . .
C15B C 0.27306(9) 0.5064(3) 0.33762(8) 0.0146(4) Uani 1 1 d . . . . .
H15D H 0.2534 0.3923 0.3209 0.017 Uiso 1 1 calc R U . . .
H15C H 0.2989 0.4656 0.3702 0.017 Uiso 1 1 calc R U . . .
O16B O 0.37355(6) 0.1520(2) 0.23165(6) 0.0161(3) Uani 1 1 d . . . . .
O17B O 0.16031(6) 0.0489(2) 0.13137(6) 0.0164(3) Uani 1 1 d . . . . .
H17B H 0.1267 0.0850 0.1168 0.025 Uiso 1 1 calc R U . . .
O1C O 0.07147(6) 0.16364(19) 0.41158(5) 0.0129(3) Uani 1 1 d . . . . .
C2C C 0.03071(9) 0.2027(3) 0.36122(8) 0.0125(4) Uani 1 1 d . . . . .
C3C C -0.02614(9) 0.3155(3) 0.38106(8) 0.0140(4) Uani 1 1 d . . . . .
H3C1 H -0.0532 0.3469 0.3483 0.017 Uiso 1 1 calc R U . . .
H3C2 H -0.0502 0.2350 0.4064 0.017 Uiso 1 1 calc R U . . .
C4C C -0.00768(9) 0.4991(3) 0.41154(8) 0.0118(4) Uani 1 1 d . . . . .
C5C C 0.07767(9) 0.6595(3) 0.47082(8) 0.0133(4) Uani 1 1 d . . . . .
H5C H 0.0549 0.7743 0.4699 0.016 Uiso 1 1 calc R U . . .
C6C C 0.13432(9) 0.6487(3) 0.50127(8) 0.0141(4) Uani 1 1 d . . . . .
C7C C 0.16734(9) 0.4745(3) 0.50318(8) 0.0152(4) Uani 1 1 d . . . . .
H7C H 0.2048 0.4662 0.5248 0.018 Uiso 1 1 calc R U . . .
C8C C 0.14573(9) 0.3141(3) 0.47375(8) 0.0146(4) Uani 1 1 d . . . . .
H8C H 0.1685 0.1992 0.4755 0.017 Uiso 1 1 calc R U . . .
C9C C 0.08959(9) 0.3251(3) 0.44143(8) 0.0120(4) Uani 1 1 d . . . . .
C10C C 0.05458(9) 0.4971(3) 0.44130(8) 0.0128(4) Uani 1 1 d . . . . .
C11C C 0.06870(9) 0.3124(3) 0.31706(8) 0.0136(4) Uani 1 1 d . . . . .
H11F H 0.0413 0.3426 0.2844 0.016 Uiso 1 1 calc R U . . .
H11E H 0.0835 0.4333 0.3335 0.016 Uiso 1 1 calc R U . . .
C12C C 0.12534(9) 0.1960(3) 0.29717(8) 0.0173(4) Uani 1 1 d . . . . .
H12F H 0.1472 0.2684 0.2683 0.021 Uiso 1 1 calc R U . . .
H12E H 0.1547 0.1746 0.3291 0.021 Uiso 1 1 calc R U . . .
C13C C 0.10383(10) 0.0020(3) 0.27267(9) 0.0199(5) Uani 1 1 d . . . . .
H13F H 0.0776 0.0235 0.2387 0.024 Uiso 1 1 calc R U . . .
H13E H 0.1405 -0.0723 0.2619 0.024 Uiso 1 1 calc R U . . .
C14C C 0.06651(10) -0.1117(3) 0.31594(9) 0.0179(5) Uani 1 1 d . . . . .
H14F H 0.0945 -0.1482 0.3476 0.021 Uiso 1 1 calc R U . . .
H14E H 0.0505 -0.2292 0.2983 0.021 Uiso 1 1 calc R U . . .
C15C C 0.01130(9) 0.0048(3) 0.33836(8) 0.0150(4) Uani 1 1 d . . . . .
H15E H -0.0201 0.0217 0.3079 0.018 Uiso 1 1 calc R U . . .
H15F H -0.0082 -0.0677 0.3685 0.018 Uiso 1 1 calc R U . . .
O16C O -0.04321(6) 0.6398(2) 0.41290(5) 0.0140(3) Uani 1 1 d . . . . .
O17C O 0.15545(7) 0.8099(2) 0.52970(6) 0.0189(3) Uani 1 1 d . . . . .
H17C H 0.1884 0.7844 0.5474 0.028 Uiso 1 1 calc R U . . .


_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
O1A C9A 1.371(2) . ?
O1A C2A 1.466(2) . ?
C2A C15A 1.519(3) . ?
C2A C3A 1.525(3) . ?
C2A C11A 1.533(3) . ?
C3A C4A 1.507(3) . ?
C3A H3A1 0.9700 . ?
C3A H3A2 0.9700 . ?
C4A O16A 1.227(2) . ?
C4A C10A 1.471(3) . ?
C5A C6A 1.381(3) . ?
C5A C10A 1.399(3) . ?
C5A H5A 0.9300 . ?
C6A O17A 1.367(2) . ?
C6A C7A 1.402(3) . ?
C7A C8A 1.379(3) . ?
C7A H7A 0.9300 . ?
C8A C9A 1.393(3) . ?
C8A H8A 0.9300 . ?
C9A C10A 1.405(3) . ?
C11A C12A 1.526(3) . ?
C11A H11A 0.9700 . ?
C11A H11B 0.9700 . ?
C12A C13A 1.523(3) . ?
C12A H12A 0.9700 . ?
C12A H12B 0.9700 . ?
C13A C14A 1.523(3) . ?
C13A H13B 0.9700 . ?
C13A H13A 0.9700 . ?
C14A C15A 1.532(3) . ?
C14A H14A 0.9700 . ?
C14A H14B 0.9700 . ?
C15A H15A 0.9700 . ?
C15A H15B 0.9700 . ?
O17A H17A 0.8200 . ?
O1B C9B 1.370(2) . ?
O1B C2B 1.468(2) . ?
C2B C11B 1.525(3) . ?
C2B C3B 1.525(3) . ?
C2B C15B 1.534(3) . ?
C3B C4B 1.504(3) . ?
C3B H3B2 0.9700 . ?
C3B H3B1 0.9700 . ?
C4B O16B 1.226(2) . ?
C4B C10B 1.472(3) . ?
C5B C6B 1.382(3) . ?
C5B C10B 1.400(3) . ?
C5B H5B 0.9300 . ?
C6B O17B 1.361(2) . ?
C6B C7B 1.405(3) . ?
C7B C8B 1.386(3) . ?
C7B H7B 0.9300 . ?
C8B C9B 1.388(3) . ?
C8B H8B 0.9300 . ?
C9B C10B 1.405(3) . ?
C11B C12B 1.528(3) . ?
C11B H11C 0.9700 . ?
C11B H11D 0.9700 . ?
C12B C13B 1.526(3) . ?
C12B H12C 0.9700 . ?
C12B H12D 0.9700 . ?
C13B C14B 1.532(3) . ?
C13B H13C 0.9700 . ?
C13B H13D 0.9700 . ?
C14B C15B 1.527(3) . ?
C14B H14C 0.9700 . ?
C14B H14D 0.9700 . ?
C15B H15D 0.9700 . ?
C15B H15C 0.9700 . ?
O17B H17B 0.8200 . ?
O1C C9C 1.368(2) . ?
O1C C2C 1.469(2) . ?
C2C C3C 1.519(3) . ?
C2C C15C 1.524(3) . ?
C2C C11C 1.532(3) . ?
C3C C4C 1.505(3) . ?
C3C H3C1 0.9700 . ?
C3C H3C2 0.9700 . ?
C4C O16C 1.231(2) . ?
C4C C10C 1.474(3) . ?
C5C C6C 1.380(3) . ?
C5C C10C 1.402(3) . ?
C5C H5C 0.9300 . ?
C6C O17C 1.369(2) . ?
C6C C7C 1.394(3) . ?
C7C C8C 1.379(3) . ?
C7C H7C 0.9300 . ?
C8C C9C 1.394(3) . ?
C8C H8C 0.9300 . ?
C9C C10C 1.402(3) . ?
C11C C12C 1.529(3) . ?
C11C H11F 0.9700 . ?
C11C H11E 0.9700 . ?
C12C C13C 1.525(3) . ?
C12C H12F 0.9700 . ?
C12C H12E 0.9700 . ?
C13C C14C 1.524(3) . ?
C13C H13F 0.9700 . ?
C13C H13E 0.9700 . ?
C14C C15C 1.526(3) . ?
C14C H14F 0.9700 . ?
C14C H14E 0.9700 . ?
C15C H15E 0.9700 . ?
C15C H15F 0.9700 . ?
O17C H17C 0.8200 . ?

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
C9A O1A C2A 114.60(14) . . ?
O1A C2A C15A 105.57(15) . . ?
O1A C2A C3A 108.02(15) . . ?
C15A C2A C3A 110.66(16) . . ?
O1A C2A C11A 108.91(14) . . ?
C15A C2A C11A 110.46(16) . . ?
C3A C2A C11A 112.91(16) . . ?
C4A C3A C2A 113.36(16) . . ?
C4A C3A H3A1 108.9 . . ?
C2A C3A H3A1 108.9 . . ?
C4A C3A H3A2 108.9 . . ?
C2A C3A H3A2 108.9 . . ?
H3A1 C3A H3A2 107.7 . . ?
O16A C4A C10A 122.43(18) . . ?
O16A C4A C3A 121.67(17) . . ?
C10A C4A C3A 115.88(17) . . ?
C6A C5A C10A 120.25(19) . . ?
C6A C5A H5A 119.9 . . ?
C10A C5A H5A 119.9 . . ?
O17A C6A C5A 123.20(18) . . ?
O17A C6A C7A 117.27(16) . . ?
C5A C6A C7A 119.53(19) . . ?
C8A C7A C6A 120.74(17) . . ?
C8A C7A H7A 119.6 . . ?
C6A C7A H7A 119.6 . . ?
C7A C8A C9A 120.09(19) . . ?
C7A C8A H8A 120.0 . . ?
C9A C8A H8A 120.0 . . ?
O1A C9A C8A 117.96(18) . . ?
O1A C9A C10A 122.54(16) . . ?
C8A C9A C10A 119.50(18) . . ?
C5A C10A C9A 119.84(17) . . ?
C5A C10A C4A 120.99(18) . . ?
C9A C10A C4A 119.17(18) . . ?
C12A C11A C2A 111.98(16) . . ?
C12A C11A H11A 109.2 . . ?
C2A C11A H11A 109.2 . . ?
C12A C11A H11B 109.2 . . ?
C2A C11A H11B 109.2 . . ?
H11A C11A H11B 107.9 . . ?
C13A C12A C11A 110.79(16) . . ?
C13A C12A H12A 109.5 . . ?
C11A C12A H12A 109.5 . . ?
C13A C12A H12B 109.5 . . ?
C11A C12A H12B 109.5 . . ?
H12A C12A H12B 108.1 . . ?
C14A C13A C12A 110.83(17) . . ?
C14A C13A H13B 109.5 . . ?
C12A C13A H13B 109.5 . . ?
C14A C13A H13A 109.5 . . ?
C12A C13A H13A 109.5 . . ?
H13B C13A H13A 108.1 . . ?
C13A C14A C15A 111.88(17) . . ?
C13A C14A H14A 109.2 . . ?
C15A C14A H14A 109.2 . . ?
C13A C14A H14B 109.2 . . ?
C15A C14A H14B 109.2 . . ?
H14A C14A H14B 107.9 . . ?
C2A C15A C14A 113.90(16) . . ?
C2A C15A H15A 108.8 . . ?
C14A C15A H15A 108.8 . . ?
C2A C15A H15B 108.8 . . ?
C14A C15A H15B 108.8 . . ?
H15A C15A H15B 107.7 . . ?
C6A O17A H17A 109.5 . . ?
C9B O1B C2B 114.72(14) . . ?
O1B C2B C11B 105.06(15) . . ?
O1B C2B C3B 108.06(15) . . ?
C11B C2B C3B 111.57(16) . . ?
O1B C2B C15B 109.32(15) . . ?
C11B C2B C15B 110.03(16) . . ?
C3B C2B C15B 112.49(16) . . ?
C4B C3B C2B 113.28(16) . . ?
C4B C3B H3B2 108.9 . . ?
C2B C3B H3B2 108.9 . . ?
C4B C3B H3B1 108.9 . . ?
C2B C3B H3B1 108.9 . . ?
H3B2 C3B H3B1 107.7 . . ?
O16B C4B C10B 121.96(18) . . ?
O16B C4B C3B 121.61(17) . . ?
C10B C4B C3B 116.37(17) . . ?
C6B C5B C10B 119.70(18) . . ?
C6B C5B H5B 120.1 . . ?
C10B C5B H5B 120.1 . . ?
O17B C6B C5B 118.37(18) . . ?
O17B C6B C7B 122.29(16) . . ?
C5B C6B C7B 119.33(18) . . ?
C8B C7B C6B 121.08(17) . . ?
C8B C7B H7B 119.5 . . ?
C6B C7B H7B 119.5 . . ?
C7B C8B C9B 119.56(19) . . ?
C7B C8B H8B 120.2 . . ?
C9B C8B H8B 120.2 . . ?
O1B C9B C8B 117.92(17) . . ?
O1B C9B C10B 122.59(16) . . ?
C8B C9B C10B 119.47(18) . . ?
C5B C10B C9B 120.40(17) . . ?
C5B C10B C4B 121.07(18) . . ?
C9B C10B C4B 118.49(17) . . ?
C2B C11B C12B 112.61(16) . . ?
C2B C11B H11C 109.1 . . ?
C12B C11B H11C 109.1 . . ?
C2B C11B H11D 109.1 . . ?
C12B C11B H11D 109.1 . . ?
H11C C11B H11D 107.8 . . ?
C13B C12B C11B 112.16(17) . . ?
C13B C12B H12C 109.2 . . ?
C11B C12B H12C 109.2 . . ?
C13B C12B H12D 109.2 . . ?
C11B C12B H12D 109.2 . . ?
H12C C12B H12D 107.9 . . ?
C12B C13B C14B 110.57(17) . . ?
C12B C13B H13C 109.5 . . ?
C14B C13B H13C 109.5 . . ?
C12B C13B H13D 109.5 . . ?
C14B C13B H13D 109.5 . . ?
H13C C13B H13D 108.1 . . ?
C15B C14B C13B 111.11(17) . . ?
C15B C14B H14C 109.4 . . ?
C13B C14B H14C 109.4 . . ?
C15B C14B H14D 109.4 . . ?
C13B C14B H14D 109.4 . . ?
H14C C14B H14D 108.0 . . ?
C14B C15B C2B 112.40(17) . . ?
C14B C15B H15D 109.1 . . ?
C2B C15B H15D 109.1 . . ?
C14B C15B H15C 109.1 . . ?
C2B C15B H15C 109.1 . . ?
H15D C15B H15C 107.9 . . ?
C6B O17B H17B 109.5 . . ?
C9C O1C C2C 114.29(14) . . ?
O1C C2C C3C 107.45(15) . . ?
O1C C2C C15C 105.32(15) . . ?
C3C C2C C15C 111.23(16) . . ?
O1C C2C C11C 109.20(15) . . ?
C3C C2C C11C 112.90(16) . . ?
C15C C2C C11C 110.39(16) . . ?
C4C C3C C2C 112.51(16) . . ?
C4C C3C H3C1 109.1 . . ?
C2C C3C H3C1 109.1 . . ?
C4C C3C H3C2 109.1 . . ?
C2C C3C H3C2 109.1 . . ?
H3C1 C3C H3C2 107.8 . . ?
O16C C4C C10C 122.26(18) . . ?
O16C C4C C3C 122.00(16) . . ?
C10C C4C C3C 115.70(17) . . ?
C6C C5C C10C 119.88(19) . . ?
C6C C5C H5C 120.1 . . ?
C10C C5C H5C 120.1 . . ?
O17C C6C C5C 118.39(18) . . ?
O17C C6C C7C 122.22(17) . . ?
C5C C6C C7C 119.38(18) . . ?
C8C C7C C6C 121.46(17) . . ?
C8C C7C H7C 119.3 . . ?
C6C C7C H7C 119.3 . . ?
C7C C8C C9C 119.62(19) . . ?
C7C C8C H8C 120.2 . . ?
C9C C8C H8C 120.2 . . ?
O1C C9C C8C 117.15(17) . . ?
O1C C9C C10C 123.51(16) . . ?
C8C C9C C10C 119.34(18) . . ?
C5C C10C C9C 120.22(17) . . ?
C5C C10C C4C 121.40(18) . . ?
C9C C10C C4C 118.33(17) . . ?
C12C C11C C2C 112.18(16) . . ?
C12C C11C H11F 109.2 . . ?
C2C C11C H11F 109.2 . . ?
C12C C11C H11E 109.2 . . ?
C2C C11C H11E 109.2 . . ?
H11F C11C H11E 107.9 . . ?
C13C C12C C11C 110.56(17) . . ?
C13C C12C H12F 109.5 . . ?
C11C C12C H12F 109.5 . . ?
C13C C12C H12E 109.5 . . ?
C11C C12C H12E 109.5 . . ?
H12F C12C H12E 108.1 . . ?
C14C C13C C12C 110.99(17) . . ?
C14C C13C H13F 109.4 . . ?
C12C C13C H13F 109.4 . . ?
C14C C13C H13E 109.4 . . ?
C12C C13C H13E 109.4 . . ?
H13F C13C H13E 108.0 . . ?
C13C C14C C15C 111.93(17) . . ?
C13C C14C H14F 109.2 . . ?
C15C C14C H14F 109.2 . . ?
C13C C14C H14E 109.2 . . ?
C15C C14C H14E 109.2 . . ?
H14F C14C H14E 107.9 . . ?
C2C C15C C14C 113.30(16) . . ?
C2C C15C H15E 108.9 . . ?
C14C C15C H15E 108.9 . . ?
C2C C15C H15F 108.9 . . ?
C14C C15C H15F 108.9 . . ?
H15E C15C H15F 107.7 . . ?
C6C O17C H17C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9A O1A C2A C15A -174.71(15) . . . . ?
C9A O1A C2A C3A -56.3(2) . . . . ?
C9A O1A C2A C11A 66.7(2) . . . . ?
O1A C2A C3A C4A 53.5(2) . . . . ?
C15A C2A C3A C4A 168.59(16) . . . . ?
C11A C2A C3A C4A -67.0(2) . . . . ?
C2A C3A C4A O16A 156.70(18) . . . . ?
C2A C3A C4A C10A -24.9(2) . . . . ?
C10A C5A C6A O17A 178.89(18) . . . . ?
C10A C5A C6A C7A -1.5(3) . . . . ?
O17A C6A C7A C8A -178.99(17) . . . . ?
C5A C6A C7A C8A 1.4(3) . . . . ?
C6A C7A C8A C9A 0.5(3) . . . . ?
C2A O1A C9A C8A -150.52(17) . . . . ?
C2A O1A C9A C10A 29.9(2) . . . . ?
C7A C8A C9A O1A 178.27(17) . . . . ?
C7A C8A C9A C10A -2.2(3) . . . . ?
C6A C5A C10A C9A -0.2(3) . . . . ?
C6A C5A C10A C4A 179.48(18) . . . . ?
O1A C9A C10A C5A -178.42(17) . . . . ?
C8A C9A C10A C5A 2.0(3) . . . . ?
O1A C9A C10A C4A 1.9(3) . . . . ?
C8A C9A C10A C4A -177.64(17) . . . . ?
O16A C4A C10A C5A -4.8(3) . . . . ?
C3A C4A C10A C5A 176.78(17) . . . . ?
O16A C4A C10A C9A 174.82(18) . . . . ?
C3A C4A C10A C9A -3.6(3) . . . . ?
O1A C2A C11A C12A 61.6(2) . . . . ?
C15A C2A C11A C12A -53.9(2) . . . . ?
C3A C2A C11A C12A -178.40(16) . . . . ?
C2A C11A C12A C13A 57.8(2) . . . . ?
C11A C12A C13A C14A -57.1(2) . . . . ?
C12A C13A C14A C15A 53.6(2) . . . . ?
O1A C2A C15A C14A -66.7(2) . . . . ?
C3A C2A C15A C14A 176.69(16) . . . . ?
C11A C2A C15A C14A 50.9(2) . . . . ?
C13A C14A C15A C2A -51.6(2) . . . . ?
C9B O1B C2B C11B 175.40(15) . . . . ?
C9B O1B C2B C3B 56.2(2) . . . . ?
C9B O1B C2B C15B -66.5(2) . . . . ?
O1B C2B C3B C4B -52.6(2) . . . . ?
C11B C2B C3B C4B -167.61(16) . . . . ?
C15B C2B C3B C4B 68.2(2) . . . . ?
C2B C3B C4B O16B -161.32(17) . . . . ?
C2B C3B C4B C10B 21.4(2) . . . . ?
C10B C5B C6B O17B -175.69(17) . . . . ?
C10B C5B C6B C7B 4.3(3) . . . . ?
O17B C6B C7B C8B 174.28(17) . . . . ?
C5B C6B C7B C8B -5.7(3) . . . . ?
C6B C7B C8B C9B 1.0(3) . . . . ?
C2B O1B C9B C8B 154.15(17) . . . . ?
C2B O1B C9B C10B -27.3(2) . . . . ?
C7B C8B C9B O1B -176.31(17) . . . . ?
C7B C8B C9B C10B 5.1(3) . . . . ?
C6B C5B C10B C9B 1.7(3) . . . . ?
C6B C5B C10B C4B -175.82(17) . . . . ?
O1B C9B C10B C5B 175.00(17) . . . . ?
C8B C9B C10B C5B -6.4(3) . . . . ?
O1B C9B C10B C4B -7.4(3) . . . . ?
C8B C9B C10B C4B 171.14(17) . . . . ?
O16B C4B C10B C5B 9.6(3) . . . . ?
C3B C4B C10B C5B -173.10(17) . . . . ?
O16B C4B C10B C9B -167.94(18) . . . . ?
C3B C4B C10B C9B 9.3(3) . . . . ?
O1B C2B C11B C12B 64.2(2) . . . . ?
C3B C2B C11B C12B -178.99(16) . . . . ?
C15B C2B C11B C12B -53.4(2) . . . . ?
C2B C11B C12B C13B 54.4(2) . . . . ?
C11B C12B C13B C14B -54.3(2) . . . . ?
C12B C13B C14B C15B 55.1(2) . . . . ?
C13B C14B C15B C2B -56.3(2) . . . . ?
O1B C2B C15B C14B -60.2(2) . . . . ?
C11B C2B C15B C14B 54.7(2) . . . . ?
C3B C2B C15B C14B 179.76(16) . . . . ?
C9C O1C C2C C3C -55.90(19) . . . . ?
C9C O1C C2C C15C -174.57(15) . . . . ?
C9C O1C C2C C11C 66.88(19) . . . . ?
O1C C2C C3C C4C 57.0(2) . . . . ?
C15C C2C C3C C4C 171.74(15) . . . . ?
C11C C2C C3C C4C -63.5(2) . . . . ?
C2C C3C C4C O16C 153.56(17) . . . . ?
C2C C3C C4C C10C -28.6(2) . . . . ?
C10C C5C C6C O17C -179.87(17) . . . . ?
C10C C5C C6C C7C -1.3(3) . . . . ?
O17C C6C C7C C8C -179.26(18) . . . . ?
C5C C6C C7C C8C 2.2(3) . . . . ?
C6C C7C C8C C9C -0.2(3) . . . . ?
C2C O1C C9C C8C -154.61(16) . . . . ?
C2C O1C C9C C10C 25.9(2) . . . . ?
C7C C8C C9C O1C 177.86(17) . . . . ?
C7C C8C C9C C10C -2.7(3) . . . . ?
C6C C5C C10C C9C -1.6(3) . . . . ?
C6C C5C C10C C4C 175.85(18) . . . . ?
O1C C9C C10C C5C -177.00(17) . . . . ?
C8C C9C C10C C5C 3.6(3) . . . . ?
O1C C9C C10C C4C 5.5(3) . . . . ?
C8C C9C C10C C4C -173.95(17) . . . . ?
O16C C4C C10C C5C -2.8(3) . . . . ?
C3C C4C C10C C5C 179.33(17) . . . . ?
O16C C4C C10C C9C 174.69(17) . . . . ?
C3C C4C C10C C9C -3.2(3) . . . . ?
O1C C2C C11C C12C 61.1(2) . . . . ?
C3C C2C C11C C12C -179.45(16) . . . . ?
C15C C2C C11C C12C -54.2(2) . . . . ?
C2C C11C C12C C13C 57.2(2) . . . . ?
C11C C12C C13C C14C -56.4(2) . . . . ?
C12C C13C C14C C15C 54.2(2) . . . . ?
O1C C2C C15C C14C -65.9(2) . . . . ?
C3C C2C C15C C14C 178.01(16) . . . . ?
C11C C2C C15C C14C 51.9(2) . . . . ?
C13C C14C C15C C2C -52.6(2) . . . . ?

_refine_diff_density_max         0.252
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.048

_shelxl_version_number           2013-3


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method 
'Ethyl acetate - light petroleum ether'
####################################################################### 
# 
# 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_mt_101_3
_database_code_depnum_ccdc_archive 'CCDC 1572104'
_audit_update_record             
;
2017-09-01 deposited with the CCDC.
2018-01-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '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                   7.9634(4)
_cell_length_b                   10.2991(5)
_cell_length_c                   11.6563(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.605(4)
_cell_angle_gamma                90.00
_cell_volume                     955.63(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2171
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      27.35

_exptl_crystal_description       PRISMATIC
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9604
_exptl_absorpt_correction_T_max  0.9887
_exptl_absorpt_process_details   'BRUKER (SADABS, 2006)'

_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6803
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_sigmaI/netI    0.0303
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.64
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1679
_reflns_number_gt                1406
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0419P)²+0.4981P] where P=(Fo²+2Fc²)/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         1679
_refine_ls_number_parameters     121
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0739
_refine_ls_R_factor_gt           0.0593
_refine_ls_wR_factor_ref         0.1200
_refine_ls_wR_factor_gt          0.1145
_refine_ls_goodness_of_fit_ref   1.169
_refine_ls_restrained_S_all      1.169
_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 0.0799(2) 1.15478(15) 0.20064(13) 0.0320(4) Uani 1 1 d . . .
O2 O 0.22021(19) 0.83419(14) 0.01493(13) 0.0285(4) Uani 1 1 d . . .
O3 O 0.3763(2) 1.33306(14) -0.11921(13) 0.0333(4) Uani 1 1 d . . .
H3' H 0.4431 1.3341 -0.1738 0.050 Uiso 1 1 calc R . .
C1 C 0.2145(2) 1.0618(2) 0.04534(17) 0.0197(5) Uani 1 1 d . . .
C2 C 0.2624(2) 0.9552(2) -0.02146(17) 0.0205(5) Uani 1 1 d . . .
C3 C 0.3505(2) 0.9772(2) -0.12197(18) 0.0237(5) Uani 1 1 d . . .
H3 H 0.3832 0.9057 -0.1676 0.028 Uiso 1 1 calc R . .
C4 C 0.3901(3) 1.1015(2) -0.15528(18) 0.0242(5) Uani 1 1 d . . .
H4 H 0.4509 1.1148 -0.2232 0.029 Uiso 1 1 calc R . .
C5 C 0.3419(3) 1.2075(2) -0.09043(18) 0.0225(5) Uani 1 1 d . . .
C6 C 0.2548(2) 1.1865(2) 0.00874(17) 0.0207(5) Uani 1 1 d . . .
H6 H 0.2214 1.2589 0.0531 0.025 Uiso 1 1 calc R . .
C7 C 0.1243(2) 1.0526(2) 0.15540(18) 0.0213(5) Uani 1 1 d . . .
C8 C 0.0897(3) 0.9264(2) 0.21302(19) 0.0303(6) Uani 1 1 d . . .
H8C H 0.0397 0.9428 0.2875 0.045 Uiso 1 1 calc R . .
H8A H 0.1950 0.8784 0.2245 0.045 Uiso 1 1 calc R . .
H8B H 0.0116 0.8752 0.1649 0.045 Uiso 1 1 calc R . .
C9 C 0.2652(3) 0.7237(2) -0.0529(2) 0.0295(6) Uani 1 1 d . . .
H9A H 0.3889 0.7150 -0.0550 0.035 Uiso 1 1 calc R . .
H9B H 0.2202 0.7330 -0.1325 0.035 Uiso 1 1 calc R . .
C10 C 0.1902(3) 0.6080(2) 0.0034(3) 0.0445(7) Uani 1 1 d . . .
H10B H 0.2340 0.6013 0.0826 0.067 Uiso 1 1 calc R . .
H10A H 0.2195 0.5294 -0.0390 0.067 Uiso 1 1 calc R . .
H10C H 0.0677 0.6173 0.0036 0.067 Uiso 1 1 calc R . .


_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 C7 1.233(2) . ?
O2 C2 1.362(3) . ?
O2 C9 1.437(3) . ?
O3 C5 1.365(3) . ?
O3 H3' 0.8400 . ?
C1 C6 1.393(3) . ?
C1 C2 1.405(3) . ?
C1 C7 1.491(3) . ?
C2 C3 1.400(3) . ?
C3 C4 1.377(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.388(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.382(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.492(3) . ?
C8 H8C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C9 C10 1.493(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10B 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O2 C9 119.09(17) . . ?
C5 O3 H3' 109.5 . . ?
C6 C1 C2 118.81(19) . . ?
C6 C1 C7 116.26(18) . . ?
C2 C1 C7 124.93(19) . . ?
O2 C2 C3 122.83(18) . . ?
O2 C2 C1 117.99(18) . . ?
C3 C2 C1 119.18(19) . . ?
C4 C3 C2 120.68(19) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 120.6(2) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
O3 C5 C6 117.60(18) . . ?
O3 C5 C4 123.39(19) . . ?
C6 C5 C4 119.0(2) . . ?
C5 C6 C1 121.74(19) . . ?
C5 C6 H6 119.1 . . ?
C1 C6 H6 119.1 . . ?
O1 C7 C1 117.70(19) . . ?
O1 C7 C8 119.47(19) . . ?
C1 C7 C8 122.81(19) . . ?
C7 C8 H8C 109.5 . . ?
C7 C8 H8A 109.5 . . ?
H8C C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8C C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O2 C9 C10 106.34(19) . . ?
O2 C9 H9A 110.5 . . ?
C10 C9 H9A 110.5 . . ?
O2 C9 H9B 110.5 . . ?
C10 C9 H9B 110.5 . . ?
H9A C9 H9B 108.7 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10A 109.5 . . ?
H10B C10 H10A 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 O2 C2 C3 -0.9(3) . . . . ?
C9 O2 C2 C1 178.96(18) . . . . ?
C6 C1 C2 O2 -179.21(17) . . . . ?
C7 C1 C2 O2 1.7(3) . . . . ?
C6 C1 C2 C3 0.6(3) . . . . ?
C7 C1 C2 C3 -178.46(18) . . . . ?
O2 C2 C3 C4 179.91(18) . . . . ?
C1 C2 C3 C4 0.1(3) . . . . ?
C2 C3 C4 C5 -0.7(3) . . . . ?
C3 C4 C5 O3 -179.57(19) . . . . ?
C3 C4 C5 C6 0.6(3) . . . . ?
O3 C5 C6 C1 -179.71(19) . . . . ?
C4 C5 C6 C1 0.2(3) . . . . ?
C2 C1 C6 C5 -0.8(3) . . . . ?
C7 C1 C6 C5 178.42(18) . . . . ?
C6 C1 C7 O1 5.8(3) . . . . ?
C2 C1 C7 O1 -175.03(19) . . . . ?
C6 C1 C7 C8 -172.82(19) . . . . ?
C2 C1 C7 C8 6.3(3) . . . . ?
C2 O2 C9 C10 -175.36(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.046
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane-methanol'
