# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2014

####################################################################### 
# 
# 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_cd214432
_database_code_depnum_ccdc_archive 'CCDC 1035334'
_audit_update_record             
;
2014-11-20 deposited with the CCDC.
2014-12-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H16 O4'
_chemical_formula_weight         260.28

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   8.153(9)
_cell_length_b                   8.436(8)
_cell_length_c                   10.959(10)
_cell_angle_alpha                86.72(3)
_cell_angle_beta                 72.91(2)
_cell_angle_gamma                72.86(2)
_cell_volume                     688.1(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    630
_cell_measurement_theta_min      5.056
_cell_measurement_theta_max      45.384

_exptl_crystal_description       prismatic
_exptl_crystal_colour            cololress
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_F_000             276
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.112
_exptl_absorpt_coefficient_mu    0.091
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6689
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4021
_diffrn_reflns_av_unetI/netI     0.0540
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.945
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             2687
_reflns_number_gt                1312
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_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)+(0.0605P)²] 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         2687
_refine_ls_number_parameters     176
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1073
_refine_ls_R_factor_gt           0.0468
_refine_ls_wR_factor_ref         0.1336
_refine_ls_wR_factor_gt          0.1120
_refine_ls_goodness_of_fit_ref   0.898
_refine_ls_restrained_S_all      0.898
_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
O1 O -0.3892(2) 0.6853(3) 1.21325(18) 0.1142(7) Uani 1 1 d . . . . .
O2 O -0.29522(18) 0.7917(2) 1.02913(16) 0.0753(5) Uani 1 1 d . . . . .
O3 O 0.2567(2) 0.8959(2) 0.84896(15) 0.0866(5) Uani 1 1 d . . . . .
O4 O 0.14581(17) 0.78871(17) 0.71767(13) 0.0649(4) Uani 1 1 d . . . . .
C1 C -0.2621(3) 0.7104(3) 1.1342(2) 0.0762(7) Uani 1 1 d . . . . .
C2 C -0.0783(3) 0.6635(3) 1.1415(2) 0.0642(6) Uani 1 1 d . . . . .
C3 C -0.0399(4) 0.5780(3) 1.2470(2) 0.0775(7) Uani 1 1 d . . . . .
H3 H -0.1309 0.5511 1.3107 0.093 Uiso 1 1 calc R U . . .
C4 C 0.1300(4) 0.5335(3) 1.2575(3) 0.0858(8) Uani 1 1 d . . . . .
H4 H 0.1548 0.4760 1.3280 0.103 Uiso 1 1 calc R U . . .
C5 C 0.2642(3) 0.5733(3) 1.1646(3) 0.0870(8) Uani 1 1 d . . . . .
H5 H 0.3797 0.5433 1.1727 0.104 Uiso 1 1 calc R U . . .
C6 C 0.2301(3) 0.6571(3) 1.0597(2) 0.0760(7) Uani 1 1 d . . . . .
H6 H 0.3231 0.6834 0.9976 0.091 Uiso 1 1 calc R U . . .
C7 C 0.0558(3) 0.7044(3) 1.0440(2) 0.0594(6) Uani 1 1 d . . . . .
C8 C 0.0073(3) 0.7895(3) 0.9363(2) 0.0599(6) Uani 1 1 d . . . . .
C9 C -0.1632(3) 0.8301(3) 0.9322(2) 0.0668(6) Uani 1 1 d . . . . .
C10 C -0.2460(3) 0.9254(3) 0.8355(2) 0.0880(8) Uani 1 1 d . . . . .
H10A H -0.1636 0.9776 0.7797 0.132 Uiso 1 1 calc R U . . .
H10B H -0.3543 1.0087 0.8782 0.132 Uiso 1 1 calc R U . . .
H10C H -0.2733 0.8512 0.7864 0.132 Uiso 1 1 calc R U . . .
C11 C 0.1493(3) 0.8339(3) 0.8317(2) 0.0658(6) Uani 1 1 d . . . . .
C12 C 0.2770(3) 0.8169(3) 0.5994(2) 0.0664(6) Uani 1 1 d . . . . .
C13 C 0.4651(3) 0.7125(3) 0.5995(2) 0.0791(7) Uani 1 1 d . . . . .
H13A H 0.5047 0.7620 0.6579 0.119 Uiso 1 1 calc R U . . .
H13B H 0.5461 0.7074 0.5151 0.119 Uiso 1 1 calc R U . . .
H13C H 0.4627 0.6023 0.6254 0.119 Uiso 1 1 calc R U . . .
C14 C 0.2588(3) 1.0017(3) 0.5870(3) 0.0962(9) Uani 1 1 d . . . . .
H14A H 0.1340 1.0634 0.6096 0.144 Uiso 1 1 calc R U . . .
H14B H 0.3162 1.0233 0.5004 0.144 Uiso 1 1 calc R U . . .
H14C H 0.3145 1.0348 0.6431 0.144 Uiso 1 1 calc R U . . .
C15 C 0.2194(3) 0.7519(3) 0.4967(2) 0.0928(8) Uani 1 1 d . . . . .
H15A H 0.2240 0.6375 0.5109 0.139 Uiso 1 1 calc R U . . .
H15B H 0.2988 0.7615 0.4142 0.139 Uiso 1 1 calc R U . . .
H15C H 0.0991 0.8157 0.5003 0.139 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
O1 C1 1.204(3) . ?
O2 C1 1.361(3) . ?
O2 C9 1.373(3) . ?
O3 C11 1.206(3) . ?
O4 C11 1.338(3) . ?
O4 C12 1.477(3) . ?
C1 C2 1.459(3) . ?
C2 C3 1.392(3) . ?
C2 C7 1.396(3) . ?
C3 C4 1.362(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.367(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.370(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.417(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.441(3) . ?
C8 C9 1.345(3) . ?
C8 C11 1.490(3) . ?
C9 C10 1.492(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C12 C14 1.524(4) . ?
C12 C15 1.524(3) . ?
C12 C13 1.527(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 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
C1 O2 C9 122.50(19) . . ?
C11 O4 C12 120.58(18) . . ?
O1 C1 O2 116.3(2) . . ?
O1 C1 C2 126.1(3) . . ?
O2 C1 C2 117.6(2) . . ?
C3 C2 C7 121.1(2) . . ?
C3 C2 C1 118.8(2) . . ?
C7 C2 C1 120.1(2) . . ?
C4 C3 C2 120.4(2) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 120.2(3) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 120.6(2) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C7 121.2(2) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C2 C7 C6 116.5(2) . . ?
C2 C7 C8 118.0(2) . . ?
C6 C7 C8 125.4(2) . . ?
C9 C8 C7 120.3(2) . . ?
C9 C8 C11 121.2(2) . . ?
C7 C8 C11 118.5(2) . . ?
C8 C9 O2 121.5(2) . . ?
C8 C9 C10 129.7(2) . . ?
O2 C9 C10 108.7(2) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O3 C11 O4 125.1(2) . . ?
O3 C11 C8 124.1(2) . . ?
O4 C11 C8 110.7(2) . . ?
O4 C12 C14 109.91(18) . . ?
O4 C12 C15 102.06(19) . . ?
C14 C12 C15 111.5(2) . . ?
O4 C12 C13 109.19(18) . . ?
C14 C12 C13 113.1(2) . . ?
C15 C12 C13 110.5(2) . . ?
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 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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 C1 O1 179.3(2) . . . . ?
C9 O2 C1 C2 -0.1(3) . . . . ?
O1 C1 C2 C3 1.7(4) . . . . ?
O2 C1 C2 C3 -179.0(2) . . . . ?
O1 C1 C2 C7 -178.3(2) . . . . ?
O2 C1 C2 C7 1.0(3) . . . . ?
C7 C2 C3 C4 0.5(3) . . . . ?
C1 C2 C3 C4 -179.4(2) . . . . ?
C2 C3 C4 C5 0.3(4) . . . . ?
C3 C4 C5 C6 -0.5(4) . . . . ?
C4 C5 C6 C7 -0.2(4) . . . . ?
C3 C2 C7 C6 -1.1(3) . . . . ?
C1 C2 C7 C6 178.84(18) . . . . ?
C3 C2 C7 C8 178.57(19) . . . . ?
C1 C2 C7 C8 -1.5(3) . . . . ?
C5 C6 C7 C2 1.0(3) . . . . ?
C5 C6 C7 C8 -178.7(2) . . . . ?
C2 C7 C8 C9 1.1(3) . . . . ?
C6 C7 C8 C9 -179.3(2) . . . . ?
C2 C7 C8 C11 179.95(18) . . . . ?
C6 C7 C8 C11 -0.4(3) . . . . ?
C7 C8 C9 O2 -0.2(3) . . . . ?
C11 C8 C9 O2 -179.03(18) . . . . ?
C7 C8 C9 C10 176.2(2) . . . . ?
C11 C8 C9 C10 -2.7(3) . . . . ?
C1 O2 C9 C8 -0.3(3) . . . . ?
C1 O2 C9 C10 -177.4(2) . . . . ?
C12 O4 C11 O3 -1.6(3) . . . . ?
C12 O4 C11 C8 -178.73(16) . . . . ?
C9 C8 C11 O3 133.4(2) . . . . ?
C7 C8 C11 O3 -45.4(3) . . . . ?
C9 C8 C11 O4 -49.4(3) . . . . ?
C7 C8 C11 O4 131.7(2) . . . . ?
C11 O4 C12 C14 -60.1(3) . . . . ?
C11 O4 C12 C15 -178.58(18) . . . . ?
C11 O4 C12 C13 64.5(2) . . . . ?

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
C14 H14C O3 0.96 2.47 2.954(4) 111.3 .
C13 H13A O3 0.96 2.49 2.993(3) 112.9 .
C10 H10A O4 0.96 2.47 2.962(4) 111.5 .
C10 H10A O4 0.96 2.47 2.962(4) 111.5 .
C13 H13A O3 0.96 2.49 2.993(3) 112.9 .
C14 H14C O3 0.96 2.47 2.954(4) 111.3 .
C10 H10A O4 0.96 2.47 2.962(4) 111.5 .
C13 H13A O3 0.96 2.49 2.993(3) 112.9 .
C14 H14C O3 0.96 2.47 2.954(4) 111.3 .

_refine_diff_density_max         0.127
_refine_diff_density_min         -0.116
_refine_diff_density_rms         0.029

_shelxl_version_number           2013-4



