# 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/. 
# 
# Audit and citation data items have may 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_1968GuillotICMMO
_audit_block_doi                 10.5517/cc12lvzh
_database_code_depnum_ccdc_archive 'CCDC 1001237'
_audit_update_record             
;
2014-05-05 deposited with the CCDC.
2014-12-07 downloaded from the CCDC.
;

#marcpressetlcm0529_0m 

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C17 H20 O4'
_chemical_formula_sum            'C17 H20 O4'
_chemical_melting_point          ?

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless

_diffrn_ambient_temperature      100(1)
_chemical_formula_weight         288.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_int_tables_number      14
_chemical_absolute_configuration .

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                   8.3539(3)
_cell_length_b                   11.1450(3)
_cell_length_c                   16.1987(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.7310(10)
_cell_angle_gamma                90.00
_cell_volume                     1476.67(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9784
_exptl_absorpt_correction_T_max  0.9954
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'kappa X8 APEX II Bruke rICMMO'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            26630
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_av_sigmaI/netI    0.0372
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.23
_diffrn_reflns_theta_max         30.55
_reflns_number_total             4434
_reflns_number_gt                3431
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0479P)²+0.4124P] 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         4434
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_ref         0.1080
_refine_ls_wR_factor_gt          0.0985
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.001
_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 0.65652(13) 0.33613(9) -0.11819(7) 0.0135(2) Uani 1 1 d . . .
C2 C 1.02357(13) 0.42273(9) -0.14544(7) 0.0129(2) Uani 1 1 d . . .
H2 H 1.1142 0.4565 -0.1039 0.016 Uiso 1 1 calc R . .
C3 C 1.09171(13) 0.40218(9) -0.22478(7) 0.0135(2) Uani 1 1 d . . .
C4 C 1.11157(13) 0.25853(10) -0.03769(7) 0.0140(2) Uani 1 1 d . . .
C5 C 0.89043(14) 0.52154(9) -0.16089(7) 0.0149(2) Uani 1 1 d . . .
H5A H 0.8653 0.5434 -0.1070 0.018 Uiso 1 1 calc R . .
H5B H 0.9359 0.5920 -0.1828 0.018 Uiso 1 1 calc R . .
C6 C 1.06408(15) 0.30014(10) -0.27513(8) 0.0188(2) Uani 1 1 d . . .
H6 H 1.0007 0.2381 -0.2607 0.023 Uiso 1 1 calc R . .
C7 C 0.97249(13) 0.30703(9) -0.10433(7) 0.0125(2) Uani 1 1 d . . .
H7 H 0.9407 0.2460 -0.1481 0.015 Uiso 1 1 calc R . .
C8 C 0.73300(14) 0.48975(10) -0.22025(7) 0.0153(2) Uani 1 1 d . . .
C9 C 0.66022(14) 0.36812(10) -0.21025(7) 0.0148(2) Uani 1 1 d . . .
H9A H 0.7230 0.3077 -0.2328 0.018 Uiso 1 1 calc R . .
H9B H 0.5495 0.3660 -0.2432 0.018 Uiso 1 1 calc R . .
C10 C 0.82747(13) 0.33125(9) -0.06197(7) 0.0131(2) Uani 1 1 d . . .
C11 C 1.18644(14) 0.49383(10) -0.24906(8) 0.0172(2) Uani 1 1 d . . .
H11 H 1.2053 0.5632 -0.2166 0.021 Uiso 1 1 calc R . .
C12 C 0.58324(14) 0.20962(10) -0.11625(8) 0.0189(2) Uani 1 1 d . . .
H12A H 0.5790 0.1888 -0.0592 0.028 Uiso 1 1 calc R . .
H12B H 0.6503 0.1527 -0.1381 0.028 Uiso 1 1 calc R . .
H12C H 0.4748 0.2085 -0.1502 0.028 Uiso 1 1 calc R . .
C13 C 1.25282(14) 0.48366(11) -0.32044(8) 0.0212(3) Uani 1 1 d . . .
H13 H 1.3157 0.5458 -0.3353 0.025 Uiso 1 1 calc R . .
C14 C 1.22578(15) 0.38121(12) -0.36966(8) 0.0222(3) Uani 1 1 d . . .
H14 H 1.2711 0.3738 -0.4173 0.027 Uiso 1 1 calc R . .
C15 C 0.55143(14) 0.42576(10) -0.08169(8) 0.0189(2) Uani 1 1 d . . .
H15A H 0.5488 0.4038 -0.0247 0.028 Uiso 1 1 calc R . .
H15B H 0.4423 0.4252 -0.1150 0.028 Uiso 1 1 calc R . .
H15C H 0.5971 0.5047 -0.0825 0.028 Uiso 1 1 calc R . .
C16 C 1.13068(16) 0.29008(11) -0.34719(8) 0.0230(3) Uani 1 1 d . . .
H16 H 1.1109 0.2215 -0.3804 0.028 Uiso 1 1 calc R . .
C17 C 1.19919(17) 0.09189(12) 0.04874(9) 0.0267(3) Uani 1 1 d . . .
H17A H 1.3030 0.0845 0.0324 0.040 Uiso 1 1 calc R . .
H17B H 1.1619 0.0140 0.0617 0.040 Uiso 1 1 calc R . .
H17C H 1.2106 0.1424 0.0976 0.040 Uiso 1 1 calc R . .
O1 O 0.84789(10) 0.34282(8) 0.01378(5) 0.01896(18) Uani 1 1 d . . .
O2 O 0.66513(11) 0.56091(8) -0.27285(6) 0.02172(19) Uani 1 1 d . . .
O3 O 1.23036(10) 0.31354(7) -0.00354(6) 0.02141(19) Uani 1 1 d . . .
O4 O 1.08182(10) 0.14431(7) -0.01973(5) 0.01869(18) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0135(5) 0.0131(5) 0.0141(5) -0.0009(4) 0.0031(4) -0.0001(4)
C2 0.0146(5) 0.0103(4) 0.0139(5) 0.0000(4) 0.0029(4) -0.0014(4)
C3 0.0126(5) 0.0139(5) 0.0135(5) 0.0029(4) 0.0017(4) 0.0017(4)
C4 0.0165(5) 0.0121(5) 0.0141(5) 0.0004(4) 0.0045(4) 0.0011(4)
C5 0.0186(5) 0.0103(5) 0.0163(6) -0.0004(4) 0.0047(4) -0.0004(4)
C6 0.0229(6) 0.0158(5) 0.0187(6) 0.0003(4) 0.0065(5) -0.0014(4)
C7 0.0139(5) 0.0106(4) 0.0128(5) -0.0005(4) 0.0023(4) -0.0002(4)
C8 0.0174(5) 0.0142(5) 0.0158(5) 0.0006(4) 0.0067(4) 0.0038(4)
C9 0.0157(5) 0.0136(5) 0.0144(5) -0.0001(4) 0.0011(4) 0.0010(4)
C10 0.0161(5) 0.0094(4) 0.0143(5) -0.0001(4) 0.0039(4) -0.0011(4)
C11 0.0154(5) 0.0161(5) 0.0199(6) 0.0024(4) 0.0027(4) -0.0006(4)
C12 0.0193(5) 0.0155(5) 0.0218(6) 0.0001(4) 0.0041(4) -0.0042(4)
C13 0.0174(6) 0.0241(6) 0.0228(6) 0.0070(5) 0.0062(5) 0.0002(4)
C14 0.0213(6) 0.0295(6) 0.0174(6) 0.0054(5) 0.0075(5) 0.0058(5)
C15 0.0180(5) 0.0179(5) 0.0224(6) -0.0012(5) 0.0076(5) 0.0019(4)
C16 0.0307(7) 0.0220(6) 0.0176(6) -0.0024(5) 0.0081(5) 0.0019(5)
C17 0.0311(7) 0.0199(6) 0.0240(7) 0.0085(5) -0.0061(5) 0.0010(5)
O1 0.0212(4) 0.0219(4) 0.0140(4) -0.0018(3) 0.0041(3) -0.0014(3)
O2 0.0232(4) 0.0200(4) 0.0223(5) 0.0080(4) 0.0053(3) 0.0054(3)
O3 0.0180(4) 0.0191(4) 0.0243(5) 0.0025(3) -0.0023(3) -0.0033(3)
O4 0.0222(4) 0.0127(4) 0.0184(4) 0.0040(3) -0.0025(3) -0.0007(3)

_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C15 1.5261(15) . ?
C1 C10 1.5307(15) . ?
C1 C12 1.5400(15) . ?
C1 C9 1.5398(15) . ?
C2 C3 1.5249(15) . ?
C2 C5 1.5489(15) . ?
C2 C7 1.5505(15) . ?
C3 C6 1.3912(16) . ?
C3 C11 1.3968(15) . ?
C4 O3 1.2014(14) . ?
C4 O4 1.3403(13) . ?
C4 C7 1.5158(15) . ?
C5 C8 1.5051(16) . ?
C6 C16 1.3960(17) . ?
C7 C10 1.5328(15) . ?
C8 O2 1.2165(14) . ?
C8 C9 1.5078(15) . ?
C10 O1 1.2108(14) . ?
C11 C13 1.3849(17) . ?
C13 C14 1.3846(19) . ?
C14 C16 1.3830(18) . ?
C17 O4 1.4458(14) . ?

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
C15 C1 C10 109.47(9) . . ?
C15 C1 C12 109.21(9) . . ?
C10 C1 C12 106.38(9) . . ?
C15 C1 C9 110.49(9) . . ?
C10 C1 C9 112.61(9) . . ?
C12 C1 C9 108.55(9) . . ?
C3 C2 C5 110.45(9) . . ?
C3 C2 C7 114.81(9) . . ?
C5 C2 C7 114.16(8) . . ?
C6 C3 C11 117.95(10) . . ?
C6 C3 C2 124.82(10) . . ?
C11 C3 C2 117.22(10) . . ?
O3 C4 O4 123.85(10) . . ?
O3 C4 C7 125.99(10) . . ?
O4 C4 C7 110.13(9) . . ?
C8 C5 C2 116.19(9) . . ?
C3 C6 C16 120.60(11) . . ?
C4 C7 C10 107.76(9) . . ?
C4 C7 C2 111.37(9) . . ?
C10 C7 C2 110.95(8) . . ?
O2 C8 C5 121.08(10) . . ?
O2 C8 C9 121.37(11) . . ?
C5 C8 C9 117.52(9) . . ?
C8 C9 C1 113.58(9) . . ?
O1 C10 C1 121.42(10) . . ?
O1 C10 C7 120.74(10) . . ?
C1 C10 C7 117.81(9) . . ?
C13 C11 C3 121.41(11) . . ?
C14 C13 C11 120.14(11) . . ?
C16 C14 C13 119.30(11) . . ?
C14 C16 C6 120.59(12) . . ?
C4 O4 C17 115.06(9) . . ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.050
