# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_t_0m
_audit_block_doi                 10.5517/ccdc.csd.cc1mmymt
_database_code_depnum_ccdc_archive 'CCDC 1508727'
_audit_update_record             
;
2016-10-07 deposited with the CCDC.
2017-01-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H16 O4'
_chemical_formula_sum            'C19 H16 O4'
_chemical_formula_weight         308.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

_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'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   15.9902(5)
_cell_length_b                   6.7069(2)
_cell_length_c                   15.5970(5)
_cell_angle_alpha                90
_cell_angle_beta                 107.569(2)
_cell_angle_gamma                90
_cell_volume                     1594.67(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3405
_cell_measurement_theta_min      5.67
_cell_measurement_theta_max      68.01

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.736
_shelx_estimated_absorpt_T_min   0.855
_shelx_estimated_absorpt_T_max   0.917
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8724
_diffrn_reflns_av_unetI/netI     0.0464
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.972
_diffrn_reflns_theta_max         68.246
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2917
_reflns_number_gt                2448
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.820
_reflns_Friedel_fraction_max     0.986
_reflns_Friedel_fraction_full    0.992

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0462P)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_abs_structure_details 
;
 Flack x determined using 915 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(16)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2917
_refine_ls_number_parameters     208
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0374
_refine_ls_wR_factor_ref         0.0902
_refine_ls_wR_factor_gt          0.0844
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_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 0.62071(12) 0.3163(3) 0.25934(13) 0.0332(4) Uani 1 1 d . . . . .
C1 C 0.65554(16) 0.4981(5) 0.24204(16) 0.0283(6) Uani 1 1 d . . . . .
O2 O 0.49041(14) 0.2142(3) 0.26885(15) 0.0391(5) Uani 1 1 d . . . . .
C2 C 0.59594(15) 0.6522(4) 0.23026(16) 0.0264(5) Uani 1 1 d . . . . .
O3 O 0.36606(13) 0.6683(4) 0.15781(14) 0.0501(6) Uani 1 1 d . . . . .
C3 C 0.61940(19) 0.8403(4) 0.21062(18) 0.0340(6) Uani 1 1 d . . . . .
H3 H 0.5793 0.9484 0.2018 0.041 Uiso 1 1 calc R U . . .
C5 C 0.76228(18) 0.7112(5) 0.21722(19) 0.0386(7) Uani 1 1 d . . . . .
H5 H 0.8194 0.7341 0.2127 0.046 Uiso 1 1 calc R U . . .
O4 O 0.44980(13) 0.5030(4) 0.08974(13) 0.0448(6) Uani 1 1 d . . . . .
C4 C 0.7038(2) 0.8677(5) 0.2040(2) 0.0390(7) Uani 1 1 d . . . . .
H4 H 0.7212 0.9962 0.1903 0.047 Uiso 1 1 calc R U . . .
C7 C 0.53584(17) 0.3487(4) 0.25861(17) 0.0297(6) Uani 1 1 d . . . . .
C6 C 0.73925(18) 0.5207(5) 0.23693(19) 0.0356(7) Uani 1 1 d . . . . .
H6 H 0.7792 0.4121 0.2463 0.043 Uiso 1 1 calc R U . . .
C8 C 0.51312(16) 0.5707(4) 0.24404(18) 0.0272(6) Uani 1 1 d . . . . .
C9 C 0.48988(17) 0.6584(5) 0.32592(17) 0.0327(6) Uani 1 1 d . . . . .
H9A H 0.4727 0.7997 0.3134 0.039 Uiso 1 1 calc R U . . .
H9B H 0.4386 0.5858 0.3333 0.039 Uiso 1 1 calc R U . . .
C10 C 0.56402(17) 0.6466(5) 0.41308(17) 0.0345(6) Uani 1 1 d . . . . .
C11 C 0.6125(2) 0.8136(6) 0.4487(2) 0.0461(8) Uani 1 1 d . . . . .
H11 H 0.6000 0.9369 0.4175 0.055 Uiso 1 1 calc R U . . .
C12 C 0.6793(2) 0.8038(7) 0.5298(2) 0.0553(10) Uani 1 1 d . . . . .
H12 H 0.7120 0.9201 0.5536 0.066 Uiso 1 1 calc R U . . .
C13 C 0.6983(2) 0.6272(7) 0.5757(2) 0.0552(10) Uani 1 1 d . . . . .
H13 H 0.7443 0.6207 0.6309 0.066 Uiso 1 1 calc R U . . .
C14 C 0.6506(2) 0.4596(6) 0.5416(2) 0.0506(9) Uani 1 1 d . . . . .
H14 H 0.6636 0.3369 0.5733 0.061 Uiso 1 1 calc R U . . .
C15 C 0.5833(2) 0.4686(6) 0.46070(19) 0.0421(7) Uani 1 1 d . . . . .
H15 H 0.5502 0.3523 0.4378 0.050 Uiso 1 1 calc R U . . .
C16 C 0.43330(16) 0.5894(4) 0.15968(18) 0.0294(6) Uani 1 1 d . . . . .
C17 C 0.3796(2) 0.4962(6) 0.00523(19) 0.0461(8) Uani 1 1 d . . . . .
H17A H 0.4015 0.5470 -0.0436 0.055 Uiso 1 1 calc R U . . .
H17B H 0.3310 0.5836 0.0091 0.055 Uiso 1 1 calc R U . . .
C18 C 0.3468(2) 0.2918(6) -0.0160(2) 0.0546(9) Uani 1 1 d . . . . .
H18 H 0.2984 0.2752 -0.0687 0.065 Uiso 1 1 calc R U . . .
C19 C 0.3768(3) 0.1313(7) 0.0296(3) 0.0830(16) Uani 1 1 d . . . . .
H19A H 0.4252 0.1394 0.0829 0.100 Uiso 1 1 calc R U . . .
H19B H 0.3505 0.0059 0.0096 0.100 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 C7 1.371(3) . ?
O1 C1 1.400(4) . ?
C1 C6 1.373(4) . ?
C1 C2 1.380(4) . ?
O2 C7 1.199(4) . ?
C2 C3 1.377(4) . ?
C2 C8 1.507(4) . ?
O3 C16 1.191(3) . ?
C3 C4 1.395(4) . ?
C3 H3 0.9500 . ?
C5 C4 1.380(5) . ?
C5 C6 1.390(5) . ?
C5 H5 0.9500 . ?
O4 C16 1.330(4) . ?
O4 C17 1.451(3) . ?
C4 H4 0.9500 . ?
C7 C8 1.533(4) . ?
C6 H6 0.9500 . ?
C8 C16 1.537(4) . ?
C8 C9 1.550(4) . ?
C9 C10 1.512(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.380(5) . ?
C10 C15 1.390(5) . ?
C11 C12 1.389(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.369(6) . ?
C12 H12 0.9500 . ?
C13 C14 1.372(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.391(5) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C17 C18 1.469(5) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.300(6) . ?
C18 H18 0.9500 . ?
C19 H19A 0.9500 . ?
C19 H19B 0.9500 . ?

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
C7 O1 C1 108.1(2) . . ?
C6 C1 C2 123.8(3) . . ?
C6 C1 O1 124.0(3) . . ?
C2 C1 O1 112.3(2) . . ?
C3 C2 C1 119.5(2) . . ?
C3 C2 C8 132.4(3) . . ?
C1 C2 C8 108.1(2) . . ?
C2 C3 C4 118.1(3) . . ?
C2 C3 H3 120.9 . . ?
C4 C3 H3 120.9 . . ?
C4 C5 C6 121.3(3) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C16 O4 C17 117.9(2) . . ?
C5 C4 C3 121.1(3) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
O2 C7 O1 121.2(3) . . ?
O2 C7 C8 128.6(3) . . ?
O1 C7 C8 110.2(2) . . ?
C1 C6 C5 116.3(3) . . ?
C1 C6 H6 121.9 . . ?
C5 C6 H6 121.9 . . ?
C2 C8 C7 101.2(2) . . ?
C2 C8 C16 112.7(2) . . ?
C7 C8 C16 107.8(2) . . ?
C2 C8 C9 114.8(2) . . ?
C7 C8 C9 110.6(2) . . ?
C16 C8 C9 109.3(2) . . ?
C10 C9 C8 113.8(2) . . ?
C10 C9 H9A 108.8 . . ?
C8 C9 H9A 108.8 . . ?
C10 C9 H9B 108.8 . . ?
C8 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
C11 C10 C15 118.3(3) . . ?
C11 C10 C9 120.8(3) . . ?
C15 C10 C9 120.8(3) . . ?
C10 C11 C12 120.8(4) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C13 C12 C11 120.3(4) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 119.8(3) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C13 C14 C15 120.2(4) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C14 C15 C10 120.5(3) . . ?
C14 C15 H15 119.7 . . ?
C10 C15 H15 119.7 . . ?
O3 C16 O4 125.1(3) . . ?
O3 C16 C8 124.6(3) . . ?
O4 C16 C8 110.3(2) . . ?
O4 C17 C18 111.1(3) . . ?
O4 C17 H17A 109.4 . . ?
C18 C17 H17A 109.4 . . ?
O4 C17 H17B 109.4 . . ?
C18 C17 H17B 109.4 . . ?
H17A C17 H17B 108.0 . . ?
C19 C18 C17 127.0(3) . . ?
C19 C18 H18 116.5 . . ?
C17 C18 H18 116.5 . . ?
C18 C19 H19A 120.0 . . ?
C18 C19 H19B 120.0 . . ?
H19A C19 H19B 120.0 . . ?

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
C7 O1 C1 C6 -179.3(2) . . . . ?
C7 O1 C1 C2 0.4(3) . . . . ?
C6 C1 C2 C3 1.2(4) . . . . ?
O1 C1 C2 C3 -178.5(2) . . . . ?
C6 C1 C2 C8 -178.1(2) . . . . ?
O1 C1 C2 C8 2.2(3) . . . . ?
C1 C2 C3 C4 -0.5(4) . . . . ?
C8 C2 C3 C4 178.6(3) . . . . ?
C6 C5 C4 C3 0.4(5) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
C1 O1 C7 O2 177.5(2) . . . . ?
C1 O1 C7 C8 -2.8(3) . . . . ?
C2 C1 C6 C5 -1.1(4) . . . . ?
O1 C1 C6 C5 178.6(2) . . . . ?
C4 C5 C6 C1 0.2(4) . . . . ?
C3 C2 C8 C7 177.3(3) . . . . ?
C1 C2 C8 C7 -3.6(3) . . . . ?
C3 C2 C8 C16 62.5(4) . . . . ?
C1 C2 C8 C16 -118.4(2) . . . . ?
C3 C2 C8 C9 -63.6(4) . . . . ?
C1 C2 C8 C9 115.5(2) . . . . ?
O2 C7 C8 C2 -176.5(3) . . . . ?
O1 C7 C8 C2 3.9(3) . . . . ?
O2 C7 C8 C16 -57.9(4) . . . . ?
O1 C7 C8 C16 122.4(2) . . . . ?
O2 C7 C8 C9 61.5(4) . . . . ?
O1 C7 C8 C9 -118.2(2) . . . . ?
C2 C8 C9 C10 -52.5(4) . . . . ?
C7 C8 C9 C10 61.2(3) . . . . ?
C16 C8 C9 C10 179.7(3) . . . . ?
C8 C9 C10 C11 103.9(3) . . . . ?
C8 C9 C10 C15 -78.1(3) . . . . ?
C15 C10 C11 C12 0.5(5) . . . . ?
C9 C10 C11 C12 178.6(3) . . . . ?
C10 C11 C12 C13 0.1(6) . . . . ?
C11 C12 C13 C14 -0.4(6) . . . . ?
C12 C13 C14 C15 0.0(5) . . . . ?
C13 C14 C15 C10 0.6(5) . . . . ?
C11 C10 C15 C14 -0.9(4) . . . . ?
C9 C10 C15 C14 -178.9(3) . . . . ?
C17 O4 C16 O3 -2.7(5) . . . . ?
C17 O4 C16 C8 176.5(3) . . . . ?
C2 C8 C16 O3 -125.6(3) . . . . ?
C7 C8 C16 O3 123.6(3) . . . . ?
C9 C8 C16 O3 3.4(4) . . . . ?
C2 C8 C16 O4 55.2(3) . . . . ?
C7 C8 C16 O4 -55.6(3) . . . . ?
C9 C8 C16 O4 -175.8(2) . . . . ?
C16 O4 C17 C18 -109.6(3) . . . . ?
O4 C17 C18 C19 -3.4(6) . . . . ?

_refine_diff_density_max         0.153
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.033

