# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_LCY14
_database_code_depnum_ccdc_archive 'CCDC 1838973'
_audit_update_record             
;
2018-06-13 deposited with the CCDC.
2018-06-19 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         'C15 H14 O4'
_chemical_formula_sum            'C14 H14 O4'
_chemical_formula_weight         258.26

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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-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                   10.287(2)
_cell_length_b                   11.291(2)
_cell_length_c                   20.866(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2423.6(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    574
_cell_measurement_theta_min      12.5
_cell_measurement_theta_max      25.0

_exptl_crystal_description       Columns
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_F_000             1065
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3841
_exptl_crystal_size_mid          0.1620
_exptl_crystal_size_min          0.1406
_exptl_absorpt_coefficient_mu    0.099
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Smart Apex'
_diffrn_measurement_method       'phi-omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26046
_diffrn_reflns_av_unetI/netI     0.0151
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.952
_diffrn_reflns_theta_max         28.332
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2965
_reflns_number_gt                2579
_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       ?
_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)+(0.0790P)²+0.6314P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2965
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_ref         0.1315
_refine_ls_wR_factor_gt          0.1168
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.090
_refine_ls_shift/su_max          0.003
_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
C10 C 0.12163(11) 0.16539(9) 0.44155(5) 0.0218(2) Uani 1 1 d . . . . .
C5 C 0.09264(11) 0.16455(10) 0.37288(5) 0.0244(2) Uani 1 1 d . . . . .
C13 C 0.30432(11) 0.17598(10) 0.57019(6) 0.0246(2) Uani 1 1 d . . . . .
C12 C 0.37812(11) 0.11040(10) 0.53004(6) 0.0252(3) Uani 1 1 d . . . . .
C9 C 0.23726(10) 0.23698(9) 0.46576(5) 0.0227(2) Uani 1 1 d . . . . .
C14 C 0.22159(12) 0.26576(11) 0.53726(6) 0.0279(3) Uani 1 1 d . . . . .
C11 C 0.35303(10) 0.14741(9) 0.46497(6) 0.0224(2) Uani 1 1 d . . . . .
C6 C 0.16033(12) 0.23878(11) 0.32954(6) 0.0301(3) Uani 1 1 d . . . . .
C8 C 0.25952(13) 0.34715(10) 0.42424(7) 0.0313(3) Uani 1 1 d . . . . .
C4 C -0.00578(12) 0.08794(11) 0.34951(6) 0.0305(3) Uani 1 1 d . . . . .
C7 C 0.26560(14) 0.32096(12) 0.35276(7) 0.0358(3) Uani 1 1 d . . . . .
C3 C -0.03508(15) 0.08606(14) 0.28431(7) 0.0419(3) Uani 1 1 d . . . . .
C1 C 0.12847(16) 0.23408(14) 0.26504(7) 0.0418(4) Uani 1 1 d . . . . .
C2 C 0.03205(17) 0.15897(15) 0.24307(7) 0.0466(4) Uani 1 1 d . . . . .
O1 O 0.29838(9) 0.17275(8) 0.63349(4) 0.0318(2) Uani 1 1 d . . . . .
C15 C 0.37044(14) 0.07873(14) 0.66373(6) 0.0369(3) Uani 1 1 d . . . . .
O3 O 0.05788(8) 0.10603(8) 0.47973(4) 0.0300(2) Uani 1 1 d . . . . .
O2 O 0.40794(8) 0.11408(8) 0.41622(4) 0.0298(2) Uani 1 1 d . . . . .
O4 O -0.07355(9) 0.01418(9) 0.38774(5) 0.0388(3) Uani 1 1 d . . . . .
H1 H 0.3336(16) 0.0039(16) 0.6503(8) 0.041(4) Uiso 1 1 d . . . . .
H2 H 0.3585(18) 0.0898(16) 0.7092(9) 0.049(5) Uiso 1 1 d . . . . .
H3 H 0.4641(19) 0.0808(17) 0.6534(9) 0.052(5) Uiso 1 1 d . . . . .
H4 H 0.4404(14) 0.0495(14) 0.5402(7) 0.030(4) Uiso 1 1 d . . . . .
H6 H 0.1314(17) 0.2609(15) 0.5512(8) 0.041(4) Uiso 1 1 d . . . . .
H5 H 0.2529(17) 0.3450(16) 0.5478(7) 0.040(4) Uiso 1 1 d . . . . .
H12 H 0.2573(18) 0.3953(16) 0.3306(8) 0.046(4) Uiso 1 1 d . . . . .
H11 H 0.3527(16) 0.2862(15) 0.3432(8) 0.040(4) Uiso 1 1 d . . . . .
H14 H 0.1832(15) 0.4025(14) 0.4332(7) 0.036(4) Uiso 1 1 d . . . . .
H10 H 0.1750(18) 0.2859(17) 0.2358(9) 0.049(5) Uiso 1 1 d . . . . .
H13 H 0.3402(16) 0.3877(15) 0.4395(8) 0.039(4) Uiso 1 1 d . . . . .
H9 H 0.013(2) 0.1580(19) 0.1986(11) 0.064(6) Uiso 1 1 d . . . . .
H7 H -0.041(2) 0.030(2) 0.4290(11) 0.065(6) Uiso 1 1 d . . . . .
H8 H -0.103(2) 0.0352(17) 0.2701(9) 0.051(5) Uiso 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
C10 O3 1.2305(14) . ?
C10 C5 1.4636(16) . ?
C10 C9 1.5243(15) . ?
C5 C4 1.4181(17) . ?
C5 C6 1.4160(17) . ?
C13 O1 1.3228(15) . ?
C13 C12 1.3515(16) . ?
C13 C14 1.4914(17) . ?
C12 C11 1.4438(16) . ?
C9 C8 1.5331(16) . ?
C9 C14 1.5354(16) . ?
C9 C11 1.5625(15) . ?
C11 O2 1.2230(14) . ?
C6 C1 1.3862(19) . ?
C6 C7 1.5061(19) . ?
C8 C7 1.522(2) . ?
C4 O4 1.3475(17) . ?
C4 C3 1.3937(19) . ?
C3 C2 1.377(2) . ?
C1 C2 1.383(2) . ?
O1 C15 1.4403(17) . ?

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 C10 C5 121.46(10) . . ?
O3 C10 C9 119.35(10) . . ?
C5 C10 C9 119.13(10) . . ?
C4 C5 C6 119.51(11) . . ?
C4 C5 C10 119.07(11) . . ?
C6 C5 C10 121.42(11) . . ?
O1 C13 C12 129.04(11) . . ?
O1 C13 C14 116.90(10) . . ?
C12 C13 C14 114.03(11) . . ?
C13 C12 C11 108.90(10) . . ?
C10 C9 C8 111.07(9) . . ?
C10 C9 C14 110.64(9) . . ?
C8 C9 C14 113.14(10) . . ?
C10 C9 C11 104.36(8) . . ?
C8 C9 C11 113.92(9) . . ?
C14 C9 C11 103.13(9) . . ?
C13 C14 C9 104.12(9) . . ?
O2 C11 C12 127.63(11) . . ?
O2 C11 C9 124.05(10) . . ?
C12 C11 C9 108.29(9) . . ?
C1 C6 C5 118.76(13) . . ?
C1 C6 C7 120.39(12) . . ?
C5 C6 C7 120.85(11) . . ?
C7 C8 C9 113.72(10) . . ?
O4 C4 C3 117.16(12) . . ?
O4 C4 C5 122.88(11) . . ?
C3 C4 C5 119.95(13) . . ?
C6 C7 C8 113.92(10) . . ?
C2 C3 C4 119.51(14) . . ?
C6 C1 C2 120.99(14) . . ?
C3 C2 C1 121.27(13) . . ?
C13 O1 C15 115.72(10) . . ?

_refine_diff_density_max         0.352
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.048

