# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_pgqw01_2016_0m
_audit_block_doi                 10.5517/ccdc.csd.cc1mgkbz
_database_code_depnum_ccdc_archive 'CCDC 1503541'
loop_
_audit_author_name
_audit_author_address
'Schatte Gabriele'
;queen's university
Canada
;
_audit_update_record             
;
2019-01-16 deposited with the CCDC.	2019-06-26 downloaded from the CCDC.
;

# SUBMISSION DETAILS

_audit_creation_method           'manual editing of SHELXL-2014/7 template'

# CHEMICAL DATA
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H14 O5'
_chemical_formula_sum            'C14 H14 O5'
_chemical_formula_weight         262.25

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'

# Crystal Data

_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                   7.5934(2)
_cell_length_b                   6.2414(2)
_cell_length_c                   26.6906(7)
_cell_angle_alpha                90
_cell_angle_beta                 94.3100(10)
_cell_angle_gamma                90
_cell_volume                     1261.38(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    6229
_cell_measurement_theta_min      2.388
_cell_measurement_theta_max      32.43

_exptl_crystal_description       plate-like
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_F_000             552
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.199
_exptl_crystal_size_mid          0.181
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.105
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7095
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   'SADABS v2012/1 (Apex2, Bruker AXS)'
_exptl_special_details           
;The value for wR₂(int) was 0.0459 before and
 0.0350 after correction. 
 The ratio of minimum to maximum transmission is 0.9413.
;

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Bruker AXS K780, fine-focus sealed tube'
_diffrn_radiation_monochromator  'horizontal mounted graphite crystal'
_diffrn_measurement_device_type  'Bruker Smart Apex2 CCD (Bruker AXS)'
_diffrn_measurement_method       'CCD rotation images,φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12425
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         1.530
_diffrn_reflns_theta_max         30.032
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3582
_reflns_number_gt                3015
_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       
; APEX2 software package v2013.10-0 (Bruker AXS)
;
_computing_cell_refinement       
; Saint V8.35A and SADABS v2014/5 (Apex3, v2015.9-0; Bruker AXS)
;
_computing_data_reduction        
; Saint V8.35A and SADABS V2014/5 (Apex3, v2015.9-0; Bruker AXS
;
_computing_structure_solution    
; SHELXT-2014 (Sheldrick, 2014)
;
_computing_structure_refinement  
; SHELXL-2014/7 (Sheldrick, 2014)
;
_computing_molecular_graphics    
; XP (SHELXTL-NT v6.14, Bruker AXS)
;

# REFINEMENT DATA

_refine_special_details          
;The non-hydrogen atoms were refined anisotropically. Hydrogen atoms of
 the phenyl-, CH₃- and CH₂- and ipso-CH groups were included at 
 geometrically idealized positions (C-H bond distances 0.95/0.99/0.99/
 1.00 Å) and were not refined. The isotropic thermal parameters of 
 these hydrogen atoms were fixed at 1.2 times (phenyl- and CH₂- and 
 ipso-CH- groups) and 1.5 times (CH₃-groups) that of the preceding
 carbon atom.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0575P)²+0.3865P] 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         3582
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0408
_refine_ls_wR_factor_ref         0.1130
_refine_ls_wR_factor_gt          0.1064
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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 0.80782(11) 0.28990(16) 0.30585(3) 0.0335(2) Uani 1 1 d . . . . .
O2 O 0.86682(12) -0.23160(15) 0.05023(4) 0.0390(2) Uani 1 1 d . . . . .
O3 O 0.64343(11) 0.22672(14) 0.01172(3) 0.02857(19) Uani 1 1 d . . . . .
O4 O 0.27108(11) 0.11798(15) 0.08113(4) 0.0367(2) Uani 1 1 d . . . . .
O5 O 0.37993(11) 0.44870(13) 0.09323(3) 0.0314(2) Uani 1 1 d . . . . .
C1 C 0.92854(18) 0.4564(3) 0.32152(5) 0.0427(3) Uani 1 1 d . . . . .
H1A H 0.9495 0.4538 0.3582 0.064 Uiso 1 1 calc R U . . .
H1B H 0.8785 0.5953 0.3109 0.064 Uiso 1 1 calc R U . . .
H1C H 1.0405 0.4343 0.3062 0.064 Uiso 1 1 calc R U . . .
C2 C 0.75990(14) 0.27559(19) 0.25561(4) 0.0248(2) Uani 1 1 d . . . . .
C3 C 0.63639(15) 0.1171(2) 0.24183(4) 0.0273(2) Uani 1 1 d . . . . .
H3 H 0.5896 0.0300 0.2668 0.033 Uiso 1 1 calc R U . . .
C4 C 0.58188(14) 0.08655(19) 0.19171(4) 0.0249(2) Uani 1 1 d . . . . .
H4 H 0.4974 -0.0217 0.1827 0.030 Uiso 1 1 calc R U . . .
C5 C 0.64889(13) 0.21233(17) 0.15401(4) 0.0203(2) Uani 1 1 d . . . . .
C6 C 0.76852(14) 0.37229(18) 0.16861(4) 0.0251(2) Uani 1 1 d . . . . .
H6 H 0.8130 0.4620 0.1437 0.030 Uiso 1 1 calc R U . . .
C7 C 0.82523(15) 0.4047(2) 0.21907(4) 0.0278(2) Uani 1 1 d . . . . .
H7 H 0.9080 0.5146 0.2283 0.033 Uiso 1 1 calc R U . . .
C8 C 0.58673(13) 0.16813(16) 0.09918(4) 0.01992(19) Uani 1 1 d . . . . .
C9 C 0.61115(14) -0.06983(17) 0.08466(4) 0.0228(2) Uani 1 1 d . . . . .
H9A H 0.6275 -0.1602 0.1151 0.027 Uiso 1 1 calc R U . . .
H9B H 0.5067 -0.1221 0.0638 0.027 Uiso 1 1 calc R U . . .
C10 C 0.77409(14) -0.07709(18) 0.05534(4) 0.0252(2) Uani 1 1 d . . . . .
C11 C 0.80647(15) 0.14238(19) 0.03568(4) 0.0266(2) Uani 1 1 d . . . . .
H11 H 0.9245 0.1866 0.0250 0.032 Uiso 1 1 calc R U . . .
C12 C 0.69436(14) 0.29015(17) 0.06220(4) 0.0220(2) Uani 1 1 d . . . . .
H12 H 0.7344 0.4402 0.0697 0.026 Uiso 1 1 calc R U . . .
C13 C 0.39363(14) 0.23683(18) 0.09005(4) 0.0222(2) Uani 1 1 d . . . . .
C14 C 0.20401(15) 0.5356(2) 0.08364(5) 0.0329(3) Uani 1 1 d . . . . .
H14A H 0.1288 0.4849 0.1095 0.049 Uiso 1 1 calc R U . . .
H14B H 0.1545 0.4883 0.0505 0.049 Uiso 1 1 calc R U . . .
H14C H 0.2095 0.6924 0.0844 0.049 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.
;

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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 C2 1.3656(12) . ?
O1 C1 1.4273(16) . ?
O2 C10 1.2078(14) . ?
O3 C12 1.4294(12) . ?
O3 C11 1.4490(14) . ?
O4 C13 1.1999(14) . ?
O5 C13 1.3296(14) . ?
O5 C14 1.4466(13) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C7 1.3855(16) . ?
C2 C3 1.3934(16) . ?
C3 C4 1.3833(14) . ?
C3 H3 0.9500 . ?
C4 C5 1.4017(14) . ?
C4 H4 0.9500 . ?
C5 C6 1.3858(15) . ?
C5 C8 1.5287(13) . ?
C6 C7 1.3975(14) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C13 1.5295(14) . ?
C8 C12 1.5309(14) . ?
C8 C9 1.5496(15) . ?
C9 C10 1.5135(15) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.4939(16) . ?
C11 C12 1.4721(15) . ?
C11 H11 1.0000 . ?
C12 H12 1.0000 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 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 O1 C1 116.95(9) . . ?
C12 O3 C11 61.51(7) . . ?
C13 O5 C14 115.92(9) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C7 124.75(10) . . ?
O1 C2 C3 115.47(10) . . ?
C7 C2 C3 119.78(10) . . ?
C4 C3 C2 119.98(10) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 121.24(10) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C6 C5 C4 117.86(9) . . ?
C6 C5 C8 123.22(9) . . ?
C4 C5 C8 118.92(9) . . ?
C5 C6 C7 121.55(10) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
C2 C7 C6 119.57(10) . . ?
C2 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
C5 C8 C13 108.99(8) . . ?
C5 C8 C12 112.71(8) . . ?
C13 C8 C12 108.03(8) . . ?
C5 C8 C9 112.23(8) . . ?
C13 C8 C9 111.11(8) . . ?
C12 C8 C9 103.64(8) . . ?
C10 C9 C8 106.01(8) . . ?
C10 C9 H9A 110.5 . . ?
C8 C9 H9A 110.5 . . ?
C10 C9 H9B 110.5 . . ?
C8 C9 H9B 110.5 . . ?
H9A C9 H9B 108.7 . . ?
O2 C10 C11 125.42(10) . . ?
O2 C10 C9 126.05(11) . . ?
C11 C10 C9 108.47(9) . . ?
O3 C11 C12 58.59(6) . . ?
O3 C11 C10 109.29(9) . . ?
C12 C11 C10 106.80(9) . . ?
O3 C11 H11 121.9 . . ?
C12 C11 H11 121.9 . . ?
C10 C11 H11 121.9 . . ?
O3 C12 C11 59.90(7) . . ?
O3 C12 C8 110.50(8) . . ?
C11 C12 C8 110.76(9) . . ?
O3 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C8 C12 H12 120.3 . . ?
O4 C13 O5 124.35(10) . . ?
O4 C13 C8 125.33(10) . . ?
O5 C13 C8 110.32(9) . . ?
O5 C14 H14A 109.5 . . ?
O5 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O5 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
C1 O1 C2 C7 2.70(17) . . . . ?
C1 O1 C2 C3 -177.46(11) . . . . ?
O1 C2 C3 C4 -178.66(10) . . . . ?
C7 C2 C3 C4 1.18(17) . . . . ?
C2 C3 C4 C5 0.13(18) . . . . ?
C3 C4 C5 C6 -1.58(16) . . . . ?
C3 C4 C5 C8 178.71(10) . . . . ?
C4 C5 C6 C7 1.76(16) . . . . ?
C8 C5 C6 C7 -178.54(10) . . . . ?
O1 C2 C7 C6 178.83(11) . . . . ?
C3 C2 C7 C6 -1.01(17) . . . . ?
C5 C6 C7 C2 -0.49(18) . . . . ?
C6 C5 C8 C13 -109.56(11) . . . . ?
C4 C5 C8 C13 70.13(12) . . . . ?
C6 C5 C8 C12 10.37(14) . . . . ?
C4 C5 C8 C12 -169.94(9) . . . . ?
C6 C5 C8 C9 126.93(11) . . . . ?
C4 C5 C8 C9 -53.38(12) . . . . ?
C5 C8 C9 C10 -102.35(9) . . . . ?
C13 C8 C9 C10 135.33(9) . . . . ?
C12 C8 C9 C10 19.54(10) . . . . ?
C8 C9 C10 O2 156.54(11) . . . . ?
C8 C9 C10 C11 -20.78(11) . . . . ?
C12 O3 C11 C10 98.35(9) . . . . ?
O2 C10 C11 O3 134.04(12) . . . . ?
C9 C10 C11 O3 -48.61(11) . . . . ?
O2 C10 C11 C12 -164.06(11) . . . . ?
C9 C10 C11 C12 13.28(11) . . . . ?
C11 O3 C12 C8 -102.75(10) . . . . ?
C10 C11 C12 O3 -102.71(9) . . . . ?
O3 C11 C12 C8 102.31(9) . . . . ?
C10 C11 C12 C8 -0.40(12) . . . . ?
C5 C8 C12 O3 174.02(8) . . . . ?
C13 C8 C12 O3 -65.50(11) . . . . ?
C9 C8 C12 O3 52.45(10) . . . . ?
C5 C8 C12 C11 109.54(10) . . . . ?
C13 C8 C12 C11 -129.98(9) . . . . ?
C9 C8 C12 C11 -12.03(11) . . . . ?
C14 O5 C13 O4 -1.83(16) . . . . ?
C14 O5 C13 C8 178.00(9) . . . . ?
C5 C8 C13 O4 -112.28(12) . . . . ?
C12 C8 C13 O4 124.94(11) . . . . ?
C9 C8 C13 O4 11.89(14) . . . . ?
C5 C8 C13 O5 67.89(11) . . . . ?
C12 C8 C13 O5 -54.89(11) . . . . ?
C9 C8 C13 O5 -167.94(8) . . . . ?

_refine_diff_density_max         0.345
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.057

