# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_cu_160711_LS_AP127_L
_database_code_depnum_ccdc_archive 'CCDC 1813478'
_audit_update_record             
;
2017-12-26 deposited with the CCDC.
2019-02-01 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT089_cu_160711_LS_AP127_L 
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........ 7.32 Note
RESPONSE: The disorder observed in C8-C9-C10 residue increases the number
of parameters artificially and the complete dataset available gives
an apparetly low ratio of parameters per refined variable. 
;
_vrf_PLAT340_cu_160711_LS_AP127_L 
;
PROBLEM: Low Bond Precision on C-C Bonds ............... 0.00556 Ang.
RESPONSE: The quality of the available data was limited and did not
allowed for a better refinement of the structure.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H14 O4'
_chemical_formula_weight         234.24

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   8.9464(3)
_cell_length_b                   6.8743(2)
_cell_length_c                   9.9114(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.100(2)
_cell_angle_gamma                90
_cell_volume                     609.55(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    105
_cell_measurement_theta_min      26.11
_cell_measurement_theta_max      67.7

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_F_000             248
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.179
_exptl_crystal_size_mid          0.128
_exptl_crystal_size_min          0.042
_exptl_absorpt_coefficient_mu    0.785
_shelx_estimated_absorpt_T_min   0.872
_shelx_estimated_absorpt_T_max   0.968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.871
_exptl_absorpt_correction_T_max  0.968
_exptl_absorpt_process_details   'SADABS, Bruker 2013'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Incoatec I\ms Cu microsource'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω and \j scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            22280
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_av_R_equivalents  0.0626
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.461
_diffrn_reflns_theta_max         72.659
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2418
_reflns_number_gt                1940
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.835
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_fraction_full    1.000

_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 (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)+(0.0451P)²+0.1540P] 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     SHELXL
_refine_ls_extinction_coef       0.020(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 770 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.19(14)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         2418
_refine_ls_number_parameters     180
_refine_ls_number_restraints     35
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0471
_refine_ls_wR_factor_ref         0.1167
_refine_ls_wR_factor_gt          0.1093
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_restrained_S_all      1.201
_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
O3 O 0.5463(3) 0.6198(4) 0.8052(2) 0.0526(7) Uani 1 1 d . . . . .
C11 C 0.6033(4) 0.8098(6) 0.7809(4) 0.0517(9) Uani 1 1 d . . . . .
O4 O 0.5058(3) 0.8902(4) 0.6782(3) 0.0544(7) Uani 1 1 d . . . . .
C2 C 0.4252(4) 0.7368(5) 0.6169(3) 0.0418(8) Uani 1 1 d . . . . .
H2 H 0.4474 0.7365 0.5202 0.050 Uiso 1 1 calc R U . . .
C1 C 0.2566(4) 0.7632(5) 0.6351(4) 0.0438(8) Uani 1 1 d . . . . .
O2 O 0.2138(3) 0.9132(4) 0.5466(3) 0.0651(8) Uani 1 1 d . . . . .
H2A H 0.1229 0.9108 0.5360 0.098 Uiso 1 1 calc R U . . .
C6 C 0.1763(4) 0.5712(5) 0.5989(4) 0.0503(9) Uani 1 1 d . . . . .
O1 O 0.0615(3) 0.5774(5) 0.5340(3) 0.0755(9) Uani 1 1 d . . . . .
C5 C 0.2437(5) 0.3933(6) 0.6516(4) 0.0572(10) Uani 1 1 d . . . . .
H5 H 0.1865 0.2805 0.6556 0.069 Uiso 1 1 calc R U . . .
C4 C 0.3842(5) 0.3879(6) 0.6939(4) 0.0562(10) Uani 1 1 d . . . . .
H4 H 0.4186 0.2748 0.7351 0.067 Uiso 1 1 calc R U . . .
C3 C 0.4894(4) 0.5531(5) 0.6790(3) 0.0455(8) Uani 1 1 d . . . . .
H3 H 0.5738 0.5102 0.6236 0.055 Uiso 1 1 calc R U . . .
C7 C 0.2153(4) 0.8043(6) 0.7754(4) 0.0580(9) Uani 1 1 d D U . . .
C8 C 0.1717(12) 0.826(3) 0.8871(7) 0.0686(11) Uani 0.714(8) 1 d D U P A 1
C9 C 0.1641(7) 0.8782(11) 1.0308(6) 0.0740(14) Uani 0.714(8) 1 d D U P A 1
H9 H 0.2414 0.9469 1.0718 0.089 Uiso 0.714(8) 1 calc R U P A 1
C10 C 0.0479(8) 0.8263(14) 1.0986(7) 0.098(2) Uani 0.714(8) 1 d D U P A 1
H10A H -0.0286 0.7577 1.0565 0.118 Uiso 0.714(8) 1 calc R U P A 1
H10B H 0.0407 0.8576 1.1896 0.118 Uiso 0.714(8) 1 calc R U P A 1
C8B C 0.192(3) 0.836(7) 0.8923(13) 0.0686(11) Uani 0.286(8) 1 d D U P A 2
C9B C 0.0882(13) 0.839(3) 1.0068(11) 0.0727(18) Uani 0.286(8) 1 d D U P A 2
H9B H -0.0145 0.8339 0.9928 0.087 Uiso 0.286(8) 1 calc R U P A 2
C10B C 0.1424(19) 0.850(3) 1.1272(10) 0.079(3) Uani 0.286(8) 1 d D U P A 2
H10C H 0.2453 0.8559 1.1401 0.095 Uiso 0.286(8) 1 calc R U P A 2
H10D H 0.0786 0.8529 1.2012 0.095 Uiso 0.286(8) 1 calc R U P A 2
C13 C 0.7605(4) 0.8064(8) 0.7269(4) 0.0704(13) Uani 1 1 d . . . . .
H13A H 0.7655 0.7201 0.6510 0.106 Uiso 1 1 calc R U . . .
H13B H 0.8275 0.7619 0.7961 0.106 Uiso 1 1 calc R U . . .
H13C H 0.7887 0.9351 0.6993 0.106 Uiso 1 1 calc R U . . .
C12 C 0.5875(6) 0.9265(8) 0.9080(5) 0.0819(16) Uani 1 1 d . . . . .
H12A H 0.6198 1.0576 0.8918 0.123 Uiso 1 1 calc R U . . .
H12B H 0.6479 0.8696 0.9778 0.123 Uiso 1 1 calc R U . . .
H12C H 0.4847 0.9269 0.9357 0.123 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
O3 C11 1.422(5) . ?
O3 C3 1.425(4) . ?
C11 O4 1.449(4) . ?
C11 C12 1.500(6) . ?
C11 C13 1.506(5) . ?
O4 C2 1.414(4) . ?
C2 C3 1.517(5) . ?
C2 C1 1.530(5) . ?
C2 H2 0.9800 . ?
C1 O2 1.407(4) . ?
C1 C7 1.467(5) . ?
C1 C6 1.545(5) . ?
O2 H2A 0.8200 . ?
C6 O1 1.212(4) . ?
C6 C5 1.460(6) . ?
C5 C4 1.324(6) . ?
C5 H5 0.9300 . ?
C4 C3 1.483(5) . ?
C4 H4 0.9300 . ?
C3 H3 0.9800 . ?
C7 C8 1.184(6) . ?
C7 C8B 1.197(8) . ?
C8 C9 1.470(7) . ?
C9 C10 1.289(8) . ?
C9 H9 0.9300 . ?
C10 H10A 0.9300 . ?
C10 H10B 0.9300 . ?
C8B C9B 1.470(7) . ?
C9B C10B 1.289(8) . ?
C9B H9B 0.9300 . ?
C10B H10C 0.9300 . ?
C10B H10D 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 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
C11 O3 C3 105.9(3) . . ?
O3 C11 O4 104.7(3) . . ?
O3 C11 C12 108.3(3) . . ?
O4 C11 C12 109.2(3) . . ?
O3 C11 C13 112.4(3) . . ?
O4 C11 C13 108.5(3) . . ?
C12 C11 C13 113.3(4) . . ?
C2 O4 C11 108.9(3) . . ?
O4 C2 C3 104.7(3) . . ?
O4 C2 C1 111.3(3) . . ?
C3 C2 C1 115.1(3) . . ?
O4 C2 H2 108.5 . . ?
C3 C2 H2 108.5 . . ?
C1 C2 H2 108.5 . . ?
O2 C1 C7 112.4(3) . . ?
O2 C1 C2 106.3(3) . . ?
C7 C1 C2 112.6(3) . . ?
O2 C1 C6 110.9(3) . . ?
C7 C1 C6 105.5(3) . . ?
C2 C1 C6 109.3(3) . . ?
C1 O2 H2A 109.5 . . ?
O1 C6 C5 124.7(4) . . ?
O1 C6 C1 119.1(4) . . ?
C5 C6 C1 116.2(3) . . ?
C4 C5 C6 121.9(4) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C5 C4 C3 123.3(4) . . ?
C5 C4 H4 118.3 . . ?
C3 C4 H4 118.3 . . ?
O3 C3 C4 112.6(3) . . ?
O3 C3 C2 102.9(3) . . ?
C4 C3 C2 116.0(3) . . ?
O3 C3 H3 108.3 . . ?
C4 C3 H3 108.3 . . ?
C2 C3 H3 108.3 . . ?
C8 C7 C1 174.2(7) . . ?
C8B C7 C1 175.2(15) . . ?
C7 C8 C9 162.3(10) . . ?
C10 C9 C8 118.5(7) . . ?
C10 C9 H9 120.8 . . ?
C8 C9 H9 120.8 . . ?
C9 C10 H10A 120.0 . . ?
C9 C10 H10B 120.0 . . ?
H10A C10 H10B 120.0 . . ?
C7 C8B C9B 149(2) . . ?
C10B C9B C8B 118.6(7) . . ?
C10B C9B H9B 120.7 . . ?
C8B C9B H9B 120.7 . . ?
C9B C10B H10C 120.0 . . ?
C9B C10B H10D 120.0 . . ?
H10C C10B H10D 120.0 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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
C3 O3 C11 O4 33.3(3) . . . . ?
C3 O3 C11 C12 149.7(3) . . . . ?
C3 O3 C11 C13 -84.2(3) . . . . ?
O3 C11 O4 C2 -16.7(3) . . . . ?
C12 C11 O4 C2 -132.5(3) . . . . ?
C13 C11 O4 C2 103.5(4) . . . . ?
C11 O4 C2 C3 -5.2(3) . . . . ?
C11 O4 C2 C1 119.7(3) . . . . ?
O4 C2 C1 O2 74.2(3) . . . . ?
C3 C2 C1 O2 -166.9(3) . . . . ?
O4 C2 C1 C7 -49.3(4) . . . . ?
C3 C2 C1 C7 69.6(4) . . . . ?
O4 C2 C1 C6 -166.1(3) . . . . ?
C3 C2 C1 C6 -47.2(4) . . . . ?
O2 C1 C6 O1 -21.5(5) . . . . ?
C7 C1 C6 O1 100.4(4) . . . . ?
C2 C1 C6 O1 -138.3(3) . . . . ?
O2 C1 C6 C5 160.8(3) . . . . ?
C7 C1 C6 C5 -77.3(4) . . . . ?
C2 C1 C6 C5 44.0(4) . . . . ?
O1 C6 C5 C4 164.0(4) . . . . ?
C1 C6 C5 C4 -18.5(5) . . . . ?
C6 C5 C4 C3 -6.5(6) . . . . ?
C11 O3 C3 C4 -161.6(3) . . . . ?
C11 O3 C3 C2 -36.0(3) . . . . ?
C5 C4 C3 O3 120.8(4) . . . . ?
C5 C4 C3 C2 2.7(5) . . . . ?
O4 C2 C3 O3 25.0(3) . . . . ?
C1 C2 C3 O3 -97.5(3) . . . . ?
O4 C2 C3 C4 148.4(3) . . . . ?
C1 C2 C3 C4 25.9(4) . . . . ?
C8B C7 C8 C9 4(14) . . . . ?
C7 C8 C9 C10 -173(5) . . . . ?
C8 C7 C8B C9B -2(12) . . . . ?
C7 C8B C9B C10B 164(7) . . . . ?

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
O2 H2A O1 0.82 2.12 2.823(4) 143.2 2_556
O2 H2A O1 0.82 2.36 2.684(4) 104.6 .

_refine_diff_density_max         0.172
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.042

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane/dichloromethane'
