# Electronic Supplementary Material (ESI) for Green 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_z
_database_code_depnum_ccdc_archive 'CCDC 1573652'
_audit_update_record             
;
2017-09-11 deposited with the CCDC.
2018-05-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H14 O4'
_chemical_formula_weight         222.23

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   P2(1)/n

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                   5.8802(4)
_cell_length_b                   25.3608(19)
_cell_length_c                   8.2156(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.663(2)
_cell_angle_gamma                90.00
_cell_volume                     1153.72(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4141
_cell_measurement_theta_min      2.75
_cell_measurement_theta_max      26.05

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.32
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             472
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9554
_exptl_absorpt_correction_T_max  0.9699
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Smart Apex II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13133
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_sigmaI/netI    0.0172
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.61
_diffrn_reflns_theta_max         25.01
_reflns_number_total             2016
_reflns_number_gt                1631
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0545P)²+0.6003P] 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         2016
_refine_ls_number_parameters     145
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0629
_refine_ls_R_factor_gt           0.0514
_refine_ls_wR_factor_ref         0.1389
_refine_ls_wR_factor_gt          0.1301
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.050
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.1008(3) 0.11749(7) 0.7757(2) 0.0638(5) Uani 1 1 d . . .
O2 O 0.4152(3) 0.12326(10) 0.6883(2) 0.0896(7) Uani 1 1 d . . .
O3 O 0.7369(3) 0.02636(9) 1.2538(2) 0.0809(6) Uani 1 1 d . . .
O4 O 1.0670(2) 0.04360(7) 1.19219(19) 0.0599(5) Uani 1 1 d . . .
C1 C 0.4249(5) 0.15786(10) 1.2075(3) 0.0615(6) Uani 1 1 d . . .
H1A H 0.3048 0.1350 1.2144 0.074 Uiso 1 1 calc R . .
C2 C 0.4769(5) 0.20209(11) 1.3094(3) 0.0733(7) Uani 1 1 d . . .
H2A H 0.3909 0.2090 1.3837 0.088 Uiso 1 1 calc R . .
C3 C 0.6531(6) 0.23600(10) 1.3030(4) 0.0766(8) Uani 1 1 d . . .
H3A H 0.6883 0.2658 1.3730 0.092 Uiso 1 1 calc R . .
C4 C 0.7778(5) 0.22598(11) 1.1929(4) 0.0786(8) Uani 1 1 d . . .
H4A H 0.8976 0.2491 1.1875 0.094 Uiso 1 1 calc R . .
C5 C 0.7264(5) 0.18150(10) 1.0896(3) 0.0666(7) Uani 1 1 d . . .
H5A H 0.8126 0.1748 1.0155 0.080 Uiso 1 1 calc R . .
C6 C 0.5467(4) 0.14673(8) 1.0957(3) 0.0499(5) Uani 1 1 d U . .
C7 C 0.4793(4) 0.09731(9) 0.9813(3) 0.0490(5) Uani 1 1 d U . .
H7A H 0.3778 0.0748 1.0255 0.059 Uiso 1 1 calc R . .
C8 C 0.3331(4) 0.11328(9) 0.7974(3) 0.0492(5) Uani 1 1 d . . .
C9 C -0.0571(4) 0.13535(11) 0.6082(3) 0.0710(7) Uani 1 1 d . . .
H9A H -0.2204 0.1366 0.6079 0.106 Uiso 1 1 calc R . .
H9B H -0.0471 0.1114 0.5205 0.106 Uiso 1 1 calc R . .
H9C H -0.0083 0.1699 0.5853 0.106 Uiso 1 1 calc R . .
C10 C 0.6992(4) 0.06586(10) 0.9840(3) 0.0562(6) Uani 1 1 d . . .
H10A H 0.6493 0.0371 0.9017 0.067 Uiso 1 1 calc R . .
H10B H 0.8073 0.0884 0.9483 0.067 Uiso 1 1 calc R . .
C11 C 0.8305(4) 0.04406(8) 1.1581(3) 0.0476(5) Uani 1 1 d . . .
C12 C 1.2125(4) 0.02122(11) 1.3553(3) 0.0663(7) Uani 1 1 d . . .
H12A H 1.3799 0.0230 1.3656 0.099 Uiso 1 1 calc R . .
H12B H 1.1673 -0.0149 1.3610 0.099 Uiso 1 1 calc R . .
H12C H 1.1873 0.0407 1.4480 0.099 Uiso 1 1 calc R . .

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
O1 0.0436(9) 0.0862(12) 0.0580(10) 0.0193(8) 0.0122(7) 0.0090(8)
O2 0.0547(10) 0.163(2) 0.0512(10) 0.0292(11) 0.0184(8) 0.0054(11)
O3 0.0526(10) 0.1192(16) 0.0765(12) 0.0442(11) 0.0291(9) 0.0129(10)
O4 0.0404(8) 0.0840(12) 0.0538(9) 0.0169(8) 0.0140(7) 0.0018(7)
C1 0.0682(15) 0.0628(15) 0.0543(14) -0.0013(11) 0.0217(12) -0.0039(12)
C2 0.0865(19) 0.0709(18) 0.0620(16) -0.0099(13) 0.0241(14) 0.0093(15)
C3 0.098(2) 0.0527(15) 0.0603(16) -0.0065(12) 0.0017(15) 0.0020(15)
C4 0.0799(19) 0.0619(17) 0.0811(19) 0.0060(15) 0.0101(15) -0.0195(14)
C5 0.0718(16) 0.0643(16) 0.0662(15) 0.0049(13) 0.0267(13) -0.0040(13)
C6 0.0526(12) 0.0487(11) 0.0444(11) 0.0102(8) 0.0110(9) 0.0034(9)
C7 0.0450(11) 0.0547(12) 0.0477(12) 0.0076(8) 0.0164(9) 0.0024(9)
C8 0.0436(11) 0.0558(13) 0.0467(12) 0.0039(10) 0.0133(9) -0.0002(10)
C9 0.0526(14) 0.0876(19) 0.0593(15) 0.0154(13) 0.0011(11) 0.0061(13)
C10 0.0478(12) 0.0713(15) 0.0500(12) 0.0078(11) 0.0169(10) 0.0042(11)
C11 0.0428(11) 0.0520(12) 0.0487(12) 0.0041(10) 0.0166(9) 0.0010(9)
C12 0.0508(13) 0.0889(18) 0.0548(14) 0.0148(13) 0.0121(11) 0.0133(12)

_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 C8 1.321(3) . ?
O1 C9 1.449(3) . ?
O2 C8 1.180(3) . ?
O3 C11 1.189(2) . ?
O4 C11 1.323(2) . ?
O4 C12 1.442(3) . ?
C1 C6 1.370(3) . ?
C1 C2 1.371(4) . ?
C1 H1A 0.9300 . ?
C2 C3 1.361(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.366(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.383(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.390(3) . ?
C5 H5A 0.9300 . ?
C6 C7 1.537(3) . ?
C7 C10 1.513(3) . ?
C7 C8 1.520(3) . ?
C7 H7A 0.9800 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.485(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
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
C8 O1 C9 117.15(18) . . ?
C11 O4 C12 116.96(17) . . ?
C6 C1 C2 121.2(2) . . ?
C6 C1 H1A 119.4 . . ?
C2 C1 H1A 119.4 . . ?
C3 C2 C1 120.6(3) . . ?
C3 C2 H2A 119.7 . . ?
C1 C2 H2A 119.7 . . ?
C2 C3 C4 119.6(3) . . ?
C2 C3 H3A 120.2 . . ?
C4 C3 H3A 120.2 . . ?
C3 C4 C5 120.2(3) . . ?
C3 C4 H4A 119.9 . . ?
C5 C4 H4A 119.9 . . ?
C4 C5 C6 120.5(3) . . ?
C4 C5 H5A 119.8 . . ?
C6 C5 H5A 119.8 . . ?
C1 C6 C5 117.9(2) . . ?
C1 C6 C7 119.5(2) . . ?
C5 C6 C7 122.5(2) . . ?
C10 C7 C8 110.49(17) . . ?
C10 C7 C6 112.21(18) . . ?
C8 C7 C6 109.49(17) . . ?
C10 C7 H7A 108.2 . . ?
C8 C7 H7A 108.2 . . ?
C6 C7 H7A 108.2 . . ?
O2 C8 O1 123.3(2) . . ?
O2 C8 C7 124.9(2) . . ?
O1 C8 C7 111.68(18) . . ?
O1 C9 H9A 109.5 . . ?
O1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C7 112.03(18) . . ?
C11 C10 H10A 109.2 . . ?
C7 C10 H10A 109.2 . . ?
C11 C10 H10B 109.2 . . ?
C7 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
O3 C11 O4 122.9(2) . . ?
O3 C11 C10 124.86(19) . . ?
O4 C11 C10 112.10(17) . . ?
O4 C12 H12A 109.5 . . ?
O4 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O4 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
C6 C1 C2 C3 -0.5(4) . . . . ?
C1 C2 C3 C4 0.5(4) . . . . ?
C2 C3 C4 C5 -0.4(4) . . . . ?
C3 C4 C5 C6 0.4(4) . . . . ?
C2 C1 C6 C5 0.5(4) . . . . ?
C2 C1 C6 C7 -178.8(2) . . . . ?
C4 C5 C6 C1 -0.4(4) . . . . ?
C4 C5 C6 C7 178.9(2) . . . . ?
C1 C6 C7 C10 -133.0(2) . . . . ?
C5 C6 C7 C10 47.8(3) . . . . ?
C1 C6 C7 C8 104.0(2) . . . . ?
C5 C6 C7 C8 -75.3(3) . . . . ?
C9 O1 C8 O2 0.0(4) . . . . ?
C9 O1 C8 C7 176.7(2) . . . . ?
C10 C7 C8 O2 -33.2(3) . . . . ?
C6 C7 C8 O2 90.9(3) . . . . ?
C10 C7 C8 O1 150.2(2) . . . . ?
C6 C7 C8 O1 -85.8(2) . . . . ?
C8 C7 C10 C11 -173.11(18) . . . . ?
C6 C7 C10 C11 64.4(2) . . . . ?
C12 O4 C11 O3 -1.2(3) . . . . ?
C12 O4 C11 C10 -177.6(2) . . . . ?
C7 C10 C11 O3 39.3(3) . . . . ?
C7 C10 C11 O4 -144.5(2) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.034
