# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_exp_628
_database_code_depnum_ccdc_archive 'CCDC 1962911'
_audit_update_record             
;
2019-11-01 deposited with the CCDC.	2021-12-10 downloaded from the CCDC.
;
_audit_creation_date             2019-01-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H14 O3'
_chemical_formula_sum            'C12 H14 O3'
_chemical_formula_weight         206.23
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   17.7291(6)
_cell_length_b                   7.5614(2)
_cell_length_c                   8.1518(2)
_cell_angle_alpha                90
_cell_angle_beta                 102.867(3)
_cell_angle_gamma                90
_cell_volume                     1065.36(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9256
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      74.1980
_cell_measurement_theta_min      5.0940
_shelx_estimated_absorpt_T_max   0.915
_shelx_estimated_absorpt_T_min   0.714
_exptl_absorpt_coefficient_mu    0.751
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.01640
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1087
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            23666
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.334
_diffrn_reflns_theta_min         5.118
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -35.00  15.00   1.00    2.00    --    0.00 -29.00 -52.00   50
  2  ω      5.00  30.00   1.00    2.00    --    0.00  29.00 109.00   25
  3  ω     76.00 185.00   1.00    2.00    --   95.80  29.00 109.00  109
  4  ω     60.00  98.00   1.00    2.00    --   95.80 -29.00 -52.00   38
  5  ω     27.00  53.00   1.00    2.00    --    0.00  19.00 -60.00   26
  6  ω    -23.00  25.00   1.00    2.00    --    0.00  19.00  30.00   48
  7  ω     46.00  84.00   1.00    2.00    --    0.00  57.00 150.00   38
  8  ω    -28.00  88.00   1.00    2.00    --    0.00  77.00-180.00  116
  9  ω    -89.00 -56.00   1.00    2.00    --    0.00 -38.00-180.00   33
 10  ω    -21.00  54.00   1.00    2.00    --    0.00  57.00  60.00   75
 11  ω     43.00  85.00   1.00    2.00    --    0.00  57.00 -60.00   42
 12  ω     63.00  88.00   1.00    2.00    --    0.00  38.00 -90.00   25
 13  ω     10.00  56.00   1.00    2.00    --    0.00  38.00 -90.00   46
 14  ω     45.00  71.00   1.00    2.00    --    0.00  29.00 109.00   26
 15  ω    -24.00   4.00   1.00    2.00    --    0.00  19.00 -60.00   28
 16  ω     -1.00  25.00   1.00    2.00    --    0.00  57.00 -60.00   26
 17  ω    -21.00  41.00   1.00    2.00    --    0.00  57.00 150.00   62
 18  ω    -31.00  16.00   1.00    2.00    --    0.00 -38.00-180.00   47
 19  ω    155.00 181.00   1.00    2.00    --   95.80  80.00  76.30   26
 20  ω    104.00 130.00   1.00    2.00    --   95.80  80.00  76.30   26
 21  ω     75.00 184.00   1.00    2.00    --   95.80  45.00  60.00  109
 22  ω     66.00  92.00   1.00    2.00    --   95.80  80.00  76.30   26
 23  ω     64.00  90.00   1.00    2.00    --   95.80  82.00 120.00   26
 24  ω     67.00 125.00   1.00    2.00    --   95.80 -82.00  90.00   58
 25  ω     10.00  68.00   1.00    2.00    --   95.80 -82.00 -90.00   58
 26  ω      6.00 127.00   1.00    2.00    --   95.80 -82.00  60.00  121
 27  ω     71.00 130.00   1.00    2.00    --   95.80  61.00-105.87   59
 28  ω     65.00  91.00   1.00    2.00    --   95.80  77.00 -60.00   26
 29  ω     65.00  90.00   1.00    2.00    --   95.80  77.00-150.00   25
 30  ω     63.00 184.00   1.00    2.00    --   95.80  82.00 138.89  121
 31  ω     67.00  92.00   1.00    2.00    --   95.80  74.00 -29.91   25
 32  ω     69.00 126.00   1.00    2.00    --   95.80 -82.00 -30.00   57
 33  ω     68.00 137.00   1.00    2.00    --   95.80  70.00 125.90   69
 34  ω    142.00 177.00   1.00    2.00    --   95.80  70.00 125.90   35
 35  ω     93.00 125.00   1.00    2.00    --   95.80 -77.00-150.00   32
 36  ω     63.00 185.00   1.00    2.00    --   95.80  82.00 -30.00  122
 37  ω     14.00  87.00   1.00    2.00    --   95.80 -77.00-150.00   73
 38  ω     64.00  90.00   1.00    2.00    --   95.80  80.00 101.72   26
 39  ω     63.00  98.00   1.00    2.00    --   95.80  82.00  30.00   35
 40  ω     12.00  57.00   1.00    2.00    --   95.80 -82.00  90.00   45
 41  ω     65.00  90.00   1.00    2.00    --   95.80  77.00  90.00   25
 42  ω     68.00  94.00   1.00    2.00    --   95.80  74.00 -44.02   26
 43  ω    140.00 169.00   1.00    2.00    --   95.80  45.00 -30.00   29
 44  ω     75.00 141.00   1.00    2.00    --   95.80  61.00  30.00   66
 45  ω    158.00 183.00   1.00    2.00    --   95.80  61.00  30.00   25
 46  ω     71.00  97.00   1.00    2.00    --   95.80  61.00  90.00   26
 47  ω    146.00 172.00   1.00    2.00    --   95.80  61.00  90.00   26
 48  ω     65.00  90.00   1.00    2.00    --   95.80  77.00  30.00   25
 49  ω     65.00 130.00   1.00    2.00    --   95.80  76.00   0.00   65
 50  ω     75.00 152.00   1.00    2.00    --   95.80  45.00-120.00   77
 51  ω     64.00  90.00   1.00    2.00    --   95.80  82.00-150.00   26
 52  ω    140.00 176.00   1.00    2.00    --   95.80  61.00-105.87   36
 53  ω    135.00 182.00   1.00    2.00    --   95.80  82.00 -83.62   47
 54  ω     64.00  90.00   1.00    2.00    --   95.80  82.00  90.00   26
 55  ω     75.00 118.00   1.00    2.00    --   95.80  45.00 -30.00   43
 56  ω     64.00  90.00   1.00    2.00    --   95.80  82.00 -83.62   26
 57  ω     12.00 122.00   1.00    2.00    --   95.80 -82.00-180.00  110
 58  ω     66.00  92.00   1.00    2.00    --   95.80  77.00  60.00   26
 59  ω     65.00 156.00   1.00    2.00    --   95.80  77.00 -90.00   91
 60  ω     66.00  91.00   1.00    2.00    --   95.80  74.00 176.21   25
 61  ω     63.00 129.00   1.00    2.00    --   95.80  82.00-180.00   66
 62  ω     77.00 124.00   1.00    2.00    --   95.80 -82.00 -90.00   47
 63  ω     71.00  97.00   1.00    2.00    --   95.80  61.00-180.00   26
 64  ω     63.00  88.00   1.00    2.00    --   95.80  82.00-120.00   25
 65  ω     63.00  89.00   1.00    2.00    --   95.80  82.00   0.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0289235000
_diffrn_orient_matrix_UB_12      0.0058966000
_diffrn_orient_matrix_UB_13      0.1926488000
_diffrn_orient_matrix_UB_21      0.0153538000
_diffrn_orient_matrix_UB_22      0.1998463000
_diffrn_orient_matrix_UB_23      -0.0094283000
_diffrn_orient_matrix_UB_31      -0.0829276000
_diffrn_orient_matrix_UB_32      0.0390657000
_diffrn_orient_matrix_UB_33      0.0190480000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1824
_reflns_number_total             2147
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       0.021(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2147
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0499
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0873P)²+0.1134P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1432
_refine_ls_wR_factor_ref         0.1488
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C6(H6), C5(H5)
2.d Tetrahedral OH refined with riding coordinates:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.21268(6) 0.50182(13) 0.55433(12) 0.0484(3) Uani 1 1 d . . . . .
O2 O 0.40777(7) 0.42466(18) 0.00031(14) 0.0655(4) Uani 1 1 d . . . . .
H2 H 0.442850 0.433135 -0.049950 0.098 Uiso 1 1 calc R . . . .
O3 O 0.49355(7) 0.56914(19) 0.19555(14) 0.0690(4) Uani 1 1 d . . . . .
C1 C 0.26847(8) 0.50144(17) 0.46409(16) 0.0412(3) Uani 1 1 d . . . . .
C2 C 0.24713(9) 0.42853(18) 0.30356(18) 0.0466(4) Uani 1 1 d . . . . .
H2A H 0.197611 0.382885 0.265446 0.056 Uiso 1 1 calc R . . . .
C3 C 0.29940(9) 0.42395(18) 0.20100(17) 0.0468(4) Uani 1 1 d . . . . .
H3 H 0.285071 0.373814 0.094415 0.056 Uiso 1 1 calc R . . . .
C4 C 0.37345(8) 0.49382(18) 0.25579(17) 0.0434(4) Uani 1 1 d . . . . .
C6 C 0.34304(9) 0.5678(2) 0.52182(17) 0.0475(4) Uani 1 1 d . . . . .
H6 H 0.358165 0.613335 0.630173 0.057 Uiso 1 1 calc R . . . .
C5 C 0.39425(9) 0.5654(2) 0.41650(18) 0.0481(4) Uani 1 1 d . . . . .
H5 H 0.443536 0.612560 0.453859 0.058 Uiso 1 1 calc R . . . .
C7 C 0.23248(9) 0.5703(2) 0.72286(17) 0.0488(4) Uani 1 1 d . . . . .
H7A H 0.256724 0.685387 0.723253 0.059 Uiso 1 1 calc R . . . .
H7B H 0.268805 0.491586 0.794221 0.059 Uiso 1 1 calc R . . . .
C8 C 0.16015(9) 0.5862(2) 0.78879(18) 0.0509(4) Uani 1 1 d . . . . .
H8 H 0.174285 0.625519 0.906204 0.061 Uiso 1 1 calc R . . . .
C12 C 0.42859(8) 0.49525(19) 0.14443(17) 0.0484(4) Uani 1 1 d . . . . .
C9 C 0.09352(9) 0.7008(2) 0.6944(2) 0.0634(4) Uani 1 1 d . . . . .
H9A H 0.091451 0.817124 0.743388 0.076 Uiso 1 1 calc R . . . .
H9B H 0.090851 0.709091 0.574507 0.076 Uiso 1 1 calc R . . . .
C10 C 0.03639(10) 0.5692(2) 0.7402(2) 0.0639(5) Uani 1 1 d . . . . .
H10A H -0.005985 0.538466 0.647066 0.077 Uiso 1 1 calc R . . . .
H10B H 0.017538 0.602181 0.838893 0.077 Uiso 1 1 calc R . . . .
C11 C 0.10201(10) 0.4322(2) 0.7752(2) 0.0616(5) Uani 1 1 d . . . . .
H11A H 0.102127 0.352780 0.681754 0.074 Uiso 1 1 calc R . . . .
H11B H 0.105741 0.367096 0.879197 0.074 Uiso 1 1 calc R . . . .


_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 C1 1.3577(16) . ?
O1 C7 1.4368(16) . ?
O2 H2 0.8200 . ?
O2 C12 1.2681(17) . ?
O3 C12 1.2643(19) . ?
C1 C2 1.3925(19) . ?
C1 C6 1.394(2) . ?
C2 H2A 0.9300 . ?
C2 C3 1.380(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.393(2) . ?
C4 C5 1.3893(19) . ?
C4 C12 1.4747(19) . ?
C6 H6 0.9300 . ?
C6 C5 1.382(2) . ?
C5 H5 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.502(2) . ?
C8 H8 0.9800 . ?
C8 C9 1.528(2) . ?
C8 C11 1.543(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.524(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.537(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?

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
C1 O1 C7 117.80(11) . . ?
C12 O2 H2 109.5 . . ?
O1 C1 C2 115.58(12) . . ?
O1 C1 C6 124.52(12) . . ?
C2 C1 C6 119.90(13) . . ?
C1 C2 H2A 120.0 . . ?
C3 C2 C1 120.05(13) . . ?
C3 C2 H2A 120.0 . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.55(13) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 C12 120.79(13) . . ?
C5 C4 C3 118.90(13) . . ?
C5 C4 C12 120.30(13) . . ?
C1 C6 H6 120.3 . . ?
C5 C6 C1 119.36(13) . . ?
C5 C6 H6 120.3 . . ?
C4 C5 H5 119.4 . . ?
C6 C5 C4 121.20(14) . . ?
C6 C5 H5 119.4 . . ?
O1 C7 H7A 109.9 . . ?
O1 C7 H7B 109.9 . . ?
O1 C7 C8 108.95(12) . . ?
H7A C7 H7B 108.3 . . ?
C8 C7 H7A 109.9 . . ?
C8 C7 H7B 109.9 . . ?
C7 C8 H8 108.7 . . ?
C7 C8 C9 119.43(12) . . ?
C7 C8 C11 121.60(12) . . ?
C9 C8 H8 108.7 . . ?
C9 C8 C11 87.86(12) . . ?
C11 C8 H8 108.7 . . ?
O2 C12 C4 118.10(13) . . ?
O3 C12 O2 123.17(13) . . ?
O3 C12 C4 118.71(12) . . ?
C8 C9 H9A 113.8 . . ?
C8 C9 H9B 113.8 . . ?
H9A C9 H9B 111.0 . . ?
C10 C9 C8 89.31(13) . . ?
C10 C9 H9A 113.8 . . ?
C10 C9 H9B 113.8 . . ?
C9 C10 H10A 114.0 . . ?
C9 C10 H10B 114.0 . . ?
C9 C10 C11 88.20(12) . . ?
H10A C10 H10B 111.2 . . ?
C11 C10 H10A 114.0 . . ?
C11 C10 H10B 114.0 . . ?
C8 C11 H11A 113.9 . . ?
C8 C11 H11B 113.9 . . ?
C10 C11 C8 88.30(13) . . ?
C10 C11 H11A 113.9 . . ?
C10 C11 H11B 113.9 . . ?
H11A C11 H11B 111.1 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 40.965
_oxdiff_exptl_absorpt_empirical_full_min 0.225
