# Electronic Supplementary Material (ESI) for Green Chemistry.
# 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_exp_20367
_database_code_depnum_ccdc_archive 'CCDC 1906229'
loop_
_audit_author_name
_audit_author_address
'Long-Wu Ye'
;Xiamen University
China
;
_audit_update_record             
;
2019-03-28 deposited with the CCDC.	2019-05-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H12 O2'
_chemical_formula_weight         188.22

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                   6.7747(3)
_cell_length_b                   6.9936(2)
_cell_length_c                   10.2745(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.508(4)
_cell_angle_gamma                90
_cell_volume                     480.11(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3067
_cell_measurement_theta_min      4.3620
_cell_measurement_theta_max      67.684
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_F_000             200
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.706
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.72027
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4455
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.363
_diffrn_reflns_theta_max         67.684
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.840
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.840
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.834
_reflns_number_total             1453
_reflns_number_gt                1429
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.823
_reflns_Friedel_fraction_max     0.992
_reflns_Friedel_fraction_full    0.828

_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-2013 (Sheldrick, 2013)'
_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)+(0.0495P)²+0.0351P]
 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     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 634 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.08(13)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         1453
_refine_ls_number_parameters     127
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0308
_refine_ls_wR_factor_ref         0.0782
_refine_ls_wR_factor_gt          0.0776
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_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
O1 O 0.6533(2) 0.6432(3) 0.19042(15) 0.0333(4) Uani 1 1 d . . . . .
O2 O 0.5569(3) 0.3909(3) 0.07105(18) 0.0452(5) Uani 1 1 d . . . . .
C3 C 0.2791(3) 0.6574(3) 0.27402(19) 0.0224(5) Uani 1 1 d . . . . .
C9 C 0.1208(3) 0.6201(3) 0.3413(2) 0.0249(5) Uani 1 1 d . . . . .
H9 H 0.0167 0.5406 0.3038 0.030 Uiso 1 1 calc R U . . .
C2 C 0.2929(3) 0.5797(3) 0.13756(19) 0.0242(5) Uani 1 1 d . . . . .
H2 H 0.2562 0.6853 0.0756 0.029 Uiso 1 1 calc R U . . .
C1 C 0.5076(3) 0.5285(4) 0.1285(2) 0.0292(5) Uani 1 1 d . . . . .
C4 C 0.4338(3) 0.7757(3) 0.3317(2) 0.0255(5) Uani 1 1 d . . . . .
C10 C 0.1510(3) 0.4146(3) 0.0898(2) 0.0279(5) Uani 1 1 d . . . . .
H10A H 0.0144 0.4591 0.0851 0.033 Uiso 1 1 calc R U . . .
H10B H 0.1692 0.3802 0.0011 0.033 Uiso 1 1 calc R U . . .
C8 C 0.1187(4) 0.7015(3) 0.4639(2) 0.0296(6) Uani 1 1 d . . . . .
H8 H 0.0115 0.6782 0.5078 0.036 Uiso 1 1 calc R U . . .
C5 C 0.5957(4) 0.8158(3) 0.2529(2) 0.0329(6) Uani 1 1 d . . . . .
H5A H 0.5494 0.9105 0.1858 0.039 Uiso 1 1 calc R U . . .
H5B H 0.7113 0.8680 0.3103 0.039 Uiso 1 1 calc R U . . .
C6 C 0.4328(4) 0.8544(3) 0.4562(2) 0.0315(5) Uani 1 1 d . . . . .
H6 H 0.5381 0.9316 0.4950 0.038 Uiso 1 1 calc R U . . .
C11 C 0.1785(4) 0.2389(3) 0.1743(2) 0.0331(6) Uani 1 1 d . . . . .
H11 H 0.3085 0.1949 0.2010 0.040 Uiso 1 1 calc R U . . .
C12 C 0.0332(4) 0.1428(3) 0.2134(2) 0.0368(6) Uani 1 1 d . . . . .
H12A H -0.0987 0.1826 0.1886 0.044 Uiso 1 1 calc R U . . .
H12B H 0.0617 0.0348 0.2659 0.044 Uiso 1 1 calc R U . . .
C7 C 0.2744(4) 0.8170(3) 0.5216(2) 0.0331(6) Uani 1 1 d . . . . .
H7 H 0.2726 0.8697 0.6045 0.040 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
O1 C1 1.348(3) . ?
O1 C5 1.451(3) . ?
O2 C1 1.204(3) . ?
C3 C4 1.389(3) . ?
C3 C9 1.393(3) . ?
C3 C2 1.521(3) . ?
C9 C8 1.384(3) . ?
C2 C1 1.515(3) . ?
C2 C10 1.531(3) . ?
C4 C6 1.393(3) . ?
C4 C5 1.494(3) . ?
C10 C11 1.498(3) . ?
C8 C7 1.383(3) . ?
C6 C7 1.382(4) . ?
C11 C12 1.309(4) . ?

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 C5 118.34(17) . . ?
C4 C3 C9 119.25(19) . . ?
C4 C3 C2 116.66(17) . . ?
C9 C3 C2 124.07(19) . . ?
C8 C9 C3 119.9(2) . . ?
C1 C2 C3 110.33(17) . . ?
C1 C2 C10 111.11(18) . . ?
C3 C2 C10 115.71(17) . . ?
O2 C1 O1 117.7(2) . . ?
O2 C1 C2 124.5(2) . . ?
O1 C1 C2 117.8(2) . . ?
C3 C4 C6 120.6(2) . . ?
C3 C4 C5 116.81(19) . . ?
C6 C4 C5 122.6(2) . . ?
C11 C10 C2 114.92(18) . . ?
C7 C8 C9 120.6(2) . . ?
O1 C5 C4 111.01(18) . . ?
C7 C6 C4 119.6(2) . . ?
C12 C11 C10 124.8(2) . . ?
C6 C7 C8 120.0(2) . . ?

_refine_diff_density_max         0.133
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.045

_shelxl_version_number           2013-2


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane and ethyl acetate'
