# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_1217_9_0m
_database_code_depnum_ccdc_archive 'CCDC 2106444'
loop_
_audit_author_name
_audit_author_address
'Bei Zhou'
;Southwest Forestry University
China
;
_audit_update_record             
;
2021-08-30 deposited with the CCDC.	2022-03-08 downloaded from the CCDC.
;
_audit_creation_date             2018-12-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H12 O3'
_chemical_formula_sum            'C15 H12 O3'
_chemical_formula_weight         240.25
_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                   8.9535(3)
_cell_length_b                   14.0575(5)
_cell_length_c                   9.4542(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.799(2)
_cell_angle_gamma                90
_cell_volume                     1189.83(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8248
_cell_measurement_temperature    149.44
_cell_measurement_theta_max      74.548
_cell_measurement_theta_min      4.940
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.763
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.3884
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1548 before and 0.1145 after correction. The Ratio of minimum to maximum transmission is 0.5153. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1052
_diffrn_reflns_av_unetI/netI     0.0626
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            19949
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.084
_diffrn_reflns_theta_min         4.940
_diffrn_ambient_temperature      149.44
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1848
_reflns_number_total             2335
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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         0.316
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.088
_refine_ls_extinction_coef       0.0119(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2335
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0826
_refine_ls_R_factor_gt           0.0669
_refine_ls_restrained_S_all      1.097
_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)+(0.0849P)²+0.6458P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1616
_refine_ls_wR_factor_ref         0.1745
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15)
;
_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 0.8939(2) 0.49043(12) 0.7079(2) 0.0479(5) Uani 1 1 d . . . . .
O2 O 0.75663(17) 0.39287(11) 0.50315(17) 0.0347(4) Uani 1 1 d . . . . .
O3 O 0.56060(17) 0.41426(11) 0.64571(18) 0.0383(5) Uani 1 1 d . . . . .
C1 C 0.6470(2) 0.36144(15) 0.5884(2) 0.0273(5) Uani 1 1 d . . . . .
C2 C 0.8489(2) 0.64542(15) 0.6204(2) 0.0281(5) Uani 1 1 d . . . . .
C3 C 0.6425(2) 0.25641(15) 0.6000(2) 0.0271(5) Uani 1 1 d . . . . .
C4 C 0.7644(2) 0.49509(15) 0.4893(2) 0.0314(5) Uani 1 1 d . . . . .
H4A H 0.662124 0.521073 0.478415 0.038 Uiso 1 1 calc R . . . .
H4B H 0.820477 0.511384 0.403055 0.038 Uiso 1 1 calc R . . . .
C5 C 0.8393(2) 0.53993(16) 0.6151(2) 0.0307(5) Uani 1 1 d . . . . .
C6 C 0.7624(2) 0.70365(16) 0.5318(2) 0.0325(5) Uani 1 1 d . . . . .
H6 H 0.695397 0.676147 0.464586 0.039 Uiso 1 1 calc R . . . .
C7 C 0.5478(2) 0.21645(16) 0.6991(2) 0.0325(5) Uani 1 1 d . . . . .
H7 H 0.490219 0.256266 0.758532 0.039 Uiso 1 1 calc R . . . .
C8 C 0.9473(2) 0.68659(16) 0.7176(2) 0.0349(5) Uani 1 1 d . . . . .
H8 H 1.006240 0.647309 0.778207 0.042 Uiso 1 1 calc R . . . .
C9 C 0.7266(3) 0.19760(16) 0.5133(2) 0.0335(5) Uani 1 1 d . . . . .
H9 H 0.792244 0.224708 0.446311 0.040 Uiso 1 1 calc R . . . .
C10 C 0.5376(3) 0.11827(16) 0.7111(3) 0.0366(6) Uani 1 1 d . . . . .
H10 H 0.473969 0.090914 0.779588 0.044 Uiso 1 1 calc R . . . .
C11 C 0.7748(3) 0.80202(17) 0.5424(3) 0.0383(6) Uani 1 1 d . . . . .
H11 H 0.714615 0.841738 0.483665 0.046 Uiso 1 1 calc R . . . .
C12 C 0.6198(3) 0.06020(16) 0.6236(3) 0.0374(6) Uani 1 1 d . . . . .
H12 H 0.611361 -0.006963 0.631221 0.045 Uiso 1 1 calc R . . . .
C13 C 0.8745(3) 0.84228(17) 0.6382(3) 0.0371(6) Uani 1 1 d . . . . .
H13 H 0.884432 0.909473 0.643506 0.045 Uiso 1 1 calc R . . . .
C14 C 0.7147(3) 0.09956(17) 0.5247(3) 0.0384(6) Uani 1 1 d . . . . .
H14 H 0.771304 0.059464 0.464864 0.046 Uiso 1 1 calc R . . . .
C15 C 0.9599(3) 0.78448(17) 0.7265(3) 0.0373(6) Uani 1 1 d . . . . .
H15 H 1.027225 0.812209 0.793184 0.045 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 C5 1.217(3) . ?
O2 C1 1.353(2) . ?
O2 C4 1.445(3) . ?
O3 C1 1.206(2) . ?
C1 C3 1.481(3) . ?
C2 C5 1.486(3) . ?
C2 C6 1.398(3) . ?
C2 C8 1.391(3) . ?
C3 C7 1.391(3) . ?
C3 C9 1.393(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.497(3) . ?
C6 H6 0.9500 . ?
C6 C11 1.391(3) . ?
C7 H7 0.9500 . ?
C7 C10 1.388(3) . ?
C8 H8 0.9500 . ?
C8 C15 1.383(3) . ?
C9 H9 0.9500 . ?
C9 C14 1.387(3) . ?
C10 H10 0.9500 . ?
C10 C12 1.382(3) . ?
C11 H11 0.9500 . ?
C11 C13 1.384(4) . ?
C12 H12 0.9500 . ?
C12 C14 1.387(3) . ?
C13 H13 0.9500 . ?
C13 C15 1.387(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?

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 O2 C4 114.53(16) . . ?
O2 C1 C3 112.97(17) . . ?
O3 C1 O2 122.79(19) . . ?
O3 C1 C3 124.22(19) . . ?
C6 C2 C5 122.2(2) . . ?
C8 C2 C5 118.24(19) . . ?
C8 C2 C6 119.6(2) . . ?
C7 C3 C1 118.03(18) . . ?
C7 C3 C9 119.8(2) . . ?
C9 C3 C1 122.19(19) . . ?
O2 C4 H4A 109.3 . . ?
O2 C4 H4B 109.3 . . ?
O2 C4 C5 111.60(17) . . ?
H4A C4 H4B 108.0 . . ?
C5 C4 H4A 109.3 . . ?
C5 C4 H4B 109.3 . . ?
O1 C5 C2 121.6(2) . . ?
O1 C5 C4 120.2(2) . . ?
C2 C5 C4 118.15(18) . . ?
C2 C6 H6 120.1 . . ?
C11 C6 C2 119.7(2) . . ?
C11 C6 H6 120.1 . . ?
C3 C7 H7 120.1 . . ?
C10 C7 C3 119.9(2) . . ?
C10 C7 H7 120.1 . . ?
C2 C8 H8 119.9 . . ?
C15 C8 C2 120.3(2) . . ?
C15 C8 H8 119.9 . . ?
C3 C9 H9 119.9 . . ?
C14 C9 C3 120.1(2) . . ?
C14 C9 H9 119.9 . . ?
C7 C10 H10 119.9 . . ?
C12 C10 C7 120.2(2) . . ?
C12 C10 H10 119.9 . . ?
C6 C11 H11 119.9 . . ?
C13 C11 C6 120.3(2) . . ?
C13 C11 H11 119.9 . . ?
C10 C12 H12 119.9 . . ?
C10 C12 C14 120.3(2) . . ?
C14 C12 H12 119.9 . . ?
C11 C13 H13 120.0 . . ?
C11 C13 C15 120.0(2) . . ?
C15 C13 H13 120.0 . . ?
C9 C14 C12 119.8(2) . . ?
C9 C14 H14 120.1 . . ?
C12 C14 H14 120.1 . . ?
C8 C15 C13 120.2(2) . . ?
C8 C15 H15 119.9 . . ?
C13 C15 H15 119.9 . . ?

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
O2 C1 C3 C7 171.59(18) . . . . ?
O2 C1 C3 C9 -10.0(3) . . . . ?
O2 C4 C5 O1 5.1(3) . . . . ?
O2 C4 C5 C2 -176.82(16) . . . . ?
O3 C1 C3 C7 -10.0(3) . . . . ?
O3 C1 C3 C9 168.4(2) . . . . ?
C1 O2 C4 C5 78.5(2) . . . . ?
C1 C3 C7 C10 178.5(2) . . . . ?
C1 C3 C9 C14 -177.7(2) . . . . ?
C2 C6 C11 C13 1.3(3) . . . . ?
C2 C8 C15 C13 -0.1(3) . . . . ?
C3 C7 C10 C12 -0.8(3) . . . . ?
C3 C9 C14 C12 -0.6(4) . . . . ?
C4 O2 C1 O3 1.6(3) . . . . ?
C4 O2 C1 C3 180.00(17) . . . . ?
C5 C2 C6 C11 179.33(19) . . . . ?
C5 C2 C8 C15 -179.9(2) . . . . ?
C6 C2 C5 O1 -166.8(2) . . . . ?
C6 C2 C5 C4 15.2(3) . . . . ?
C6 C2 C8 C15 -0.1(3) . . . . ?
C6 C11 C13 C15 -1.6(3) . . . . ?
C7 C3 C9 C14 0.7(3) . . . . ?
C7 C10 C12 C14 0.9(4) . . . . ?
C8 C2 C5 O1 13.1(3) . . . . ?
C8 C2 C5 C4 -164.93(19) . . . . ?
C8 C2 C6 C11 -0.5(3) . . . . ?
C9 C3 C7 C10 0.0(3) . . . . ?
C10 C12 C14 C9 -0.2(4) . . . . ?
C11 C13 C15 C8 0.9(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
