# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_MS380
_database_code_depnum_ccdc_archive 'CCDC 1991823'
loop_
_audit_author_name
_audit_author_address
'Ha Jin Lee'
;Yeungnam University
South Korea
;
_audit_update_record             
;
2020-03-21 deposited with the CCDC.	2020-06-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
3-(2-hydroxy-5-methylbenzoyl)-5-methylbenzaldehyde
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H14 O3'
_chemical_formula_sum            'C16 H14 O3'
_chemical_formula_weight         254.27

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.6722(4)
_cell_length_b                   21.2561(6)
_cell_length_c                   8.9159(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.8770(10)
_cell_angle_gamma                90
_cell_volume                     2577.50(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    9214
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      28.27

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_F_000             1072
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.444
_exptl_crystal_size_mid          0.262
_exptl_crystal_size_min          0.114
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   0.961
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.7191
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'PHOTON II M14'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            81761
_diffrn_reflns_av_unetI/netI     0.0130
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.778
_diffrn_reflns_theta_max         28.317
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             6382
_reflns_number_gt                5473
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0716P)²+0.9736P] 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_number_reflns         6382
_refine_ls_number_parameters     349
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0499
_refine_ls_wR_factor_ref         0.1507
_refine_ls_wR_factor_gt          0.1428
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.001
_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
C1 C 0.37484(10) 0.58360(6) 0.89366(15) 0.0314(3) Uani 1 1 d . . . . .
O1 O 0.36604(9) 0.57605(5) 1.02925(11) 0.0439(3) Uani 1 1 d . . . . .
C2 C 0.37799(9) 0.52988(6) 0.79052(15) 0.0290(3) Uani 1 1 d . . . . .
C3 C 0.38646(10) 0.46848(7) 0.84892(17) 0.0353(3) Uani 1 1 d . . . . .
C4 C 0.38979(12) 0.41798(7) 0.7500(2) 0.0442(4) Uani 1 1 d . . . . .
H4 H 0.3964 0.3769 0.7885 0.053 Uiso 1 1 calc R U . . .
C5 C 0.38353(11) 0.42748(7) 0.59715(19) 0.0412(3) Uani 1 1 d . . . . .
H5 H 0.3871 0.3927 0.5329 0.049 Uiso 1 1 calc R U . . .
C6 C 0.37204(9) 0.48766(7) 0.53446(16) 0.0330(3) Uani 1 1 d . . . . .
C7 C 0.36929(9) 0.53757(6) 0.63291(15) 0.0294(3) Uani 1 1 d . . . . .
H7 H 0.3613 0.5784 0.5931 0.035 Uiso 1 1 calc R U . . .
O2 O 0.39103(10) 0.45607(6) 0.99814(13) 0.0500(3) Uani 1 1 d . . . . .
H2 H 0.3846 0.4893 1.0451 0.075 Uiso 1 1 calc R U . . .
C8 C 0.36289(11) 0.49716(8) 0.36645(17) 0.0434(4) Uani 1 1 d . . . . .
H8A H 0.3315 0.5373 0.3418 0.065 Uiso 1 1 calc R U . . .
H8B H 0.3234 0.4636 0.3177 0.065 Uiso 1 1 calc R U . . .
H8C H 0.4278 0.4967 0.3315 0.065 Uiso 1 1 calc R U . . .
C9 C 0.38231(10) 0.64959(6) 0.83752(14) 0.0308(3) Uani 1 1 d . . . . .
C10 C 0.31861(10) 0.69499(7) 0.88611(15) 0.0336(3) Uani 1 1 d . . . . .
H10 H 0.2706 0.6828 0.9486 0.040 Uiso 1 1 calc R U . . .
C11 C 0.32474(11) 0.75788(7) 0.84386(16) 0.0361(3) Uani 1 1 d . . . . .
C12 C 0.39686(11) 0.77464(7) 0.75208(16) 0.0368(3) Uani 1 1 d . . . . .
H12 H 0.4018 0.8167 0.7213 0.044 Uiso 1 1 calc R U . . .
C13 C 0.46192(11) 0.73011(6) 0.70505(15) 0.0342(3) Uani 1 1 d . . . . .
C14 C 0.45514(10) 0.66724(6) 0.74792(15) 0.0324(3) Uani 1 1 d . . . . .
H14 H 0.4993 0.6372 0.7166 0.039 Uiso 1 1 calc R U . . .
C15 C 0.25631(13) 0.80597(8) 0.9011(2) 0.0501(4) Uani 1 1 d . . . . .
H15A H 0.2795 0.8172 1.0041 0.075 Uiso 1 1 calc R U . . .
H15B H 0.1907 0.7884 0.8980 0.075 Uiso 1 1 calc R U . . .
H15C H 0.2548 0.8432 0.8380 0.075 Uiso 1 1 calc R U . . .
C16 C 0.53708(12) 0.74941(7) 0.60673(17) 0.0421(3) Uani 1 1 d . . . . .
H16 H 0.5358 0.7913 0.5726 0.051 Uiso 1 1 calc R U . . .
O3 O 0.59964(10) 0.71547(7) 0.56731(17) 0.0629(4) Uani 1 1 d . . . . .
C17 C 0.13420(9) 0.41274(6) 0.55810(14) 0.0290(3) Uani 1 1 d . . . . .
O4 O 0.14693(8) 0.41419(5) 0.42265(11) 0.0390(2) Uani 1 1 d . . . . .
C18 C 0.12951(9) 0.47085(6) 0.64645(14) 0.0271(3) Uani 1 1 d . . . . .
C19 C 0.12031(10) 0.52906(6) 0.57102(16) 0.0317(3) Uani 1 1 d . . . . .
C20 C 0.11148(11) 0.58383(7) 0.65408(19) 0.0412(3) Uani 1 1 d . . . . .
H20 H 0.1038 0.6227 0.6042 0.049 Uiso 1 1 calc R U . . .
C21 C 0.11396(11) 0.58150(7) 0.80878(19) 0.0418(3) Uani 1 1 d . . . . .
H21 H 0.1064 0.6189 0.8626 0.050 Uiso 1 1 calc R U . . .
C22 C 0.12745(10) 0.52459(7) 0.88811(16) 0.0352(3) Uani 1 1 d . . . . .
C23 C 0.13495(9) 0.47043(6) 0.80462(15) 0.0305(3) Uani 1 1 d . . . . .
H23 H 0.1440 0.4318 0.8555 0.037 Uiso 1 1 calc R U . . .
O5 O 0.11859(9) 0.53470(5) 0.42006(12) 0.0418(3) Uani 1 1 d . . . . .
H5A H 0.1261 0.4995 0.3824 0.063 Uiso 1 1 calc R U . . .
C24 C 0.13284(13) 0.52279(9) 1.05762(18) 0.0491(4) Uani 1 1 d . . . . .
H24A H 0.0676 0.5290 1.0889 0.074 Uiso 1 1 calc R U . . .
H24B H 0.1762 0.5559 1.0995 0.074 Uiso 1 1 calc R U . . .
H24C H 0.1581 0.4823 1.0936 0.074 Uiso 1 1 calc R U . . .
C25 C 0.12094(10) 0.34982(6) 0.62896(14) 0.0293(3) Uani 1 1 d . . . . .
C26 C 0.18075(10) 0.30009(6) 0.59173(15) 0.0330(3) Uani 1 1 d . . . . .
H26 H 0.2308 0.3077 0.5291 0.040 Uiso 1 1 calc R U . . .
C27 C 0.16788(11) 0.23943(6) 0.64530(16) 0.0352(3) Uani 1 1 d . . . . .
C28 C 0.09304(11) 0.22950(6) 0.73751(16) 0.0357(3) Uani 1 1 d . . . . .
H28 H 0.0830 0.1889 0.7748 0.043 Uiso 1 1 calc R U . . .
C29 C 0.03296(10) 0.27853(6) 0.77548(15) 0.0326(3) Uani 1 1 d . . . . .
C30 C 0.04603(10) 0.33907(6) 0.72049(15) 0.0304(3) Uani 1 1 d . . . . .
H30 H 0.0048 0.3721 0.7449 0.037 Uiso 1 1 calc R U . . .
C31 C 0.23198(14) 0.18595(8) 0.6022(2) 0.0512(4) Uani 1 1 d . . . . .
H31A H 0.2123 0.1474 0.6490 0.077 Uiso 1 1 calc R U . . .
H31B H 0.3001 0.1951 0.6364 0.077 Uiso 1 1 calc R U . . .
H31C H 0.2247 0.1810 0.4935 0.077 Uiso 1 1 calc R U . . .
C32 C -0.04289(13) 0.26624(7) 0.87822(18) 0.0423(3) Uani 1 1 d . . . . .
H32 H -0.0480 0.2249 0.9141 0.051 Uiso 1 1 calc R U . . .
O6 O -0.09868(10) 0.30462(6) 0.91981(15) 0.0558(3) Uani 1 1 d . . . . .


_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
C1 O1 1.2375(16) . ?
C1 C2 1.4695(18) . ?
C1 C9 1.4961(18) . ?
C2 C3 1.4055(18) . ?
C2 C7 1.4076(18) . ?
C3 O2 1.3515(18) . ?
C3 C4 1.393(2) . ?
C4 C5 1.372(2) . ?
C4 H4 0.9400 . ?
C5 C6 1.398(2) . ?
C5 H5 0.9400 . ?
C6 C7 1.3800(18) . ?
C6 C8 1.504(2) . ?
C7 H7 0.9400 . ?
O2 H2 0.8300 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 H8C 0.9700 . ?
C9 C14 1.3904(18) . ?
C9 C10 1.3982(18) . ?
C10 C11 1.394(2) . ?
C10 H10 0.9400 . ?
C11 C12 1.391(2) . ?
C11 C15 1.509(2) . ?
C12 C13 1.393(2) . ?
C12 H12 0.9400 . ?
C13 C14 1.3956(19) . ?
C13 C16 1.476(2) . ?
C14 H14 0.9400 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 H15C 0.9700 . ?
C16 O3 1.199(2) . ?
C16 H16 0.9400 . ?
C17 O4 1.2380(16) . ?
C17 C18 1.4700(17) . ?
C17 C25 1.4980(17) . ?
C18 C23 1.4045(18) . ?
C18 C19 1.4078(17) . ?
C19 O5 1.3490(17) . ?
C19 C20 1.392(2) . ?
C20 C21 1.377(2) . ?
C20 H20 0.9400 . ?
C21 C22 1.404(2) . ?
C21 H21 0.9400 . ?
C22 C23 1.3805(18) . ?
C22 C24 1.506(2) . ?
C23 H23 0.9400 . ?
O5 H5A 0.8300 . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 H24C 0.9700 . ?
C25 C30 1.3923(18) . ?
C25 C26 1.3971(18) . ?
C26 C27 1.3925(19) . ?
C26 H26 0.9400 . ?
C27 C28 1.393(2) . ?
C27 C31 1.509(2) . ?
C28 C29 1.390(2) . ?
C28 H28 0.9400 . ?
C29 C30 1.3951(18) . ?
C29 C32 1.476(2) . ?
C30 H30 0.9400 . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C31 H31C 0.9700 . ?
C32 O6 1.201(2) . ?
C32 H32 0.9400 . ?

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
O1 C1 C2 121.50(12) . . ?
O1 C1 C9 117.72(12) . . ?
C2 C1 C9 120.78(11) . . ?
C3 C2 C7 118.23(12) . . ?
C3 C2 C1 119.76(12) . . ?
C7 C2 C1 121.98(12) . . ?
O2 C3 C4 118.12(13) . . ?
O2 C3 C2 122.67(13) . . ?
C4 C3 C2 119.21(13) . . ?
C5 C4 C3 120.84(14) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 121.66(13) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C7 C6 C5 117.28(13) . . ?
C7 C6 C8 121.69(13) . . ?
C5 C6 C8 121.03(13) . . ?
C6 C7 C2 122.73(12) . . ?
C6 C7 H7 118.6 . . ?
C2 C7 H7 118.6 . . ?
C3 O2 H2 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C14 C9 C10 119.81(13) . . ?
C14 C9 C1 121.51(12) . . ?
C10 C9 C1 118.51(12) . . ?
C11 C10 C9 121.45(13) . . ?
C11 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C12 C11 C10 118.07(13) . . ?
C12 C11 C15 121.80(14) . . ?
C10 C11 C15 120.10(14) . . ?
C11 C12 C13 121.08(13) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C12 C13 C14 120.40(13) . . ?
C12 C13 C16 119.67(13) . . ?
C14 C13 C16 119.92(13) . . ?
C9 C14 C13 119.17(13) . . ?
C9 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C11 C15 H15A 109.5 . . ?
C11 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C11 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O3 C16 C13 124.61(15) . . ?
O3 C16 H16 117.7 . . ?
C13 C16 H16 117.7 . . ?
O4 C17 C18 121.33(11) . . ?
O4 C17 C25 117.96(11) . . ?
C18 C17 C25 120.69(11) . . ?
C23 C18 C19 118.57(12) . . ?
C23 C18 C17 122.14(11) . . ?
C19 C18 C17 119.29(12) . . ?
O5 C19 C20 117.58(12) . . ?
O5 C19 C18 123.12(12) . . ?
C20 C19 C18 119.30(13) . . ?
C21 C20 C19 120.56(14) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C20 C21 C22 121.60(13) . . ?
C20 C21 H21 119.2 . . ?
C22 C21 H21 119.2 . . ?
C23 C22 C21 117.39(13) . . ?
C23 C22 C24 121.41(14) . . ?
C21 C22 C24 121.19(13) . . ?
C22 C23 C18 122.47(13) . . ?
C22 C23 H23 118.8 . . ?
C18 C23 H23 118.8 . . ?
C19 O5 H5A 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C30 C25 C26 119.91(12) . . ?
C30 C25 C17 121.45(12) . . ?
C26 C25 C17 118.44(12) . . ?
C27 C26 C25 121.44(13) . . ?
C27 C26 H26 119.3 . . ?
C25 C26 H26 119.3 . . ?
C26 C27 C28 117.97(13) . . ?
C26 C27 C31 120.87(14) . . ?
C28 C27 C31 121.15(13) . . ?
C29 C28 C27 121.22(12) . . ?
C29 C28 H28 119.4 . . ?
C27 C28 H28 119.4 . . ?
C28 C29 C30 120.39(13) . . ?
C28 C29 C32 119.26(12) . . ?
C30 C29 C32 120.32(13) . . ?
C25 C30 C29 119.06(12) . . ?
C25 C30 H30 120.5 . . ?
C29 C30 H30 120.5 . . ?
C27 C31 H31A 109.5 . . ?
C27 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C27 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
O6 C32 C29 125.47(14) . . ?
O6 C32 H32 117.3 . . ?
C29 C32 H32 117.3 . . ?

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
O1 C1 C2 C3 -9.9(2) . . . . ?
C9 C1 C2 C3 170.00(12) . . . . ?
O1 C1 C2 C7 167.78(13) . . . . ?
C9 C1 C2 C7 -12.27(19) . . . . ?
C7 C2 C3 O2 -177.17(12) . . . . ?
C1 C2 C3 O2 0.6(2) . . . . ?
C7 C2 C3 C4 2.5(2) . . . . ?
C1 C2 C3 C4 -179.73(13) . . . . ?
O2 C3 C4 C5 178.73(14) . . . . ?
C2 C3 C4 C5 -0.9(2) . . . . ?
C3 C4 C5 C6 -1.0(2) . . . . ?
C4 C5 C6 C7 1.3(2) . . . . ?
C4 C5 C6 C8 -178.54(14) . . . . ?
C5 C6 C7 C2 0.32(19) . . . . ?
C8 C6 C7 C2 -179.81(12) . . . . ?
C3 C2 C7 C6 -2.2(2) . . . . ?
C1 C2 C7 C6 -179.96(12) . . . . ?
O1 C1 C9 C14 131.50(14) . . . . ?
C2 C1 C9 C14 -48.45(18) . . . . ?
O1 C1 C9 C10 -43.84(18) . . . . ?
C2 C1 C9 C10 136.22(13) . . . . ?
C14 C9 C10 C11 1.5(2) . . . . ?
C1 C9 C10 C11 176.93(12) . . . . ?
C9 C10 C11 C12 -0.4(2) . . . . ?
C9 C10 C11 C15 -178.63(13) . . . . ?
C10 C11 C12 C13 -0.8(2) . . . . ?
C15 C11 C12 C13 177.45(14) . . . . ?
C11 C12 C13 C14 0.8(2) . . . . ?
C11 C12 C13 C16 179.54(13) . . . . ?
C10 C9 C14 C13 -1.4(2) . . . . ?
C1 C9 C14 C13 -176.72(12) . . . . ?
C12 C13 C14 C9 0.3(2) . . . . ?
C16 C13 C14 C9 -178.41(13) . . . . ?
C12 C13 C16 O3 175.63(16) . . . . ?
C14 C13 C16 O3 -5.6(2) . . . . ?
O4 C17 C18 C23 -166.96(13) . . . . ?
C25 C17 C18 C23 14.69(19) . . . . ?
O4 C17 C18 C19 12.35(19) . . . . ?
C25 C17 C18 C19 -166.00(12) . . . . ?
C23 C18 C19 O5 177.19(12) . . . . ?
C17 C18 C19 O5 -2.1(2) . . . . ?
C23 C18 C19 C20 -3.49(19) . . . . ?
C17 C18 C19 C20 177.17(12) . . . . ?
O5 C19 C20 C21 -179.15(13) . . . . ?
C18 C19 C20 C21 1.5(2) . . . . ?
C19 C20 C21 C22 1.4(2) . . . . ?
C20 C21 C22 C23 -2.1(2) . . . . ?
C20 C21 C22 C24 178.30(14) . . . . ?
C21 C22 C23 C18 0.0(2) . . . . ?
C24 C22 C23 C18 179.57(13) . . . . ?
C19 C18 C23 C22 2.8(2) . . . . ?
C17 C18 C23 C22 -177.88(12) . . . . ?
O4 C17 C25 C30 -133.28(14) . . . . ?
C18 C17 C25 C30 45.13(18) . . . . ?
O4 C17 C25 C26 41.65(18) . . . . ?
C18 C17 C25 C26 -139.95(13) . . . . ?
C30 C25 C26 C27 -0.5(2) . . . . ?
C17 C25 C26 C27 -175.56(12) . . . . ?
C25 C26 C27 C28 0.1(2) . . . . ?
C25 C26 C27 C31 179.02(14) . . . . ?
C26 C27 C28 C29 -0.1(2) . . . . ?
C31 C27 C28 C29 -179.01(14) . . . . ?
C27 C28 C29 C30 0.5(2) . . . . ?
C27 C28 C29 C32 -177.67(13) . . . . ?
C26 C25 C30 C29 0.93(19) . . . . ?
C17 C25 C30 C29 175.78(12) . . . . ?
C28 C29 C30 C25 -0.9(2) . . . . ?
C32 C29 C30 C25 177.26(12) . . . . ?
C28 C29 C32 O6 179.60(16) . . . . ?
C30 C29 C32 O6 1.4(2) . . . . ?

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
O5 H5A O4 0.83 1.87 2.5905(15) 145.1 .
O2 H2 O1 0.83 1.87 2.5919(17) 145.5 .

_refine_diff_density_max         0.297
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.042


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane/EtOAc'
####################################################################### 
# 
# 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_MS422
_database_code_depnum_ccdc_archive 'CCDC 1991825'
loop_
_audit_author_name
_audit_author_address
'Ha Jin Lee'
;Yeungnam University
South Korea
;
_audit_update_record             
;
2020-03-21 deposited with the CCDC.	2020-06-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
3-(2-hydroxy-5-methylbenzoyl)-1-naphthaldehyde
_chemical_name_common            ?
_chemical_melting_point          445
_chemical_formula_moiety         'C19 H14 O3'
_chemical_formula_sum            'C19 H14 O3'
_chemical_formula_weight         290.30

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.3618(3)
_cell_length_b                   7.4104(2)
_cell_length_c                   25.4612(9)
_cell_angle_alpha                90
_cell_angle_beta                 95.2808(14)
_cell_angle_gamma                90
_cell_volume                     1383.11(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    9905
_cell_measurement_theta_min      2.86
_cell_measurement_theta_max      28.36

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.259
_exptl_crystal_size_mid          0.248
_exptl_crystal_size_min          0.166
_exptl_absorpt_coefficient_mu    0.094
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.7171
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'PHOTON II M14'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            42946
_diffrn_reflns_av_unetI/netI     0.0159
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         2.864
_diffrn_reflns_theta_max         28.591
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             3455
_reflns_number_gt                2986
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0452P)²+0.7069P] 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_number_reflns         3455
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0429
_refine_ls_wR_factor_ref         0.1157
_refine_ls_wR_factor_gt          0.1088
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.001
_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
C1 C 0.54885(18) 0.65219(18) 0.82189(5) 0.0277(3) Uani 1 1 d . . . . .
C2 C 0.42381(17) 0.53508(16) 0.84317(5) 0.0231(2) Uani 1 1 d . . . . .
C3 C 0.24993(17) 0.51379(16) 0.81645(5) 0.0237(2) Uani 1 1 d . . . . .
H3 H 0.1653 0.4380 0.8310 0.028 Uiso 1 1 calc R U . . .
C4 C 0.19890(18) 0.60118(17) 0.76915(5) 0.0268(3) Uani 1 1 d . . . . .
C5 C 0.3282(2) 0.71251(18) 0.74855(5) 0.0307(3) Uani 1 1 d . . . . .
H5 H 0.2974 0.7718 0.7163 0.037 Uiso 1 1 calc R U . . .
C6 C 0.4998(2) 0.73784(19) 0.77421(5) 0.0321(3) Uani 1 1 d . . . . .
H6 H 0.5839 0.8134 0.7593 0.039 Uiso 1 1 calc R U . . .
O1 O 0.71840(14) 0.68513(17) 0.84573(4) 0.0418(3) Uani 1 1 d . . . . .
H1 H 0.7290 0.6369 0.8753 0.063 Uiso 1 1 calc R U . . .
C7 C 0.47246(17) 0.44822(17) 0.89484(5) 0.0243(3) Uani 1 1 d . . . . .
O2 O 0.58758(14) 0.51725(14) 0.92683(4) 0.0342(2) Uani 1 1 d . . . . .
C8 C 0.38561(17) 0.27432(17) 0.90823(5) 0.0237(2) Uani 1 1 d . . . . .
C9 C 0.35614(17) 0.24128(17) 0.96013(5) 0.0245(3) Uani 1 1 d . . . . .
H9 H 0.3835 0.3310 0.9857 0.029 Uiso 1 1 calc R U . . .
C10 C 0.28532(16) 0.07384(17) 0.97508(5) 0.0237(2) Uani 1 1 d . . . . .
C11 C 0.25183(17) 0.03739(18) 1.02803(5) 0.0267(3) Uani 1 1 d . . . . .
H11 H 0.2760 0.1267 1.0540 0.032 Uiso 1 1 calc R U . . .
C12 C 0.18454(17) -0.12673(19) 1.04175(5) 0.0281(3) Uani 1 1 d . . . . .
C13 C 0.14792(18) -0.26293(19) 1.00323(6) 0.0309(3) Uani 1 1 d . . . . .
H13 H 0.1025 -0.3753 1.0131 0.037 Uiso 1 1 calc R U . . .
C14 C 0.17807(19) -0.23212(18) 0.95196(5) 0.0296(3) Uani 1 1 d . . . . .
H14 H 0.1527 -0.3233 0.9267 0.036 Uiso 1 1 calc R U . . .
C15 C 0.24774(17) -0.06290(17) 0.93636(5) 0.0247(3) Uani 1 1 d . . . . .
C16 C 0.28132(18) -0.02588(17) 0.88358(5) 0.0273(3) Uani 1 1 d . . . . .
H16 H 0.2579 -0.1153 0.8577 0.033 Uiso 1 1 calc R U . . .
C17 C 0.34743(18) 0.13827(17) 0.86974(5) 0.0265(3) Uani 1 1 d . . . . .
H17 H 0.3677 0.1609 0.8344 0.032 Uiso 1 1 calc R U . . .
C18 C 0.0133(2) 0.5749(2) 0.74037(6) 0.0387(3) Uani 1 1 d . . . . .
H18A H 0.0102 0.4612 0.7214 0.058 Uiso 1 1 calc R U . . .
H18B H -0.0123 0.6731 0.7156 0.058 Uiso 1 1 calc R U . . .
H18C H -0.0780 0.5735 0.7655 0.058 Uiso 1 1 calc R U . . .
C19 C 0.1516(2) -0.1583(2) 1.09731(6) 0.0358(3) Uani 1 1 d . . . . .
H19 H 0.1747 -0.0624 1.1211 0.043 Uiso 1 1 calc R U . . .
O3 O 0.09693(17) -0.29870(17) 1.11449(5) 0.0476(3) Uani 1 1 d . . . . .


_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
C1 O1 1.3588(17) . ?
C1 C6 1.3879(19) . ?
C1 C2 1.4093(17) . ?
C2 C3 1.4022(17) . ?
C2 C7 1.4786(16) . ?
C3 C4 1.3884(17) . ?
C3 H3 0.9400 . ?
C4 C5 1.3977(19) . ?
C4 C18 1.503(2) . ?
C5 C6 1.381(2) . ?
C5 H5 0.9400 . ?
C6 H6 0.9400 . ?
O1 H1 0.8300 . ?
C7 O2 1.2314(16) . ?
C7 C8 1.4920(18) . ?
C8 C9 1.3805(17) . ?
C8 C17 1.4159(17) . ?
C9 C10 1.4117(17) . ?
C9 H9 0.9400 . ?
C10 C11 1.4186(17) . ?
C10 C15 1.4231(17) . ?
C11 C12 1.3706(19) . ?
C11 H11 0.9400 . ?
C12 C13 1.416(2) . ?
C12 C19 1.4756(18) . ?
C13 C14 1.3634(19) . ?
C13 H13 0.9400 . ?
C14 C15 1.4252(18) . ?
C14 H14 0.9400 . ?
C15 C16 1.4155(17) . ?
C16 C17 1.3683(18) . ?
C16 H16 0.9400 . ?
C17 H17 0.9400 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 H18C 0.9700 . ?
C19 O3 1.2113(19) . ?
C19 H19 0.9400 . ?

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
O1 C1 C6 117.56(12) . . ?
O1 C1 C2 122.99(12) . . ?
C6 C1 C2 119.44(12) . . ?
C3 C2 C1 118.83(11) . . ?
C3 C2 C7 121.22(11) . . ?
C1 C2 C7 119.79(11) . . ?
C4 C3 C2 122.04(12) . . ?
C4 C3 H3 119.0 . . ?
C2 C3 H3 119.0 . . ?
C3 C4 C5 117.49(12) . . ?
C3 C4 C18 121.60(12) . . ?
C5 C4 C18 120.90(12) . . ?
C6 C5 C4 121.86(12) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C5 C6 C1 120.30(12) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
C1 O1 H1 109.5 . . ?
O2 C7 C2 120.22(12) . . ?
O2 C7 C8 119.41(11) . . ?
C2 C7 C8 120.36(11) . . ?
C9 C8 C17 119.83(12) . . ?
C9 C8 C7 118.70(11) . . ?
C17 C8 C7 121.25(11) . . ?
C8 C9 C10 120.56(11) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C9 C10 C11 121.63(12) . . ?
C9 C10 C15 119.48(11) . . ?
C11 C10 C15 118.89(12) . . ?
C12 C11 C10 120.65(12) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C13 120.41(12) . . ?
C11 C12 C19 118.72(13) . . ?
C13 C12 C19 120.87(13) . . ?
C14 C13 C12 120.43(13) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C15 120.59(12) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C16 C15 C10 118.68(12) . . ?
C16 C15 C14 122.28(12) . . ?
C10 C15 C14 119.04(11) . . ?
C17 C16 C15 120.94(12) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C16 C17 C8 120.50(11) . . ?
C16 C17 H17 119.8 . . ?
C8 C17 H17 119.8 . . ?
C4 C18 H18A 109.5 . . ?
C4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O3 C19 C12 124.88(15) . . ?
O3 C19 H19 117.6 . . ?
C12 C19 H19 117.6 . . ?

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
O1 C1 C2 C3 178.13(12) . . . . ?
C6 C1 C2 C3 -2.47(18) . . . . ?
O1 C1 C2 C7 2.72(19) . . . . ?
C6 C1 C2 C7 -177.89(12) . . . . ?
C1 C2 C3 C4 1.51(18) . . . . ?
C7 C2 C3 C4 176.86(11) . . . . ?
C2 C3 C4 C5 0.15(18) . . . . ?
C2 C3 C4 C18 178.94(12) . . . . ?
C3 C4 C5 C6 -0.9(2) . . . . ?
C18 C4 C5 C6 -179.68(13) . . . . ?
C4 C5 C6 C1 -0.1(2) . . . . ?
O1 C1 C6 C5 -178.77(13) . . . . ?
C2 C1 C6 C5 1.8(2) . . . . ?
C3 C2 C7 O2 -151.40(12) . . . . ?
C1 C2 C7 O2 23.90(18) . . . . ?
C3 C2 C7 C8 29.91(17) . . . . ?
C1 C2 C7 C8 -154.79(11) . . . . ?
O2 C7 C8 C9 33.64(17) . . . . ?
C2 C7 C8 C9 -147.66(12) . . . . ?
O2 C7 C8 C17 -141.09(13) . . . . ?
C2 C7 C8 C17 37.60(17) . . . . ?
C17 C8 C9 C10 -1.05(18) . . . . ?
C7 C8 C9 C10 -175.86(11) . . . . ?
C8 C9 C10 C11 -179.25(11) . . . . ?
C8 C9 C10 C15 1.30(18) . . . . ?
C9 C10 C11 C12 -179.41(11) . . . . ?
C15 C10 C11 C12 0.04(18) . . . . ?
C10 C11 C12 C13 0.22(19) . . . . ?
C10 C11 C12 C19 -179.90(12) . . . . ?
C11 C12 C13 C14 -0.4(2) . . . . ?
C19 C12 C13 C14 179.71(13) . . . . ?
C12 C13 C14 C15 0.3(2) . . . . ?
C9 C10 C15 C16 -0.55(18) . . . . ?
C11 C10 C15 C16 179.98(11) . . . . ?
C9 C10 C15 C14 179.35(11) . . . . ?
C11 C10 C15 C14 -0.12(18) . . . . ?
C13 C14 C15 C16 179.83(12) . . . . ?
C13 C14 C15 C10 -0.07(19) . . . . ?
C10 C15 C16 C17 -0.43(19) . . . . ?
C14 C15 C16 C17 179.67(12) . . . . ?
C15 C16 C17 C8 0.69(19) . . . . ?
C9 C8 C17 C16 0.06(19) . . . . ?
C7 C8 C17 C16 174.73(12) . . . . ?
C11 C12 C19 O3 -178.06(14) . . . . ?
C13 C12 C19 O3 1.8(2) . . . . ?

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
O1 H1 O2 0.83 1.96 2.6657(15) 142.2 .

_refine_diff_density_max         0.313
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.042


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