# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2024

####################################################################### 
# 
# 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_8094
_database_code_depnum_ccdc_archive 'CCDC 2183633'
loop_
_audit_author_name
_audit_author_address
'Wang Mingan'
;China Agricultural University
China
;
_audit_update_record             
;
2022-07-04 deposited with the CCDC.	2023-12-01 downloaded from the CCDC.
;
_audit_creation_date             2022-07-01
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C19 H14 O2'
_chemical_formula_sum            'C19 H14 O2'
_chemical_formula_weight         274.30
_chemical_absolute_configuration unk
_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 0.0033 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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'

_cell_length_a                   4.2162(5)
_cell_length_b                   14.4562(15)
_cell_length_c                   21.1593(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1289.7(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    770
_cell_measurement_temperature    124.3(3)
_cell_measurement_theta_max      24.2280
_cell_measurement_theta_min      4.3250
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82773
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0524
_diffrn_reflns_av_unetI/netI     0.1038
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            5130
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.21
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      124.3(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9943
_diffrn_measured_fraction_theta_max 0.8191
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   36.00   88.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       16.0852  178.0000 -120.0000 52

#__ type_ start__ end____ width___ exp.time_
  2 omega  -45.00   18.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       16.0852  -37.0000   30.0000 63

#__ type_ start__ end____ width___ exp.time_
  3 omega  -51.00  -21.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       16.0852  -77.0000  -30.0000 30

#__ type_ start__ end____ width___ exp.time_
  4 omega   54.00   81.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       15.9289  178.0000   60.0000 27

#__ type_ start__ end____ width___ exp.time_
  5 omega   40.00   71.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       15.9289   57.0000 -120.0000 31
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0658549000
_diffrn_orient_matrix_UB_12      0.0447416000
_diffrn_orient_matrix_UB_13      0.0038794000
_diffrn_orient_matrix_UB_21      -0.0718314000
_diffrn_orient_matrix_UB_22      -0.0033466000
_diffrn_orient_matrix_UB_23      -0.0301844000
_diffrn_orient_matrix_UB_31      -0.1369864000
_diffrn_orient_matrix_UB_32      -0.0197355000
_diffrn_orient_matrix_UB_33      0.0139852000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1573
_reflns_number_total             2482
_reflns_odcompleteness_completeness 99.43
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.07
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -3(3)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2482
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1026
_refine_ls_R_factor_gt           0.0602
_refine_ls_restrained_S_all      1.013
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0411P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1067
_refine_ls_wR_factor_ref         0.1339
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
O2 O -0.6705(6) -0.38011(16) -0.10537(9) 0.0309(6) Uani 1 1 d . . .
C10 C -1.0087(8) -0.3816(2) -0.29194(13) 0.0220(8) Uani 1 1 d . . .
C9 C -0.8123(8) -0.4543(2) -0.26891(13) 0.0217(8) Uani 1 1 d . . .
O1 O -0.8130(6) -0.61145(17) -0.40293(9) 0.0353(7) Uani 1 1 d . . .
C11 C -1.1299(8) -0.3876(2) -0.35721(13) 0.0230(8) Uani 1 1 d . . .
C4 C -0.6959(8) -0.4515(2) -0.20512(13) 0.0229(8) Uani 1 1 d . . .
C1 C -1.0810(9) -0.3100(2) -0.25160(12) 0.0263(8) Uani 1 1 d . . .
H1 H -1.2060 -0.2617 -0.2667 0.032 Uiso 1 1 calc R . .
C6 C -0.4124(9) -0.5951(2) -0.22180(14) 0.0284(9) Uani 1 1 d . . .
H6 H -0.2758 -0.6407 -0.2069 0.034 Uiso 1 1 calc R . .
C12 C -1.0622(9) -0.4653(2) -0.39491(14) 0.0232(8) Uani 1 1 d . . .
C16 C -1.4399(9) -0.3251(3) -0.44376(13) 0.0292(9) Uani 1 1 d . . .
H16 H -1.5648 -0.2777 -0.4600 0.035 Uiso 1 1 calc R . .
C13 C -0.8617(9) -0.5415(2) -0.37121(14) 0.0275(9) Uani 1 1 d . . .
C15 C -1.3793(8) -0.4025(2) -0.48091(13) 0.0258(8) Uani 1 1 d . . .
C3 C -0.7851(8) -0.3754(2) -0.16563(13) 0.0235(8) Uani 1 1 d . . .
C17 C -1.3194(8) -0.3169(3) -0.38344(13) 0.0278(9) Uani 1 1 d . . .
H17 H -1.3635 -0.2642 -0.3598 0.033 Uiso 1 1 calc R . .
C8 C -0.7302(8) -0.5318(2) -0.30639(13) 0.0232(8) Uani 1 1 d . . .
C14 C -1.1910(8) -0.4723(2) -0.45603(13) 0.0264(8) Uani 1 1 d . . .
H14 H -1.1493 -0.5246 -0.4802 0.032 Uiso 1 1 calc R . .
C2 C -0.9749(8) -0.3063(3) -0.18871(13) 0.0262(9) Uani 1 1 d . . .
H2 H -1.0334 -0.2572 -0.1628 0.031 Uiso 1 1 calc R . .
C18 C -1.5174(9) -0.4105(3) -0.54699(13) 0.0357(10) Uani 1 1 d . . .
H18A H -1.4024 -0.3708 -0.5752 0.054 Uiso 1 1 calc R . .
H18B H -1.7365 -0.3925 -0.5463 0.054 Uiso 1 1 calc R . .
H18C H -1.5006 -0.4734 -0.5613 0.054 Uiso 1 1 calc R . .
C7 C -0.5315(9) -0.5998(3) -0.28366(13) 0.0279(9) Uani 1 1 d . . .
H7 H -0.4757 -0.6492 -0.3095 0.034 Uiso 1 1 calc R . .
C5 C -0.4989(9) -0.5229(3) -0.18338(14) 0.0284(9) Uani 1 1 d . . .
H5 H -0.4250 -0.5212 -0.1420 0.034 Uiso 1 1 calc R . .
C19 C -0.7725(11) -0.3089(3) -0.06186(13) 0.0408(11) Uani 1 1 d . . .
H19A H -0.6974 -0.3232 -0.0202 0.061 Uiso 1 1 calc R . .
H19B H -1.0000 -0.3059 -0.0616 0.061 Uiso 1 1 calc R . .
H19C H -0.6879 -0.2503 -0.0750 0.061 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
O2 C3 1.365(3) . ?
O2 C19 1.446(4) . ?
C10 C9 1.425(4) . ?
C10 C11 1.475(4) . ?
C10 C1 1.376(4) . ?
C9 C4 1.437(4) . ?
C9 C8 1.416(4) . ?
O1 C13 1.231(4) . ?
C11 C12 1.407(4) . ?
C11 C17 1.411(4) . ?
C4 C3 1.432(4) . ?
C4 C5 1.402(5) . ?
C1 H1 0.9300 . ?
C1 C2 1.405(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.404(4) . ?
C6 C5 1.373(4) . ?
C12 C13 1.476(5) . ?
C12 C14 1.406(4) . ?
C16 H16 0.9300 . ?
C16 C15 1.391(4) . ?
C16 C17 1.379(4) . ?
C13 C8 1.486(4) . ?
C15 C14 1.387(4) . ?
C15 C18 1.519(4) . ?
C3 C2 1.370(4) . ?
C17 H17 0.9300 . ?
C8 C7 1.377(4) . ?
C14 H14 0.9300 . ?
C2 H2 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C7 H7 0.9300 . ?
C5 H5 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 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
C3 O2 C19 117.0(3) . . ?
C9 C10 C11 118.6(3) . . ?
C1 C10 C9 118.2(3) . . ?
C1 C10 C11 123.2(3) . . ?
C10 C9 C4 119.9(3) . . ?
C8 C9 C10 122.3(3) . . ?
C8 C9 C4 117.7(3) . . ?
C12 C11 C10 120.5(3) . . ?
C12 C11 C17 118.0(3) . . ?
C17 C11 C10 121.5(3) . . ?
C3 C4 C9 118.7(3) . . ?
C5 C4 C9 119.3(3) . . ?
C5 C4 C3 122.0(3) . . ?
C10 C1 H1 118.5 . . ?
C10 C1 C2 123.0(3) . . ?
C2 C1 H1 118.5 . . ?
C7 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C5 C6 C7 119.6(3) . . ?
C11 C12 C13 121.3(3) . . ?
C14 C12 C11 120.0(3) . . ?
C14 C12 C13 118.7(3) . . ?
C15 C16 H16 119.2 . . ?
C17 C16 H16 119.2 . . ?
C17 C16 C15 121.7(3) . . ?
O1 C13 C12 121.5(3) . . ?
O1 C13 C8 121.2(3) . . ?
C12 C13 C8 117.2(3) . . ?
C16 C15 C18 120.7(3) . . ?
C14 C15 C16 118.4(3) . . ?
C14 C15 C18 120.9(3) . . ?
O2 C3 C4 114.4(3) . . ?
O2 C3 C2 125.2(3) . . ?
C2 C3 C4 120.4(3) . . ?
C11 C17 H17 119.7 . . ?
C16 C17 C11 120.7(3) . . ?
C16 C17 H17 119.7 . . ?
C9 C8 C13 120.0(3) . . ?
C7 C8 C9 121.2(3) . . ?
C7 C8 C13 118.8(3) . . ?
C12 C14 H14 119.4 . . ?
C15 C14 C12 121.2(3) . . ?
C15 C14 H14 119.4 . . ?
C1 C2 H2 120.1 . . ?
C3 C2 C1 119.8(3) . . ?
C3 C2 H2 120.1 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C6 C7 H7 119.7 . . ?
C8 C7 C6 120.6(3) . . ?
C8 C7 H7 119.7 . . ?
C4 C5 H5 119.2 . . ?
C6 C5 C4 121.5(3) . . ?
C6 C5 H5 119.2 . . ?
O2 C19 H19A 109.5 . . ?
O2 C19 H19B 109.5 . . ?
O2 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
O2 C3 C2 C1 -179.2(3) . . . . ?
C10 C9 C4 C3 0.9(4) . . . . ?
C10 C9 C4 C5 -179.0(3) . . . . ?
C10 C9 C8 C13 -2.8(5) . . . . ?
C10 C9 C8 C7 177.9(3) . . . . ?
C10 C11 C12 C13 -1.8(5) . . . . ?
C10 C11 C12 C14 177.1(3) . . . . ?
C10 C11 C17 C16 -177.7(3) . . . . ?
C10 C1 C2 C3 1.4(5) . . . . ?
C9 C10 C11 C12 2.4(4) . . . . ?
C9 C10 C11 C17 -178.5(3) . . . . ?
C9 C10 C1 C2 -1.2(5) . . . . ?
C9 C4 C3 O2 178.2(3) . . . . ?
C9 C4 C3 C2 -0.7(5) . . . . ?
C9 C4 C5 C6 0.5(5) . . . . ?
C9 C8 C7 C6 1.9(5) . . . . ?
O1 C13 C8 C9 -174.5(3) . . . . ?
O1 C13 C8 C7 4.8(5) . . . . ?
C11 C10 C9 C4 -178.7(3) . . . . ?
C11 C10 C9 C8 0.0(4) . . . . ?
C11 C10 C1 C2 177.5(3) . . . . ?
C11 C12 C13 O1 176.8(3) . . . . ?
C11 C12 C13 C8 -1.0(5) . . . . ?
C11 C12 C14 C15 1.6(5) . . . . ?
C4 C9 C8 C13 175.9(3) . . . . ?
C4 C9 C8 C7 -3.4(5) . . . . ?
C4 C3 C2 C1 -0.4(5) . . . . ?
C1 C10 C9 C4 0.0(4) . . . . ?
C1 C10 C9 C8 178.7(3) . . . . ?
C1 C10 C11 C12 -176.3(3) . . . . ?
C1 C10 C11 C17 2.9(5) . . . . ?
C12 C11 C17 C16 1.4(5) . . . . ?
C12 C13 C8 C9 3.3(4) . . . . ?
C12 C13 C8 C7 -177.4(3) . . . . ?
C16 C15 C14 C12 -0.3(5) . . . . ?
C13 C12 C14 C15 -179.5(3) . . . . ?
C13 C8 C7 C6 -177.5(3) . . . . ?
C15 C16 C17 C11 -0.2(5) . . . . ?
C3 C4 C5 C6 -179.4(3) . . . . ?
C17 C11 C12 C13 179.0(3) . . . . ?
C17 C11 C12 C14 -2.1(5) . . . . ?
C17 C16 C15 C14 -0.3(5) . . . . ?
C17 C16 C15 C18 179.4(3) . . . . ?
C8 C9 C4 C3 -177.8(3) . . . . ?
C8 C9 C4 C5 2.2(4) . . . . ?
C14 C12 C13 O1 -2.1(5) . . . . ?
C14 C12 C13 C8 -179.9(3) . . . . ?
C18 C15 C14 C12 180.0(3) . . . . ?
C7 C6 C5 C4 -2.1(5) . . . . ?
C5 C4 C3 O2 -1.9(5) . . . . ?
C5 C4 C3 C2 179.2(3) . . . . ?
C5 C6 C7 C8 1.0(5) . . . . ?
C19 O2 C3 C4 -175.4(3) . . . . ?
C19 O2 C3 C2 3.5(5) . . . . ?
