# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_exp_2493
_database_code_depnum_ccdc_archive 'CCDC 2078014'
loop_
_audit_author_name
_audit_author_address
'Hua Ting-Bi'
;China Three Gorges University
China
;
_audit_update_record             
;
2021-04-16 deposited with the CCDC.	2022-05-18 downloaded from the CCDC.
;
_audit_creation_date             2020-12-25
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H13 Cl O3'
_chemical_formula_sum            'C18 H13 Cl O3'
_chemical_formula_weight         312.73
_chemical_absolute_configuration s
_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'
Cl Cl 0.3639 0.7018 '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      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_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.98720(10)
_cell_length_b                   12.6464(3)
_cell_length_c                   19.9372(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1509.58(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2779
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.9970
_cell_measurement_theta_min      5.6390
_shelx_estimated_absorpt_T_max   0.801
_shelx_estimated_absorpt_T_min   0.768
_exptl_absorpt_coefficient_mu    2.326
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39556
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
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    1.376
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            4407
_diffrn_reflns_point_group_measured_fraction_full 0.914
_diffrn_reflns_point_group_measured_fraction_max 0.914
_diffrn_reflns_theta_full        66.586
_diffrn_reflns_theta_max         66.586
_diffrn_reflns_theta_min         4.435
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -23.00  22.00   0.50    0.50    --    0.00 -82.00 -90.00   90
  2  ω    -32.00  17.00   0.50    0.50    --    0.00 -82.00-150.00   98
  3  ω    -21.00   5.00   0.50    0.50    --    0.00 -82.00 -30.00   52
  4  ω     17.00 120.00   0.50    0.61    --   95.80 -61.00 150.00  206
  5  ω     61.00 100.00   0.50    0.61    --   95.80 -82.00 150.00   78
  6  ω     81.00 133.00   0.50    0.61    --   95.80  77.00 -90.00  104
  7  ω     62.00 122.00   0.50    0.61    --   95.80   0.00  90.00  120
  8  ω     11.00  55.00   0.50    0.61    --   95.80   0.00  90.00   88
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0513302000
_diffrn_orient_matrix_UB_12      -0.0742801000
_diffrn_orient_matrix_UB_13      0.0593013000
_diffrn_orient_matrix_UB_21      -0.0155525000
_diffrn_orient_matrix_UB_22      -0.0942537000
_diffrn_orient_matrix_UB_23      -0.0487162000
_diffrn_orient_matrix_UB_31      0.2516108000
_diffrn_orient_matrix_UB_32      -0.0209491000
_diffrn_orient_matrix_UB_33      0.0090979000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\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         0.554
_reflns_Friedel_fraction_full    0.793
_reflns_Friedel_fraction_max     0.793
_reflns_number_gt                2207
_reflns_number_total             2431
_reflns_odcompleteness_completeness 99.69
_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 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.125
_refine_diff_density_min         -0.119
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details 
;
 Flack x determined using 703 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.485(14)
_refine_ls_extinction_coef       0.0028(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2431
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0382
_refine_ls_restrained_S_all      1.080
_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)+(0.0558P)²+0.0597P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1058
_refine_ls_wR_factor_ref         0.1081
_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 Ternary CH refined with riding coordinates:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C5(H5), C18(H18), C17(H17), C4(H4), C14(H14), C15(H15), C1(H1),
 C3(H3), C2(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
Cl1 Cl 0.72695(17) 0.01515(7) 0.47300(5) 0.0793(3) Uani 1 1 d . . . . .
O2 O 0.0712(4) 0.3456(2) 0.76656(12) 0.0713(7) Uani 1 1 d . . . . .
O1 O -0.0442(4) 0.2873(2) 0.64454(13) 0.0739(7) Uani 1 1 d . . . . .
O3 O -0.0903(5) 0.5013(2) 0.78699(15) 0.0921(9) Uani 1 1 d . . . . .
C6 C 0.4121(5) 0.6470(2) 0.65765(17) 0.0544(7) Uani 1 1 d . . . . .
C13 C 0.2883(5) 0.1962(2) 0.61567(16) 0.0515(7) Uani 1 1 d . . . . .
C12 C 0.1438(5) 0.2623(2) 0.66002(17) 0.0548(8) Uani 1 1 d . . . . .
C8 C 0.2482(5) 0.4914(3) 0.72035(15) 0.0548(7) Uani 1 1 d . . . . .
C11 C 0.2458(5) 0.3048(3) 0.72441(16) 0.0596(8) Uani 1 1 d . . . . .
H11 H 0.3291 0.2491 0.7477 0.072 Uiso 1 1 calc R U . . .
C7 C 0.2521(5) 0.5915(3) 0.70032(16) 0.0582(8) Uani 1 1 d . . . . .
H7 H 0.1345 0.6327 0.7159 0.070 Uiso 1 1 calc R U . . .
C16 C 0.5540(5) 0.0826(2) 0.52852(17) 0.0573(8) Uani 1 1 d . . . . .
C5 C 0.6186(5) 0.6067(2) 0.63778(19) 0.0617(8) Uani 1 1 d . . . . .
H5 H 0.6634 0.5405 0.6530 0.074 Uiso 1 1 calc R U . . .
C18 C 0.4964(6) 0.1607(3) 0.63567(17) 0.0607(8) Uani 1 1 d . . . . .
H18 H 0.5473 0.1761 0.6787 0.073 Uiso 1 1 calc R U . . .
C10 C 0.4000(5) 0.3995(2) 0.70815(17) 0.0561(8) Uani 1 1 d . . . . .
H10A H 0.5286 0.4013 0.7377 0.067 Uiso 1 1 calc R U . . .
H10B H 0.4506 0.3974 0.6620 0.067 Uiso 1 1 calc R U . . .
C9 C 0.0575(6) 0.4532(3) 0.76096(17) 0.0657(9) Uani 1 1 d . . . . .
C17 C 0.6300(6) 0.1027(3) 0.59271(18) 0.0616(8) Uani 1 1 d . . . . .
H17 H 0.7683 0.0776 0.6068 0.074 Uiso 1 1 calc R U . . .
C4 C 0.7564(6) 0.6631(3) 0.5962(2) 0.0740(10) Uani 1 1 d . . . . .
H4 H 0.8926 0.6344 0.5830 0.089 Uiso 1 1 calc R U . . .
C14 C 0.2146(6) 0.1718(3) 0.55134(16) 0.0600(8) Uani 1 1 d . . . . .
H14 H 0.0744 0.1946 0.5375 0.072 Uiso 1 1 calc R U . . .
C15 C 0.3455(6) 0.1145(3) 0.50796(18) 0.0638(9) Uani 1 1 d . . . . .
H15 H 0.2938 0.0975 0.4653 0.077 Uiso 1 1 calc R U . . .
C1 C 0.3533(6) 0.7481(3) 0.6345(2) 0.0708(10) Uani 1 1 d . . . . .
H1 H 0.2177 0.7776 0.6474 0.085 Uiso 1 1 calc R U . . .
C3 C 0.6951(8) 0.7619(3) 0.5738(2) 0.0839(12) Uani 1 1 d . . . . .
H3 H 0.7897 0.7999 0.5458 0.101 Uiso 1 1 calc R U . . .
C2 C 0.4936(8) 0.8040(3) 0.5930(2) 0.0852(12) Uani 1 1 d . . . . .
H2 H 0.4519 0.8707 0.5779 0.102 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
Cl1 C16 1.739(3) . ?
O2 C11 1.437(4) . ?
O2 C9 1.367(4) . ?
O1 C12 1.209(4) . ?
O3 C9 1.193(4) . ?
C6 C7 1.461(4) . ?
C6 C5 1.395(4) . ?
C6 C1 1.404(5) . ?
C13 C12 1.493(5) . ?
C13 C18 1.383(4) . ?
C13 C14 1.391(4) . ?
C12 C11 1.520(4) . ?
C8 C7 1.327(5) . ?
C8 C10 1.496(4) . ?
C8 C9 1.481(5) . ?
C11 H11 0.9800 . ?
C11 C10 1.547(4) . ?
C7 H7 0.9300 . ?
C16 C17 1.382(5) . ?
C16 C15 1.375(5) . ?
C5 H5 0.9300 . ?
C5 C4 1.370(5) . ?
C18 H18 0.9300 . ?
C18 C17 1.383(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C17 H17 0.9300 . ?
C4 H4 0.9300 . ?
C4 C3 1.376(6) . ?
C14 H14 0.9300 . ?
C14 C15 1.374(5) . ?
C15 H15 0.9300 . ?
C1 H1 0.9300 . ?
C1 C2 1.374(5) . ?
C3 H3 0.9300 . ?
C3 C2 1.373(6) . ?
C2 H2 0.9300 . ?

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
C9 O2 C11 110.7(3) . . ?
C5 C6 C7 124.8(3) . . ?
C5 C6 C1 117.5(3) . . ?
C1 C6 C7 117.7(3) . . ?
C18 C13 C12 122.2(3) . . ?
C18 C13 C14 118.6(3) . . ?
C14 C13 C12 119.1(3) . . ?
O1 C12 C13 122.3(3) . . ?
O1 C12 C11 119.8(3) . . ?
C13 C12 C11 117.7(3) . . ?
C7 C8 C10 133.0(3) . . ?
C7 C8 C9 119.3(3) . . ?
C9 C8 C10 107.7(3) . . ?
O2 C11 C12 109.2(3) . . ?
O2 C11 H11 110.6 . . ?
O2 C11 C10 106.2(3) . . ?
C12 C11 H11 110.6 . . ?
C12 C11 C10 109.6(3) . . ?
C10 C11 H11 110.6 . . ?
C6 C7 H7 114.9 . . ?
C8 C7 C6 130.2(3) . . ?
C8 C7 H7 114.9 . . ?
C17 C16 Cl1 118.9(3) . . ?
C15 C16 Cl1 119.7(3) . . ?
C15 C16 C17 121.4(3) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 C6 121.0(3) . . ?
C4 C5 H5 119.5 . . ?
C13 C18 H18 119.5 . . ?
C17 C18 C13 121.0(3) . . ?
C17 C18 H18 119.5 . . ?
C8 C10 C11 101.8(2) . . ?
C8 C10 H10A 111.4 . . ?
C8 C10 H10B 111.4 . . ?
C11 C10 H10A 111.4 . . ?
C11 C10 H10B 111.4 . . ?
H10A C10 H10B 109.3 . . ?
O2 C9 C8 108.9(3) . . ?
O3 C9 O2 121.1(3) . . ?
O3 C9 C8 130.0(4) . . ?
C16 C17 C18 118.7(3) . . ?
C16 C17 H17 120.6 . . ?
C18 C17 H17 120.6 . . ?
C5 C4 H4 119.7 . . ?
C5 C4 C3 120.5(4) . . ?
C3 C4 H4 119.7 . . ?
C13 C14 H14 119.4 . . ?
C15 C14 C13 121.1(3) . . ?
C15 C14 H14 119.4 . . ?
C16 C15 H15 120.5 . . ?
C14 C15 C16 119.0(3) . . ?
C14 C15 H15 120.5 . . ?
C6 C1 H1 119.6 . . ?
C2 C1 C6 120.9(4) . . ?
C2 C1 H1 119.6 . . ?
C4 C3 H3 120.1 . . ?
C2 C3 C4 119.7(4) . . ?
C2 C3 H3 120.1 . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.3(4) . . ?
C3 C2 H2 119.8 . . ?

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
Cl1 C16 C17 C18 176.9(3) . . . . ?
Cl1 C16 C15 C14 -177.1(2) . . . . ?
O2 C11 C10 C8 -21.7(3) . . . . ?
O1 C12 C11 O2 16.6(4) . . . . ?
O1 C12 C11 C10 -99.4(3) . . . . ?
C6 C5 C4 C3 0.9(6) . . . . ?
C6 C1 C2 C3 -0.4(7) . . . . ?
C13 C12 C11 O2 -167.4(2) . . . . ?
C13 C12 C11 C10 76.6(3) . . . . ?
C13 C18 C17 C16 1.5(5) . . . . ?
C13 C14 C15 C16 -1.1(5) . . . . ?
C12 C13 C18 C17 -177.7(3) . . . . ?
C12 C13 C14 C15 177.6(3) . . . . ?
C12 C11 C10 C8 96.2(3) . . . . ?
C11 O2 C9 O3 172.8(3) . . . . ?
C11 O2 C9 C8 -7.7(4) . . . . ?
C7 C6 C5 C4 178.3(3) . . . . ?
C7 C6 C1 C2 -178.6(4) . . . . ?
C7 C8 C10 C11 -159.8(4) . . . . ?
C7 C8 C9 O2 170.5(3) . . . . ?
C7 C8 C9 O3 -10.1(6) . . . . ?
C5 C6 C7 C8 -11.1(6) . . . . ?
C5 C6 C1 C2 0.9(5) . . . . ?
C5 C4 C3 C2 -0.3(7) . . . . ?
C18 C13 C12 O1 -174.7(3) . . . . ?
C18 C13 C12 C11 9.4(4) . . . . ?
C18 C13 C14 C15 -0.6(4) . . . . ?
C10 C8 C7 C6 0.4(6) . . . . ?
C10 C8 C9 O2 -7.1(4) . . . . ?
C10 C8 C9 O3 172.3(4) . . . . ?
C9 O2 C11 C12 -99.3(3) . . . . ?
C9 O2 C11 C10 18.9(4) . . . . ?
C9 C8 C7 C6 -176.5(3) . . . . ?
C9 C8 C10 C11 17.4(3) . . . . ?
C17 C16 C15 C14 3.0(5) . . . . ?
C4 C3 C2 C1 0.1(7) . . . . ?
C14 C13 C12 O1 7.2(4) . . . . ?
C14 C13 C12 C11 -168.7(3) . . . . ?
C14 C13 C18 C17 0.4(5) . . . . ?
C15 C16 C17 C18 -3.2(5) . . . . ?
C1 C6 C7 C8 168.4(4) . . . . ?
C1 C6 C5 C4 -1.2(5) . . . . ?

_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 2.146
_oxdiff_exptl_absorpt_empirical_full_min 0.405
####################################################################### 
# 
# 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_5071
_database_code_depnum_ccdc_archive 'CCDC 2169376'
loop_
_audit_author_name
_audit_author_address
'Ma Yu-Hong'
;Three Gorges University
China
;
_audit_update_record             
;
2022-04-29 deposited with the CCDC.	2022-05-18 downloaded from the CCDC.
;
_audit_creation_date             2022-04-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5227)
;
_shelxl_version_number           2014-1
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C18 H16 O3'
_chemical_formula_sum            'C18 H16 O3'
_chemical_formula_weight         280.31
_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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.5652(3)
_cell_length_b                   17.1995(4)
_cell_length_c                   9.7794(3)
_cell_angle_alpha                90
_cell_angle_beta                 116.893(4)
_cell_angle_gamma                90
_cell_volume                     1434.89(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4215
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      74.0120
_cell_measurement_theta_min      5.0180
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.708
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.23687
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6807
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.944
_diffrn_reflns_theta_min         5.143
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -32.00  15.00   0.50    0.50    --    0.00 -82.00 -90.00   94
  2  ω    -17.00  32.00   0.50    0.50    --    0.00 -82.00 120.00   98
  3  ω    -31.00  17.00   0.50    0.50    --    0.00 -82.00  30.00   96
  4  ω    107.00 133.00   0.50    0.50    --   95.80  82.00  30.00   52
  5  ω     93.00 153.00   0.50    0.50    --   95.80  15.00-120.00  120
  6  ω     22.00  77.00   0.50    0.50    --   95.80 -45.00 -60.00  110
  7  ω    116.00 172.00   0.50    0.50    --   95.80  15.00-180.00  112
  8  ω     79.00 161.00   0.50    0.50    --   95.80  77.00  60.00  164
  9  ω     83.00 112.00   0.50    0.50    --   95.80 -45.00 -60.00   58
 10  ω    153.00 178.00   0.50    0.50    --   95.80  82.00  30.00   50
 11  ω     15.00 120.00   0.50    0.50    --   95.80 -61.00 -60.00  210
 12  ω     17.00 108.00   0.50    0.50    --   95.80 -61.00 120.00  182
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0769238000
_diffrn_orient_matrix_UB_12      0.0738225000
_diffrn_orient_matrix_UB_13      0.0929566000
_diffrn_orient_matrix_UB_21      -0.1420051000
_diffrn_orient_matrix_UB_22      0.0118855000
_diffrn_orient_matrix_UB_23      0.0322655000
_diffrn_orient_matrix_UB_31      0.0807826000
_diffrn_orient_matrix_UB_32      -0.0492914000
_diffrn_orient_matrix_UB_33      0.1466951000
_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                2390
_reflns_number_total             2703
_reflns_odcompleteness_completeness 99.85
_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 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 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         0.181
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2703
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0565
_refine_ls_restrained_S_all      1.062
_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)+(0.1010P)²+0.1500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1514
_refine_ls_wR_factor_ref         0.1554
_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:
 C007(H007), C00B(H00C)
2.b Secondary CH2 refined with riding coordinates:
 C00A(H00A,H00B)
2.c Aromatic/amide H refined with riding coordinates:
 C009(H009), C00C(H00D), C00D(H00E), C00E(H00F), C00F(H00G), C00G(H00H),
 C00H(H00I), C00I(H00J), C00J(H00K), C00K(H00L), C00L(H00M)
2.d Idealised tetrahedral OH refined as rotating group:
 O002(H002)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
O001 O 0.59407(12) 0.66645(7) 0.68071(12) 0.0563(3) Uani 1 1 d . . . . .
O002 O 0.32791(13) 0.75573(7) 0.52005(14) 0.0584(3) Uani 1 1 d . . . . .
H002 H 0.2627 0.7879 0.4670 0.088 Uiso 1 1 calc GR . . . .
O003 O 0.60100(13) 0.61984(8) 0.89430(12) 0.0632(4) Uani 1 1 d . . . . .
C004 C 0.22708(16) 0.45867(9) 0.61495(16) 0.0448(3) Uani 1 1 d . . . . .
C005 C 0.41125(15) 0.57088(8) 0.64685(15) 0.0438(3) Uani 1 1 d . . . . .
C006 C 0.54065(17) 0.61942(9) 0.75589(17) 0.0486(4) Uani 1 1 d . . . . .
C007 C 0.43003(16) 0.73907(9) 0.45457(16) 0.0464(4) Uani 1 1 d . . . . .
H007 H 0.3677 0.7355 0.3431 0.056 Uiso 1 1 calc R . . . .
C008 C 0.55512(17) 0.80078(9) 0.48997(16) 0.0476(4) Uani 1 1 d . . . . .
C009 C 0.34899(17) 0.51574(9) 0.69851(16) 0.0461(4) Uani 1 1 d . . . . .
H009 H 0.3898 0.5133 0.8046 0.055 Uiso 1 1 calc R . . . .
C00A C 0.37954(18) 0.59555(9) 0.48866(16) 0.0485(4) Uani 1 1 d . . . . .
H00A H 0.2736 0.6153 0.4323 0.058 Uiso 1 1 calc R . . . .
H00B H 0.3939 0.5525 0.4322 0.058 Uiso 1 1 calc R . . . .
C00B C 0.50032(17) 0.65980(9) 0.51540(17) 0.0481(4) Uani 1 1 d . . . . .
H00C H 0.5680 0.6444 0.4691 0.058 Uiso 1 1 calc R . . . .
C00C C 0.14451(18) 0.45538(9) 0.45477(17) 0.0501(4) Uani 1 1 d . . . . .
H00D H 0.1670 0.4909 0.3958 0.060 Uiso 1 1 calc R . . . .
C00D C 0.18988(19) 0.40411(10) 0.69915(18) 0.0550(4) Uani 1 1 d . . . . .
H00E H 0.2440 0.4046 0.8056 0.066 Uiso 1 1 calc R . . . .
C00E C 0.03012(19) 0.39992(10) 0.38379(19) 0.0571(4) Uani 1 1 d . . . . .
H00F H -0.0231 0.3981 0.2773 0.069 Uiso 1 1 calc R . . . .
C00F C -0.0062(2) 0.34728(10) 0.4686(2) 0.0597(4) Uani 1 1 d . . . . .
H00G H -0.0843 0.3105 0.4196 0.072 Uiso 1 1 calc R . . . .
C00G C 0.0733(2) 0.34912(11) 0.6261(2) 0.0630(5) Uani 1 1 d . . . . .
H00H H 0.0489 0.3135 0.6837 0.076 Uiso 1 1 calc R . . . .
C00H C 0.5432(2) 0.87243(11) 0.5482(2) 0.0637(5) Uani 1 1 d . . . . .
H00I H 0.4589 0.8827 0.5685 0.076 Uiso 1 1 calc R . . . .
C00I C 0.6823(2) 0.78755(12) 0.4615(2) 0.0680(5) Uani 1 1 d . . . . .
H00J H 0.6920 0.7400 0.4213 0.082 Uiso 1 1 calc R . . . .
C00J C 0.7954(2) 0.84433(15) 0.4922(3) 0.0867(7) Uani 1 1 d . . . . .
H00K H 0.8812 0.8343 0.4742 0.104 Uiso 1 1 calc R . . . .
C00K C 0.7813(3) 0.91476(16) 0.5485(2) 0.0846(7) Uani 1 1 d . . . . .
H00L H 0.8567 0.9530 0.5679 0.101 Uiso 1 1 calc R . . . .
C00L C 0.6564(3) 0.92909(13) 0.5764(2) 0.0796(6) Uani 1 1 d . . . . .
H00M H 0.6469 0.9772 0.6147 0.096 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
O001 C006 1.3401(19) . ?
O001 C00B 1.4558(18) . ?
O002 H002 0.8200 . ?
O002 C007 1.4185(17) . ?
O003 C006 1.2078(18) . ?
C004 C009 1.459(2) . ?
C004 C00C 1.401(2) . ?
C004 C00D 1.397(2) . ?
C005 C006 1.474(2) . ?
C005 C009 1.335(2) . ?
C005 C00A 1.497(2) . ?
C007 H007 0.9800 . ?
C007 C008 1.518(2) . ?
C007 C00B 1.518(2) . ?
C008 C00H 1.384(2) . ?
C008 C00I 1.384(2) . ?
C009 H009 0.9300 . ?
C00A H00A 0.9700 . ?
C00A H00B 0.9700 . ?
C00A C00B 1.533(2) . ?
C00B H00C 0.9800 . ?
C00C H00D 0.9300 . ?
C00C C00E 1.379(2) . ?
C00D H00E 0.9300 . ?
C00D C00G 1.389(2) . ?
C00E H00F 0.9300 . ?
C00E C00F 1.374(2) . ?
C00F H00G 0.9300 . ?
C00F C00G 1.375(3) . ?
C00G H00H 0.9300 . ?
C00H H00I 0.9300 . ?
C00H C00L 1.388(3) . ?
C00I H00J 0.9300 . ?
C00I C00J 1.385(3) . ?
C00J H00K 0.9300 . ?
C00J C00K 1.362(4) . ?
C00K H00L 0.9300 . ?
C00K C00L 1.363(3) . ?
C00L H00M 0.9300 . ?

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
C006 O001 C00B 111.44(11) . . ?
C007 O002 H002 109.5 . . ?
C00C C004 C009 123.85(13) . . ?
C00D C004 C009 118.30(13) . . ?
C00D C004 C00C 117.85(14) . . ?
C006 C005 C00A 107.36(12) . . ?
C009 C005 C006 120.08(13) . . ?
C009 C005 C00A 132.54(13) . . ?
O001 C006 C005 110.42(12) . . ?
O003 C006 O001 120.25(14) . . ?
O003 C006 C005 129.31(15) . . ?
O002 C007 H007 108.6 . . ?
O002 C007 C008 112.86(13) . . ?
O002 C007 C00B 106.15(11) . . ?
C008 C007 H007 108.6 . . ?
C00B C007 H007 108.6 . . ?
C00B C007 C008 112.03(12) . . ?
C00H C008 C007 120.91(14) . . ?
C00H C008 C00I 118.20(16) . . ?
C00I C008 C007 120.87(15) . . ?
C004 C009 H009 114.9 . . ?
C005 C009 C004 130.27(13) . . ?
C005 C009 H009 114.9 . . ?
C005 C00A H00A 110.9 . . ?
C005 C00A H00B 110.9 . . ?
C005 C00A C00B 104.08(12) . . ?
H00A C00A H00B 109.0 . . ?
C00B C00A H00A 110.9 . . ?
C00B C00A H00B 110.9 . . ?
O001 C00B C007 107.81(12) . . ?
O001 C00B C00A 106.51(11) . . ?
O001 C00B H00C 109.3 . . ?
C007 C00B C00A 114.49(12) . . ?
C007 C00B H00C 109.3 . . ?
C00A C00B H00C 109.3 . . ?
C004 C00C H00D 119.7 . . ?
C00E C00C C004 120.56(15) . . ?
C00E C00C H00D 119.7 . . ?
C004 C00D H00E 119.5 . . ?
C00G C00D C004 120.93(15) . . ?
C00G C00D H00E 119.5 . . ?
C00C C00E H00F 119.6 . . ?
C00F C00E C00C 120.76(15) . . ?
C00F C00E H00F 119.6 . . ?
C00E C00F H00G 120.1 . . ?
C00E C00F C00G 119.88(16) . . ?
C00G C00F H00G 120.1 . . ?
C00D C00G H00H 120.0 . . ?
C00F C00G C00D 120.01(16) . . ?
C00F C00G H00H 120.0 . . ?
C008 C00H H00I 119.8 . . ?
C008 C00H C00L 120.36(19) . . ?
C00L C00H H00I 119.8 . . ?
C008 C00I H00J 119.6 . . ?
C008 C00I C00J 120.8(2) . . ?
C00J C00I H00J 119.6 . . ?
C00I C00J H00K 119.9 . . ?
C00K C00J C00I 120.3(2) . . ?
C00K C00J H00K 119.9 . . ?
C00J C00K H00L 120.1 . . ?
C00J C00K C00L 119.85(19) . . ?
C00L C00K H00L 120.1 . . ?
C00H C00L H00M 119.7 . . ?
C00K C00L C00H 120.5(2) . . ?
C00K C00L H00M 119.7 . . ?

_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 2.658
_oxdiff_exptl_absorpt_empirical_full_min 0.493
