# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_10119
_database_code_depnum_ccdc_archive 'CCDC 2495483'
loop_
_audit_author_name
_audit_author_address
'Wang Mingan'
;China Agricultural University
China
;
_audit_update_record             
;
2025-10-15 deposited with the CCDC.	2025-11-24 downloaded from the CCDC.
;
_audit_creation_date             2025-09-12
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C14 H11 F O2'
_chemical_formula_sum            'C14 H11 F O2'
_chemical_formula_weight         230.23
_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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_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'
5 '-x, -y, -z'
6 'x-1/2, y, -z-1/2'
7 '-x-1/2, y-1/2, z'
8 'x, -y-1/2, z-1/2'

_cell_length_a                   13.7379(4)
_cell_length_b                   10.0334(3)
_cell_length_c                   16.1142(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2221.14(12)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2014
_cell_measurement_temperature    117.30(14)
_cell_measurement_theta_max      66.4230
_cell_measurement_theta_min      5.4740
_exptl_absorpt_coefficient_mu    0.854
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85026
_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            colorless
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.20
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            4512
_diffrn_reflns_theta_full        66.46
_diffrn_reflns_theta_max         66.46
_diffrn_reflns_theta_min         5.49
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      117.30(14)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9980
_diffrn_measured_fraction_theta_max 0.9743
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -29.00   -3.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -37.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega   -1.00   55.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -37.0000  -90.0000 56

#__ type_ start__ end____ width___ exp.time_
  3 omega  100.00  125.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       98.5477  -77.0000 -120.0000 25

#__ type_ start__ end____ width___ exp.time_
  4 omega   55.00  107.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919 -178.0000  -90.0000 52

#__ type_ start__ end____ width___ exp.time_
  5 omega   32.00   57.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       98.5477  -77.0000 -120.0000 25

#__ type_ start__ end____ width___ exp.time_
  6 omega   45.00   80.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       98.5477  -30.0000   60.0000 35

#__ type_ start__ end____ width___ exp.time_
  7 omega   75.00  166.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       98.5477   15.0000  150.0000 91

#__ type_ start__ end____ width___ exp.time_
  8 omega   74.00  165.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       98.5477   77.0000    0.0000 91

#__ type_ start__ end____ width___ exp.time_
  9 omega   60.00   98.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  178.0000   90.0000 38

#__ type_ start__ end____ width___ exp.time_
 10 omega   48.00   88.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   57.0000 -120.0000 40
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0682288000
_diffrn_orient_matrix_UB_12      0.0332486000
_diffrn_orient_matrix_UB_13      0.0729017000
_diffrn_orient_matrix_UB_21      -0.0612144000
_diffrn_orient_matrix_UB_22      0.1246733000
_diffrn_orient_matrix_UB_23      0.0196479000
_diffrn_orient_matrix_UB_31      -0.0646344000
_diffrn_orient_matrix_UB_32      -0.0831444000
_diffrn_orient_matrix_UB_33      0.0586247000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1672
_reflns_number_total             1907
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     61.93
_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         0.236
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         1907
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0368
_refine_ls_restrained_S_all      1.081
_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)+(0.0596P)²+0.2803P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1017
_refine_ls_wR_factor_ref         0.1070
_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
F1 F 0.51206(7) 0.16881(9) 0.54537(6) 0.0295(3) Uani 1 1 d . . .
O1 O 0.67559(7) 0.30407(10) 0.77952(6) 0.0221(3) Uani 1 1 d . . .
O2 O 0.40432(8) 0.61286(11) 0.61488(7) 0.0249(3) Uani 1 1 d . . .
H2 H 0.3800 0.6705 0.6465 0.037 Uiso 1 1 calc R . .
C12 C 0.52008(10) 0.44030(15) 0.61477(9) 0.0188(3) Uani 1 1 d . . .
H12 H 0.5041 0.4236 0.5584 0.023 Uiso 1 1 calc R . .
C11 C 0.47163(10) 0.53987(14) 0.65759(9) 0.0187(3) Uani 1 1 d . . .
C6 C 0.65110(11) 0.26586(15) 0.60681(9) 0.0197(3) Uani 1 1 d . . .
C7 C 0.59200(10) 0.36426(14) 0.65335(9) 0.0182(3) Uani 1 1 d . . .
C1 C 0.61087(11) 0.17450(15) 0.55234(9) 0.0229(3) Uani 1 1 d . . .
C9 C 0.56297(11) 0.48643(16) 0.78027(9) 0.0230(3) Uani 1 1 d . . .
H9 H 0.5773 0.5016 0.8372 0.028 Uiso 1 1 calc R . .
C14 C 0.80038(10) 0.36089(17) 0.67531(11) 0.0269(4) Uani 1 1 d . . .
H14A H 0.7774 0.4525 0.6636 0.032 Uiso 1 1 calc R . .
H14B H 0.8717 0.3593 0.6668 0.032 Uiso 1 1 calc R . .
C8 C 0.61178(10) 0.38782(14) 0.73746(9) 0.0195(3) Uani 1 1 d . . .
C5 C 0.75349(11) 0.26659(16) 0.61478(9) 0.0230(3) Uani 1 1 d . . .
C13 C 0.77842(11) 0.32724(18) 0.76567(10) 0.0266(4) Uani 1 1 d . . .
H13A H 0.8154 0.2466 0.7817 0.032 Uiso 1 1 calc R . .
H13B H 0.8004 0.4016 0.8014 0.032 Uiso 1 1 calc R . .
C2 C 0.66467(13) 0.08556(18) 0.50607(10) 0.0312(4) Uani 1 1 d . . .
H2A H 0.6337 0.0226 0.4708 0.037 Uiso 1 1 calc R . .
C10 C 0.49328(11) 0.56352(16) 0.74083(10) 0.0231(3) Uani 1 1 d . . .
H10 H 0.4604 0.6321 0.7703 0.028 Uiso 1 1 calc R . .
C3 C 0.76540(13) 0.09056(18) 0.51253(10) 0.0328(4) Uani 1 1 d . . .
H3 H 0.8045 0.0324 0.4801 0.039 Uiso 1 1 calc R . .
C4 C 0.80883(12) 0.18042(17) 0.56636(10) 0.0290(4) Uani 1 1 d . . .
H4 H 0.8778 0.1832 0.5703 0.035 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
F1 C1 1.3632(18) . ?
O1 C8 1.3907(17) . ?
O1 C13 1.4489(18) . ?
O2 H2 0.8400 . ?
O2 C11 1.3656(18) . ?
C12 H12 0.9500 . ?
C12 C11 1.385(2) . ?
C12 C7 1.394(2) . ?
C11 C10 1.394(2) . ?
C6 C7 1.482(2) . ?
C6 C1 1.384(2) . ?
C6 C5 1.413(2) . ?
C7 C8 1.402(2) . ?
C1 C2 1.378(2) . ?
C9 H9 0.9500 . ?
C9 C8 1.380(2) . ?
C9 C10 1.385(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C5 1.504(2) . ?
C14 C13 1.525(2) . ?
C5 C4 1.391(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C2 H2A 0.9500 . ?
C2 C3 1.389(3) . ?
C10 H10 0.9500 . ?
C3 H3 0.9500 . ?
C3 C4 1.386(3) . ?
C4 H4 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
C8 O1 C13 116.27(11) . . ?
C11 O2 H2 109.5 . . ?
C11 C12 H12 119.6 . . ?
C11 C12 C7 120.88(13) . . ?
C7 C12 H12 119.6 . . ?
O2 C11 C12 117.48(13) . . ?
O2 C11 C10 122.54(13) . . ?
C12 C11 C10 119.98(14) . . ?
C1 C6 C7 122.91(13) . . ?
C1 C6 C5 117.31(14) . . ?
C5 C6 C7 119.74(14) . . ?
C12 C7 C6 121.80(13) . . ?
C12 C7 C8 118.42(13) . . ?
C8 C7 C6 119.68(13) . . ?
F1 C1 C6 118.53(13) . . ?
F1 C1 C2 117.54(14) . . ?
C2 C1 C6 123.90(15) . . ?
C8 C9 H9 119.8 . . ?
C8 C9 C10 120.45(14) . . ?
C10 C9 H9 119.8 . . ?
H14A C14 H14B 107.7 . . ?
C5 C14 H14A 108.9 . . ?
C5 C14 H14B 108.9 . . ?
C5 C14 C13 113.29(13) . . ?
C13 C14 H14A 108.9 . . ?
C13 C14 H14B 108.9 . . ?
O1 C8 C7 119.43(13) . . ?
C9 C8 O1 119.72(13) . . ?
C9 C8 C7 120.65(13) . . ?
C6 C5 C14 119.26(14) . . ?
C4 C5 C6 119.35(15) . . ?
C4 C5 C14 121.39(14) . . ?
O1 C13 C14 112.05(12) . . ?
O1 C13 H13A 109.2 . . ?
O1 C13 H13B 109.2 . . ?
C14 C13 H13A 109.2 . . ?
C14 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
C1 C2 H2A 121.0 . . ?
C1 C2 C3 118.07(16) . . ?
C3 C2 H2A 121.0 . . ?
C11 C10 H10 120.2 . . ?
C9 C10 C11 119.59(14) . . ?
C9 C10 H10 120.2 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 119.96(15) . . ?
C4 C3 H3 120.0 . . ?
C5 C4 H4 119.3 . . ?
C3 C4 C5 121.34(15) . . ?
C3 C4 H4 119.3 . . ?

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
F1 C1 C2 C3 179.89(15) . . . . ?
O2 C11 C10 C9 -179.47(13) . . . . ?
C12 C11 C10 C9 -0.3(2) . . . . ?
C12 C7 C8 O1 173.20(12) . . . . ?
C12 C7 C8 C9 -1.7(2) . . . . ?
C11 C12 C7 C6 -174.24(13) . . . . ?
C11 C12 C7 C8 2.2(2) . . . . ?
C6 C7 C8 O1 -10.3(2) . . . . ?
C6 C7 C8 C9 174.79(13) . . . . ?
C6 C1 C2 C3 -2.0(2) . . . . ?
C6 C5 C4 C3 -2.3(2) . . . . ?
C7 C12 C11 O2 177.97(13) . . . . ?
C7 C12 C11 C10 -1.2(2) . . . . ?
C7 C6 C1 F1 -4.5(2) . . . . ?
C7 C6 C1 C2 177.43(14) . . . . ?
C7 C6 C5 C14 4.5(2) . . . . ?
C7 C6 C5 C4 -175.36(13) . . . . ?
C1 C6 C7 C12 -46.7(2) . . . . ?
C1 C6 C7 C8 136.92(15) . . . . ?
C1 C6 C5 C14 -177.96(13) . . . . ?
C1 C6 C5 C4 2.2(2) . . . . ?
C1 C2 C3 C4 2.0(2) . . . . ?
C14 C5 C4 C3 177.90(15) . . . . ?
C8 O1 C13 C14 -39.57(18) . . . . ?
C8 C9 C10 C11 0.8(2) . . . . ?
C5 C6 C7 C12 130.76(15) . . . . ?
C5 C6 C7 C8 -45.6(2) . . . . ?
C5 C6 C1 F1 177.99(13) . . . . ?
C5 C6 C1 C2 -0.1(2) . . . . ?
C5 C14 C13 O1 -48.24(18) . . . . ?
C13 O1 C8 C7 78.90(16) . . . . ?
C13 O1 C8 C9 -106.12(16) . . . . ?
C13 C14 C5 C6 67.66(18) . . . . ?
C13 C14 C5 C4 -112.52(16) . . . . ?
C2 C3 C4 C5 0.1(2) . . . . ?
C10 C9 C8 O1 -174.68(13) . . . . ?
C10 C9 C8 C7 0.2(2) . . . . ?
####################################################################### 
# 
# 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_10123
_database_code_depnum_ccdc_archive 'CCDC 2495484'
loop_
_audit_author_name
_audit_author_address
'Wang Mingan'
;China Agricultural University
China
;
_audit_update_record             
;
2025-10-15 deposited with the CCDC.	2025-11-24 downloaded from the CCDC.
;
_audit_creation_date             2025-09-12
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C14 H11 Cl O3'
_chemical_formula_sum            'C14 H11 Cl O3'
_chemical_formula_weight         262.68
_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'

_space_group_crystal_system      tetragonal
_space_group_IT_number           88
_space_group_name_H-M_alt        'I 41/a'
_space_group_name_Hall           '-I 4ad'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-y+3/4, x+1/4, z+1/4'
3 '-x, -y+1/2, z'
4 'y+1/4, -x+1/4, z+1/4'
5 'x+1/2, y+1/2, z+1/2'
6 '-y+5/4, x+3/4, z+3/4'
7 '-x+1/2, -y+1, z+1/2'
8 'y+3/4, -x+3/4, z+3/4'
9 '-x, -y, -z'
10 'y-3/4, -x-1/4, -z-1/4'
11 'x, y-1/2, -z'
12 '-y-1/4, x-1/4, -z-1/4'
13 '-x+1/2, -y+1/2, -z+1/2'
14 'y-1/4, -x+1/4, -z+1/4'
15 'x+1/2, y, -z+1/2'
16 '-y+1/4, x+1/4, -z+1/4'

_cell_length_a                   34.3840(8)
_cell_length_b                   34.3840(8)
_cell_length_c                   3.8114(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4506.0(5)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    2548
_cell_measurement_temperature    117.60(14)
_cell_measurement_theta_max      66.1990
_cell_measurement_theta_min      5.4400
_exptl_absorpt_coefficient_mu    2.989
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89009
_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            colorless
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2176
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.23
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       1
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            5201
_diffrn_reflns_theta_full        66.24
_diffrn_reflns_theta_max         66.24
_diffrn_reflns_theta_min         5.15
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      117.60(14)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9923
_diffrn_measured_fraction_theta_max 0.9762
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   21.00   52.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -57.0000    0.0000 31

#__ type_ start__ end____ width___ exp.time_
  2 omega    4.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -99.0000   90.0000 71

#__ type_ start__ end____ width___ exp.time_
  3 omega   30.00   75.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       98.5477  -30.0000   30.0000 45

#__ type_ start__ end____ width___ exp.time_
  4 omega   46.00   87.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       98.5477  -30.0000  -30.0000 41

#__ type_ start__ end____ width___ exp.time_
  5 omega   30.00   76.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       98.5477  -30.0000  -60.0000 46

#__ type_ start__ end____ width___ exp.time_
  6 omega   49.00   76.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       98.5477  -30.0000 -150.0000 27

#__ type_ start__ end____ width___ exp.time_
  7 omega  -30.00    3.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -57.0000    0.0000 33

#__ type_ start__ end____ width___ exp.time_
  8 omega  -20.00   19.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -77.0000  150.0000 39

#__ type_ start__ end____ width___ exp.time_
  9 omega  143.00  168.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       98.5477  125.0000   30.0000 25

#__ type_ start__ end____ width___ exp.time_
 10 omega  101.00  137.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       98.5477  125.0000    0.0000 36

#__ type_ start__ end____ width___ exp.time_
 11 omega   95.00  125.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       98.5477  125.0000   30.0000 30

#__ type_ start__ end____ width___ exp.time_
 12 omega   74.00  100.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  178.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 13 omega   -4.00   71.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.8017  -99.0000  -60.0000 75

#__ type_ start__ end____ width___ exp.time_
 14 omega    1.00   27.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.8017  -99.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 15 omega   23.00   49.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.8017  -37.0000  150.0000 26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0159566000
_diffrn_orient_matrix_UB_12      0.0418274000
_diffrn_orient_matrix_UB_13      -0.0148115000
_diffrn_orient_matrix_UB_21      0.0383485000
_diffrn_orient_matrix_UB_22      0.0153234000
_diffrn_orient_matrix_UB_23      0.1571059000
_diffrn_orient_matrix_UB_31      0.0168065000
_diffrn_orient_matrix_UB_32      0.0048169000
_diffrn_orient_matrix_UB_33      -0.3723366000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1726
_reflns_number_total             1940
_reflns_odcompleteness_completeness 99.23
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     61.93
_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         -0.266
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         1940
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0345
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0397P)²+3.5499P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0835
_refine_ls_wR_factor_ref         0.0886
_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
Cl1 Cl 0.930095(13) 1.075779(12) 0.15696(13) 0.02048(16) Uani 1 1 d . . .
O1 O 0.80336(4) 1.00989(4) -0.1682(4) 0.0203(3) Uani 1 1 d . . .
H1 H 0.7938 0.9882 -0.2203 0.030 Uiso 1 1 calc R . .
O2 O 0.96468(4) 0.82570(4) 0.6119(4) 0.0208(3) Uani 1 1 d . . .
O3 O 0.95511(3) 0.99691(4) 0.3017(3) 0.0153(3) Uani 1 1 d . . .
C4 C 0.97147(5) 0.89306(5) 0.4163(5) 0.0143(4) Uani 1 1 d . . .
H4 H 0.9988 0.8930 0.4527 0.017 Uiso 1 1 calc R . .
C5 C 0.95296(5) 0.92645(5) 0.2942(5) 0.0128(4) Uani 1 1 d . . .
C6 C 0.91775(5) 0.99834(5) 0.1752(5) 0.0133(4) Uani 1 1 d . . .
C7 C 0.84125(5) 1.00487(6) -0.0551(5) 0.0159(4) Uani 1 1 d . . .
C8 C 0.89162(5) 0.89325(5) 0.3052(5) 0.0153(4) Uani 1 1 d . . .
H8 H 0.8643 0.8930 0.2654 0.018 Uiso 1 1 calc R . .
C9 C 0.90971(5) 0.85991(5) 0.4239(5) 0.0170(4) Uani 1 1 d . . .
H9 H 0.8949 0.8370 0.4644 0.020 Uiso 1 1 calc R . .
C10 C 0.89508(5) 0.96466(5) 0.1368(5) 0.0134(4) Uani 1 1 d . . .
C11 C 0.94978(6) 0.85982(5) 0.4846(5) 0.0158(4) Uani 1 1 d . . .
C12 C 1.00471(6) 0.82537(6) 0.7115(6) 0.0225(5) Uani 1 1 d . . .
H12A H 1.0210 0.8279 0.5017 0.034 Uiso 1 1 calc R . .
H12B H 1.0107 0.8008 0.8308 0.034 Uiso 1 1 calc R . .
H12C H 1.0099 0.8472 0.8703 0.034 Uiso 1 1 calc R . .
C13 C 0.85658(5) 0.96859(5) 0.0220(5) 0.0151(4) Uani 1 1 d . . .
H13 H 0.8408 0.9461 -0.0034 0.018 Uiso 1 1 calc R . .
C14 C 0.91267(5) 0.92730(5) 0.2426(5) 0.0129(4) Uani 1 1 d . . .
C15 C 0.90170(5) 1.03425(5) 0.0992(5) 0.0144(4) Uani 1 1 d . . .
C16 C 0.86373(5) 1.03818(5) -0.0183(5) 0.0160(4) Uani 1 1 d . . .
H16 H 0.8533 1.0631 -0.0724 0.019 Uiso 1 1 calc R . .
C17 C 0.97578(5) 0.96206(5) 0.2005(5) 0.0141(4) Uani 1 1 d . . .
H17A H 1.0013 0.9613 0.3208 0.017 Uiso 1 1 calc R . .
H17B H 0.9806 0.9625 -0.0556 0.017 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
Cl1 C15 1.7436(18) . ?
O1 H1 0.8400 . ?
O1 C7 1.383(2) . ?
O2 C11 1.369(2) . ?
O2 C12 1.428(2) . ?
O3 C6 1.373(2) . ?
O3 C17 1.446(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.393(3) . ?
C4 C11 1.389(3) . ?
C5 C14 1.399(3) . ?
C5 C17 1.498(2) . ?
C6 C10 1.404(3) . ?
C6 C15 1.383(3) . ?
C7 C13 1.386(3) . ?
C7 C16 1.389(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.380(3) . ?
C8 C14 1.397(3) . ?
C9 H9 0.9500 . ?
C9 C11 1.397(3) . ?
C10 C13 1.401(3) . ?
C10 C14 1.476(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13 0.9500 . ?
C15 C16 1.387(3) . ?
C16 H16 0.9500 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?

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
C7 O1 H1 109.5 . . ?
C11 O2 C12 117.52(15) . . ?
C6 O3 C17 113.34(14) . . ?
C5 C4 H4 120.2 . . ?
C11 C4 H4 120.2 . . ?
C11 C4 C5 119.69(17) . . ?
C4 C5 C14 121.10(17) . . ?
C4 C5 C17 120.93(16) . . ?
C14 C5 C17 117.93(16) . . ?
O3 C6 C10 121.79(16) . . ?
O3 C6 C15 118.60(16) . . ?
C15 C6 C10 119.54(17) . . ?
O1 C7 C13 122.45(17) . . ?
O1 C7 C16 116.93(17) . . ?
C13 C7 C16 120.63(17) . . ?
C9 C8 H8 119.4 . . ?
C9 C8 C14 121.23(17) . . ?
C14 C8 H8 119.4 . . ?
C8 C9 H9 120.0 . . ?
C8 C9 C11 120.03(17) . . ?
C11 C9 H9 120.0 . . ?
C6 C10 C14 117.50(16) . . ?
C13 C10 C6 118.55(17) . . ?
C13 C10 C14 123.83(17) . . ?
O2 C11 C4 124.77(17) . . ?
O2 C11 C9 115.45(17) . . ?
C4 C11 C9 119.77(17) . . ?
O2 C12 H12A 109.5 . . ?
O2 C12 H12B 109.5 . . ?
O2 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C7 C13 C10 120.83(17) . . ?
C7 C13 H13 119.6 . . ?
C10 C13 H13 119.6 . . ?
C5 C14 C10 117.54(16) . . ?
C8 C14 C5 118.13(17) . . ?
C8 C14 C10 124.30(17) . . ?
C6 C15 Cl1 118.77(14) . . ?
C6 C15 C16 122.02(17) . . ?
C16 C15 Cl1 119.21(14) . . ?
C7 C16 H16 120.8 . . ?
C15 C16 C7 118.43(17) . . ?
C15 C16 H16 120.8 . . ?
O3 C17 C5 110.88(14) . . ?
O3 C17 H17A 109.5 . . ?
O3 C17 H17B 109.5 . . ?
C5 C17 H17A 109.5 . . ?
C5 C17 H17B 109.5 . . ?
H17A C17 H17B 108.1 . . ?

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 C15 C16 C7 -178.55(14) . . . . ?
O1 C7 C13 C10 -179.83(17) . . . . ?
O1 C7 C16 C15 179.13(17) . . . . ?
O3 C6 C10 C13 176.99(16) . . . . ?
O3 C6 C10 C14 0.9(3) . . . . ?
O3 C6 C15 Cl1 1.6(2) . . . . ?
O3 C6 C15 C16 -177.83(17) . . . . ?
C4 C5 C14 C8 -2.2(3) . . . . ?
C4 C5 C14 C10 175.75(16) . . . . ?
C4 C5 C17 O3 -142.48(17) . . . . ?
C5 C4 C11 O2 -178.56(17) . . . . ?
C5 C4 C11 C9 1.2(3) . . . . ?
C6 O3 C17 C5 -52.8(2) . . . . ?
C6 C10 C13 C7 0.6(3) . . . . ?
C6 C10 C14 C5 -14.7(3) . . . . ?
C6 C10 C14 C8 163.12(18) . . . . ?
C6 C15 C16 C7 0.9(3) . . . . ?
C8 C9 C11 O2 178.11(17) . . . . ?
C8 C9 C11 C4 -1.7(3) . . . . ?
C9 C8 C14 C5 1.8(3) . . . . ?
C9 C8 C14 C10 -176.07(17) . . . . ?
C10 C6 C15 Cl1 178.76(14) . . . . ?
C10 C6 C15 C16 -0.7(3) . . . . ?
C11 C4 C5 C14 0.8(3) . . . . ?
C11 C4 C5 C17 -176.80(17) . . . . ?
C12 O2 C11 C4 6.0(3) . . . . ?
C12 O2 C11 C9 -173.81(17) . . . . ?
C13 C7 C16 C15 -0.4(3) . . . . ?
C13 C10 C14 C5 169.37(17) . . . . ?
C13 C10 C14 C8 -12.8(3) . . . . ?
C14 C5 C17 O3 39.9(2) . . . . ?
C14 C8 C9 C11 0.2(3) . . . . ?
C14 C10 C13 C7 176.42(17) . . . . ?
C15 C6 C10 C13 0.0(3) . . . . ?
C15 C6 C10 C14 -176.18(16) . . . . ?
C16 C7 C13 C10 -0.3(3) . . . . ?
C17 O3 C6 C10 34.0(2) . . . . ?
C17 O3 C6 C15 -148.96(16) . . . . ?
C17 C5 C14 C8 175.41(17) . . . . ?
C17 C5 C14 C10 -6.6(2) . . . . ?
