# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_dd19334
_database_code_depnum_ccdc_archive 'CCDC 2021179'
loop_
_audit_author_name
_audit_author_address
'Qiuzi Wu'
; Zhejiang University of Technology
China
;
_audit_update_record             
;
2020-08-04 deposited with the CCDC.	2021-03-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H8 F N O3'
_chemical_formula_weight         245.20

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   4.1258(2)
_cell_length_b                   22.7811(8)
_cell_length_c                   11.8050(7)
_cell_angle_alpha                90
_cell_angle_beta                 93.5990(10)
_cell_angle_gamma                90
_cell_volume                     1107.37(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7854
_cell_measurement_theta_min      4.974
_cell_measurement_theta_max      54.796

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_F_000             504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.117
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6695
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16486
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.487
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             2144
_reflns_number_gt                1825
_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    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0579P)²+0.2830P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.044(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2144
_refine_ls_number_parameters     177
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0451
_refine_ls_wR_factor_ref         0.1251
_refine_ls_wR_factor_gt          0.1156
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.041
_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
F1 F 0.9332(3) 0.80268(6) 0.68360(10) 0.0730(4) Uani 0.85 1 d . . P A 1
F1' F 0.397(3) 0.8583(7) 0.3607(9) 0.094(4) Uani 0.15 1 d D . P B 2
O1 O 0.7868(5) 0.77433(6) 0.36075(12) 0.1065(7) Uani 1 1 d . . . . .
O2 O 0.7359(5) 0.50180(6) 0.60579(15) 0.1080(6) Uani 1 1 d . . . . .
O3 O 0.4441(6) 0.53609(7) 0.73066(18) 0.1211(8) Uani 1 1 d . . . . .
N1 N 0.5979(4) 0.54211(6) 0.64817(14) 0.0700(5) Uani 1 1 d . . . . .
C1 C 0.7396(4) 0.83904(7) 0.62759(14) 0.0561(4) Uani 1 1 d . . . . .
C2 C 0.6740(5) 0.89143(8) 0.67956(17) 0.0715(6) Uani 1 1 d . . . . .
H2 H 0.7579 0.8992 0.7530 0.086 Uiso 1 1 calc R U . . .
C3 C 0.4841(6) 0.93184(9) 0.6217(2) 0.0847(7) Uani 1 1 d . . . . .
H3 H 0.4343 0.9671 0.6564 0.102 Uiso 1 1 calc R U . . .
C4 C 0.3665(6) 0.92084(9) 0.5129(2) 0.0843(7) Uani 1 1 d . . . . .
H4 H 0.2375 0.9486 0.4738 0.101 Uiso 1 1 calc R U . . .
C5 C 0.4391(5) 0.86865(9) 0.46130(18) 0.0693(5) Uani 1 1 d D . . . .
C6 C 0.6244(4) 0.82562(7) 0.51846(13) 0.0512(4) Uani 1 1 d . . . . .
C7 C 0.7034(4) 0.77076(7) 0.45696(13) 0.0577(4) Uani 1 1 d . . . . .
C8 C 0.6721(4) 0.71165(6) 0.51003(12) 0.0461(4) Uani 1 1 d . . . . .
C9 C 0.7920(4) 0.66328(7) 0.45390(13) 0.0557(4) Uani 1 1 d . . . . .
H9 H 0.8892 0.6687 0.3857 0.067 Uiso 1 1 calc R U . . .
C10 C 0.7684(4) 0.60760(7) 0.49801(14) 0.0583(4) Uani 1 1 d . . . . .
H10 H 0.8507 0.5753 0.4611 0.070 Uiso 1 1 calc R U . . .
C11 C 0.6195(4) 0.60112(6) 0.59843(13) 0.0514(4) Uani 1 1 d . . . . .
C12 C 0.4916(4) 0.64771(7) 0.65490(13) 0.0501(4) Uani 1 1 d . . . . .
H12 H 0.3891 0.6418 0.7219 0.060 Uiso 1 1 calc R U . . .
C13 C 0.5185(4) 0.70327(6) 0.61010(12) 0.0469(4) Uani 1 1 d . . . . .
H13 H 0.4334 0.7353 0.6471 0.056 Uiso 1 1 calc R U . . .
H5 H 0.334(6) 0.8641(15) 0.3923(17) 0.050(9) Uiso 1 1 d 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
F1 C1 1.302(2) . ?
F1' C5 1.212(11) . ?
F1' H5 0.49(3) . ?
O1 C7 1.2100(19) . ?
O2 N1 1.206(2) . ?
O3 N1 1.203(2) . ?
N1 C11 1.472(2) . ?
C1 C2 1.377(2) . ?
C1 C6 1.379(2) . ?
C2 C3 1.365(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.367(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.391(3) . ?
C5 H5 0.905(18) . ?
C6 C7 1.492(2) . ?
C7 C8 1.494(2) . ?
C8 C13 1.3883(19) . ?
C8 C9 1.392(2) . ?
C9 C10 1.377(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.377(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.376(2) . ?
C12 C13 1.379(2) . ?
C12 H12 0.9300 . ?
C13 H13 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
C5 F1' H5 41(3) . . ?
O3 N1 O2 122.41(17) . . ?
O3 N1 C11 118.37(16) . . ?
O2 N1 C11 119.21(17) . . ?
F1 C1 C2 117.17(16) . . ?
F1 C1 C6 119.87(15) . . ?
C2 C1 C6 122.86(17) . . ?
C3 C2 C1 118.98(19) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 120.37(19) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C5 120.0(2) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
F1' C5 C4 125.4(8) . . ?
F1' C5 C6 112.2(7) . . ?
C4 C5 C6 121.5(2) . . ?
F1' C5 H5 21(2) . . ?
C4 C5 H5 113(2) . . ?
C6 C5 H5 125(2) . . ?
C1 C6 C5 116.32(16) . . ?
C1 C6 C7 124.56(15) . . ?
C5 C6 C7 118.98(16) . . ?
O1 C7 C6 118.96(15) . . ?
O1 C7 C8 119.42(15) . . ?
C6 C7 C8 121.58(13) . . ?
C13 C8 C9 119.40(14) . . ?
C13 C8 C7 122.46(13) . . ?
C9 C8 C7 118.10(13) . . ?
C10 C9 C8 120.89(14) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C11 118.05(14) . . ?
C9 C10 H10 121.0 . . ?
C11 C10 H10 121.0 . . ?
C12 C11 C10 122.66(14) . . ?
C12 C11 N1 118.46(14) . . ?
C10 C11 N1 118.87(14) . . ?
C11 C12 C13 118.66(14) . . ?
C11 C12 H12 120.7 . . ?
C13 C12 H12 120.7 . . ?
C12 C13 C8 120.31(13) . . ?
C12 C13 H13 119.8 . . ?
C8 C13 H13 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
F1 C1 C2 C3 177.06(17) . . . . ?
C6 C1 C2 C3 0.7(3) . . . . ?
C1 C2 C3 C4 -1.3(3) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C3 C4 C5 F1' -166.5(9) . . . . ?
C3 C4 C5 C6 1.7(3) . . . . ?
F1 C1 C6 C5 -175.25(16) . . . . ?
C2 C1 C6 C5 1.0(2) . . . . ?
F1 C1 C6 C7 0.5(2) . . . . ?
C2 C1 C6 C7 176.72(15) . . . . ?
F1' C5 C6 C1 167.5(8) . . . . ?
C4 C5 C6 C1 -2.2(3) . . . . ?
F1' C5 C6 C7 -8.5(8) . . . . ?
C4 C5 C6 C7 -178.17(17) . . . . ?
C1 C6 C7 O1 -132.4(2) . . . . ?
C5 C6 C7 O1 43.3(3) . . . . ?
C1 C6 C7 C8 49.5(2) . . . . ?
C5 C6 C7 C8 -134.82(17) . . . . ?
O1 C7 C8 C13 -167.01(19) . . . . ?
C6 C7 C8 C13 11.1(2) . . . . ?
O1 C7 C8 C9 10.6(3) . . . . ?
C6 C7 C8 C9 -171.37(15) . . . . ?
C13 C8 C9 C10 -1.9(2) . . . . ?
C7 C8 C9 C10 -179.54(16) . . . . ?
C8 C9 C10 C11 0.8(3) . . . . ?
C9 C10 C11 C12 0.7(3) . . . . ?
C9 C10 C11 N1 -178.76(15) . . . . ?
O3 N1 C11 C12 6.6(3) . . . . ?
O2 N1 C11 C12 -172.86(18) . . . . ?
O3 N1 C11 C10 -173.91(19) . . . . ?
O2 N1 C11 C10 6.7(3) . . . . ?
C10 C11 C12 C13 -1.1(2) . . . . ?
N1 C11 C12 C13 178.40(14) . . . . ?
C11 C12 C13 C8 -0.1(2) . . . . ?
C9 C8 C13 C12 1.5(2) . . . . ?
C7 C8 C13 C12 179.05(14) . . . . ?

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
C10 H10 O2 0.93 2.61 3.494(2) 160.1 3_766
C12 H12 O1 0.93 2.57 3.167(2) 122.5 4_576

_refine_diff_density_max         0.180
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.028

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_d8v18818
_database_code_depnum_ccdc_archive 'CCDC 2021189'
loop_
_audit_author_name
_audit_author_address
'Qiuzi Wu'
; Zhejiang University of Technology
China
;
_audit_update_record             
;
2020-08-04 deposited with the CCDC.	2021-03-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H13 F O2'
_chemical_formula_weight         244.25

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'
F F 0.0171 0.0103 '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           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

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

_cell_length_a                   8.2060(8)
_cell_length_b                   6.9192(6)
_cell_length_c                   22.420(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1273.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    2322
_cell_measurement_theta_min      5.386
_cell_measurement_theta_max      53.438

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_F_000             512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.093
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6035
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      190(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6041
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.643
_diffrn_reflns_theta_max         25.987
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             1348
_reflns_number_gt                1007
_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    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0688P)²+0.1439P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.088(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1348
_refine_ls_number_parameters     111
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0429
_refine_ls_wR_factor_ref         0.1351
_refine_ls_wR_factor_gt          0.1140
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.000
_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
F1 F 0.36278(17) 0.7500 0.60585(6) 0.0837(6) Uani 1 2 d S T P . .
O1 O 0.8480(2) 0.7500 0.55436(8) 0.0804(6) Uani 1 2 d S T P . .
O2 O 0.20455(17) 0.7500 0.40304(6) 0.0616(5) Uani 1 2 d S T P . .
C1 C 0.4062(3) 0.7500 0.54751(9) 0.0549(6) Uani 1 2 d S T P . .
C2 C 0.2796(2) 0.7500 0.50755(9) 0.0547(6) Uani 1 2 d S T P . .
H2 H 0.1696 0.7500 0.5207 0.066 Uiso 1 2 calc R U P . .
C3 C 0.3174(2) 0.7500 0.44739(9) 0.0514(5) Uani 1 2 d S T P . .
C4 C 0.4791(2) 0.7500 0.42911(9) 0.0554(6) Uani 1 2 d S T P . .
H4 H 0.5054 0.7500 0.3878 0.067 Uiso 1 2 calc R U P . .
C5 C 0.6000(3) 0.7500 0.47097(9) 0.0557(6) Uani 1 2 d S T P . .
H5 H 0.7101 0.7500 0.4578 0.067 Uiso 1 2 calc R U P . .
C6 C 0.5691(2) 0.7500 0.53241(9) 0.0518(5) Uani 1 2 d S T P . .
C7 C 0.7102(3) 0.7500 0.57407(11) 0.0612(6) Uani 1 2 d S T P . .
C8 C 0.6843(5) 0.7500 0.63989(13) 0.0881(9) Uani 1 2 d S T P . .
C9 C 0.0360(3) 0.7500 0.42026(9) 0.0638(6) Uani 1 2 d S T P . .
H9A H 0.0113 0.8661 0.4444 0.077 Uiso 0.5 1 calc R U P . .
H9B H 0.0113 0.6339 0.4444 0.077 Uiso 0.5 1 calc R U P . .
C10 C -0.0638(3) 0.7500 0.36473(10) 0.0623(6) Uani 1 2 d S T P . .
C11 C -0.1110(3) 0.5788(3) 0.33912(9) 0.0877(6) Uani 1 1 d . . . . .
H11 H -0.0804 0.4595 0.3568 0.105 Uiso 1 1 calc R U . . .
C12 C -0.2026(3) 0.5801(5) 0.28777(12) 0.1248(11) Uani 1 1 d . . . . .
H12 H -0.2357 0.4614 0.2702 0.150 Uiso 1 1 calc R U . . .
C13 C -0.2462(5) 0.7500 0.26205(16) 0.1344(17) Uani 1 2 d S T P . .
H13 H -0.3071 0.7500 0.2260 0.161 Uiso 1 2 calc R U P . .
H8A H 0.785(5) 0.7500 0.6579(15) 0.115(11) Uiso 1 2 d S . P . .
H8B H 0.619(3) 0.863(3) 0.6516(10) 0.114(8) Uiso 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
F1 C1 1.356(2) . ?
O1 C7 1.213(3) . ?
O2 C3 1.359(2) . ?
O2 C9 1.436(3) . ?
C1 C2 1.372(3) . ?
C1 C6 1.379(3) . ?
C2 C3 1.384(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.388(3) . ?
C4 C5 1.366(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.401(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.488(3) . ?
C7 C8 1.491(4) . ?
C8 H8A 0.92(4) . ?
C8 H8B 0.98(2) . ?
C9 C10 1.490(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.372(2) 7_575 ?
C10 C11 1.372(2) . ?
C11 C12 1.375(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.358(3) . ?
C12 H12 0.9500 . ?
C13 C12 1.357(3) 7_575 ?
C13 H13 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
C3 O2 C9 117.38(16) . . ?
F1 C1 C2 115.51(18) . . ?
F1 C1 C6 119.47(19) . . ?
C2 C1 C6 125.0(2) . . ?
C1 C2 C3 117.79(19) . . ?
C1 C2 H2 121.1 . . ?
C3 C2 H2 121.1 . . ?
O2 C3 C2 124.05(18) . . ?
O2 C3 C4 115.81(17) . . ?
C2 C3 C4 120.13(19) . . ?
C5 C4 C3 119.43(19) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 122.96(19) . . ?
C4 C5 H5 118.5 . . ?
C6 C5 H5 118.5 . . ?
C1 C6 C5 114.66(19) . . ?
C1 C6 C7 126.9(2) . . ?
C5 C6 C7 118.44(19) . . ?
O1 C7 C6 119.8(2) . . ?
O1 C7 C8 119.6(2) . . ?
C6 C7 C8 120.7(2) . . ?
C7 C8 H8A 108(2) . . ?
C7 C8 H8B 110.0(13) . . ?
H8A C8 H8B 111.9(18) . . ?
O2 C9 C10 107.75(17) . . ?
O2 C9 H9A 110.2 . . ?
C10 C9 H9A 110.2 . . ?
O2 C9 H9B 110.2 . . ?
C10 C9 H9B 110.2 . . ?
H9A C9 H9B 108.5 . . ?
C11 C10 C11 119.4(3) 7_575 . ?
C11 C10 C9 120.31(13) 7_575 . ?
C11 C10 C9 120.32(13) . . ?
C10 C11 C12 120.0(2) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C13 C12 C11 120.3(3) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C12 120.0(3) 7_575 . ?
C12 C13 H13 120.0 7_575 . ?
C12 C13 H13 120.0 . . ?

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 180.000(1) . . . . ?
C6 C1 C2 C3 0.000(1) . . . . ?
C9 O2 C3 C2 0.000(1) . . . . ?
C9 O2 C3 C4 180.000(0) . . . . ?
C1 C2 C3 O2 180.000(1) . . . . ?
C1 C2 C3 C4 0.000(1) . . . . ?
O2 C3 C4 C5 180.000(1) . . . . ?
C2 C3 C4 C5 0.000(1) . . . . ?
C3 C4 C5 C6 0.000(1) . . . . ?
F1 C1 C6 C5 180.000(1) . . . . ?
C2 C1 C6 C5 0.000(1) . . . . ?
F1 C1 C6 C7 0.000(1) . . . . ?
C2 C1 C6 C7 180.000(1) . . . . ?
C4 C5 C6 C1 0.000(1) . . . . ?
C4 C5 C6 C7 180.000(1) . . . . ?
C1 C6 C7 O1 180.000(1) . . . . ?
C5 C6 C7 O1 0.000(1) . . . . ?
C1 C6 C7 C8 0.000(1) . . . . ?
C5 C6 C7 C8 180.000(1) . . . . ?
C3 O2 C9 C10 180.000(0) . . . . ?
O2 C9 C10 C11 -90.38(18) . . . 7_575 ?
O2 C9 C10 C11 90.38(18) . . . . ?
C11 C10 C11 C12 1.0(4) 7_575 . . . ?
C9 C10 C11 C12 -179.8(2) . . . . ?
C10 C11 C12 C13 0.3(4) . . . . ?
C11 C12 C13 C12 -1.6(6) . . . 7_575 ?

_refine_diff_density_max         0.145
_refine_diff_density_min         -0.114
_refine_diff_density_rms         0.032

_shelxl_version_number           2013-4

