# Electronic Supplementary Material (ESI) for Green Chemistry.
# 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_po1
_database_code_depnum_ccdc_archive 'CCDC 2086181'
loop_
_audit_author_name
_audit_author_address
'Frank Rominger'
;Heidelberg University
Germany
;
_audit_update_record             
;
2021-05-27 deposited with the CCDC.	2021-08-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            Boscalid
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H12 Cl2 N2 O'
_chemical_formula_weight         343.20

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'
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.8126(13)
_cell_length_b                   11.5893(9)
_cell_length_c                   18.7010(15)
_cell_angle_alpha                90
_cell_angle_beta                 91.746(2)
_cell_angle_gamma                90
_cell_volume                     3208.9(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    3484
_cell_measurement_theta_min      2.18
_cell_measurement_theta_max      21.05

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_F_000             1408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.078
_exptl_crystal_size_min          0.032
_exptl_absorpt_coefficient_mu    0.409
_shelx_estimated_absorpt_T_min   0.930
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9114
_exptl_absorpt_correction_T_max  0.9582
_exptl_absorpt_process_details   
;
Sheldrick, G. M. (2008). SADABS. University of Göttingen, Germany.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'ImuS microsource'
_diffrn_measurement_device_type  'Bruker APEX-II Quazar area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28243
_diffrn_reflns_av_unetI/netI     0.0691
_diffrn_reflns_av_R_equivalents  0.0851
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.068
_diffrn_reflns_theta_max         24.406
_diffrn_reflns_theta_full        24.406
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5283
_reflns_number_gt                3100
_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    'SHELXT-2018/2 (Sheldrick 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0621P)²+1.7281P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5283
_refine_ls_number_parameters     423
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1146
_refine_ls_R_factor_gt           0.0537
_refine_ls_wR_factor_ref         0.1473
_refine_ls_wR_factor_gt          0.1205
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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
Cl1_1 Cl 0.63047(8) 0.09578(9) 0.69655(6) 0.0535(4) Uani 1 1 d . . . . .
Cl2_1 Cl 0.88157(9) -0.12841(10) 0.78041(7) 0.0612(4) Uani 1 1 d . . . . .
C10_1 C 0.6377(2) 0.3309(3) 0.77262(19) 0.0254(9) Uani 1 1 d . . . . .
O10_1 O 0.67213(17) 0.3641(2) 0.71740(12) 0.0320(6) Uani 1 1 d . . . . .
N11_1 N 0.6739(2) 0.3561(3) 0.83750(18) 0.0272(8) Uani 1 1 d . . . . .
H11_1 H 0.650(2) 0.326(3) 0.8661(19) 0.019(12) Uiso 1 1 d . . . . .
C11_1 C 0.5512(2) 0.2643(3) 0.77284(19) 0.0279(9) Uani 1 1 d . . . . .
C12_1 C 0.5385(3) 0.1596(3) 0.7374(2) 0.0328(10) Uani 1 1 d . . . . .
N13_1 N 0.4632(2) 0.1003(3) 0.73419(18) 0.0427(9) Uani 1 1 d . . . . .
C14_1 C 0.3933(3) 0.1442(4) 0.7682(2) 0.0465(12) Uani 1 1 d . . . . .
H14_1 H 0.337932 0.102854 0.766587 0.056 Uiso 1 1 calc R U . . .
C15_1 C 0.3973(3) 0.2461(4) 0.8053(2) 0.0462(12) Uani 1 1 d . . . . .
H15_1 H 0.345791 0.274496 0.828678 0.055 Uiso 1 1 calc R U . . .
C16_1 C 0.4778(3) 0.3068(3) 0.8083(2) 0.0392(10) Uani 1 1 d . . . . .
H16_1 H 0.482432 0.377034 0.834338 0.047 Uiso 1 1 calc R U . . .
C21_1 C 0.7534(3) 0.4259(3) 0.84491(18) 0.0286(9) Uani 1 1 d . . . . .
C22_1 C 0.8364(2) 0.3808(3) 0.82629(18) 0.0275(9) Uani 1 1 d . . . . .
C23_1 C 0.9101(3) 0.4553(4) 0.8270(2) 0.0394(11) Uani 1 1 d . . . . .
H23_1 H 0.967295 0.427581 0.812935 0.047 Uiso 1 1 calc R U . . .
C24_1 C 0.9013(3) 0.5688(4) 0.8480(2) 0.0463(12) Uani 1 1 d . . . . .
H24_1 H 0.951813 0.619181 0.847015 0.056 Uiso 1 1 calc R U . . .
C25_1 C 0.8192(3) 0.6094(4) 0.8703(2) 0.0436(11) Uani 1 1 d . . . . .
H25_1 H 0.813986 0.686393 0.887173 0.052 Uiso 1 1 calc R U . . .
C26_1 C 0.7450(3) 0.5383(3) 0.8679(2) 0.0348(10) Uani 1 1 d . . . . .
H26_1 H 0.688085 0.566489 0.882176 0.042 Uiso 1 1 calc R U . . .
C31_1 C 0.8468(2) 0.2557(3) 0.81119(19) 0.0286(9) Uani 1 1 d . . . . .
C32_1 C 0.8717(3) 0.2126(3) 0.7451(2) 0.0348(10) Uani 1 1 d . . . . .
H32_1 H 0.882676 0.264186 0.706866 0.042 Uiso 1 1 calc R U . . .
C33_1 C 0.8807(3) 0.0950(4) 0.7352(2) 0.0408(11) Uani 1 1 d . . . . .
H33_1 H 0.896096 0.066043 0.689587 0.049 Uiso 1 1 calc R U . . .
C34_1 C 0.8675(3) 0.0199(3) 0.7903(2) 0.0380(10) Uani 1 1 d . . . . .
C35_1 C 0.8438(3) 0.0605(4) 0.8554(2) 0.0398(11) Uani 1 1 d . . . . .
H35_1 H 0.835119 0.008488 0.893867 0.048 Uiso 1 1 calc R U . . .
C36_1 C 0.8324(3) 0.1770(3) 0.8651(2) 0.0383(10) Uani 1 1 d . . . . .
H36_1 H 0.814062 0.204239 0.910300 0.046 Uiso 1 1 calc R U . . .
Cl1_2 Cl 0.46799(10) 0.12536(11) 0.52765(9) 0.0831(5) Uani 1 1 d . . . . .
Cl2_2 Cl 0.81897(10) 0.86666(10) 0.59495(7) 0.0687(4) Uani 1 1 d . . . . .
O10_2 O 0.6292(2) 0.2681(3) 0.46508(14) 0.0526(8) Uani 1 1 d . . . . .
C10_2 C 0.6255(3) 0.2984(3) 0.5278(2) 0.0346(10) Uani 1 1 d . . . . .
N11_2 N 0.6974(2) 0.3070(3) 0.57291(17) 0.0310(8) Uani 1 1 d . . . . .
H11_2 H 0.687(3) 0.330(3) 0.619(2) 0.049(13) Uiso 1 1 d . . . . .
C11_2 C 0.5380(3) 0.3343(3) 0.55967(19) 0.0328(10) Uani 1 1 d . . . . .
C12_2 C 0.4639(3) 0.2634(4) 0.5627(2) 0.0449(11) Uani 1 1 d . . . . .
N13_2 N 0.3865(3) 0.2898(4) 0.5918(2) 0.0605(11) Uani 1 1 d . . . . .
C14_2 C 0.3801(4) 0.3962(5) 0.6185(3) 0.0616(14) Uani 1 1 d . . . . .
H14_2 H 0.325648 0.417108 0.640736 0.074 Uiso 1 1 calc R U . . .
C15_2 C 0.4465(4) 0.4763(4) 0.6157(2) 0.0563(13) Uani 1 1 d . . . . .
H15_2 H 0.437335 0.552380 0.632836 0.068 Uiso 1 1 calc R U . . .
C16_2 C 0.5282(3) 0.4446(4) 0.5873(2) 0.0468(12) Uani 1 1 d . . . . .
H16_2 H 0.576958 0.497876 0.586670 0.056 Uiso 1 1 calc R U . . .
C21_2 C 0.7864(3) 0.2736(3) 0.55401(18) 0.0319(10) Uani 1 1 d . . . . .
C22_2 C 0.8560(3) 0.3557(3) 0.55692(19) 0.0340(10) Uani 1 1 d . . . . .
C23_2 C 0.9426(3) 0.3174(4) 0.5403(2) 0.0425(11) Uani 1 1 d . . . . .
H23_2 H 0.991690 0.370075 0.542987 0.051 Uiso 1 1 calc R U . . .
C24_2 C 0.9580(3) 0.2058(4) 0.5203(2) 0.0496(12) Uani 1 1 d . . . . .
H24_2 H 1.017178 0.182386 0.508571 0.059 Uiso 1 1 calc R U . . .
C25_2 C 0.8882(3) 0.1268(4) 0.5170(2) 0.0474(12) Uani 1 1 d . . . . .
H25_2 H 0.898983 0.049548 0.502530 0.057 Uiso 1 1 calc R U . . .
C26_2 C 0.8029(3) 0.1608(4) 0.53493(19) 0.0384(10) Uani 1 1 d . . . . .
H26_2 H 0.754951 0.106316 0.534143 0.046 Uiso 1 1 calc R U . . .
C31_2 C 0.8417(3) 0.4804(3) 0.5720(2) 0.0341(10) Uani 1 1 d . . . . .
C32_2 C 0.7757(3) 0.5425(4) 0.5345(2) 0.0378(10) Uani 1 1 d . . . . .
H32_2 H 0.734900 0.503099 0.502815 0.045 Uiso 1 1 calc R U . . .
C33_2 C 0.7680(3) 0.6615(4) 0.5423(2) 0.0416(11) Uani 1 1 d . . . . .
H33_2 H 0.722914 0.703310 0.516065 0.050 Uiso 1 1 calc R U . . .
C34_2 C 0.8263(3) 0.7167(4) 0.5884(2) 0.0432(11) Uani 1 1 d . . . . .
C35_2 C 0.8912(3) 0.6580(4) 0.6277(2) 0.0507(12) Uani 1 1 d . . . . .
H35_2 H 0.930412 0.698019 0.660341 0.061 Uiso 1 1 calc R U . . .
C36_2 C 0.8987(3) 0.5406(4) 0.6192(2) 0.0469(12) Uani 1 1 d . . . . .
H36_2 H 0.943702 0.499798 0.646204 0.056 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_1 C12_1 1.747(4) . ?
Cl2_1 C34_1 1.742(4) . ?
C10_1 O10_1 1.227(4) . ?
C10_1 N11_1 1.343(5) . ?
C10_1 C11_1 1.497(5) . ?
N11_1 C21_1 1.432(5) . ?
N11_1 H11_1 0.73(3) . ?
C11_1 C16_1 1.381(5) . ?
C11_1 C12_1 1.392(5) . ?
C12_1 N13_1 1.311(5) . ?
N13_1 C14_1 1.332(5) . ?
C14_1 C15_1 1.370(6) . ?
C14_1 H14_1 0.9500 . ?
C15_1 C16_1 1.383(5) . ?
C15_1 H15_1 0.9500 . ?
C16_1 H16_1 0.9500 . ?
C21_1 C26_1 1.379(5) . ?
C21_1 C22_1 1.390(5) . ?
C22_1 C23_1 1.392(5) . ?
C22_1 C31_1 1.486(5) . ?
C23_1 C24_1 1.381(6) . ?
C23_1 H23_1 0.9500 . ?
C24_1 C25_1 1.380(6) . ?
C24_1 H24_1 0.9500 . ?
C25_1 C26_1 1.373(5) . ?
C25_1 H25_1 0.9500 . ?
C26_1 H26_1 0.9500 . ?
C31_1 C36_1 1.381(5) . ?
C31_1 C32_1 1.393(5) . ?
C32_1 C33_1 1.383(5) . ?
C32_1 H32_1 0.9500 . ?
C33_1 C34_1 1.367(5) . ?
C33_1 H33_1 0.9500 . ?
C34_1 C35_1 1.361(5) . ?
C35_1 C36_1 1.373(5) . ?
C35_1 H35_1 0.9500 . ?
C36_1 H36_1 0.9500 . ?
Cl1_2 C12_2 1.731(4) . ?
Cl2_2 C34_2 1.746(4) . ?
O10_2 C10_2 1.227(4) . ?
C10_2 N11_2 1.342(5) . ?
C10_2 C11_2 1.501(5) . ?
N11_2 C21_2 1.429(5) . ?
N11_2 H11_2 0.92(4) . ?
C11_2 C12_2 1.374(6) . ?
C11_2 C16_2 1.388(5) . ?
C12_2 N13_2 1.320(5) . ?
N13_2 C14_2 1.335(6) . ?
C14_2 C15_2 1.354(7) . ?
C14_2 H14_2 0.9500 . ?
C15_2 C16_2 1.386(6) . ?
C15_2 H15_2 0.9500 . ?
C16_2 H16_2 0.9500 . ?
C21_2 C26_2 1.378(5) . ?
C21_2 C22_2 1.402(5) . ?
C22_2 C23_2 1.401(5) . ?
C22_2 C31_2 1.490(5) . ?
C23_2 C24_2 1.367(6) . ?
C23_2 H23_2 0.9500 . ?
C24_2 C25_2 1.381(6) . ?
C24_2 H24_2 0.9500 . ?
C25_2 C26_2 1.375(6) . ?
C25_2 H25_2 0.9500 . ?
C26_2 H26_2 0.9500 . ?
C31_2 C32_2 1.388(5) . ?
C31_2 C36_2 1.391(5) . ?
C32_2 C33_2 1.391(5) . ?
C32_2 H32_2 0.9500 . ?
C33_2 C34_2 1.361(6) . ?
C33_2 H33_2 0.9500 . ?
C34_2 C35_2 1.373(6) . ?
C35_2 C36_2 1.375(6) . ?
C35_2 H35_2 0.9500 . ?
C36_2 H36_2 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
O10_1 C10_1 N11_1 121.8(3) . . ?
O10_1 C10_1 C11_1 122.8(3) . . ?
N11_1 C10_1 C11_1 115.3(3) . . ?
C10_1 N11_1 C21_1 120.9(3) . . ?
C10_1 N11_1 H11_1 112(3) . . ?
C21_1 N11_1 H11_1 127(3) . . ?
C16_1 C11_1 C12_1 116.2(4) . . ?
C16_1 C11_1 C10_1 120.3(3) . . ?
C12_1 C11_1 C10_1 123.4(3) . . ?
N13_1 C12_1 C11_1 125.6(4) . . ?
N13_1 C12_1 Cl1_1 115.6(3) . . ?
C11_1 C12_1 Cl1_1 118.8(3) . . ?
C12_1 N13_1 C14_1 116.7(4) . . ?
N13_1 C14_1 C15_1 123.3(4) . . ?
N13_1 C14_1 H14_1 118.3 . . ?
C15_1 C14_1 H14_1 118.3 . . ?
C14_1 C15_1 C16_1 118.9(4) . . ?
C14_1 C15_1 H15_1 120.6 . . ?
C16_1 C15_1 H15_1 120.6 . . ?
C11_1 C16_1 C15_1 119.3(4) . . ?
C11_1 C16_1 H16_1 120.4 . . ?
C15_1 C16_1 H16_1 120.4 . . ?
C26_1 C21_1 C22_1 121.4(4) . . ?
C26_1 C21_1 N11_1 118.9(3) . . ?
C22_1 C21_1 N11_1 119.7(3) . . ?
C21_1 C22_1 C23_1 117.7(4) . . ?
C21_1 C22_1 C31_1 120.7(3) . . ?
C23_1 C22_1 C31_1 121.4(3) . . ?
C24_1 C23_1 C22_1 120.8(4) . . ?
C24_1 C23_1 H23_1 119.6 . . ?
C22_1 C23_1 H23_1 119.6 . . ?
C25_1 C24_1 C23_1 120.2(4) . . ?
C25_1 C24_1 H24_1 119.9 . . ?
C23_1 C24_1 H24_1 119.9 . . ?
C26_1 C25_1 C24_1 119.8(4) . . ?
C26_1 C25_1 H25_1 120.1 . . ?
C24_1 C25_1 H25_1 120.1 . . ?
C25_1 C26_1 C21_1 119.9(4) . . ?
C25_1 C26_1 H26_1 120.1 . . ?
C21_1 C26_1 H26_1 120.1 . . ?
C36_1 C31_1 C32_1 117.5(4) . . ?
C36_1 C31_1 C22_1 119.2(3) . . ?
C32_1 C31_1 C22_1 123.4(3) . . ?
C33_1 C32_1 C31_1 120.2(4) . . ?
C33_1 C32_1 H32_1 119.9 . . ?
C31_1 C32_1 H32_1 119.9 . . ?
C34_1 C33_1 C32_1 120.6(4) . . ?
C34_1 C33_1 H33_1 119.7 . . ?
C32_1 C33_1 H33_1 119.7 . . ?
C35_1 C34_1 C33_1 120.1(4) . . ?
C35_1 C34_1 Cl2_1 118.0(3) . . ?
C33_1 C34_1 Cl2_1 121.8(3) . . ?
C34_1 C35_1 C36_1 119.6(4) . . ?
C34_1 C35_1 H35_1 120.2 . . ?
C36_1 C35_1 H35_1 120.2 . . ?
C35_1 C36_1 C31_1 122.1(4) . . ?
C35_1 C36_1 H36_1 119.0 . . ?
C31_1 C36_1 H36_1 119.0 . . ?
O10_2 C10_2 N11_2 124.3(4) . . ?
O10_2 C10_2 C11_2 121.5(4) . . ?
N11_2 C10_2 C11_2 114.1(3) . . ?
C10_2 N11_2 C21_2 123.1(3) . . ?
C10_2 N11_2 H11_2 117(2) . . ?
C21_2 N11_2 H11_2 119(2) . . ?
C12_2 C11_2 C16_2 116.3(4) . . ?
C12_2 C11_2 C10_2 123.5(4) . . ?
C16_2 C11_2 C10_2 120.3(4) . . ?
N13_2 C12_2 C11_2 125.7(4) . . ?
N13_2 C12_2 Cl1_2 114.3(4) . . ?
C11_2 C12_2 Cl1_2 120.0(3) . . ?
C12_2 N13_2 C14_2 116.1(4) . . ?
N13_2 C14_2 C15_2 123.9(4) . . ?
N13_2 C14_2 H14_2 118.0 . . ?
C15_2 C14_2 H14_2 118.0 . . ?
C14_2 C15_2 C16_2 118.5(5) . . ?
C14_2 C15_2 H15_2 120.7 . . ?
C16_2 C15_2 H15_2 120.7 . . ?
C15_2 C16_2 C11_2 119.2(4) . . ?
C15_2 C16_2 H16_2 120.4 . . ?
C11_2 C16_2 H16_2 120.4 . . ?
C26_2 C21_2 C22_2 121.2(4) . . ?
C26_2 C21_2 N11_2 119.5(4) . . ?
C22_2 C21_2 N11_2 119.3(3) . . ?
C23_2 C22_2 C21_2 117.0(4) . . ?
C23_2 C22_2 C31_2 119.1(4) . . ?
C21_2 C22_2 C31_2 123.8(4) . . ?
C24_2 C23_2 C22_2 121.4(4) . . ?
C24_2 C23_2 H23_2 119.3 . . ?
C22_2 C23_2 H23_2 119.3 . . ?
C23_2 C24_2 C25_2 120.6(4) . . ?
C23_2 C24_2 H24_2 119.7 . . ?
C25_2 C24_2 H24_2 119.7 . . ?
C26_2 C25_2 C24_2 119.4(4) . . ?
C26_2 C25_2 H25_2 120.3 . . ?
C24_2 C25_2 H25_2 120.3 . . ?
C25_2 C26_2 C21_2 120.4(4) . . ?
C25_2 C26_2 H26_2 119.8 . . ?
C21_2 C26_2 H26_2 119.8 . . ?
C32_2 C31_2 C36_2 117.7(4) . . ?
C32_2 C31_2 C22_2 120.7(4) . . ?
C36_2 C31_2 C22_2 121.3(4) . . ?
C31_2 C32_2 C33_2 121.3(4) . . ?
C31_2 C32_2 H32_2 119.4 . . ?
C33_2 C32_2 H32_2 119.4 . . ?
C34_2 C33_2 C32_2 118.7(4) . . ?
C34_2 C33_2 H33_2 120.6 . . ?
C32_2 C33_2 H33_2 120.6 . . ?
C33_2 C34_2 C35_2 121.8(4) . . ?
C33_2 C34_2 Cl2_2 118.2(4) . . ?
C35_2 C34_2 Cl2_2 120.0(4) . . ?
C34_2 C35_2 C36_2 119.1(4) . . ?
C34_2 C35_2 H35_2 120.5 . . ?
C36_2 C35_2 H35_2 120.5 . . ?
C35_2 C36_2 C31_2 121.4(4) . . ?
C35_2 C36_2 H36_2 119.3 . . ?
C31_2 C36_2 H36_2 119.3 . . ?

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
O10_1 C10_1 N11_1 C21_1 1.7(5) . . . . ?
C11_1 C10_1 N11_1 C21_1 -175.8(3) . . . . ?
O10_1 C10_1 C11_1 C16_1 -120.8(4) . . . . ?
N11_1 C10_1 C11_1 C16_1 56.7(5) . . . . ?
O10_1 C10_1 C11_1 C12_1 58.0(5) . . . . ?
N11_1 C10_1 C11_1 C12_1 -124.6(4) . . . . ?
C16_1 C11_1 C12_1 N13_1 1.1(6) . . . . ?
C10_1 C11_1 C12_1 N13_1 -177.7(4) . . . . ?
C16_1 C11_1 C12_1 Cl1_1 -175.7(3) . . . . ?
C10_1 C11_1 C12_1 Cl1_1 5.5(5) . . . . ?
C11_1 C12_1 N13_1 C14_1 -0.4(6) . . . . ?
Cl1_1 C12_1 N13_1 C14_1 176.6(3) . . . . ?
C12_1 N13_1 C14_1 C15_1 -0.1(6) . . . . ?
N13_1 C14_1 C15_1 C16_1 -0.2(7) . . . . ?
C12_1 C11_1 C16_1 C15_1 -1.4(6) . . . . ?
C10_1 C11_1 C16_1 C15_1 177.4(4) . . . . ?
C14_1 C15_1 C16_1 C11_1 1.0(6) . . . . ?
C10_1 N11_1 C21_1 C26_1 105.6(4) . . . . ?
C10_1 N11_1 C21_1 C22_1 -71.9(5) . . . . ?
C26_1 C21_1 C22_1 C23_1 -4.2(5) . . . . ?
N11_1 C21_1 C22_1 C23_1 173.3(3) . . . . ?
C26_1 C21_1 C22_1 C31_1 171.6(3) . . . . ?
N11_1 C21_1 C22_1 C31_1 -11.0(5) . . . . ?
C21_1 C22_1 C23_1 C24_1 2.2(6) . . . . ?
C31_1 C22_1 C23_1 C24_1 -173.6(4) . . . . ?
C22_1 C23_1 C24_1 C25_1 1.6(6) . . . . ?
C23_1 C24_1 C25_1 C26_1 -3.5(6) . . . . ?
C24_1 C25_1 C26_1 C21_1 1.5(6) . . . . ?
C22_1 C21_1 C26_1 C25_1 2.4(6) . . . . ?
N11_1 C21_1 C26_1 C25_1 -175.1(4) . . . . ?
C21_1 C22_1 C31_1 C36_1 -63.0(5) . . . . ?
C23_1 C22_1 C31_1 C36_1 112.6(4) . . . . ?
C21_1 C22_1 C31_1 C32_1 118.0(4) . . . . ?
C23_1 C22_1 C31_1 C32_1 -66.4(5) . . . . ?
C36_1 C31_1 C32_1 C33_1 0.5(6) . . . . ?
C22_1 C31_1 C32_1 C33_1 179.5(4) . . . . ?
C31_1 C32_1 C33_1 C34_1 -1.7(6) . . . . ?
C32_1 C33_1 C34_1 C35_1 1.2(6) . . . . ?
C32_1 C33_1 C34_1 Cl2_1 -178.0(3) . . . . ?
C33_1 C34_1 C35_1 C36_1 0.6(6) . . . . ?
Cl2_1 C34_1 C35_1 C36_1 179.8(3) . . . . ?
C34_1 C35_1 C36_1 C31_1 -1.9(6) . . . . ?
C32_1 C31_1 C36_1 C35_1 1.3(6) . . . . ?
C22_1 C31_1 C36_1 C35_1 -177.8(4) . . . . ?
O10_2 C10_2 N11_2 C21_2 -4.6(6) . . . . ?
C11_2 C10_2 N11_2 C21_2 177.9(3) . . . . ?
O10_2 C10_2 C11_2 C12_2 59.5(6) . . . . ?
N11_2 C10_2 C11_2 C12_2 -122.9(4) . . . . ?
O10_2 C10_2 C11_2 C16_2 -119.6(4) . . . . ?
N11_2 C10_2 C11_2 C16_2 58.0(5) . . . . ?
C16_2 C11_2 C12_2 N13_2 -2.8(6) . . . . ?
C10_2 C11_2 C12_2 N13_2 178.0(4) . . . . ?
C16_2 C11_2 C12_2 Cl1_2 178.3(3) . . . . ?
C10_2 C11_2 C12_2 Cl1_2 -0.8(6) . . . . ?
C11_2 C12_2 N13_2 C14_2 2.1(7) . . . . ?
Cl1_2 C12_2 N13_2 C14_2 -179.0(3) . . . . ?
C12_2 N13_2 C14_2 C15_2 1.4(7) . . . . ?
N13_2 C14_2 C15_2 C16_2 -3.9(7) . . . . ?
C14_2 C15_2 C16_2 C11_2 2.9(6) . . . . ?
C12_2 C11_2 C16_2 C15_2 0.2(6) . . . . ?
C10_2 C11_2 C16_2 C15_2 179.3(4) . . . . ?
C10_2 N11_2 C21_2 C26_2 -60.6(5) . . . . ?
C10_2 N11_2 C21_2 C22_2 121.0(4) . . . . ?
C26_2 C21_2 C22_2 C23_2 -0.6(5) . . . . ?
N11_2 C21_2 C22_2 C23_2 177.8(3) . . . . ?
C26_2 C21_2 C22_2 C31_2 175.4(4) . . . . ?
N11_2 C21_2 C22_2 C31_2 -6.1(5) . . . . ?
C21_2 C22_2 C23_2 C24_2 1.7(6) . . . . ?
C31_2 C22_2 C23_2 C24_2 -174.6(4) . . . . ?
C22_2 C23_2 C24_2 C25_2 -1.0(6) . . . . ?
C23_2 C24_2 C25_2 C26_2 -0.8(6) . . . . ?
C24_2 C25_2 C26_2 C21_2 1.9(6) . . . . ?
C22_2 C21_2 C26_2 C25_2 -1.1(6) . . . . ?
N11_2 C21_2 C26_2 C25_2 -179.6(3) . . . . ?
C23_2 C22_2 C31_2 C32_2 125.8(4) . . . . ?
C21_2 C22_2 C31_2 C32_2 -50.2(5) . . . . ?
C23_2 C22_2 C31_2 C36_2 -48.4(5) . . . . ?
C21_2 C22_2 C31_2 C36_2 135.6(4) . . . . ?
C36_2 C31_2 C32_2 C33_2 1.6(6) . . . . ?
C22_2 C31_2 C32_2 C33_2 -172.9(4) . . . . ?
C31_2 C32_2 C33_2 C34_2 -0.6(6) . . . . ?
C32_2 C33_2 C34_2 C35_2 -0.9(6) . . . . ?
C32_2 C33_2 C34_2 Cl2_2 177.4(3) . . . . ?
C33_2 C34_2 C35_2 C36_2 1.4(7) . . . . ?
Cl2_2 C34_2 C35_2 C36_2 -176.9(3) . . . . ?
C34_2 C35_2 C36_2 C31_2 -0.3(7) . . . . ?
C32_2 C31_2 C36_2 C35_2 -1.2(6) . . . . ?
C22_2 C31_2 C36_2 C35_2 173.3(4) . . . . ?

_refine_diff_density_max         0.277
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.058

####################################################################### 
# 
# 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_po2
_database_code_depnum_ccdc_archive 'CCDC 2086182'
loop_
_audit_author_name
_audit_author_address
'Frank Rominger'
;Heidelberg University
Germany
;
_audit_update_record             
;
2021-05-27 deposited with the CCDC.	2021-08-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            Fluxapyroxad
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H12 F5 N3 O'
_chemical_formula_weight         381.31

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'
N N 0.0311 0.0180 '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'
F F 0.0727 0.0534 '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'

_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+1/2'
'x+1/2, -y+1/2, -z'
'-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                   12.8826(6)
_cell_length_b                   9.2515(5)
_cell_length_c                   28.4963(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3396.3(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    7606
_cell_measurement_theta_min      5.89
_cell_measurement_theta_max      66.56

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_F_000             1552
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.055
_exptl_crystal_size_min          0.024
_exptl_absorpt_coefficient_mu    1.163
_shelx_estimated_absorpt_T_min   0.883
_shelx_estimated_absorpt_T_max   0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.439
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_process_details   'STOE X-AREA LANA'
_exptl_absorpt_special_details   'X-Area LANA 1.70.0.0 (STOE, 2017)'
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Genix3D Cu HF'
_diffrn_measurement_device_type  'STOE Stadivari'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_detector_area_resol_mean 5.81
_diffrn_reflns_number            10749
_diffrn_reflns_av_unetI/netI     0.0480
_diffrn_reflns_av_R_equivalents  0.0529
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         6.090
_diffrn_reflns_theta_max         66.676
_diffrn_reflns_theta_full        66.676
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.975
_reflns_number_total             2929
_reflns_number_gt                1728
_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       'X-Area Pilatus3_SV 1.31.153.0 (STOE, 2018)'
_computing_cell_refinement       'X-Area Recipe 1.33.0.0 (STOE, 2015)'
_computing_data_reduction        'X-Area Integrate 1.74.2.0 (STOE, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0477P)²+1.3541P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2929
_refine_ls_number_parameters     288
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1054
_refine_ls_R_factor_gt           0.0510
_refine_ls_wR_factor_ref         0.1203
_refine_ls_wR_factor_gt          0.0997
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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
C1 C 0.1933(2) 0.7062(3) 0.61241(9) 0.0368(7) Uani 1 1 d . . . . .
C2 C 0.2591(2) 0.6701(3) 0.57521(9) 0.0406(7) Uani 1 1 d . . . . .
C3 C 0.2140(3) 0.6283(4) 0.53253(11) 0.0511(8) Uani 1 1 d . . . . .
H3 H 0.256(3) 0.606(4) 0.5032(12) 0.077 Uiso 1 1 d . U . . .
C4 C 0.1069(3) 0.6271(4) 0.52714(12) 0.0531(9) Uani 1 1 d . . . . .
H4 H 0.079(3) 0.599(4) 0.4956(13) 0.080 Uiso 1 1 d . U . . .
C5 C 0.0436(3) 0.6651(4) 0.56379(11) 0.0499(8) Uani 1 1 d . . . . .
H5 H -0.032(3) 0.673(4) 0.5598(12) 0.075 Uiso 1 1 d . U . . .
C6 C 0.0865(2) 0.7040(3) 0.60674(11) 0.0446(8) Uani 1 1 d . . . . .
H6 H 0.042(3) 0.730(4) 0.6330(12) 0.067 Uiso 1 1 d . U . . .
N7 N 0.23312(19) 0.7495(3) 0.65694(8) 0.0393(6) Uani 1 1 d . . . . .
H7 H 0.216(2) 0.830(4) 0.6654(11) 0.059 Uiso 1 1 d . U . . .
O8 O 0.32225(15) 0.5443(2) 0.67342(6) 0.0423(5) Uani 1 1 d . . . . .
C8 C 0.2919(2) 0.6658(3) 0.68473(9) 0.0349(6) Uani 1 1 d . . . . .
C9 C 0.3205(2) 0.7292(3) 0.73050(9) 0.0337(6) Uani 1 1 d . . . . .
C10 C 0.4043(2) 0.6902(3) 0.75960(10) 0.0393(7) Uani 1 1 d . . . . .
N11 N 0.40680(18) 0.7676(3) 0.79901(9) 0.0456(6) Uani 1 1 d . . . . .
N12 N 0.32339(18) 0.8553(3) 0.79556(8) 0.0420(6) Uani 1 1 d . . . . .
C13 C 0.2708(2) 0.8355(3) 0.75542(10) 0.0403(7) Uani 1 1 d . . . . .
H13 H 0.210(2) 0.891(3) 0.7488(10) 0.060 Uiso 1 1 d . U . . .
C14 C 0.4861(2) 0.5806(4) 0.75041(14) 0.0587(9) Uani 1 1 d . . . . .
H14 H 0.480525 0.541430 0.717805 0.070 Uiso 1 1 calc R U . A 1
F15A F 0.4742(7) 0.4704(6) 0.7838(3) 0.091(3) Uani 0.656(18) 1 d . . P B 1
F16A F 0.5790(3) 0.6331(7) 0.7583(4) 0.086(3) Uani 0.656(18) 1 d . . P B 1
F15B F 0.5435(17) 0.544(2) 0.7847(5) 0.125(10) Uani 0.344(18) 1 d . . P B 2
F16B F 0.5640(9) 0.6646(12) 0.7197(10) 0.125(7) Uani 0.344(18) 1 d . . P B 2
C17 C 0.3009(3) 0.9578(4) 0.83294(11) 0.0609(9) Uani 1 1 d . . . . .
H17A H 0.356916 1.029311 0.834814 0.091 Uiso 1 1 calc R U . . .
H17B H 0.295544 0.906228 0.862872 0.091 Uiso 1 1 calc R U . . .
H17C H 0.235175 1.007039 0.826296 0.091 Uiso 1 1 calc R U . . .
C21 C 0.3744(2) 0.6773(3) 0.57893(10) 0.0428(7) Uani 1 1 d . . . . .
C22 C 0.4337(3) 0.5613(4) 0.56306(11) 0.0493(8) Uani 1 1 d . . . . .
H22 H 0.402(3) 0.468(4) 0.5518(12) 0.074 Uiso 1 1 d . U . . .
F23 F 0.59956(15) 0.4574(2) 0.55127(7) 0.0785(6) Uani 1 1 d . . . . .
C23 C 0.5402(3) 0.5699(4) 0.56559(11) 0.0548(9) Uani 1 1 d . . . . .
F24 F 0.69406(14) 0.6948(2) 0.58495(8) 0.0829(7) Uani 1 1 d . . . . .
C24 C 0.5890(2) 0.6887(4) 0.58310(12) 0.0582(9) Uani 1 1 d . . . . .
F25 F 0.58001(15) 0.9199(2) 0.61522(9) 0.0891(8) Uani 1 1 d . . . . .
C25 C 0.5300(3) 0.8023(4) 0.59852(12) 0.0572(9) Uani 1 1 d . . . . .
C26 C 0.4240(2) 0.7989(4) 0.59683(12) 0.0507(8) Uani 1 1 d . . . . .
H26 H 0.387(3) 0.881(4) 0.6071(12) 0.076 Uiso 1 1 d . 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
C1 C6 1.386(4) . ?
C1 C2 1.398(4) . ?
C1 N7 1.426(3) . ?
C2 C3 1.402(4) . ?
C2 C21 1.490(4) . ?
C3 C4 1.388(4) . ?
C3 H3 1.02(3) . ?
C4 C5 1.371(5) . ?
C4 H4 1.00(4) . ?
C5 C6 1.390(4) . ?
C5 H5 0.98(3) . ?
C6 H6 0.98(3) . ?
N7 C8 1.342(4) . ?
N7 H7 0.82(3) . ?
O8 C8 1.233(3) . ?
C8 C9 1.477(4) . ?
C9 C13 1.372(4) . ?
C9 C10 1.408(4) . ?
C10 N11 1.332(4) . ?
C10 C14 1.486(4) . ?
N11 N12 1.350(3) . ?
N12 C13 1.342(3) . ?
N12 C17 1.455(4) . ?
C13 H13 0.96(3) . ?
C14 F15B 1.271(9) . ?
C14 F16A 1.311(5) . ?
C14 F15A 1.403(5) . ?
C14 F16B 1.542(15) . ?
C14 H14 1.0000 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C21 C26 1.390(4) . ?
C21 C22 1.394(4) . ?
C22 C23 1.376(5) . ?
C22 H22 1.01(4) . ?
F23 C23 1.355(4) . ?
C23 C24 1.361(5) . ?
F24 C24 1.355(4) . ?
C24 C25 1.369(5) . ?
F25 C25 1.351(4) . ?
C25 C26 1.367(4) . ?
C26 H26 0.94(4) . ?

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
C6 C1 C2 120.7(3) . . ?
C6 C1 N7 117.7(3) . . ?
C2 C1 N7 121.6(3) . . ?
C1 C2 C3 118.2(3) . . ?
C1 C2 C21 122.7(3) . . ?
C3 C2 C21 119.2(3) . . ?
C4 C3 C2 120.7(3) . . ?
C4 C3 H3 116(2) . . ?
C2 C3 H3 123(2) . . ?
C5 C4 C3 120.3(3) . . ?
C5 C4 H4 123(2) . . ?
C3 C4 H4 117(2) . . ?
C4 C5 C6 120.0(3) . . ?
C4 C5 H5 121(2) . . ?
C6 C5 H5 118(2) . . ?
C1 C6 C5 120.1(3) . . ?
C1 C6 H6 120(2) . . ?
C5 C6 H6 120(2) . . ?
C8 N7 C1 124.5(2) . . ?
C8 N7 H7 121(2) . . ?
C1 N7 H7 115(2) . . ?
O8 C8 N7 123.4(3) . . ?
O8 C8 C9 120.9(2) . . ?
N7 C8 C9 115.6(2) . . ?
C13 C9 C10 103.7(2) . . ?
C13 C9 C8 128.7(3) . . ?
C10 C9 C8 127.6(2) . . ?
N11 C10 C9 112.2(2) . . ?
N11 C10 C14 119.8(3) . . ?
C9 C10 C14 128.0(3) . . ?
C10 N11 N12 104.0(2) . . ?
C13 N12 N11 112.5(2) . . ?
C13 N12 C17 127.7(3) . . ?
N11 N12 C17 119.8(2) . . ?
N12 C13 C9 107.6(2) . . ?
N12 C13 H13 120.7(19) . . ?
C9 C13 H13 131.7(19) . . ?
F16A C14 F15A 104.7(4) . . ?
F15B C14 C10 117.3(5) . . ?
F16A C14 C10 111.4(3) . . ?
F15A C14 C10 107.4(3) . . ?
F15B C14 F16B 101.1(9) . . ?
C10 C14 F16B 102.6(5) . . ?
F16A C14 H14 111.1 . . ?
F15A C14 H14 111.1 . . ?
C10 C14 H14 111.1 . . ?
N12 C17 H17A 109.5 . . ?
N12 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N12 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C26 C21 C22 119.4(3) . . ?
C26 C21 C2 121.4(3) . . ?
C22 C21 C2 119.3(3) . . ?
C23 C22 C21 119.0(3) . . ?
C23 C22 H22 118.4(19) . . ?
C21 C22 H22 122(2) . . ?
F23 C23 C24 118.0(3) . . ?
F23 C23 C22 120.2(3) . . ?
C24 C23 C22 121.8(3) . . ?
F24 C24 C23 120.6(4) . . ?
F24 C24 C25 120.7(4) . . ?
C23 C24 C25 118.7(3) . . ?
F25 C25 C26 120.5(3) . . ?
F25 C25 C24 117.8(3) . . ?
C26 C25 C24 121.7(3) . . ?
C25 C26 C21 119.4(3) . . ?
C25 C26 H26 118(2) . . ?
C21 C26 H26 122(2) . . ?

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
C6 C1 C2 C3 -1.6(4) . . . . ?
N7 C1 C2 C3 179.9(3) . . . . ?
C6 C1 C2 C21 177.1(3) . . . . ?
N7 C1 C2 C21 -1.4(4) . . . . ?
C1 C2 C3 C4 1.9(5) . . . . ?
C21 C2 C3 C4 -176.9(3) . . . . ?
C2 C3 C4 C5 -0.9(5) . . . . ?
C3 C4 C5 C6 -0.5(5) . . . . ?
C2 C1 C6 C5 0.3(4) . . . . ?
N7 C1 C6 C5 178.9(3) . . . . ?
C4 C5 C6 C1 0.8(5) . . . . ?
C6 C1 N7 C8 119.3(3) . . . . ?
C2 C1 N7 C8 -62.1(4) . . . . ?
C1 N7 C8 O8 4.0(4) . . . . ?
C1 N7 C8 C9 -177.0(2) . . . . ?
O8 C8 C9 C13 -156.9(3) . . . . ?
N7 C8 C9 C13 24.0(4) . . . . ?
O8 C8 C9 C10 20.7(4) . . . . ?
N7 C8 C9 C10 -158.3(3) . . . . ?
C13 C9 C10 N11 -0.8(3) . . . . ?
C8 C9 C10 N11 -178.9(3) . . . . ?
C13 C9 C10 C14 -179.1(3) . . . . ?
C8 C9 C10 C14 2.8(5) . . . . ?
C9 C10 N11 N12 0.9(3) . . . . ?
C14 C10 N11 N12 179.4(3) . . . . ?
C10 N11 N12 C13 -0.7(3) . . . . ?
C10 N11 N12 C17 -179.7(3) . . . . ?
N11 N12 C13 C9 0.2(3) . . . . ?
C17 N12 C13 C9 179.2(3) . . . . ?
C10 C9 C13 N12 0.3(3) . . . . ?
C8 C9 C13 N12 178.4(3) . . . . ?
N11 C10 C14 F15B 14.1(17) . . . . ?
C9 C10 C14 F15B -167.7(16) . . . . ?
N11 C10 C14 F16A -47.3(7) . . . . ?
C9 C10 C14 F16A 130.9(6) . . . . ?
N11 C10 C14 F15A 66.7(6) . . . . ?
C9 C10 C14 F15A -115.0(6) . . . . ?
N11 C10 C14 F16B -95.7(10) . . . . ?
C9 C10 C14 F16B 82.6(11) . . . . ?
C1 C2 C21 C26 -48.8(4) . . . . ?
C3 C2 C21 C26 129.9(3) . . . . ?
C1 C2 C21 C22 132.8(3) . . . . ?
C3 C2 C21 C22 -48.5(4) . . . . ?
C26 C21 C22 C23 0.1(4) . . . . ?
C2 C21 C22 C23 178.5(3) . . . . ?
C21 C22 C23 F23 178.7(3) . . . . ?
C21 C22 C23 C24 -0.1(5) . . . . ?
F23 C23 C24 F24 1.6(5) . . . . ?
C22 C23 C24 F24 -179.6(3) . . . . ?
F23 C23 C24 C25 -178.8(3) . . . . ?
C22 C23 C24 C25 -0.1(5) . . . . ?
F24 C24 C25 F25 0.4(5) . . . . ?
C23 C24 C25 F25 -179.2(3) . . . . ?
F24 C24 C25 C26 179.7(3) . . . . ?
C23 C24 C25 C26 0.2(5) . . . . ?
F25 C25 C26 C21 179.2(3) . . . . ?
C24 C25 C26 C21 -0.2(5) . . . . ?
C22 C21 C26 C25 0.0(5) . . . . ?
C2 C21 C26 C25 -178.4(3) . . . . ?

_refine_diff_density_max         0.256
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.042

####################################################################### 
# 
# 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_po3
_database_code_depnum_ccdc_archive 'CCDC 2086183'
loop_
_audit_author_name
_audit_author_address
'Frank Rominger'
;Heidelberg University
Germany
;
_audit_update_record             
;
2021-05-27 deposited with the CCDC.	2021-08-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            Bixafen
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H12 Cl2 F3 N3 O'
_chemical_formula_weight         414.21

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'
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.8929(7)
_cell_length_b                   18.0476(11)
_cell_length_c                   8.6239(5)
_cell_angle_alpha                90
_cell_angle_beta                 110.0924(15)
_cell_angle_gamma                90
_cell_volume                     1738.37(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    2652
_cell_measurement_theta_min      2.76
_cell_measurement_theta_max      21.59

_exptl_crystal_description       plank
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.583
_exptl_crystal_F_000             840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.143
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.021
_exptl_absorpt_coefficient_mu    0.418
_shelx_estimated_absorpt_T_min   0.943
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9268
_exptl_absorpt_correction_T_max  0.9590
_exptl_absorpt_process_details   
;
Sheldrick, G. M. (2008). SADABS. University of Göttingen, Germany.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'ImuS microsource'
_diffrn_measurement_device_type  'Bruker APEX-II Quazar area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17929
_diffrn_reflns_av_unetI/netI     0.0624
_diffrn_reflns_av_R_equivalents  0.0695
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.823
_diffrn_reflns_theta_max         26.367
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3545
_reflns_number_gt                2247
_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    'SHELXT-2018/2 (Sheldrick 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0368P)²+1.9244P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3545
_refine_ls_number_parameters     248
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0968
_refine_ls_R_factor_gt           0.0523
_refine_ls_wR_factor_ref         0.1227
_refine_ls_wR_factor_gt          0.1039
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_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
C1 C 0.5690(3) 0.56795(16) 0.7531(4) 0.0237(7) Uani 1 1 d . . . . .
O1 O 0.46832(19) 0.55193(12) 0.7495(3) 0.0339(6) Uani 1 1 d . . . . .
N1 N 0.5901(2) 0.62103(14) 0.6543(3) 0.0268(6) Uani 1 1 d . . . . .
H1 H 0.655(3) 0.6348(19) 0.676(4) 0.040 Uiso 1 1 d . U . . .
C2 C 0.6734(3) 0.52895(15) 0.8670(4) 0.0223(7) Uani 1 1 d . . . . .
C3 C 0.7939(3) 0.52060(16) 0.8781(4) 0.0247(7) Uani 1 1 d . . . . .
N4 N 0.8539(2) 0.47566(14) 1.0009(3) 0.0310(6) Uani 1 1 d . . . . .
N5 N 0.7734(2) 0.45550(14) 1.0708(3) 0.0297(6) Uani 1 1 d . . . . .
C6 C 0.6658(3) 0.48514(16) 0.9949(4) 0.0266(7) Uani 1 1 d . . . . .
H6 H 0.596323 0.477575 1.023523 0.032 Uiso 1 1 calc R U . . .
C7 C 0.8600(3) 0.54681(19) 0.7704(4) 0.0380(9) Uani 1 1 d . . . . .
H7 H 0.945209 0.529884 0.815452 0.046 Uiso 1 1 calc R U . . .
F8 F 0.80684(19) 0.52097(13) 0.6135(3) 0.0569(6) Uani 1 1 d . . . . .
F9 F 0.85543(18) 0.62188(12) 0.7569(3) 0.0598(7) Uani 1 1 d . . . . .
C10 C 0.8091(3) 0.4050(2) 1.2113(5) 0.0492(10) Uani 1 1 d . . . . .
H10A H 0.744286 0.401008 1.256704 0.074 Uiso 1 1 calc R U . . .
H10B H 0.881266 0.424071 1.296433 0.074 Uiso 1 1 calc R U . . .
H10C H 0.825856 0.356014 1.175310 0.074 Uiso 1 1 calc R U . . .
C11 C 0.5011(3) 0.65805(16) 0.5234(4) 0.0245(7) Uani 1 1 d . . . . .
C12 C 0.5172(3) 0.73233(16) 0.4866(4) 0.0230(7) Uani 1 1 d . . . . .
C13 C 0.4287(3) 0.76592(17) 0.3542(4) 0.0267(7) Uani 1 1 d . . . . .
H13 H 0.437412 0.816019 0.326442 0.032 Uiso 1 1 calc R U . . .
C14 C 0.3291(3) 0.72623(17) 0.2643(4) 0.0285(7) Uani 1 1 d . . . . .
C15 C 0.3115(3) 0.65441(17) 0.3004(4) 0.0300(8) Uani 1 1 d . . . . .
H15 H 0.240949 0.628571 0.237602 0.036 Uiso 1 1 calc R U . . .
C16 C 0.3985(3) 0.62014(17) 0.4303(4) 0.0281(7) Uani 1 1 d . . . . .
H16 H 0.387912 0.570041 0.456162 0.034 Uiso 1 1 calc R U . . .
F18 F 0.24566(16) 0.75975(10) 0.1340(2) 0.0417(5) Uani 1 1 d . . . . .
C21 C 0.6257(3) 0.77654(16) 0.5807(4) 0.0245(7) Uani 1 1 d . . . . .
C22 C 0.7370(3) 0.75925(17) 0.5726(4) 0.0328(8) Uani 1 1 d . . . . .
H22 H 0.744806 0.718240 0.507978 0.039 Uiso 1 1 calc R U . . .
C23 C 0.8370(3) 0.80089(18) 0.6573(4) 0.0354(8) Uani 1 1 d . . . . .
C24 C 0.8264(3) 0.86087(18) 0.7524(4) 0.0336(8) Uani 1 1 d . . . . .
C25 C 0.7156(3) 0.88014(18) 0.7584(4) 0.0345(8) Uani 1 1 d . . . . .
H25 H 0.707855 0.921938 0.820887 0.041 Uiso 1 1 calc R U . . .
C26 C 0.6153(3) 0.83807(17) 0.6725(4) 0.0291(7) Uani 1 1 d . . . . .
H26 H 0.539086 0.851467 0.676499 0.035 Uiso 1 1 calc R U . . .
Cl1 Cl 0.97339(8) 0.77686(6) 0.64143(16) 0.0614(3) Uani 1 1 d . . . . .
Cl2 Cl 0.95136(9) 0.91211(6) 0.86195(12) 0.0544(3) Uani 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.222(3) . ?
C1 N1 1.361(4) . ?
C1 C2 1.471(4) . ?
N1 C11 1.421(4) . ?
N1 H1 0.77(3) . ?
C2 C6 1.385(4) . ?
C2 C3 1.411(4) . ?
C3 N4 1.330(4) . ?
C3 C7 1.485(4) . ?
N4 N5 1.346(3) . ?
N5 C6 1.333(4) . ?
N5 C10 1.458(4) . ?
C6 H6 0.9500 . ?
C7 F9 1.359(4) . ?
C7 F8 1.364(4) . ?
C7 H7 1.0000 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C16 1.389(4) . ?
C11 C12 1.406(4) . ?
C12 C13 1.398(4) . ?
C12 C21 1.497(4) . ?
C13 C14 1.373(4) . ?
C13 H13 0.9500 . ?
C14 F18 1.359(3) . ?
C14 C15 1.366(4) . ?
C15 C16 1.382(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C21 C22 1.385(4) . ?
C21 C26 1.394(4) . ?
C22 C23 1.385(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.390(5) . ?
C23 Cl1 1.729(3) . ?
C24 C25 1.381(5) . ?
C24 Cl2 1.729(3) . ?
C25 C26 1.394(4) . ?
C25 H25 0.9500 . ?
C26 H26 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
O1 C1 N1 122.7(3) . . ?
O1 C1 C2 119.9(3) . . ?
N1 C1 C2 117.4(3) . . ?
C1 N1 C11 125.5(3) . . ?
C1 N1 H1 117(3) . . ?
C11 N1 H1 117(3) . . ?
C6 C2 C3 103.1(3) . . ?
C6 C2 C1 122.3(3) . . ?
C3 C2 C1 134.5(3) . . ?
N4 C3 C2 112.0(3) . . ?
N4 C3 C7 115.9(3) . . ?
C2 C3 C7 131.9(3) . . ?
C3 N4 N5 104.6(2) . . ?
C6 N5 N4 112.5(2) . . ?
C6 N5 C10 128.0(3) . . ?
N4 N5 C10 119.5(3) . . ?
N5 C6 C2 107.8(3) . . ?
N5 C6 H6 126.1 . . ?
C2 C6 H6 126.1 . . ?
F9 C7 F8 105.3(3) . . ?
F9 C7 C3 110.9(3) . . ?
F8 C7 C3 110.3(3) . . ?
F9 C7 H7 110.1 . . ?
F8 C7 H7 110.1 . . ?
C3 C7 H7 110.1 . . ?
N5 C10 H10A 109.5 . . ?
N5 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N5 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C16 C11 C12 120.0(3) . . ?
C16 C11 N1 119.6(3) . . ?
C12 C11 N1 120.4(3) . . ?
C13 C12 C11 118.4(3) . . ?
C13 C12 C21 118.6(3) . . ?
C11 C12 C21 123.0(3) . . ?
C14 C13 C12 119.8(3) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
F18 C14 C15 119.0(3) . . ?
F18 C14 C13 118.5(3) . . ?
C15 C14 C13 122.4(3) . . ?
C14 C15 C16 118.6(3) . . ?
C14 C15 H15 120.7 . . ?
C16 C15 H15 120.7 . . ?
C15 C16 C11 120.8(3) . . ?
C15 C16 H16 119.6 . . ?
C11 C16 H16 119.6 . . ?
C22 C21 C26 118.7(3) . . ?
C22 C21 C12 120.9(3) . . ?
C26 C21 C12 120.3(3) . . ?
C23 C22 C21 121.0(3) . . ?
C23 C22 H22 119.5 . . ?
C21 C22 H22 119.5 . . ?
C22 C23 C24 119.9(3) . . ?
C22 C23 Cl1 118.8(3) . . ?
C24 C23 Cl1 121.3(3) . . ?
C25 C24 C23 120.0(3) . . ?
C25 C24 Cl2 119.8(3) . . ?
C23 C24 Cl2 120.3(3) . . ?
C24 C25 C26 119.8(3) . . ?
C24 C25 H25 120.1 . . ?
C26 C25 H25 120.1 . . ?
C21 C26 C25 120.6(3) . . ?
C21 C26 H26 119.7 . . ?
C25 C26 H26 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 N1 C11 -7.8(5) . . . . ?
C2 C1 N1 C11 171.9(3) . . . . ?
O1 C1 C2 C6 -13.5(4) . . . . ?
N1 C1 C2 C6 166.8(3) . . . . ?
O1 C1 C2 C3 162.8(3) . . . . ?
N1 C1 C2 C3 -16.9(5) . . . . ?
C6 C2 C3 N4 0.2(3) . . . . ?
C1 C2 C3 N4 -176.5(3) . . . . ?
C6 C2 C3 C7 173.8(3) . . . . ?
C1 C2 C3 C7 -2.9(6) . . . . ?
C2 C3 N4 N5 -0.7(3) . . . . ?
C7 C3 N4 N5 -175.4(3) . . . . ?
C3 N4 N5 C6 1.0(3) . . . . ?
C3 N4 N5 C10 179.6(3) . . . . ?
N4 N5 C6 C2 -0.8(4) . . . . ?
C10 N5 C6 C2 -179.4(3) . . . . ?
C3 C2 C6 N5 0.3(3) . . . . ?
C1 C2 C6 N5 177.6(3) . . . . ?
N4 C3 C7 F9 -127.8(3) . . . . ?
C2 C3 C7 F9 58.8(5) . . . . ?
N4 C3 C7 F8 115.9(3) . . . . ?
C2 C3 C7 F8 -57.5(5) . . . . ?
C1 N1 C11 C16 -34.0(4) . . . . ?
C1 N1 C11 C12 146.7(3) . . . . ?
C16 C11 C12 C13 -0.8(4) . . . . ?
N1 C11 C12 C13 178.4(3) . . . . ?
C16 C11 C12 C21 -179.6(3) . . . . ?
N1 C11 C12 C21 -0.4(4) . . . . ?
C11 C12 C13 C14 0.2(4) . . . . ?
C21 C12 C13 C14 179.0(3) . . . . ?
C12 C13 C14 F18 -178.7(3) . . . . ?
C12 C13 C14 C15 0.9(5) . . . . ?
F18 C14 C15 C16 178.2(3) . . . . ?
C13 C14 C15 C16 -1.4(5) . . . . ?
C14 C15 C16 C11 0.7(5) . . . . ?
C12 C11 C16 C15 0.4(5) . . . . ?
N1 C11 C16 C15 -178.9(3) . . . . ?
C13 C12 C21 C22 -111.4(3) . . . . ?
C11 C12 C21 C22 67.4(4) . . . . ?
C13 C12 C21 C26 65.7(4) . . . . ?
C11 C12 C21 C26 -115.5(3) . . . . ?
C26 C21 C22 C23 1.7(5) . . . . ?
C12 C21 C22 C23 178.9(3) . . . . ?
C21 C22 C23 C24 0.1(5) . . . . ?
C21 C22 C23 Cl1 -179.7(2) . . . . ?
C22 C23 C24 C25 -1.9(5) . . . . ?
Cl1 C23 C24 C25 177.9(3) . . . . ?
C22 C23 C24 Cl2 178.7(3) . . . . ?
Cl1 C23 C24 Cl2 -1.5(4) . . . . ?
C23 C24 C25 C26 1.7(5) . . . . ?
Cl2 C24 C25 C26 -178.9(2) . . . . ?
C22 C21 C26 C25 -1.9(5) . . . . ?
C12 C21 C26 C25 -179.1(3) . . . . ?
C24 C25 C26 C21 0.2(5) . . . . ?

_refine_diff_density_max         0.304
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.064

