# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_200528-2-jjl
_database_code_depnum_ccdc_archive 'CCDC 2026456'
loop_
_audit_author_name
_audit_author_address
'junlong jia'
;Tianjin University of Technology
China
;
_audit_update_record             
;
2020-08-31 deposited with the CCDC.	2020-11-25 downloaded from the CCDC.
;
_audit_creation_date             2020-07-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H15 Cl F4 N4 O3, C5 H8 O4'
_chemical_formula_sum            'C26 H23 Cl F4 N4 O7'
_chemical_formula_weight         614.93
_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'
F F 0.0727 0.0534 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   23.6243(3)
_cell_length_b                   7.42220(10)
_cell_length_c                   15.1901(2)
_cell_angle_alpha                90
_cell_angle_beta                 99.0380(10)
_cell_angle_gamma                90
_cell_volume                     2630.43(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10414
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      79.0170
_cell_measurement_theta_min      3.7950
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.038
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62042
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0762
_diffrn_reflns_av_unetI/netI     0.0647
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            17014
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.067
_diffrn_reflns_theta_max         67.067
_diffrn_reflns_theta_min         3.789
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -17.00  31.00   0.50    0.50    --    0.00 -77.00-180.00   96
  2  ω     41.00  87.00   0.50    0.50    --    0.00  57.00-120.00   92
  3  ω     45.00  89.00   0.50    0.50    --    0.00  82.00 -90.00   88
  4  ω    -28.00  23.00   0.50    0.50    --    0.00  57.00-120.00  102
  5  ω    -46.00   3.00   0.50    0.50    --    0.00  19.00-180.00   98
  6  ω     17.00 138.00   0.50    2.60    --  106.20 -82.00 -60.00  242
  7  ω     49.00 141.00   0.50    2.60    --  106.20 -77.00  60.00  184
  8  ω    156.00 191.00   0.50    2.60    --  106.20  30.00 -90.00   70
  9  ω    129.00 196.00   0.50    2.60    --  106.20  77.00  30.00  134
 10  ω     32.00  88.00   0.50    2.60    --  106.20 -45.00  60.00  112
 11  ω     73.00 150.00   0.50    2.60    --  106.20  30.00 -90.00  154
 12  ω     31.00 134.00   0.50    2.60    --  106.20 -45.00 -60.00  206
 13  ω     17.00  66.00   0.50    2.60    --  106.20 -77.00-180.00   98
 14  ω     87.00 112.00   0.50    2.60    --  106.20 -77.00-180.00   50
 15  ω     90.00 123.00   0.50    2.60    --  106.20 -82.00-120.00   66
 16  ω    142.00 193.00   0.50    2.60    --  106.20  15.00 120.00  102
 17  ω     25.00 100.00   0.50    2.60    --  106.20  15.00 120.00  150
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual offset/far'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0236605000
_diffrn_orient_matrix_UB_12      0.1897924000
_diffrn_orient_matrix_UB_13      0.0133395000
_diffrn_orient_matrix_UB_21      -0.0613040000
_diffrn_orient_matrix_UB_22      -0.0769038000
_diffrn_orient_matrix_UB_23      -0.0114521000
_diffrn_orient_matrix_UB_31      0.0066764000
_diffrn_orient_matrix_UB_32      -0.0337872000
_diffrn_orient_matrix_UB_33      0.1011454000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4298
_reflns_number_total             4692
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     385
_refine_ls_number_reflns         4692
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0452
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0694P)²+0.6726P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1197
_refine_ls_wR_factor_ref         0.1225
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(F4) = Uanis(F5)
3. Others
 Sof(H14)=Sof(F5)=1-FVAR(1)
 Sof(F4)=Sof(H10)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B), C23(H23A,H23B), C24(H24A,H24B)
4.b Aromatic/amide H refined with riding coordinates:
 N4(H4), N1(H1), N2(H2), C3(H3), C14(H14), C16(H16), C10(H10), C11(H11),
 C13(H13), C5(H5), C19(H19), C6(H6), C18(H18)
4.c Tetrahedral OH refined with riding coordinates:
 O7(H7)
4.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
4.e Idealised tetrahedral OH refined as rotating group:
 O5(H5A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.21438(2) 0.33789(6) 1.13562(3) 0.03160(15) Uani 1 1 d . . . . .
F1 F 0.12504(4) 0.50374(14) 0.99568(7) 0.0311(3) Uani 1 1 d . . . . .
F3 F 0.12036(4) 0.40898(16) 0.86109(7) 0.0357(3) Uani 1 1 d . . . . .
F2 F 0.12414(5) 0.21908(15) 0.96901(9) 0.0378(3) Uani 1 1 d . . . . .
O3 O 0.71592(5) 0.37565(17) 0.35574(8) 0.0277(3) Uani 1 1 d . . . . .
O5 O 0.83383(5) 0.50988(18) 0.69379(8) 0.0296(3) Uani 1 1 d . . . . .
H5A H 0.806776 0.483474 0.655219 0.044 Uiso 1 1 calc GR . . . .
O1 O 0.40804(5) 0.28129(18) 0.84738(8) 0.0300(3) Uani 1 1 d . . . . .
O7 O 1.01671(5) 0.77164(17) 1.01154(8) 0.0285(3) Uani 1 1 d . . . . .
H7 H 1.013208 0.865523 1.038630 0.043 Uiso 1 1 calc R . . . .
O6 O 0.97223(6) 0.93280(16) 0.89736(8) 0.0303(3) Uani 1 1 d . . . . .
O2 O 0.56739(5) 0.21361(18) 0.54277(9) 0.0306(3) Uani 1 1 d . . . . .
F4 F 0.41207(5) 0.05278(17) 0.68720(9) 0.0289(3) Uani 0.789(2) 1 d . . P A 1
O4 O 0.88070(6) 0.3272(2) 0.61433(9) 0.0380(3) Uani 1 1 d . . . . .
N3 N 0.73448(6) 0.40271(19) 0.59186(9) 0.0224(3) Uani 1 1 d . . . . .
N4 N 0.79862(6) 0.35443(19) 0.45246(10) 0.0235(3) Uani 1 1 d . . . . .
H4 H 0.814256 0.347418 0.507431 0.028 Uiso 1 1 calc R . . . .
N1 N 0.31824(6) 0.4036(2) 0.80680(10) 0.0233(3) Uani 1 1 d . . . . .
H1 H 0.296049 0.450172 0.762311 0.028 Uiso 1 1 calc R . . . .
N2 N 0.38401(6) 0.4168(2) 0.71212(10) 0.0245(3) Uani 1 1 d . . . . .
H2 H 0.359687 0.487090 0.681042 0.029 Uiso 1 1 calc R . . . .
C8 C 0.37321(7) 0.3598(2) 0.79368(11) 0.0213(3) Uani 1 1 d . . . . .
C22 C 0.88014(7) 0.4193(2) 0.67978(11) 0.0237(4) Uani 1 1 d . . . . .
C26 C 0.99121(7) 0.7875(2) 0.93031(11) 0.0216(3) Uani 1 1 d . . . . .
C9 C 0.43368(7) 0.3646(2) 0.67696(11) 0.0217(4) Uani 1 1 d . . . . .
C3 C 0.23563(7) 0.3911(2) 0.87948(11) 0.0213(3) Uani 1 1 d . . . . .
H3 H 0.213233 0.409998 0.824213 0.026 Uiso 1 1 calc R . . . .
C14 C 0.44669(7) 0.1848(2) 0.66334(11) 0.0231(4) Uani 1 1 d . . . . .
H14 H 0.423760 0.096145 0.682876 0.028 Uiso 0.211(2) 1 calc R . P A 2
C15 C 0.62120(7) 0.2851(2) 0.56214(12) 0.0227(4) Uani 1 1 d . . . . .
C20 C 0.74213(7) 0.3632(2) 0.43306(11) 0.0204(3) Uani 1 1 d . . . . .
C4 C 0.29521(7) 0.3795(2) 0.88549(11) 0.0208(3) Uani 1 1 d . . . . .
C17 C 0.70884(7) 0.3531(2) 0.50996(11) 0.0198(3) Uani 1 1 d . . . . .
C12 C 0.52549(7) 0.2671(2) 0.59309(11) 0.0244(4) Uani 1 1 d . . . . .
C16 C 0.65272(7) 0.2930(2) 0.49258(11) 0.0218(3) Uani 1 1 d . . . . .
H16 H 0.636455 0.258669 0.435287 0.026 Uiso 1 1 calc R . . . .
C10 C 0.46944(7) 0.4942(2) 0.64881(11) 0.0235(4) Uani 1 1 d . . . . .
H10 H 0.462491 0.615188 0.658833 0.028 Uiso 0.789(2) 1 calc R . P A 1
C2 C 0.20938(7) 0.3750(2) 0.95488(12) 0.0220(4) Uani 1 1 d . . . . .
C11 C 0.51508(7) 0.4480(2) 0.60628(11) 0.0256(4) Uani 1 1 d . . . . .
H11 H 0.538216 0.536333 0.587012 0.031 Uiso 1 1 calc R . . . .
C25 C 0.98608(8) 0.6182(2) 0.87646(12) 0.0247(4) Uani 1 1 d . . . . .
H25A H 0.982652 0.516929 0.915626 0.030 Uiso 1 1 calc R . . . .
H25B H 1.020899 0.601717 0.851010 0.030 Uiso 1 1 calc R . . . .
C13 C 0.49227(7) 0.1320(2) 0.62196(11) 0.0238(4) Uani 1 1 d . . . . .
H13 H 0.500238 0.010925 0.613890 0.029 Uiso 1 1 calc R . . . .
C7 C 0.24347(8) 0.3496(2) 1.03727(11) 0.0231(4) Uani 1 1 d . . . . .
C5 C 0.32846(7) 0.3488(2) 0.96818(12) 0.0238(4) Uani 1 1 d . . . . .
H5 H 0.368044 0.337724 0.973051 0.029 Uiso 1 1 calc R . . . .
C19 C 0.64607(8) 0.3397(2) 0.64645(12) 0.0259(4) Uani 1 1 d . . . . .
H19 H 0.625575 0.338718 0.693951 0.031 Uiso 1 1 calc R . . . .
C1 C 0.14491(8) 0.3782(2) 0.94503(12) 0.0254(4) Uani 1 1 d . . . . .
C23 C 0.93062(7) 0.4397(2) 0.75260(12) 0.0260(4) Uani 1 1 d . . . . .
H23A H 0.965295 0.422534 0.726851 0.031 Uiso 1 1 calc R . . . .
H23B H 0.929089 0.343905 0.795612 0.031 Uiso 1 1 calc R . . . .
C6 C 0.30216(8) 0.3349(2) 1.04302(12) 0.0259(4) Uani 1 1 d . . . . .
H6 H 0.324451 0.315188 1.098308 0.031 Uiso 1 1 calc R . . . .
C24 C 0.93532(8) 0.6176(2) 0.80197(13) 0.0285(4) Uani 1 1 d . . . . .
H24A H 0.939526 0.714461 0.760591 0.034 Uiso 1 1 calc R . . . .
H24B H 0.900436 0.638900 0.826608 0.034 Uiso 1 1 calc R . . . .
C18 C 0.70279(8) 0.3962(2) 0.65752(12) 0.0257(4) Uani 1 1 d . . . . .
H18 H 0.719864 0.431738 0.714218 0.031 Uiso 1 1 calc R . . . .
C21 C 0.83512(8) 0.3562(3) 0.38385(13) 0.0296(4) Uani 1 1 d . . . . .
H21A H 0.821061 0.270416 0.338333 0.044 Uiso 1 1 calc GR . . . .
H21B H 0.873569 0.324937 0.409788 0.044 Uiso 1 1 calc GR . . . .
H21C H 0.834846 0.474387 0.358124 0.044 Uiso 1 1 calc GR . . . .
F5 F 0.4546(2) 0.6774(6) 0.6587(3) 0.0289(3) Uani 0.211(2) 1 d . . P A 2


_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 C7 1.7420(16) . ?
F1 C1 1.3392(19) . ?
F3 C1 1.335(2) . ?
F2 C1 1.351(2) . ?
O3 C20 1.242(2) . ?
O5 H5A 0.8200 . ?
O5 C22 1.329(2) . ?
O1 C8 1.213(2) . ?
O7 H7 0.8200 . ?
O7 C26 1.291(2) . ?
O6 C26 1.242(2) . ?
O2 C15 1.366(2) . ?
O2 C12 1.3996(19) . ?
F4 C14 1.361(2) . ?
O4 C22 1.208(2) . ?
N3 C17 1.347(2) . ?
N3 C18 1.339(2) . ?
N4 H4 0.8600 . ?
N4 C20 1.322(2) . ?
N4 C21 1.453(2) . ?
N1 H1 0.8600 . ?
N1 C8 1.383(2) . ?
N1 C4 1.400(2) . ?
N2 H2 0.8600 . ?
N2 C8 1.370(2) . ?
N2 C9 1.418(2) . ?
C22 C23 1.501(2) . ?
C26 C25 1.494(2) . ?
C9 C14 1.392(2) . ?
C9 C10 1.391(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.399(2) . ?
C3 C2 1.391(2) . ?
C14 H14 0.9300 . ?
C14 C13 1.386(2) . ?
C15 C16 1.386(2) . ?
C15 C19 1.383(3) . ?
C20 C17 1.509(2) . ?
C4 C5 1.392(3) . ?
C17 C16 1.384(2) . ?
C12 C11 1.385(3) . ?
C12 C13 1.386(2) . ?
C16 H16 0.9300 . ?
C10 H10 0.9300 . ?
C10 C11 1.384(2) . ?
C10 F5 1.418(5) . ?
C2 C7 1.390(3) . ?
C2 C1 1.507(2) . ?
C11 H11 0.9300 . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C25 C24 1.514(3) . ?
C13 H13 0.9300 . ?
C7 C6 1.380(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.382(2) . ?
C19 H19 0.9300 . ?
C19 C18 1.389(3) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 C24 1.514(2) . ?
C6 H6 0.9300 . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C18 H18 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C22 O5 H5A 109.5 . . ?
C26 O7 H7 109.5 . . ?
C15 O2 C12 119.09(13) . . ?
C18 N3 C17 117.09(14) . . ?
C20 N4 H4 118.9 . . ?
C20 N4 C21 122.11(15) . . ?
C21 N4 H4 118.9 . . ?
C8 N1 H1 116.8 . . ?
C8 N1 C4 126.33(15) . . ?
C4 N1 H1 116.8 . . ?
C8 N2 H2 118.7 . . ?
C8 N2 C9 122.59(15) . . ?
C9 N2 H2 118.7 . . ?
O1 C8 N1 124.68(15) . . ?
O1 C8 N2 123.61(15) . . ?
N2 C8 N1 111.71(15) . . ?
O5 C22 C23 114.17(14) . . ?
O4 C22 O5 122.25(17) . . ?
O4 C22 C23 123.57(16) . . ?
O7 C26 C25 115.60(15) . . ?
O6 C26 O7 123.31(16) . . ?
O6 C26 C25 121.09(15) . . ?
C14 C9 N2 122.24(15) . . ?
C10 C9 N2 120.35(15) . . ?
C10 C9 C14 117.26(14) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 121.02(16) . . ?
F4 C14 C9 119.63(15) . . ?
F4 C14 C13 117.33(15) . . ?
C9 C14 H14 118.5 . . ?
C13 C14 C9 122.96(15) . . ?
C13 C14 H14 118.5 . . ?
O2 C15 C16 116.45(15) . . ?
O2 C15 C19 123.98(15) . . ?
C19 C15 C16 119.49(15) . . ?
O3 C20 N4 123.38(15) . . ?
O3 C20 C17 119.51(15) . . ?
N4 C20 C17 117.10(15) . . ?
C3 C4 N1 117.28(15) . . ?
C5 C4 N1 123.46(15) . . ?
C5 C4 C3 119.25(15) . . ?
N3 C17 C20 119.20(14) . . ?
N3 C17 C16 122.86(15) . . ?
C16 C17 C20 117.94(15) . . ?
C11 C12 O2 120.71(15) . . ?
C11 C12 C13 122.21(15) . . ?
C13 C12 O2 116.85(16) . . ?
C15 C16 H16 120.6 . . ?
C17 C16 C15 118.77(16) . . ?
C17 C16 H16 120.6 . . ?
C9 C10 H10 119.1 . . ?
C9 C10 F5 117.3(2) . . ?
C11 C10 C9 121.83(16) . . ?
C11 C10 H10 119.1 . . ?
C11 C10 F5 120.7(2) . . ?
C3 C2 C1 119.43(16) . . ?
C7 C2 C3 118.86(16) . . ?
C7 C2 C1 121.67(15) . . ?
C12 C11 H11 120.8 . . ?
C10 C11 C12 118.47(15) . . ?
C10 C11 H11 120.8 . . ?
C26 C25 H25A 108.9 . . ?
C26 C25 H25B 108.9 . . ?
C26 C25 C24 113.46(14) . . ?
H25A C25 H25B 107.7 . . ?
C24 C25 H25A 108.9 . . ?
C24 C25 H25B 108.9 . . ?
C14 C13 C12 117.24(16) . . ?
C14 C13 H13 121.4 . . ?
C12 C13 H13 121.4 . . ?
C2 C7 Cl1 121.86(13) . . ?
C6 C7 Cl1 118.01(14) . . ?
C6 C7 C2 120.13(15) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 C4 119.44(16) . . ?
C6 C5 H5 120.3 . . ?
C15 C19 H19 121.2 . . ?
C15 C19 C18 117.52(15) . . ?
C18 C19 H19 121.2 . . ?
F1 C1 F2 106.16(13) . . ?
F1 C1 C2 113.21(15) . . ?
F3 C1 F1 106.91(14) . . ?
F3 C1 F2 106.58(15) . . ?
F3 C1 C2 112.23(14) . . ?
F2 C1 C2 111.30(14) . . ?
C22 C23 H23A 108.3 . . ?
C22 C23 H23B 108.3 . . ?
C22 C23 C24 116.14(15) . . ?
H23A C23 H23B 107.4 . . ?
C24 C23 H23A 108.3 . . ?
C24 C23 H23B 108.3 . . ?
C7 C6 C5 121.26(17) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C25 C24 C23 111.12(15) . . ?
C25 C24 H24A 109.4 . . ?
C25 C24 H24B 109.4 . . ?
C23 C24 H24A 109.4 . . ?
C23 C24 H24B 109.4 . . ?
H24A C24 H24B 108.0 . . ?
N3 C18 C19 124.23(17) . . ?
N3 C18 H18 117.9 . . ?
C19 C18 H18 117.9 . . ?
N4 C21 H21A 109.5 . . ?
N4 C21 H21B 109.5 . . ?
N4 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

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
O5 H5A N3 0.82 1.92 2.7197(19) 164.8 .
O7 H7 O6 0.82 1.79 2.5850(17) 163.3 3_777
N4 H4 O4 0.86 2.08 2.890(2) 156.8 .
N1 H1 O3 0.86 2.19 2.9674(19) 149.8 3_666

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 C7 C6 C5 -177.87(13) . . . . ?
O3 C20 C17 N3 -156.75(15) . . . . ?
O3 C20 C17 C16 23.0(2) . . . . ?
O5 C22 C23 C24 -30.9(2) . . . . ?
O7 C26 C25 C24 153.16(15) . . . . ?
O6 C26 C25 C24 -27.4(2) . . . . ?
O2 C15 C16 C17 -175.74(15) . . . . ?
O2 C15 C19 C18 174.85(16) . . . . ?
O2 C12 C11 C10 173.60(16) . . . . ?
O2 C12 C13 C14 -173.14(15) . . . . ?
F4 C14 C13 C12 176.37(16) . . . . ?
O4 C22 C23 C24 150.02(18) . . . . ?
N3 C17 C16 C15 0.6(2) . . . . ?
N4 C20 C17 N3 24.7(2) . . . . ?
N4 C20 C17 C16 -155.57(15) . . . . ?
N1 C4 C5 C6 177.01(16) . . . . ?
N2 C9 C14 F4 -2.4(3) . . . . ?
N2 C9 C14 C13 174.23(16) . . . . ?
N2 C9 C10 C11 -173.61(16) . . . . ?
N2 C9 C10 F5 1.3(3) . . . . ?
C8 N1 C4 C3 -164.96(16) . . . . ?
C8 N1 C4 C5 16.4(3) . . . . ?
C8 N2 C9 C14 58.5(2) . . . . ?
C8 N2 C9 C10 -126.01(18) . . . . ?
C22 C23 C24 C25 177.17(15) . . . . ?
C26 C25 C24 C23 -177.25(15) . . . . ?
C9 N2 C8 O1 10.3(3) . . . . ?
C9 N2 C8 N1 -169.98(15) . . . . ?
C9 C14 C13 C12 -0.4(3) . . . . ?
C9 C10 C11 C12 -1.0(3) . . . . ?
C3 C4 C5 C6 -1.6(2) . . . . ?
C3 C2 C7 Cl1 177.14(12) . . . . ?
C3 C2 C7 C6 -2.2(2) . . . . ?
C3 C2 C1 F1 -125.19(16) . . . . ?
C3 C2 C1 F3 -4.0(2) . . . . ?
C3 C2 C1 F2 115.32(17) . . . . ?
C14 C9 C10 C11 2.1(3) . . . . ?
C14 C9 C10 F5 177.0(3) . . . . ?
C15 O2 C12 C11 50.7(2) . . . . ?
C15 O2 C12 C13 -134.56(17) . . . . ?
C15 C19 C18 N3 0.7(3) . . . . ?
C20 C17 C16 C15 -179.13(14) . . . . ?
C4 N1 C8 O1 5.8(3) . . . . ?
C4 N1 C8 N2 -173.94(15) . . . . ?
C4 C3 C2 C7 1.0(2) . . . . ?
C4 C3 C2 C1 -176.73(15) . . . . ?
C4 C5 C6 C7 0.5(3) . . . . ?
C17 N3 C18 C19 0.9(3) . . . . ?
C12 O2 C15 C16 -153.18(16) . . . . ?
C12 O2 C15 C19 30.2(3) . . . . ?
C16 C15 C19 C18 -1.7(3) . . . . ?
C10 C9 C14 F4 -178.02(16) . . . . ?
C10 C9 C14 C13 -1.4(3) . . . . ?
C2 C3 C4 N1 -177.82(15) . . . . ?
C2 C3 C4 C5 0.9(2) . . . . ?
C2 C7 C6 C5 1.5(3) . . . . ?
C11 C12 C13 C14 1.5(3) . . . . ?
C13 C12 C11 C10 -0.8(3) . . . . ?
C7 C2 C1 F1 57.2(2) . . . . ?
C7 C2 C1 F3 178.31(15) . . . . ?
C7 C2 C1 F2 -62.3(2) . . . . ?
C19 C15 C16 C17 1.0(2) . . . . ?
C1 C2 C7 Cl1 -5.2(2) . . . . ?
C1 C2 C7 C6 175.51(15) . . . . ?
C18 N3 C17 C20 178.19(14) . . . . ?
C18 N3 C17 C16 -1.6(2) . . . . ?
C21 N4 C20 O3 -0.8(2) . . . . ?
C21 N4 C20 C17 177.70(15) . . . . ?
F5 C10 C11 C12 -175.8(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.871
_oxdiff_exptl_absorpt_empirical_full_min 0.418
