# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1943973'
loop_
_audit_author_name
_audit_author_address
'Sevgi Kansiz'
;Ondokuz Mayis University
Turkey
;

_audit_update_record             
;
2019-09-30 deposited with the CCDC.	2020-02-09 downloaded from the CCDC.
;
_publcif_datablock.id            {6cad8f80-2974-41b2-aa93-9fb444053442}

# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H12 F18 N3 O6 Sm'
_chemical_formula_sum            'C27 H12 F18 N3 O6 Sm'
_chemical_formula_weight         966.75

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'
Sm Sm -0.1638 3.4418 '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                   14.2281(7)
_cell_length_b                   13.2389(5)
_cell_length_c                   19.1915(9)
_cell_angle_alpha                90
_cell_angle_beta                 109.357(4)
_cell_angle_gamma                90
_cell_volume                     3410.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    30927
_cell_measurement_theta_min      1.52
_cell_measurement_theta_max      30.53

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.883
_exptl_crystal_F_000             1868
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.770
_exptl_crystal_size_mid          0.573
_exptl_crystal_size_min          0.430
_exptl_absorpt_coefficient_mu    1.865
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.3529
_exptl_absorpt_correction_T_max  0.6374
_exptl_absorpt_process_details   '(X-RED32; Stoe & Cie, 2002)'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean 6.67
_diffrn_reflns_number            21818
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.906
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_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             6702
_reflns_number_gt                5371
_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       'STOE X-AREA(Stoe & Cie, 2002)'
_computing_cell_refinement       'STOE X-AREA(Stoe & Cie, 2002)'
_computing_data_reduction        'STOE X-RED(Stoe & Cie, 2002)'
_computing_structure_solution    'SHELXT-2017/1 (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2015b)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  
;
WinGX (Farrugia, 2012), SHELXL-2018/3 (Sheldrick, 2015b), 
PLATON (Spek, 2009) and publCIF (Westrip, 2010)
;
_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)+(0.0739P)²+1.2637P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6702
_refine_ls_number_parameters     496
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0426
_refine_ls_wR_factor_ref         0.1176
_refine_ls_wR_factor_gt          0.1116
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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
Sm1 Sm 0.39914(2) 0.70340(2) 0.61851(2) 0.05401(10) Uani 1 1 d . . . . .
O1 O 0.4350(3) 0.5308(3) 0.66665(18) 0.0658(8) Uani 1 1 d . . . . .
O5 O 0.2680(2) 0.8134(2) 0.5578(2) 0.0684(9) Uani 1 1 d . . . . .
O4 O 0.5660(2) 0.6970(3) 0.70478(19) 0.0642(8) Uani 1 1 d . . . . .
O3 O 0.3963(3) 0.7554(3) 0.7364(2) 0.0694(8) Uani 1 1 d . . . . .
O2 O 0.2544(3) 0.6303(3) 0.6399(2) 0.0785(10) Uani 1 1 d . . . . .
N2 N 0.4998(3) 0.6796(3) 0.5348(2) 0.0574(9) Uani 1 1 d . . . . .
O6 O 0.4634(2) 0.8687(3) 0.6191(2) 0.0694(9) Uani 1 1 d . . . . .
N3 N 0.5299(3) 0.6113(3) 0.4386(2) 0.0641(9) Uani 1 1 d . . . . .
H3 H 0.520967 0.576096 0.399294 0.077 Uiso 1 1 calc R U . . .
F10 F 0.7581(3) 0.7047(5) 0.8714(3) 0.147(2) Uani 1 1 d . . . . .
N1 N 0.3121(3) 0.6032(3) 0.4966(2) 0.0646(9) Uani 1 1 d . . . . .
F7 F 0.3334(5) 0.8366(5) 0.8380(3) 0.155(2) Uani 1 1 d . . . . .
C12 C 0.5951(4) 0.7088(3) 0.5367(3) 0.0608(11) Uani 1 1 d . . . . .
C6 C 0.4640(3) 0.6228(3) 0.4750(2) 0.0568(10) Uani 1 1 d . . . . .
C19 C 0.4580(4) 0.7610(4) 0.8002(3) 0.0677(12) Uani 1 1 d . . . . .
C7 C 0.6136(4) 0.6659(4) 0.4756(3) 0.0662(12) Uani 1 1 d . . . . .
F9 F 0.4744(5) 0.8262(6) 0.9186(3) 0.186(3) Uani 1 1 d . . . . .
C14 C 0.4099(4) 0.4931(4) 0.7179(3) 0.0694(12) Uani 1 1 d . . . . .
C26 C 0.2566(4) 0.9061(4) 0.5495(3) 0.0650(12) Uani 1 1 d . . . . .
C21 C 0.6055(4) 0.7142(4) 0.7718(3) 0.0662(12) Uani 1 1 d . . . . .
F18 F 0.5555(5) 1.0378(5) 0.6892(4) 0.196(3) Uani 1 1 d . . . . .
C5 C 0.3641(4) 0.5800(3) 0.4514(3) 0.0599(11) Uani 1 1 d . . . . .
F2 F 0.4671(6) 0.3803(5) 0.8204(3) 0.171(3) Uani 1 1 d . . . . .
F8 F 0.3876(6) 0.7006(4) 0.8847(4) 0.161(3) Uani 1 1 d . . . . .
F3 F 0.4890(6) 0.3392(4) 0.7238(3) 0.171(3) Uani 1 1 d . . . . .
C24 C 0.4283(4) 0.9533(4) 0.6011(3) 0.0683(12) Uani 1 1 d . . . . .
C11 C 0.6646(4) 0.7706(4) 0.5850(3) 0.0744(14) Uani 1 1 d . . . . .
H11 H 0.652873 0.800472 0.625225 0.089 Uiso 1 1 calc R U . . .
C20 C 0.5595(4) 0.7449(5) 0.8216(3) 0.0785(15) Uani 1 1 d . . . . .
H20 H 0.598101 0.754896 0.870728 0.094 Uiso 1 1 calc R U . . .
C8 C 0.7032(5) 0.6823(5) 0.4623(4) 0.0853(17) Uani 1 1 d . . . . .
H8 H 0.715488 0.653418 0.422044 0.102 Uiso 1 1 calc R U . . .
C16 C 0.2525(5) 0.5779(5) 0.6935(4) 0.0812(16) Uani 1 1 d . . . . .
C15 C 0.3258(5) 0.5129(5) 0.7359(4) 0.0852(16) Uani 1 1 d . . . . .
H15 H 0.317884 0.482154 0.777181 0.102 Uiso 1 1 calc R U . . .
C9 C 0.7714(5) 0.7422(5) 0.5108(4) 0.0894(18) Uani 1 1 d . . . . .
H9 H 0.832077 0.754226 0.503727 0.107 Uiso 1 1 calc R U . . .
C25 C 0.3287(4) 0.9794(4) 0.5683(3) 0.0782(15) Uani 1 1 d . . . . .
H25 H 0.310885 1.046874 0.559048 0.094 Uiso 1 1 calc R U . . .
C4 C 0.3248(4) 0.5225(4) 0.3890(3) 0.0767(14) Uani 1 1 d . . . . .
H4 H 0.362970 0.506237 0.359497 0.092 Uiso 1 1 calc R U . . .
C1 C 0.2181(4) 0.5697(5) 0.4770(3) 0.0822(15) Uani 1 1 d . . . . .
H1 H 0.180583 0.585266 0.507112 0.099 Uiso 1 1 calc R U . . .
F17 F 0.5696(6) 1.0289(6) 0.5912(5) 0.222(4) Uani 1 1 d . . . . .
F11 F 0.7379(4) 0.6077(6) 0.7816(4) 0.207(4) Uani 1 1 d . . . . .
C18 C 0.4112(6) 0.7837(6) 0.8592(4) 0.0911(19) Uani 1 1 d . . . . .
C2 C 0.1745(5) 0.5131(6) 0.4144(4) 0.098(2) Uani 1 1 d . . . . .
H2 H 0.108839 0.491636 0.402267 0.118 Uiso 1 1 calc R U . . .
F6 F 0.0798(4) 0.5895(10) 0.6555(5) 0.252(6) Uani 1 1 d . . . . .
C13 C 0.4824(6) 0.4147(5) 0.7631(4) 0.0935(18) Uani 1 1 d . . . . .
F5 F 0.1407(6) 0.5148(6) 0.7514(5) 0.208(3) Uani 1 1 d . . . . .
C23 C 0.5052(5) 1.0374(5) 0.6213(5) 0.099(2) Uani 1 1 d . . . . .
F1 F 0.5724(5) 0.4501(6) 0.7881(5) 0.217(4) Uani 1 1 d . . . . .
F12 F 0.7635(4) 0.7580(8) 0.7735(4) 0.204(4) Uani 1 1 d . . . . .
C3 C 0.2289(5) 0.4895(5) 0.3710(4) 0.0932(19) Uani 1 1 d . . . . .
H3A H 0.200963 0.450750 0.328717 0.112 Uiso 1 1 calc R U . . .
C10 C 0.7528(5) 0.7862(5) 0.5707(4) 0.0893(18) Uani 1 1 d . . . . .
H10 H 0.801301 0.827421 0.602311 0.107 Uiso 1 1 calc R U . . .
F16 F 0.4714(4) 1.1266(4) 0.6094(6) 0.233(5) Uani 1 1 d . . . . .
C22 C 0.7176(5) 0.6953(7) 0.8017(4) 0.104(2) Uani 1 1 d . . . . .
F4 F 0.1568(7) 0.6679(7) 0.7470(8) 0.271(6) Uani 1 1 d . . . . .
C17 C 0.1552(9) 0.5881(7) 0.7107(7) 0.134(4) Uani 1 1 d . . . . .
F15 F 0.1288(4) 1.0198(6) 0.5360(7) 0.292(7) Uani 1 1 d . . . . .
F14 F 0.1219(6) 0.9501(11) 0.4517(4) 0.276(6) Uani 1 1 d . . . . .
C27 C 0.1498(4) 0.9410(5) 0.5171(4) 0.0866(17) Uani 1 1 d . . . . .
F13 F 0.0885(4) 0.8810(6) 0.5224(7) 0.263(6) 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
Sm1 O5 2.349(3) . ?
Sm1 O6 2.370(3) . ?
Sm1 O3 2.379(4) . ?
Sm1 O4 2.404(3) . ?
Sm1 O2 2.430(4) . ?
Sm1 O1 2.454(3) . ?
Sm1 N2 2.501(4) . ?
Sm1 N1 2.616(4) . ?
O1 C14 1.256(6) . ?
O5 C26 1.241(6) . ?
O4 C21 1.242(6) . ?
O3 C19 1.250(6) . ?
O2 C16 1.249(7) . ?
N2 C6 1.325(6) . ?
N2 C12 1.400(6) . ?
O6 C24 1.229(6) . ?
N3 C6 1.351(6) . ?
N3 C7 1.373(7) . ?
N3 H3 0.8600 . ?
F10 C22 1.275(8) . ?
N1 C1 1.340(7) . ?
N1 C5 1.349(6) . ?
F7 C18 1.257(8) . ?
C12 C11 1.379(7) . ?
C12 C7 1.403(7) . ?
C6 C5 1.456(7) . ?
C19 C20 1.381(8) . ?
C19 C18 1.522(8) . ?
C7 C8 1.397(8) . ?
F9 C18 1.321(9) . ?
C14 C15 1.377(8) . ?
C14 C13 1.517(9) . ?
C26 C25 1.370(7) . ?
C26 C27 1.512(7) . ?
C21 C20 1.386(7) . ?
C21 C22 1.527(8) . ?
F18 C23 1.261(9) . ?
C5 C4 1.372(7) . ?
F2 C13 1.274(8) . ?
F8 C18 1.292(8) . ?
F3 C13 1.275(9) . ?
C24 C25 1.389(7) . ?
C24 C23 1.519(8) . ?
C11 C10 1.386(8) . ?
C11 H11 0.9300 . ?
C20 H20 0.9300 . ?
C8 C9 1.355(10) . ?
C8 H8 0.9300 . ?
C16 C15 1.388(9) . ?
C16 C17 1.531(9) . ?
C15 H15 0.9300 . ?
C9 C10 1.390(9) . ?
C9 H9 0.9300 . ?
C25 H25 0.9300 . ?
C4 C3 1.364(9) . ?
C4 H4 0.9300 . ?
C1 C2 1.377(9) . ?
C1 H1 0.9300 . ?
F17 C23 1.240(10) . ?
F11 C22 1.284(9) . ?
C2 C3 1.348(10) . ?
C2 H2 0.9300 . ?
F6 C17 1.233(14) . ?
C13 F1 1.296(9) . ?
F5 C17 1.305(11) . ?
C23 F16 1.267(9) . ?
F12 C22 1.280(11) . ?
C3 H3A 0.9300 . ?
C10 H10 0.9300 . ?
F4 C17 1.262(11) . ?
F15 C27 1.175(8) . ?
F14 C27 1.190(10) . ?
C27 F13 1.209(9) . ?

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
O5 Sm1 O6 70.82(12) . . ?
O5 Sm1 O3 91.80(13) . . ?
O6 Sm1 O3 81.73(13) . . ?
O5 Sm1 O4 143.53(12) . . ?
O6 Sm1 O4 74.81(12) . . ?
O3 Sm1 O4 71.30(11) . . ?
O5 Sm1 O2 75.68(13) . . ?
O6 Sm1 O2 135.55(12) . . ?
O3 Sm1 O2 70.85(13) . . ?
O4 Sm1 O2 124.64(13) . . ?
O5 Sm1 O1 142.75(12) . . ?
O6 Sm1 O1 145.69(12) . . ?
O3 Sm1 O1 88.75(12) . . ?
O4 Sm1 O1 70.91(12) . . ?
O2 Sm1 O1 69.38(12) . . ?
O5 Sm1 N2 106.82(13) . . ?
O6 Sm1 N2 79.50(13) . . ?
O3 Sm1 N2 147.30(13) . . ?
O4 Sm1 N2 78.04(12) . . ?
O2 Sm1 N2 139.09(13) . . ?
O1 Sm1 N2 91.85(12) . . ?
O5 Sm1 N1 78.94(12) . . ?
O6 Sm1 N1 122.67(13) . . ?
O3 Sm1 N1 147.70(13) . . ?
O4 Sm1 N1 131.64(11) . . ?
O2 Sm1 N1 76.87(13) . . ?
O1 Sm1 N1 80.94(12) . . ?
N2 Sm1 N1 64.13(12) . . ?
C14 O1 Sm1 125.9(3) . . ?
C26 O5 Sm1 136.5(3) . . ?
C21 O4 Sm1 135.3(3) . . ?
C19 O3 Sm1 136.1(3) . . ?
C16 O2 Sm1 127.7(4) . . ?
C6 N2 C12 105.6(4) . . ?
C6 N2 Sm1 119.4(3) . . ?
C12 N2 Sm1 134.9(3) . . ?
C24 O6 Sm1 136.1(3) . . ?
C6 N3 C7 107.8(4) . . ?
C6 N3 H3 126.1 . . ?
C7 N3 H3 126.1 . . ?
C1 N1 C5 117.0(5) . . ?
C1 N1 Sm1 123.4(4) . . ?
C5 N1 Sm1 119.5(3) . . ?
C11 C12 N2 130.8(5) . . ?
C11 C12 C7 120.7(5) . . ?
N2 C12 C7 108.4(4) . . ?
N2 C6 N3 112.3(4) . . ?
N2 C6 C5 123.1(4) . . ?
N3 C6 C5 124.7(4) . . ?
O3 C19 C20 127.4(5) . . ?
O3 C19 C18 113.7(5) . . ?
C20 C19 C18 118.8(6) . . ?
N3 C7 C8 132.5(5) . . ?
N3 C7 C12 105.9(4) . . ?
C8 C7 C12 121.6(5) . . ?
O1 C14 C15 128.2(5) . . ?
O1 C14 C13 113.8(5) . . ?
C15 C14 C13 118.0(5) . . ?
O5 C26 C25 127.7(5) . . ?
O5 C26 C27 115.2(5) . . ?
C25 C26 C27 117.1(5) . . ?
O4 C21 C20 127.8(5) . . ?
O4 C21 C22 114.6(5) . . ?
C20 C21 C22 117.5(5) . . ?
N1 C5 C4 122.5(5) . . ?
N1 C5 C6 113.4(4) . . ?
C4 C5 C6 124.1(5) . . ?
O6 C24 C25 127.7(5) . . ?
O6 C24 C23 113.9(5) . . ?
C25 C24 C23 118.3(5) . . ?
C12 C11 C10 116.7(5) . . ?
C12 C11 H11 121.7 . . ?
C10 C11 H11 121.7 . . ?
C19 C20 C21 121.8(5) . . ?
C19 C20 H20 119.1 . . ?
C21 C20 H20 119.1 . . ?
C9 C8 C7 117.1(6) . . ?
C9 C8 H8 121.4 . . ?
C7 C8 H8 121.4 . . ?
O2 C16 C15 127.6(5) . . ?
O2 C16 C17 113.3(7) . . ?
C15 C16 C17 119.1(7) . . ?
C14 C15 C16 121.2(5) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C8 C9 C10 121.5(6) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 H9 119.3 . . ?
C26 C25 C24 120.4(5) . . ?
C26 C25 H25 119.8 . . ?
C24 C25 H25 119.8 . . ?
C3 C4 C5 118.9(6) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
N1 C1 C2 122.9(6) . . ?
N1 C1 H1 118.5 . . ?
C2 C1 H1 118.5 . . ?
F7 C18 F8 106.6(7) . . ?
F7 C18 F9 108.5(7) . . ?
F8 C18 F9 103.0(7) . . ?
F7 C18 C19 115.0(6) . . ?
F8 C18 C19 110.3(6) . . ?
F9 C18 C19 112.6(6) . . ?
C3 C2 C1 118.8(6) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
F2 C13 F3 107.3(6) . . ?
F2 C13 F1 103.9(7) . . ?
F3 C13 F1 104.2(8) . . ?
F2 C13 C14 117.4(7) . . ?
F3 C13 C14 111.6(6) . . ?
F1 C13 C14 111.4(6) . . ?
F17 C23 F18 103.2(7) . . ?
F17 C23 F16 107.2(8) . . ?
F18 C23 F16 103.5(8) . . ?
F17 C23 C24 113.3(7) . . ?
F18 C23 C24 112.4(6) . . ?
F16 C23 C24 116.0(6) . . ?
C2 C3 C4 120.0(6) . . ?
C2 C3 H3A 120.0 . . ?
C4 C3 H3A 120.0 . . ?
C11 C10 C9 122.4(6) . . ?
C11 C10 H10 118.8 . . ?
C9 C10 H10 118.8 . . ?
F10 C22 F12 105.3(7) . . ?
F10 C22 F11 109.5(8) . . ?
F12 C22 F11 105.2(8) . . ?
F10 C22 C21 115.5(6) . . ?
F12 C22 C21 110.5(7) . . ?
F11 C22 C21 110.2(6) . . ?
F6 C17 F4 108.3(11) . . ?
F6 C17 F5 105.0(10) . . ?
F4 C17 F5 105.6(10) . . ?
F6 C17 C16 114.1(9) . . ?
F4 C17 C16 110.0(8) . . ?
F5 C17 C16 113.4(8) . . ?
F15 C27 F14 101.9(9) . . ?
F15 C27 F13 107.1(9) . . ?
F14 C27 F13 99.1(9) . . ?
F15 C27 C26 117.9(6) . . ?
F14 C27 C26 113.7(7) . . ?
F13 C27 C26 114.8(6) . . ?

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 N2 C12 C11 177.5(5) . . . . ?
Sm1 N2 C12 C11 -6.5(8) . . . . ?
C6 N2 C12 C7 -0.5(5) . . . . ?
Sm1 N2 C12 C7 175.5(3) . . . . ?
C12 N2 C6 N3 1.3(5) . . . . ?
Sm1 N2 C6 N3 -175.5(3) . . . . ?
C12 N2 C6 C5 -177.7(4) . . . . ?
Sm1 N2 C6 C5 5.6(6) . . . . ?
C7 N3 C6 N2 -1.6(5) . . . . ?
C7 N3 C6 C5 177.3(4) . . . . ?
Sm1 O3 C19 C20 6.9(10) . . . . ?
Sm1 O3 C19 C18 -170.1(4) . . . . ?
C6 N3 C7 C8 -178.8(6) . . . . ?
C6 N3 C7 C12 1.2(5) . . . . ?
C11 C12 C7 N3 -178.7(5) . . . . ?
N2 C12 C7 N3 -0.4(5) . . . . ?
C11 C12 C7 C8 1.3(8) . . . . ?
N2 C12 C7 C8 179.6(5) . . . . ?
Sm1 O1 C14 C15 32.8(8) . . . . ?
Sm1 O1 C14 C13 -148.7(4) . . . . ?
Sm1 O5 C26 C25 9.5(9) . . . . ?
Sm1 O5 C26 C27 -168.2(4) . . . . ?
Sm1 O4 C21 C20 0.4(9) . . . . ?
Sm1 O4 C21 C22 178.3(5) . . . . ?
C1 N1 C5 C4 -1.7(7) . . . . ?
Sm1 N1 C5 C4 175.9(4) . . . . ?
C1 N1 C5 C6 177.6(5) . . . . ?
Sm1 N1 C5 C6 -4.7(5) . . . . ?
N2 C6 C5 N1 -0.5(6) . . . . ?
N3 C6 C5 N1 -179.2(4) . . . . ?
N2 C6 C5 C4 178.9(5) . . . . ?
N3 C6 C5 C4 0.1(7) . . . . ?
Sm1 O6 C24 C25 -3.3(10) . . . . ?
Sm1 O6 C24 C23 173.8(5) . . . . ?
N2 C12 C11 C10 -178.9(5) . . . . ?
C7 C12 C11 C10 -1.1(8) . . . . ?
O3 C19 C20 C21 -3.3(10) . . . . ?
C18 C19 C20 C21 173.5(6) . . . . ?
O4 C21 C20 C19 -0.3(10) . . . . ?
C22 C21 C20 C19 -178.1(6) . . . . ?
N3 C7 C8 C9 179.5(6) . . . . ?
C12 C7 C8 C9 -0.5(9) . . . . ?
Sm1 O2 C16 C15 -30.3(9) . . . . ?
Sm1 O2 C16 C17 151.0(6) . . . . ?
O1 C14 C15 C16 3.5(10) . . . . ?
C13 C14 C15 C16 -175.0(6) . . . . ?
O2 C16 C15 C14 -5.4(10) . . . . ?
C17 C16 C15 C14 173.2(7) . . . . ?
C7 C8 C9 C10 -0.5(10) . . . . ?
O5 C26 C25 C24 -0.3(10) . . . . ?
C27 C26 C25 C24 177.4(6) . . . . ?
O6 C24 C25 C26 -2.7(10) . . . . ?
C23 C24 C25 C26 -179.6(6) . . . . ?
N1 C5 C4 C3 1.7(8) . . . . ?
C6 C5 C4 C3 -177.6(5) . . . . ?
C5 N1 C1 C2 0.6(9) . . . . ?
Sm1 N1 C1 C2 -177.0(5) . . . . ?
O3 C19 C18 F7 -31.0(9) . . . . ?
C20 C19 C18 F7 151.7(7) . . . . ?
O3 C19 C18 F8 89.6(8) . . . . ?
C20 C19 C18 F8 -87.7(9) . . . . ?
O3 C19 C18 F9 -156.0(7) . . . . ?
C20 C19 C18 F9 26.7(9) . . . . ?
N1 C1 C2 C3 0.6(11) . . . . ?
O1 C14 C13 F2 173.4(7) . . . . ?
C15 C14 C13 F2 -8.0(10) . . . . ?
O1 C14 C13 F3 -62.2(8) . . . . ?
C15 C14 C13 F3 116.5(7) . . . . ?
O1 C14 C13 F1 53.7(9) . . . . ?
C15 C14 C13 F1 -127.6(8) . . . . ?
O6 C24 C23 F17 61.1(10) . . . . ?
C25 C24 C23 F17 -121.6(9) . . . . ?
O6 C24 C23 F18 -55.4(10) . . . . ?
C25 C24 C23 F18 121.9(8) . . . . ?
O6 C24 C23 F16 -174.2(8) . . . . ?
C25 C24 C23 F16 3.1(12) . . . . ?
C1 C2 C3 C4 -0.7(11) . . . . ?
C5 C4 C3 C2 -0.4(10) . . . . ?
C12 C11 C10 C9 0.1(10) . . . . ?
C8 C9 C10 C11 0.7(11) . . . . ?
O4 C21 C22 F10 -174.6(7) . . . . ?
C20 C21 C22 F10 3.5(11) . . . . ?
O4 C21 C22 F12 66.0(9) . . . . ?
C20 C21 C22 F12 -115.8(8) . . . . ?
O4 C21 C22 F11 -49.8(10) . . . . ?
C20 C21 C22 F11 128.3(8) . . . . ?
O2 C16 C17 F6 41.6(12) . . . . ?
C15 C16 C17 F6 -137.1(10) . . . . ?
O2 C16 C17 F4 -80.2(13) . . . . ?
C15 C16 C17 F4 101.0(11) . . . . ?
O2 C16 C17 F5 161.8(9) . . . . ?
C15 C16 C17 F5 -16.9(13) . . . . ?
O5 C26 C27 F15 147.5(10) . . . . ?
C25 C26 C27 F15 -30.4(13) . . . . ?
O5 C26 C27 F14 -93.4(11) . . . . ?
C25 C26 C27 F14 88.7(11) . . . . ?
O5 C26 C27 F13 19.9(12) . . . . ?
C25 C26 C27 F13 -158.1(10) . . . . ?

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
_geom_hbond_publ_flag
N3 H3 O1 0.86 2.13 2.922(5) 153.7 3_666 yes
N3 H3 F3 0.86 2.58 3.109(6) 121.1 3_666 yes
C11 H11 O4 0.93 2.64 3.215(6) 120.4 . yes
C1 H1 O2 0.93 2.49 3.100(8) 123.7 . yes

_refine_diff_density_max         0.942
_refine_diff_density_min         -1.142
_refine_diff_density_rms         0.103


loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?



_publcif_funding_html            
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