# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1993746'
loop_
_audit_author_name
_audit_author_address
'Eleni Moushi'
;European University Cyprus
Cyprus
;
_audit_update_record             
;
2020-04-05 deposited with the CCDC.	2020-06-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C46 H44 F2 N6 O6 Sn'
_chemical_formula_sum            'C46 H44 F2 N6 O6 Sn'
_chemical_formula_weight         933.56

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'
Sn Sn 0.0259 5.4591 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 2/a'
_space_group_name_Hall           '-I 2ya'

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

_cell_length_a                   14.7410(6)
_cell_length_b                   20.2602(5)
_cell_length_c                   18.8558(7)
_cell_angle_alpha                90
_cell_angle_beta                 111.400(4)
_cell_angle_gamma                90
_cell_volume                     5243.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3509
_cell_measurement_theta_min      7.2160
_cell_measurement_theta_max      71.7220

_exptl_crystal_description       Rod
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.183
_exptl_crystal_F_000             1912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.015
_exptl_crystal_size_min          0.01
_exptl_absorpt_coefficient_mu    4.320
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.89732
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.674
_oxdiff_exptl_absorpt_empirical_full_max 1.427
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4223
_diffrn_reflns_number            10180
_diffrn_reflns_av_unetI/netI     0.0701
_diffrn_reflns_av_R_equivalents  0.0516
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.890
_diffrn_reflns_theta_max         66.983
_diffrn_reflns_theta_full        66.983
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4682
_reflns_number_gt                3818
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0827P)²] 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         4682
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0654
_refine_ls_R_factor_gt           0.0523
_refine_ls_wR_factor_ref         0.1428
_refine_ls_wR_factor_gt          0.1361
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_restrained_S_all      0.992
_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
C1 C 0.7087(3) 0.4333(2) 0.5957(2) 0.0314(8) Uani 1 1 d . . . . .
C2 C 0.6553(3) 0.43021(19) 0.5160(2) 0.0315(8) Uani 1 1 d . . . . .
C3 C 0.6084(3) 0.4895(2) 0.4791(2) 0.0319(8) Uani 1 1 d . . . . .
C4 C 0.6232(3) 0.5500(2) 0.5187(2) 0.0313(8) Uani 1 1 d . . . . .
C5 C 0.7182(3) 0.4941(2) 0.6314(2) 0.0332(8) Uani 1 1 d . . . . .
H5 H 0.7529 0.4958 0.6836 0.040 Uiso 1 1 calc R U . . .
C6 C 0.7509(3) 0.3752(2) 0.6445(2) 0.0369(9) Uani 1 1 d . . . . .
C7 C 0.5459(3) 0.4886(2) 0.4025(2) 0.0367(9) Uani 1 1 d . . . . .
H7 H 0.5353 0.4495 0.3748 0.044 Uiso 1 1 calc R U . . .
C8 C 0.5009(3) 0.5450(2) 0.3689(2) 0.0367(9) Uani 1 1 d . . . . .
C9 C 0.5202(3) 0.6074(2) 0.4041(2) 0.0366(9) Uani 1 1 d . . . . .
C10 C 0.5810(3) 0.6083(2) 0.4809(2) 0.0348(9) Uani 1 1 d . . . . .
H10 H 0.5937 0.6481 0.5073 0.042 Uiso 1 1 calc R U . . .
C11 C 0.4732(4) 0.6726(3) 0.2870(3) 0.0505(12) Uani 1 1 d . . . . .
H11A H 0.4618 0.6303 0.2611 0.061 Uiso 1 1 calc R U . . .
H11B H 0.5351 0.6897 0.2879 0.061 Uiso 1 1 calc R U . . .
C12 C 0.3916(4) 0.7204(3) 0.2449(3) 0.0579(14) Uani 1 1 d . . . . .
H12A H 0.3874 0.7253 0.1926 0.069 Uiso 1 1 calc R U . . .
H12B H 0.3298 0.7036 0.2444 0.069 Uiso 1 1 calc R U . . .
C13 C 0.4198(4) 0.7790(3) 0.3642(3) 0.0561(14) Uani 1 1 d . . . . .
H13A H 0.3569 0.7665 0.3653 0.067 Uiso 1 1 calc R U . . .
H13B H 0.4376 0.8213 0.3896 0.067 Uiso 1 1 calc R U . . .
C14 C 0.4959(4) 0.7272(2) 0.4068(3) 0.0472(11) Uani 1 1 d . . . . .
H14A H 0.5604 0.7428 0.4126 0.057 Uiso 1 1 calc R U . . .
H14B H 0.4942 0.7205 0.4573 0.057 Uiso 1 1 calc R U . . .
C15 C 0.6940(3) 0.6115(2) 0.6399(3) 0.0380(9) Uani 1 1 d . . . . .
H15 H 0.6365 0.6272 0.6494 0.046 Uiso 1 1 calc R U . . .
C16 C 0.7585(4) 0.6638(2) 0.6285(3) 0.0466(11) Uani 1 1 d . . . . .
H16A H 0.7399 0.7094 0.6304 0.056 Uiso 1 1 calc R U . . .
H16B H 0.7912 0.6547 0.5932 0.056 Uiso 1 1 calc R U . . .
C17 C 0.7886(4) 0.6245(2) 0.7007(3) 0.0479(11) Uani 1 1 d . . . . .
H17A H 0.8397 0.5919 0.7091 0.057 Uiso 1 1 calc R U . . .
H17B H 0.7884 0.6466 0.7463 0.057 Uiso 1 1 calc R U . . .
C18 C 0.6258(4) 0.2351(2) 0.4603(3) 0.0438(11) Uani 1 1 d . . . . .
C19 C 0.6266(5) 0.1705(3) 0.4852(4) 0.0708(18) Uani 1 1 d . . . . .
H19 H 0.6834 0.1536 0.5214 0.085 Uiso 1 1 calc R U . . .
C20 C 0.5429(6) 0.1297(3) 0.4567(5) 0.102(3) Uani 1 1 d . . . . .
H20 H 0.5445 0.0868 0.4746 0.123 Uiso 1 1 calc R U . . .
C21 C 0.4594(6) 0.1541(4) 0.4024(5) 0.090(2) Uani 1 1 d . . . . .
H21 H 0.4050 0.1270 0.3831 0.108 Uiso 1 1 calc R U . . .
C22 C 0.4544(4) 0.2182(3) 0.3757(3) 0.0611(14) Uani 1 1 d . . . . .
H22 H 0.3973 0.2345 0.3394 0.073 Uiso 1 1 calc R U . . .
C23 C 0.5367(4) 0.2573(3) 0.4046(3) 0.0488(11) Uani 1 1 d . . . . .
H23 H 0.5337 0.3004 0.3868 0.059 Uiso 1 1 calc R U . . .
N1 N 0.6813(2) 0.55015(16) 0.59601(18) 0.0308(7) Uani 1 1 d . . . . .
N2 N 0.4765(3) 0.66405(19) 0.3650(2) 0.0433(9) Uani 1 1 d . . . . .
N3 N 0.4128(4) 0.7852(2) 0.2842(3) 0.0618(13) Uani 1 1 d . . . . .
O1 O 0.7557(2) 0.31939(14) 0.61224(16) 0.0362(6) Uani 1 1 d . . . . .
O2 O 0.7792(3) 0.38053(17) 0.71343(18) 0.0572(10) Uani 1 1 d . . . . .
O3 O 0.6481(2) 0.37818(13) 0.47540(16) 0.0351(6) Uani 1 1 d . . . . .
F1 F 0.43125(19) 0.53985(14) 0.29827(14) 0.0471(6) Uani 1 1 d . . . . .
Sn1 Sn 0.7500 0.29715(2) 0.5000 0.03699(15) Uani 1 2 d S T P . .
H3 H 0.472(5) 0.804(3) 0.281(3) 0.058(17) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C5 1.386(6) . ?
C1 C2 1.420(5) . ?
C1 C6 1.485(6) . ?
C2 O3 1.284(5) . ?
C2 C3 1.434(6) . ?
C3 C7 1.401(6) . ?
C3 C4 1.410(6) . ?
C4 N1 1.396(5) . ?
C4 C10 1.403(6) . ?
C5 N1 1.328(5) . ?
C5 H5 0.9300 . ?
C6 O2 1.216(5) . ?
C6 O1 1.299(5) . ?
C7 C8 1.357(6) . ?
C7 H7 0.9300 . ?
C8 F1 1.357(5) . ?
C8 C9 1.408(6) . ?
C9 N2 1.388(5) . ?
C9 C10 1.397(6) . ?
C10 H10 0.9300 . ?
C11 N2 1.464(6) . ?
C11 C12 1.524(6) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 N3 1.484(8) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 N3 1.480(7) . ?
C13 C14 1.532(6) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 N2 1.474(6) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 N1 1.468(5) . ?
C15 C17 1.470(6) . ?
C15 C16 1.490(6) . ?
C15 H15 0.9800 . ?
C16 C17 1.497(7) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.389(7) . ?
C18 C23 1.423(7) . ?
C18 Sn1 2.120(4) . ?
C19 C20 1.418(9) . ?
C19 H19 0.9300 . ?
C20 C21 1.375(11) . ?
C20 H20 0.9300 . ?
C21 C22 1.385(9) . ?
C21 H21 0.9300 . ?
C22 C23 1.384(7) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
N3 H3 0.97(6) . ?
O1 Sn1 2.135(3) . ?
O3 Sn1 2.158(3) . ?
Sn1 C18 2.120(4) 2_656 ?
Sn1 O1 2.135(3) 2_656 ?
Sn1 O3 2.158(3) 2_656 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 C1 C2 118.2(4) . . ?
C5 C1 C6 117.2(4) . . ?
C2 C1 C6 124.5(4) . . ?
O3 C2 C1 124.1(4) . . ?
O3 C2 C3 118.6(4) . . ?
C1 C2 C3 117.3(4) . . ?
C7 C3 C4 118.3(4) . . ?
C7 C3 C2 120.6(4) . . ?
C4 C3 C2 121.1(4) . . ?
N1 C4 C10 121.2(4) . . ?
N1 C4 C3 118.2(3) . . ?
C10 C4 C3 120.6(4) . . ?
N1 C5 C1 124.4(4) . . ?
N1 C5 H5 117.8 . . ?
C1 C5 H5 117.8 . . ?
O2 C6 O1 121.5(4) . . ?
O2 C6 C1 119.7(4) . . ?
O1 C6 C1 118.8(4) . . ?
C8 C7 C3 119.7(4) . . ?
C8 C7 H7 120.1 . . ?
C3 C7 H7 120.1 . . ?
C7 C8 F1 117.3(4) . . ?
C7 C8 C9 123.8(4) . . ?
F1 C8 C9 118.8(4) . . ?
N2 C9 C10 122.5(4) . . ?
N2 C9 C8 121.2(4) . . ?
C10 C9 C8 116.3(4) . . ?
C9 C10 C4 120.9(4) . . ?
C9 C10 H10 119.6 . . ?
C4 C10 H10 119.6 . . ?
N2 C11 C12 109.3(4) . . ?
N2 C11 H11A 109.8 . . ?
C12 C11 H11A 109.8 . . ?
N2 C11 H11B 109.8 . . ?
C12 C11 H11B 109.8 . . ?
H11A C11 H11B 108.3 . . ?
N3 C12 C11 108.7(5) . . ?
N3 C12 H12A 110.0 . . ?
C11 C12 H12A 110.0 . . ?
N3 C12 H12B 110.0 . . ?
C11 C12 H12B 110.0 . . ?
H12A C12 H12B 108.3 . . ?
N3 C13 C14 111.0(4) . . ?
N3 C13 H13A 109.4 . . ?
C14 C13 H13A 109.4 . . ?
N3 C13 H13B 109.4 . . ?
C14 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
N2 C14 C13 110.6(4) . . ?
N2 C14 H14A 109.5 . . ?
C13 C14 H14A 109.5 . . ?
N2 C14 H14B 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
N1 C15 C17 118.7(4) . . ?
N1 C15 C16 118.5(4) . . ?
C17 C15 C16 60.7(3) . . ?
N1 C15 H15 115.9 . . ?
C17 C15 H15 115.9 . . ?
C16 C15 H15 115.9 . . ?
C15 C16 C17 59.0(3) . . ?
C15 C16 H16A 117.9 . . ?
C17 C16 H16A 117.9 . . ?
C15 C16 H16B 117.9 . . ?
C17 C16 H16B 117.9 . . ?
H16A C16 H16B 115.0 . . ?
C15 C17 C16 60.3(3) . . ?
C15 C17 H17A 117.7 . . ?
C16 C17 H17A 117.7 . . ?
C15 C17 H17B 117.7 . . ?
C16 C17 H17B 117.7 . . ?
H17A C17 H17B 114.9 . . ?
C19 C18 C23 116.1(5) . . ?
C19 C18 Sn1 122.7(4) . . ?
C23 C18 Sn1 121.2(3) . . ?
C18 C19 C20 121.5(6) . . ?
C18 C19 H19 119.3 . . ?
C20 C19 H19 119.3 . . ?
C21 C20 C19 119.4(7) . . ?
C21 C20 H20 120.3 . . ?
C19 C20 H20 120.3 . . ?
C20 C21 C22 121.5(6) . . ?
C20 C21 H21 119.2 . . ?
C22 C21 H21 119.2 . . ?
C23 C22 C21 118.1(6) . . ?
C23 C22 H22 121.0 . . ?
C21 C22 H22 121.0 . . ?
C22 C23 C18 123.4(5) . . ?
C22 C23 H23 118.3 . . ?
C18 C23 H23 118.3 . . ?
C5 N1 C4 120.3(3) . . ?
C5 N1 C15 119.8(3) . . ?
C4 N1 C15 119.6(3) . . ?
C9 N2 C11 118.0(4) . . ?
C9 N2 C14 118.1(4) . . ?
C11 N2 C14 111.3(4) . . ?
C13 N3 C12 110.9(4) . . ?
C13 N3 H3 112(4) . . ?
C12 N3 H3 110(4) . . ?
C6 O1 Sn1 131.2(3) . . ?
C2 O3 Sn1 126.7(3) . . ?
C18 Sn1 C18 107.2(3) 2_656 . ?
C18 Sn1 O1 101.05(15) 2_656 2_656 ?
C18 Sn1 O1 93.37(15) . 2_656 ?
C18 Sn1 O1 93.37(15) 2_656 . ?
C18 Sn1 O1 101.05(15) . . ?
O1 Sn1 O1 155.64(15) 2_656 . ?
C18 Sn1 O3 86.10(16) 2_656 2_656 ?
C18 Sn1 O3 166.12(16) . 2_656 ?
O1 Sn1 O3 79.93(11) 2_656 2_656 ?
O1 Sn1 O3 81.60(11) . 2_656 ?
C18 Sn1 O3 166.12(16) 2_656 . ?
C18 Sn1 O3 86.10(16) . . ?
O1 Sn1 O3 81.60(11) 2_656 . ?
O1 Sn1 O3 79.93(11) . . ?
O3 Sn1 O3 80.93(16) 2_656 . ?

_refine_diff_density_max         1.238
_refine_diff_density_min         -0.954
_refine_diff_density_rms         0.091



####################################################################### 
# 
# 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_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2002394'
loop_
_audit_author_name
_audit_author_address
'Eleni Moushi'
;European University Cyprus
Cyprus
;
_audit_update_record             
;
2020-05-07 deposited with the CCDC.	2020-06-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H18 F N3 O3'
_chemical_formula_sum            'C17 H18 F N3 O3'
_chemical_formula_weight         331.34

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   7.8945(7)
_cell_length_b                   8.5010(7)
_cell_length_c                   10.7522(9)
_cell_angle_alpha                87.440(7)
_cell_angle_beta                 84.496(7)
_cell_angle_gamma                88.912(7)
_cell_volume                     717.47(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1599
_cell_measurement_theta_min      4.0850
_cell_measurement_theta_max      72.8520

_exptl_crystal_description       Polyhedral
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_F_000             348
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.967
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.78861
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.691
_oxdiff_exptl_absorpt_empirical_full_max 1.909
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4223
_diffrn_reflns_number            4189
_diffrn_reflns_av_unetI/netI     0.0582
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.134
_diffrn_reflns_theta_max         66.993
_diffrn_reflns_theta_full        66.993
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             2531
_reflns_number_gt                1996
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0632P)²+0.4091P] 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         2531
_refine_ls_number_parameters     225
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0683
_refine_ls_R_factor_gt           0.0511
_refine_ls_wR_factor_ref         0.1440
_refine_ls_wR_factor_gt          0.1345
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_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 0.7362(3) 0.2773(3) 0.7555(2) 0.0171(5) Uani 1 1 d . . . . .
C2 C 0.8040(3) 0.1989(3) 0.6437(2) 0.0166(5) Uani 1 1 d . . . . .
C3 C 0.6820(3) 0.1883(3) 0.5492(2) 0.0162(5) Uani 1 1 d . . . . .
C4 C 0.5164(3) 0.2518(3) 0.5658(2) 0.0159(5) Uani 1 1 d . . . . .
C5 C 0.5721(3) 0.3321(3) 0.7656(2) 0.0163(5) Uani 1 1 d . . . . .
H5 H 0.5330 0.3808 0.8388 0.020 Uiso 1 1 calc R U . . .
C6 C 0.7290(3) 0.1115(3) 0.4377(2) 0.0166(5) Uani 1 1 d . . . . .
H6 H 0.8363 0.0645 0.4250 0.020 Uiso 1 1 calc R U . . .
C7 C 0.6191(3) 0.1054(3) 0.3484(2) 0.0164(5) Uani 1 1 d . . . . .
C8 C 0.4546(3) 0.1762(3) 0.3591(2) 0.0166(5) Uani 1 1 d . . . . .
C9 C 0.4065(3) 0.2473(3) 0.4714(2) 0.0167(5) Uani 1 1 d . . . . .
H9 H 0.2985 0.2930 0.4840 0.020 Uiso 1 1 calc R U . . .
C10 C 0.4125(3) 0.2162(3) 0.1381(2) 0.0180(5) Uani 1 1 d . . . . .
H10A H 0.5235 0.1676 0.1185 0.022 Uiso 1 1 calc R U . . .
H10B H 0.4263 0.3295 0.1339 0.022 Uiso 1 1 calc R U . . .
C11 C 0.2938(3) 0.1713(3) 0.0433(2) 0.0196(5) Uani 1 1 d . . . . .
H11A H 0.3397 0.2066 -0.0400 0.023 Uiso 1 1 calc R U . . .
H11B H 0.2834 0.0577 0.0448 0.023 Uiso 1 1 calc R U . . .
C12 C 0.0534(3) 0.1854(3) 0.1994(2) 0.0172(5) Uani 1 1 d . . . . .
H12A H 0.0411 0.0720 0.1995 0.021 Uiso 1 1 calc R U . . .
H12B H -0.0583 0.2322 0.2199 0.021 Uiso 1 1 calc R U . . .
C13 C 0.1714(3) 0.2263(3) 0.2966(2) 0.0174(5) Uani 1 1 d . . . . .
H13A H 0.1753 0.3399 0.3014 0.021 Uiso 1 1 calc R U . . .
H13B H 0.1268 0.1830 0.3779 0.021 Uiso 1 1 calc R U . . .
C14 C 0.8359(3) 0.2985(3) 0.8664(2) 0.0175(5) Uani 1 1 d . . . . .
C15 C 0.2808(3) 0.3495(3) 0.7100(2) 0.0169(5) Uani 1 1 d . . . . .
H15 H 0.2118 0.2549 0.7265 0.020 Uiso 1 1 calc R U . . .
C16 C 0.1941(3) 0.4874(3) 0.6508(2) 0.0210(5) Uani 1 1 d . . . . .
H16A H 0.0781 0.4743 0.6310 0.025 Uiso 1 1 calc R U . . .
H16B H 0.2627 0.5562 0.5926 0.025 Uiso 1 1 calc R U . . .
C17 C 0.2257(3) 0.4869(3) 0.7870(2) 0.0204(5) Uani 1 1 d . . . . .
H17A H 0.3132 0.5553 0.8105 0.024 Uiso 1 1 calc R U . . .
H17B H 0.1286 0.4735 0.8488 0.024 Uiso 1 1 calc R U . . .
N1 N 0.4618(3) 0.3212(2) 0.67766(19) 0.0163(4) Uani 1 1 d . . . . .
N2 N 0.3438(3) 0.1642(2) 0.26578(19) 0.0171(4) Uani 1 1 d . . . . .
N3 N 0.1243(3) 0.2452(3) 0.0736(2) 0.0184(5) Uani 1 1 d D . . . .
O1 O 0.8127(2) 0.4222(2) 0.92428(17) 0.0227(4) Uani 1 1 d . . . . .
O2 O 0.9335(2) 0.1855(2) 0.89512(17) 0.0230(4) Uani 1 1 d . . . . .
O3 O 0.9525(2) 0.1495(2) 0.62332(17) 0.0206(4) Uani 1 1 d . . . . .
F1 F 0.66601(18) 0.02157(16) 0.24552(13) 0.0197(3) Uani 1 1 d . . . . .
H3A H 0.135(5) 0.353(4) 0.076(3) 0.039(10) Uiso 1 1 d . . . . .
H3B H 0.055(3) 0.225(4) 0.019(2) 0.029(8) Uiso 1 1 d D . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C5 1.364(3) . ?
C1 C2 1.453(3) . ?
C1 C14 1.509(3) . ?
C2 O3 1.240(3) . ?
C2 C3 1.472(3) . ?
C3 C4 1.403(3) . ?
C3 C6 1.406(4) . ?
C4 N1 1.391(3) . ?
C4 C9 1.400(4) . ?
C5 N1 1.353(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.358(4) . ?
C6 H6 0.9300 . ?
C7 F1 1.360(3) . ?
C7 C8 1.417(3) . ?
C8 C9 1.391(4) . ?
C8 N2 1.402(3) . ?
C9 H9 0.9300 . ?
C10 N2 1.479(3) . ?
C10 C11 1.515(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 N3 1.482(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 N3 1.485(3) . ?
C12 C13 1.521(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 N2 1.464(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 O1 1.248(3) . ?
C14 O2 1.266(3) . ?
C15 N1 1.456(3) . ?
C15 C16 1.495(3) . ?
C15 C17 1.497(3) . ?
C15 H15 0.9800 . ?
C16 C17 1.509(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
N3 H3A 0.92(4) . ?
N3 H3B 0.862(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 C1 C2 119.8(2) . . ?
C5 C1 C14 116.5(2) . . ?
C2 C1 C14 123.7(2) . . ?
O3 C2 C1 125.0(2) . . ?
O3 C2 C3 120.9(2) . . ?
C1 C2 C3 114.0(2) . . ?
C4 C3 C6 117.5(2) . . ?
C4 C3 C2 122.4(2) . . ?
C6 C3 C2 120.1(2) . . ?
N1 C4 C9 119.7(2) . . ?
N1 C4 C3 119.3(2) . . ?
C9 C4 C3 121.0(2) . . ?
N1 C5 C1 125.3(2) . . ?
N1 C5 H5 117.4 . . ?
C1 C5 H5 117.4 . . ?
C7 C6 C3 120.5(2) . . ?
C7 C6 H6 119.8 . . ?
C3 C6 H6 119.8 . . ?
C6 C7 F1 118.4(2) . . ?
C6 C7 C8 123.4(2) . . ?
F1 C7 C8 118.1(2) . . ?
C9 C8 N2 122.5(2) . . ?
C9 C8 C7 115.8(2) . . ?
N2 C8 C7 121.5(2) . . ?
C8 C9 C4 121.6(2) . . ?
C8 C9 H9 119.2 . . ?
C4 C9 H9 119.2 . . ?
N2 C10 C11 110.48(19) . . ?
N2 C10 H10A 109.6 . . ?
C11 C10 H10A 109.6 . . ?
N2 C10 H10B 109.6 . . ?
C11 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
N3 C11 C10 109.5(2) . . ?
N3 C11 H11A 109.8 . . ?
C10 C11 H11A 109.8 . . ?
N3 C11 H11B 109.8 . . ?
C10 C11 H11B 109.8 . . ?
H11A C11 H11B 108.2 . . ?
N3 C12 C13 109.79(19) . . ?
N3 C12 H12A 109.7 . . ?
C13 C12 H12A 109.7 . . ?
N3 C12 H12B 109.7 . . ?
C13 C12 H12B 109.7 . . ?
H12A C12 H12B 108.2 . . ?
N2 C13 C12 111.4(2) . . ?
N2 C13 H13A 109.3 . . ?
C12 C13 H13A 109.3 . . ?
N2 C13 H13B 109.3 . . ?
C12 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
O1 C14 O2 125.3(2) . . ?
O1 C14 C1 118.2(2) . . ?
O2 C14 C1 116.5(2) . . ?
N1 C15 C16 119.8(2) . . ?
N1 C15 C17 119.0(2) . . ?
C16 C15 C17 60.58(16) . . ?
N1 C15 H15 115.5 . . ?
C16 C15 H15 115.5 . . ?
C17 C15 H15 115.5 . . ?
C15 C16 C17 59.77(16) . . ?
C15 C16 H16A 117.8 . . ?
C17 C16 H16A 117.8 . . ?
C15 C16 H16B 117.8 . . ?
C17 C16 H16B 117.8 . . ?
H16A C16 H16B 114.9 . . ?
C15 C17 C16 59.65(16) . . ?
C15 C17 H17A 117.8 . . ?
C16 C17 H17A 117.8 . . ?
C15 C17 H17B 117.8 . . ?
C16 C17 H17B 117.8 . . ?
H17A C17 H17B 114.9 . . ?
C5 N1 C4 119.1(2) . . ?
C5 N1 C15 119.9(2) . . ?
C4 N1 C15 119.6(2) . . ?
C8 N2 C13 115.3(2) . . ?
C8 N2 C10 115.70(19) . . ?
C13 N2 C10 111.57(18) . . ?
C11 N3 C12 108.97(18) . . ?
C11 N3 H3A 110(2) . . ?
C12 N3 H3A 108(2) . . ?
C11 N3 H3B 112(2) . . ?
C12 N3 H3B 110(2) . . ?
H3A N3 H3B 109(3) . . ?

_refine_diff_density_max         0.272
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.081

