# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_samjan142020_a
_database_code_depnum_ccdc_archive 'CCDC 1978317'
loop_
_audit_author_name
_audit_author_address
'Steven J. Geib'
;University of Pittsburgh
United States of America
;
_audit_update_record             
;
2020-01-16 deposited with the CCDC.	2020-02-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H10 F3 N3 O2'
_chemical_formula_weight         273.22

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                   6.1114(3)
_cell_length_b                   8.7281(4)
_cell_length_c                   20.9657(10)
_cell_angle_alpha                80.025(3)
_cell_angle_beta                 89.183(3)
_cell_angle_gamma                88.020(3)
_cell_volume                     1100.73(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4906
_cell_measurement_theta_min      4.282
_cell_measurement_theta_max      68.175

_exptl_crystal_description       Plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.649
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    1.314
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  .78
_exptl_absorpt_correction_T_max  .91
_exptl_absorpt_process_details   'Bruker Sadabs'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Bruker X8 Prospector Ultra Cu IMuS'
_diffrn_measurement_device_type  'Bruker Apex II CCD'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16461
_diffrn_reflns_av_unetI/netI     0.0624
_diffrn_reflns_av_R_equivalents  0.0719
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.140
_diffrn_reflns_theta_max         68.360
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.940
_diffrn_measured_fraction_theta_full 0.942
_diffrn_reflns_Laue_measured_fraction_max 0.940
_diffrn_reflns_Laue_measured_fraction_full 0.942
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_point_group_measured_fraction_full 0.942
_reflns_number_total             3806
_reflns_number_gt                3014
_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    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          "Z' = 2"
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0680P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'intrinsic phasing'
_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         3806
_refine_ls_number_parameters     367
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0983
_refine_ls_R_factor_gt           0.0813
_refine_ls_wR_factor_ref         0.2061
_refine_ls_wR_factor_gt          0.1974
_refine_ls_goodness_of_fit_ref   1.876
_refine_ls_restrained_S_all      1.875
_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 0.5023(7) 1.1308(5) 0.58054(19) 0.0311(8) Uani 1 1 d . . . . .
F1 F 0.6108(4) 1.2412(3) 0.60285(12) 0.0382(6) Uani 1 1 d . . . . .
N1 N 0.1244(6) 1.1167(4) 0.63282(17) 0.0327(7) Uani 1 1 d . . . . .
O1 O 1.0223(4) 0.7413(3) 0.93873(13) 0.0244(6) Uani 1 1 d . . . . .
C2 C 0.3505(6) 1.0454(4) 0.63100(18) 0.0253(7) Uani 1 1 d . . . . .
F2 F 0.3945(5) 1.1996(3) 0.52845(12) 0.0424(6) Uani 1 1 d . . . . .
N2 N 0.1393(6) 1.0047(4) 0.60463(17) 0.0351(8) Uani 1 1 d . . . . .
O2 O 0.7231(4) 0.8979(3) 0.92733(11) 0.0218(5) Uani 1 1 d . . . . .
C3 C 0.4391(6) 0.9442(4) 0.68966(17) 0.0239(7) Uani 1 1 d . . . . .
F3 F 0.6531(4) 1.0329(3) 0.56196(12) 0.0407(6) Uani 1 1 d . . . . .
N3 N 0.7689(5) 0.4862(3) 0.95668(14) 0.0202(6) Uani 1 1 d D . . . .
H3A H 0.889(5) 0.459(6) 0.944(3) 0.036(13) Uiso 1 1 d D . . . .
H3B H 0.760(8) 0.496(5) 0.9945(11) 0.021(10) Uiso 1 1 d D . . . .
H3C H 0.704(8) 0.408(4) 0.953(3) 0.036(13) Uiso 1 1 d D . . . .
O3 O 0.5266(4) 0.2429(3) 0.93705(12) 0.0240(5) Uani 1 1 d . . . . .
C4 C 0.3140(6) 0.8225(4) 0.72081(18) 0.0269(8) Uani 1 1 d . . . . .
H4A H 0.169454 0.811422 0.706528 0.032 Uiso 1 1 calc R U . . .
F4 F 0.3199(4) 0.7022(3) 0.58484(12) 0.0346(5) Uani 1 1 d . . . . .
N4 N -0.1901(6) 0.6899(4) 0.62814(17) 0.0348(8) Uani 1 1 d . . . . .
O4 O 0.2233(4) 0.3958(3) 0.92423(12) 0.0224(5) Uani 1 1 d . . . . .
C5 C 0.3990(6) 0.7171(4) 0.77265(18) 0.0263(8) Uani 1 1 d . . . . .
H5A H 0.312095 0.634467 0.793344 0.032 Uiso 1 1 calc R U . . .
F5 F 0.0505(4) 0.7224(3) 0.51827(12) 0.0409(6) Uani 1 1 d . . . . .
N5 N -0.2390(6) 0.5797(4) 0.60288(17) 0.0356(8) Uani 1 1 d . . . . .
C6 C 0.6106(6) 0.7315(4) 0.79464(16) 0.0235(7) Uani 1 1 d . . . . .
F6 F 0.2339(4) 0.5057(3) 0.54269(12) 0.0406(6) Uani 1 1 d . . . . .
N6 N 0.2718(5) -0.0143(3) 0.95387(14) 0.0192(6) Uani 1 1 d D . . . .
H6A H 0.395(4) -0.044(5) 0.945(2) 0.021(10) Uiso 1 1 d D . . . .
H6B H 0.193(6) -0.084(4) 0.951(2) 0.017(10) Uiso 1 1 d D . . . .
H6C H 0.263(8) -0.007(5) 0.9918(11) 0.026(11) Uiso 1 1 d D . . . .
C7 C 0.7285(6) 0.8599(4) 0.76515(18) 0.0248(7) Uani 1 1 d . . . . .
H7A H 0.869633 0.874951 0.780984 0.030 Uiso 1 1 calc R U . . .
C8 C 0.6458(6) 0.9650(4) 0.71389(18) 0.0253(7) Uani 1 1 d . . . . .
H8A H 0.729043 1.051409 0.695006 0.030 Uiso 1 1 calc R U . . .
C9 C 0.7121(6) 0.6065(4) 0.84509(17) 0.0249(7) Uani 1 1 d . . . . .
H9A H 0.870173 0.596466 0.834993 0.030 Uiso 1 1 calc R U . . .
H9B H 0.645947 0.506340 0.841607 0.030 Uiso 1 1 calc R U . . .
C10 C 0.6878(5) 0.6323(4) 0.91528(16) 0.0192(7) Uani 1 1 d . . . . .
H10A H 0.529855 0.651881 0.925318 0.023 Uiso 1 1 calc R U . . .
C11 C 0.8226(5) 0.7692(4) 0.92840(15) 0.0170(6) Uani 1 1 d . . . . .
C12 C 0.1497(7) 0.6276(4) 0.56645(18) 0.0290(8) Uani 1 1 d . . . . .
C13 C -0.0042(6) 0.5772(4) 0.62179(18) 0.0254(8) Uani 1 1 d . . . . .
C14 C 0.0639(6) 0.4657(4) 0.67989(17) 0.0227(7) Uani 1 1 d . . . . .
C15 C -0.0925(6) 0.4043(4) 0.72578(19) 0.0284(8) Uani 1 1 d . . . . .
H15A H -0.240228 0.441566 0.720950 0.034 Uiso 1 1 calc R U . . .
C16 C -0.0368(6) 0.2907(4) 0.77791(18) 0.0273(8) Uani 1 1 d . . . . .
H16A H -0.146956 0.249981 0.807934 0.033 Uiso 1 1 calc R U . . .
C17 C 0.1786(6) 0.2352(4) 0.78701(16) 0.0213(7) Uani 1 1 d . . . . .
C18 C 0.3361(6) 0.3009(4) 0.74285(18) 0.0255(7) Uani 1 1 d . . . . .
H18A H 0.484868 0.267173 0.749290 0.031 Uiso 1 1 calc R U . . .
C19 C 0.2828(6) 0.4137(4) 0.68985(18) 0.0257(7) Uani 1 1 d . . . . .
H19A H 0.393779 0.455688 0.660390 0.031 Uiso 1 1 calc R U . . .
C20 C 0.2424(6) 0.1017(4) 0.84030(17) 0.0225(7) Uani 1 1 d . . . . .
H20A H 0.400578 0.077007 0.835800 0.027 Uiso 1 1 calc R U . . .
H20B H 0.161974 0.009036 0.834003 0.027 Uiso 1 1 calc R U . . .
C21 C 0.1982(5) 0.1309(4) 0.90949(16) 0.0187(7) Uani 1 1 d . . . . .
H21A H 0.037923 0.150821 0.915779 0.022 Uiso 1 1 calc R U . . .
C22 C 0.3272(5) 0.2688(4) 0.92501(15) 0.0171(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
C1 F2 1.324(5) . ?
C1 F3 1.335(5) . ?
C1 F1 1.340(5) . ?
C1 C2 1.511(6) . ?
N1 N2 1.227(5) . ?
N1 C2 1.498(5) . ?
O1 C11 1.251(4) . ?
C2 C3 1.481(5) . ?
C2 N2 1.489(5) . ?
O2 C11 1.255(4) . ?
C3 C4 1.393(5) . ?
C3 C8 1.397(5) . ?
N3 C10 1.487(4) . ?
N3 H3A 0.82(2) . ?
N3 H3B 0.81(2) . ?
N3 H3C 0.82(2) . ?
O3 C22 1.253(4) . ?
C4 C5 1.391(5) . ?
C4 H4A 0.9500 . ?
F4 C12 1.342(5) . ?
N4 N5 1.223(6) . ?
N4 C13 1.497(5) . ?
O4 C22 1.256(4) . ?
C5 C6 1.396(5) . ?
C5 H5A 0.9500 . ?
F5 C12 1.329(5) . ?
N5 C13 1.492(5) . ?
C6 C7 1.400(5) . ?
C6 C9 1.505(5) . ?
F6 C12 1.336(5) . ?
N6 C21 1.496(4) . ?
N6 H6A 0.82(2) . ?
N6 H6B 0.80(2) . ?
N6 H6C 0.81(2) . ?
C7 C8 1.376(5) . ?
C7 H7A 0.9500 . ?
C8 H8A 0.9500 . ?
C9 C10 1.531(5) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.540(4) . ?
C10 H10A 1.0000 . ?
C12 C13 1.498(6) . ?
C13 C14 1.476(5) . ?
C14 C15 1.399(6) . ?
C14 C19 1.404(5) . ?
C15 C16 1.380(6) . ?
C15 H15A 0.9500 . ?
C16 C17 1.391(6) . ?
C16 H16A 0.9500 . ?
C17 C18 1.393(5) . ?
C17 C20 1.512(5) . ?
C18 C19 1.386(5) . ?
C18 H18A 0.9500 . ?
C19 H19A 0.9500 . ?
C20 C21 1.534(5) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.544(4) . ?
C21 H21A 1.0000 . ?

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
F2 C1 F3 108.0(3) . . ?
F2 C1 F1 107.3(3) . . ?
F3 C1 F1 106.7(3) . . ?
F2 C1 C2 111.7(3) . . ?
F3 C1 C2 110.7(3) . . ?
F1 C1 C2 112.3(3) . . ?
N2 N1 C2 65.4(3) . . ?
C3 C2 N2 118.4(3) . . ?
C3 C2 N1 119.5(3) . . ?
N2 C2 N1 48.5(2) . . ?
C3 C2 C1 120.7(3) . . ?
N2 C2 C1 114.0(3) . . ?
N1 C2 C1 115.1(3) . . ?
N1 N2 C2 66.1(3) . . ?
C4 C3 C8 119.0(3) . . ?
C4 C3 C2 118.9(3) . . ?
C8 C3 C2 122.1(3) . . ?
C10 N3 H3A 110(4) . . ?
C10 N3 H3B 109(3) . . ?
H3A N3 H3B 117(5) . . ?
C10 N3 H3C 115(4) . . ?
H3A N3 H3C 98(5) . . ?
H3B N3 H3C 107(5) . . ?
C5 C4 C3 120.5(3) . . ?
C5 C4 H4A 119.7 . . ?
C3 C4 H4A 119.7 . . ?
N5 N4 C13 65.7(3) . . ?
C4 C5 C6 120.8(3) . . ?
C4 C5 H5A 119.6 . . ?
C6 C5 H5A 119.6 . . ?
N4 N5 C13 66.0(3) . . ?
C5 C6 C7 117.7(3) . . ?
C5 C6 C9 120.5(3) . . ?
C7 C6 C9 121.6(3) . . ?
C21 N6 H6A 112(3) . . ?
C21 N6 H6B 111(3) . . ?
H6A N6 H6B 106(4) . . ?
C21 N6 H6C 113(3) . . ?
H6A N6 H6C 111(5) . . ?
H6B N6 H6C 103(5) . . ?
C8 C7 C6 121.9(3) . . ?
C8 C7 H7A 119.1 . . ?
C6 C7 H7A 119.1 . . ?
C7 C8 C3 119.9(3) . . ?
C7 C8 H8A 120.1 . . ?
C3 C8 H8A 120.1 . . ?
C6 C9 C10 115.8(3) . . ?
C6 C9 H9A 108.3 . . ?
C10 C9 H9A 108.3 . . ?
C6 C9 H9B 108.3 . . ?
C10 C9 H9B 108.3 . . ?
H9A C9 H9B 107.4 . . ?
N3 C10 C9 106.4(3) . . ?
N3 C10 C11 109.4(3) . . ?
C9 C10 C11 112.0(3) . . ?
N3 C10 H10A 109.6 . . ?
C9 C10 H10A 109.6 . . ?
C11 C10 H10A 109.6 . . ?
O1 C11 O2 126.2(3) . . ?
O1 C11 C10 116.5(3) . . ?
O2 C11 C10 117.4(3) . . ?
F5 C12 F6 107.7(3) . . ?
F5 C12 F4 107.7(3) . . ?
F6 C12 F4 106.5(3) . . ?
F5 C12 C13 111.7(3) . . ?
F6 C12 C13 111.3(3) . . ?
F4 C12 C13 111.6(3) . . ?
C14 C13 N5 117.2(3) . . ?
C14 C13 N4 118.4(3) . . ?
N5 C13 N4 48.3(2) . . ?
C14 C13 C12 122.1(3) . . ?
N5 C13 C12 114.2(3) . . ?
N4 C13 C12 114.9(3) . . ?
C15 C14 C19 118.0(3) . . ?
C15 C14 C13 120.0(3) . . ?
C19 C14 C13 121.9(3) . . ?
C16 C15 C14 121.5(3) . . ?
C16 C15 H15A 119.3 . . ?
C14 C15 H15A 119.3 . . ?
C15 C16 C17 120.8(3) . . ?
C15 C16 H16A 119.6 . . ?
C17 C16 H16A 119.6 . . ?
C16 C17 C18 117.8(3) . . ?
C16 C17 C20 122.2(3) . . ?
C18 C17 C20 119.9(3) . . ?
C19 C18 C17 122.1(3) . . ?
C19 C18 H18A 118.9 . . ?
C17 C18 H18A 118.9 . . ?
C18 C19 C14 119.7(3) . . ?
C18 C19 H19A 120.2 . . ?
C14 C19 H19A 120.2 . . ?
C17 C20 C21 115.4(3) . . ?
C17 C20 H20A 108.4 . . ?
C21 C20 H20A 108.4 . . ?
C17 C20 H20B 108.4 . . ?
C21 C20 H20B 108.4 . . ?
H20A C20 H20B 107.5 . . ?
N6 C21 C20 106.5(3) . . ?
N6 C21 C22 108.9(2) . . ?
C20 C21 C22 112.1(3) . . ?
N6 C21 H21A 109.8 . . ?
C20 C21 H21A 109.8 . . ?
C22 C21 H21A 109.8 . . ?
O3 C22 O4 126.2(3) . . ?
O3 C22 C21 116.5(3) . . ?
O4 C22 C21 117.3(3) . . ?

_refine_diff_density_max         0.630
_refine_diff_density_min         -0.492
_refine_diff_density_rms         0.137


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
