# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_201707127
_database_code_depnum_ccdc_archive 'CCDC 1814419'
_audit_update_record             
;
2018-01-03 deposited with the CCDC.
2018-06-04 downloaded from the CCDC.
;
_audit_creation_date             2017-07-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H7 F3 N2 O2'
_chemical_formula_sum            'C11 H7 F3 N2 O2'
_chemical_formula_weight         256.19
_chemical_melting_point          ?
_chemical_oxdiff_formula         C38H70N2O2F3
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'
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                   4.5680(3)
_cell_length_b                   16.1861(8)
_cell_length_c                   15.8035(10)
_cell_angle_alpha                90
_cell_angle_beta                 115.336(7)
_cell_angle_gamma                90
_cell_volume                     1056.09(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1647
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.7950
_cell_measurement_theta_min      4.1070
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.303
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93372
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.611
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            3784
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.069
_diffrn_reflns_theta_max         67.069
_diffrn_reflns_theta_min         4.128
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -102.00  -15.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000  -60.0000 87

#__ type_ start__ end____ width___ exp.time_
  2 omega -106.00    4.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -19.0000  -60.0000 110

#__ type_ start__ end____ width___ exp.time_
  3 omega   15.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000    0.0000 62

#__ type_ start__ end____ width___ exp.time_
  4 omega   30.00   56.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -77.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
  5 omega   69.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000    0.0000 40

#__ type_ start__ end____ width___ exp.time_
  6 omega  -22.00   13.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -77.0000 -150.0000 35

#__ type_ start__ end____ width___ exp.time_
  7 omega   79.00  105.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
  8 omega   39.00   75.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -90.0000 36

#__ type_ start__ end____ width___ exp.time_
  9 omega   43.00   98.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   90.0000 55

#__ type_ start__ end____ width___ exp.time_
 10 omega   38.00   87.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 49

#__ type_ start__ end____ width___ exp.time_
 11 omega   64.00  148.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000  150.0000 84

#__ type_ start__ end____ width___ exp.time_
 12 omega   91.00  139.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -180.0000 48

#__ type_ start__ end____ width___ exp.time_
 13 omega   94.00  175.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   90.0000 81

#__ type_ start__ end____ width___ exp.time_
 14 omega   58.00   84.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 15 omega   41.00   93.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -150.0000 52

#__ type_ start__ end____ width___ exp.time_
 16 omega   38.00   78.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 40
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1381303000
_diffrn_orient_matrix_UB_12      -0.0641598000
_diffrn_orient_matrix_UB_13      -0.0794018000
_diffrn_orient_matrix_UB_21      -0.1342422000
_diffrn_orient_matrix_UB_22      0.0703048000
_diffrn_orient_matrix_UB_23      -0.0721515000
_diffrn_orient_matrix_UB_31      0.3196289000
_diffrn_orient_matrix_UB_32      0.0017717000
_diffrn_orient_matrix_UB_33      -0.0107481000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1558
_reflns_number_total             1881
_reflns_odcompleteness_completeness 99.64
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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         0.241
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.0133(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         1881
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0438
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0840P)²+0.1495P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1310
_refine_ls_wR_factor_ref         0.1427
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(O2) = Uanis(O2A)
3. Others
 Sof(O2A)=1-FVAR(1)
 Sof(O2)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C7(H7), C8(H8), C9(H9)
;
_atom_sites_solution_hydrogens   mixed
_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
C1 C -0.1295(6) 0.20427(14) 0.68406(16) 0.0555(6) Uani 1 1 d . . . . .
H1 H -0.1242 0.1749 0.7353 0.067 Uiso 1 1 calc R . . . .
C2 C -0.3588(6) 0.18369(14) 0.59502(17) 0.0570(6) Uani 1 1 d . . . . .
H2 H -0.5055 0.1413 0.5872 0.068 Uiso 1 1 calc R . . . .
C3 C -0.3687(5) 0.22532(13) 0.51961(15) 0.0502(5) Uani 1 1 d . . . . .
H3 H -0.5221 0.2118 0.4598 0.060 Uiso 1 1 calc R . . . .
C4 C -0.1451(5) 0.28927(12) 0.53231(13) 0.0431(5) Uani 1 1 d . . . . .
C5 C 0.0872(4) 0.31035(11) 0.62331(12) 0.0380(4) Uani 1 1 d . . . . .
C6 C 0.3149(5) 0.37485(12) 0.63608(13) 0.0399(4) Uani 1 1 d . . . . .
C7 C 0.3020(5) 0.41557(14) 0.55806(14) 0.0506(5) Uani 1 1 d . . . . .
H7 H 0.4495 0.4576 0.5652 0.061 Uiso 1 1 calc R . . . .
C8 C 0.0708(6) 0.39486(15) 0.46823(15) 0.0583(6) Uani 1 1 d . . . . .
H8 H 0.0667 0.4236 0.4168 0.070 Uiso 1 1 calc R . . . .
C9 C -0.1467(5) 0.33382(14) 0.45503(14) 0.0544(6) Uani 1 1 d . . . . .
H9 H -0.2983 0.3210 0.3948 0.065 Uiso 1 1 calc R . . . .
C10 C 0.7679(5) 0.45251(13) 0.75471(15) 0.0498(5) Uani 1 1 d . . . . .
C11 C 0.9627(5) 0.45787(14) 0.86116(15) 0.0508(5) Uani 1 1 d . . . . .
F1 F 0.9187(3) 0.39445(9) 0.90758(9) 0.0693(5) Uani 1 1 d . . . . .
F2 F 1.2755(3) 0.46313(12) 0.88404(12) 0.0819(5) Uani 1 1 d . . . . .
F3 F 0.8813(4) 0.52578(10) 0.89343(11) 0.0745(5) Uani 1 1 d . . . . .
N1 N 0.0835(4) 0.26519(10) 0.69810(11) 0.0455(4) Uani 1 1 d . . . . .
N2 N 0.5434(4) 0.39350(10) 0.72714(11) 0.0430(4) Uani 1 1 d . . . . .
H2A H 0.516(6) 0.3620(16) 0.7688(19) 0.065(7) Uiso 1 1 d . . . . .
O1 O 0.2897(4) 0.28178(11) 0.78530(10) 0.0710(6) Uani 1 1 d . . . . .
O2 O 0.8548(19) 0.4976(4) 0.7074(3) 0.0715(14) Uani 0.758(18) 1 d . . P A 1
O2A O 0.738(5) 0.5155(11) 0.7077(10) 0.0715(14) Uani 0.242(18) 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
C1 H1 0.9300 . ?
C1 C2 1.388(3) . ?
C1 N1 1.336(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.353(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.407(3) . ?
C4 C5 1.416(3) . ?
C4 C9 1.415(3) . ?
C5 C6 1.426(3) . ?
C5 N1 1.396(2) . ?
C6 C7 1.377(3) . ?
C6 N2 1.402(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.400(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.352(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.532(3) . ?
C10 N2 1.331(3) . ?
C10 O2 1.226(5) . ?
C10 O2A 1.235(15) . ?
C11 F1 1.326(3) . ?
C11 F2 1.318(2) . ?
C11 F3 1.330(3) . ?
N1 O1 1.322(2) . ?
N2 H2A 0.88(3) . ?

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
C2 C1 H1 119.1 . . ?
N1 C1 H1 119.1 . . ?
N1 C1 C2 121.7(2) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.0(2) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 120.3 . . ?
C2 C3 C4 119.49(19) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 C5 120.32(18) . . ?
C3 C4 C9 121.08(18) . . ?
C9 C4 C5 118.60(18) . . ?
C4 C5 C6 120.29(17) . . ?
N1 C5 C4 117.29(17) . . ?
N1 C5 C6 122.41(16) . . ?
C7 C6 C5 118.33(18) . . ?
C7 C6 N2 122.94(18) . . ?
N2 C6 C5 118.72(16) . . ?
C6 C7 H7 119.4 . . ?
C6 C7 C8 121.2(2) . . ?
C8 C7 H7 119.4 . . ?
C7 C8 H8 119.4 . . ?
C9 C8 C7 121.12(19) . . ?
C9 C8 H8 119.4 . . ?
C4 C9 H9 119.8 . . ?
C8 C9 C4 120.45(19) . . ?
C8 C9 H9 119.8 . . ?
N2 C10 C11 113.84(18) . . ?
O2 C10 C11 116.6(2) . . ?
O2 C10 N2 129.3(3) . . ?
O2A C10 C11 118.5(7) . . ?
O2A C10 N2 121.6(7) . . ?
F1 C11 C10 114.16(17) . . ?
F1 C11 F3 107.11(18) . . ?
F2 C11 C10 110.91(18) . . ?
F2 C11 F1 107.55(19) . . ?
F2 C11 F3 106.82(18) . . ?
F3 C11 C10 109.97(19) . . ?
C1 N1 C5 121.20(17) . . ?
O1 N1 C1 117.82(17) . . ?
O1 N1 C5 120.98(16) . . ?
C6 N2 H2A 111.1(18) . . ?
C10 N2 C6 128.42(18) . . ?
C10 N2 H2A 120.3(18) . . ?

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
N2 H2A O1 0.88(3) 1.75(3) 2.524(2) 145(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
C1 C2 C3 C4 0.1(3) . . . . ?
C2 C1 N1 C5 -0.8(3) . . . . ?
C2 C1 N1 O1 178.8(2) . . . . ?
C2 C3 C4 C5 -0.4(3) . . . . ?
C2 C3 C4 C9 179.6(2) . . . . ?
C3 C4 C5 C6 179.65(17) . . . . ?
C3 C4 C5 N1 0.2(3) . . . . ?
C3 C4 C9 C8 -179.7(2) . . . . ?
C4 C5 C6 C7 0.0(3) . . . . ?
C4 C5 C6 N2 -179.39(16) . . . . ?
C4 C5 N1 C1 0.4(3) . . . . ?
C4 C5 N1 O1 -179.12(18) . . . . ?
C5 C4 C9 C8 0.4(3) . . . . ?
C5 C6 C7 C8 0.3(3) . . . . ?
C5 C6 N2 C10 -177.51(19) . . . . ?
C6 C5 N1 C1 -179.04(19) . . . . ?
C6 C5 N1 O1 1.4(3) . . . . ?
C6 C7 C8 C9 -0.3(4) . . . . ?
C7 C6 N2 C10 3.1(3) . . . . ?
C7 C8 C9 C4 0.0(4) . . . . ?
C9 C4 C5 C6 -0.4(3) . . . . ?
C9 C4 C5 N1 -179.82(17) . . . . ?
C11 C10 N2 C6 176.49(18) . . . . ?
N1 C1 C2 C3 0.5(4) . . . . ?
N1 C5 C6 C7 179.45(17) . . . . ?
N1 C5 C6 N2 0.0(3) . . . . ?
N2 C6 C7 C8 179.72(19) . . . . ?
N2 C10 C11 F1 11.5(3) . . . . ?
N2 C10 C11 F2 133.2(2) . . . . ?
N2 C10 C11 F3 -108.9(2) . . . . ?
O2 C10 C11 F1 -163.0(5) . . . . ?
O2 C10 C11 F2 -41.3(6) . . . . ?
O2 C10 C11 F3 76.6(5) . . . . ?
O2 C10 N2 C6 -9.8(7) . . . . ?
O2A C10 C11 F1 164.6(11) . . . . ?
O2A C10 C11 F2 -73.7(11) . . . . ?
O2A C10 C11 F3 44.3(11) . . . . ?
O2A C10 N2 C6 24.3(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
