# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_16112908
_database_code_depnum_ccdc_archive 'CCDC 1542511'
_audit_update_record             
;
2017-04-06 deposited with the CCDC.
2017-06-12 downloaded from the CCDC.
;
_audit_creation_date             2016-12-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C11 H9 F4 N O2'
_chemical_formula_sum            'C11 H9 F4 N O2'
_chemical_formula_weight         263.19
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N F'
_chemical_oxdiff_usercomment     HW0823-1
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      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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   9.57475(17)
_cell_length_b                   13.6182(2)
_cell_length_c                   8.60542(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.8820(17)
_cell_angle_gamma                90.00
_cell_volume                     1108.61(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2631
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      74.1590
_cell_measurement_theta_min      4.6550
_exptl_absorpt_coefficient_mu    1.359
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42712
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.577
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4161
_diffrn_reflns_theta_full        74.38
_diffrn_reflns_theta_max         74.38
_diffrn_reflns_theta_min         4.67
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2913
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -42.00  -3.00   1.00    1.00    --  -41.89 125.00-180.00   39
  2  ω   -110.00 -18.00   1.00    1.00    --  -41.89 -37.00 -60.00   92
  3  ω     95.00 151.00   1.00    1.01    --  108.44 125.00  30.00   56
  4  ω     82.00 172.00   1.00    1.01    --  108.44  61.00 150.00   90
  5  ω     80.00 138.00   1.00    1.01    --  108.44  30.00 120.00   58
  6  ω     89.00 131.00   1.00    1.01    --  108.44 -45.00 -60.00   42
  7  ω     48.00  74.00   1.00    1.01    --  108.44 -45.00 -60.00   26
  8  ω     48.00 140.00   1.00    1.01    --  108.44 -77.00   0.00   92
  9  ω     35.00  70.00   1.00    1.00    --   41.89-125.00   0.00   35
 10  ω     37.00  72.00   1.00    1.01    --  108.44-125.00 -30.00   35
 11  ω     24.00  98.00   1.00    1.00    --   41.89-125.00-150.00   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1491133000
_diffrn_orient_matrix_UB_12      -0.0455049000
_diffrn_orient_matrix_UB_13      0.0277780000
_diffrn_orient_matrix_UB_21      -0.0598975000
_diffrn_orient_matrix_UB_22      -0.0960862000
_diffrn_orient_matrix_UB_23      -0.0779317000
_diffrn_orient_matrix_UB_31      0.0263700000
_diffrn_orient_matrix_UB_32      0.0386411000
_diffrn_orient_matrix_UB_33      -0.1612247000
_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              'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2026
_reflns_number_total             2186
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.29
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2013)'
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2186
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0377
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0592P)²+0.2326P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1036
_refine_ls_wR_factor_ref         0.1065
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N7(H7), C8(H8), C14(H14), C15(H15), C16(H16), C17(H17)
2.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
F1 F 0.74916(10) 0.71021(6) 0.61417(11) 0.0362(2) Uani 1 d . . .
F2 F 0.82244(11) 0.81382(7) 0.79647(10) 0.0395(3) Uani 1 d . . .
F3 F 0.43292(9) 1.06935(6) 0.17062(11) 0.0365(2) Uani 1 d . . .
F4 F 0.94982(9) 0.78225(7) 0.61891(12) 0.0380(2) Uani 1 d . . .
O5 O 0.73597(12) 1.04726(7) 0.48979(13) 0.0355(3) Uani 1 d . . .
O6 O 0.90673(11) 0.98643(8) 0.67264(13) 0.0358(3) Uani 1 d . . .
N7 N 0.55947(12) 0.91884(9) 0.33042(13) 0.0269(3) Uani 1 d . . .
H7 H 0.5824 0.9795 0.3459 0.032 Uiso 1 calc . . R
C8 C 0.63148(14) 0.85353(10) 0.42791(16) 0.0252(3) Uani 1 d . . .
H8 H 0.6038 0.7881 0.4177 0.030 Uiso 1 calc . . R
C9 C 0.81519(15) 0.79764(10) 0.64165(17) 0.0284(3) Uani 1 d . . .
C10 C 0.74269(14) 0.87642(10) 0.54133(16) 0.0252(3) Uani 1 d . . .
C11 C 0.79222(15) 0.97776(10) 0.56329(16) 0.0265(3) Uani 1 d . . .
C12 C 0.38605(15) 0.97799(10) 0.12286(18) 0.0291(3) Uani 1 d . . .
C13 C 0.45088(14) 0.89887(10) 0.20610(16) 0.0259(3) Uani 1 d . . .
C14 C 0.29699(17) 0.79374(12) 0.0302(2) 0.0366(4) Uani 1 d . . .
H14 H 0.2665 0.7310 -0.0015 0.044 Uiso 1 calc . . R
C15 C 0.40373(16) 0.80499(11) 0.15775(18) 0.0311(3) Uani 1 d . . .
H15 H 0.4439 0.7500 0.2111 0.037 Uiso 1 calc . . R
C16 C 0.23533(18) 0.87446(13) -0.0505(2) 0.0411(4) Uani 1 d . . .
H16 H 0.1639 0.8660 -0.1358 0.049 Uiso 1 calc . . R
C17 C 0.28074(17) 0.96825(12) -0.0033(2) 0.0377(4) Uani 1 d . . .
H17 H 0.2404 1.0233 -0.0563 0.045 Uiso 1 calc . . R
C18 C 0.95542(19) 1.08589(12) 0.7062(2) 0.0442(4) Uani 1 d . . .
H18A H 0.9829 1.1144 0.6134 0.066 Uiso 1 calc . . GR
H18B H 1.0351 1.0852 0.7890 0.066 Uiso 1 calc . . GR
H18C H 0.8806 1.1241 0.7384 0.066 Uiso 1 calc . . GR

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.0448(5) 0.0192(4) 0.0418(5) 0.0066(4) -0.0019(4) -0.0038(3)
F2 0.0542(6) 0.0345(5) 0.0276(5) 0.0053(4) -0.0005(4) 0.0018(4)
F3 0.0428(5) 0.0185(4) 0.0453(5) -0.0015(4) -0.0031(4) 0.0026(3)
F4 0.0315(5) 0.0304(5) 0.0513(6) 0.0092(4) 0.0038(4) 0.0078(3)
O5 0.0411(6) 0.0187(5) 0.0425(6) 0.0026(4) -0.0063(5) 0.0018(4)
O6 0.0351(6) 0.0212(5) 0.0464(6) 0.0006(4) -0.0084(5) -0.0027(4)
N7 0.0298(6) 0.0189(5) 0.0305(6) -0.0010(5) 0.0001(5) 0.0015(4)
C8 0.0283(7) 0.0199(6) 0.0279(6) 0.0005(5) 0.0059(5) 0.0001(5)
C9 0.0309(7) 0.0224(6) 0.0305(7) 0.0020(6) 0.0006(5) -0.0011(5)
C10 0.0282(7) 0.0185(6) 0.0288(7) 0.0013(5) 0.0047(5) 0.0010(5)
C11 0.0285(7) 0.0211(6) 0.0293(7) 0.0001(5) 0.0020(5) 0.0010(5)
C12 0.0314(7) 0.0199(6) 0.0356(7) -0.0010(6) 0.0032(6) 0.0011(5)
C13 0.0275(7) 0.0216(6) 0.0283(7) -0.0002(5) 0.0032(5) 0.0021(5)
C14 0.0391(8) 0.0265(7) 0.0412(8) -0.0044(6) -0.0027(7) -0.0048(6)
C15 0.0356(8) 0.0206(7) 0.0358(8) 0.0000(6) 0.0014(6) 0.0008(6)
C16 0.0382(8) 0.0388(9) 0.0409(9) -0.0010(7) -0.0105(7) -0.0026(7)
C17 0.0396(8) 0.0289(8) 0.0407(9) 0.0047(6) -0.0066(7) 0.0043(6)
C18 0.0427(9) 0.0241(7) 0.0597(11) -0.0013(7) -0.0118(8) -0.0078(6)

_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
F1 C9 1.3517(16) . ?
F2 C9 1.3416(17) . ?
F3 C12 1.3642(16) . ?
F4 C9 1.3496(17) . ?
O5 C11 1.2168(17) . ?
O6 C11 1.3352(17) . ?
O6 C18 1.4470(18) . ?
N7 H7 0.8600 . ?
N7 C8 1.3385(18) . ?
N7 C13 1.3986(17) . ?
C8 H8 0.9300 . ?
C8 C10 1.3648(19) . ?
C9 C10 1.4809(19) . ?
C10 C11 1.4621(19) . ?
C12 C13 1.386(2) . ?
C12 C17 1.369(2) . ?
C13 C15 1.398(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.388(2) . ?
C14 C16 1.383(2) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C16 C17 1.389(2) . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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
C11 O6 C18 115.32(12) . . ?
C8 N7 H7 116.6 . . ?
C8 N7 C13 126.89(12) . . ?
C13 N7 H7 116.6 . . ?
N7 C8 H8 117.8 . . ?
N7 C8 C10 124.47(13) . . ?
C10 C8 H8 117.8 . . ?
F1 C9 C10 111.82(12) . . ?
F2 C9 F1 105.63(11) . . ?
F2 C9 F4 105.39(11) . . ?
F2 C9 C10 114.06(12) . . ?
F4 C9 F1 105.62(11) . . ?
F4 C9 C10 113.59(12) . . ?
C8 C10 C9 119.68(12) . . ?
C8 C10 C11 120.64(12) . . ?
C11 C10 C9 119.67(12) . . ?
O5 C11 O6 123.15(13) . . ?
O5 C11 C10 123.94(13) . . ?
O6 C11 C10 112.91(12) . . ?
F3 C12 C13 116.93(13) . . ?
F3 C12 C17 119.67(13) . . ?
C17 C12 C13 123.40(14) . . ?
C12 C13 N7 117.69(13) . . ?
C12 C13 C15 117.31(13) . . ?
C15 C13 N7 124.99(12) . . ?
C15 C14 H14 119.5 . . ?
C16 C14 H14 119.5 . . ?
C16 C14 C15 120.96(14) . . ?
C13 C15 H15 120.0 . . ?
C14 C15 C13 120.06(14) . . ?
C14 C15 H15 120.0 . . ?
C14 C16 H16 120.2 . . ?
C14 C16 C17 119.60(14) . . ?
C17 C16 H16 120.2 . . ?
C12 C17 C16 118.67(14) . . ?
C12 C17 H17 120.7 . . ?
C16 C17 H17 120.7 . . ?
O6 C18 H18A 109.5 . . ?
O6 C18 H18B 109.5 . . ?
O6 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

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
F1 C9 C10 C8 -5.74(19) . . . . ?
F1 C9 C10 C11 175.12(12) . . . . ?
F2 C9 C10 C8 -125.51(14) . . . . ?
F2 C9 C10 C11 55.34(18) . . . . ?
F3 C12 C13 N7 -0.7(2) . . . . ?
F3 C12 C13 C15 -179.86(12) . . . . ?
F3 C12 C17 C16 179.58(15) . . . . ?
F4 C9 C10 C8 113.69(14) . . . . ?
F4 C9 C10 C11 -65.46(17) . . . . ?
N7 C8 C10 C9 -179.49(13) . . . . ?
N7 C8 C10 C11 -0.4(2) . . . . ?
N7 C13 C15 C14 -178.54(14) . . . . ?
C8 N7 C13 C12 177.52(13) . . . . ?
C8 N7 C13 C15 -3.4(2) . . . . ?
C8 C10 C11 O5 3.4(2) . . . . ?
C8 C10 C11 O6 -176.31(12) . . . . ?
C9 C10 C11 O5 -177.42(14) . . . . ?
C9 C10 C11 O6 2.82(19) . . . . ?
C12 C13 C15 C14 0.6(2) . . . . ?
C13 N7 C8 C10 175.67(13) . . . . ?
C13 C12 C17 C16 0.4(3) . . . . ?
C14 C16 C17 C12 0.0(3) . . . . ?
C15 C14 C16 C17 0.0(3) . . . . ?
C16 C14 C15 C13 -0.2(3) . . . . ?
C17 C12 C13 N7 178.52(14) . . . . ?
C17 C12 C13 C15 -0.6(2) . . . . ?
C18 O6 C11 O5 3.8(2) . . . . ?
C18 O6 C11 C10 -176.40(14) . . . . ?

_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 2.165
_oxdiff_exptl_absorpt_empirical_full_min 0.587
