# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_exp_4915
_audit_block_doi                 10.5517/ccdc.csd.cc1z3lm9
_database_code_depnum_ccdc_archive 'CCDC 1820711'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C8CC04298E 2018
_audit_update_record             
;
2018-01-30 deposited with the CCDC.
2018-09-25 downloaded from the CCDC.
;
_audit_creation_date             2018-01-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_formula_moiety         'C17 H13 F2 N O2'
_chemical_formula_sum            'C17 H13 F2 N O2'
_chemical_formula_weight         301.29
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y,z+1/2
5 -x,-y,-z
6 -x-1/2,y-1/2,z
7 x,-y-1/2,z-1/2
8 x-1/2,y,-z-1/2

_symmetry_Int_Tables_number      61
_cell_length_a                   8.3324(7)
_cell_length_b                   18.0049(15)
_cell_length_c                   18.9382(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2841.2(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2586
_cell_measurement_temperature    296.32(10)
_cell_measurement_theta_max      27.0210
_cell_measurement_theta_min      4.2820
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41939
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.4086
_exptl_crystal_F_000             1248.8184
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_av_unetI/netI     0.0496
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            13379
_diffrn_reflns_theta_full        24.9946
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         3.94
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      296.32(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9968
_diffrn_measured_fraction_theta_max 0.9968
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0074197000
_diffrn_orient_matrix_UB_12      0.0359432000
_diffrn_orient_matrix_UB_13      -0.0150166000
_diffrn_orient_matrix_UB_21      0.0472188000
_diffrn_orient_matrix_UB_22      -0.0114007000
_diffrn_orient_matrix_UB_23      -0.0292245000
_diffrn_orient_matrix_UB_31      -0.0703699000
_diffrn_orient_matrix_UB_32      -0.0114136000
_diffrn_orient_matrix_UB_33      -0.0180243000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              0
_reflns_limit_k_max              21
_reflns_limit_k_min              0
_reflns_limit_l_max              22
_reflns_limit_l_min              0
_reflns_number_gt                1797
_reflns_number_total             2487
_reflns_odcompleteness_completeness 99.43
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2013)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2013)'
_exptl_crystal_description       block
_refine_diff_density_max         0.2258
_refine_diff_density_min         -0.2810
_refine_diff_density_rms         0.0672
_refine_ls_d_res_high            0.8410
_refine_ls_d_res_low             5.1686
_refine_ls_goodness_of_fit_ref   1.0611
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    23
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2487
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0657
_refine_ls_R_factor_gt           0.0445
_refine_ls_restrained_S_all      1.0611
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0627P)²+0.1281P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1082
_refine_ls_wR_factor_ref         0.1237
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C21(H21a,H21b)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C18(H18), C14(H14), C20(H20), C16(H16), C17(H17), C19(H19), C13(H13)
2.c Idealised Me refined as rotating group:
 C1(H1a,H1b,H1c)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
F1 F 0.12167(14) 0.70482(6) 0.48539(6) 0.0596(4) Uani 1.000000 .
F2 F -0.07258(15) 0.74955(6) 0.42202(8) 0.0655(4) Uani 1.000000 .
O3 O 0.29978(16) 0.68154(8) 0.37620(7) 0.0509(4) Uani 1.000000 .
N4 N 0.00268(18) 0.58532(8) 0.36046(8) 0.0398(4) Uani 1.000000 .
O5 O 0.12285(17) 0.74531(8) 0.31047(8) 0.0567(4) Uani 1.000000 .
C6 C -0.1986(2) 0.51941(10) 0.46364(10) 0.0374(5) Uani 1.000000 .
C7 C -0.1343(2) 0.59139(10) 0.47338(10) 0.0360(5) Uani 1.000000 .
C8 C -0.0593(2) 0.51496(10) 0.34960(10) 0.0395(5) Uani 1.000000 .
C9 C -0.0335(2) 0.62004(10) 0.41842(10) 0.0357(4) Uani 1.000000 .
C10 C 0.1585(2) 0.71078(10) 0.36200(11) 0.0424(5) Uani 1.000000 .
C11 C -0.1616(2) 0.48063(10) 0.39859(10) 0.0395(5) Uani 1.000000 .
C12 C -0.1707(2) 0.63076(11) 0.53592(11) 0.0467(5) Uani 1.000000 .
C13 C -0.2208(2) 0.40951(11) 0.38193(12) 0.0499(6) Uani 1.000000 .
C14 C -0.3231(3) 0.52795(13) 0.57815(12) 0.0599(6) Uani 1.000000 .
C15 C 0.0423(2) 0.69602(10) 0.42315(10) 0.0425(5) Uani 1.000000 .
C16 C -0.0137(3) 0.47753(11) 0.28772(11) 0.0522(6) Uani 1.000000 .
C17 C -0.0704(3) 0.40810(12) 0.27392(12) 0.0580(6) Uani 1.000000 .
C18 C -0.2628(3) 0.59943(13) 0.58693(12) 0.0572(6) Uani 1.000000 .
C19 C -0.1762(3) 0.37453(12) 0.32071(13) 0.0570(6) Uani 1.000000 .
C20 C -0.2921(2) 0.48887(12) 0.51792(12) 0.0504(6) Uani 1.000000 .
C21 C 0.4216(3) 0.68809(15) 0.32141(13) 0.0666(7) Uani 1.000000 .
C1 C 0.5739(3) 0.66088(16) 0.35196(15) 0.0789(8) Uani 1.000000 .
H12 H -0.1310(2) 0.67860(11) 0.54217(11) 0.0561(6) Uiso 1.000000 R
H18 H -0.2858(3) 0.62582(13) 0.62792(12) 0.0686(7) Uiso 1.000000 R
H14 H -0.3851(3) 0.50663(13) 0.61360(12) 0.0718(8) Uiso 1.000000 R
H20 H -0.3336(2) 0.44123(12) 0.51281(12) 0.0605(7) Uiso 1.000000 R
H16 H 0.0557(3) 0.50032(11) 0.25595(11) 0.0626(7) Uiso 1.000000 R
H17 H -0.0384(3) 0.38323(12) 0.23325(12) 0.0696(7) Uiso 1.000000 R
H19 H -0.2173(3) 0.32775(12) 0.31040(13) 0.0684(7) Uiso 1.000000 R
H13 H -0.2910(2) 0.38597(11) 0.41285(12) 0.0599(7) Uiso 1.000000 R
H21a H 0.3922(3) 0.65854(15) 0.28059(13) 0.0800(8) Uiso 1.000000 R
H21b H 0.4326(3) 0.73945(15) 0.30673(13) 0.0800(8) Uiso 1.000000 R
H1a H 0.6581(6) 0.6656(10) 0.3176(4) 0.1184(12) Uiso 1.000000 GR
H1b H 0.6002(12) 0.6897(7) 0.3930(6) 0.1184(12) Uiso 1.000000 GR
H1c H 0.5623(8) 0.6097(3) 0.3651(9) 0.1184(12) Uiso 1.000000 GR


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 C15 1.361(2) . ?
F2 C15 1.359(2) . ?
O3 C10 1.317(2) . ?
O3 C21 1.456(3) . ?
N4 C8 1.384(2) . ?
N4 C9 1.299(2) . ?
O5 C10 1.195(2) . ?
C6 C7 1.414(2) . ?
C6 C11 1.449(3) . ?
C6 C20 1.402(3) . ?
C7 C9 1.434(3) . ?
C7 C12 1.413(3) . ?
C8 C11 1.403(3) . ?
C8 C16 1.404(3) . ?
C9 C15 1.509(3) . ?
C10 C15 1.533(3) . ?
C11 C13 1.408(3) . ?
C12 C18 1.357(3) . ?
C13 C19 1.371(3) . ?
C14 C18 1.392(3) . ?
C14 C20 1.365(3) . ?
C16 C17 1.362(3) . ?
C17 C19 1.388(3) . ?
C21 C1 1.478(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
C21 O3 C10 116.44(16) . . ?
C9 N4 C8 118.68(16) . . ?
C11 C6 C7 118.14(17) . . ?
C20 C6 C7 118.31(18) . . ?
C20 C6 C11 123.54(18) . . ?
C9 C7 C6 117.20(16) . . ?
C12 C7 C6 119.19(17) . . ?
C12 C7 C9 123.61(17) . . ?
C11 C8 N4 122.13(17) . . ?
C16 C8 N4 117.54(18) . . ?
C16 C8 C11 120.32(18) . . ?
C7 C9 N4 125.19(16) . . ?
C15 C9 N4 112.92(16) . . ?
C15 C9 C7 121.89(16) . . ?
O5 C10 O3 126.65(19) . . ?
C15 C10 O3 109.93(16) . . ?
C15 C10 O5 123.40(18) . . ?
C8 C11 C6 118.62(17) . . ?
C13 C11 C6 123.64(19) . . ?
C13 C11 C8 117.73(18) . . ?
C18 C12 C7 120.63(19) . . ?
C19 C13 C11 120.8(2) . . ?
C20 C14 C18 120.5(2) . . ?
F2 C15 F1 105.87(15) . . ?
C9 C15 F1 111.12(15) . . ?
C9 C15 F2 110.31(15) . . ?
C10 C15 F1 109.12(15) . . ?
C10 C15 F2 108.06(15) . . ?
C10 C15 C9 112.12(16) . . ?
C17 C16 C8 120.4(2) . . ?
C19 C17 C16 119.8(2) . . ?
C14 C18 C12 120.2(2) . . ?
C17 C19 C13 120.8(2) . . ?
C14 C20 C6 121.05(19) . . ?
C1 C21 O3 107.02(19) . . ?

_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.864
_oxdiff_exptl_absorpt_empirical_full_min 0.618
