# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2012


#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication 
#  deposited with the CCDC, and may include chemical, crystal,   
#  experimental, refinement, atomic coordinates, 
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted. 
# 
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material 
#  of the CCDC or of third parties, and may not be copied or further 
#  disseminated in any form, whether machine-readable or not,  
#  except for the purpose of generating routine backup copies 
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and 
#  data retrieval see:
#                         www.ccdc.cam.ac.uk 
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively. 
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data_nacf1
_database_code_depnum_ccdc_archive 'CCDC 873622'
#TrackingRef 'CIF-3.cif'



_computing_structure_solution    ?
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_atom_sites_solution_primary     ?
_atom_sites_solution_hydrogens   ?
_atom_sites_solution_secondary   ?
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94287
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_type   multi-scan
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_exptl_crystal_description       'orange, rectangular'
_cell_measurement_temperature    293(2)
_cell_measurement_theta_min      3.2943
_diffrn_radiation_type           'Mo K\a'
_symmetry_space_group_name_hall  '-P 1'
_cell_special_details            ?
_audit_update_record             
;
2012-03-27 # Formatted by publCIF
;
_chemical_formula_moiety         'C21 H12 F3 N O3'
_chemical_formula_sum            'C21 H12 F3 N O3'
_chemical_formula_weight         383.33
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
H 0.00000 0.00000 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
C 0.00347 0.00161 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
F 0.01794 0.01033 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
O 0.01158 0.00611 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
N 0.00653 0.00323 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_cell_length_a                   6.2911(7)
_cell_length_b                   11.5341(13)
_cell_length_c                   12.3473(13)
_cell_angle_alpha                109.076(10)
_cell_angle_beta                 99.931(9)
_cell_angle_gamma                91.579(9)
_cell_volume                     830.66(17)
_cell_formula_units_Z            2
_exptl_crystal_colour            Orange
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_exptl_absorpt_coefficient_mu    0.125
_exptl_crystal_density_diffrn    1.5325
_exptl_crystal_F_000             392.2825
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6250
_diffrn_reflns_theta_full        25.000000
_diffrn_reflns_theta_max         29.01
_diffrn_reflns_theta_min         3.30
_diffrn_measured_fraction_theta_full 0.998636
_diffrn_measured_fraction_theta_max 0.847767
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              7
_reflns_limit_h_min              -8
_reflns_limit_k_max              14
_reflns_limit_k_min              -15
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                2460
_reflns_number_total             3759
_reflns_threshold_expression     I>=2u(I)
_refine_diff_density_max         0.455992
_refine_diff_density_min         -0.300052
_refine_diff_density_rms         0.069544
_refine_ls_d_res_high            0.732662
_refine_ls_d_res_low             6.171605
_refine_ls_goodness_of_fit_ref   1.026947
_refine_ls_hydrogen_treatment    ?
_refine_ls_matrix_type           full
_refine_ls_number_constraints    8
_refine_ls_number_parameters     284
_refine_ls_number_reflns         3759
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.086199
_refine_ls_R_factor_gt           0.053012
_refine_ls_restrained_S_all      1.026947
_refine_ls_shift/su_max          0.0004
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[\s^2^(Fo^2^)+(0.0696P)^2^+0.1065P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.153978
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
O2 O 0.5820(2) 0.57843(12) 0.14527(10) 0.0406(3) Uani 1.000000 .
N1 N -0.0337(2) 0.40536(15) 0.23718(13) 0.0402(4) Uani 1.000000 .
O3 O -0.3510(2) 0.32254(15) 0.30253(12) 0.0577(4) Uani 1.000000 .
H3 H -0.2327(2) 0.35772(15) 0.30780(12) 0.0865(7) Uiso 1.000000 R
O1 O 0.8676(2) 0.64300(15) 0.09358(12) 0.0564(4) Uani 1.000000 .
C10 C 0.2804(3) 0.49605(18) 0.18923(15) 0.0371(4) Uani 1.000000 .
F1 F 0.8735(3) 0.73083(16) 0.57159(11) 0.0825(5) Uani 1.000000 .
C6 C 0.5459(3) 0.63887(17) 0.34818(15) 0.0365(4) Uani 1.000000 .
C5 C 0.4684(3) 0.57227(17) 0.22961(15) 0.0344(4) Uani 1.000000 .
F3 F 1.0133(3) 0.86367(16) 0.51216(13) 0.0973(6) Uani 1.000000 .
C11 C -0.1263(3) 0.33682(17) 0.12842(16) 0.0374(4) Uani 1.000000 .
C13 C -0.4141(3) 0.18735(16) -0.01749(16) 0.0369(4) Uani 1.000000 .
C12 C -0.3184(3) 0.26279(17) 0.10208(16) 0.0359(4) Uani 1.000000 .
C18 C -0.6168(3) 0.12028(17) -0.04076(18) 0.0438(5) Uani 1.000000 .
C9 C 0.1600(3) 0.48167(17) 0.26911(15) 0.0364(4) Uani 1.000000 .
C4 C 0.7740(3) 0.64789(18) 0.17220(16) 0.0409(5) Uani 1.000000 .
C21 C -0.4298(3) 0.26258(18) 0.19516(17) 0.0425(5) Uani 1.000000 .
C8 C 0.2353(3) 0.5458(2) 0.38863(16) 0.0436(5) Uani 1.000000 .
F2 F 0.6909(3) 0.87441(14) 0.54315(13) 0.0951(6) Uani 1.000000 .
C7 C 0.4210(3) 0.62266(19) 0.42709(16) 0.0421(5) Uani 1.000000 .
C2 C 0.7435(3) 0.71679(17) 0.37681(15) 0.0399(5) Uani 1.000000 .
C14 C -0.3115(4) 0.17684(19) -0.11242(17) 0.0465(5) Uani 1.000000 .
H14 H -0.1774(4) 0.22012(19) -0.09967(17) 0.0558(6) Uiso 1.000000 R
C3 C 0.8519(3) 0.72094(19) 0.29364(17) 0.0439(5) Uani 1.000000 .
C19 C -0.7242(3) 0.1284(2) 0.0544(2) 0.0523(6) Uani 1.000000 .
H19 H -0.8605(3) 0.0864(2) 0.0385(2) 0.0627(7) Uiso 1.000000 R
C20 C -0.6362(4) 0.1940(2) 0.1655(2) 0.0509(5) Uani 1.000000 .
C1 C 0.8311(4) 0.7968(2) 0.50132(19) 0.0602(6) Uani 1.000000 .
C15 C -0.4066(4) 0.1033(2) -0.2242(2) 0.0562(6) Uani 1.000000 .
C17 C -0.7100(4) 0.0465(2) -0.1556(2) 0.0548(6) Uani 1.000000 .
C16 C -0.6053(4) 0.0374(2) -0.2459(2) 0.0606(7) Uani 1.000000 .
H16 H -0.6673(4) -0.0128(2) -0.3214(2) 0.0727(8) Uiso 1.000000 R
H3a H 0.975(4) 0.768(2) 0.3081(19) 0.054(6) Uiso 1.000000 .
H15 H -0.325(4) 0.097(2) -0.289(2) 0.061(7) Uiso 1.000000 .
H10 H 0.234(3) 0.4558(19) 0.1063(19) 0.047(6) Uiso 1.000000 .
H11 H -0.049(3) 0.3403(19) 0.0650(19) 0.052(6) Uiso 1.000000 .
H7 H 0.465(3) 0.6660(19) 0.511(2) 0.053(6) Uiso 1.000000 .
H8 H 0.148(4) 0.531(2) 0.436(2) 0.057(6) Uiso 1.000000 .
H17 H -0.849(4) 0.003(2) -0.1648(19) 0.055(6) Uiso 1.000000 .
H20 H -0.712(4) 0.200(2) 0.232(2) 0.064(7) Uiso 1.000000 .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O2 0.0433(8) 0.0503(8) 0.0244(6) -0.0073(6) 0.0082(5) 0.0075(6)
N1 0.0388(9) 0.0473(9) 0.0306(8) -0.0027(7) 0.0062(6) 0.0089(7)
O3 0.0537(9) 0.0791(11) 0.0395(8) -0.0058(8) 0.0175(7) 0.0157(8)
O1 0.0522(9) 0.0770(11) 0.0386(8) -0.0118(7) 0.0137(7) 0.0164(7)
C10 0.0393(11) 0.0441(11) 0.0228(9) -0.0013(8) 0.0042(7) 0.0057(8)
F1 0.0913(11) 0.1103(12) 0.0357(7) -0.0169(9) -0.0109(7) 0.0245(8)
C6 0.0411(11) 0.0390(10) 0.0248(9) 0.0003(8) 0.0025(7) 0.0070(8)
C5 0.0392(10) 0.0387(10) 0.0262(9) 0.0028(8) 0.0072(7) 0.0116(8)
F3 0.1001(13) 0.1096(13) 0.0509(9) -0.0621(10) -0.0033(8) -0.0000(8)
C11 0.0395(11) 0.0409(10) 0.0328(10) 0.0020(8) 0.0091(8) 0.0128(8)
C13 0.0368(10) 0.0340(10) 0.0399(10) 0.0003(8) 0.0050(8) 0.0138(8)
C12 0.0358(10) 0.0383(10) 0.0353(10) 0.0018(8) 0.0094(7) 0.0134(8)
C18 0.0382(11) 0.0380(10) 0.0534(12) -0.0004(8) 0.0025(9) 0.0165(9)
C9 0.0370(10) 0.0412(10) 0.0302(9) 0.0035(8) 0.0072(7) 0.0108(8)
C4 0.0413(11) 0.0468(11) 0.0341(10) -0.0039(9) 0.0060(8) 0.0145(9)
C21 0.0427(12) 0.0461(11) 0.0420(11) 0.0044(9) 0.0139(9) 0.0161(9)
C8 0.0478(12) 0.0549(13) 0.0266(9) -0.0000(10) 0.0109(8) 0.0101(9)
F2 0.1160(14) 0.0736(10) 0.0614(10) 0.0046(9) 0.0175(9) -0.0232(8)
C7 0.0479(12) 0.0503(12) 0.0231(9) -0.0032(9) 0.0055(8) 0.0069(8)
C2 0.0448(11) 0.0397(10) 0.0299(9) -0.0011(8) 0.0003(8) 0.0087(8)
C14 0.0492(12) 0.0471(12) 0.0391(11) -0.0080(9) 0.0068(9) 0.0107(9)
C3 0.0423(12) 0.0479(12) 0.0374(11) -0.0087(9) 0.0027(8) 0.0126(9)
C19 0.0373(12) 0.0496(12) 0.0712(15) -0.0051(9) 0.0141(10) 0.0210(11)
C20 0.0460(13) 0.0541(13) 0.0614(14) 0.0030(10) 0.0236(11) 0.0248(11)
C1 0.0640(15) 0.0635(15) 0.0371(12) -0.0194(12) 0.0008(10) 0.0020(11)
C15 0.0675(16) 0.0532(13) 0.0406(12) -0.0061(11) 0.0058(10) 0.0093(10)
C17 0.0454(13) 0.0462(12) 0.0632(15) -0.0079(10) -0.0048(11) 0.0143(11)
C16 0.0679(16) 0.0520(13) 0.0441(13) -0.0097(11) -0.0095(11) 0.0039(11)

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O2 C5 1.379(2) .
O2 C4 1.358(2) .
N1 C11 1.334(2) .
N1 C9 1.401(2) .
O3 H3 0.8200 .
O3 C21 1.279(2) .
O1 C4 1.207(2) .
C10 C5 1.369(3) .
C10 C9 1.390(3) .
C10 H10 0.96(2) .
F1 C1 1.329(3) .
C6 C5 1.403(2) .
C6 C7 1.406(3) .
C6 C2 1.434(3) .
F3 C1 1.326(3) .
C11 C12 1.386(3) .
C11 H11 1.00(2) .
C13 C12 1.457(2) .
C13 C18 1.408(3) .
C13 C14 1.406(3) .
C12 C21 1.446(3) .
C18 C19 1.432(3) .
C18 C17 1.405(3) .
C9 C8 1.406(2) .
C4 C3 1.448(3) .
C21 C20 1.427(3) .
C8 C7 1.361(3) .
C8 H8 0.92(2) .
F2 C1 1.321(3) .
C7 H7 0.97(2) .
C2 C3 1.339(3) .
C2 C1 1.507(3) .
C14 H14 0.9300 .
C14 C15 1.380(3) .
C3 H3a 0.89(2) .
C19 H19 0.9300 .
C19 C20 1.340(3) .
C20 H20 1.01(2) .
C15 C16 1.383(3) .
C15 H15 1.01(2) .
C17 C16 1.367(4) .
C17 H17 0.97(2) .
C16 H16 0.9300 .

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
C4 O2 C5 122.13(14) . .
C9 N1 C11 125.47(16) . .
C21 O3 H3 109.5 . .
C9 C10 C5 118.87(16) . .
H10 C10 C5 119.0(12) . .
H10 C10 C9 122.1(12) . .
C7 C6 C5 116.46(17) . .
C2 C6 C5 117.00(17) . .
C2 C6 C7 126.53(16) . .
C10 C5 O2 115.32(15) . .
C6 C5 O2 121.19(16) . .
C6 C5 C10 123.47(17) . .
C12 C11 N1 122.92(17) . .
H11 C11 N1 116.7(12) . .
H11 C11 C12 120.4(12) . .
C18 C13 C12 119.58(17) . .
C14 C13 C12 122.82(17) . .
C14 C13 C18 117.59(18) . .
C13 C12 C11 121.72(17) . .
C21 C12 C11 119.24(17) . .
C21 C12 C13 119.02(17) . .
C19 C18 C13 118.81(18) . .
C17 C18 C13 120.1(2) . .
C17 C18 C19 121.1(2) . .
C10 C9 N1 123.48(16) . .
C8 C9 N1 117.58(17) . .
C8 C9 C10 118.94(18) . .
O1 C4 O2 117.67(17) . .
C3 C4 O2 117.31(17) . .
C3 C4 O1 125.02(18) . .
C12 C21 O3 122.40(18) . .
C20 C21 O3 119.07(18) . .
C20 C21 C12 118.52(18) . .
C7 C8 C9 121.40(19) . .
H8 C8 C9 114.2(14) . .
H8 C8 C7 124.4(14) . .
C8 C7 C6 120.85(17) . .
H7 C7 C6 120.9(13) . .
H7 C7 C8 118.2(13) . .
C3 C2 C6 120.81(17) . .
C1 C2 C6 120.32(18) . .
C1 C2 C3 118.86(19) . .
H14 C14 C13 119.49(11) . .
C15 C14 C13 121.0(2) . .
C15 C14 H14 119.49(14) . .
C2 C3 C4 121.44(18) . .
H3a C3 C4 115.2(14) . .
H3a C3 C2 123.3(14) . .
H19 C19 C18 118.67(12) . .
C20 C19 C18 122.65(19) . .
C20 C19 H19 118.67(13) . .
C19 C20 C21 121.3(2) . .
H20 C20 C21 115.9(13) . .
H20 C20 C19 122.8(13) . .
F3 C1 F1 106.8(2) . .
F2 C1 F1 106.9(2) . .
F2 C1 F3 107.0(2) . .
C2 C1 F1 112.03(19) . .
C2 C1 F3 112.5(2) . .
C2 C1 F2 111.3(2) . .
C16 C15 C14 120.9(2) . .
H15 C15 C14 118.2(13) . .
H15 C15 C16 120.9(13) . .
C16 C17 C18 120.9(2) . .
H17 C17 C18 115.5(13) . .
H17 C17 C16 123.6(13) . .
C17 C16 C15 119.5(2) . .
H16 C16 C15 120.26(14) . .
H16 C16 C17 120.26(13) . .