# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 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.
#
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#  fide research purposes only. It may contain copyright material
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data_x1747l

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
(Z)-4-(1-Fluoro-2-phenylprop-1-en-1-yl)-1-(3-phenylpropyl)-1H-1,2,3-triazole
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H20 F N3'
_chemical_formula_weight         321.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2/c
_symmetry_space_group_name_Hall  -P2yc

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'

_cell_length_a                   18.306(4)
_cell_length_b                   5.6030(11)
_cell_length_c                   16.578(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.41(3)
_cell_angle_gamma                90.00
_cell_volume                     1666.8(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3804
_cell_measurement_theta_min      2.95
_cell_measurement_theta_max      27.47

_exptl_crystal_description       plate
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5987
_diffrn_reflns_av_R_equivalents  0.0578
_diffrn_reflns_av_sigmaI/netI    0.0920
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.95
_diffrn_reflns_theta_max         27.47
_reflns_number_total             3804
_reflns_number_gt                2290
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0605P)²+0.1339P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0043(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3804
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1243
_refine_ls_R_factor_gt           0.0610
_refine_ls_wR_factor_ref         0.1395
_refine_ls_wR_factor_gt          0.1177
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F F 0.28638(7) 0.3786(2) 0.16325(6) 0.0285(3) Uani 1 1 d . . .
N1 N 0.22856(9) 0.4210(3) -0.08763(9) 0.0219(4) Uani 1 1 d . . .
N2 N 0.23917(10) 0.6587(3) -0.09231(10) 0.0267(4) Uani 1 1 d . . .
N3 N 0.27204(10) 0.7311(3) -0.01837(10) 0.0258(4) Uani 1 1 d . . .
C4 C 0.28228(11) 0.5376(3) 0.03296(12) 0.0216(5) Uani 1 1 d . . .
C5 C 0.25386(11) 0.3408(4) -0.01124(11) 0.0217(5) Uani 1 1 d . . .
H5A H 0.2524 0.1816 0.0081 0.026 Uiso 1 1 calc R . .
C6 C 0.31545(12) 0.5556(4) 0.12079(12) 0.0227(5) Uani 1 1 d . . .
C7 C 0.36379(11) 0.7068(4) 0.16268(11) 0.0221(5) Uani 1 1 d . . .
C8 C 0.19121(12) 0.2910(4) -0.16115(11) 0.0251(5) Uani 1 1 d . . .
H8A H 0.2120 0.1276 -0.1599 0.030 Uiso 1 1 calc R . .
H8B H 0.2015 0.3722 -0.2108 0.030 Uiso 1 1 calc R . .
C9 C 0.10710(12) 0.2759(4) -0.16699(12) 0.0264(5) Uani 1 1 d . . .
H9A H 0.0834 0.2250 -0.2233 0.032 Uiso 1 1 calc R . .
H9B H 0.0879 0.4367 -0.1578 0.032 Uiso 1 1 calc R . .
C10 C 0.08453(12) 0.1023(4) -0.10505(13) 0.0320(6) Uani 1 1 d . . .
H10A H 0.1058 -0.0568 -0.1124 0.038 Uiso 1 1 calc R . .
H10B H 0.1060 0.1577 -0.0486 0.038 Uiso 1 1 calc R . .
C11 C 0.00099(12) 0.0795(4) -0.11416(11) 0.0255(5) Uani 1 1 d . . .
C12 C -0.04002(13) 0.2607(4) -0.08700(12) 0.0300(6) Uani 1 1 d . . .
H12A H -0.0149 0.3981 -0.0618 0.036 Uiso 1 1 calc R . .
C13 C -0.11681(14) 0.2455(4) -0.09586(13) 0.0346(6) Uani 1 1 d . . .
H13A H -0.1437 0.3712 -0.0765 0.041 Uiso 1 1 calc R . .
C14 C -0.15411(13) 0.0484(4) -0.13263(13) 0.0326(6) Uani 1 1 d . . .
H14A H -0.2067 0.0375 -0.1389 0.039 Uiso 1 1 calc R . .
C15 C -0.11481(14) -0.1320(4) -0.16007(14) 0.0369(6) Uani 1 1 d . . .
H15A H -0.1404 -0.2685 -0.1854 0.044 Uiso 1 1 calc R . .
C16 C -0.03775(14) -0.1169(4) -0.15108(14) 0.0345(6) Uani 1 1 d . . .
H16A H -0.0113 -0.2433 -0.1706 0.041 Uiso 1 1 calc R . .
C17 C 0.40084(13) 0.9015(4) 0.12244(12) 0.0283(5) Uani 1 1 d . . .
H17A H 0.3903 0.8778 0.0627 0.042 Uiso 1 1 calc R . .
H17B H 0.4548 0.8962 0.1432 0.042 Uiso 1 1 calc R . .
H17C H 0.3815 1.0571 0.1353 0.042 Uiso 1 1 calc R . .
C21 C 0.38418(11) 0.6915(4) 0.25449(12) 0.0233(5) Uani 1 1 d . . .
C22 C 0.36684(12) 0.8809(4) 0.30216(11) 0.0258(5) Uani 1 1 d . . .
H22A H 0.3430 1.0192 0.2762 0.031 Uiso 1 1 calc R . .
C23 C 0.38436(12) 0.8677(4) 0.38712(12) 0.0308(6) Uani 1 1 d . . .
H23A H 0.3720 0.9965 0.4192 0.037 Uiso 1 1 calc R . .
C24 C 0.41966(12) 0.6686(4) 0.42553(13) 0.0329(6) Uani 1 1 d . . .
H24A H 0.4318 0.6606 0.4839 0.039 Uiso 1 1 calc R . .
C25 C 0.43739(13) 0.4808(4) 0.37875(13) 0.0345(6) Uani 1 1 d . . .
H25A H 0.4617 0.3436 0.4051 0.041 Uiso 1 1 calc R . .
C26 C 0.41987(12) 0.4922(4) 0.29369(12) 0.0298(6) Uani 1 1 d . . .
H26A H 0.4323 0.3628 0.2619 0.036 Uiso 1 1 calc R . .

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
F 0.0312(8) 0.0282(7) 0.0256(6) 0.0023(5) 0.0046(5) -0.0069(6)
N1 0.0220(10) 0.0199(10) 0.0231(9) -0.0016(8) 0.0030(7) -0.0001(8)
N2 0.0303(11) 0.0226(10) 0.0263(10) 0.0003(8) 0.0035(8) -0.0001(8)
N3 0.0293(11) 0.0226(10) 0.0250(10) -0.0016(8) 0.0041(8) 0.0000(8)
C4 0.0209(12) 0.0193(11) 0.0252(11) -0.0010(9) 0.0062(9) 0.0001(9)
C5 0.0214(12) 0.0219(11) 0.0218(10) 0.0032(9) 0.0042(8) 0.0025(10)
C6 0.0234(12) 0.0220(11) 0.0244(11) 0.0033(9) 0.0089(9) 0.0012(10)
C7 0.0202(12) 0.0236(12) 0.0229(10) 0.0005(9) 0.0052(8) 0.0015(9)
C8 0.0266(13) 0.0255(12) 0.0219(10) -0.0014(9) 0.0015(9) 0.0013(10)
C9 0.0238(13) 0.0282(12) 0.0260(11) -0.0008(10) 0.0019(9) 0.0005(10)
C10 0.0260(13) 0.0360(14) 0.0323(12) 0.0077(11) 0.0020(10) -0.0003(11)
C11 0.0258(13) 0.0294(13) 0.0202(10) 0.0086(10) 0.0023(9) 0.0012(10)
C12 0.0337(15) 0.0327(13) 0.0240(11) -0.0054(10) 0.0066(9) -0.0065(11)
C13 0.0364(15) 0.0338(14) 0.0381(13) 0.0033(11) 0.0182(11) 0.0058(12)
C14 0.0253(14) 0.0334(14) 0.0392(13) 0.0125(11) 0.0066(10) 0.0005(11)
C15 0.0361(15) 0.0248(13) 0.0481(15) 0.0019(11) 0.0044(12) -0.0067(11)
C16 0.0329(15) 0.0235(13) 0.0483(14) -0.0011(11) 0.0105(11) 0.0025(11)
C17 0.0285(13) 0.0299(13) 0.0256(11) -0.0026(10) 0.0035(9) -0.0055(10)
C21 0.0187(12) 0.0285(12) 0.0225(10) -0.0003(9) 0.0037(8) -0.0045(10)
C22 0.0249(13) 0.0287(13) 0.0248(11) 0.0004(10) 0.0070(9) 0.0000(10)
C23 0.0275(13) 0.0376(14) 0.0286(12) -0.0055(11) 0.0091(10) -0.0053(11)
C24 0.0251(13) 0.0489(15) 0.0234(11) 0.0034(11) 0.0016(9) -0.0092(12)
C25 0.0315(14) 0.0335(14) 0.0344(13) 0.0055(11) -0.0041(10) -0.0045(11)
C26 0.0299(14) 0.0269(13) 0.0301(12) -0.0030(10) -0.0001(10) -0.0029(10)

_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
F C6 1.382(2) . ?
N1 C5 1.337(2) . ?
N1 N2 1.350(2) . ?
N1 C8 1.468(2) . ?
N2 N3 1.318(2) . ?
N3 C4 1.368(2) . ?
C4 C5 1.369(3) . ?
C4 C6 1.466(3) . ?
C6 C7 1.319(3) . ?
C7 C21 1.496(3) . ?
C7 C17 1.508(3) . ?
C8 C9 1.526(3) . ?
C9 C10 1.529(3) . ?
C10 C11 1.512(3) . ?
C11 C16 1.384(3) . ?
C11 C12 1.390(3) . ?
C12 C13 1.387(3) . ?
C13 C14 1.376(3) . ?
C14 C15 1.370(3) . ?
C15 C16 1.391(3) . ?
C21 C26 1.389(3) . ?
C21 C22 1.396(3) . ?
C22 C23 1.383(3) . ?
C23 C24 1.380(3) . ?
C24 C25 1.383(3) . ?
C25 C26 1.384(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
C5 N1 N2 111.07(16) . . ?
C5 N1 C8 129.54(17) . . ?
N2 N1 C8 119.36(16) . . ?
N3 N2 N1 107.11(15) . . ?
N2 N3 C4 108.41(16) . . ?
N3 C4 C5 108.35(16) . . ?
N3 C4 C6 122.82(17) . . ?
C5 C4 C6 128.77(18) . . ?
N1 C5 C4 105.05(17) . . ?
C7 C6 F 118.59(17) . . ?
C7 C6 C4 132.08(18) . . ?
F C6 C4 109.31(16) . . ?
C6 C7 C21 120.35(18) . . ?
C6 C7 C17 123.04(18) . . ?
C21 C7 C17 116.61(17) . . ?
N1 C8 C9 112.26(16) . . ?
C8 C9 C10 113.33(17) . . ?
C11 C10 C9 112.89(17) . . ?
C16 C11 C12 117.5(2) . . ?
C16 C11 C10 122.1(2) . . ?
C12 C11 C10 120.41(19) . . ?
C13 C12 C11 121.5(2) . . ?
C14 C13 C12 120.0(2) . . ?
C15 C14 C13 119.5(2) . . ?
C14 C15 C16 120.5(2) . . ?
C11 C16 C15 121.0(2) . . ?
C26 C21 C22 119.00(18) . . ?
C26 C21 C7 121.44(18) . . ?
C22 C21 C7 119.56(18) . . ?
C23 C22 C21 120.2(2) . . ?
C24 C23 C22 120.4(2) . . ?
C23 C24 C25 119.8(2) . . ?
C24 C25 C26 120.2(2) . . ?
C25 C26 C21 120.4(2) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.052
_exptl_crystal_recrystallization_method 
'Slow evaporation of a solution in methylene chloride'
_database_code_depnum_ccdc_archive 'CCDC 1028722'
