# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2012


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#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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# 
#  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_1187ajm
_database_code_depnum_ccdc_archive 'CCDC 870088'
#TrackingRef '1187ajm.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H22 F N3 O2'
_chemical_formula_weight         391.44

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'
O O 0.0106 0.0060 '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   P21/n

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

_cell_length_a                   11.966(2)
_cell_length_b                   10.7644(19)
_cell_length_c                   17.134(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.503(3)
_cell_angle_gamma                90.00
_cell_volume                     2104.7(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2656
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      27.94

_exptl_crystal_description       BLOCKS
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             824
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_process_details   'BRUKER SADABS'
_exptl_absorpt_correction_T_min  0.9705
_exptl_absorpt_correction_T_max  0.9906

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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 SMART APEX CCD DIFFRACTOMETER'
_diffrn_measurement_method       'OMEGA-PHI SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9371
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_sigmaI/netI    0.0433
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.84
_diffrn_reflns_theta_max         24.00
_reflns_number_total             3306
_reflns_number_gt                2904
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'BRUKER SMART'
_computing_cell_refinement       'BRUKER SMART'
_computing_data_reduction        'BRUKER SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0503P)^2^+2.4303P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3306
_refine_ls_number_parameters     272
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1192
_refine_ls_R_factor_gt           0.1050
_refine_ls_wR_factor_ref         0.2080
_refine_ls_wR_factor_gt          0.2015
_refine_ls_goodness_of_fit_ref   1.343
_refine_ls_restrained_S_all      1.343
_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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N3 N 0.5379(3) 0.9891(3) 0.1719(3) 0.0465(10) Uani 1 d . . .
H3C H 0.531(3) 1.010(3) 0.124(3) 0.030(11) Uiso 1 d . . .
H3D H 0.542(4) 1.050(5) 0.210(3) 0.066(16) Uiso 1 d . . .
O2 O 0.2252(3) 0.6206(3) 0.33041(19) 0.0570(9) Uani 1 d . . .
N1 N 0.4686(3) 0.8635(3) 0.25782(18) 0.0386(8) Uani 1 d . . .
C12 C 0.5442(4) 0.9322(4) 0.3253(2) 0.0411(10) Uani 1 d . . .
C9 C 0.3907(4) 0.7766(3) 0.2726(2) 0.0384(10) Uani 1 d . . .
O1 O 0.3486(3) 0.6520(3) 0.45516(18) 0.0736(11) Uani 1 d . . .
C19 C 0.3121(4) 0.6686(4) 0.3738(3) 0.0455(11) Uani 1 d . . .
C7 C 0.3733(4) 0.6857(4) 0.1361(2) 0.0404(10) Uani 1 d . . .
H7 H 0.3142 0.6617 0.0850 0.049 Uiso 1 calc R . .
C8 C 0.3082(4) 0.7188(4) 0.1984(2) 0.0394(10) Uani 1 d . . .
H8 H 0.2791 0.6413 0.2153 0.047 Uiso 1 calc R . .
C18 C 0.3916(4) 0.7526(4) 0.3500(2) 0.0434(11) Uani 1 d . . .
H18 H 0.4478 0.7931 0.3918 0.052 Uiso 1 calc R . .
C23 C 0.4398(4) 0.8274(4) 0.0398(3) 0.0509(12) Uani 1 d . . .
C10 C 0.4773(4) 0.8858(4) 0.1795(2) 0.0373(10) Uani 1 d . . .
C6 C 0.4543(4) 0.5759(4) 0.1642(2) 0.0392(10) Uani 1 d . . .
F1 F 0.6596(3) 0.2668(3) 0.2458(2) 0.1003(12) Uani 1 d . . .
C11 C 0.4325(4) 0.8025(4) 0.1191(2) 0.0420(10) Uani 1 d . . .
C17 C 0.6553(4) 0.8911(4) 0.3630(3) 0.0540(12) Uani 1 d . . .
H17 H 0.6809 0.8166 0.3470 0.065 Uiso 1 calc R . .
C5 C 0.4071(4) 0.4568(4) 0.1581(3) 0.0521(12) Uani 1 d . . .
H5 H 0.3266 0.4469 0.1355 0.062 Uiso 1 calc R . .
C13 C 0.5060(4) 1.0405(4) 0.3513(3) 0.0561(13) Uani 1 d . . .
H13 H 0.4298 1.0677 0.3265 0.067 Uiso 1 calc R . .
C1 C 0.5726(4) 0.5865(4) 0.1993(3) 0.0547(12) Uani 1 d . . .
H1A H 0.6071 0.6647 0.2039 0.066 Uiso 1 calc R . .
N2 N 0.4448(5) 0.8491(4) -0.0246(3) 0.0780(14) Uani 1 d . . .
C2 C 0.6427(5) 0.4831(5) 0.2284(3) 0.0645(14) Uani 1 d . . .
H2 H 0.7228 0.4917 0.2537 0.077 Uiso 1 calc R . .
C3 C 0.5910(5) 0.3688(5) 0.2190(3) 0.0638(14) Uani 1 d . . .
C16 C 0.7299(5) 0.9611(6) 0.4255(3) 0.0681(15) Uani 1 d . . .
H16 H 0.8062 0.9344 0.4506 0.082 Uiso 1 calc R . .
C4 C 0.4758(5) 0.3530(4) 0.1844(3) 0.0680(15) Uani 1 d . . .
H4 H 0.4428 0.2740 0.1782 0.082 Uiso 1 calc R . .
C15 C 0.6906(6) 1.0696(6) 0.4498(3) 0.0777(17) Uani 1 d . . .
H15 H 0.7405 1.1164 0.4916 0.093 Uiso 1 calc R . .
C14 C 0.5795(6) 1.1093(5) 0.4136(3) 0.0796(18) Uani 1 d . . .
H14 H 0.5530 1.1826 0.4308 0.095 Uiso 1 calc R . .
C20 C 0.2788(6) 0.5732(6) 0.4910(3) 0.092(2) Uani 1 d . . .
H20A H 0.2235 0.6236 0.5084 0.111 Uiso 1 calc R . .
H20B H 0.2350 0.5142 0.4505 0.111 Uiso 1 calc R . .
C22 C 0.2035(4) 0.8034(4) 0.1624(3) 0.0554(12) Uani 1 d . . .
H22A H 0.1584 0.8100 0.2001 0.083 Uiso 1 calc R . .
H22B H 0.1554 0.7692 0.1117 0.083 Uiso 1 calc R . .
H22C H 0.2305 0.8843 0.1529 0.083 Uiso 1 calc R . .
C21 C 0.3540(9) 0.5081(11) 0.5597(5) 0.211(7) Uani 1 d . . .
H21A H 0.4125 0.4635 0.5431 0.317 Uiso 1 calc R . .
H21B H 0.3085 0.4506 0.5804 0.317 Uiso 1 calc R . .
H21C H 0.3915 0.5665 0.6018 0.317 Uiso 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
N3 0.065(3) 0.041(2) 0.038(2) 0.0073(19) 0.022(2) -0.0086(19)
O2 0.060(2) 0.062(2) 0.0532(19) 0.0042(16) 0.0222(17) -0.0148(18)
N1 0.050(2) 0.0327(18) 0.0340(18) 0.0016(14) 0.0135(16) -0.0072(16)
C12 0.044(3) 0.041(2) 0.039(2) 0.0039(19) 0.012(2) -0.007(2)
C9 0.048(3) 0.028(2) 0.043(2) 0.0016(18) 0.020(2) 0.0040(19)
O1 0.108(3) 0.080(2) 0.0394(18) -0.0079(16) 0.0317(18) -0.049(2)
C19 0.060(3) 0.039(2) 0.041(2) -0.012(2) 0.021(2) -0.006(2)
C7 0.050(3) 0.041(2) 0.027(2) -0.0049(18) 0.0067(18) -0.006(2)
C8 0.048(3) 0.034(2) 0.039(2) 0.0041(18) 0.016(2) -0.004(2)
C18 0.058(3) 0.037(2) 0.040(2) -0.0046(19) 0.022(2) -0.013(2)
C23 0.069(3) 0.042(3) 0.045(3) -0.001(2) 0.021(2) -0.006(2)
C10 0.045(3) 0.033(2) 0.038(2) 0.0086(18) 0.0184(19) 0.0044(19)
C6 0.047(3) 0.043(2) 0.031(2) -0.0104(18) 0.0168(19) -0.008(2)
F1 0.104(3) 0.071(2) 0.134(3) 0.024(2) 0.048(2) 0.036(2)
C11 0.053(3) 0.040(2) 0.035(2) -0.0007(19) 0.016(2) -0.003(2)
C17 0.059(3) 0.054(3) 0.049(3) 0.009(2) 0.017(2) 0.004(2)
C5 0.051(3) 0.045(3) 0.060(3) -0.007(2) 0.018(2) -0.008(2)
C13 0.060(3) 0.045(3) 0.053(3) -0.010(2) 0.002(2) -0.001(2)
C1 0.056(3) 0.047(3) 0.066(3) -0.013(2) 0.026(3) -0.008(2)
N2 0.128(4) 0.067(3) 0.050(3) 0.000(2) 0.044(3) -0.018(3)
C2 0.047(3) 0.070(4) 0.077(4) -0.011(3) 0.021(3) 0.009(3)
C3 0.073(4) 0.047(3) 0.077(4) 0.002(3) 0.031(3) 0.013(3)
C16 0.057(3) 0.091(4) 0.045(3) 0.011(3) -0.003(3) -0.007(3)
C4 0.079(4) 0.039(3) 0.093(4) 0.003(3) 0.035(3) 0.000(3)
C15 0.090(5) 0.079(4) 0.048(3) -0.008(3) -0.004(3) -0.019(4)
C14 0.100(5) 0.060(3) 0.063(3) -0.018(3) 0.002(3) -0.001(3)
C20 0.156(6) 0.077(4) 0.066(4) -0.011(3) 0.066(4) -0.051(4)
C22 0.052(3) 0.051(3) 0.062(3) 0.002(2) 0.015(2) 0.001(2)
C21 0.225(11) 0.271(13) 0.104(6) 0.100(8) 0.000(7) -0.129(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
N3 C10 1.354(5) . ?
N3 H3C 0.83(4) . ?
N3 H3D 0.92(5) . ?
O2 C19 1.198(5) . ?
N1 C9 1.397(5) . ?
N1 C10 1.398(5) . ?
N1 C12 1.440(5) . ?
C12 C17 1.365(6) . ?
C12 C13 1.374(6) . ?
C9 C18 1.347(5) . ?
C9 C8 1.492(5) . ?
O1 C19 1.342(5) . ?
O1 C20 1.449(6) . ?
C19 C18 1.457(6) . ?
C7 C6 1.513(6) . ?
C7 C11 1.514(6) . ?
C7 C8 1.541(5) . ?
C7 H7 0.9800 . ?
C8 C22 1.521(6) . ?
C8 H8 0.9800 . ?
C18 H18 0.9300 . ?
C23 N2 1.146(5) . ?
C23 C11 1.413(6) . ?
C10 C11 1.353(5) . ?
C6 C1 1.366(6) . ?
C6 C5 1.392(6) . ?
F1 C3 1.364(5) . ?
C17 C16 1.391(7) . ?
C17 H17 0.9300 . ?
C5 C4 1.381(7) . ?
C5 H5 0.9300 . ?
C13 C14 1.377(6) . ?
C13 H13 0.9300 . ?
C1 C2 1.393(7) . ?
C1 H1A 0.9300 . ?
C2 C3 1.364(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.338(7) . ?
C16 C15 1.370(8) . ?
C16 H16 0.9300 . ?
C4 H4 0.9300 . ?
C15 C14 1.356(8) . ?
C15 H15 0.9300 . ?
C14 H14 0.9300 . ?
C20 C21 1.432(10) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 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
C10 N3 H3C 115(3) . . ?
C10 N3 H3D 116(3) . . ?
H3C N3 H3D 119(4) . . ?
C9 N1 C10 122.4(3) . . ?
C9 N1 C12 119.4(3) . . ?
C10 N1 C12 118.2(3) . . ?
C17 C12 C13 119.5(4) . . ?
C17 C12 N1 120.0(4) . . ?
C13 C12 N1 120.4(4) . . ?
C18 C9 N1 120.0(4) . . ?
C18 C9 C8 124.5(4) . . ?
N1 C9 C8 115.6(3) . . ?
C19 O1 C20 117.9(4) . . ?
O2 C19 O1 122.5(4) . . ?
O2 C19 C18 127.7(4) . . ?
O1 C19 C18 109.7(4) . . ?
C6 C7 C11 114.7(4) . . ?
C6 C7 C8 111.7(3) . . ?
C11 C7 C8 107.7(3) . . ?
C6 C7 H7 107.5 . . ?
C11 C7 H7 107.5 . . ?
C8 C7 H7 107.5 . . ?
C9 C8 C22 110.4(3) . . ?
C9 C8 C7 110.1(3) . . ?
C22 C8 C7 112.6(3) . . ?
C9 C8 H8 107.8 . . ?
C22 C8 H8 107.8 . . ?
C7 C8 H8 107.8 . . ?
C9 C18 C19 125.6(4) . . ?
C9 C18 H18 117.2 . . ?
C19 C18 H18 117.2 . . ?
N2 C23 C11 179.1(5) . . ?
C11 C10 N3 124.9(4) . . ?
C11 C10 N1 119.6(3) . . ?
N3 C10 N1 115.4(4) . . ?
C1 C6 C5 117.0(4) . . ?
C1 C6 C7 123.7(4) . . ?
C5 C6 C7 119.2(4) . . ?
C10 C11 C23 119.0(4) . . ?
C10 C11 C7 120.3(3) . . ?
C23 C11 C7 120.7(4) . . ?
C12 C17 C16 119.8(5) . . ?
C12 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C4 C5 C6 122.2(5) . . ?
C4 C5 H5 118.9 . . ?
C6 C5 H5 118.9 . . ?
C12 C13 C14 120.7(5) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C6 C1 C2 121.5(4) . . ?
C6 C1 H1A 119.2 . . ?
C2 C1 H1A 119.2 . . ?
C3 C2 C1 118.4(5) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C4 C3 F1 118.8(5) . . ?
C4 C3 C2 122.5(5) . . ?
F1 C3 C2 118.7(5) . . ?
C15 C16 C17 119.7(5) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
C3 C4 C5 118.3(5) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 H4 120.8 . . ?
C14 C15 C16 120.6(5) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C15 C14 C13 119.7(5) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C21 C20 O1 109.6(6) . . ?
C21 C20 H20A 109.8 . . ?
O1 C20 H20A 109.8 . . ?
C21 C20 H20B 109.8 . . ?
O1 C20 H20B 109.8 . . ?
H20A C20 H20B 108.2 . . ?
C8 C22 H22A 109.5 . . ?
C8 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C8 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.942
_diffrn_reflns_theta_full        24.00
_diffrn_measured_fraction_theta_full 0.942
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.048