 
data_2010sl0004a
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C13 H0 F3 N'
_chemical_formula_weight          227.14
 
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            ?
_symmetry_space_group_name_H-M    ?
 
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                    12.8476(8)
_cell_length_b                    3.7474(2)
_cell_length_c                    21.5262(14)
_cell_angle_alpha                 90.00
_cell_angle_beta                  97.291(3)
_cell_angle_gamma                 90.00
_cell_volume                      1028.00(11)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     ?
_cell_measurement_theta_min       ?
_cell_measurement_theta_max       ?
 
_exptl_crystal_description        ?
_exptl_crystal_colour             ?
_exptl_crystal_size_max           0.60
_exptl_crystal_size_mid           0.04
_exptl_crystal_size_min           0.03
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.468
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              448
_exptl_absorpt_coefficient_mu     0.126
_exptl_absorpt_correction_type    ?
_exptl_absorpt_correction_T_min   0.9283
_exptl_absorpt_correction_T_max   0.9962
_exptl_absorpt_process_details    ?
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       120(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   ?
_diffrn_measurement_method        ?
_diffrn_detector_area_resol_mean  ?
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             11809
_diffrn_reflns_av_R_equivalents   0.0722
_diffrn_reflns_av_sigmaI/netI     0.0532
_diffrn_reflns_limit_h_min        -15
_diffrn_reflns_limit_h_max        15
_diffrn_reflns_limit_k_min        -4
_diffrn_reflns_limit_k_max        4
_diffrn_reflns_limit_l_min        -25
_diffrn_reflns_limit_l_max        25
_diffrn_reflns_theta_min          3.10
_diffrn_reflns_theta_max          24.99
_reflns_number_total              1815
_reflns_number_gt                 1473
_reflns_threshold_expression      >2σ(I)
 
_computing_data_collection        ?
_computing_cell_refinement        ?
_computing_data_reduction         ?
_computing_structure_solution     ?
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
 
_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 > 2σ(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)+(0.0799P)²+0.1884P] where P=(Fo²+2Fc²)/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          1815
_refine_ls_number_parameters      154
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0668
_refine_ls_R_factor_gt            0.0493
_refine_ls_wR_factor_ref          0.1327
_refine_ls_wR_factor_gt           0.1216
_refine_ls_goodness_of_fit_ref    1.032
_refine_ls_restrained_S_all       1.032
_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
F1 F 0.83948(9) 0.8281(3) 0.22699(5) 0.0341(4) Uani 1 1 d . . .
F2 F 0.89117(10) 0.2714(3) 0.00055(6) 0.0379(4) Uani 1 1 d . . .
F3 F 0.18205(9) 1.0362(4) 0.15964(6) 0.0368(4) Uani 1 1 d . . .
N1 N 0.57854(13) 0.7365(4) 0.09897(8) 0.0258(4) Uani 1 1 d . . .
C1 C 0.35162(16) 0.8065(6) 0.19042(9) 0.0276(5) Uani 1 1 d . . .
H1 H 0.3324 0.7466 0.2303 0.033 Uiso 1 1 calc R . .
C2 C 0.77825(16) 0.5021(5) 0.06832(10) 0.0259(5) Uani 1 1 d . . .
H2 H 0.7203 0.4671 0.0368 0.031 Uiso 1 1 calc R . .
C3 C 0.40441(16) 0.9789(5) 0.07291(10) 0.0264(5) Uani 1 1 d . . .
H3 H 0.4220 1.0343 0.0325 0.032 Uiso 1 1 calc R . .
C4 C 0.47914(15) 0.8220(5) 0.11710(9) 0.0237(5) Uani 1 1 d . . .
C5 C 0.45127(16) 0.7347(6) 0.17602(10) 0.0264(5) Uani 1 1 d . . .
H5 H 0.5013 0.6251 0.2064 0.032 Uiso 1 1 calc R . .
C6 C 0.85157(16) 0.6873(5) 0.17002(9) 0.0257(5) Uani 1 1 d . . .
C7 C 0.28090(15) 0.9665(6) 0.14573(10) 0.0259(5) Uani 1 1 d . . .
C8 C 0.30522(16) 1.0546(5) 0.08719(10) 0.0263(5) Uani 1 1 d . . .
H8 H 0.2547 1.1652 0.0573 0.032 Uiso 1 1 calc R . .
C9 C 0.87738(16) 0.4105(6) 0.05739(10) 0.0279(5) Uani 1 1 d . . .
C10 C 0.76286(15) 0.6480(5) 0.12635(9) 0.0243(5) Uani 1 1 d . . .
C11 C 0.65905(16) 0.7577(5) 0.14017(10) 0.0254(5) Uani 1 1 d . . .
H11 H 0.6513 0.8467 0.1807 0.030 Uiso 1 1 calc R . .
C12 C 0.95096(16) 0.5935(6) 0.15900(10) 0.0303(5) Uani 1 1 d . . .
H12 H 1.0091 0.6255 0.1905 0.036 Uiso 1 1 calc R . .
C13 C 0.96491(16) 0.4515(6) 0.10124(10) 0.0306(5) Uani 1 1 d . . .
H13 H 1.0326 0.3843 0.0920 0.037 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
F1 0.0334(7) 0.0466(8) 0.0207(7) -0.0047(5) -0.0032(5) -0.0037(6)
F2 0.0366(8) 0.0510(9) 0.0268(8) -0.0054(6) 0.0069(6) 0.0016(6)
F3 0.0254(7) 0.0557(9) 0.0290(7) -0.0006(6) 0.0029(5) 0.0042(6)
N1 0.0251(10) 0.0305(10) 0.0208(10) 0.0005(7) -0.0010(8) 0.0009(7)
C1 0.0297(12) 0.0342(12) 0.0181(11) -0.0002(9) -0.0006(9) -0.0028(9)
C2 0.0290(12) 0.0272(11) 0.0199(11) 0.0035(8) -0.0036(9) -0.0003(9)
C3 0.0296(12) 0.0318(12) 0.0169(11) 0.0004(8) -0.0008(9) -0.0006(9)
C4 0.0252(11) 0.0248(11) 0.0200(11) -0.0028(8) -0.0019(9) -0.0012(8)
C5 0.0261(11) 0.0304(11) 0.0206(11) 0.0024(8) -0.0047(9) 0.0009(8)
C6 0.0309(12) 0.0288(11) 0.0163(11) 0.0026(8) -0.0013(9) -0.0012(9)
C7 0.0211(11) 0.0316(12) 0.0249(12) -0.0016(9) 0.0025(9) 0.0001(8)
C8 0.0256(11) 0.0285(11) 0.0225(11) 0.0009(9) -0.0059(9) 0.0022(8)
C9 0.0325(12) 0.0302(11) 0.0207(11) 0.0021(9) 0.0026(9) 0.0015(9)
C10 0.0244(11) 0.0262(11) 0.0213(11) 0.0028(8) -0.0009(9) -0.0009(8)
C11 0.0305(12) 0.0264(11) 0.0187(11) 0.0011(8) 0.0015(9) -0.0021(9)
C12 0.0254(12) 0.0371(12) 0.0262(12) 0.0074(9) -0.0055(9) -0.0029(9)
C13 0.0255(12) 0.0365(13) 0.0300(13) 0.0079(9) 0.0039(9) 0.0015(9)
 
_geom_special_details
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 C6 1.362(2) . ?
F2 C9 1.362(2) . ?
F3 C7 1.366(2) . ?
N1 C11 1.277(3) . ?
N1 C4 1.418(3) . ?
C1 C7 1.374(3) . ?
C1 C5 1.381(3) . ?
C1 H1 0.9500 . ?
C2 C9 1.368(3) . ?
C2 C10 1.400(3) . ?
C2 H2 0.9500 . ?
C3 C8 1.378(3) . ?
C3 C4 1.393(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.400(3) . ?
C5 H5 0.9500 . ?
C6 C12 1.374(3) . ?
C6 C10 1.390(3) . ?
C7 C8 1.376(3) . ?
C8 H8 0.9500 . ?
C9 C13 1.382(3) . ?
C10 C11 1.462(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.385(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
 
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 N1 C4 118.24(17) . . ?
C7 C1 C5 118.49(19) . . ?
C7 C1 H1 120.8 . . ?
C5 C1 H1 120.8 . . ?
C9 C2 C10 119.43(18) . . ?
C9 C2 H2 120.3 . . ?
C10 C2 H2 120.3 . . ?
C8 C3 C4 120.77(19) . . ?
C8 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C3 C4 C5 118.94(18) . . ?
C3 C4 N1 118.30(18) . . ?
C5 C4 N1 122.63(18) . . ?
C1 C5 C4 120.59(18) . . ?
C1 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
F1 C6 C12 117.99(18) . . ?
F1 C6 C10 118.20(18) . . ?
C12 C6 C10 123.81(19) . . ?
F3 C7 C1 118.70(18) . . ?
F3 C7 C8 118.69(18) . . ?
C1 C7 C8 122.60(19) . . ?
C7 C8 C3 118.59(19) . . ?
C7 C8 H8 120.7 . . ?
C3 C8 H8 120.7 . . ?
F2 C9 C2 118.73(18) . . ?
F2 C9 C13 117.95(18) . . ?
C2 C9 C13 123.32(19) . . ?
C6 C10 C2 116.63(18) . . ?
C6 C10 C11 121.57(19) . . ?
C2 C10 C11 121.80(18) . . ?
N1 C11 C10 121.39(19) . . ?
N1 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C6 C12 C13 118.84(19) . . ?
C6 C12 H12 120.6 . . ?
C13 C12 H12 120.6 . . ?
C9 C13 C12 117.98(19) . . ?
C9 C13 H13 121.0 . . ?
C12 C13 H13 121.0 . . ?
 
_diffrn_measured_fraction_theta_max    0.998
_diffrn_reflns_theta_full              24.99
_diffrn_measured_fraction_theta_full   0.998
_refine_diff_density_max    0.167
_refine_diff_density_min   -0.260
_refine_diff_density_rms    0.054
