 
data_2010sl0009a
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C13 H0 F5 N'
_chemical_formula_weight          265.14
 
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, -y, z+1/2'
 'x+1/2, y+1/2, z'
 'x+1/2, -y+1/2, z+1/2'
 
_cell_length_a                    3.6878(3)
_cell_length_b                    48.796(4)
_cell_length_c                    12.4014(12)
_cell_angle_alpha                 90.00
_cell_angle_beta                  98.55
_cell_angle_gamma                 90.00
_cell_volume                      2206.8(3)
_cell_formula_units_Z             8
_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           0.10
_exptl_crystal_size_mid           0.05
_exptl_crystal_size_min           0.02
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.596
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              1040
_exptl_absorpt_coefficient_mu     0.155
_exptl_absorpt_correction_type    ?
_exptl_absorpt_correction_T_min   0.9847
_exptl_absorpt_correction_T_max   0.9969
_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             8377
_diffrn_reflns_av_R_equivalents   0.1302
_diffrn_reflns_av_sigmaI/netI     0.1869
_diffrn_reflns_limit_h_min        -4
_diffrn_reflns_limit_h_max        4
_diffrn_reflns_limit_k_min        -58
_diffrn_reflns_limit_k_max        54
_diffrn_reflns_limit_l_min        -14
_diffrn_reflns_limit_l_max        14
_diffrn_reflns_theta_min          3.01
_diffrn_reflns_theta_max          24.99
_reflns_number_total              3399
_reflns_number_gt                 1837
_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)+(0.0682P)²+0.0000P] 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_abs_structure_details
 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack    0.8(18)
_refine_ls_number_reflns          3399
_refine_ls_number_parameters      343
_refine_ls_number_restraints      2
_refine_ls_R_factor_all           0.1712
_refine_ls_R_factor_gt            0.0863
_refine_ls_wR_factor_ref          0.1939
_refine_ls_wR_factor_gt           0.1547
_refine_ls_goodness_of_fit_ref    1.022
_refine_ls_restrained_S_all       1.022
_refine_ls_shift/su_max           0.030
_refine_ls_shift/su_mean          0.007
 
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 0.8258(14) 0.33134(10) 0.2901(4) 0.0355(14) Uani 1 1 d . . .
F2 F 1.3630(15) 0.40569(11) 0.1829(4) 0.0388(15) Uani 1 1 d . . .
F3 F 0.2477(15) 0.20464(11) 0.3003(4) 0.0436(16) Uani 1 1 d . . .
F4 F 0.8913(15) 0.28591(11) 0.4090(4) 0.0436(16) Uani 1 1 d . . .
F5 F 0.8235(15) 0.15564(11) 0.6047(4) 0.0390(15) Uani 1 1 d . . .
F6 F 1.2242(16) 0.50107(11) 0.1656(5) 0.0463(16) Uani 1 1 d . . .
F7 F 0.7017(16) 0.25098(11) 0.6232(5) 0.0477(16) Uani 1 1 d . . .
F8 F 1.0951(15) 0.45462(11) 0.4874(4) 0.0427(16) Uani 1 1 d . . .
F9 F 0.1792(14) 0.08141(11) 0.4989(4) 0.0419(15) Uani 1 1 d . . .
F10 F 0.1273(15) 0.03595(11) 0.3787(4) 0.0443(16) Uani 1 1 d . . .
N1 N 0.4852(19) 0.15512(16) 0.3826(6) 0.0268(19) Uani 1 1 d . . .
C30 C 0.647(2) 0.2269(2) 0.5664(8) 0.031(3) Uani 1 1 d . . .
C1 C 0.416(2) 0.20390(19) 0.4045(8) 0.032(3) Uani 1 1 d . . .
C2 C 1.221(3) 0.4291(2) 0.3384(8) 0.033(2) Uani 1 1 d . . .
C3 C 0.294(2) 0.05962(18) 0.2272(8) 0.027(2) Uani 1 1 d . . .
H3 H 0.2681 0.0434 0.1846 0.032 Uiso 1 1 calc R . .
N2 N 1.2415(19) 0.40493(16) 0.4054(6) 0.0277(19) Uani 1 1 d . . .
C5 C 1.037(3) 0.3099(2) 0.4557(9) 0.037(3) Uani 1 1 d . . .
C6 C 0.522(2) 0.17875(17) 0.4508(7) 0.022(2) Uani 1 1 d . . .
C7 C 0.361(2) 0.10782(19) 0.3555(7) 0.024(2) Uani 1 1 d . . .
C8 C 1.006(2) 0.33279(18) 0.3930(7) 0.025(2) Uani 1 1 d . . .
C9 C 1.148(2) 0.35725(17) 0.4346(7) 0.019(2) Uani 1 1 d . . .
C10 C 0.430(2) 0.10778(19) 0.2474(8) 0.028(2) Uani 1 1 d . . .
H10 H 0.5011 0.1243 0.2161 0.033 Uiso 1 1 calc R . .
C11 C 0.466(2) 0.2284(2) 0.4593(8) 0.038(3) Uani 1 1 d . . .
H11 H 0.3817 0.2452 0.4264 0.045 Uiso 1 1 calc R . .
C12 C 0.258(3) 0.0829(2) 0.3932(7) 0.031(3) Uani 1 1 d . . .
C13 C 1.288(2) 0.42953(19) 0.2303(7) 0.025(2) Uani 1 1 d . . .
C14 C 1.297(3) 0.4531(2) 0.1703(8) 0.032(2) Uani 1 1 d . . .
H14 H 1.3467 0.4530 0.0974 0.039 Uiso 1 1 calc R . .
C15 C 0.395(2) 0.0839(2) 0.1849(7) 0.027(2) Uani 1 1 d . . .
H15 H 0.4427 0.0844 0.1117 0.032 Uiso 1 1 calc R . .
C16 C 1.331(2) 0.35782(17) 0.5403(7) 0.024(2) Uani 1 1 d . . .
H16 H 1.4392 0.3744 0.5693 0.028 Uiso 1 1 calc R . .
C17 C 1.109(2) 0.3823(2) 0.3663(7) 0.029(2) Uani 1 1 d . . .
H17 H 0.9848 0.3814 0.2935 0.034 Uiso 1 1 calc R . .
C18 C 0.231(3) 0.05959(17) 0.3318(8) 0.028(2) Uani 1 1 d . . .
C19 C 0.695(2) 0.17926(17) 0.5567(7) 0.024(2) Uani 1 1 d . . .
C20 C 1.227(2) 0.47747(18) 0.2236(8) 0.030(3) Uani 1 1 d . . .
C21 C 1.155(3) 0.47855(18) 0.3286(7) 0.029(2) Uani 1 1 d . . .
H21 H 1.1052 0.4954 0.3621 0.035 Uiso 1 1 calc R . .
C22 C 0.764(3) 0.20287(19) 0.6157(8) 0.031(2) Uani 1 1 d . . .
H22 H 0.8882 0.2025 0.6884 0.037 Uiso 1 1 calc R . .
C23 C 0.391(2) 0.1325(2) 0.4216(7) 0.026(2) Uani 1 1 d . . .
H23 H 0.3401 0.1318 0.4944 0.031 Uiso 1 1 calc R . .
C24 C 1.360(3) 0.3344(2) 0.6041(8) 0.035(3) Uani 1 1 d . . .
H24 H 1.4790 0.3353 0.6774 0.042 Uiso 1 1 calc R . .
C25 C 1.158(2) 0.45416(19) 0.3825(7) 0.027(2) Uani 1 1 d . . .
C26 C 1.214(3) 0.3097(2) 0.5615(8) 0.036(3) Uani 1 1 d . . .
H26 H 1.2361 0.2934 0.6038 0.043 Uiso 1 1 calc R . .
 
 
_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 C8 1.350(9) . ?
F2 C13 1.351(10) . ?
F3 C1 1.348(10) . ?
F4 C5 1.378(10) . ?
F5 C19 1.350(10) . ?
F6 C20 1.357(10) . ?
F7 C30 1.371(10) . ?
F8 C25 1.355(10) . ?
F9 C12 1.386(10) . ?
F10 C18 1.372(10) . ?
N1 C23 1.273(11) . ?
N1 C6 1.424(11) . ?
C30 C22 1.361(13) . ?
C30 C11 1.397(13) . ?
C1 C11 1.372(13) . ?
C1 C6 1.387(12) . ?
C2 C25 1.376(13) . ?
C2 C13 1.397(12) . ?
C2 N2 1.437(11) . ?
C3 C18 1.350(12) . ?
C3 C15 1.368(13) . ?
C3 H3 0.9500 . ?
N2 C17 1.276(11) . ?
C5 C8 1.357(13) . ?
C5 C26 1.376(13) . ?
C6 C19 1.372(11) . ?
C7 C12 1.378(12) . ?
C7 C10 1.400(12) . ?
C7 C23 1.452(12) . ?
C8 C9 1.373(12) . ?
C9 C16 1.382(11) . ?
C9 C17 1.480(12) . ?
C10 C15 1.397(13) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C18 1.363(13) . ?
C13 C14 1.374(13) . ?
C14 C20 1.401(13) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C24 1.384(13) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C19 C22 1.368(12) . ?
C20 C21 1.368(12) . ?
C21 C25 1.365(12) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 C26 1.393(14) . ?
C24 H24 0.9500 . ?
C26 H26 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
C23 N1 C6 118.9(8) . . ?
C22 C30 F7 119.7(8) . . ?
C22 C30 C11 123.1(9) . . ?
F7 C30 C11 117.3(9) . . ?
F3 C1 C11 117.3(9) . . ?
F3 C1 C6 118.8(8) . . ?
C11 C1 C6 123.8(9) . . ?
C25 C2 C13 115.6(9) . . ?
C25 C2 N2 119.8(9) . . ?
C13 C2 N2 124.5(9) . . ?
C18 C3 C15 117.7(9) . . ?
C18 C3 H3 121.1 . . ?
C15 C3 H3 121.1 . . ?
C17 N2 C2 120.5(8) . . ?
C8 C5 F4 117.6(9) . . ?
C8 C5 C26 122.6(9) . . ?
F4 C5 C26 119.7(9) . . ?
C19 C6 C1 116.3(8) . . ?
C19 C6 N1 124.9(8) . . ?
C1 C6 N1 118.3(8) . . ?
C12 C7 C10 115.0(9) . . ?
C12 C7 C23 122.9(9) . . ?
C10 C7 C23 122.2(8) . . ?
F1 C8 C5 119.1(8) . . ?
F1 C8 C9 120.5(8) . . ?
C5 C8 C9 120.3(8) . . ?
C8 C9 C16 118.7(8) . . ?
C8 C9 C17 120.1(8) . . ?
C16 C9 C17 121.2(8) . . ?
C15 C10 C7 121.2(9) . . ?
C15 C10 H10 119.4 . . ?
C7 C10 H10 119.4 . . ?
C1 C11 C30 115.8(10) . . ?
C1 C11 H11 122.1 . . ?
C30 C11 H11 122.1 . . ?
C18 C12 C7 123.2(9) . . ?
C18 C12 F9 118.5(9) . . ?
C7 C12 F9 118.3(9) . . ?
F2 C13 C14 117.6(8) . . ?
F2 C13 C2 118.7(8) . . ?
C14 C13 C2 123.7(9) . . ?
C13 C14 C20 115.8(10) . . ?
C13 C14 H14 122.1 . . ?
C20 C14 H14 122.1 . . ?
C3 C15 C10 121.1(9) . . ?
C3 C15 H15 119.4 . . ?
C10 C15 H15 119.4 . . ?
C24 C16 C9 120.7(8) . . ?
C24 C16 H16 119.7 . . ?
C9 C16 H16 119.7 . . ?
N2 C17 C9 119.9(8) . . ?
N2 C17 H17 120.1 . . ?
C9 C17 H17 120.1 . . ?
C3 C18 C12 121.8(9) . . ?
C3 C18 F10 120.5(8) . . ?
C12 C18 F10 117.7(9) . . ?
F5 C19 C6 119.3(8) . . ?
F5 C19 C22 117.3(8) . . ?
C6 C19 C22 123.3(8) . . ?
F6 C20 C21 119.0(8) . . ?
F6 C20 C14 117.2(9) . . ?
C21 C20 C14 123.8(9) . . ?
C20 C21 C25 116.4(8) . . ?
C20 C21 H21 121.8 . . ?
C25 C21 H21 121.8 . . ?
C30 C22 C19 117.7(8) . . ?
C30 C22 H22 121.2 . . ?
C19 C22 H22 121.2 . . ?
N1 C23 C7 120.5(9) . . ?
N1 C23 H23 119.8 . . ?
C7 C23 H23 119.8 . . ?
C16 C24 C26 120.4(10) . . ?
C16 C24 H24 119.8 . . ?
C26 C24 H24 119.8 . . ?
F8 C25 C21 117.8(8) . . ?
F8 C25 C2 117.4(8) . . ?
C21 C25 C2 124.8(8) . . ?
C5 C26 C24 117.3(10) . . ?
C5 C26 H26 121.4 . . ?
C24 C26 H26 121.4 . . ?
 
_diffrn_measured_fraction_theta_max    0.985
_diffrn_reflns_theta_full              24.99
_diffrn_measured_fraction_theta_full   0.985
_refine_diff_density_max    0.344
_refine_diff_density_min   -0.408
_refine_diff_density_rms    0.088
