 
data_2009src0464p21n
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C10 H6 F N3 O'
_chemical_formula_weight          203.18
 
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                    8.1049(2)
_cell_length_b                    6.1023(2)
_cell_length_c                    17.6777(5)
_cell_angle_alpha                 90.00
_cell_angle_beta                  92.219(2)
_cell_angle_gamma                 90.00
_cell_volume                      873.66(4)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     20507
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        block
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.24
_exptl_crystal_size_mid           0.13
_exptl_crystal_size_min           0.06
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.545
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              416
_exptl_absorpt_coefficient_mu     0.120
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9718
_exptl_absorpt_correction_T_max   0.9929
_exptl_absorpt_process_details    'SADABS 2007/2 (Sheldrick, G.M., 2007)' 
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature           120(2)
_diffrn_radiation_wavelength           0.71073
_diffrn_radiation_type                      MoK\a
_diffrn_radiation_source                  'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator    'graphite'
_diffrn_measurement_device_type   
'Bruker-Nonius Roper CCD camera on κ-goniostat'
_diffrn_measurement_method          'φ & ω scans'
_diffrn_detector_area_resol_mean   '9.091'
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             18331
_diffrn_reflns_av_R_equivalents   0.0443
_diffrn_reflns_av_sigmaI/netI     0.0274
_diffrn_reflns_limit_h_min        -10
_diffrn_reflns_limit_h_max        10
_diffrn_reflns_limit_k_min        -7
_diffrn_reflns_limit_k_max        7
_diffrn_reflns_limit_l_min        -22
_diffrn_reflns_limit_l_max        22
_diffrn_reflns_theta_min          3.53
_diffrn_reflns_theta_max          27.48
_reflns_number_total              1992
_reflns_number_gt                 1732
_reflns_threshold_expression      >2σ(I)
 
_computing_data_collection        
'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction
_computing_data_reduction         
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'  
_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)+(0.0518P)²+0.3947P] 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          1992
_refine_ls_number_parameters      144
_refine_ls_number_restraints      2
_refine_ls_R_factor_all           0.0466
_refine_ls_R_factor_gt            0.0396
_refine_ls_wR_factor_ref          0.1023
_refine_ls_wR_factor_gt           0.0969
_refine_ls_goodness_of_fit_ref    1.023
_refine_ls_restrained_S_all       1.023
_refine_ls_shift/su_max           0.001
_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
C1 C 0.46683(16) 0.2430(2) 0.29382(8) 0.0223(3) Uani 1 1 d . . .
C2 C 0.52866(16) 0.4506(2) 0.28216(8) 0.0233(3) Uani 1 1 d . . .
H2 H 0.4666 0.5565 0.2538 0.028 Uiso 1 1 calc R . .
C3 C 0.68449(15) 0.5001(2) 0.31313(7) 0.0199(3) Uani 1 1 d . . .
H3 H 0.7298 0.6419 0.3062 0.024 Uiso 1 1 calc R . .
C4 C 0.77475(15) 0.3424(2) 0.35438(7) 0.0170(3) Uani 1 1 d . . .
C5 C 0.70772(16) 0.1342(2) 0.36502(7) 0.0201(3) Uani 1 1 d . . .
H5 H 0.7690 0.0271 0.3932 0.024 Uiso 1 1 calc R . .
C6 C 0.55181(16) 0.0833(2) 0.33462(7) 0.0220(3) Uani 1 1 d . . .
H6 H 0.5050 -0.0576 0.3417 0.026 Uiso 1 1 calc R . .
C7 C 0.93902(15) 0.3934(2) 0.38628(7) 0.0160(3) Uani 1 1 d . . .
C9 C 1.13884(15) 0.6167(2) 0.42251(7) 0.0172(3) Uani 1 1 d . . .
C10 C 1.17973(15) 0.4036(2) 0.44022(7) 0.0171(3) Uani 1 1 d . . .
C13 C 1.32221(15) 0.3235(2) 0.47980(7) 0.0184(3) Uani 1 1 d . . .
N11 N 1.04983(12) 0.26385(18) 0.41574(6) 0.0177(2) Uani 1 1 d . . .
N12 N 1.21154(14) 0.81027(19) 0.43043(7) 0.0228(3) Uani 1 1 d D . .
N14 N 1.43622(14) 0.25444(19) 0.51281(7) 0.0241(3) Uani 1 1 d . . .
O8 O 0.98481(10) 0.61249(14) 0.38784(5) 0.0179(2) Uani 1 1 d . . .
F1 F 0.31517(10) 0.19319(16) 0.26324(5) 0.0337(2) Uani 1 1 d . . .
H12A H 1.1511(19) 0.929(3) 0.4228(9) 0.030(4) Uiso 1 1 d D . .
H12B H 1.311(2) 0.814(3) 0.4520(10) 0.042(5) Uiso 1 1 d D . .
 
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
C1 0.0130(6) 0.0272(7) 0.0265(7) -0.0039(5) -0.0017(5) -0.0034(5)
C2 0.0174(6) 0.0238(7) 0.0285(7) 0.0016(5) -0.0036(5) 0.0017(5)
C3 0.0180(6) 0.0173(6) 0.0244(6) -0.0001(5) -0.0004(5) -0.0006(5)
C4 0.0157(6) 0.0168(6) 0.0185(6) -0.0019(5) -0.0009(4) 0.0007(5)
C5 0.0208(6) 0.0179(6) 0.0214(6) 0.0006(5) -0.0010(5) -0.0010(5)
C6 0.0204(6) 0.0200(7) 0.0256(7) -0.0009(5) 0.0016(5) -0.0051(5)
C7 0.0157(6) 0.0120(6) 0.0203(6) -0.0002(4) -0.0005(4) -0.0012(4)
C9 0.0147(6) 0.0178(6) 0.0189(6) 0.0004(5) -0.0022(4) -0.0001(5)
C10 0.0154(6) 0.0141(6) 0.0215(6) 0.0004(5) -0.0024(5) -0.0003(5)
C13 0.0195(6) 0.0120(6) 0.0235(6) 0.0000(5) -0.0009(5) -0.0016(5)
N11 0.0160(5) 0.0144(5) 0.0224(5) -0.0004(4) -0.0028(4) -0.0004(4)
N12 0.0179(6) 0.0150(6) 0.0349(6) 0.0015(5) -0.0078(5) -0.0008(4)
N14 0.0217(6) 0.0174(6) 0.0327(6) 0.0023(5) -0.0061(5) -0.0004(4)
O8 0.0154(4) 0.0142(5) 0.0236(5) 0.0012(3) -0.0038(3) -0.0008(3)
F1 0.0162(4) 0.0385(5) 0.0456(5) -0.0002(4) -0.0092(4) -0.0077(4)
 
_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
C1 F1 1.3579(15) . ?
C1 C6 1.380(2) . ?
C1 C2 1.381(2) . ?
C2 C3 1.3901(18) . ?
C2 H2 0.9500 . ?
C3 C4 1.3966(18) . ?
C3 H3 0.9500 . ?
C4 C5 1.3975(18) . ?
C4 C7 1.4592(17) . ?
C5 C6 1.3891(18) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 N11 1.2909(16) . ?
C7 O8 1.3875(15) . ?
C9 N12 1.3253(17) . ?
C9 O8 1.3695(15) . ?
C9 C10 1.3746(18) . ?
C10 N11 1.4100(16) . ?
C10 C13 1.4141(17) . ?
C13 N14 1.1534(17) . ?
N12 H12A 0.882(14) . ?
N12 H12B 0.879(15) . ?
 
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
F1 C1 C6 118.41(12) . . ?
F1 C1 C2 118.29(12) . . ?
C6 C1 C2 123.30(12) . . ?
C1 C2 C3 118.03(13) . . ?
C1 C2 H2 121.0 . . ?
C3 C2 H2 121.0 . . ?
C2 C3 C4 120.37(12) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C5 119.86(11) . . ?
C3 C4 C7 120.44(12) . . ?
C5 C4 C7 119.69(11) . . ?
C6 C5 C4 120.26(12) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C1 C6 C5 118.18(12) . . ?
C1 C6 H6 120.9 . . ?
C5 C6 H6 120.9 . . ?
N11 C7 O8 113.62(10) . . ?
N11 C7 C4 129.46(12) . . ?
O8 C7 C4 116.89(10) . . ?
N12 C9 O8 117.24(11) . . ?
N12 C9 C10 135.79(12) . . ?
O8 C9 C10 106.97(10) . . ?
C9 C10 N11 109.37(11) . . ?
C9 C10 C13 128.66(12) . . ?
N11 C10 C13 121.90(11) . . ?
N14 C13 C10 178.42(14) . . ?
C7 N11 C10 104.64(11) . . ?
C9 N12 H12A 118.3(11) . . ?
C9 N12 H12B 117.6(13) . . ?
H12A N12 H12B 122.8(18) . . ?
C9 O8 C7 105.38(9) . . ?
 
loop_
 _geom_hbond_atom_site_label_D
 _geom_hbond_atom_site_label_H
 _geom_hbond_atom_site_label_A
 _geom_hbond_distance_DH
 _geom_hbond_distance_HA
 _geom_hbond_distance_DA
 _geom_hbond_angle_DHA
 _geom_hbond_site_symmetry_A
N12 H12A N11  0.882(14) 2.204(15) 3.0692(16) 166.8(15) 1_565
N12 H12B N14  0.879(15) 2.157(16) 3.0151(16) 164.9(18) 3_866
 
_diffrn_measured_fraction_theta_max    0.997
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.997
_refine_diff_density_max    0.228
_refine_diff_density_min   -0.258
_refine_diff_density_rms    0.052
