Electronic Supplementary Material for CrystEngComm
This journal is (c) The Royal Society of Chemistry 2007

data_global
_journal_name_full               CrystEngComm

#===============================================================================

# 2. PROCESSING SUMMARY (JOURNAL OFFICE ONLY)

_journal_coden_Cambridge         1350
#==============================================================================

# 0. AUDIT DETAILS

_audit_creation_date             'Jan 21 14:33:58 2005'
_audit_creation_method           'PLATON <TABLE ACC> option'
_audit_update_record             
;
?
;

#===============================================================================

# 1. SUBMISSION DETAILS

_publ_contact_author_name        'Tayur Guru Row'
_publ_contact_author_address     # address of author for correspondence
;
Indian Institute of Science
Bangalore
Karnataka
560012
INDIA
;

_publ_contact_author_email       SSCTNG@SSCU.IISC.ERNET.IN
_journal_year                    ?
_journal_volume                  ?
_journal_issue                   ?
_journal_page_first              ?
_journal_page_last               ?

#===============================================================================

# 3. TITLE AND AUTHOR LIST

_publ_section_title              
;
Evaluation of Interchangeability of C-H and C-F
groups: Insights from Crystal Packing in a series of isomeric
Fluorinated Benzanilides.
;
_publ_section_title_footnote     
;
?
;

#===============================================================================

# 4. TEXT

_publ_section_synopsis           
;
?
;
_publ_section_abstract           
;
?
;

# Insert blank lines between paragraphs

_publ_section_comment            
;
?
;
_publ_section_exptl_prep         
;
?
;
_publ_section_exptl_refinement   
;
?
;

# Insert blank lines between references

_publ_section_references         
;
Allen, F.H. & Kennard, O. (1993).
Chem. Des. Autom. News., 8, 31-37.

Altomare, A., Burla, M.C., Camalli, M., Cascarano, G.L., Giacovazzo, C.
Guagliardi, A., Moliterni, A.G.G., Polidori, G. & Spagna, R.
(1999) J. Appl. Cryst. 32, 115-119.

Beurskens, P.T., Admiraal, G., Beurskens, G., Bosman, W.P.,
Garc\'ia-Granda, S., Gould, R.O., Smits, J.M.M. &
Smykalla, C. (1999) The DIRDIF99 program system,
Technical Report of the Crystallography Laboratory,
University of Nijmegen, The Netherlands.

Boer, J.L. de & Duisenberg, A.J.M. (1984). Acta Cryst. A40, C-410.

Boeyens, J.C.A. (1978). J.Cryst.Mol.Struct. 8, 317-320.

Cremer, D. & Pople, J.A. (1975). J. Am. Chem. Soc. 97, 1354-1358.

Enraf-Nonius (1989). CAD-4 Software. Version 5. Enraf-Nonius, Delft,
The Netherlands.

Flack, H.D. (1983). Acta Cryst. A39, 876-881.

LePage, Y. (1987). J. Appl. Cryst. 20, 264-269.

Mackay, A.L. (1984). Acta Cryst. A40, 165-166.

Meulenaer, J. de & Tompa, H. (1965). Acta Cryst. 19, 1014-1018.

Nonius (1998). Collect Software, Nonius, Delft, The Netherlands.

North, A.C.T., Phillips, D.C. & Mathews, F.S. (1968).
Acta Cryst. A24, 351-359.

Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, 276, 307-326.

Sheldrick, G.M. SHELXL93. Program for crystal structure
refinement. University of G\\"ottingen, Germany, 1993.

Sheldrick, G.M. SHELXL97. Program for crystal structure
refinement. University of G\\"ottingen, Germany, 1997.

Sheldrick, G.M. SHELXS86. Program for Crystal Structure
solution. University of G\\"ottingen, Germany, 1986.

Sheldrick, G.M. SHELXS97. Program for Crystal Structure
solution. University of G\\"ottingen, Germany, 1997.

Spek, A.L. (1987). Acta Cryst. C43, 1233-1235.

Spek, A.L. (1988). J. Appl. Cryst. 21, 578-579.

Spek, A.L. (1990). Acta Cryst. A46, C-34.

Spek, A.L. (1997). HELENA, Program for Datareduction, Utrecht
University, The Netherlands.

Spek, A.L. (1994). Am. Crystallogr. Assoc.-Abstracts, 22, 66.

Wilson, A.J.C. (1992) Ed. International Tables for Crystallography,
Volume C, Kluwer Academic Publishers, Dordrecht, The Netherlands.
;

_publ_section_acknowledgements   
; ?
;
_publ_section_figure_captions    
; View of the title compound with the atom numbering scheme.
Displacement ellipsoids for non-H atoms are drawn at the 50% probability level.
;
loop_
_publ_author_name
'Tayur Guru Row'
'Deepak Chopra'

data_dc4_2n_m
_database_code_depnum_ccdc_archive 'CCDC 285374'

#===============================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
;
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H9 F N O'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural     ?
_chemical_formula_sum            'C13 H9 F N O'
_chemical_formula_iupac          ?
_chemical_formula_weight         214.21
_chemical_compound_source        ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_Int_Tables_number      14

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,1/2-z
3 -x,-y,-z
4 x,1/2-y,1/2+z

_cell_length_a                   8.0355(18)
_cell_length_b                   5.3598(12)
_cell_length_c                   23.640(5)
_cell_angle_alpha                90
_cell_angle_beta                 90.074(4)
_cell_angle_gamma                90
_cell_volume                     1018.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    935
_cell_measurement_theta_min      1.4
_cell_measurement_theta_max      27.4
_cell_special_details            
;
;

_exptl_crystal_description       block
_exptl_crystal_colour            ' colorless'

_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.09
_exptl_crystal_size_rad          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             444
_exptl_absorpt_coefficient_mu    0.102
_exptl_crystal_density_meas_temp ?

# Permitted for _exptl_absorpt_correction_type :
# analytical 'analytical from crystal shape'
# Example: de Meulenaer&Tompa: ABST
# cylinder 'cylindrical'
# gaussian 'Gaussian from crystal shape'
# Example: PLATON/ABSG
# integration 'integration from crystal shape'
# multi-scan 'symmetry-related measurements'
# Example: SADABS, MULABS
# none 'no absorption corr. applied'
# numerical 'numerical from crystal shape'
# psi-scan 'psi-scan corrections'
# Example: PLATON/ABSP
# refdelf 'refined from delta-F'
# Example: SHELXA, DIFABS, DELABS
# sphere 'spherical'
# Example: PLATON/ABSS
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min  0.9415
_exptl_absorpt_correction_T_max  0.9910

#===============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
;
;
_diffrn_ambient_temperature      290(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 area detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?

# number of measured reflections (redundant set)
_diffrn_reflns_number            6666
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_sigmaI/netI    0.0222
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.72
_diffrn_reflns_theta_max         25.00
_diffrn_measured_fraction_theta_max 0.977
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.977
_diffrn_reflns_reduction_process 
;
;

_reflns_number_total             1761
_reflns_number_gt                1523
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 1998)'
_computing_cell_refinement       SMART
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)'
_computing_publication_material  'PLATON (Spek, 2003)'

#===============================================================================

# 8. REFINEMENT DATA

_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^)+(0.0551P)^2^+0.4798P] 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         1761
_refine_ls_number_parameters     168
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0706
_refine_ls_R_factor_gt           0.0605
_refine_ls_wR_factor_ref         0.1417
_refine_ls_wR_factor_gt          0.1361
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_restrained_S_all      1.132
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.041

#===============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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
C13 C 0.2604(3) 0.4083(6) 1.01651(14) 0.0394(9) Uani 0.824(9) 1 d P A 1
N1 N 0.2321(3) 0.2088(5) 0.98143(11) 0.0401(10) Uani 0.824(9) 1 d P A 1
F1 F 0.2888(2) 0.6224(4) 1.21326(7) 0.0633(6) Uani 0.806(4) 1 d P B 1
F1A F 0.2090(13) 0.5300(19) 0.7899(4) 0.095(4) Uani 0.194(4) 1 d P B 2
N1A N 0.2714(17) 0.210(3) 1.0228(8) 0.068(6) Uiso 0.176(9) 1 d P A 2
C13A C 0.240(2) 0.389(4) 0.9857(9) 0.057(5) Uiso 0.176(9) 1 d P A 2
O1 O 0.2439(2) 0.6226(3) 1.00083(6) 0.0621(6) Uani 1 1 d . . .
C9 C 0.1830(3) 0.4007(5) 0.83131(10) 0.0523(6) Uani 1 1 d . . .
C3 C 0.3253(3) 0.4582(4) 1.17149(9) 0.0470(6) Uani 1 1 d . . .
C12 C 0.0865(3) 0.0311(5) 0.90450(11) 0.0547(7) Uani 1 1 d . A .
H12 H 0.0533 -0.0950 0.9290 0.066 Uiso 1 1 calc R . .
C6 C 0.4093(3) 0.1261(5) 1.08941(11) 0.0566(7) Uani 1 1 d . . .
H6 H 0.4376 0.0115 1.0615 0.068 Uiso 1 1 calc R A 2
C4 C 0.4187(3) 0.2564(5) 1.18642(10) 0.0545(7) Uani 1 1 d . A .
H4 H 0.4527 0.2325 1.2237 0.065 Uiso 1 1 calc R . .
C2 C 0.2736(3) 0.5013(5) 1.11738(9) 0.0483(6) Uani 1 1 d . A .
H2 H 0.2110 0.6423 1.1088 0.058 Uiso 1 1 calc R . .
C11 C 0.0409(3) 0.0220(5) 0.84887(12) 0.0608(7) Uani 1 1 d . . .
H11 H -0.0233 -0.1104 0.8358 0.073 Uiso 1 1 calc R B .
C8 C 0.2299(3) 0.4155(4) 0.88747(10) 0.0503(6) Uani 1 1 d . A .
H8 H 0.2926 0.5498 0.9004 0.060 Uiso 1 1 calc R . .
C10 C 0.0889(3) 0.2057(5) 0.81211(10) 0.0570(7) Uani 1 1 d . B .
H10 H 0.0575 0.1980 0.7743 0.068 Uiso 1 1 calc R . .
C7 C 0.1817(3) 0.2264(5) 0.92452(9) 0.0465(6) Uani 1 1 d . . .
C5 C 0.4616(3) 0.0882(5) 1.14455(12) 0.0607(7) Uani 1 1 d . A .
H5 H 0.5257 -0.0508 1.1535 0.073 Uiso 1 1 calc R . .
C1 C 0.3152(3) 0.3336(5) 1.07564(10) 0.0482(6) Uani 1 1 d . A .
H1N H 0.239(3) 0.066(6) 0.9966(12) 0.058(8) Uiso 1 1 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
C13 0.0476(16) 0.0333(18) 0.0373(18) 0.0037(13) -0.0002(12) 0.0020(11)
N1 0.0526(14) 0.0315(18) 0.0362(15) 0.0022(10) -0.0050(10) -0.0002(10)
F1 0.0813(13) 0.0705(12) 0.0381(10) -0.0124(8) -0.0055(8) 0.0030(10)
F1A 0.111(8) 0.080(7) 0.094(7) 0.021(5) 0.015(6) -0.010(6)
O1 0.1086(16) 0.0331(10) 0.0445(10) 0.0024(7) -0.0131(9) 0.0038(9)
C9 0.0629(16) 0.0519(15) 0.0420(13) 0.0042(12) 0.0011(11) 0.0097(12)
C3 0.0547(14) 0.0491(14) 0.0374(12) -0.0027(10) -0.0035(10) -0.0080(11)
C12 0.0499(14) 0.0473(14) 0.0670(17) 0.0113(12) 0.0022(12) -0.0016(11)
C6 0.0568(15) 0.0542(15) 0.0587(16) -0.0126(12) 0.0051(12) -0.0064(12)
C4 0.0549(15) 0.0632(16) 0.0455(13) 0.0113(12) -0.0113(11) -0.0082(12)
C2 0.0498(14) 0.0526(14) 0.0426(13) 0.0052(11) -0.0040(10) 0.0041(11)
C11 0.0616(16) 0.0515(15) 0.0691(18) -0.0114(13) -0.0125(13) -0.0008(12)
C8 0.0550(14) 0.0466(13) 0.0492(14) -0.0059(11) 0.0011(11) -0.0065(11)
C10 0.0610(16) 0.0653(17) 0.0447(13) -0.0070(12) -0.0099(11) 0.0118(13)
C7 0.0421(12) 0.0607(15) 0.0367(12) 0.0023(11) 0.0002(9) 0.0082(11)
C5 0.0530(15) 0.0484(15) 0.0807(19) 0.0150(14) -0.0040(13) 0.0057(12)
C1 0.0411(12) 0.0604(15) 0.0429(13) -0.0007(11) -0.0028(10) -0.0054(11)

#===============================================================================

# 10. MOLECULAR GEOMETRY

_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
C13 O1 1.214(3) . ?
C13 N1 1.372(5) . ?
C13 C1 1.519(4) . ?
N1 C7 1.407(3) . ?
N1 H1N 0.85(3) . ?
F1 C3 1.355(3) . ?
F1A C9 1.217(9) . ?
N1A C13A 1.32(3) . ?
N1A C1 1.456(18) . ?
N1A C6 1.976(18) . ?
N1A H1N 1.02(3) . ?
C13A O1 1.30(2) . ?
C9 C10 1.368(4) . ?
C9 C8 1.382(3) . ?
C3 C4 1.363(3) . ?
C3 C2 1.364(3) . ?
C12 C11 1.365(4) . ?
C12 C7 1.380(3) . ?
C12 H12 0.9300 . ?
C6 C1 1.384(4) . ?
C6 C5 1.384(4) . ?
C6 H6 0.9300 . ?
C4 C5 1.383(4) . ?
C4 H4 0.9300 . ?
C2 C1 1.376(3) . ?
C2 H2 0.9300 . ?
C11 C10 1.369(4) . ?
C11 H11 0.9300 . ?
C8 C7 1.395(3) . ?
C8 H8 0.9300 . ?
C10 H10 0.9300 . ?
C5 H5 0.9300 . ?

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
O1 C13 N1 122.3(3) . . ?
O1 C13 C1 124.2(3) . . ?
N1 C13 C1 113.5(2) . . ?
C13 N1 C7 125.0(3) . . ?
C13 N1 H1N 116.0(18) . . ?
C7 N1 H1N 118.9(19) . . ?
C13A N1A C1 106.7(16) . . ?
C13A N1A C6 143.1(15) . . ?
C13A N1A H1N 95(2) . . ?
C1 N1A H1N 157(2) . . ?
C6 N1A H1N 117(2) . . ?
O1 C13A N1A 121(2) . . ?
O1 C13A C7 135.2(16) . . ?
N1A C13A C7 103.9(16) . . ?
F1A C9 C10 105.3(6) . . ?
F1A C9 C8 133.9(6) . . ?
C10 C9 C8 120.8(2) . . ?
F1 C3 C4 116.5(2) . . ?
F1 C3 C2 120.5(2) . . ?
C4 C3 C2 123.0(2) . . ?
C11 C12 C7 120.4(2) . . ?
C11 C12 H12 119.8 . . ?
C7 C12 H12 119.8 . . ?
C1 C6 C5 120.3(2) . . ?
C1 C6 N1A 47.4(5) . . ?
C5 C6 N1A 162.3(5) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
N1A C6 H6 73.9 . . ?
C3 C4 C5 118.0(2) . . ?
C3 C4 H4 121.0 . . ?
C5 C4 H4 121.0 . . ?
C3 C2 C1 119.2(2) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C12 C11 C10 120.7(2) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C9 C8 C7 119.1(2) . . ?
C9 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
C9 C10 C11 119.7(2) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C12 C7 C8 119.3(2) . . ?
C12 C7 N1 115.8(2) . . ?
C8 C7 N1 124.7(2) . . ?
C12 C7 C13A 143.9(7) . . ?
C4 C5 C6 120.2(2) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C2 C1 C6 119.3(2) . . ?
C2 C1 C13 114.7(2) . . ?
C6 C1 C13 125.9(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C13 N1 C7 0.0(4) . . . . ?
C1 C13 N1 C7 -179.4(2) . . . . ?
C1 N1A C13A O1 -3.3(19) . . . . ?
C6 N1A C13A O1 -36(3) . . . . ?
C1 N1A C13A C7 -178.0(8) . . . . ?
C6 N1A C13A C7 149.6(16) . . . . ?
N1 C13 O1 C13A -3.9(13) . . . . ?
C1 C13 O1 C13A 175.4(15) . . . . ?
N1A C13A O1 C13 -0.5(8) . . . . ?
C7 C13A O1 C13 172(3) . . . . ?
C13A N1A C6 C1 47(2) . . . . ?
C13A N1A C6 C5 98(2) . . . . ?
C1 N1A C6 C5 51.0(19) . . . . ?
F1 C3 C4 C5 -178.5(2) . . . . ?
C2 C3 C4 C5 -0.4(4) . . . . ?
F1 C3 C2 C1 178.8(2) . . . . ?
C4 C3 C2 C1 0.7(4) . . . . ?
C7 C12 C11 C10 0.1(4) . . . . ?
F1A C9 C8 C7 -177.9(7) . . . . ?
C10 C9 C8 C7 0.9(4) . . . . ?
F1A C9 C10 C11 178.8(6) . . . . ?
C8 C9 C10 C11 -0.3(4) . . . . ?
C12 C11 C10 C9 -0.1(4) . . . . ?
C11 C12 C7 C8 0.5(4) . . . . ?
C11 C12 C7 N1 -175.5(2) . . . . ?
C11 C12 C7 C13A 159.4(11) . . . . ?
C9 C8 C7 C12 -1.0(3) . . . . ?
C9 C8 C7 N1 174.7(2) . . . . ?
C9 C8 C7 C13A -168.7(6) . . . . ?
C13 N1 C7 C12 -150.2(2) . . . . ?
C13 N1 C7 C8 33.9(4) . . . . ?
C13 N1 C7 C13A 3.0(10) . . . . ?
O1 C13A C7 C12 -129.3(15) . . . . ?
N1A C13A C7 C12 44.3(17) . . . . ?
O1 C13A C7 C8 32.4(17) . . . . ?
N1A C13A C7 C8 -154.1(10) . . . . ?
O1 C13A C7 N1 -173(2) . . . . ?
N1A C13A C7 N1 0.8(6) . . . . ?
C3 C4 C5 C6 -0.3(4) . . . . ?
C1 C6 C5 C4 0.6(4) . . . . ?
N1A C6 C5 C4 -40.9(18) . . . . ?
C3 C2 C1 C6 -0.4(3) . . . . ?
C3 C2 C1 N1A 147.5(13) . . . . ?
C3 C2 C1 C13 -176.4(2) . . . . ?
C5 C6 C1 C2 -0.3(4) . . . . ?
N1A C6 C1 C2 163.9(6) . . . . ?
C5 C6 C1 N1A -164.2(6) . . . . ?
C5 C6 C1 C13 175.3(2) . . . . ?
N1A C6 C1 C13 -20.6(6) . . . . ?
C13A N1A C1 C2 55.0(18) . . . . ?
C6 N1A C1 C2 -152.4(12) . . . . ?
C13A N1A C1 C6 -152.6(11) . . . . ?
C13A N1A C1 C13 2.3(8) . . . . ?
C6 N1A C1 C13 155.0(6) . . . . ?
O1 C13 C1 C2 28.6(4) . . . . ?
N1 C13 C1 C2 -152.0(2) . . . . ?
O1 C13 C1 C6 -147.1(3) . . . . ?
N1 C13 C1 C6 32.3(3) . . . . ?
O1 C13 C1 N1A -178.6(9) . . . . ?
N1 C13 C1 N1A 0.8(8) . . . . ?

data_dc5_32_m
_database_code_depnum_ccdc_archive 'CCDC 285375'

#===============================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
; ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H10 F N O'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural     ?
_chemical_formula_sum            'C13 H10 F N O'
_chemical_formula_iupac          ?
_chemical_formula_weight         215.22
_chemical_compound_source        'see text'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_symmetry_Int_Tables_number      2

loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z

_cell_length_a                   5.3691(10)
_cell_length_b                   7.8623(15)
_cell_length_c                   12.892(2)
_cell_angle_alpha                72.465(3)
_cell_angle_beta                 80.495(3)
_cell_angle_gamma                89.707(3)
_cell_volume                     511.24(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    780
_cell_measurement_theta_min      1.4
_cell_measurement_theta_max      25.8
_cell_special_details            
; ?
;

_exptl_crystal_description       'plates '
_exptl_crystal_colour            colorless

_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08
_exptl_crystal_size_rad          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             224
_exptl_absorpt_coefficient_mu    0.101
_exptl_crystal_density_meas_temp ?

# Permitted for _exptl_absorpt_correction_type :
# analytical 'analytical from crystal shape'
# Example: de Meulenaer&Tompa: ABST
# cylinder 'cylindrical'
# gaussian 'Gaussian from crystal shape'
# Example: PLATON/ABSG
# integration 'integration from crystal shape'
# multi-scan 'symmetry-related measurements'
# Example: SADABS, MULABS
# none 'no absorption corr. applied'
# numerical 'numerical from crystal shape'
# psi-scan 'psi-scan corrections'
# Example: PLATON/ABSP
# refdelf 'refined from delta-F'
# Example: SHELXA, DIFABS, DELABS
# sphere 'spherical'
# Example: PLATON/ABSS
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min  0.9423
_exptl_absorpt_correction_T_max  0.9919

#===============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
; ?
;
_diffrn_ambient_temperature      290(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 area detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?

# number of measured reflections (redundant set)
_diffrn_reflns_number            3399
_diffrn_reflns_av_R_equivalents  0.0146
_diffrn_reflns_av_sigmaI/netI    0.0286
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.72
_diffrn_reflns_theta_max         25.00
_diffrn_measured_fraction_theta_max 0.972
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.972
_diffrn_reflns_reduction_process 
; ?
;

_reflns_number_total             1768
_reflns_number_gt                1619
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 1998)'
_computing_cell_refinement       SMART
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)'
_computing_publication_material  'PLATON (Spek, 2003)'

#===============================================================================

# 8. REFINEMENT DATA

_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^)+(0.0295P)^2^+0.2526P] 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         1768
_refine_ls_number_parameters     185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0711
_refine_ls_R_factor_gt           0.0626
_refine_ls_wR_factor_ref         0.1201
_refine_ls_wR_factor_gt          0.1165
_refine_ls_goodness_of_fit_ref   1.244
_refine_ls_restrained_S_all      1.244
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.035

#===============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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
N1 N 0.1863(4) 0.2431(3) 0.53071(17) 0.0388(5) Uani 1 1 d . . .
F1 F -0.0081(3) 0.2216(2) 0.96847(13) 0.0669(5) Uani 1 1 d . . .
C12 C -0.0669(4) 0.3160(3) 0.6825(2) 0.0388(6) Uani 1 1 d . . .
C9 C 0.2522(5) 0.1468(4) 0.8251(2) 0.0443(7) Uani 1 1 d . . .
C8 C 0.3043(4) 0.1523(3) 0.7154(2) 0.0397(6) Uani 1 1 d . . .
C6 C 0.2095(4) 0.1850(3) 0.3160(2) 0.0406(6) Uani 1 1 d . . .
C7 C 0.1459(4) 0.2380(3) 0.64325(19) 0.0354(6) Uani 1 1 d . . .
C11 C -0.1191(5) 0.3104(4) 0.7916(2) 0.0430(6) Uani 1 1 d . . .
C10 C 0.0411(5) 0.2262(3) 0.8610(2) 0.0427(6) Uani 1 1 d . . .
C2 C 0.6081(4) 0.3487(3) 0.2679(2) 0.0406(6) Uani 1 1 d . . .
O1 O 0.6144(3) 0.2533(3) 0.49813(15) 0.0557(6) Uani 1 1 d . . .
C3 C 0.6164(5) 0.3594(4) 0.1595(2) 0.0452(7) Uani 1 1 d . . .
C1 C 0.4043(4) 0.2625(3) 0.34782(19) 0.0332(5) Uani 1 1 d . . .
C5 C 0.2197(5) 0.1940(4) 0.2068(2) 0.0437(6) Uani 1 1 d . . .
C13 C 0.4134(4) 0.2513(3) 0.4650(2) 0.0382(6) Uani 1 1 d . . .
C4 C 0.4223(5) 0.2816(4) 0.1282(2) 0.0443(6) Uani 1 1 d . . .
H4 H 0.441(4) 0.284(3) 0.049(2) 0.037(6) Uiso 1 1 d . . .
H12 H -0.170(4) 0.375(3) 0.631(2) 0.040(7) Uiso 1 1 d . . .
H9 H 0.356(5) 0.089(3) 0.877(2) 0.045(7) Uiso 1 1 d . . .
H5 H 0.087(5) 0.145(4) 0.181(2) 0.058(8) Uiso 1 1 d . . .
H11 H -0.260(5) 0.365(4) 0.821(2) 0.060(8) Uiso 1 1 d . . .
H6 H 0.069(5) 0.122(3) 0.369(2) 0.045(7) Uiso 1 1 d . . .
H3 H 0.756(5) 0.419(4) 0.102(2) 0.058(8) Uiso 1 1 d . . .
H8 H 0.448(5) 0.099(3) 0.689(2) 0.045(7) Uiso 1 1 d . . .
H2 H 0.739(5) 0.403(4) 0.292(2) 0.061(8) Uiso 1 1 d . . .
H1N H 0.052(5) 0.256(3) 0.499(2) 0.044(7) Uiso 1 1 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
N1 0.0329(11) 0.0482(13) 0.0373(12) -0.0144(10) -0.0096(9) 0.0040(9)
F1 0.0745(11) 0.0900(13) 0.0391(10) -0.0276(9) -0.0028(8) 0.0034(10)
C12 0.0353(12) 0.0417(15) 0.0419(16) -0.0144(12) -0.0108(11) 0.0043(11)
C9 0.0412(14) 0.0485(17) 0.0419(16) -0.0087(13) -0.0128(12) 0.0011(12)
C8 0.0345(13) 0.0442(16) 0.0407(15) -0.0149(12) -0.0034(11) 0.0045(11)
C6 0.0351(13) 0.0423(15) 0.0435(16) -0.0132(12) -0.0043(11) 0.0005(11)
C7 0.0347(12) 0.0361(14) 0.0345(14) -0.0099(11) -0.0051(10) -0.0026(10)
C11 0.0376(13) 0.0495(17) 0.0459(16) -0.0218(13) -0.0044(12) 0.0042(12)
C10 0.0493(14) 0.0471(16) 0.0319(14) -0.0157(12) 0.0001(11) -0.0068(12)
C2 0.0344(13) 0.0468(16) 0.0415(16) -0.0144(12) -0.0073(11) 0.0017(11)
O1 0.0312(9) 0.0940(16) 0.0440(12) -0.0235(10) -0.0074(8) -0.0022(9)
C3 0.0425(14) 0.0521(17) 0.0385(16) -0.0130(13) -0.0016(12) 0.0047(12)
C1 0.0374(12) 0.0316(13) 0.0323(13) -0.0103(10) -0.0096(10) 0.0081(10)
C5 0.0432(14) 0.0508(17) 0.0460(17) -0.0236(13) -0.0154(12) 0.0053(12)
C13 0.0343(13) 0.0398(14) 0.0418(15) -0.0131(12) -0.0089(11) 0.0018(10)
C4 0.0497(15) 0.0523(17) 0.0343(15) -0.0166(13) -0.0107(12) 0.0117(12)

#===============================================================================

# 10. MOLECULAR GEOMETRY

_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
N1 C13 1.355(3) . ?
N1 C7 1.419(3) . ?
N1 H1N 0.88(3) . ?
F1 C10 1.357(3) . ?
C12 C11 1.375(4) . ?
C12 C7 1.388(3) . ?
C12 H12 0.94(2) . ?
C9 C10 1.372(4) . ?
C9 C8 1.384(4) . ?
C9 H9 0.95(3) . ?
C8 C7 1.386(3) . ?
C8 H8 0.94(2) . ?
C6 C5 1.380(4) . ?
C6 C1 1.390(3) . ?
C6 H6 0.95(3) . ?
C11 C10 1.367(4) . ?
C11 H11 0.95(3) . ?
C2 C3 1.367(4) . ?
C2 C1 1.390(3) . ?
C2 H2 0.96(3) . ?
O1 C13 1.226(3) . ?
C3 C4 1.384(4) . ?
C3 H3 0.97(3) . ?
C1 C13 1.495(3) . ?
C5 C4 1.381(4) . ?
C5 H5 0.96(3) . ?
C4 H4 1.01(2) . ?

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
C13 N1 C7 126.2(2) . . ?
C13 N1 H1N 117.2(17) . . ?
C7 N1 H1N 116.1(16) . . ?
C11 C12 C7 120.5(2) . . ?
C11 C12 H12 121.8(15) . . ?
C7 C12 H12 117.7(15) . . ?
C10 C9 C8 118.9(3) . . ?
C10 C9 H9 118.7(15) . . ?
C8 C9 H9 122.3(15) . . ?
C9 C8 C7 120.1(2) . . ?
C9 C8 H8 120.4(15) . . ?
C7 C8 H8 119.4(15) . . ?
C5 C6 C1 120.2(2) . . ?
C5 C6 H6 118.5(15) . . ?
C1 C6 H6 121.3(15) . . ?
C8 C7 C12 119.4(2) . . ?
C8 C7 N1 122.5(2) . . ?
C12 C7 N1 118.1(2) . . ?
C10 C11 C12 119.1(2) . . ?
C10 C11 H11 118.1(17) . . ?
C12 C11 H11 122.9(17) . . ?
F1 C10 C11 119.3(2) . . ?
F1 C10 C9 118.7(2) . . ?
C11 C10 C9 122.0(2) . . ?
C3 C2 C1 120.8(2) . . ?
C3 C2 H2 122.3(17) . . ?
C1 C2 H2 116.8(17) . . ?
C2 C3 C4 120.1(3) . . ?
C2 C3 H3 122.3(17) . . ?
C4 C3 H3 117.6(16) . . ?
C6 C1 C2 118.9(2) . . ?
C6 C1 C13 123.5(2) . . ?
C2 C1 C13 117.6(2) . . ?
C6 C5 C4 120.2(3) . . ?
C6 C5 H5 122.6(16) . . ?
C4 C5 H5 117.2(16) . . ?
O1 C13 N1 122.5(2) . . ?
O1 C13 C1 121.8(2) . . ?
N1 C13 C1 115.7(2) . . ?
C5 C4 C3 119.7(3) . . ?
C5 C4 H4 122.2(13) . . ?
C3 C4 H4 118.0(13) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 C9 C8 C7 0.5(4) . . . . ?
C9 C8 C7 C12 -0.9(4) . . . . ?
C9 C8 C7 N1 -178.1(2) . . . . ?
C11 C12 C7 C8 0.7(4) . . . . ?
C11 C12 C7 N1 178.1(2) . . . . ?
C13 N1 C7 C8 -34.3(4) . . . . ?
C13 N1 C7 C12 148.4(2) . . . . ?
C7 C12 C11 C10 -0.2(4) . . . . ?
C12 C11 C10 F1 179.4(2) . . . . ?
C12 C11 C10 C9 -0.1(4) . . . . ?
C8 C9 C10 F1 -179.5(2) . . . . ?
C8 C9 C10 C11 0.0(4) . . . . ?
C1 C2 C3 C4 -1.0(4) . . . . ?
C5 C6 C1 C2 0.0(4) . . . . ?
C5 C6 C1 C13 -177.0(2) . . . . ?
C3 C2 C1 C6 0.8(4) . . . . ?
C3 C2 C1 C13 178.0(2) . . . . ?
C1 C6 C5 C4 -0.7(4) . . . . ?
C7 N1 C13 O1 0.8(4) . . . . ?
C7 N1 C13 C1 -177.7(2) . . . . ?
C6 C1 C13 O1 150.2(3) . . . . ?
C2 C1 C13 O1 -26.9(4) . . . . ?
C6 C1 C13 N1 -31.3(3) . . . . ?
C2 C1 C13 N1 151.7(2) . . . . ?
C6 C5 C4 C3 0.5(4) . . . . ?
C2 C3 C4 C5 0.3(4) . . . . ?

data_dc5_2a_m
_database_code_depnum_ccdc_archive 'CCDC 285376'

#===============================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H10 F N O'
_chemical_formula_structural     ?
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_sum            'C13 H10 F N O'
_chemical_formula_weight         215.22
_chemical_compound_source        ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 21/c'

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

_cell_length_a                   8.069(2)
_cell_length_b                   5.3914(14)
_cell_length_c                   23.238(6)
_cell_angle_alpha                90
_cell_angle_beta                 90.169(4)
_cell_angle_gamma                90
_cell_volume                     1011.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    965
_cell_measurement_theta_min      1.4
_cell_measurement_theta_max      25.8
_cell_special_details            
; ?
;

_exptl_crystal_description       blocks
_exptl_crystal_colour            colorless

_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_size_rad          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             448
_exptl_absorpt_coefficient_mu    0.103
_exptl_crystal_density_meas_temp ?

# Permitted for _exptl_absorpt_correction_type :
# analytical 'analytical from crystal shape'
# cylinder 'cylindrical'
# empirical 'empirical from intensities'
# gaussian 'Gaussian from crystal shape'
# integration 'integration from crystal shape'
# multi-scan 'symmetry-related measurements'
# none 'no absorption corr. applied'
# numerical 'numerical from crystal shape'
# psi-scan 'psi-scan corrections'
# refdelf 'refined from delta-F'
# sphere 'spherical'
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min  0.9308
_exptl_absorpt_correction_T_max  0.9798

#===============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
; ?
;
_diffrn_ambient_temperature      290(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 area detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?

_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?

# number of measured reflections (redundant set)
_diffrn_reflns_number            7141
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_sigmaI/netI    0.0226
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.75
_diffrn_reflns_theta_max         27.30
_diffrn_measured_fraction_theta_max 0.922
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_reduction_process 
;
?
;

_reflns_number_total             2045
_reflns_number_gt                1705
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 1998)'
_computing_cell_refinement       SMART
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)'
_computing_publication_material  'PLATON (Spek, 2003)'

#===============================================================================

# 8. REFINEMENT DATA

_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^)+(0.0650P)^2^+0.3336P] 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         2045
_refine_ls_number_parameters     185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0524
_refine_ls_wR_factor_ref         0.1287
_refine_ls_wR_factor_gt          0.1209
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.045

#===============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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 0.28526(16) 0.4502(2) 0.29269(4) 0.0590(4) Uani 1 1 d . . .
N1 N 0.2578(2) 0.7950(3) 0.48257(6) 0.0416(4) Uani 1 1 d . . .
C8 C 0.2711(2) 0.6077(3) 0.38625(7) 0.0393(4) Uani 1 1 d . . .
C6 C 0.0869(2) 0.8562(4) 0.59209(8) 0.0429(4) Uani 1 1 d . . .
C7 C 0.3156(2) 0.7931(3) 0.42507(7) 0.0365(4) Uani 1 1 d . . .
C12 C 0.4139(2) 0.9892(4) 0.40740(8) 0.0435(4) Uani 1 1 d . . .
C9 C 0.3286(2) 0.6295(3) 0.33074(7) 0.0405(4) Uani 1 1 d . . .
C1 C 0.1781(2) 0.6490(3) 0.57654(7) 0.0372(4) Uani 1 1 d . . .
C2 C 0.2233(2) 0.4789(4) 0.61870(8) 0.0425(4) Uani 1 1 d . . .
O1 O 0.24517(19) 0.3798(2) 0.49877(5) 0.0577(4) Uani 1 1 d . . .
C10 C 0.4258(2) 0.8207(4) 0.31196(8) 0.0449(5) Uani 1 1 d . . .
C4 C 0.0894(2) 0.7232(4) 0.69035(8) 0.0476(5) Uani 1 1 d . . .
C13 C 0.2291(2) 0.5932(3) 0.51598(7) 0.0390(4) Uani 1 1 d . . .
C5 C 0.0414(2) 0.8922(4) 0.64880(8) 0.0479(5) Uani 1 1 d . . .
C3 C 0.1799(3) 0.5181(4) 0.67554(8) 0.0470(5) Uani 1 1 d . . .
C11 C 0.4685(2) 1.0012(4) 0.35119(8) 0.0472(5) Uani 1 1 d . . .
H3 H 0.215(2) 0.385(3) 0.7039(7) 0.031(4) Uiso 1 1 d . . .
H11 H 0.534(2) 1.135(4) 0.3384(7) 0.034(4) Uiso 1 1 d . . .
H8 H 0.198(3) 0.478(4) 0.3971(8) 0.048(5) Uiso 1 1 d . . .
H2 H 0.288(2) 0.345(4) 0.6087(8) 0.046(5) Uiso 1 1 d . . .
H6 H 0.056(3) 0.976(4) 0.5640(9) 0.050(5) Uiso 1 1 d . . .
H12 H 0.442(2) 1.114(4) 0.4332(8) 0.047(5) Uiso 1 1 d . . .
H4 H 0.058(3) 0.752(4) 0.7284(10) 0.056(6) Uiso 1 1 d . . .
H10 H 0.465(2) 0.823(4) 0.2735(9) 0.048(5) Uiso 1 1 d . . .
H5 H -0.026(3) 1.033(4) 0.6611(9) 0.060(6) Uiso 1 1 d . . .
H1N H 0.258(2) 0.937(4) 0.4992(8) 0.053(6) Uiso 1 1 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
F1 0.0793(9) 0.0613(8) 0.0363(6) -0.0110(5) 0.0004(5) -0.0031(6)
N1 0.0561(9) 0.0360(8) 0.0328(7) -0.0041(6) 0.0045(6) 0.0003(7)
C8 0.0444(10) 0.0391(9) 0.0343(9) 0.0019(7) 0.0018(7) -0.0016(8)
C6 0.0494(11) 0.0409(10) 0.0385(9) 0.0016(8) 0.0003(7) 0.0015(8)
C7 0.0400(9) 0.0403(9) 0.0293(8) 0.0022(7) 0.0014(6) 0.0067(7)
C12 0.0483(11) 0.0389(10) 0.0434(10) -0.0013(8) -0.0023(8) 0.0007(8)
C9 0.0479(10) 0.0423(10) 0.0314(8) -0.0026(7) -0.0023(7) 0.0090(8)
C1 0.0416(9) 0.0381(9) 0.0318(8) -0.0007(7) 0.0002(6) -0.0047(7)
C2 0.0526(11) 0.0372(9) 0.0377(9) 0.0006(7) 0.0022(7) 0.0024(8)
O1 0.1028(12) 0.0341(7) 0.0362(7) -0.0034(5) 0.0108(7) 0.0058(7)
C10 0.0493(11) 0.0524(11) 0.0331(9) 0.0065(8) 0.0080(7) 0.0080(9)
C4 0.0543(11) 0.0577(12) 0.0309(9) -0.0067(8) 0.0072(8) -0.0093(9)
C13 0.0473(10) 0.0359(9) 0.0338(8) -0.0021(7) -0.0004(7) 0.0010(8)
C5 0.0531(12) 0.0444(11) 0.0463(11) -0.0080(8) 0.0081(8) 0.0027(9)
C3 0.0564(12) 0.0488(11) 0.0356(9) 0.0063(8) -0.0019(8) -0.0051(9)
C11 0.0471(11) 0.0437(10) 0.0510(11) 0.0096(9) 0.0072(8) -0.0009(9)

#===============================================================================

# 10. MOLECULAR GEOMETRY

_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
F1 C9 1.355(2) . ?
N1 C13 1.357(2) . ?
N1 C7 1.416(2) . ?
N1 H1N 0.86(2) . ?
C8 C9 1.377(2) . ?
C8 C7 1.393(2) . ?
C8 H8 0.95(2) . ?
C6 C5 1.383(3) . ?
C6 C1 1.386(3) . ?
C6 H6 0.95(2) . ?
C7 C12 1.385(3) . ?
C12 C11 1.381(3) . ?
C12 H12 0.93(2) . ?
C9 C10 1.368(3) . ?
C1 C2 1.390(2) . ?
C1 C13 1.498(2) . ?
C2 C3 1.384(2) . ?
C2 H2 0.92(2) . ?
O1 C13 1.225(2) . ?
C10 C11 1.376(3) . ?
C10 H10 0.95(2) . ?
C4 C3 1.369(3) . ?
C4 C5 1.382(3) . ?
C4 H4 0.93(2) . ?
C5 H5 0.98(2) . ?
C3 H3 1.013(17) . ?
C11 H11 0.943(19) . ?

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
C13 N1 C7 126.24(15) . . ?
C13 N1 H1N 117.2(13) . . ?
C7 N1 H1N 115.5(13) . . ?
C9 C8 C7 117.29(17) . . ?
C9 C8 H8 121.5(12) . . ?
C7 C8 H8 121.1(12) . . ?
C5 C6 C1 120.27(17) . . ?
C5 C6 H6 119.3(12) . . ?
C1 C6 H6 120.4(12) . . ?
C12 C7 C8 120.18(15) . . ?
C12 C7 N1 117.68(16) . . ?
C8 C7 N1 122.09(16) . . ?
C7 C12 C11 120.04(18) . . ?
C7 C12 H12 120.0(12) . . ?
C11 C12 H12 120.0(12) . . ?
F1 C9 C10 118.47(15) . . ?
F1 C9 C8 117.60(16) . . ?
C10 C9 C8 123.93(17) . . ?
C6 C1 C2 119.10(16) . . ?
C6 C1 C13 123.68(15) . . ?
C2 C1 C13 117.21(16) . . ?
C3 C2 C1 120.34(18) . . ?
C3 C2 H2 120.3(12) . . ?
C1 C2 H2 119.2(12) . . ?
C9 C10 C11 117.66(16) . . ?
C9 C10 H10 120.0(12) . . ?
C11 C10 H10 122.3(12) . . ?
C3 C4 C5 120.33(17) . . ?
C3 C4 H4 121.3(13) . . ?
C5 C4 H4 118.3(13) . . ?
O1 C13 N1 123.22(16) . . ?
O1 C13 C1 121.68(15) . . ?
N1 C13 C1 115.10(15) . . ?
C4 C5 C6 119.93(18) . . ?
C4 C5 H5 117.6(12) . . ?
C6 C5 H5 122.5(12) . . ?
C4 C3 C2 120.02(18) . . ?
C4 C3 H3 123.8(9) . . ?
C2 C3 H3 116.1(9) . . ?
C10 C11 C12 120.90(18) . . ?
C10 C11 H11 118.1(10) . . ?
C12 C11 H11 121.0(10) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 C8 C7 C12 0.0(3) . . . . ?
C9 C8 C7 N1 177.31(15) . . . . ?
C13 N1 C7 C12 -148.05(18) . . . . ?
C13 N1 C7 C8 34.5(3) . . . . ?
C8 C7 C12 C11 -0.2(3) . . . . ?
N1 C7 C12 C11 -177.62(16) . . . . ?
C7 C8 C9 F1 -179.79(15) . . . . ?
C7 C8 C9 C10 0.0(3) . . . . ?
C5 C6 C1 C2 -0.2(3) . . . . ?
C5 C6 C1 C13 178.58(17) . . . . ?
C6 C1 C2 C3 -1.0(3) . . . . ?
C13 C1 C2 C3 -179.79(16) . . . . ?
F1 C9 C10 C11 179.97(16) . . . . ?
C8 C9 C10 C11 0.1(3) . . . . ?
C7 N1 C13 O1 -2.7(3) . . . . ?
C7 N1 C13 C1 176.43(15) . . . . ?
C6 C1 C13 O1 -149.06(19) . . . . ?
C2 C1 C13 O1 29.7(3) . . . . ?
C6 C1 C13 N1 31.8(2) . . . . ?
C2 C1 C13 N1 -149.45(17) . . . . ?
C3 C4 C5 C6 -0.9(3) . . . . ?
C1 C6 C5 C4 1.1(3) . . . . ?
C5 C4 C3 C2 -0.2(3) . . . . ?
C1 C2 C3 C4 1.2(3) . . . . ?
C9 C10 C11 C12 -0.3(3) . . . . ?
C7 C12 C11 C10 0.3(3) . . . . ?

data_dc4_3_m
_database_code_depnum_ccdc_archive 'CCDC 285377'

#===============================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
;
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H10 F N O'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural     ?
_chemical_formula_sum            'C13 H10 F N O'
_chemical_formula_iupac          ?
_chemical_formula_weight         215.22
_chemical_compound_source        ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_symmetry_Int_Tables_number      2

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,-z

_cell_length_a                   5.349(3)
_cell_length_b                   7.599(4)
_cell_length_c                   12.945(6)
_cell_angle_alpha                92.124(8)
_cell_angle_beta                 101.179(7)
_cell_angle_gamma                90.162(8)
_cell_volume                     515.8(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    775
_cell_measurement_theta_min      1.3
_cell_measurement_theta_max      25.4
_cell_special_details            
;
;

_exptl_crystal_description       ' needle'
_exptl_crystal_colour            ' colorless'

_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.05
_exptl_crystal_size_rad          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             224
_exptl_absorpt_coefficient_mu    0.101
_exptl_crystal_density_meas_temp ?

# Permitted for _exptl_absorpt_correction_type :
# analytical 'analytical from crystal shape'
# Example: de Meulenaer&Tompa: ABST
# cylinder 'cylindrical'
# gaussian 'Gaussian from crystal shape'
# Example: PLATON/ABSG
# integration 'integration from crystal shape'
# multi-scan 'symmetry-related measurements'
# Example: SADABS, MULABS
# none 'no absorption corr. applied'
# numerical 'numerical from crystal shape'
# psi-scan 'psi-scan corrections'
# Example: PLATON/ABSP
# refdelf 'refined from delta-F'
# Example: SHELXA, DIFABS, DELABS
# sphere 'spherical'
# Example: PLATON/ABSS
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min  0.9453
_exptl_absorpt_correction_T_max  0.9950

#===============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
;
;
_diffrn_ambient_temperature      290(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 area detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?

# number of measured reflections (redundant set)
_diffrn_reflns_number            3381
_diffrn_reflns_av_R_equivalents  0.0202
_diffrn_reflns_av_sigmaI/netI    0.0216
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.60
_diffrn_reflns_theta_max         20.81
_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        20.81
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_reduction_process 
;
;

_reflns_number_total             1082
_reflns_number_gt                880
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 1998)'
_computing_cell_refinement       SMART
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)'
_computing_publication_material  'PLATON (Spek, 2003)'
#===============================================================================

# 8. REFINEMENT DATA

_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^)+(0.0677P)^2^+0.0000P] 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    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1082
_refine_ls_number_parameters     185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0323
_refine_ls_wR_factor_ref         0.1121
_refine_ls_wR_factor_gt          0.0821
_refine_ls_goodness_of_fit_ref   1.222
_refine_ls_restrained_S_all      1.222
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.060

#===============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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 0.4206(3) 0.7737(3) 1.42280(13) 0.0679(7) Uani 1 1 d . . .
N1 N 0.1687(5) 0.7429(3) 0.92229(18) 0.0374(7) Uani 1 1 d . . .
O1 O 0.6007(3) 0.7564(3) 0.95873(13) 0.0539(7) Uani 1 1 d . . .
C1 C 0.3904(5) 0.7591(3) 1.1039(2) 0.0321(7) Uani 1 1 d . . .
C3 C 0.6005(6) 0.8522(4) 1.2796(2) 0.0428(8) Uani 1 1 d . . .
C13 C 0.3970(5) 0.7525(3) 0.9896(2) 0.0362(7) Uani 1 1 d . . .
C4 C 0.4104(6) 0.7694(4) 1.3169(2) 0.0411(8) Uani 1 1 d . . .
C12 C -0.0940(5) 0.8108(4) 0.7554(2) 0.0389(8) Uani 1 1 d . . .
C2 C 0.5895(5) 0.8435(4) 1.1727(2) 0.0382(8) Uani 1 1 d . . .
C5 C 0.2109(6) 0.6827(4) 1.2535(2) 0.0416(8) Uani 1 1 d . . .
C8 C 0.2878(5) 0.6499(4) 0.7546(2) 0.0401(8) Uani 1 1 d . . .
C7 C 0.1242(5) 0.7346(3) 0.8103(2) 0.0332(7) Uani 1 1 d . . .
C6 C 0.2013(5) 0.6789(4) 1.1464(2) 0.0380(8) Uani 1 1 d . . .
C9 C 0.2331(6) 0.6436(4) 0.6462(2) 0.0447(8) Uani 1 1 d . . .
C11 C -0.1479(6) 0.8029(4) 0.6475(2) 0.0447(8) Uani 1 1 d . . .
C10 C 0.0151(6) 0.7188(4) 0.5919(2) 0.0466(8) Uani 1 1 d . . .
H10 H -0.026(5) 0.716(3) 0.515(2) 0.044(8) Uiso 1 1 d . . .
H9 H 0.345(5) 0.587(3) 0.606(2) 0.046(8) Uiso 1 1 d . . .
H3 H 0.736(6) 0.917(4) 1.327(2) 0.062(9) Uiso 1 1 d . . .
H12 H -0.206(5) 0.866(3) 0.7933(19) 0.044(8) Uiso 1 1 d . . .
H5 H 0.090(5) 0.622(3) 1.285(2) 0.051(8) Uiso 1 1 d . . .
H8 H 0.434(5) 0.596(3) 0.7910(19) 0.040(7) Uiso 1 1 d . . .
H11 H -0.300(6) 0.857(4) 0.608(2) 0.058(9) Uiso 1 1 d . . .
H2 H 0.708(5) 0.897(3) 1.1445(19) 0.038(8) Uiso 1 1 d . . .
H6 H 0.072(5) 0.622(3) 1.1021(18) 0.029(7) Uiso 1 1 d . . .
H1N H 0.044(6) 0.761(4) 0.950(2) 0.051(10) Uiso 1 1 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
F1 0.0705(13) 0.0952(15) 0.0380(12) 0.0033(9) 0.0108(9) -0.0019(10)
N1 0.0284(14) 0.0502(16) 0.0341(16) 0.0009(11) 0.0073(13) 0.0024(11)
O1 0.0319(12) 0.0875(17) 0.0430(13) 0.0017(11) 0.0093(10) -0.0048(10)
C1 0.0296(16) 0.0311(16) 0.0361(18) 0.0030(13) 0.0072(14) 0.0019(13)
C3 0.0395(18) 0.048(2) 0.038(2) -0.0033(15) 0.0010(15) 0.0016(15)
C13 0.0297(17) 0.0371(18) 0.0417(19) 0.0033(13) 0.0061(16) 0.0003(12)
C4 0.0476(19) 0.0490(19) 0.0273(19) 0.0052(14) 0.0083(16) 0.0091(16)
C12 0.0306(17) 0.0456(19) 0.041(2) -0.0019(15) 0.0084(16) 0.0024(14)
C2 0.0300(17) 0.0388(18) 0.046(2) 0.0048(15) 0.0081(16) -0.0018(14)
C5 0.0382(18) 0.0478(19) 0.040(2) 0.0066(15) 0.0094(16) -0.0005(15)
C8 0.0325(17) 0.0432(19) 0.044(2) 0.0014(15) 0.0059(15) 0.0026(14)
C7 0.0303(16) 0.0358(16) 0.0328(19) 0.0005(13) 0.0048(13) -0.0036(13)
C6 0.0315(17) 0.0395(18) 0.041(2) 0.0003(15) 0.0008(16) -0.0033(14)
C9 0.046(2) 0.050(2) 0.041(2) -0.0069(15) 0.0162(17) -0.0020(16)
C11 0.0371(18) 0.056(2) 0.039(2) 0.0033(15) 0.0021(16) 0.0035(15)
C10 0.0474(19) 0.059(2) 0.032(2) 0.0011(15) 0.0041(17) -0.0047(16)

#===============================================================================

# 10. MOLECULAR GEOMETRY

_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
F1 C4 1.360(3) . ?
N1 C13 1.356(3) . ?
N1 C7 1.422(3) . ?
N1 H1N 0.83(3) . ?
O1 C13 1.231(3) . ?
C1 C2 1.387(4) . ?
C1 C6 1.390(4) . ?
C1 C13 1.486(4) . ?
C3 C4 1.368(4) . ?
C3 C2 1.373(4) . ?
C3 H3 0.98(3) . ?
C4 C5 1.365(4) . ?
C12 C11 1.369(4) . ?
C12 C7 1.384(4) . ?
C12 H12 0.93(3) . ?
C2 H2 0.89(3) . ?
C5 C6 1.377(4) . ?
C5 H5 0.96(3) . ?
C8 C9 1.376(4) . ?
C8 C7 1.383(4) . ?
C8 H8 0.93(3) . ?
C6 H6 0.90(2) . ?
C9 C10 1.377(4) . ?
C9 H9 0.96(3) . ?
C11 C10 1.378(4) . ?
C11 H11 0.97(3) . ?
C10 H10 0.98(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
C13 N1 C7 127.3(3) . . ?
C13 N1 H1N 114.7(19) . . ?
C7 N1 H1N 117.2(19) . . ?
C2 C1 C6 118.0(3) . . ?
C2 C1 C13 118.2(2) . . ?
C6 C1 C13 123.7(2) . . ?
C4 C3 C2 117.4(3) . . ?
C4 C3 H3 120.9(16) . . ?
C2 C3 H3 121.7(17) . . ?
O1 C13 N1 122.4(3) . . ?
O1 C13 C1 121.1(2) . . ?
N1 C13 C1 116.5(2) . . ?
F1 C4 C5 118.2(3) . . ?
F1 C4 C3 118.3(3) . . ?
C5 C4 C3 123.4(3) . . ?
C11 C12 C7 120.7(3) . . ?
C11 C12 H12 120.5(15) . . ?
C7 C12 H12 118.8(15) . . ?
C3 C2 C1 121.9(3) . . ?
C3 C2 H2 120.8(16) . . ?
C1 C2 H2 117.3(16) . . ?
C4 C5 C6 118.0(3) . . ?
C4 C5 H5 118.8(15) . . ?
C6 C5 H5 123.1(16) . . ?
C9 C8 C7 119.9(3) . . ?
C9 C8 H8 120.5(15) . . ?
C7 C8 H8 119.7(15) . . ?
C8 C7 C12 119.1(3) . . ?
C8 C7 N1 122.4(2) . . ?
C12 C7 N1 118.5(3) . . ?
C5 C6 C1 121.1(3) . . ?
C5 C6 H6 120.3(15) . . ?
C1 C6 H6 118.5(15) . . ?
C8 C9 C10 120.9(3) . . ?
C8 C9 H9 121.3(16) . . ?
C10 C9 H9 117.8(16) . . ?
C12 C11 C10 120.3(3) . . ?
C12 C11 H11 121.4(16) . . ?
C10 C11 H11 118.2(16) . . ?
C9 C10 C11 119.2(3) . . ?
C9 C10 H10 121.9(14) . . ?
C11 C10 H10 118.9(14) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N1 C13 O1 0.5(4) . . . . ?
C7 N1 C13 C1 -179.7(2) . . . . ?
C2 C1 C13 O1 27.7(4) . . . . ?
C6 C1 C13 O1 -149.5(3) . . . . ?
C2 C1 C13 N1 -152.0(2) . . . . ?
C6 C1 C13 N1 30.8(4) . . . . ?
C2 C3 C4 F1 178.8(2) . . . . ?
C2 C3 C4 C5 -1.2(4) . . . . ?
C4 C3 C2 C1 1.9(4) . . . . ?
C6 C1 C2 C3 -1.3(4) . . . . ?
C13 C1 C2 C3 -178.6(2) . . . . ?
F1 C4 C5 C6 179.9(2) . . . . ?
C3 C4 C5 C6 0.0(4) . . . . ?
C9 C8 C7 C12 0.5(4) . . . . ?
C9 C8 C7 N1 179.0(2) . . . . ?
C11 C12 C7 C8 0.0(4) . . . . ?
C11 C12 C7 N1 -178.6(2) . . . . ?
C13 N1 C7 C8 33.5(4) . . . . ?
C13 N1 C7 C12 -148.0(3) . . . . ?
C4 C5 C6 C1 0.7(4) . . . . ?
C2 C1 C6 C5 -0.1(4) . . . . ?
C13 C1 C6 C5 177.1(2) . . . . ?
C7 C8 C9 C10 -0.9(4) . . . . ?
C7 C12 C11 C10 -0.1(4) . . . . ?
C8 C9 C10 C11 0.8(4) . . . . ?
C12 C11 C10 C9 -0.3(4) . . . . ?

#===============================================================================

data_dc4_1_m
_database_code_depnum_ccdc_archive 'CCDC 285378'

#===============================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H10 F N O'
_chemical_formula_structural     ?
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_sum            'C13 H10 F N O'
_chemical_formula_weight         215.22
_chemical_compound_source        ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 21'

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

_cell_length_a                   5.4206(15)
_cell_length_b                   6.2580(17)
_cell_length_c                   15.534(4)
_cell_angle_alpha                90
_cell_angle_beta                 97.454(5)
_cell_angle_gamma                90
_cell_volume                     522.5(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    556
_cell_measurement_theta_min      1.6
_cell_measurement_theta_max      25.4
_cell_special_details            
; ?
;

_exptl_crystal_description       plates
_exptl_crystal_colour            colorless

_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_exptl_crystal_size_rad          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             224
_exptl_absorpt_coefficient_mu    0.099
_exptl_crystal_density_meas_temp ?

# Permitted for _exptl_absorpt_correction_type :
# analytical 'analytical from crystal shape'
# cylinder 'cylindrical'
# empirical 'empirical from intensities'
# gaussian 'Gaussian from crystal shape'
# integration 'integration from crystal shape'
# multi-scan 'symmetry-related measurements'
# none 'no absorption corr. applied'
# numerical 'numerical from crystal shape'
# psi-scan 'psi-scan corrections'
# refdelf 'refined from delta-F'
# sphere 'spherical'
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min  0.9434
_exptl_absorpt_correction_T_max  0.9931

#===============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
; ?
;
_diffrn_ambient_temperature      290(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 area detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?

_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?

# number of measured reflections (redundant set)
_diffrn_reflns_number            3606
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_sigmaI/netI    0.0736
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.64
_diffrn_reflns_theta_max         24.99
_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_reduction_process 
;
?
;

_reflns_number_total             1783
_reflns_number_gt                1070
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 1998)'
_computing_cell_refinement       SMART
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)'
_computing_publication_material  'PLATON (Spek, 2003)'

#===============================================================================

# 8. REFINEMENT DATA

_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^)+(0.0857P)^2^+0.0000P] 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         1783
_refine_ls_number_parameters     149
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1272
_refine_ls_R_factor_gt           0.0635
_refine_ls_wR_factor_ref         0.1116
_refine_ls_wR_factor_gt          0.0931
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.118
_refine_diff_density_min         -0.108
_refine_diff_density_rms         0.031

#===============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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 0.0478(4) 0.2195(5) 0.38346(14) 0.0848(8) Uani 1 1 d . . .
O1 O 0.6152(5) 0.2647(5) 0.23456(17) 0.0758(9) Uani 1 1 d . . .
N1 N 0.2056(7) 0.3462(5) 0.2286(2) 0.0566(10) Uani 1 1 d . . .
C6 C 0.2025(7) 0.0511(8) 0.3787(3) 0.0573(11) Uani 1 1 d . . .
C12 C 0.0081(8) 0.6680(7) 0.1759(3) 0.0627(12) Uani 1 1 d . . .
H12 H -0.1065 0.6434 0.2144 0.075 Uiso 1 1 calc R . .
C1 C 0.3720(7) 0.0564(6) 0.3208(2) 0.0498(10) Uani 1 1 d . . .
C7 C 0.1965(7) 0.5270(7) 0.1713(2) 0.0504(10) Uani 1 1 d . . .
C5 C 0.1835(8) -0.1153(8) 0.4360(3) 0.0739(14) Uani 1 1 d . . .
H5 H 0.0636 -0.1139 0.4737 0.089 Uiso 1 1 calc R . .
C10 C 0.1541(8) 0.8842(8) 0.0662(3) 0.0719(14) Uani 1 1 d . . .
H10 H 0.1408 1.0048 0.0310 0.086 Uiso 1 1 calc R . .
C3 C 0.5195(8) -0.2841(8) 0.3797(3) 0.0718(12) Uani 1 1 d . . .
H3 H 0.6277 -0.3995 0.3796 0.086 Uiso 1 1 calc R . .
C13 C 0.4090(8) 0.2322(7) 0.2576(2) 0.0584(11) Uani 1 1 d . . .
C11 C -0.0147(7) 0.8471(7) 0.1239(3) 0.0721(14) Uani 1 1 d . . .
H11 H -0.1439 0.9431 0.1277 0.087 Uiso 1 1 calc R . .
C4 C 0.3445(8) -0.2803(9) 0.4355(3) 0.0737(13) Uani 1 1 d . . .
H4 H 0.3359 -0.3932 0.4739 0.088 Uiso 1 1 calc R . .
C8 C 0.3625(7) 0.5622(8) 0.1134(3) 0.0667(12) Uani 1 1 d . . .
H8 H 0.4900 0.4650 0.1090 0.080 Uiso 1 1 calc R . .
C9 C 0.3405(8) 0.7398(9) 0.0621(3) 0.0789(13) Uani 1 1 d . . .
H9 H 0.4552 0.7630 0.0234 0.095 Uiso 1 1 calc R . .
C2 C 0.5345(8) -0.1152(7) 0.3233(3) 0.0656(12) Uani 1 1 d . . .
H2 H 0.6562 -0.1166 0.2862 0.079 Uiso 1 1 calc R . .
H1N H 0.060(8) 0.313(7) 0.250(3) 0.100(18) Uiso 1 1 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
F1 0.0825(16) 0.1021(19) 0.0759(15) 0.0070(16) 0.0335(13) 0.0184(19)
O1 0.0501(16) 0.088(2) 0.094(2) 0.0186(19) 0.0252(15) 0.0039(19)
N1 0.044(2) 0.063(3) 0.064(2) -0.003(2) 0.0127(19) -0.004(2)
C6 0.055(3) 0.065(3) 0.051(3) -0.002(3) 0.005(2) 0.012(3)
C12 0.060(3) 0.061(3) 0.070(3) 0.004(3) 0.017(2) 0.001(2)
C1 0.060(3) 0.047(3) 0.044(2) -0.007(2) 0.013(2) -0.015(3)
C7 0.053(3) 0.059(3) 0.041(2) 0.000(3) 0.012(2) -0.004(2)
C5 0.067(3) 0.095(4) 0.059(3) 0.018(3) 0.003(2) -0.009(3)
C10 0.069(3) 0.065(3) 0.081(4) 0.021(3) 0.006(3) -0.016(3)
C3 0.078(3) 0.053(3) 0.084(3) 0.003(3) 0.007(3) -0.001(3)
C13 0.047(2) 0.066(3) 0.062(3) -0.016(3) 0.006(2) 0.004(3)
C11 0.053(3) 0.070(4) 0.092(3) -0.003(3) 0.003(3) 0.007(3)
C4 0.066(3) 0.073(4) 0.078(3) 0.020(3) -0.007(3) -0.016(3)
C8 0.067(3) 0.071(3) 0.063(3) 0.004(3) 0.013(2) 0.013(3)
C9 0.062(3) 0.103(4) 0.075(3) 0.027(3) 0.019(2) -0.001(4)
C2 0.067(3) 0.057(3) 0.075(3) -0.005(3) 0.020(2) 0.006(3)

#===============================================================================

# 10. MOLECULAR GEOMETRY

_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
F1 C6 1.355(5) . ?
O1 C13 1.234(4) . ?
N1 C13 1.341(5) . ?
N1 C7 1.436(5) . ?
N1 H1N 0.91(4) . ?
C6 C1 1.367(5) . ?
C6 C5 1.382(6) . ?
C12 C7 1.358(5) . ?
C12 C11 1.377(6) . ?
C12 H12 0.9300 . ?
C1 C2 1.386(5) . ?
C1 C13 1.505(5) . ?
C7 C8 1.371(5) . ?
C5 C4 1.353(6) . ?
C5 H5 0.9300 . ?
C10 C9 1.363(6) . ?
C10 C11 1.381(6) . ?
C10 H10 0.9300 . ?
C3 C4 1.366(5) . ?
C3 C2 1.382(6) . ?
C3 H3 0.9300 . ?
C11 H11 0.9300 . ?
C4 H4 0.9300 . ?
C8 C9 1.364(6) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C2 H2 0.9300 . ?

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
C13 N1 C7 126.0(4) . . ?
C13 N1 H1N 118(3) . . ?
C7 N1 H1N 116(3) . . ?
F1 C6 C1 119.4(4) . . ?
F1 C6 C5 116.9(4) . . ?
C1 C6 C5 123.7(4) . . ?
C7 C12 C11 120.6(4) . . ?
C7 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C6 C1 C2 116.2(4) . . ?
C6 C1 C13 127.2(4) . . ?
C2 C1 C13 116.5(4) . . ?
C12 C7 C8 119.4(4) . . ?
C12 C7 N1 116.5(4) . . ?
C8 C7 N1 124.1(4) . . ?
C4 C5 C6 118.0(4) . . ?
C4 C5 H5 121.0 . . ?
C6 C5 H5 121.0 . . ?
C9 C10 C11 118.5(5) . . ?
C9 C10 H10 120.8 . . ?
C11 C10 H10 120.8 . . ?
C4 C3 C2 119.4(5) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
O1 C13 N1 123.4(4) . . ?
O1 C13 C1 120.8(4) . . ?
N1 C13 C1 115.8(4) . . ?
C12 C11 C10 120.0(4) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C5 C4 C3 121.3(5) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C9 C8 C7 120.0(4) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C10 C9 C8 121.4(4) . . ?
C10 C9 H9 119.3 . . ?
C8 C9 H9 119.3 . . ?
C3 C2 C1 121.4(4) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C6 C1 C2 176.1(3) . . . . ?
C5 C6 C1 C2 -1.7(6) . . . . ?
F1 C6 C1 C13 -0.9(6) . . . . ?
C5 C6 C1 C13 -178.7(4) . . . . ?
C11 C12 C7 C8 -1.1(6) . . . . ?
C11 C12 C7 N1 179.5(3) . . . . ?
C13 N1 C7 C12 -155.1(4) . . . . ?
C13 N1 C7 C8 25.6(5) . . . . ?
F1 C6 C5 C4 -176.7(3) . . . . ?
C1 C6 C5 C4 1.1(6) . . . . ?
C7 N1 C13 O1 -3.6(6) . . . . ?
C7 N1 C13 C1 177.0(3) . . . . ?
C6 C1 C13 O1 150.7(4) . . . . ?
C2 C1 C13 O1 -26.3(5) . . . . ?
C6 C1 C13 N1 -29.9(5) . . . . ?
C2 C1 C13 N1 153.2(3) . . . . ?
C7 C12 C11 C10 0.3(6) . . . . ?
C9 C10 C11 C12 0.3(6) . . . . ?
C6 C5 C4 C3 -0.6(7) . . . . ?
C2 C3 C4 C5 0.8(7) . . . . ?
C12 C7 C8 C9 1.3(6) . . . . ?
N1 C7 C8 C9 -179.4(4) . . . . ?
C11 C10 C9 C8 -0.1(7) . . . . ?
C7 C8 C9 C10 -0.7(7) . . . . ?
C4 C3 C2 C1 -1.4(6) . . . . ?
C6 C1 C2 C3 1.8(5) . . . . ?
C13 C1 C2 C3 179.1(4) . . . . ?

data_dc2_3
_database_code_depnum_ccdc_archive 'CCDC 285379'

#===============================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H9 F2 N O'
_chemical_formula_structural     ?
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_sum            'C13 H9 F2 N O'
_chemical_formula_weight         233.21
_chemical_compound_source        ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 21/c'

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

_cell_length_a                   12.2353(16)
_cell_length_b                   10.8787(14)
_cell_length_c                   7.8648(10)
_cell_angle_alpha                90
_cell_angle_beta                 90.232(2)
_cell_angle_gamma                90
_cell_volume                     1046.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    555
_cell_measurement_theta_min      1.2
_cell_measurement_theta_max      25.4
_cell_special_details            
; ?
;

_exptl_crystal_description       ' plates '
_exptl_crystal_colour            colorless

_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.05
_exptl_crystal_size_rad          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             480
_exptl_absorpt_coefficient_mu    0.119
_exptl_crystal_density_meas_temp ?

# Permitted for _exptl_absorpt_correction_type :
# analytical 'analytical from crystal shape'
# cylinder 'cylindrical'
# empirical 'empirical from intensities'
# gaussian 'Gaussian from crystal shape'
# integration 'integration from crystal shape'
# multi-scan 'symmetry-related measurements'
# none 'no absorption corr. applied'
# numerical 'numerical from crystal shape'
# psi-scan 'psi-scan corrections'
# refdelf 'refined from delta-F'
# sphere 'spherical'
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min  0.9381
_exptl_absorpt_correction_T_max  0.9941

#===============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
; ?
;
_diffrn_ambient_temperature      290(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 area detector'
_diffrn_measurement_method       '\f and \w scans'

# number of measured reflections (redundant set)
_diffrn_reflns_number            7786
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_sigmaI/netI    0.0253
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.66
_diffrn_reflns_theta_max         26.36
_diffrn_measured_fraction_theta_max 0.960
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.977
_diffrn_reflns_reduction_process 
;
?
;

_reflns_number_total             2051
_reflns_number_gt                1670
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 1998)'
_computing_cell_refinement       SMART
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)'
_computing_publication_material  'PLATON (Spek, 2003)'

#===============================================================================

# 8. REFINEMENT DATA

_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^)+(0.0369P)^2^+0.2256P] 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         2051
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0499
_refine_ls_wR_factor_ref         0.1002
_refine_ls_wR_factor_gt          0.0933
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_restrained_S_all      1.149
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.034

#===============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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
F2 F 0.89773(8) 1.06031(11) 0.22360(17) 0.0623(4) Uani 1 1 d . . .
N1 N 0.54829(12) 0.86011(16) 0.2261(2) 0.0375(4) Uani 1 1 d . . .
F1 F 0.05271(9) 0.82266(13) 0.44500(18) 0.0686(4) Uani 1 1 d . . .
O1 O 0.50136(10) 1.06169(12) 0.24338(19) 0.0531(4) Uani 1 1 d . . .
C12 C 0.70257(15) 0.77422(18) 0.0820(2) 0.0387(4) Uani 1 1 d . . .
C7 C 0.65912(13) 0.86951(16) 0.1757(2) 0.0332(4) Uani 1 1 d . . .
C13 C 0.47692(13) 0.95327(17) 0.2567(2) 0.0351(4) Uani 1 1 d . . .
C4 C 0.15578(15) 0.85305(18) 0.4000(3) 0.0437(5) Uani 1 1 d . . .
C2 C 0.27763(14) 0.98829(17) 0.2634(3) 0.0374(4) Uani 1 1 d . . .
C8 C 0.72471(15) 0.96796(18) 0.2242(3) 0.0388(5) Uani 1 1 d . . .
C5 C 0.23969(16) 0.77595(19) 0.4473(3) 0.0447(5) Uani 1 1 d . . .
C1 C 0.36478(13) 0.91309(16) 0.3077(2) 0.0324(4) Uani 1 1 d . . .
C6 C 0.34471(15) 0.80633(17) 0.3990(2) 0.0390(5) Uani 1 1 d . . .
C3 C 0.17192(15) 0.95854(19) 0.3094(3) 0.0435(5) Uani 1 1 d . . .
C10 C 0.87837(15) 0.87149(18) 0.0845(3) 0.0426(5) Uani 1 1 d . . .
C11 C 0.81142(16) 0.77512(19) 0.0373(3) 0.0440(5) Uani 1 1 d . . .
C9 C 0.83282(14) 0.96506(17) 0.1761(3) 0.0400(5) Uani 1 1 d . . .
H2 H 0.2894(13) 1.0611(17) 0.205(2) 0.031(5) Uiso 1 1 d . . .
H8 H 0.6999(14) 1.0303(17) 0.286(2) 0.036(5) Uiso 1 1 d . . .
H10 H 0.9521(16) 0.8751(17) 0.059(2) 0.042(5) Uiso 1 1 d . . .
H6 H 0.4050(14) 0.7538(17) 0.432(2) 0.036(5) Uiso 1 1 d . . .
H11 H 0.8410(16) 0.7112(18) -0.028(2) 0.046(5) Uiso 1 1 d . . .
H12 H 0.6547(15) 0.7060(18) 0.049(2) 0.043(5) Uiso 1 1 d . . .
H3 H 0.1115(16) 1.0102(18) 0.280(2) 0.045(5) Uiso 1 1 d . . .
H5 H 0.2276(16) 0.704(2) 0.513(3) 0.053(6) Uiso 1 1 d . . .
H1N H 0.5256(16) 0.789(2) 0.229(2) 0.043(6) Uiso 1 1 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
F2 0.0341(6) 0.0541(8) 0.0987(11) -0.0133(7) 0.0036(6) -0.0103(5)
N1 0.0288(8) 0.0325(9) 0.0512(10) -0.0004(7) 0.0055(7) -0.0025(7)
F1 0.0352(7) 0.0776(9) 0.0931(10) 0.0033(8) 0.0168(6) -0.0159(6)
O1 0.0323(7) 0.0319(7) 0.0950(12) 0.0064(7) 0.0096(7) -0.0027(6)
C12 0.0379(10) 0.0349(10) 0.0434(11) -0.0009(8) 0.0014(8) 0.0013(8)
C7 0.0280(9) 0.0346(9) 0.0370(10) 0.0058(8) 0.0028(7) 0.0011(7)
C13 0.0284(9) 0.0363(10) 0.0406(11) 0.0014(8) -0.0008(7) -0.0011(7)
C4 0.0302(10) 0.0505(12) 0.0504(12) -0.0082(10) 0.0089(8) -0.0112(9)
C2 0.0330(10) 0.0322(10) 0.0471(12) 0.0020(9) 0.0017(8) -0.0014(8)
C8 0.0336(10) 0.0357(10) 0.0473(12) -0.0054(9) 0.0049(8) 0.0035(8)
C5 0.0440(11) 0.0399(11) 0.0502(13) 0.0056(10) 0.0074(9) -0.0082(9)
C1 0.0290(9) 0.0328(9) 0.0355(10) -0.0040(8) 0.0015(7) -0.0011(7)
C6 0.0351(10) 0.0356(10) 0.0464(12) 0.0010(9) 0.0014(8) 0.0023(8)
C3 0.0291(10) 0.0464(12) 0.0549(13) -0.0025(10) -0.0002(8) 0.0036(9)
C10 0.0272(9) 0.0480(12) 0.0525(12) 0.0059(10) 0.0081(8) 0.0038(8)
C11 0.0406(11) 0.0442(11) 0.0473(12) -0.0034(10) 0.0091(9) 0.0093(9)
C9 0.0275(9) 0.0392(11) 0.0532(12) 0.0026(9) 0.0002(8) -0.0045(8)

#===============================================================================

# 10. MOLECULAR GEOMETRY

_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
F2 C9 1.357(2) . ?
N1 C13 1.360(2) . ?
N1 C7 1.418(2) . ?
N1 H1N 0.83(2) . ?
F1 C4 1.352(2) . ?
O1 C13 1.221(2) . ?
C12 C11 1.379(3) . ?
C12 C7 1.380(2) . ?
C12 H12 0.98(2) . ?
C7 C8 1.391(2) . ?
C13 C1 1.496(2) . ?
C4 C3 1.365(3) . ?
C4 C5 1.376(3) . ?
C2 C3 1.383(3) . ?
C2 C1 1.387(2) . ?
C2 H2 0.926(18) . ?
C8 C9 1.378(2) . ?
C8 H8 0.891(19) . ?
C5 C6 1.381(3) . ?
C5 H5 0.95(2) . ?
C1 C6 1.388(2) . ?
C6 H6 0.968(18) . ?
C3 H3 0.96(2) . ?
C10 C9 1.367(3) . ?
C10 C11 1.380(3) . ?
C10 H10 0.926(19) . ?
C11 H11 0.94(2) . ?

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
C13 N1 C7 127.68(17) . . ?
C13 N1 H1N 118.8(14) . . ?
C7 N1 H1N 113.4(14) . . ?
C11 C12 C7 120.36(18) . . ?
C11 C12 H12 121.0(11) . . ?
C7 C12 H12 118.6(11) . . ?
C12 C7 C8 120.13(16) . . ?
C12 C7 N1 117.78(16) . . ?
C8 C7 N1 122.02(16) . . ?
O1 C13 N1 123.15(16) . . ?
O1 C13 C1 122.02(16) . . ?
N1 C13 C1 114.83(16) . . ?
F1 C4 C3 118.62(18) . . ?
F1 C4 C5 118.41(18) . . ?
C3 C4 C5 122.97(17) . . ?
C3 C2 C1 121.01(18) . . ?
C3 C2 H2 118.5(10) . . ?
C1 C2 H2 120.5(10) . . ?
C9 C8 C7 117.43(17) . . ?
C9 C8 H8 119.9(11) . . ?
C7 C8 H8 122.7(11) . . ?
C4 C5 C6 118.27(19) . . ?
C4 C5 H5 122.1(13) . . ?
C6 C5 H5 119.6(13) . . ?
C2 C1 C6 119.07(16) . . ?
C2 C1 C13 117.73(16) . . ?
C6 C1 C13 123.19(16) . . ?
C5 C6 C1 120.61(18) . . ?
C5 C6 H6 119.6(11) . . ?
C1 C6 H6 119.7(11) . . ?
C4 C3 C2 118.07(18) . . ?
C4 C3 H3 120.5(11) . . ?
C2 C3 H3 121.4(11) . . ?
C9 C10 C11 117.67(17) . . ?
C9 C10 H10 118.9(12) . . ?
C11 C10 H10 123.5(12) . . ?
C12 C11 C10 120.65(18) . . ?
C12 C11 H11 120.6(12) . . ?
C10 C11 H11 118.7(12) . . ?
F2 C9 C10 118.32(15) . . ?
F2 C9 C8 117.92(17) . . ?
C10 C9 C8 123.76(18) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 C12 C7 C8 0.7(3) . . . . ?
C11 C12 C7 N1 -176.46(18) . . . . ?
C13 N1 C7 C12 -152.11(18) . . . . ?
C13 N1 C7 C8 30.8(3) . . . . ?
C7 N1 C13 O1 0.1(3) . . . . ?
C7 N1 C13 C1 179.80(17) . . . . ?
C12 C7 C8 C9 -0.4(3) . . . . ?
N1 C7 C8 C9 176.61(17) . . . . ?
F1 C4 C5 C6 179.07(17) . . . . ?
C3 C4 C5 C6 -0.8(3) . . . . ?
C3 C2 C1 C6 0.2(3) . . . . ?
C3 C2 C1 C13 -178.56(17) . . . . ?
O1 C13 C1 C2 30.0(3) . . . . ?
N1 C13 C1 C2 -149.63(17) . . . . ?
O1 C13 C1 C6 -148.67(19) . . . . ?
N1 C13 C1 C6 31.7(3) . . . . ?
C4 C5 C6 C1 1.1(3) . . . . ?
C2 C1 C6 C5 -0.8(3) . . . . ?
C13 C1 C6 C5 177.86(18) . . . . ?
F1 C4 C3 C2 -179.68(18) . . . . ?
C5 C4 C3 C2 0.2(3) . . . . ?
C1 C2 C3 C4 0.1(3) . . . . ?
C7 C12 C11 C10 -0.4(3) . . . . ?
C9 C10 C11 C12 -0.1(3) . . . . ?
C11 C10 C9 F2 179.87(18) . . . . ?
C11 C10 C9 C8 0.4(3) . . . . ?
C7 C8 C9 F2 -179.61(17) . . . . ?
C7 C8 C9 C10 -0.1(3) . . . . ?

data_dc2_1am
_database_code_depnum_ccdc_archive 'CCDC 285380'

#===============================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
;
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H9 F2 N O'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural     ?
_chemical_formula_sum            'C13 H9 F2 N O'
_chemical_formula_iupac          ?
_chemical_formula_weight         233.21
_chemical_compound_source        'see text'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_symmetry_Int_Tables_number      29

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,1/2+z
3 1/2-x,y,1/2+z
4 1/2+x,-y,z

_cell_length_a                   24.660(5)
_cell_length_b                   5.2031(12)
_cell_length_c                   8.2440(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1057.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    685
_cell_measurement_theta_min      1.4
_cell_measurement_theta_max      25.4
_cell_special_details            
;
;

_exptl_crystal_description       plates
_exptl_crystal_colour            colorless

_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.08
_exptl_crystal_size_rad          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             480
_exptl_absorpt_coefficient_mu    0.117
_exptl_crystal_density_meas_temp ?

# Permitted for _exptl_absorpt_correction_type :
# analytical 'analytical from crystal shape'
# Example: de Meulenaer&Tompa: ABST
# cylinder 'cylindrical'
# gaussian 'Gaussian from crystal shape'
# Example: PLATON/ABSG
# integration 'integration from crystal shape'
# multi-scan 'symmetry-related measurements'
# Example: SADABS, MULABS
# none 'no absorption corr. applied'
# numerical 'numerical from crystal shape'
# psi-scan 'psi-scan corrections'
# Example: PLATON/ABSP
# refdelf 'refined from delta-F'
# Example: SHELXA, DIFABS, DELABS
# sphere 'spherical'
# Example: PLATON/ABSS
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min  0.9255
_exptl_absorpt_correction_T_max  0.9907

#===============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
;
;
_diffrn_ambient_temperature      290(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 area detector'
_diffrn_measurement_method       '\f and \w scans'

# number of measured reflections (redundant set)
_diffrn_reflns_number            6748
_diffrn_reflns_av_R_equivalents  0.0706
_diffrn_reflns_av_sigmaI/netI    0.0700
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.65
_diffrn_reflns_theta_max         25.00
_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_reduction_process 
;
;

_reflns_number_total             1796
_reflns_number_gt                1291
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 1998)'
_computing_cell_refinement       SMART
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)'
_computing_publication_material  'PLATON (Spek, 2003)'

#===============================================================================

# 8. REFINEMENT DATA

_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^)+(0.0397P)^2^+0.7164P] 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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1796
_refine_ls_number_parameters     155
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1259
_refine_ls_R_factor_gt           0.0853
_refine_ls_wR_factor_ref         0.1494
_refine_ls_wR_factor_gt          0.1356
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_restrained_S_all      1.148
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.046

#===============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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 -0.03373(14) -0.0139(7) 0.8954(5) 0.0654(11) Uani 1 1 d . . .
O1 O 0.03761(13) 0.6150(6) 0.6899(6) 0.0589(12) Uani 1 1 d . . .
F2 F 0.22522(13) 0.5366(8) 0.5750(6) 0.0891(14) Uani 1 1 d . . .
N1 N 0.05370(15) 0.1926(7) 0.7342(6) 0.0373(10) Uani 1 1 d . . .
C7 C 0.11101(19) 0.1972(9) 0.7357(8) 0.0389(12) Uani 1 1 d . . .
C6 C -0.0643(2) 0.1539(10) 0.8071(7) 0.0395(13) Uani 1 1 d . . .
C5 C -0.1197(2) 0.1256(11) 0.8195(8) 0.0539(17) Uani 1 1 d . . .
H5 H -0.1348 -0.0041 0.8824 0.065 Uiso 1 1 calc R . .
C12 C 0.1370(2) 0.0093(10) 0.8220(8) 0.0488(16) Uani 1 1 d . . .
H12 H 0.1166 -0.1112 0.8786 0.059 Uiso 1 1 calc R . .
C3 C -0.1283(2) 0.4879(10) 0.6441(7) 0.0484(16) Uani 1 1 d . . .
H3 H -0.1500 0.6008 0.5856 0.058 Uiso 1 1 calc R . .
C4 C -0.1522(2) 0.2975(10) 0.7347(9) 0.0495(14) Uani 1 1 d . . .
H4 H -0.1897 0.2838 0.7394 0.059 Uiso 1 1 calc R . .
C1 C -0.03992(19) 0.3444(8) 0.7208(7) 0.0384(12) Uani 1 1 d . . .
C2 C -0.0738(2) 0.5140(10) 0.6385(7) 0.0439(15) Uani 1 1 d . . .
H2 H -0.0587 0.6475 0.5786 0.053 Uiso 1 1 calc R . .
C13 C 0.02036(19) 0.3980(9) 0.7169(7) 0.0395(12) Uani 1 1 d . . .
C9 C 0.1955(2) 0.3586(12) 0.6563(9) 0.0592(19) Uani 1 1 d . . .
C10 C 0.2230(2) 0.1782(12) 0.7430(10) 0.069(2) Uani 1 1 d . . .
H10 H 0.2607 0.1782 0.7457 0.083 Uiso 1 1 calc R . .
C11 C 0.1936(2) -0.0057(12) 0.8272(10) 0.070(2) Uani 1 1 d . . .
H11 H 0.2110 -0.1350 0.8853 0.084 Uiso 1 1 calc R . .
C8 C 0.1411(2) 0.3785(10) 0.6476(7) 0.0457(15) Uani 1 1 d . . .
H8 H 0.1244 0.5059 0.5863 0.055 Uiso 1 1 calc R . .
H1N H 0.0413 0.0149 0.7758 0.068(18) Uiso 1 1 d 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 0.071(2) 0.057(2) 0.068(2) 0.0257(18) 0.0127(19) 0.0051(19)
O1 0.040(2) 0.0284(19) 0.108(4) 0.017(2) 0.008(2) -0.0090(17)
F2 0.062(2) 0.089(3) 0.117(4) 0.013(3) 0.013(2) -0.015(2)
N1 0.039(2) 0.029(2) 0.044(3) -0.003(2) -0.005(2) 0.0017(19)
C7 0.040(3) 0.030(3) 0.047(3) -0.010(3) -0.003(3) 0.006(2)
C6 0.045(3) 0.031(3) 0.042(3) 0.003(3) 0.002(3) 0.009(3)
C5 0.055(4) 0.037(3) 0.069(5) 0.007(4) 0.007(4) -0.012(3)
C12 0.039(3) 0.034(3) 0.073(5) -0.005(3) -0.005(3) 0.002(3)
C3 0.039(3) 0.047(4) 0.060(4) -0.003(3) -0.012(3) 0.012(3)
C4 0.032(3) 0.048(3) 0.068(4) -0.010(4) 0.008(4) -0.006(3)
C1 0.047(3) 0.025(3) 0.043(3) 0.001(3) 0.003(3) -0.009(2)
C2 0.046(3) 0.044(3) 0.042(4) 0.012(3) 0.003(3) 0.008(3)
C13 0.044(3) 0.035(3) 0.039(3) 0.008(3) 0.015(3) -0.010(2)
C9 0.056(4) 0.047(4) 0.075(5) 0.011(4) 0.024(3) -0.005(3)
C10 0.040(3) 0.067(4) 0.100(6) -0.010(5) 0.006(4) 0.004(3)
C11 0.056(4) 0.055(4) 0.099(6) -0.017(4) 0.003(4) -0.001(3)
C8 0.043(3) 0.037(3) 0.057(4) -0.004(3) -0.008(3) -0.002(3)

#===============================================================================

# 10. MOLECULAR GEOMETRY

_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
F1 C6 1.365(6) . ?
O1 C13 1.227(5) . ?
F2 C9 1.358(7) . ?
N1 C13 1.356(6) . ?
N1 C7 1.413(6) . ?
N1 H1N 1.0326 . ?
C7 C12 1.369(7) . ?
C7 C8 1.404(7) . ?
C6 C1 1.360(7) . ?
C6 C5 1.377(7) . ?
C5 C4 1.389(8) . ?
C5 H5 0.9300 . ?
C12 C11 1.398(8) . ?
C12 H12 0.9300 . ?
C3 C2 1.352(8) . ?
C3 C4 1.373(7) . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C1 C2 1.392(7) . ?
C1 C13 1.513(6) . ?
C2 H2 0.9300 . ?
C9 C8 1.347(8) . ?
C9 C10 1.360(8) . ?
C10 C11 1.387(9) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C8 H8 0.9300 . ?

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
C13 N1 C7 126.4(4) . . ?
C13 N1 H1N 124.1 . . ?
C7 N1 H1N 108.0 . . ?
C12 C7 C8 120.0(5) . . ?
C12 C7 N1 117.5(5) . . ?
C8 C7 N1 122.4(5) . . ?
C1 C6 F1 120.0(5) . . ?
C1 C6 C5 123.7(5) . . ?
F1 C6 C5 116.1(5) . . ?
C6 C5 C4 117.8(5) . . ?
C6 C5 H5 121.1 . . ?
C4 C5 H5 121.1 . . ?
C7 C12 C11 121.6(6) . . ?
C7 C12 H12 119.2 . . ?
C11 C12 H12 119.2 . . ?
C2 C3 C4 121.1(5) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C3 C4 C5 119.4(5) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C6 C1 C2 116.9(5) . . ?
C6 C1 C13 125.5(5) . . ?
C2 C1 C13 117.5(4) . . ?
C3 C2 C1 121.1(5) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
O1 C13 N1 122.3(4) . . ?
O1 C13 C1 120.9(4) . . ?
N1 C13 C1 116.6(4) . . ?
C8 C9 F2 117.2(6) . . ?
C8 C9 C10 125.3(6) . . ?
F2 C9 C10 117.5(6) . . ?
C9 C10 C11 118.6(6) . . ?
C9 C10 H10 120.7 . . ?
C11 C10 H10 120.7 . . ?
C10 C11 C12 117.9(7) . . ?
C10 C11 H11 121.1 . . ?
C12 C11 H11 121.1 . . ?
C9 C8 C7 116.6(5) . . ?
C9 C8 H8 121.7 . . ?
C7 C8 H8 121.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C13 N1 C7 C12 151.6(6) . . . . ?
C13 N1 C7 C8 -31.1(9) . . . . ?
C1 C6 C5 C4 2.0(9) . . . . ?
F1 C6 C5 C4 178.3(6) . . . . ?
C8 C7 C12 C11 1.0(9) . . . . ?
N1 C7 C12 C11 178.4(6) . . . . ?
C2 C3 C4 C5 -1.3(9) . . . . ?
C6 C5 C4 C3 -0.5(9) . . . . ?
F1 C6 C1 C2 -177.7(5) . . . . ?
C5 C6 C1 C2 -1.6(9) . . . . ?
F1 C6 C1 C13 -2.3(8) . . . . ?
C5 C6 C1 C13 173.8(6) . . . . ?
C4 C3 C2 C1 1.8(9) . . . . ?
C6 C1 C2 C3 -0.4(9) . . . . ?
C13 C1 C2 C3 -176.1(5) . . . . ?
C7 N1 C13 O1 4.7(9) . . . . ?
C7 N1 C13 C1 -179.4(6) . . . . ?
C6 C1 C13 O1 -152.7(6) . . . . ?
C2 C1 C13 O1 22.7(9) . . . . ?
C6 C1 C13 N1 31.4(8) . . . . ?
C2 C1 C13 N1 -153.2(5) . . . . ?
C8 C9 C10 C11 1.6(11) . . . . ?
F2 C9 C10 C11 180.0(6) . . . . ?
C9 C10 C11 C12 -1.8(10) . . . . ?
C7 C12 C11 C10 0.6(10) . . . . ?
F2 C9 C8 C7 -178.4(5) . . . . ?
C10 C9 C8 C7 0.0(10) . . . . ?
C12 C7 C8 C9 -1.3(8) . . . . ?
N1 C7 C8 C9 -178.5(5) . . . . ?

data_dc1_1_m
_database_code_depnum_ccdc_archive 'CCDC 285381'

#===============================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
; ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C13 H9 F2 N O'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural     ?
_chemical_formula_sum            'C13 H9 F2 N O'
_chemical_formula_iupac          ?
_chemical_formula_weight         233.21
_chemical_compound_source        ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_Int_Tables_number      19

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

_cell_length_a                   5.1864(14)
_cell_length_b                   5.8673(16)
_cell_length_c                   35.127(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1068.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    565
_cell_measurement_theta_min      1.2
_cell_measurement_theta_max      25.2
_cell_special_details            
; ?
;

_exptl_crystal_description       'plates '
_exptl_crystal_colour            ' colorless'

_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.53
_exptl_crystal_size_min          0.13
_exptl_crystal_size_rad          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             480
_exptl_absorpt_coefficient_mu    0.116
_exptl_crystal_density_meas_temp ?

# Permitted for _exptl_absorpt_correction_type :
# analytical 'analytical from crystal shape'
# Example: de Meulenaer&Tompa: ABST
# cylinder 'cylindrical'
# gaussian 'Gaussian from crystal shape'
# Example: PLATON/ABSG
# integration 'integration from crystal shape'
# multi-scan 'symmetry-related measurements'
# Example: SADABS, MULABS
# none 'no absorption corr. applied'
# numerical 'numerical from crystal shape'
# psi-scan 'psi-scan corrections'
# Example: PLATON/ABSP
# refdelf 'refined from delta-F'
# Example: SHELXA, DIFABS, DELABS
# sphere 'spherical'
# Example: PLATON/ABSS
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1997)'
_exptl_absorpt_correction_T_min  0.9056
_exptl_absorpt_correction_T_max  0.9851

#===============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
; ?
;
_diffrn_ambient_temperature      290(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 CCD area detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?

_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?

# number of measured reflections (redundant set)
_diffrn_reflns_number            7182
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_sigmaI/netI    0.0302
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_theta_min         1.16
_diffrn_reflns_theta_max         27.14
_diffrn_measured_fraction_theta_max 0.956
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_reduction_process 
; ?
;

_reflns_number_total             1829
_reflns_number_gt                1551
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 1998)'
_computing_cell_refinement       SMART
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)'
_computing_publication_material  'PLATON (Spek, 2003)'

#===============================================================================

# 8. REFINEMENT DATA

_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^)+(0.0000P)^2^+2.0915P] 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_number_reflns         1829
_refine_ls_number_parameters     158
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0890
_refine_ls_R_factor_gt           0.0760
_refine_ls_wR_factor_ref         0.1350
_refine_ls_wR_factor_gt          0.1310
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.090
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.044

#===============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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
F2 F 0.0184(8) -0.0586(7) 0.19142(10) 0.0926(13) Uani 1 1 d . . .
F1 F 0.0537(8) 0.3493(7) 0.11935(11) 0.0925(13) Uani 1 1 d . . .
O1 O 0.7136(7) -0.0850(7) 0.10701(12) 0.0763(13) Uani 1 1 d . . .
C7 C 0.3742(13) -0.2365(9) 0.16280(15) 0.0598(17) Uani 1 1 d . . .
C1 C 0.4032(12) 0.2062(9) 0.08382(15) 0.0547(14) Uani 1 1 d . . .
C12 C 0.1972(13) -0.2307(10) 0.19144(18) 0.0642(15) Uani 1 1 d . . .
C5 C 0.1715(12) 0.5454(10) 0.06452(17) 0.0656(16) Uani 1 1 d . . .
H5 H 0.0421 0.6514 0.0693 0.079 Uiso 1 1 calc R . .
C11 C 0.1908(11) -0.3848(10) 0.21956(17) 0.0648(16) Uani 1 1 d . . .
H11 H 0.0691 -0.3735 0.2389 0.078 Uiso 1 1 calc R . .
C2 C 0.5578(12) 0.2334(11) 0.05202(16) 0.0660(16) Uani 1 1 d . . .
H2 H 0.6906 0.1300 0.0478 0.079 Uiso 1 1 calc R . .
N1 N 0.3268(11) -0.0435(14) 0.1326(2) 0.106(3) Uani 1 1 d . . .
C6 C 0.2102(12) 0.3660(10) 0.08834(15) 0.0586(14) Uani 1 1 d . . .
C10 C 0.3670(11) -0.5602(11) 0.21941(19) 0.0711(17) Uani 1 1 d . . .
H10 H 0.3616 -0.6718 0.2382 0.085 Uiso 1 1 calc R . .
C3 C 0.5217(11) 0.4066(10) 0.02680(16) 0.0637(15) Uani 1 1 d . . .
H3 H 0.6260 0.4180 0.0053 0.076 Uiso 1 1 calc R . .
C8 C 0.5555(12) -0.4089(11) 0.16218(18) 0.0714(17) Uani 1 1 d . . .
H8 H 0.6775 -0.4178 0.1428 0.086 Uiso 1 1 calc R . .
C4 C 0.3294(12) 0.5659(10) 0.03317(17) 0.0657(16) Uani 1 1 d . . .
H4 H 0.3069 0.6865 0.0163 0.079 Uiso 1 1 calc R . .
C9 C 0.5499(11) -0.5693(11) 0.19146(18) 0.0685(16) Uani 1 1 d . . .
H9 H 0.6729 -0.6845 0.1920 0.082 Uiso 1 1 calc R . .
C13 C 0.4986(12) -0.0042(13) 0.1111(2) 0.091(3) Uani 1 1 d . . .
H1N H 0.183(12) 0.002(10) 0.1367(16) 0.11(2) Uiso 1 1 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
F2 0.109(3) 0.076(2) 0.093(3) -0.011(2) -0.017(2) 0.031(3)
F1 0.092(3) 0.092(3) 0.094(3) -0.012(2) 0.022(2) -0.007(2)
O1 0.042(2) 0.084(3) 0.103(3) 0.007(3) 0.017(2) 0.019(2)
C7 0.098(5) 0.036(3) 0.046(3) -0.003(2) -0.027(3) -0.008(3)
C1 0.072(4) 0.038(3) 0.054(3) -0.004(2) -0.016(3) 0.002(3)
C12 0.065(4) 0.061(4) 0.067(4) -0.008(3) -0.013(3) 0.001(3)
C5 0.059(3) 0.055(3) 0.083(4) -0.010(3) -0.011(3) 0.007(3)
C11 0.058(3) 0.072(4) 0.064(3) 0.007(3) -0.007(3) -0.005(3)
C2 0.065(4) 0.069(4) 0.064(3) -0.007(3) -0.005(3) 0.008(3)
N1 0.046(3) 0.136(6) 0.134(6) -0.081(5) 0.018(4) 0.004(4)
C6 0.067(3) 0.059(3) 0.049(3) -0.015(3) 0.007(3) -0.016(3)
C10 0.056(3) 0.059(4) 0.098(5) 0.018(4) -0.010(3) -0.009(3)
C3 0.061(3) 0.064(4) 0.067(4) 0.007(3) 0.009(3) 0.001(3)
C8 0.066(4) 0.072(4) 0.076(4) -0.012(4) 0.005(3) -0.018(4)
C4 0.073(4) 0.057(3) 0.067(4) 0.005(3) -0.013(3) -0.007(3)
C9 0.051(3) 0.063(4) 0.091(4) 0.001(4) -0.012(3) 0.000(3)
C13 0.047(3) 0.112(6) 0.114(6) -0.075(5) 0.008(4) -0.011(4)

#===============================================================================

# 10. MOLECULAR GEOMETRY

_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
F2 C12 1.371(7) . ?
F1 C6 1.362(6) . ?
O1 C13 1.221(7) . ?
C7 C12 1.362(8) . ?
C7 C8 1.381(8) . ?
C7 N1 1.569(9) . ?
C1 C6 1.381(8) . ?
C1 C2 1.384(8) . ?
C1 C13 1.640(9) . ?
C12 C11 1.340(8) . ?
C5 C6 1.359(8) . ?
C5 C4 1.378(8) . ?
C5 H5 0.9300 . ?
C11 C10 1.376(8) . ?
C11 H11 0.9300 . ?
C2 C3 1.361(8) . ?
C2 H2 0.9300 . ?
N1 C13 1.191(9) . ?
N1 H1N 0.80(6) . ?
C10 C9 1.366(8) . ?
C10 H10 0.9300 . ?
C3 C4 1.385(8) . ?
C3 H3 0.9300 . ?
C8 C9 1.394(8) . ?
C8 H8 0.9300 . ?
C4 H4 0.9300 . ?
C9 H9 0.9300 . ?

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
C12 C7 C8 119.2(6) . . ?
C12 C7 N1 112.0(6) . . ?
C8 C7 N1 128.6(6) . . ?
C6 C1 C2 115.7(5) . . ?
C6 C1 C13 131.5(5) . . ?
C2 C1 C13 112.6(5) . . ?
C11 C12 C7 123.0(6) . . ?
C11 C12 F2 118.7(6) . . ?
C7 C12 F2 118.3(6) . . ?
C6 C5 C4 118.2(6) . . ?
C6 C5 H5 120.9 . . ?
C4 C5 H5 120.9 . . ?
C12 C11 C10 119.1(6) . . ?
C12 C11 H11 120.5 . . ?
C10 C11 H11 120.5 . . ?
C3 C2 C1 122.1(6) . . ?
C3 C2 H2 118.9 . . ?
C1 C2 H2 118.9 . . ?
C13 N1 C7 116.8(7) . . ?
C13 N1 H1N 138(5) . . ?
C7 N1 H1N 106(4) . . ?
C5 C6 F1 117.4(6) . . ?
C5 C6 C1 124.2(5) . . ?
F1 C6 C1 118.4(5) . . ?
C9 C10 C11 119.5(6) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C2 C3 C4 119.9(6) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C7 C8 C9 117.9(6) . . ?
C7 C8 H8 121.0 . . ?
C9 C8 H8 121.0 . . ?
C5 C4 C3 119.9(6) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C10 C9 C8 121.2(6) . . ?
C10 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
N1 C13 O1 133.1(9) . . ?
N1 C13 C1 106.9(7) . . ?
O1 C13 C1 119.9(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 C7 C12 C11 0.5(9) . . . . ?
N1 C7 C12 C11 176.8(5) . . . . ?
C8 C7 C12 F2 -179.7(5) . . . . ?
N1 C7 C12 F2 -3.4(7) . . . . ?
C7 C12 C11 C10 -1.3(9) . . . . ?
F2 C12 C11 C10 178.9(5) . . . . ?
C6 C1 C2 C3 -0.1(8) . . . . ?
C13 C1 C2 C3 -176.0(5) . . . . ?
C12 C7 N1 C13 164.9(6) . . . . ?
C8 C7 N1 C13 -19.2(9) . . . . ?
C4 C5 C6 F1 179.5(5) . . . . ?
C4 C5 C6 C1 2.1(9) . . . . ?
C2 C1 C6 C5 -1.9(8) . . . . ?
C13 C1 C6 C5 173.1(5) . . . . ?
C2 C1 C6 F1 -179.3(5) . . . . ?
C13 C1 C6 F1 -4.3(8) . . . . ?
C12 C11 C10 C9 2.3(9) . . . . ?
C1 C2 C3 C4 1.7(9) . . . . ?
C12 C7 C8 C9 -0.6(8) . . . . ?
N1 C7 C8 C9 -176.3(5) . . . . ?
C6 C5 C4 C3 -0.3(9) . . . . ?
C2 C3 C4 C5 -1.5(9) . . . . ?
C11 C10 C9 C8 -2.5(9) . . . . ?
C7 C8 C9 C10 1.7(9) . . . . ?
C7 N1 C13 O1 0.3(11) . . . . ?
C7 N1 C13 C1 -178.5(4) . . . . ?
C6 C1 C13 N1 19.1(8) . . . . ?
C2 C1 C13 N1 -165.7(6) . . . . ?
C6 C1 C13 O1 -159.8(6) . . . . ?
C2 C1 C13 O1 15.3(7) . . . . ?

data_dc3_3
_database_code_depnum_ccdc_archive 'CCDC 644095'

#===============================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H9 F2 N O'
_chemical_formula_structural     ?
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_sum            'C13 H9 F2 N O'
_chemical_formula_weight         233.21
_chemical_compound_source        ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z

_cell_length_a                   5.460(2)
_cell_length_b                   7.693(3)
_cell_length_c                   13.038(5)
_cell_angle_alpha                106.758(6)
_cell_angle_beta                 100.371(6)
_cell_angle_gamma                90.016(6)
_cell_volume                     515.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    655
_cell_measurement_theta_min      1.4
_cell_measurement_theta_max      26.4
_cell_special_details            
; ?
;

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless

_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.09
_exptl_crystal_size_rad          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             240
_exptl_absorpt_coefficient_mu    0.120
_exptl_crystal_density_meas_temp ?

# Permitted for _exptl_absorpt_correction_type :
# analytical 'analytical from crystal shape'
# cylinder 'cylindrical'
# empirical 'empirical from intensities'
# gaussian 'Gaussian from crystal shape'
# integration 'integration from crystal shape'
# multi-scan 'symmetry-related measurements'
# none 'no absorption corr. applied'
# numerical 'numerical from crystal shape'
# psi-scan 'psi-scan corrections'
# refdelf 'refined from delta-F'
# sphere 'spherical'
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min  0.8903
_exptl_absorpt_correction_T_max  0.9892

#===============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
; ?
;
_diffrn_ambient_temperature      290(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 CCD area detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?

_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?

# number of measured reflections (redundant set)
_diffrn_reflns_number            3767
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_sigmaI/netI    0.0331
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.66
_diffrn_reflns_theta_max         25.35
_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_reduction_process 
;
?
;

_reflns_number_total             1862
_reflns_number_gt                1431
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       'SMART (Bruker, 1998)'
_computing_cell_refinement       SMART
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)'
_computing_publication_material  'PLATON (Spek, 2003)'

#===============================================================================

# 8. REFINEMENT DATA

_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^)+(0.0939P)^2^+0.2360P] 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         1862
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0786
_refine_ls_R_factor_gt           0.0612
_refine_ls_wR_factor_ref         0.1729
_refine_ls_wR_factor_gt          0.1625
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.450
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.060

#===============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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
N1 N 0.1886(4) 0.7452(3) 0.96604(19) 0.0413(6) Uani 1 1 d . . .
F2 F -0.0270(3) 0.7179(3) 0.53203(13) 0.0614(6) Uani 1 1 d . . .
F1 F 0.4421(3) 0.7800(3) 1.46567(13) 0.0619(6) Uani 1 1 d . . .
C11 C -0.1283(5) 0.8064(4) 0.7066(2) 0.0410(7) Uani 1 1 d . . .
C5 C 0.2241(5) 0.6886(4) 1.2854(2) 0.0420(7) Uani 1 1 d . . .
C8 C 0.3031(5) 0.6574(4) 0.7831(2) 0.0386(6) Uani 1 1 d . . .
C3 C 0.6241(5) 0.8539(4) 1.3326(2) 0.0410(7) Uani 1 1 d . . .
C13 C 0.4144(5) 0.7532(4) 1.0308(2) 0.0402(6) Uani 1 1 d . . .
C1 C 0.4073(5) 0.7606(3) 1.1461(2) 0.0354(6) Uani 1 1 d . . .
C10 C 0.0300(5) 0.7250(4) 0.6382(2) 0.0385(6) Uani 1 1 d . . .
C6 C 0.2124(5) 0.6829(4) 1.1779(2) 0.0401(6) Uani 1 1 d . . .
C7 C 0.1452(5) 0.7397(3) 0.8544(2) 0.0348(6) Uani 1 1 d . . .
O1 O 0.6121(3) 0.7552(3) 0.99884(15) 0.0525(6) Uani 1 1 d . . .
C2 C 0.6107(5) 0.8444(4) 1.2253(2) 0.0387(6) Uani 1 1 d . . .
C12 C -0.0684(5) 0.8142(4) 0.8146(2) 0.0382(6) Uani 1 1 d . . .
C9 C 0.2438(5) 0.6499(4) 0.6747(2) 0.0409(7) Uani 1 1 d . . .
C4 C 0.4286(5) 0.7742(4) 1.3608(2) 0.0380(6) Uani 1 1 d . . .
H8 H 0.442(6) 0.605(4) 0.810(2) 0.045(8) Uiso 1 1 d . . .
H9 H 0.335(6) 0.591(4) 0.625(2) 0.041(7) Uiso 1 1 d . . .
H12 H -0.176(6) 0.877(4) 0.867(2) 0.045(7) Uiso 1 1 d . . .
H11 H -0.278(6) 0.865(4) 0.680(2) 0.055(9) Uiso 1 1 d . . .
H6 H 0.062(6) 0.621(4) 1.122(2) 0.054(8) Uiso 1 1 d . . .
H1N H 0.067(7) 0.763(4) 1.008(2) 0.057(9) Uiso 1 1 d . . .
H5 H 0.094(6) 0.635(4) 1.310(2) 0.050(8) Uiso 1 1 d . . .
H3 H 0.754(7) 0.911(5) 1.391(3) 0.070(10) Uiso 1 1 d . . .
H2 H 0.744(6) 0.909(4) 1.202(2) 0.061(9) Uiso 1 1 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
N1 0.0316(12) 0.0505(15) 0.0439(13) 0.0146(11) 0.0114(10) 0.0015(10)
F2 0.0496(10) 0.0951(15) 0.0437(10) 0.0295(9) 0.0047(8) 0.0011(9)
F1 0.0522(11) 0.0976(15) 0.0430(10) 0.0284(10) 0.0143(8) -0.0010(10)
C11 0.0290(13) 0.0460(16) 0.0526(17) 0.0220(14) 0.0071(12) -0.0004(11)
C5 0.0332(14) 0.0462(16) 0.0543(17) 0.0219(13) 0.0160(12) 0.0003(12)
C8 0.0303(13) 0.0440(16) 0.0418(15) 0.0145(12) 0.0045(11) 0.0034(11)
C3 0.0310(13) 0.0487(17) 0.0418(16) 0.0116(13) 0.0058(11) -0.0031(11)
C13 0.0320(14) 0.0434(16) 0.0446(15) 0.0112(12) 0.0083(11) -0.0023(11)
C1 0.0343(13) 0.0342(14) 0.0408(15) 0.0133(11) 0.0108(11) 0.0008(10)
C10 0.0328(13) 0.0477(16) 0.0368(14) 0.0170(12) 0.0036(11) -0.0070(11)
C6 0.0294(13) 0.0443(16) 0.0457(16) 0.0130(12) 0.0048(11) -0.0011(11)
C7 0.0343(13) 0.0353(14) 0.0350(14) 0.0097(11) 0.0077(10) -0.0056(10)
O1 0.0287(10) 0.0887(16) 0.0428(11) 0.0203(10) 0.0123(8) -0.0041(9)
C2 0.0310(13) 0.0448(16) 0.0416(15) 0.0129(12) 0.0098(11) -0.0016(11)
C12 0.0324(13) 0.0359(14) 0.0486(16) 0.0122(12) 0.0137(12) 0.0001(11)
C9 0.0323(14) 0.0465(16) 0.0419(16) 0.0067(13) 0.0126(12) -0.0007(12)
C4 0.0347(14) 0.0494(16) 0.0336(14) 0.0159(12) 0.0100(11) 0.0076(11)

#===============================================================================

# 10. MOLECULAR GEOMETRY

_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
N1 C13 1.354(4) . ?
N1 C7 1.421(3) . ?
N1 H1N 0.92(3) . ?
F2 C10 1.348(3) . ?
F1 C4 1.344(3) . ?
C11 C12 1.370(4) . ?
C11 C10 1.375(4) . ?
C11 H11 0.99(3) . ?
C5 C4 1.370(4) . ?
C5 C6 1.379(4) . ?
C5 H5 0.97(3) . ?
C8 C9 1.376(4) . ?
C8 C7 1.399(4) . ?
C8 H8 0.92(3) . ?
C3 C2 1.368(4) . ?
C3 C4 1.386(4) . ?
C3 H3 0.95(4) . ?
C13 O1 1.227(3) . ?
C13 C1 1.495(4) . ?
C1 C2 1.385(4) . ?
C1 C6 1.402(4) . ?
C10 C9 1.372(4) . ?
C6 H6 1.00(3) . ?
C7 C12 1.383(4) . ?
C2 H2 1.02(3) . ?
C12 H12 1.00(3) . ?
C9 H9 0.90(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
C13 N1 C7 126.0(2) . . ?
C13 N1 H1N 109.1(19) . . ?
C7 N1 H1N 124.2(19) . . ?
C12 C11 C10 118.8(2) . . ?
C12 C11 H11 120.0(18) . . ?
C10 C11 H11 121.0(18) . . ?
C4 C5 C6 118.7(2) . . ?
C4 C5 H5 118.5(17) . . ?
C6 C5 H5 122.8(17) . . ?
C9 C8 C7 120.0(3) . . ?
C9 C8 H8 121.5(18) . . ?
C7 C8 H8 118.5(18) . . ?
C2 C3 C4 118.2(2) . . ?
C2 C3 H3 127(2) . . ?
C4 C3 H3 115(2) . . ?
O1 C13 N1 123.3(3) . . ?
O1 C13 C1 121.7(2) . . ?
N1 C13 C1 115.1(2) . . ?
C2 C1 C6 118.4(2) . . ?
C2 C1 C13 117.5(2) . . ?
C6 C1 C13 124.1(2) . . ?
F2 C10 C9 119.0(2) . . ?
F2 C10 C11 119.1(2) . . ?
C9 C10 C11 121.9(2) . . ?
C5 C6 C1 120.7(2) . . ?
C5 C6 H6 118.9(17) . . ?
C1 C6 H6 120.3(17) . . ?
C12 C7 C8 119.2(2) . . ?
C12 C7 N1 117.7(2) . . ?
C8 C7 N1 123.1(2) . . ?
C3 C2 C1 121.8(2) . . ?
C3 C2 H2 120.5(18) . . ?
C1 C2 H2 117.5(17) . . ?
C11 C12 C7 120.9(2) . . ?
C11 C12 H12 120.5(16) . . ?
C7 C12 H12 118.5(16) . . ?
C10 C9 C8 119.2(3) . . ?
C10 C9 H9 118.0(17) . . ?
C8 C9 H9 122.7(17) . . ?
F1 C4 C5 119.1(2) . . ?
F1 C4 C3 118.6(2) . . ?
C5 C4 C3 122.3(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N1 C13 O1 -0.6(4) . . . . ?
C7 N1 C13 C1 179.1(2) . . . . ?
O1 C13 C1 C2 26.8(4) . . . . ?
N1 C13 C1 C2 -152.9(3) . . . . ?
O1 C13 C1 C6 -150.9(3) . . . . ?
N1 C13 C1 C6 29.4(4) . . . . ?
C12 C11 C10 F2 -179.6(2) . . . . ?
C12 C11 C10 C9 0.8(4) . . . . ?
C4 C5 C6 C1 1.0(4) . . . . ?
C2 C1 C6 C5 -0.6(4) . . . . ?
C13 C1 C6 C5 177.2(2) . . . . ?
C9 C8 C7 C12 -0.6(4) . . . . ?
C9 C8 C7 N1 177.1(2) . . . . ?
C13 N1 C7 C12 -150.5(3) . . . . ?
C13 N1 C7 C8 31.7(4) . . . . ?
C4 C3 C2 C1 1.0(4) . . . . ?
C6 C1 C2 C3 -0.5(4) . . . . ?
C13 C1 C2 C3 -178.3(3) . . . . ?
C10 C11 C12 C7 -0.9(4) . . . . ?
C8 C7 C12 C11 0.8(4) . . . . ?
N1 C7 C12 C11 -177.0(2) . . . . ?
F2 C10 C9 C8 179.8(2) . . . . ?
C11 C10 C9 C8 -0.6(4) . . . . ?
C7 C8 C9 C10 0.5(4) . . . . ?
C6 C5 C4 F1 -179.8(2) . . . . ?
C6 C5 C4 C3 -0.5(4) . . . . ?
C2 C3 C4 F1 178.8(2) . . . . ?
C2 C3 C4 C5 -0.5(4) . . . . ?

#===END

