# Electronic Supplementary Material (ESI) for CrystEngComm
# This journal is © The Royal Society of Chemistry 2011


data_global
_journal_name_full               CrystEngComm
_journal_coden_cambridge         1350
#TrackingRef '- Compound 1 cif.cif'

#------------------ AUDIT DETAILS -------------------------------------------#

_audit_creation_date             2011-02-24
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_update_record             ?

#------------------ SUBMISSION DETAILS --------------------------------------#

# Name and address of author for correspondence

_publ_contact_author_name        'ALLAIN, Magali'
_publ_contact_author_address     
;
MOLTECH ANJOU UMR CNRS 6200
2, bd Lavoisier
49045 Angers cedex
France

;
_publ_contact_author_email       magali.allain@univ-angers.fr
_publ_contact_author_fax         33(0)241735405
_publ_contact_author_phone       33(0)241735368
_publ_requested_coeditor_name    ?
_publ_contact_letter             # Include date of submission
;
Date of submission ?

Please consider this CIF submission for publication as a
Regular Structural Paper in Acta Crystallographica C.
;
_publ_requested_category         ?

#------------------ PROCESSING SUMMARY (JOURNAL OFFICE ONLY) ----------------#

_journal_date_recd_electronic    ?
_journal_date_to_coeditor        ?
_journal_date_from_coeditor      ?
_journal_date_accepted           ?
_journal_date_printers_first     ?
_journal_date_printers_final     ?
_journal_date_proofs_out         ?
_journal_date_proofs_in          ?
_journal_coeditor_name           ?
_journal_coeditor_code           ?
_journal_coeditor_notes          ?
_journal_techeditor_code         ?
_journal_techeditor_notes        ?
_journal_coden_ASTM              ?
_journal_year                    ?
_journal_volume                  ?
_journal_issue                   ?
_journal_page_first              ?
_journal_page_last               ?
_journal_suppl_publ_number       ?
_journal_suppl_publ_pages        ?

#------------------ TITLE AND AUTHOR LIST------------------------------------#

_publ_section_title              
;
?
;

_publ_section_title_footnote     
;
?
;

loop_
_publ_author_name
_publ_author_address
C.Mallet
;
MOLTECH ANJOU UMR CNRS 6200
2, bd Lavoisier
49045 Angers cedex
France
;
M.Allain ''
P.Leriche ''
P.Frere ''

#------------------ TEXT ----------------------------------------------------#

_publ_section_synopsis           
;
# Insert blank lines between paragraphs
?
;
_publ_section_abstract           
;
# Insert blank lines between paragraphs
?
;

_publ_section_comment            
;
# Insert blank lines between paragraphs
?
;

_publ_section_exptl_prep         
;
?
;

_publ_section_exptl_refinement   
;
?
;

# Insert blank lines between references

_publ_section_references         
;
Allen, F.H., Kennard, O. & Taylor, R. (1983).
Acc. Chem. Res. 16, 146-153.

Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A.
(1993) J. Appl. Cryst. 26, 343-350.

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.

Blessing, R. H. (1995) Acta Cryst., A51, 33-38.

Blessing, R. H. (1987) Cryst. Rev. 1, 3-58.

Blessing, R. H. (1989) J. Appl. Cryst. 22, 396-397.

Beurskens, P.T., Beurskens, G., de Gelder, R.,
Garci\'ia-Granda, S., Gould, R.O., Israel, R. & Smits, J.M.M.
(1999) The DIRDIF-99 program system,
Technical Report of the Crystallography Laboratory,
University of Nijmegen, The Netherlands.

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

Enraf-Nonius (1994). CAD4Express Software. Enraf-Nonius, Delft,
The Netherlands.

Farrugia, L. J. (1997) ORTEP-3 for Windows, J. Appl. Cryst. 30, 565.

Farrugia, L. J. (1999) WinGX, J. Appl. Cryst. 32, 837-838.

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

Harms, K. & Wocadlo, S. (1995) XCAD-4. Program for Processing CAD-4
Diffractometer Data. University of Marburg, Germany.

Johnson, C.K. (1965). ORTEP. Report ORNL-3794. Oak Ridge National
Laboratory, Tennessee, USA.

Lehman, M. S. and Larsen, F. K. (1974) Acta. Cryst. A30, 580

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

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

Orpen, A. G., Brammer, L., Allen, F. H., Kennard, O., Watson, D. G.,
& Taylor, R. (1992). International Tables for Crystallography,
Volume C.

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

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

Sheldrick, G.M. (1985). SHELXS86. In Crystallographic Computing 3,
edited by G. M. Sheldrick, C. Kruger & R. Goddard, pp. 175-189.
Oxford University Press.

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

Spek, A.L. (1990). Acta Cryst. A46, C34

Streltsov, V. A. & Zavodnik, V. E. (1989) Sov. Phys. Crystallogr.
34, 824-828

Streltsov, V. A. & Zavodnik, V. E. (1990) Sov. Phys. Crystallogr.
35, 281.

Walker, N. & Stuart, D. (1983). Acta Cryst., A39, 158 - 166.

Wilson, A.J.C. (1992) Ed. International Tables for Crystallography,
Volume C, Kluwer Academic Publishers, Dordrecht, The Netherlands.
;
_publ_section_figure_captions    
;
Figure 1. View of (I) (50% probability displacement ellipsoids)
;
_publ_section_acknowledgements   
;
?
;
_publ_section_table_legends      
;
Table 1. Fractional atomic coordinates and equivalent
isotropic displacement parameters (\%A^2^)

Table 2. Selected geometric parameters (\%A ,\% )
;

#------------------ SECTION 2. COMPOUND(S) DETAILS -------------------------#

data_compound1
_database_code_depnum_ccdc_archive 'CCDC 818758'
#TrackingRef '- Compound 1 cif.cif'

_audit_creation_date             2011-02-24T18:29:16-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#------------------ CHEMICAL INFORMATION ------------------------------------#

_chemical_formula_moiety         'C18 H14 N2 O1'
_chemical_formula_sum            'C18 H14 N2 O'
_chemical_formula_weight         274.31

#------------------ UNIT CELL INFORMATION -----------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   31.930(8)
_cell_length_b                   6.041(2)
_cell_length_c                   7.424(1)
_cell_angle_alpha                90
_cell_angle_beta                 97.04(1)
_cell_angle_gamma                90
_cell_volume                     1421.2(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1776
_cell_measurement_theta_min      3.43
_cell_measurement_theta_max      28.05

#------------------ CRYSTAL INFORMATION -------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.03
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             576
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.553
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_process_details   
;
'(SADABS (Sheldrick, Bruker, 2000))'
;

#------------------ DATA COLLECTION INFORMATION -----------------------------#

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  'horizontally mounted graphite crystal'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            7548
_diffrn_reflns_av_R_equivalents  0.0766
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.43
_diffrn_reflns_theta_max         28.05
_diffrn_reflns_theta_full        28.05
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measured_fraction_theta_full 0.956
_reflns_number_total             1644
_reflns_number_gt                971
_reflns_threshold_expression     >2sigma(I)

#------------------ COMPUTER PROGRAMS USED ----------------------------------#

_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_structure_solution    'Direct methods (Sir92,Altomare et al.,1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'DIAMOND 3.2d (Crystal Impact GbR 2005)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#------------------ REFINEMENT INFORMATION ----------------------------------#

_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^)+(0.0239P)^2^+1.0622P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1644
_refine_ls_number_parameters     124
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0577
_refine_ls_wR_factor_ref         0.1146
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_restrained_S_all      1.108
_refine_ls_shift/su_max          0
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.211

#------------------ ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS --------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
_atom_site_disorder_assembly
C1 C 0.48024(6) 0.3799(4) 0.6970(3) 0.0399(5) Uani 1 d . . .
C2 C 0.46915(6) 0.1648(3) 0.6690(3) 0.0359(5) Uani 1 d . . .
C3 C 0.43044(6) 0.0730(3) 0.5785(3) 0.0372(5) Uani 1 d . . .
C4 C 0.37913(6) -0.1864(3) 0.4912(3) 0.0343(5) Uani 1 d . . .
C5 C 0.37339(7) -0.3808(3) 0.3904(3) 0.0408(5) Uani 1 d . . .
C6 C 0.33347(8) -0.4445(4) 0.3160(3) 0.0503(6) Uani 1 d . . .
C7 C 0.29889(8) -0.3155(4) 0.3418(3) 0.0537(7) Uani 1 d . . .
C8 C 0.30404(7) -0.1236(4) 0.4422(3) 0.0479(6) Uani 1 d . . .
C9 C 0.34399(7) -0.0584(4) 0.5171(3) 0.0401(5) Uani 1 d . . .
N1 N 0.42068(5) -0.1315(3) 0.5720(2) 0.0368(4) Uani 1 d . . .
O1 O 0.5 0.0267(3) 0.75 0.0358(5) Uani 1 d S . .
H1 H 0.4640(7) 0.503(4) 0.652(3) 0.048(6) Uiso 1 d . . .
H3 H 0.4118(6) 0.187(3) 0.521(3) 0.041(6) Uiso 1 d . . .
H5 H 0.3978(7) -0.473(3) 0.374(3) 0.041(6) Uiso 1 d . . .
H6 H 0.3308(7) -0.578(4) 0.247(3) 0.054(7) Uiso 1 d . . .
H7 H 0.2722(7) -0.365(4) 0.294(3) 0.064(7) Uiso 1 d . . .
H8 H 0.2797(8) -0.029(4) 0.464(3) 0.063(8) Uiso 1 d . . .
H9 H 0.3475(6) 0.074(3) 0.597(3) 0.046(6) Uiso 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
C1 0.0368(11) 0.0322(11) 0.0510(13) 0.0062(9) 0.0063(9) 0.0034(9)
C2 0.0318(11) 0.0339(12) 0.0413(11) 0.0045(9) 0.0024(8) 0.0031(9)
C3 0.0355(12) 0.0336(12) 0.0417(12) 0.0044(9) 0.0016(9) 0.0027(9)
C4 0.0349(11) 0.0329(11) 0.0342(10) 0.0053(8) 0.0007(9) 0.0009(9)
C5 0.0479(13) 0.0350(12) 0.0400(12) 0.0015(9) 0.0078(10) 0.0005(10)
C6 0.0610(16) 0.0483(15) 0.0414(13) -0.0057(10) 0.0057(11) -0.0152(12)
C7 0.0428(14) 0.0740(18) 0.0425(13) -0.0010(12) -0.0027(11) -0.0195(14)
C8 0.0363(12) 0.0620(16) 0.0451(13) 0.0017(11) 0.0035(10) -0.0028(12)
C9 0.0392(12) 0.0410(13) 0.0392(12) -0.0009(9) 0.0012(9) 0.0019(10)
N1 0.0342(9) 0.0345(10) 0.0407(10) 0.0004(7) 0.0009(8) 0.0038(8)
O1 0.0327(11) 0.0313(11) 0.0415(11) 0 -0.0026(9) 0

#------------------ 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
C1 C2 1.357(3) . ?
C1 C1 1.403(4) 2_656 ?
C1 H1 0.94(2) . ?
C2 O1 1.372(2) . ?
C2 C3 1.443(3) . ?
C3 N1 1.274(3) . ?
C3 H3 0.98(2) . ?
C4 C5 1.393(3) . ?
C4 C9 1.396(3) . ?
C4 N1 1.426(2) . ?
C5 C6 1.380(3) . ?
C5 H5 0.98(2) . ?
C6 C7 1.384(3) . ?
C6 H6 0.95(2) . ?
C7 C8 1.377(3) . ?
C7 H7 0.93(2) . ?
C8 C9 1.385(3) . ?
C8 H8 0.99(2) . ?
C9 H9 0.99(2) . ?
O1 C2 1.372(2) 2_656 ?

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
C2 C1 C1 106.62(12) . 2_656 ?
C2 C1 H1 125.3(13) . . ?
C1 C1 H1 128.1(13) 2_656 . ?
C1 C2 O1 110.81(17) . . ?
C1 C2 C3 129.20(18) . . ?
O1 C2 C3 119.91(17) . . ?
N1 C3 C2 125.60(18) . . ?
N1 C3 H3 122.5(11) . . ?
C2 C3 H3 111.9(11) . . ?
C5 C4 C9 119.09(19) . . ?
C5 C4 N1 118.46(18) . . ?
C9 C4 N1 122.37(18) . . ?
C6 C5 C4 120.3(2) . . ?
C6 C5 H5 120.0(12) . . ?
C4 C5 H5 119.7(12) . . ?
C5 C6 C7 120.0(2) . . ?
C5 C6 H6 117.9(14) . . ?
C7 C6 H6 122.1(14) . . ?
C8 C7 C6 120.3(2) . . ?
C8 C7 H7 121.5(15) . . ?
C6 C7 H7 118.1(15) . . ?
C7 C8 C9 120.0(2) . . ?
C7 C8 H8 121.9(14) . . ?
C9 C8 H8 118.1(14) . . ?
C8 C9 C4 120.2(2) . . ?
C8 C9 H9 120.1(12) . . ?
C4 C9 H9 119.6(12) . . ?
C3 N1 C4 116.90(16) . . ?
C2 O1 C2 105.1(2) 2_656 . ?

# Attachment '- Compound 3 cif.cif'

data_compound3
_database_code_depnum_ccdc_archive 'CCDC 818759'
#TrackingRef '- Compound 3 cif.cif'

_audit_creation_date             2010-04-16T10:06:00-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#------------------ CHEMICAL INFORMATION ------------------------------------#

_chemical_formula_moiety         'C24 H8 F10 N2 O2'
_chemical_formula_sum            'C24 H8 F10 N2 O2'
_chemical_formula_weight         546.32

#------------------ UNIT CELL INFORMATION -----------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.4323(9)
_cell_length_b                   7.278(1)
_cell_length_c                   22.578(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.06(1)
_cell_angle_gamma                90
_cell_volume                     1055.5(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3857
_cell_measurement_theta_min      3.57
_cell_measurement_theta_max      29

#------------------ CRYSTAL INFORMATION -------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    1.719
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544
_exptl_absorpt_coefficient_mu    0.171
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.9722
_exptl_absorpt_correction_T_max  0.9918
_exptl_absorpt_process_details   
;
PLATON-ABSGAUSS : Spek, A.L. (2003), J.Appl.Cryst. 36, 7-13
;

#------------------ DATA COLLECTION INFORMATION -----------------------------#

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            19128
_diffrn_reflns_av_R_equivalents  0.0991
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         3.61
_diffrn_reflns_theta_max         29
_diffrn_reflns_theta_full        26
_diffrn_measured_fraction_theta_max 0.939
_diffrn_measured_fraction_theta_full 0.984
_reflns_number_total             2630
_reflns_number_gt                1397
_reflns_threshold_expression     >2sigma(I)

#------------------ COMPUTER PROGRAMS USED ----------------------------------#

_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_structure_solution    'Direct methods (Sir92,Altomare et al.,1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'DIAMOND 3.2d (Crystal Impact GbR 2005)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#------------------ REFINEMENT INFORMATION ----------------------------------#

_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^)+(0.0470P)^2^+0.3269P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2630
_refine_ls_number_parameters     188
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0554
_refine_ls_wR_factor_ref         0.1339
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.275

#------------------ ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS --------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
_atom_site_disorder_assembly
C1 C 0.9061(4) 0.0364(3) 0.50134(10) 0.0489(6) Uani 1 d . . .
C2 C 0.8082(4) 0.0890(3) 0.55441(10) 0.0463(6) Uani 1 d . . .
C3 C 0.6159(4) 0.1525(4) 0.56420(11) 0.0538(7) Uani 1 d . . .
C4 C 0.6049(4) 0.1773(4) 0.62527(11) 0.0521(6) Uani 1 d . . .
C5 C 0.7927(4) 0.1305(3) 0.65054(10) 0.0440(6) Uani 1 d . . .
C6 C 0.8683(4) 0.1385(3) 0.71152(10) 0.0436(6) Uani 1 d . . .
C7 C 1.1030(4) 0.1073(3) 0.79070(9) 0.0432(6) Uani 1 d . . .
C8 C 0.9784(4) 0.0486(3) 0.83539(10) 0.0462(6) Uani 1 d . . .
C9 C 1.0438(4) 0.0531(3) 0.89433(11) 0.0543(7) Uani 1 d . . .
C10 C 1.2366(5) 0.1183(4) 0.91049(11) 0.0580(7) Uani 1 d . . .
C11 C 1.3633(4) 0.1795(3) 0.86840(12) 0.0551(7) Uani 1 d . . .
C12 C 1.2974(4) 0.1734(3) 0.80933(10) 0.0496(6) Uani 1 d . . .
N1 N 1.0514(3) 0.0925(3) 0.72955(8) 0.0463(5) Uani 1 d . . .
O1 O 0.9222(2) 0.0736(2) 0.60768(6) 0.0449(4) Uani 1 d . . .
F1 F 0.7908(2) -0.0244(2) 0.82147(6) 0.0607(4) Uani 1 d . . .
F2 F 0.9191(3) -0.0106(2) 0.93520(6) 0.0815(5) Uani 1 d . . .
F3 F 1.3044(3) 0.1204(2) 0.96775(6) 0.0849(6) Uani 1 d . . .
F4 F 1.5536(2) 0.2464(2) 0.88390(7) 0.0794(5) Uani 1 d . . .
F5 F 1.4251(2) 0.2367(2) 0.76890(7) 0.0709(5) Uani 1 d . . .
H1 H 0.818(4) 0.055(3) 0.4666(11) 0.057(7) Uiso 1 d . . .
H3 H 0.511(4) 0.171(3) 0.5347(12) 0.065(8) Uiso 1 d . . .
H4 H 0.493(4) 0.222(3) 0.6448(11) 0.062(8) Uiso 1 d . . .
H6 H 0.768(4) 0.191(3) 0.7368(10) 0.054(7) Uiso 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
C1 0.0578(14) 0.0594(16) 0.0287(12) 0.0019(11) -0.0068(12) -0.0126(13)
C2 0.0531(15) 0.0530(14) 0.0318(12) 0.0030(11) -0.0092(10) -0.0085(12)
C3 0.0532(16) 0.0645(17) 0.0419(15) 0.0029(12) -0.0122(12) -0.0011(13)
C4 0.0489(15) 0.0612(17) 0.0455(15) -0.0023(12) -0.0037(12) 0.0029(13)
C5 0.0478(14) 0.0494(14) 0.0349(12) 0.0005(10) 0.0022(10) -0.0007(11)
C6 0.0473(14) 0.0516(14) 0.0321(12) -0.0002(10) 0.0039(11) 0.0000(12)
C7 0.0476(14) 0.0497(14) 0.0319(12) -0.0042(10) -0.0022(10) 0.0108(11)
C8 0.0538(15) 0.0495(14) 0.0353(13) -0.0034(10) 0.0014(11) 0.0043(12)
C9 0.0704(18) 0.0597(16) 0.0330(13) -0.0009(11) 0.0048(12) 0.0099(14)
C10 0.081(2) 0.0600(17) 0.0322(13) -0.0078(11) -0.0097(13) 0.0191(15)
C11 0.0520(16) 0.0577(16) 0.0537(16) -0.0130(13) -0.0148(13) 0.0104(13)
C12 0.0491(15) 0.0586(15) 0.0409(14) -0.0009(11) 0.0011(11) 0.0117(12)
N1 0.0469(12) 0.0605(13) 0.0313(10) -0.0021(9) 0.0007(8) 0.0040(10)
O1 0.0459(9) 0.0598(10) 0.0284(8) 0.0007(7) -0.0032(7) -0.0022(7)
F1 0.0613(9) 0.0753(10) 0.0457(8) 0.0021(7) 0.0035(7) -0.0096(8)
F2 0.1033(13) 0.1043(13) 0.0379(8) 0.0113(8) 0.0136(8) 0.0012(10)
F3 0.1156(14) 0.0995(12) 0.0367(8) -0.0124(8) -0.0230(8) 0.0141(10)
F4 0.0639(10) 0.0919(12) 0.0793(12) -0.0191(9) -0.0245(9) 0.0072(9)
F5 0.0473(9) 0.1050(12) 0.0606(10) 0.0062(9) 0.0043(7) -0.0009(8)

#------------------ 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
C1 C1 1.323(5) 3_756 ?
C1 C2 1.435(3) . ?
C1 H1 0.95(3) . ?
C2 C3 1.350(4) . ?
C2 O1 1.379(3) . ?
C3 C4 1.396(4) . ?
C3 H3 0.93(3) . ?
C4 C5 1.352(3) . ?
C4 H4 0.92(3) . ?
C5 O1 1.374(3) . ?
C5 C6 1.437(3) . ?
C6 N1 1.270(3) . ?
C6 H6 0.96(2) . ?
C7 C12 1.384(3) . ?
C7 C8 1.389(3) . ?
C7 N1 1.407(3) . ?
C8 F1 1.340(3) . ?
C8 C9 1.375(3) . ?
C9 F2 1.338(3) . ?
C9 C10 1.359(4) . ?
C10 F3 1.342(3) . ?
C10 C11 1.360(4) . ?
C11 F4 1.346(3) . ?
C11 C12 1.379(3) . ?
C12 F5 1.342(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
C1 C1 C2 126.0(3) 3_756 . ?
C1 C1 H1 121.6(15) 3_756 . ?
C2 C1 H1 112.4(15) . . ?
C3 C2 O1 109.5(2) . . ?
C3 C2 C1 132.4(2) . . ?
O1 C2 C1 118.0(2) . . ?
C2 C3 C4 107.5(2) . . ?
C2 C3 H3 124.4(16) . . ?
C4 C3 H3 128.0(16) . . ?
C5 C4 C3 107.0(2) . . ?
C5 C4 H4 126.0(16) . . ?
C3 C4 H4 126.9(16) . . ?
C4 C5 O1 109.9(2) . . ?
C4 C5 C6 130.0(2) . . ?
O1 C5 C6 120.0(2) . . ?
N1 C6 C5 123.8(2) . . ?
N1 C6 H6 123.6(14) . . ?
C5 C6 H6 112.4(14) . . ?
C12 C7 C8 115.7(2) . . ?
C12 C7 N1 119.1(2) . . ?
C8 C7 N1 125.1(2) . . ?
F1 C8 C9 117.5(2) . . ?
F1 C8 C7 119.9(2) . . ?
C9 C8 C7 122.5(2) . . ?
F2 C9 C10 120.5(2) . . ?
F2 C9 C8 119.7(2) . . ?
C10 C9 C8 119.7(2) . . ?
F3 C10 C9 120.5(3) . . ?
F3 C10 C11 119.6(3) . . ?
C9 C10 C11 119.9(2) . . ?
F4 C11 C10 120.5(2) . . ?
F4 C11 C12 119.4(2) . . ?
C10 C11 C12 120.0(2) . . ?
F5 C12 C11 118.7(2) . . ?
F5 C12 C7 119.2(2) . . ?
C11 C12 C7 122.1(2) . . ?
C6 N1 C7 117.42(18) . . ?
C5 O1 C2 106.01(17) . . ?

# Attachment '- compound 2 cif.cif'

data_compound2
_database_code_depnum_ccdc_archive 'CCDC 818760'
#TrackingRef '- compound 2 cif.cif'

_audit_creation_date             2008-09-30T11:02:46-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#------------------ CHEMICAL INFORMATION ------------------------------------#

_chemical_formula_moiety         'C18 H4 F10 N2 O1'
_chemical_formula_sum            'C18 H4 F10 N2 O'
_chemical_formula_weight         454.23
_chemical_absolute_configuration ad

#------------------ UNIT CELL INFORMATION -----------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P 1'
_symmetry_space_group_name_Hall  'P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'

_cell_length_a                   4.7787(2)
_cell_length_b                   6.5029(4)
_cell_length_c                   13.9073(5)
_cell_angle_alpha                78.371(3)
_cell_angle_beta                 83.747(3)
_cell_angle_gamma                87.099(4)
_cell_volume                     420.60(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3668
_cell_measurement_theta_min      3.01
_cell_measurement_theta_max      27.96

#------------------ CRYSTAL INFORMATION -------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_exptl_crystal_density_diffrn    1.793
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             224
_exptl_absorpt_coefficient_mu    0.189
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.9491
_exptl_absorpt_correction_T_max  0.9857
_exptl_absorpt_process_details   
;
PLATON-ABSGAUSS : Spek, A.L. (2003), J.Appl.Cryst. 36, 7-13
;

#------------------ DATA COLLECTION INFORMATION -----------------------------#

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            13816
_diffrn_reflns_av_R_equivalents  0.0838
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.01
_diffrn_reflns_theta_max         27.96
_diffrn_reflns_theta_full        27.96
_diffrn_measured_fraction_theta_max 1
_diffrn_measured_fraction_theta_full 1
_reflns_number_total             3764
_reflns_number_gt                2735
_reflns_threshold_expression     >2sigma(I)

#------------------ COMPUTER PROGRAMS USED ----------------------------------#

_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_structure_solution    'Direct methods (Sir92,Altomare et al.,1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'DIAMOND 3.1f (Crystal Impact GbR 2005)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#------------------ REFINEMENT INFORMATION ----------------------------------#

_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^)+(0.1007P)^2^+0.0434P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_coef       0.067(15)
_refine_ls_number_reflns         3764
_refine_ls_number_parameters     297
_refine_ls_number_restraints     3
_refine_ls_R_factor_gt           0.0568
_refine_ls_wR_factor_ref         0.1655
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(2)
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.323

#------------------ ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS --------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
_atom_site_disorder_assembly
C1 C 0.7243(7) 0.9962(5) 0.9358(2) 0.0468(7) Uani 1 d . . .
C2 C 0.6630(8) 1.1990(7) 0.9381(3) 0.0603(9) Uani 1 d . . .
C3 C 0.4323(9) 1.2000(7) 1.0100(3) 0.0613(9) Uani 1 d . . .
C4 C 0.3702(7) 0.9972(6) 1.0472(2) 0.0483(7) Uani 1 d . . .
C5 C 0.1460(7) 0.9100(6) 1.1209(2) 0.0472(7) Uani 1 d . . .
C6 C -0.1172(7) 0.6461(5) 1.2180(2) 0.0470(7) Uani 1 d . . .
C7 C -0.2063(8) 0.7317(7) 1.3008(3) 0.0584(9) Uani 1 d . . .
C8 C -0.4219(8) 0.6452(8) 1.3691(3) 0.0698(11) Uani 1 d . . .
C9 C -0.5512(8) 0.4707(8) 1.3561(3) 0.0704(12) Uani 1 d . . .
C10 C -0.4681(9) 0.3824(7) 1.2767(3) 0.0659(10) Uani 1 d . . .
C11 C -0.2517(8) 0.4691(6) 1.2092(3) 0.0553(8) Uani 1 d . . .
C12 C 0.9422(7) 0.8976(7) 0.8772(2) 0.0519(8) Uani 1 d . . .
C13 C 1.3088(7) 0.9484(6) 0.7474(2) 0.0510(7) Uani 1 d . . .
C14 C 1.4198(9) 1.0985(8) 0.6687(3) 0.0634(9) Uani 1 d . . .
C15 C 1.6443(9) 1.0543(9) 0.6043(3) 0.0770(13) Uani 1 d . . .
C16 C 1.7670(8) 0.8568(10) 0.6162(3) 0.0747(13) Uani 1 d . . .
C17 C 1.6650(9) 0.7038(8) 0.6923(3) 0.0705(11) Uani 1 d . . .
C18 C 1.4339(8) 0.7481(7) 0.7563(3) 0.0630(10) Uani 1 d . . .
N1 N 0.1099(5) 0.7153(4) 1.1466(2) 0.0481(6) Uani 1 d . . .
N2 N 1.0916(6) 1.0170(5) 0.8101(2) 0.0557(7) Uani 1 d . . .
O1 O 0.5497(5) 0.8689(4) 1.00297(17) 0.0494(5) Uani 1 d . . .
F1 F -0.0773(6) 0.8962(5) 1.31783(18) 0.0832(8) Uani 1 d . . .
F2 F -0.5012(7) 0.7314(7) 1.44754(19) 0.1098(12) Uani 1 d . . .
F3 F -0.7624(6) 0.3902(6) 1.4225(2) 0.1064(12) Uani 1 d . . .
F4 F -0.5971(7) 0.2149(5) 1.2632(3) 0.1023(11) Uani 1 d . . .
F5 F -0.1772(6) 0.3816(4) 1.1305(2) 0.0816(8) Uani 1 d . . .
F6 F 1.3434(7) 0.5956(5) 0.8314(2) 0.1020(11) Uani 1 d . . .
F7 F 1.7824(8) 0.5122(6) 0.7078(3) 0.1166(13) Uani 1 d . . .
F8 F 1.9874(6) 0.8148(7) 0.5557(2) 0.1054(12) Uani 1 d . . .
F9 F 1.7436(8) 1.2032(7) 0.5295(3) 0.1269(16) Uani 1 d . . .
F10 F 1.3076(7) 1.2921(5) 0.6538(3) 0.1006(11) Uani 1 d . . .
H2 H 0.763(10) 1.325(7) 0.901(3) 0.068(12) Uiso 1 d . . .
H3 H 0.377(10) 1.325(8) 1.028(4) 0.062(12) Uiso 1 d . . .
H5 H 0.055(8) 1.025(6) 1.143(3) 0.047(9) Uiso 1 d . . .
H12 H 0.960(9) 0.744(7) 0.890(3) 0.052(10) Uiso 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
C1 0.0395(15) 0.0644(19) 0.0335(13) -0.0055(13) 0.0010(11) -0.0009(13)
C2 0.055(2) 0.066(2) 0.0515(18) -0.0020(16) 0.0142(15) -0.0030(17)
C3 0.058(2) 0.060(2) 0.063(2) -0.0140(17) 0.0110(16) 0.0004(17)
C4 0.0421(16) 0.062(2) 0.0382(14) -0.0072(13) 0.0006(12) 0.0021(14)
C5 0.0398(15) 0.058(2) 0.0406(14) -0.0082(13) 0.0050(12) 0.0007(13)
C6 0.0384(15) 0.0557(17) 0.0425(15) -0.0055(13) 0.0051(12) 0.0030(13)
C7 0.0489(19) 0.081(2) 0.0457(16) -0.0170(16) 0.0070(15) -0.0091(17)
C8 0.052(2) 0.116(3) 0.0369(15) -0.0122(18) 0.0104(14) -0.006(2)
C9 0.0445(19) 0.103(3) 0.0518(19) 0.009(2) 0.0095(16) -0.012(2)
C10 0.053(2) 0.065(2) 0.072(2) 0.0063(19) -0.0075(18) -0.0081(17)
C11 0.0527(18) 0.0578(19) 0.0538(17) -0.0099(15) -0.0018(14) 0.0030(15)
C12 0.0406(15) 0.067(2) 0.0454(16) -0.0109(15) 0.0055(13) -0.0007(14)
C13 0.0367(15) 0.076(2) 0.0382(14) -0.0118(14) 0.0042(12) 0.0004(14)
C14 0.0484(19) 0.087(3) 0.0483(18) -0.0056(17) 0.0062(15) 0.0035(17)
C15 0.049(2) 0.125(4) 0.048(2) -0.003(2) 0.0104(16) -0.005(2)
C16 0.0427(19) 0.136(4) 0.0454(17) -0.027(2) 0.0052(14) 0.007(2)
C17 0.051(2) 0.098(3) 0.063(2) -0.027(2) 0.0049(17) 0.017(2)
C18 0.054(2) 0.081(3) 0.0506(18) -0.0129(17) 0.0057(16) 0.0066(18)
N1 0.0361(13) 0.0596(17) 0.0476(14) -0.0143(12) 0.0047(11) 0.0022(12)
N2 0.0400(14) 0.078(2) 0.0457(15) -0.0112(14) 0.0073(12) 0.0039(13)
O1 0.0401(11) 0.0595(13) 0.0461(11) -0.0115(10) 0.0086(9) -0.0017(9)
F1 0.0846(18) 0.113(2) 0.0587(13) -0.0390(14) 0.0166(13) -0.0304(16)
F2 0.083(2) 0.194(4) 0.0549(14) -0.0467(19) 0.0302(14) -0.021(2)
F3 0.0596(15) 0.167(3) 0.0707(17) 0.0212(18) 0.0183(12) -0.0319(17)
F4 0.094(2) 0.0809(18) 0.127(3) -0.0100(17) 0.006(2) -0.0375(16)
F5 0.0822(18) 0.0740(15) 0.0941(18) -0.0404(14) 0.0153(15) -0.0099(13)
F6 0.097(2) 0.0886(19) 0.095(2) 0.0098(15) 0.0368(17) 0.0296(16)
F7 0.098(2) 0.119(3) 0.122(3) -0.030(2) 0.025(2) 0.044(2)
F8 0.0550(15) 0.192(4) 0.0671(15) -0.0408(19) 0.0215(12) 0.0161(18)
F9 0.086(2) 0.173(4) 0.085(2) 0.031(2) 0.0463(18) 0.004(2)
F10 0.090(2) 0.0897(18) 0.096(2) 0.0154(15) 0.0359(17) 0.0108(15)

#------------------ 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
C1 C2 1.342(6) . ?
C1 O1 1.357(4) . ?
C1 C12 1.455(5) . ?
C2 C3 1.406(5) . ?
C2 H2 0.99(5) . ?
C3 C4 1.351(6) . ?
C3 H3 0.91(5) . ?
C4 O1 1.353(4) . ?
C4 C5 1.452(4) . ?
C5 N1 1.260(5) . ?
C5 H5 0.94(4) . ?
C6 C11 1.379(5) . ?
C6 C7 1.394(5) . ?
C6 N1 1.415(4) . ?
C7 F1 1.335(5) . ?
C7 C8 1.382(5) . ?
C8 F2 1.335(5) . ?
C8 C9 1.371(7) . ?
C9 F3 1.342(4) . ?
C9 C10 1.358(7) . ?
C10 F4 1.333(6) . ?
C10 C11 1.380(6) . ?
C11 F5 1.339(5) . ?
C12 N2 1.265(4) . ?
C12 H12 0.98(4) . ?
C13 C14 1.387(5) . ?
C13 C18 1.394(6) . ?
C13 N2 1.397(4) . ?
C14 F10 1.329(6) . ?
C14 C15 1.378(6) . ?
C15 F9 1.334(5) . ?
C15 C16 1.371(8) . ?
C16 F8 1.327(5) . ?
C16 C17 1.364(7) . ?
C17 F7 1.327(6) . ?
C17 C18 1.397(5) . ?
C18 F6 1.337(5) . ?

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
C2 C1 O1 110.9(3) . . ?
C2 C1 C12 131.3(3) . . ?
O1 C1 C12 117.8(3) . . ?
C1 C2 C3 106.0(3) . . ?
C1 C2 H2 129(3) . . ?
C3 C2 H2 125(3) . . ?
C4 C3 C2 106.8(4) . . ?
C4 C3 H3 134(3) . . ?
C2 C3 H3 118(3) . . ?
C3 C4 O1 110.1(3) . . ?
C3 C4 C5 129.6(3) . . ?
O1 C4 C5 120.3(3) . . ?
N1 C5 C4 122.4(3) . . ?
N1 C5 H5 132(2) . . ?
C4 C5 H5 106(2) . . ?
C11 C6 C7 116.5(3) . . ?
C11 C6 N1 117.4(3) . . ?
C7 C6 N1 126.0(3) . . ?
F1 C7 C8 118.1(4) . . ?
F1 C7 C6 120.4(3) . . ?
C8 C7 C6 121.4(4) . . ?
F2 C8 C9 120.6(4) . . ?
F2 C8 C7 119.7(4) . . ?
C9 C8 C7 119.7(4) . . ?
F3 C9 C10 120.7(4) . . ?
F3 C9 C8 119.0(4) . . ?
C10 C9 C8 120.3(3) . . ?
F4 C10 C9 120.3(4) . . ?
F4 C10 C11 120.1(4) . . ?
C9 C10 C11 119.5(4) . . ?
F5 C11 C6 119.1(3) . . ?
F5 C11 C10 118.4(4) . . ?
C6 C11 C10 122.4(3) . . ?
N2 C12 C1 117.4(3) . . ?
N2 C12 H12 124(2) . . ?
C1 C12 H12 119(2) . . ?
C14 C13 C18 116.0(3) . . ?
C14 C13 N2 116.4(4) . . ?
C18 C13 N2 127.5(3) . . ?
F10 C14 C15 118.1(4) . . ?
F10 C14 C13 119.6(3) . . ?
C15 C14 C13 122.3(4) . . ?
F9 C15 C16 119.3(4) . . ?
F9 C15 C14 120.3(5) . . ?
C16 C15 C14 120.4(4) . . ?
F8 C16 C17 119.9(5) . . ?
F8 C16 C15 120.6(5) . . ?
C17 C16 C15 119.5(3) . . ?
F7 C17 C16 121.3(4) . . ?
F7 C17 C18 118.7(4) . . ?
C16 C17 C18 120.0(4) . . ?
F6 C18 C13 119.7(3) . . ?
F6 C18 C17 118.3(4) . . ?
C13 C18 C17 121.8(4) . . ?
C5 N1 C6 118.0(3) . . ?
C12 N2 C13 124.8(3) . . ?
C4 O1 C1 106.2(3) . . ?