# Electronic Supplementary Material (ESI) for New Journal of Chemistry
# This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2011


data_General
_journal_name_full               'New J.Chem.'
_journal_coden_cambridge         0440
#TrackingRef 'CIF.cif'

_audit_creation_date             2009-11-08
_audit_creation_method           'by CrystalStructure 3.8'
_audit_update_record             ?

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

# PROCESSING SUMMARY (IUCr Office Use Only)

_journal_date_recd_electronic    ?
_journal_date_from_coeditor      ?
_journal_date_accepted           ?
_journal_coeditor_code           ?

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

# SUBMISSION DETAILS

_publ_contact_author_name        'Norio Shibata'
_publ_contact_author_email       nozshiba@nitech.ac.jp
_publ_contact_author_fax         'ENTER FAX NUMBER'
_publ_contact_author_phone       'ENTER PHONE NUMBER'
_publ_contact_letter             
;
ENTER TEXT OF LETTER
;
_publ_requested_category         'CHOOSE FI FM FO CI CM CO or AD'
_publ_requested_coeditor_name    ?

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

# TITLE AND AUTHOR LIST

_publ_section_title              
;
ENTER SECTION TITLE
;
_publ_section_title_footnote     
;
ENTER FOOTNOTE TO TITLE OF PAPER
;
loop_
_publ_author_footnote
_publ_author_address
;
FIRST AUTHORS FOOTNOTES
;
;
FIRST AUTHORS ADDRESS
;
_publ_section_synopsis           
;
ENTER SYNOPSIS
;

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

# TEXT

_publ_section_abstract           
;
ENTER ABSTRACT
;
_publ_section_comment            
;
ENTER TEXT
;
_publ_section_references         
;
ENTER OTHER REFERENCES

Johnson, C.K. (1976). ORTEP-II. A FORTRAN Thermal-Ellipsoid Plot
Program. Report ORNL-5138. Oak Ridge National Laboratory,
Tennessee, USA.

Rigaku (1998). PROCESS-AUTO. Automatic Data Acquisition and Processing
Package for Imaging Plate Diffractometer. Rigaku Corporation, Tokyo
196-8666, Japan

Rigaku & RAC (2007). CrystalStructure (Version 3.80). Single Crystal
Structure Analysis Software. Rigaku, Tokyo 196-8666, Japan. Rigaku
Americas, TX, USA 77381-5209.

Sheldrick, G.M. (1997). SHELXS97. Program for the Solution of Crystal
Structures. University of Gottingen, Germany.

Sheldrick, G.M. (1997). SHELXL97. University of Gottingen, Germany.

;
_publ_section_figure_captions    
;
ENTER FIGURE CAPTIONS
;
_publ_section_exptl_prep         
;
ENTER COMPOUND PREPARATION DETAILS
;
_publ_section_exptl_refinement   
;
ENTER SPECIAL DETAILS OF THE REFINEMENT
;
loop_
_publ_author_name
'Yiyong Huang'
'Satoru Suzuki'
'Guokai Liu'
'Etsuko Tokunaga'
'Motoo Shiro'
'Norio Shibata'

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

data__FC-164
_database_code_depnum_ccdc_archive 'CCDC 758056'
#TrackingRef 'CIF.cif'

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

# CHEMICAL DATA

_chemical_formula_sum            'C18 H17 F3 N2 O3 '
_chemical_formula_moiety         'C18 H17 F3 N2 O3 '
_chemical_formula_weight         366.34
_chemical_melting_point          ?
_chemical_absolute_configuration ad

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

# CRYSTAL DATA
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_Int_Tables_number      4
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

#------------------------------------------------------------------------------

_cell_length_a                   10.77497(19)
_cell_length_b                   6.30036(11)
_cell_length_c                   12.5202(7)
_cell_angle_alpha                90.0000
_cell_angle_beta                 92.0681(9)
_cell_angle_gamma                90.0000
_cell_volume                     849.39(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    15209
_cell_measurement_theta_min      4.1
_cell_measurement_theta_max      68.3
_cell_measurement_temperature    93.1

#------------------------------------------------------------------------------

_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             380.00
_exptl_absorpt_coefficient_mu    1.033
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Higashi, T. (1995). Program for Absorption Correction.
Rigaku Corporation, Tokyo, Japan.
;
_exptl_absorpt_correction_T_min  0.794
_exptl_absorpt_correction_T_max  0.950

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

# EXPERIMENTAL DATA

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean 10.00
_diffrn_reflns_number            16058
_diffrn_reflns_av_R_equivalents  0.021
_diffrn_reflns_theta_max         68.23
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        68.23
_diffrn_measured_fraction_theta_full 0.999
_diffrn_ambient_temperature      93.1
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15

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

# REFINEMENT DATA

_refine_special_details          
;
Refinement was performed using all reflections. The weighted
R-factor (wR) and goodness of fit (S) are based on F^2^.
R-factor (gt) are based on F. The threshold expression of
F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt).
;
_reflns_number_total             2971
_reflns_number_gt                2914
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0243
_refine_ls_wR_factor_ref         0.0617
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2971
_refine_ls_number_parameters     236
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[\s^2^(Fo^2^)+(0.0329P)^2^+0.2077P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_shift/su_max          0.0010
_refine_diff_density_max         0.19
_refine_diff_density_min         -0.13
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
'Flack, H. D. (1983), Acta Cryst. A39, 876-881. 1272 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.00(8)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.018 0.009
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
F F 0.073 0.053
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.031 0.018
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.049 0.032
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

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

# ATOMIC COORDINATES AND THERMAL 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 0.31179(7) 0.89469(14) 0.34396(6) 0.02370(19) Uani 1 1 d . . .
F2 F 0.12286(7) 0.78413(15) 0.34175(6) 0.0282(2) Uani 1 1 d . . .
F3 F 0.17487(8) 1.06603(13) 0.43025(6) 0.02585(19) Uani 1 1 d . . .
O1 O 0.18863(10) 0.36331(17) 0.61358(8) 0.0270(2) Uani 1 1 d . . .
O2 O -0.02549(10) 0.61605(18) 0.87937(8) 0.0284(2) Uani 1 1 d . . .
O3 O 0.00293(11) 0.86846(17) 0.75823(9) 0.0314(2) Uani 1 1 d . . .
N1 N 0.35727(10) 0.9999(2) 0.61795(9) 0.0201(2) Uani 1 1 d . . .
H1N H 0.2976 1.0952 0.6158 0.024 Uiso 1 1 calc R . .
N2 N 0.09472(10) 0.53351(18) 0.74497(9) 0.0186(2) Uani 1 1 d . . .
C1 C 0.46860(12) 1.0199(3) 0.67325(11) 0.0226(3) Uani 1 1 d . . .
H1 H 0.4948 1.1388 0.7149 0.027 Uiso 1 1 calc R . .
C2 C 0.53547(12) 0.8387(2) 0.65803(11) 0.0233(3) Uani 1 1 d . . .
H2 H 0.6160 0.8086 0.6875 0.028 Uiso 1 1 calc R . .
C3 C 0.46276(12) 0.7040(2) 0.59024(11) 0.0215(3) Uani 1 1 d . . .
H3 H 0.4855 0.5672 0.5658 0.026 Uiso 1 1 calc R . .
C4 C 0.35349(12) 0.8080(2) 0.56646(10) 0.0185(3) Uani 1 1 d . . .
C5 C 0.24204(12) 0.7326(2) 0.50177(11) 0.0188(3) Uani 1 1 d . . .
H5 H 0.2611 0.5868 0.4754 0.023 Uiso 1 1 calc R . .
C6 C 0.21378(12) 0.8698(2) 0.40507(10) 0.0200(3) Uani 1 1 d . . .
C7 C 0.12579(12) 0.7159(2) 0.56983(11) 0.0211(3) Uani 1 1 d . . .
H7A H 0.1166 0.8467 0.6126 0.025 Uiso 1 1 calc R . .
H7B H 0.0506 0.6993 0.5227 0.025 Uiso 1 1 calc R . .
C8 C 0.14002(12) 0.5259(2) 0.64307(11) 0.0199(3) Uani 1 1 d . . .
C9 C 0.02226(13) 0.6923(2) 0.78991(11) 0.0227(3) Uani 1 1 d . . .
C10 C 0.00292(13) 0.3935(3) 0.89340(11) 0.0257(3) Uani 1 1 d . . .
H10A H -0.0720 0.3057 0.8787 0.031 Uiso 1 1 calc R . .
H10B H 0.0342 0.3652 0.9673 0.031 Uiso 1 1 calc R . .
C11 C 0.10265(13) 0.3439(2) 0.81348(11) 0.0220(3) Uani 1 1 d . . .
H11 H 0.0774 0.2160 0.7706 0.026 Uiso 1 1 calc R . .
C12 C 0.23352(13) 0.3091(2) 0.86385(11) 0.0249(3) Uani 1 1 d . . .
H12A H 0.2330 0.1763 0.9061 0.030 Uiso 1 1 calc R . .
H12B H 0.2921 0.2887 0.8056 0.030 Uiso 1 1 calc R . .
C13 C 0.28191(12) 0.4863(2) 0.93529(11) 0.0211(3) Uani 1 1 d . . .
C14 C 0.26539(12) 0.4787(3) 1.04536(11) 0.0235(3) Uani 1 1 d . . .
H14 H 0.2238 0.3610 1.0753 0.028 Uiso 1 1 calc R . .
C15 C 0.30886(13) 0.6404(3) 1.11123(12) 0.0266(3) Uani 1 1 d . . .
H15 H 0.2961 0.6338 1.1858 0.032 Uiso 1 1 calc R . .
C16 C 0.37092(13) 0.8120(3) 1.06930(13) 0.0292(3) Uani 1 1 d . . .
H16 H 0.4003 0.9233 1.1147 0.035 Uiso 1 1 calc R . .
C17 C 0.38980(13) 0.8198(3) 0.96023(13) 0.0290(3) Uani 1 1 d . . .
H17 H 0.4338 0.9356 0.9311 0.035 Uiso 1 1 calc R . .
C18 C 0.34473(12) 0.6591(3) 0.89363(12) 0.0249(3) Uani 1 1 d . . .
H18 H 0.3568 0.6670 0.8189 0.030 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.0224(4) 0.0300(5) 0.0188(4) 0.0005(3) 0.0029(3) -0.0017(4)
F2 0.0233(4) 0.0376(5) 0.0230(4) 0.0014(4) -0.0073(3) -0.0047(4)
F3 0.0308(4) 0.0225(5) 0.0242(4) 0.0012(3) 0.0013(3) 0.0082(4)
O1 0.0338(5) 0.0205(6) 0.0269(5) -0.0019(4) 0.0055(4) 0.0066(4)
O2 0.0362(6) 0.0254(6) 0.0242(5) -0.0010(4) 0.0105(4) -0.0005(5)
O3 0.0423(6) 0.0179(6) 0.0349(6) -0.0009(5) 0.0133(5) 0.0045(5)
N1 0.0184(5) 0.0209(6) 0.0211(5) -0.0024(5) 0.0002(4) 0.0024(5)
N2 0.0201(5) 0.0153(6) 0.0204(5) 0.0005(5) -0.0006(4) -0.0019(5)
C1 0.0217(6) 0.0268(8) 0.0190(6) -0.0016(6) -0.0011(5) -0.0020(6)
C2 0.0184(6) 0.0303(9) 0.0211(7) 0.0008(6) -0.0019(5) 0.0016(6)
C3 0.0210(6) 0.0240(8) 0.0196(6) -0.0006(6) 0.0009(5) 0.0040(6)
C4 0.0203(6) 0.0208(7) 0.0146(6) 0.0001(5) 0.0021(5) 0.0010(5)
C5 0.0185(6) 0.0186(7) 0.0193(6) -0.0024(5) 0.0009(5) 0.0014(5)
C6 0.0183(6) 0.0240(8) 0.0179(6) -0.0034(6) 0.0011(5) -0.0003(6)
C7 0.0192(6) 0.0222(7) 0.0221(7) 0.0019(6) 0.0022(5) 0.0016(5)
C8 0.0177(6) 0.0200(8) 0.0220(6) -0.0027(6) 0.0003(5) -0.0022(6)
C9 0.0256(7) 0.0199(8) 0.0229(7) -0.0048(6) 0.0035(5) -0.0021(6)
C10 0.0273(7) 0.0254(8) 0.0244(7) 0.0043(6) -0.0016(5) -0.0051(7)
C11 0.0279(7) 0.0169(7) 0.0209(6) 0.0002(5) -0.0024(5) -0.0026(5)
C12 0.0295(7) 0.0219(8) 0.0232(7) 0.0003(6) -0.0014(5) 0.0045(6)
C13 0.0175(6) 0.0235(8) 0.0221(7) 0.0014(6) -0.0013(5) 0.0048(6)
C14 0.0186(6) 0.0281(8) 0.0237(7) 0.0023(6) -0.0004(5) 0.0016(6)
C15 0.0197(7) 0.0367(9) 0.0231(7) -0.0038(6) -0.0014(5) 0.0040(6)
C16 0.0216(7) 0.0281(9) 0.0373(8) -0.0074(7) -0.0084(6) 0.0025(6)
C17 0.0201(7) 0.0260(9) 0.0404(8) 0.0068(7) -0.0037(6) -0.0008(6)
C18 0.0187(7) 0.0313(9) 0.0247(7) 0.0043(6) 0.0001(5) 0.0026(6)

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

_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku & RAC 2007)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_publication_material  'CrystalStructure (Rigaku & RAC 2007)'
_computing_molecular_graphics    'ORTEP (Johnson, 1976)'

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

# MOLECULAR GEOMETRY

_geom_special_details            
;
ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

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 1.3355(16) . ?
F2 C6 1.3504(16) . ?
F3 C6 1.3464(17) . ?
O1 C8 1.2140(18) . ?
O2 C9 1.3385(17) . ?
O2 C10 1.4446(19) . ?
O3 C9 1.1943(18) . ?
N1 C1 1.3690(17) . ?
N1 C4 1.3698(19) . ?
N2 C8 1.3832(17) . ?
N2 C9 1.3996(18) . ?
N2 C11 1.4714(18) . ?
C1 C2 1.367(2) . ?
C2 C3 1.416(2) . ?
C3 C4 1.3707(19) . ?
C4 C5 1.5012(18) . ?
C5 C6 1.5098(19) . ?
C5 C7 1.5437(18) . ?
C7 C8 1.512(2) . ?
C10 C11 1.527(2) . ?
C11 C12 1.5395(19) . ?
C12 C13 1.511(2) . ?
C13 C18 1.393(2) . ?
C13 C14 1.397(2) . ?
C14 C15 1.382(2) . ?
C15 C16 1.384(2) . ?
C16 C17 1.389(2) . ?
C17 C18 1.388(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
C9 O2 C10 111.35(11) . . ?
C1 N1 C4 109.26(11) . . ?
C8 N2 C9 128.03(12) . . ?
C8 N2 C11 119.64(11) . . ?
C9 N2 C11 111.57(11) . . ?
C2 C1 N1 108.03(13) . . ?
C1 C2 C3 107.51(12) . . ?
C4 C3 C2 107.21(13) . . ?
N1 C4 C3 107.99(12) . . ?
N1 C4 C5 122.88(12) . . ?
C3 C4 C5 129.04(14) . . ?
C4 C5 C6 112.68(11) . . ?
C4 C5 C7 111.90(11) . . ?
C6 C5 C7 109.72(11) . . ?
F1 C6 F3 106.60(11) . . ?
F1 C6 F2 106.41(10) . . ?
F3 C6 F2 106.21(11) . . ?
F1 C6 C5 112.70(11) . . ?
F3 C6 C5 113.17(11) . . ?
F2 C6 C5 111.28(12) . . ?
C8 C7 C5 108.80(11) . . ?
O1 C8 N2 118.70(13) . . ?
O1 C8 C7 121.25(12) . . ?
N2 C8 C7 120.03(12) . . ?
O3 C9 O2 122.94(14) . . ?
O3 C9 N2 128.60(14) . . ?
O2 C9 N2 108.46(12) . . ?
O2 C10 C11 105.67(11) . . ?
N2 C11 C10 100.86(11) . . ?
N2 C11 C12 112.80(11) . . ?
C10 C11 C12 114.62(11) . . ?
C13 C12 C11 115.38(12) . . ?
C18 C13 C14 118.50(14) . . ?
C18 C13 C12 121.17(13) . . ?
C14 C13 C12 120.33(14) . . ?
C15 C14 C13 120.72(15) . . ?
C14 C15 C16 120.50(14) . . ?
C15 C16 C17 119.36(14) . . ?
C18 C17 C16 120.29(14) . . ?
C17 C18 C13 120.61(13) . . ?

#===END========================================================================