# 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 2013


#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication 
#  deposited with the CCDC, and may include chemical, crystal,   
#  experimental, refinement, atomic coordinates, 
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted. 
# 
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#  fide research purposes only. It may contain copyright material 
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#  except for the purpose of generating routine backup copies 
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
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data_ev234
_database_code_depnum_ccdc_archive 'CCDC 872138'
#TrackingRef '10209_web_deposit_cif_file_0_Cahard_1332164605.EV 234.cif'


_audit_creation_date             2011-12-12T11:25:46-00:00
_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

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

_chemical_name_systematic        
;
?
;
_chemical_formula_moiety         'C9 H17 Cl1 F1 N1 O1'
_chemical_formula_sum            'C9 H17 Cl F N O'
_chemical_formula_weight         209.69
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration rmad

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   6.8983(6)
_cell_length_b                   12.0634(10)
_cell_length_c                   12.5086(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1040.93(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       rodlike
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             448
_exptl_special_details           
;
?
;

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.344
_exptl_absorpt_correction_type   none

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

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0174
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_number            8336
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.35
_diffrn_reflns_theta_max         26.43
_diffrn_reflns_theta_full        26.43
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_reflns_number_total             2137
_reflns_number_gt                2098
_reflns_threshold_expression     >2sigma(I)

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

_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

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

_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^)+(0.0416P)^2^+0.0987P] 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         2137
_refine_ls_number_parameters     124
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0272
_refine_ls_R_factor_gt           0.0266
_refine_ls_wR_factor_ref         0.07
_refine_ls_wR_factor_gt          0.0689
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_restrained_S_all      1.118
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(5)
_refine_diff_density_max         0.19
_refine_diff_density_min         -0.124
_refine_diff_density_rms         0.037

#----------------------------------------------------------------------------#
# 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'
Cl Cl 0.1484 0.1585 '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'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.17237(5) 0.63164(3) 0.05427(3) 0.03838(11) Uani 1 1 d . . .
F1 F -0.52321(13) 0.40189(7) -0.11072(8) 0.0438(2) Uani 1 1 d . . .
N1 N -0.45020(18) 0.61949(9) -0.09245(9) 0.0308(3) Uani 1 1 d . . .
H1A H -0.4744 0.6067 -0.1612 0.046 Uiso 1 1 calc R . .
H1B H -0.4054 0.6882 -0.0846 0.046 Uiso 1 1 calc R . .
H1C H -0.559 0.6117 -0.0549 0.046 Uiso 1 1 calc R . .
O1 O -0.4045(2) 0.07830(9) -0.19871(9) 0.0419(3) Uani 1 1 d . . .
C1 C -0.3396(2) 0.16923(11) -0.13425(11) 0.0317(3) Uani 1 1 d . . .
H1D H -0.2447 0.1439 -0.0825 0.038 Uiso 1 1 calc R . .
H1E H -0.448 0.2016 -0.0959 0.038 Uiso 1 1 calc R . .
C2 C -0.2493(2) 0.25480(11) -0.20888(11) 0.0271(3) Uani 1 1 d . . .
H2 H -0.3373 0.2689 -0.2689 0.033 Uiso 1 1 calc R . .
C3 C -0.0516(2) 0.21602(12) -0.25211(12) 0.0345(3) Uani 1 1 d . . .
H3A H -0.0423 0.1358 -0.2505 0.041 Uiso 1 1 calc R . .
H3B H -0.0326 0.2412 -0.325 0.041 Uiso 1 1 calc R . .
C4 C 0.0972(2) 0.26816(13) -0.17773(14) 0.0386(4) Uani 1 1 d . . .
H4A H 0.2233 0.2726 -0.2117 0.046 Uiso 1 1 calc R . .
H4B H 0.1089 0.2262 -0.1119 0.046 Uiso 1 1 calc R . .
C5 C 0.0144(2) 0.38410(12) -0.15647(12) 0.0309(3) Uani 1 1 d . . .
H5A H 0.0608 0.4135 -0.089 0.037 Uiso 1 1 calc R . .
H5B H 0.0483 0.4351 -0.2134 0.037 Uiso 1 1 calc R . .
C6 C -0.2025(2) 0.36371(11) -0.15317(10) 0.0256(3) Uani 1 1 d . . .
C7 C -0.3302(2) 0.43003(11) -0.10929(11) 0.0280(3) Uani 1 1 d . . .
C8 C -0.30111(19) 0.53813(11) -0.05283(11) 0.0279(3) Uani 1 1 d . . .
H8 H -0.1718 0.5665 -0.0703 0.033 Uiso 1 1 calc R . .
C9 C -0.3188(3) 0.52856(13) 0.06794(12) 0.0377(3) Uani 1 1 d . . .
H9A H -0.4462 0.5027 0.0861 0.056 Uiso 1 1 calc R . .
H9B H -0.2974 0.5999 0.0999 0.056 Uiso 1 1 calc R . .
H9C H -0.2239 0.4771 0.0941 0.056 Uiso 1 1 calc R . .
HO1 H -0.366(3) 0.027(2) -0.170(2) 0.072(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
Cl1 0.03665(19) 0.02723(17) 0.0513(2) 0.00109(16) 0.00380(17) 0.00101(15)
F1 0.0258(4) 0.0325(5) 0.0730(7) -0.0135(5) -0.0005(4) -0.0046(4)
N1 0.0370(7) 0.0207(5) 0.0349(6) -0.0003(5) -0.0012(5) 0.0028(5)
O1 0.0646(8) 0.0221(6) 0.0390(6) 0.0032(4) -0.0087(5) -0.0118(5)
C1 0.0402(8) 0.0258(6) 0.0291(6) -0.0004(5) 0.0004(6) -0.0043(6)
C2 0.0342(7) 0.0209(6) 0.0263(6) -0.0008(5) -0.0027(5) -0.0019(5)
C3 0.0421(9) 0.0246(7) 0.0369(7) -0.0040(6) 0.0065(7) 0.0014(6)
C4 0.0330(8) 0.0350(8) 0.0476(9) -0.0051(7) 0.0020(7) 0.0066(6)
C5 0.0298(7) 0.0266(7) 0.0364(7) -0.0040(6) 0.0007(6) -0.0018(6)
C6 0.0307(7) 0.0197(6) 0.0263(6) 0.0012(5) -0.0023(5) -0.0015(5)
C7 0.0267(6) 0.0227(6) 0.0347(7) -0.0009(5) -0.0029(6) -0.0026(6)
C8 0.0246(6) 0.0229(6) 0.0361(7) -0.0023(5) -0.0016(6) 0.0000(5)
C9 0.0405(8) 0.0384(8) 0.0341(8) -0.0035(6) -0.0063(7) 0.0033(7)


#----------------------------------------------------------------------------#
# 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 C7 1.3741(17) . ?
N1 C8 1.5055(17) . ?
N1 H1A 0.89 . ?
N1 H1B 0.89 . ?
N1 H1C 0.89 . ?
O1 C1 1.4330(17) . ?
O1 HO1 0.77(3) . ?
C1 C2 1.5250(19) . ?
C1 H1D 0.97 . ?
C1 H1E 0.97 . ?
C2 C6 1.5220(18) . ?
C2 C3 1.540(2) . ?
C2 H2 0.98 . ?
C3 C4 1.522(2) . ?
C3 H3A 0.97 . ?
C3 H3B 0.97 . ?
C4 C5 1.534(2) . ?
C4 H4A 0.97 . ?
C4 H4B 0.97 . ?
C5 C6 1.516(2) . ?
C5 H5A 0.97 . ?
C5 H5B 0.97 . ?
C6 C7 1.311(2) . ?
C7 C8 1.4964(18) . ?
C8 C9 1.520(2) . ?
C8 H8 0.98 . ?
C9 H9A 0.96 . ?
C9 H9B 0.96 . ?
C9 H9C 0.96 . ?

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
C8 N1 H1A 109.5 . . ?
C8 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C8 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C1 O1 HO1 104(2) . . ?
O1 C1 C2 107.53(11) . . ?
O1 C1 H1D 110.2 . . ?
C2 C1 H1D 110.2 . . ?
O1 C1 H1E 110.2 . . ?
C2 C1 H1E 110.2 . . ?
H1D C1 H1E 108.5 . . ?
C6 C2 C1 113.00(11) . . ?
C6 C2 C3 103.60(11) . . ?
C1 C2 C3 111.80(12) . . ?
C6 C2 H2 109.4 . . ?
C1 C2 H2 109.4 . . ?
C3 C2 H2 109.4 . . ?
C4 C3 C2 104.90(12) . . ?
C4 C3 H3A 110.8 . . ?
C2 C3 H3A 110.8 . . ?
C4 C3 H3B 110.8 . . ?
C2 C3 H3B 110.8 . . ?
H3A C3 H3B 108.8 . . ?
C3 C4 C5 103.39(12) . . ?
C3 C4 H4A 111.1 . . ?
C5 C4 H4A 111.1 . . ?
C3 C4 H4B 111.1 . . ?
C5 C4 H4B 111.1 . . ?
H4A C4 H4B 109 . . ?
C6 C5 C4 102.96(12) . . ?
C6 C5 H5A 111.2 . . ?
C4 C5 H5A 111.2 . . ?
C6 C5 H5B 111.2 . . ?
C4 C5 H5B 111.2 . . ?
H5A C5 H5B 109.1 . . ?
C7 C6 C5 125.14(13) . . ?
C7 C6 C2 125.16(13) . . ?
C5 C6 C2 109.69(12) . . ?
C6 C7 F1 119.68(12) . . ?
C6 C7 C8 129.74(13) . . ?
F1 C7 C8 110.58(12) . . ?
C7 C8 N1 108.73(11) . . ?
C7 C8 C9 113.09(12) . . ?
N1 C8 C9 108.78(12) . . ?
C7 C8 H8 108.7 . . ?
N1 C8 H8 108.7 . . ?
C9 C8 H8 108.7 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

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 C1 C2 C6 171.05(12) . . . . ?
O1 C1 C2 C3 -72.53(16) . . . . ?
C6 C2 C3 C4 26.51(15) . . . . ?
C1 C2 C3 C4 -95.48(14) . . . . ?
C2 C3 C4 C5 -39.32(15) . . . . ?
C3 C4 C5 C6 35.92(15) . . . . ?
C4 C5 C6 C7 160.33(13) . . . . ?
C4 C5 C6 C2 -19.87(15) . . . . ?
C1 C2 C6 C7 -62.87(18) . . . . ?
C3 C2 C6 C7 175.95(13) . . . . ?
C1 C2 C6 C5 117.33(14) . . . . ?
C3 C2 C6 C5 -3.85(15) . . . . ?
C5 C6 C7 F1 -179.49(13) . . . . ?
C2 C6 C7 F1 0.7(2) . . . . ?
C5 C6 C7 C8 -0.3(2) . . . . ?
C2 C6 C7 C8 179.97(13) . . . . ?
C6 C7 C8 N1 134.91(15) . . . . ?
F1 C7 C8 N1 -45.82(15) . . . . ?
C6 C7 C8 C9 -104.17(17) . . . . ?
F1 C7 C8 C9 75.11(15) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O1 0.89 1.97 2.8419(17) 165.7 4_454
N1 H1B Cl1 0.89 2.27 3.1554(12) 172.7 3_465
N1 H1C Cl1 0.89 2.31 3.1888(13) 167.2 1_455
O1 HO1 Cl1 0.77(3) 2.41(3) 3.1558(13) 165(2) 3_455