# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ch
_database_code_depnum_ccdc_archive 'CCDC 1042102'
_audit_update_record             
;
2015-01-05 deposited with the CCDC.
2015-04-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H9 F3 N2 O3'
_chemical_formula_weight         274.20

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   5.736(3)
_cell_length_b                   7.686(5)
_cell_length_c                   15.026(9)
_cell_angle_alpha                102.598(13)
_cell_angle_beta                 92.769(13)
_cell_angle_gamma                110.155(13)
_cell_volume                     601.4(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    873
_cell_measurement_theta_min      2.803
_cell_measurement_theta_max      22.679

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      NONE
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             280
_exptl_absorpt_coefficient_mu    0.141
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9616
_exptl_absorpt_correction_T_max  0.9724
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3440
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_sigmaI/netI    0.0679
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.40
_diffrn_reflns_theta_max         25.03
_reflns_number_total             2109
_reflns_number_gt                1411
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/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         2109
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1215
_refine_ls_R_factor_gt           0.0982
_refine_ls_wR_factor_ref         0.3071
_refine_ls_wR_factor_gt          0.2771
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.4477(7) 1.3989(4) 0.1851(3) 0.1193(13) Uani 1 1 d . . .
F2 F 0.1337(6) 1.2177(5) 0.0856(2) 0.0970(11) Uani 1 1 d . . .
F3 F 0.0758(8) 1.3240(5) 0.2223(3) 0.1189(14) Uani 1 1 d . . .
O1 O 0.0276(5) 0.7698(4) 0.11887(17) 0.0632(9) Uani 1 1 d . . .
O2 O -0.1980(9) 0.6191(6) 0.5497(3) 0.1039(14) Uani 1 1 d . . .
O3 O -0.4193(7) 0.7932(6) 0.5613(2) 0.0944(12) Uani 1 1 d . . .
N1 N 0.4028(6) 1.0078(5) 0.1430(2) 0.0588(9) Uani 1 1 d . . .
N2 N -0.2817(7) 0.7232(6) 0.5212(3) 0.0695(11) Uani 1 1 d . . .
C1 C 0.2284(11) 1.2570(7) 0.1741(3) 0.0769(13) Uani 1 1 d . . .
C2 C 0.2477(7) 1.0851(6) 0.2003(3) 0.0557(10) Uani 1 1 d . . .
H2 H 0.3209 1.1211 0.2650 0.067 Uiso 1 1 calc R . .
C3 C 0.2669(7) 0.8380(6) 0.1011(3) 0.0550(10) Uani 1 1 d . . .
C4 C 0.3412(9) 0.7058(7) 0.0330(3) 0.0761(13) Uani 1 1 d . . .
H4A H 0.2484 0.6812 -0.0261 0.114 Uiso 1 1 calc R . .
H4B H 0.3067 0.5878 0.0509 0.114 Uiso 1 1 calc R . .
H4C H 0.5172 0.7619 0.0298 0.114 Uiso 1 1 calc R . .
C5 C -0.0101(7) 0.9198(6) 0.1857(2) 0.0533(10) Uani 1 1 d . . .
H5 H -0.1392 0.9571 0.1589 0.064 Uiso 1 1 calc R . .
C6 C -0.0864(6) 0.8586(5) 0.2711(2) 0.0492(9) Uani 1 1 d . . .
C7 C 0.0006(8) 0.7351(6) 0.3039(3) 0.0670(12) Uani 1 1 d . . .
H7 H 0.1041 0.6830 0.2709 0.080 Uiso 1 1 calc R . .
C8 C -0.0645(9) 0.6874(7) 0.3857(3) 0.0722(13) Uani 1 1 d . . .
H8 H -0.0060 0.6040 0.4077 0.087 Uiso 1 1 calc R . .
C9 C -0.2165(7) 0.7662(5) 0.4328(2) 0.0551(10) Uani 1 1 d . . .
C10 C -0.3047(8) 0.8897(7) 0.4020(3) 0.0710(13) Uani 1 1 d . . .
H10 H -0.4078 0.9419 0.4353 0.085 Uiso 1 1 calc R . .
C11 C -0.2381(8) 0.9352(7) 0.3208(3) 0.0684(12) Uani 1 1 d . . .
H11 H -0.2968 1.0191 0.2993 0.082 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 0.148(3) 0.0532(19) 0.132(3) 0.0313(19) 0.012(2) 0.0017(18)
F2 0.136(3) 0.097(2) 0.081(2) 0.0522(17) 0.0150(17) 0.053(2)
F3 0.180(3) 0.092(2) 0.119(3) 0.029(2) 0.048(3) 0.086(2)
O1 0.0655(17) 0.0590(18) 0.0503(15) 0.0038(12) 0.0113(12) 0.0099(13)
O2 0.153(4) 0.102(3) 0.083(2) 0.058(2) 0.026(2) 0.057(3)
O3 0.122(3) 0.113(3) 0.063(2) 0.0350(19) 0.038(2) 0.050(3)
N1 0.0594(18) 0.058(2) 0.059(2) 0.0176(16) 0.0097(15) 0.0190(16)
N2 0.083(2) 0.065(2) 0.057(2) 0.0233(18) 0.0091(18) 0.017(2)
C1 0.108(4) 0.059(3) 0.072(3) 0.020(2) 0.020(3) 0.038(3)
C2 0.065(2) 0.051(2) 0.047(2) 0.0130(17) 0.0052(17) 0.0167(18)
C3 0.060(2) 0.060(3) 0.047(2) 0.0182(18) 0.0083(16) 0.0222(19)
C4 0.090(3) 0.073(3) 0.067(3) 0.015(2) 0.019(2) 0.032(3)
C5 0.058(2) 0.057(2) 0.045(2) 0.0130(17) 0.0049(16) 0.0212(17)
C6 0.0523(19) 0.048(2) 0.0460(19) 0.0108(16) 0.0052(15) 0.0169(16)
C7 0.086(3) 0.063(3) 0.073(3) 0.030(2) 0.032(2) 0.043(2)
C8 0.102(3) 0.062(3) 0.071(3) 0.031(2) 0.021(2) 0.043(3)
C9 0.066(2) 0.050(2) 0.047(2) 0.0156(17) 0.0083(17) 0.0156(18)
C10 0.077(3) 0.095(4) 0.062(3) 0.030(2) 0.027(2) 0.048(3)
C11 0.077(3) 0.093(3) 0.062(2) 0.037(2) 0.023(2) 0.052(3)

_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 C1 1.325(6) . ?
F2 C1 1.341(6) . ?
F3 C1 1.329(6) . ?
O1 C3 1.353(5) . ?
O1 C5 1.440(5) . ?
O2 N2 1.204(5) . ?
O3 N2 1.213(5) . ?
N1 C3 1.265(5) . ?
N1 C2 1.450(5) . ?
N2 C9 1.472(5) . ?
C1 C2 1.495(6) . ?
C2 C5 1.549(6) . ?
C2 H2 0.9800 . ?
C3 C4 1.466(6) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.495(5) . ?
C5 H5 0.9800 . ?
C6 C11 1.373(5) . ?
C6 C7 1.379(6) . ?
C7 C8 1.389(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.366(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.368(6) . ?
C10 C11 1.378(6) . ?
C10 H10 0.9300 . ?
C11 H11 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
C3 O1 C5 107.4(3) . . ?
C3 N1 C2 106.9(3) . . ?
O2 N2 O3 123.2(4) . . ?
O2 N2 C9 118.5(4) . . ?
O3 N2 C9 118.3(4) . . ?
F1 C1 F3 107.9(4) . . ?
F1 C1 F2 105.8(4) . . ?
F3 C1 F2 105.6(4) . . ?
F1 C1 C2 113.1(4) . . ?
F3 C1 C2 111.6(4) . . ?
F2 C1 C2 112.3(4) . . ?
N1 C2 C1 110.6(3) . . ?
N1 C2 C5 105.6(3) . . ?
C1 C2 C5 112.3(4) . . ?
N1 C2 H2 109.4 . . ?
C1 C2 H2 109.4 . . ?
C5 C2 H2 109.4 . . ?
N1 C3 O1 117.9(3) . . ?
N1 C3 C4 126.4(4) . . ?
O1 C3 C4 115.7(3) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O1 C5 C6 111.7(3) . . ?
O1 C5 C2 102.2(3) . . ?
C6 C5 C2 114.3(3) . . ?
O1 C5 H5 109.5 . . ?
C6 C5 H5 109.5 . . ?
C2 C5 H5 109.5 . . ?
C11 C6 C7 119.0(4) . . ?
C11 C6 C5 118.9(4) . . ?
C7 C6 C5 122.1(3) . . ?
C6 C7 C8 120.8(4) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C9 C8 C7 118.4(4) . . ?
C9 C8 H8 120.8 . . ?
C7 C8 H8 120.8 . . ?
C8 C9 C10 122.0(4) . . ?
C8 C9 N2 119.5(4) . . ?
C10 C9 N2 118.4(4) . . ?
C9 C10 C11 118.7(4) . . ?
C9 C10 H10 120.6 . . ?
C11 C10 H10 120.6 . . ?
C6 C11 C10 121.1(4) . . ?
C6 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?

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
C3 N1 C2 C1 -119.7(4) . . . . ?
C3 N1 C2 C5 2.0(4) . . . . ?
F1 C1 C2 N1 -61.5(5) . . . . ?
F3 C1 C2 N1 176.5(4) . . . . ?
F2 C1 C2 N1 58.1(5) . . . . ?
F1 C1 C2 C5 -179.2(4) . . . . ?
F3 C1 C2 C5 58.9(5) . . . . ?
F2 C1 C2 C5 -59.5(5) . . . . ?
C2 N1 C3 O1 -1.2(5) . . . . ?
C2 N1 C3 C4 177.8(4) . . . . ?
C5 O1 C3 N1 -0.1(5) . . . . ?
C5 O1 C3 C4 -179.3(4) . . . . ?
C3 O1 C5 C6 -121.2(3) . . . . ?
C3 O1 C5 C2 1.3(4) . . . . ?
N1 C2 C5 O1 -2.0(4) . . . . ?
C1 C2 C5 O1 118.6(4) . . . . ?
N1 C2 C5 C6 118.8(3) . . . . ?
C1 C2 C5 C6 -120.6(4) . . . . ?
O1 C5 C6 C11 -149.6(4) . . . . ?
C2 C5 C6 C11 95.1(4) . . . . ?
O1 C5 C6 C7 33.7(5) . . . . ?
C2 C5 C6 C7 -81.7(5) . . . . ?
C11 C6 C7 C8 0.3(7) . . . . ?
C5 C6 C7 C8 177.1(4) . . . . ?
C6 C7 C8 C9 -0.1(7) . . . . ?
C7 C8 C9 C10 -0.1(7) . . . . ?
C7 C8 C9 N2 -178.0(4) . . . . ?
O2 N2 C9 C8 0.1(6) . . . . ?
O3 N2 C9 C8 -179.2(4) . . . . ?
O2 N2 C9 C10 -177.8(4) . . . . ?
O3 N2 C9 C10 2.9(6) . . . . ?
C8 C9 C10 C11 0.1(7) . . . . ?
N2 C9 C10 C11 178.0(4) . . . . ?
C7 C6 C11 C10 -0.3(7) . . . . ?
C5 C6 C11 C10 -177.2(4) . . . . ?
C9 C10 C11 C6 0.1(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.386
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.098
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_141014a
_database_code_depnum_ccdc_archive 'CCDC 1042103'
_audit_update_record             
;
2015-01-05 deposited with the CCDC.
2015-04-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H9 Cl F3 N O2'
_chemical_formula_weight         279.64

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           MONOCLINIC
_symmetry_space_group_name_H-M   P2(1)/c

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                   7.764(6)
_cell_length_b                   22.824(17)
_cell_length_c                   7.398(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.915(9)
_cell_angle_gamma                90.00
_cell_volume                     1207.5(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    2202
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             568
_exptl_absorpt_coefficient_mu    0.348
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9497
_exptl_absorpt_correction_T_max  0.9896
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      294(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  'Rigaku Mercury375R'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 13.6612
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12636
_diffrn_reflns_av_R_equivalents  0.1985
_diffrn_reflns_av_sigmaI/netI    0.1033
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.12
_diffrn_reflns_theta_max         27.49
_reflns_number_total             2761
_reflns_number_gt                1811
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       CrystalClear
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0333P)²+0.2904P] where P=(Fo²+2Fc²)/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         2761
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0954
_refine_ls_R_factor_gt           0.0595
_refine_ls_wR_factor_ref         0.1686
_refine_ls_wR_factor_gt          0.1462
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.3353(4) 0.70656(13) 0.8173(4) 0.0512(7) Uani 1 1 d . . .
C2 C -0.2276(4) 0.75328(13) 0.8047(4) 0.0569(7) Uani 1 1 d . . .
H2 H -0.2827 0.7895 0.7596 0.068 Uiso 1 1 calc R . .
C3 C -0.0378(4) 0.74584(12) 0.8595(5) 0.0553(7) Uani 1 1 d . . .
H3 H 0.0361 0.7771 0.8522 0.066 Uiso 1 1 calc R . .
C4 C 0.0426(4) 0.69172(11) 0.9253(4) 0.0466(6) Uani 1 1 d . . .
H4 H 0.1706 0.6867 0.9616 0.056 Uiso 1 1 calc R . .
C5 C -0.0661(3) 0.64518(10) 0.9375(4) 0.0401(5) Uani 1 1 d . . .
C6 C -0.2584(3) 0.65237(11) 0.8839(4) 0.0448(6) Uani 1 1 d . . .
H6 H -0.3325 0.6214 0.8930 0.054 Uiso 1 1 calc R . .
C7 C 0.0202(3) 0.58834(11) 1.0277(4) 0.0428(6) Uani 1 1 d . . .
C8 C 0.3246(3) 0.54068(11) 1.1697(4) 0.0492(6) Uani 1 1 d . . .
H8A H 0.3940 0.5135 1.1230 0.059 Uiso 1 1 calc R . .
H8B H 0.2624 0.5184 1.2384 0.059 Uiso 1 1 calc R . .
C9 C 0.4563(4) 0.58326(15) 1.3075(5) 0.0676(9) Uani 1 1 d . . .
C10 C 0.2100(4) 0.56964(12) 0.8266(4) 0.0496(7) Uani 1 1 d . . .
C11 C 0.0481(5) 0.58346(16) 0.6379(5) 0.0658(8) Uani 1 1 d . . .
H11A H 0.0457 0.6248 0.6125 0.099 Uiso 1 1 calc R . .
H11B H -0.0666 0.5721 0.6486 0.099 Uiso 1 1 calc R . .
H11C H 0.0619 0.5623 0.5321 0.099 Uiso 1 1 calc R . .
Cl1 Cl -0.57401(11) 0.71680(4) 0.75303(15) 0.0784(3) Uani 1 1 d . . .
F1 F 0.5757(3) 0.55708(11) 1.4669(4) 0.1093(10) Uani 1 1 d . . .
F2 F 0.5552(3) 0.61250(12) 1.2280(4) 0.1114(9) Uani 1 1 d . . .
F3 F 0.3677(4) 0.62346(11) 1.3697(4) 0.1081(9) Uani 1 1 d . . .
N1 N 0.1849(3) 0.57075(9) 1.0028(3) 0.0430(5) Uani 1 1 d . . .
O1 O -0.0385(3) 0.56055(9) 1.1305(3) 0.0616(6) Uani 1 1 d . . .
O2 O 0.3599(3) 0.55557(10) 0.8257(4) 0.0731(7) Uani 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
C1 0.0491(14) 0.0607(17) 0.0458(15) 0.0007(12) 0.0207(11) 0.0141(13)
C2 0.0715(19) 0.0499(15) 0.0516(17) 0.0095(13) 0.0266(14) 0.0208(15)
C3 0.0673(17) 0.0441(14) 0.0602(18) 0.0018(12) 0.0310(14) -0.0011(14)
C4 0.0416(12) 0.0489(14) 0.0511(16) 0.0002(12) 0.0198(11) 0.0005(11)
C5 0.0405(12) 0.0421(12) 0.0399(13) -0.0020(10) 0.0182(10) 0.0034(11)
C6 0.0416(12) 0.0492(14) 0.0464(15) 0.0010(11) 0.0204(11) 0.0043(11)
C7 0.0384(12) 0.0415(13) 0.0475(15) -0.0006(11) 0.0158(10) -0.0014(10)
C8 0.0402(13) 0.0441(13) 0.0583(17) 0.0107(12) 0.0137(11) 0.0038(11)
C9 0.0538(17) 0.0635(19) 0.071(2) 0.0122(16) 0.0085(15) -0.0036(15)
C10 0.0487(14) 0.0445(13) 0.0594(18) 0.0007(12) 0.0252(13) 0.0061(12)
C11 0.0656(18) 0.084(2) 0.0466(18) -0.0075(15) 0.0209(14) 0.0077(17)
Cl1 0.0506(4) 0.0936(7) 0.0911(7) 0.0143(5) 0.0278(4) 0.0310(4)
F1 0.0759(14) 0.1133(18) 0.0895(18) 0.0318(13) -0.0215(12) -0.0130(13)
F2 0.0996(17) 0.1118(18) 0.110(2) 0.0085(15) 0.0273(15) -0.0585(15)
F3 0.1161(19) 0.0934(15) 0.0905(19) -0.0319(13) 0.0138(15) 0.0030(15)
N1 0.0366(10) 0.0383(10) 0.0524(13) 0.0033(9) 0.0154(9) 0.0051(9)
O1 0.0557(11) 0.0625(12) 0.0738(15) 0.0206(10) 0.0330(11) 0.0066(10)
O2 0.0622(13) 0.0825(16) 0.0899(18) 0.0162(13) 0.0464(12) 0.0269(12)

_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 C6 1.379(4) . ?
C1 C2 1.380(4) . ?
C1 Cl1 1.741(3) . ?
C2 C3 1.379(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.384(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.397(3) . ?
C5 C7 1.493(4) . ?
C6 H6 0.9300 . ?
C7 O1 1.208(3) . ?
C7 N1 1.419(3) . ?
C8 N1 1.459(3) . ?
C8 C9 1.489(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 F2 1.316(4) . ?
C9 F1 1.325(4) . ?
C9 F3 1.332(4) . ?
C10 O2 1.210(3) . ?
C10 N1 1.391(4) . ?
C10 C11 1.504(4) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?

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
C6 C1 C2 121.9(3) . . ?
C6 C1 Cl1 119.0(2) . . ?
C2 C1 Cl1 119.1(2) . . ?
C3 C2 C1 119.4(3) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 C4 119.8(3) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 120.4(2) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 120.2(2) . . ?
C4 C5 C7 121.2(2) . . ?
C6 C5 C7 118.2(2) . . ?
C1 C6 C5 118.2(3) . . ?
C1 C6 H6 120.9 . . ?
C5 C6 H6 120.9 . . ?
O1 C7 N1 120.9(2) . . ?
O1 C7 C5 121.6(2) . . ?
N1 C7 C5 117.3(2) . . ?
N1 C8 C9 111.0(2) . . ?
N1 C8 H8A 109.4 . . ?
C9 C8 H8A 109.4 . . ?
N1 C8 H8B 109.4 . . ?
C9 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
F2 C9 F1 107.4(3) . . ?
F2 C9 F3 106.0(3) . . ?
F1 C9 F3 106.2(3) . . ?
F2 C9 C8 112.9(3) . . ?
F1 C9 C8 111.8(3) . . ?
F3 C9 C8 112.1(3) . . ?
O2 C10 N1 119.7(3) . . ?
O2 C10 C11 120.6(3) . . ?
N1 C10 C11 119.7(2) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 N1 C7 126.1(2) . . ?
C10 N1 C8 117.1(2) . . ?
C7 N1 C8 115.7(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
C6 C1 C2 C3 0.2(4) . . . . ?
Cl1 C1 C2 C3 178.6(2) . . . . ?
C1 C2 C3 C4 0.4(4) . . . . ?
C2 C3 C4 C5 -0.4(4) . . . . ?
C3 C4 C5 C6 -0.2(4) . . . . ?
C3 C4 C5 C7 -173.5(3) . . . . ?
C2 C1 C6 C5 -0.7(4) . . . . ?
Cl1 C1 C6 C5 -179.1(2) . . . . ?
C4 C5 C6 C1 0.7(4) . . . . ?
C7 C5 C6 C1 174.2(2) . . . . ?
C4 C5 C7 O1 140.7(3) . . . . ?
C6 C5 C7 O1 -32.8(4) . . . . ?
C4 C5 C7 N1 -33.7(4) . . . . ?
C6 C5 C7 N1 152.9(2) . . . . ?
N1 C8 C9 F2 -63.3(4) . . . . ?
N1 C8 C9 F1 175.4(3) . . . . ?
N1 C8 C9 F3 56.3(4) . . . . ?
O2 C10 N1 C7 177.5(3) . . . . ?
C11 C10 N1 C7 -5.1(4) . . . . ?
O2 C10 N1 C8 -15.4(4) . . . . ?
C11 C10 N1 C8 162.0(2) . . . . ?
O1 C7 N1 C10 136.5(3) . . . . ?
C5 C7 N1 C10 -49.1(3) . . . . ?
O1 C7 N1 C8 -30.8(4) . . . . ?
C5 C7 N1 C8 143.6(2) . . . . ?
C9 C8 N1 C10 102.6(3) . . . . ?
C9 C8 N1 C7 -89.0(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.063

