# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014

 
data_tfs-4f
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C14 H13 Cl O3'
_chemical_formula_sum
 'C14 H13 Cl O3'
_chemical_formula_weight          264.70
 
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'
 'O'  'O'   0.0106   0.0060
 '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            orthorhombic
_symmetry_space_group_name_H-M    'p_c_a_21'
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, -y, z+1/2'
 '-x+1/2, y, z+1/2'
 'x+1/2, -y, z'
 
_cell_length_a                    14.234(4)
_cell_length_b                    4.0143(10)
_cell_length_c                    22.047(5)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      1259.8(5)
_cell_formula_units_Z             4
_cell_measurement_temperature     293(2)
_cell_measurement_reflns_used     18
_cell_measurement_theta_min       2.9530
_cell_measurement_theta_max       28.3702
 
_exptl_crystal_description        orthorhombic
_exptl_crystal_colour             white
_exptl_crystal_size_max           0.3
_exptl_crystal_size_mid           0.2
_exptl_crystal_size_min           0.1
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.385
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              496
_exptl_absorpt_coefficient_mu     0.300
_exptl_absorpt_correction_type    none
_exptl_absorpt_correction_T_min   ?
_exptl_absorpt_correction_T_max   ?
_exptl_absorpt_process_details    ?
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       293(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   'Xcalibur, Eos'
_diffrn_measurement_method        'ω scans'
_diffrn_detector_area_resol_mean  16.0938
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             3244
_diffrn_reflns_av_R_equivalents   0.0542
_diffrn_reflns_av_sigmaI/netI     0.1228
_diffrn_reflns_limit_h_min        -18
_diffrn_reflns_limit_h_max        18
_diffrn_reflns_limit_k_min        -2
_diffrn_reflns_limit_k_max        5
_diffrn_reflns_limit_l_min        -29
_diffrn_reflns_limit_l_max        24
_diffrn_reflns_theta_min          3.01
_diffrn_reflns_theta_max          29.04
_reflns_number_total              2256
_reflns_number_gt                 1169
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_cell_refinement        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction         
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_structure_solution     ?
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
 
_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     mixed
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        ?
_refine_ls_abs_structure_details
 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack    -0.1(4)
_refine_ls_number_reflns          2256
_refine_ls_number_parameters      163
_refine_ls_number_restraints      1
_refine_ls_R_factor_all           0.1896
_refine_ls_R_factor_gt            0.0958
_refine_ls_wR_factor_ref          0.3824
_refine_ls_wR_factor_gt           0.2314
_refine_ls_goodness_of_fit_ref    1.130
_refine_ls_restrained_S_all       1.130
_refine_ls_shift/su_max           0.018
_refine_ls_shift/su_mean          0.004
 
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
Cl01 Cl 1.0079(3) 0.2040(8) 0.8033(2) 0.0789(12) Uani 1 1 d . . .
O002 O 0.7260(4) 0.4313(18) 0.9921(3) 0.0455(18) Uani 1 1 d . . .
O003 O 0.7797(6) 0.011(2) 1.1683(5) 0.076(3) Uani 1 1 d . . .
C1 C 0.9483(6) 0.153(2) 0.9192(5) 0.036(2) Uani 1 1 d . . .
O1 O 0.9632(4) -0.041(2) 1.0477(4) 0.058(2) Uani 1 1 d . . .
C006 C 0.8216(7) 0.219(2) 1.0723(5) 0.039(2) Uani 1 1 d . . .
C007 C 0.9242(8) 0.260(2) 0.8612(5) 0.043(2) Uani 1 1 d . . .
C008 C 0.8401(9) 0.406(2) 0.8454(5) 0.049(3) Uani 1 1 d . . .
C009 C 0.7391(6) 0.358(2) 1.0524(5) 0.036(2) Uani 1 1 d . . .
C010 C 0.7961(7) 0.365(2) 0.9506(5) 0.042(2) Uani 1 1 d . . .
C011 C 0.7768(8) 0.452(3) 0.8916(5) 0.048(3) Uani 1 1 d . . .
H011 H 0.7186 0.5456 0.8827 0.058 Uiso 1 1 calc R . .
C012 C 0.8357(8) 0.161(3) 1.1379(5) 0.048(3) Uani 1 1 d . . .
C013 C 0.8814(7) 0.2089(19) 0.9653(5) 0.036(2) Uani 1 1 d . . .
C014 C 0.8944(7) 0.116(2) 1.0304(4) 0.036(2) Uani 1 1 d . . .
C015 C 0.9233(9) 0.293(3) 1.1643(6) 0.061(3) Uani 1 1 d . . .
H01A H 0.9253 0.2420 1.2068 0.091 Uiso 1 1 calc R . .
H01B H 0.9253 0.5303 1.1589 0.091 Uiso 1 1 calc R . .
H01C H 0.9762 0.1933 1.1444 0.091 Uiso 1 1 calc R . .
C016 C 0.8173(12) 0.516(3) 0.7815(6) 0.072(4) Uani 1 1 d . . .
H01D H 0.8691 0.4644 0.7552 0.108 Uiso 1 1 calc R . .
H01E H 0.8062 0.7519 0.7810 0.108 Uiso 1 1 calc R . .
H01F H 0.7621 0.4018 0.7676 0.108 Uiso 1 1 calc R . .
C017 C 0.6567(6) 0.463(3) 1.0874(7) 0.055(3) Uani 1 1 d . . .
H01G H 0.6099 0.5509 1.0604 0.083 Uiso 1 1 calc R . .
H01H H 0.6750 0.6328 1.1158 0.083 Uiso 1 1 calc R . .
H01I H 0.6315 0.2760 1.1090 0.083 Uiso 1 1 calc R . .
C018 C 1.0404(6) -0.008(3) 0.9311(6) 0.051(3) Uani 1 1 d . . .
H01J H 1.0451 -0.0629 0.9734 0.077 Uiso 1 1 calc R . .
H01K H 1.0902 0.1413 0.9202 0.077 Uiso 1 1 calc R . .
H01L H 1.0453 -0.2083 0.9074 0.077 Uiso 1 1 calc R . .
 
 
_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
Cl01 C007 1.759(11) . ?
O002 C009 1.374(12) . ?
O002 C010 1.379(12) . ?
O003 C012 1.201(13) . ?
C1 C007 1.392(15) . ?
C1 C013 1.410(13) . ?
C1 C018 1.485(14) . ?
O1 C014 1.226(11) . ?
C006 C009 1.372(14) . ?
C006 C014 1.448(13) . ?
C006 C012 1.480(15) . ?
C007 C008 1.378(16) . ?
C008 C011 1.373(16) . ?
C008 C016 1.514(16) . ?
C009 C017 1.467(14) . ?
C010 C011 1.374(15) . ?
C010 C013 1.405(14) . ?
C011 H011 0.9300 . ?
C012 C015 1.475(17) . ?
C013 C014 1.494(14) . ?
C015 H01A 0.9600 . ?
C015 H01B 0.9600 . ?
C015 H01C 0.9600 . ?
C016 H01D 0.9600 . ?
C016 H01E 0.9600 . ?
C016 H01F 0.9600 . ?
C017 H01G 0.9600 . ?
C017 H01H 0.9600 . ?
C017 H01I 0.9600 . ?
C018 H01J 0.9600 . ?
C018 H01K 0.9600 . ?
C018 H01L 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
C009 O002 C010 120.2(7) . . ?
C007 C1 C013 116.5(9) . . ?
C007 C1 C018 120.9(10) . . ?
C013 C1 C018 122.6(10) . . ?
C009 C006 C014 121.6(10) . . ?
C009 C006 C012 119.5(9) . . ?
C014 C006 C012 118.8(9) . . ?
C008 C007 C1 125.2(10) . . ?
C008 C007 Cl01 117.4(9) . . ?
C1 C007 Cl01 117.4(8) . . ?
C011 C008 C007 116.2(10) . . ?
C011 C008 C016 120.7(11) . . ?
C007 C008 C016 123.1(11) . . ?
O002 C009 C006 120.8(9) . . ?
O002 C009 C017 109.9(8) . . ?
C006 C009 C017 129.2(11) . . ?
C011 C010 O002 115.7(9) . . ?
C011 C010 C013 120.3(10) . . ?
O002 C010 C013 124.0(10) . . ?
C008 C011 C010 122.4(10) . . ?
C008 C011 H011 118.8 . . ?
C010 C011 H011 118.8 . . ?
O003 C012 C015 121.4(12) . . ?
O003 C012 C006 122.2(11) . . ?
C015 C012 C006 116.3(9) . . ?
C010 C013 C1 119.3(9) . . ?
C010 C013 C014 116.1(9) . . ?
C1 C013 C014 124.6(8) . . ?
O1 C014 C006 121.3(9) . . ?
O1 C014 C013 121.8(9) . . ?
C006 C014 C013 116.9(8) . . ?
C012 C015 H01A 109.5 . . ?
C012 C015 H01B 109.5 . . ?
H01A C015 H01B 109.5 . . ?
C012 C015 H01C 109.5 . . ?
H01A C015 H01C 109.5 . . ?
H01B C015 H01C 109.5 . . ?
C008 C016 H01D 109.5 . . ?
C008 C016 H01E 109.5 . . ?
H01D C016 H01E 109.5 . . ?
C008 C016 H01F 109.5 . . ?
H01D C016 H01F 109.5 . . ?
H01E C016 H01F 109.5 . . ?
C009 C017 H01G 109.5 . . ?
C009 C017 H01H 109.5 . . ?
H01G C017 H01H 109.5 . . ?
C009 C017 H01I 109.5 . . ?
H01G C017 H01I 109.5 . . ?
H01H C017 H01I 109.5 . . ?
C1 C018 H01J 109.5 . . ?
C1 C018 H01K 109.5 . . ?
H01J C018 H01K 109.5 . . ?
C1 C018 H01L 109.5 . . ?
H01J C018 H01L 109.5 . . ?
H01K C018 H01L 109.5 . . ?
 
_diffrn_measured_fraction_theta_max    0.830
_diffrn_reflns_theta_full              25.00
_diffrn_measured_fraction_theta_full   0.985
_refine_diff_density_max    0.719
_refine_diff_density_min   -0.843
_refine_diff_density_rms    0.183
