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

#######################################################################
#
#                 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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H15 Cl O2'
_chemical_formula_sum            'C14 H15 Cl O2'
_chemical_formula_weight         250.72

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           Monoclinic
_symmetry_space_group_name_H-M   p_1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'

_cell_length_a                   4.433(6)
_cell_length_b                   13.761(10)
_cell_length_c                   10.298(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.05(12)
_cell_angle_gamma                90.00
_cell_volume                     627.8(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    575
_cell_measurement_theta_min      2.9545
_cell_measurement_theta_max      28.7268

_exptl_crystal_description       Monoclinic
_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      1.33
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             264
_exptl_absorpt_coefficient_mu    0.291
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.33311
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_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            2719
_diffrn_reflns_av_R_equivalents  0.0178
_diffrn_reflns_av_sigmaI/netI    0.0428
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.96
_diffrn_reflns_theta_max         28.79
_reflns_number_total             2536
_reflns_number_gt                1925
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_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)+(0.0718P)²+0.0498P] 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   -0.03(10)
_refine_ls_number_reflns         2536
_refine_ls_number_parameters     307
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0657
_refine_ls_R_factor_gt           0.0459
_refine_ls_wR_factor_ref         0.1344
_refine_ls_wR_factor_gt          0.1124
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_restrained_S_all      0.981
_refine_ls_shift/su_max          0.001
_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
Cl01 Cl 1.4298(4) -0.15144(13) 0.18822(16) 0.0737(5) Uani 1 1 d . . .
Cl02 Cl 0.1698(4) 0.34818(13) 0.73389(16) 0.0746(5) Uani 1 1 d . . .
CL03 C 0.6847(13) 0.3329(4) 0.2794(5) 0.0504(14) Uani 1 1 d . . .
O004 O 0.6867(8) 0.0214(2) 0.5870(3) 0.0494(9) Uani 1 1 d . . .
O005 O 0.9098(7) 0.5213(2) 0.3347(3) 0.0487(9) Uani 1 1 d . . .
O006 C 1.1716(11) -0.1579(4) 0.4229(5) 0.0432(13) Uani 1 1 d . . .
O007 O 0.9927(10) -0.2506(3) 0.6702(4) 0.0716(12) Uani 1 1 d . . .
O008 C 0.8639(10) -0.0244(3) 0.4990(5) 0.0422(12) Uani 1 1 d . . .
O009 C 0.7338(11) 0.4756(4) 0.4225(5) 0.0437(12) Uani 1 1 d . . .
C010 O 0.6051(10) 0.2495(3) 0.2527(4) 0.0746(13) Uani 1 1 d . . .
C011 C 0.6094(11) 0.3831(4) 0.4014(5) 0.0436(12) Uani 1 1 d . . .
C012 C 0.5060(12) 0.4904(4) 0.6312(5) 0.0499(13) Uani 1 1 d . . .
C013 C 0.9871(11) -0.1167(3) 0.5214(5) 0.0411(12) Uani 1 1 d . . .
C014 C 1.0902(12) -0.0104(4) 0.2915(5) 0.0497(14) Uani 1 1 d . . .
C015 C 0.9728(11) 0.4773(4) 0.2192(5) 0.0498(13) Uani 1 1 d . . .
C016 C 0.6863(11) 0.5289(4) 0.5353(5) 0.0473(13) Uani 1 1 d . . .
H016 H 0.7743 0.5898 0.5466 0.057 Uiso 1 1 calc R . .
C017 C 0.6260(12) -0.0242(4) 0.7022(5) 0.0505(14) Uani 1 1 d . . .
C018 C 0.4275(12) 0.3423(4) 0.4988(6) 0.0440(13) Uani 1 1 d . . .
C019 C 1.2131(11) -0.1030(4) 0.3128(5) 0.0500(14) Uani 1 1 d . . .
C020 C 0.8676(11) 0.3887(4) 0.1891(5) 0.0517(13) Uani 1 1 d . . .
C021 C 0.7296(12) -0.1126(4) 0.7332(5) 0.0504(13) Uani 1 1 d . . .
C022 C 0.2846(13) 0.2423(4) 0.4842(6) 0.0624(16) Uani 1 1 d . . .
H02A H 0.3349 0.2149 0.4020 0.094 Uiso 1 1 calc R . .
H02B H 0.0693 0.2480 0.4884 0.094 Uiso 1 1 calc R . .
H02C H 0.3594 0.2009 0.5531 0.094 Uiso 1 1 calc R . .
C023 C 0.9128(12) 0.0283(4) 0.3863(5) 0.0471(13) Uani 1 1 d . . .
H023 H 0.8263 0.0894 0.3748 0.057 Uiso 1 1 calc R . .
C027 C 0.4601(15) 0.5470(5) 0.7526(6) 0.0717(18) Uani 1 1 d . . .
H02D H 0.3311 0.5112 0.8082 0.107 Uiso 1 1 calc R . .
H02E H 0.3682 0.6083 0.7309 0.107 Uiso 1 1 calc R . .
H02F H 0.6516 0.5579 0.7967 0.107 Uiso 1 1 calc R . .
C031 C 0.3848(12) 0.3965(4) 0.6084(5) 0.0508(13) Uani 1 1 d . . .
C032 C 1.1370(16) 0.0479(5) 0.1690(6) 0.0742(19) Uani 1 1 d . . .
H03A H 1.0351 0.1093 0.1750 0.111 Uiso 1 1 calc R . .
H03B H 1.0567 0.0127 0.0951 0.111 Uiso 1 1 calc R . .
H03C H 1.3489 0.0589 0.1593 0.111 Uiso 1 1 calc R . .
C033 C 1.3160(14) -0.2575(4) 0.4387(6) 0.0651(16) Uani 1 1 d . . .
H03D H 1.2625 -0.2850 0.5204 0.098 Uiso 1 1 calc R . .
H03E H 1.5314 -0.2513 0.4364 0.098 Uiso 1 1 calc R . .
H03F H 1.2452 -0.2991 0.3693 0.098 Uiso 1 1 calc R . .
C034 C 0.9109(13) -0.1664(4) 0.6427(5) 0.0503(14) Uani 1 1 d . . .
C900 C 0.9438(18) 0.3381(5) 0.0635(7) 0.081(2) Uani 1 1 d . . .
H90A H 0.8494 0.2753 0.0603 0.121 Uiso 1 1 calc R . .
H90B H 1.1586 0.3306 0.0600 0.121 Uiso 1 1 calc R . .
H90C H 0.8715 0.3763 -0.0091 0.121 Uiso 1 1 calc R . .
C555 C 0.6605(18) -0.1614(5) 0.8600(6) 0.077(2) Uani 1 1 d . . .
H55A H 0.7547 -0.2242 0.8637 0.116 Uiso 1 1 calc R . .
H55B H 0.4460 -0.1687 0.8659 0.116 Uiso 1 1 calc R . .
H55C H 0.7368 -0.1222 0.9310 0.116 Uiso 1 1 calc R . .
C666 C 0.4297(12) 0.0427(4) 0.7801(6) 0.0579(15) Uani 1 1 d . . .
H66A H 0.3282 0.0049 0.8449 0.069 Uiso 1 1 calc R . .
H66B H 0.2762 0.0714 0.7225 0.069 Uiso 1 1 calc R . .
C888 C 1.1629(13) 0.5433(4) 0.1416(6) 0.0617(16) Uani 1 1 d . . .
H88A H 1.3160 0.5724 0.1989 0.074 Uiso 1 1 calc R . .
H88B H 1.2656 0.5051 0.0775 0.074 Uiso 1 1 calc R . .
C777 C 0.6101(15) 0.1235(5) 0.8475(7) 0.081(2) Uani 1 1 d . . .
H77A H 0.4762 0.1646 0.8941 0.122 Uiso 1 1 calc R . .
H77B H 0.7107 0.1613 0.7837 0.122 Uiso 1 1 calc R . .
H77C H 0.7572 0.0956 0.9072 0.122 Uiso 1 1 calc R . .
C999 C 0.9906(15) 0.6223(5) 0.0735(7) 0.0749(19) Uani 1 1 d . . .
H99A H 1.1267 0.6621 0.0263 0.112 Uiso 1 1 calc R . .
H99B H 0.8911 0.6615 0.1362 0.112 Uiso 1 1 calc R . .
H99C H 0.8428 0.5944 0.0142 0.112 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 C019 1.761(5) . ?
Cl02 C031 1.763(6) . ?
CL03 C010 1.229(6) . ?
CL03 C020 1.472(8) . ?
CL03 C011 1.482(7) . ?
O004 C017 1.377(6) . ?
O004 O008 1.374(6) . ?
O005 C015 1.372(6) . ?
O005 O009 1.368(6) . ?
O006 C019 1.380(8) . ?
O006 C013 1.442(7) . ?
O006 C033 1.518(8) . ?
O007 C034 1.245(7) . ?
O008 C023 1.392(7) . ?
O008 C013 1.399(7) . ?
O009 C011 1.401(6) . ?
O009 C016 1.396(7) . ?
C011 C018 1.424(7) . ?
C012 C016 1.397(7) . ?
C012 C031 1.415(7) . ?
C012 C027 1.493(7) . ?
C013 C034 1.473(7) . ?
C014 C023 1.382(7) . ?
C014 C019 1.400(8) . ?
C014 C032 1.517(8) . ?
C015 C020 1.337(7) . ?
C015 C888 1.492(8) . ?
C016 H016 0.9300 . ?
C017 C021 1.335(8) . ?
C017 C666 1.516(8) . ?
C018 C031 1.372(8) . ?
C018 C022 1.520(7) . ?
C020 C900 1.517(8) . ?
C021 C034 1.454(8) . ?
C021 C555 1.509(8) . ?
C022 H02A 0.9600 . ?
C022 H02B 0.9600 . ?
C022 H02C 0.9600 . ?
C023 H023 0.9300 . ?
C027 H02D 0.9600 . ?
C027 H02E 0.9600 . ?
C027 H02F 0.9600 . ?
C032 H03A 0.9600 . ?
C032 H03B 0.9600 . ?
C032 H03C 0.9600 . ?
C033 H03D 0.9600 . ?
C033 H03E 0.9600 . ?
C033 H03F 0.9600 . ?
C900 H90A 0.9600 . ?
C900 H90B 0.9600 . ?
C900 H90C 0.9600 . ?
C555 H55A 0.9600 . ?
C555 H55B 0.9600 . ?
C555 H55C 0.9600 . ?
C666 C777 1.522(8) . ?
C666 H66A 0.9700 . ?
C666 H66B 0.9700 . ?
C888 C999 1.489(9) . ?
C888 H88A 0.9700 . ?
C888 H88B 0.9700 . ?
C777 H77A 0.9600 . ?
C777 H77B 0.9600 . ?
C777 H77C 0.9600 . ?
C999 H99A 0.9600 . ?
C999 H99B 0.9600 . ?
C999 H99C 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
C010 CL03 C020 120.4(5) . . ?
C010 CL03 C011 123.5(5) . . ?
C020 CL03 C011 116.0(4) . . ?
C017 O004 O008 119.5(4) . . ?
C015 O005 O009 120.5(4) . . ?
C019 O006 C013 117.3(5) . . ?
C019 O006 C033 120.9(5) . . ?
C013 O006 C033 121.8(5) . . ?
O004 O008 C023 114.9(5) . . ?
O004 O008 C013 122.5(5) . . ?
C023 O008 C013 122.6(4) . . ?
O005 O009 C011 123.1(4) . . ?
O005 O009 C016 114.5(4) . . ?
C011 O009 C016 122.4(5) . . ?
O009 C011 C018 118.6(4) . . ?
O009 C011 CL03 117.1(5) . . ?
C018 C011 CL03 124.3(4) . . ?
C016 C012 C031 116.9(4) . . ?
C016 C012 C027 119.5(5) . . ?
C031 C012 C027 123.6(5) . . ?
O008 C013 O006 118.0(4) . . ?
O008 C013 C034 117.4(5) . . ?
O006 C013 C034 124.6(5) . . ?
C023 C014 C019 118.0(5) . . ?
C023 C014 C032 118.8(6) . . ?
C019 C014 C032 123.2(5) . . ?
C020 C015 O005 121.6(5) . . ?
C020 C015 C888 129.1(5) . . ?
O005 C015 C888 109.3(5) . . ?
C012 C016 O009 119.7(4) . . ?
C012 C016 H016 120.1 . . ?
O009 C016 H016 120.1 . . ?
C021 C017 O004 123.1(5) . . ?
C021 C017 C666 128.8(5) . . ?
O004 C017 C666 108.2(5) . . ?
C031 C018 C011 117.6(4) . . ?
C031 C018 C022 120.3(5) . . ?
C011 C018 C022 122.1(5) . . ?
O006 C019 C014 124.3(5) . . ?
O006 C019 Cl01 118.9(4) . . ?
C014 C019 Cl01 116.7(4) . . ?
C015 C020 CL03 121.6(4) . . ?
C015 C020 C900 122.0(6) . . ?
CL03 C020 C900 116.3(5) . . ?
C017 C021 C034 120.2(5) . . ?
C017 C021 C555 122.2(5) . . ?
C034 C021 C555 117.5(6) . . ?
C018 C022 H02A 109.5 . . ?
C018 C022 H02B 109.5 . . ?
H02A C022 H02B 109.5 . . ?
C018 C022 H02C 109.5 . . ?
H02A C022 H02C 109.5 . . ?
H02B C022 H02C 109.5 . . ?
C014 C023 O008 119.8(5) . . ?
C014 C023 H023 120.1 . . ?
O008 C023 H023 120.1 . . ?
C012 C027 H02D 109.5 . . ?
C012 C027 H02E 109.5 . . ?
H02D C027 H02E 109.5 . . ?
C012 C027 H02F 109.5 . . ?
H02D C027 H02F 109.5 . . ?
H02E C027 H02F 109.5 . . ?
C018 C031 C012 124.8(5) . . ?
C018 C031 Cl02 119.4(4) . . ?
C012 C031 Cl02 115.8(4) . . ?
C014 C032 H03A 109.5 . . ?
C014 C032 H03B 109.5 . . ?
H03A C032 H03B 109.5 . . ?
C014 C032 H03C 109.5 . . ?
H03A C032 H03C 109.5 . . ?
H03B C032 H03C 109.5 . . ?
O006 C033 H03D 109.5 . . ?
O006 C033 H03E 109.5 . . ?
H03D C033 H03E 109.5 . . ?
O006 C033 H03F 109.5 . . ?
H03D C033 H03F 109.5 . . ?
H03E C033 H03F 109.5 . . ?
O007 C034 C021 119.4(5) . . ?
O007 C034 C013 123.4(5) . . ?
C021 C034 C013 117.1(5) . . ?
C020 C900 H90A 109.5 . . ?
C020 C900 H90B 109.5 . . ?
H90A C900 H90B 109.5 . . ?
C020 C900 H90C 109.5 . . ?
H90A C900 H90C 109.5 . . ?
H90B C900 H90C 109.5 . . ?
C021 C555 H55A 109.5 . . ?
C021 C555 H55B 109.5 . . ?
H55A C555 H55B 109.5 . . ?
C021 C555 H55C 109.5 . . ?
H55A C555 H55C 109.5 . . ?
H55B C555 H55C 109.5 . . ?
C017 C666 C777 112.5(5) . . ?
C017 C666 H66A 109.1 . . ?
C777 C666 H66A 109.1 . . ?
C017 C666 H66B 109.1 . . ?
C777 C666 H66B 109.1 . . ?
H66A C666 H66B 107.8 . . ?
C999 C888 C015 114.0(5) . . ?
C999 C888 H88A 108.7 . . ?
C015 C888 H88A 108.7 . . ?
C999 C888 H88B 108.7 . . ?
C015 C888 H88B 108.7 . . ?
H88A C888 H88B 107.6 . . ?
C666 C777 H77A 109.5 . . ?
C666 C777 H77B 109.5 . . ?
H77A C777 H77B 109.5 . . ?
C666 C777 H77C 109.5 . . ?
H77A C777 H77C 109.5 . . ?
H77B C777 H77C 109.5 . . ?
C888 C999 H99A 109.5 . . ?
C888 C999 H99B 109.5 . . ?
H99A C999 H99B 109.5 . . ?
C888 C999 H99C 109.5 . . ?
H99A C999 H99C 109.5 . . ?
H99B C999 H99C 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
C017 O004 O008 C023 -179.6(4) . . . . ?
C017 O004 O008 C013 0.0(6) . . . . ?
C015 O005 O009 C011 0.1(7) . . . . ?
C015 O005 O009 C016 -179.6(4) . . . . ?
O005 O009 C011 C018 -179.5(5) . . . . ?
C016 O009 C011 C018 0.1(7) . . . . ?
O005 O009 C011 CL03 2.1(7) . . . . ?
C016 O009 C011 CL03 -178.2(5) . . . . ?
C010 CL03 C011 O009 175.6(5) . . . . ?
C020 CL03 C011 O009 -3.8(7) . . . . ?
C010 CL03 C011 C018 -2.6(9) . . . . ?
C020 CL03 C011 C018 178.0(5) . . . . ?
O004 O008 C013 O006 -179.6(4) . . . . ?
C023 O008 C013 O006 0.0(6) . . . . ?
O004 O008 C013 C034 2.3(6) . . . . ?
C023 O008 C013 C034 -178.1(5) . . . . ?
C019 O006 C013 O008 -0.1(6) . . . . ?
C033 O006 C013 O008 179.8(4) . . . . ?
C019 O006 C013 C034 177.8(5) . . . . ?
C033 O006 C013 C034 -2.3(7) . . . . ?
O009 O005 C015 C020 -0.5(8) . . . . ?
O009 O005 C015 C888 179.0(4) . . . . ?
C031 C012 C016 O009 1.3(7) . . . . ?
C027 C012 C016 O009 179.0(5) . . . . ?
O005 O009 C016 C012 178.9(4) . . . . ?
C011 O009 C016 C012 -0.8(8) . . . . ?
O008 O004 C017 C021 -0.6(7) . . . . ?
O008 O004 C017 C666 179.5(4) . . . . ?
O009 C011 C018 C031 -0.1(7) . . . . ?
CL03 C011 C018 C031 178.1(5) . . . . ?
O009 C011 C018 C022 -179.8(5) . . . . ?
CL03 C011 C018 C022 -1.6(8) . . . . ?
C013 O006 C019 C014 0.5(7) . . . . ?
C033 O006 C019 C014 -179.4(4) . . . . ?
C013 O006 C019 Cl01 -178.6(3) . . . . ?
C033 O006 C019 Cl01 1.5(7) . . . . ?
C023 C014 C019 O006 -0.8(7) . . . . ?
C032 C014 C019 O006 -179.4(5) . . . . ?
C023 C014 C019 Cl01 178.4(4) . . . . ?
C032 C014 C019 Cl01 -0.2(6) . . . . ?
O005 C015 C020 CL03 -1.5(8) . . . . ?
C888 C015 C020 CL03 179.1(5) . . . . ?
O005 C015 C020 C900 -178.1(5) . . . . ?
C888 C015 C020 C900 2.5(10) . . . . ?
C010 CL03 C020 C015 -175.8(5) . . . . ?
C011 CL03 C020 C015 3.6(8) . . . . ?
C010 CL03 C020 C900 1.0(9) . . . . ?
C011 CL03 C020 C900 -179.6(5) . . . . ?
O004 C017 C021 C034 -1.3(8) . . . . ?
C666 C017 C021 C034 178.6(5) . . . . ?
O004 C017 C021 C555 180.0(5) . . . . ?
C666 C017 C021 C555 -0.2(9) . . . . ?
C019 C014 C023 O008 0.6(7) . . . . ?
C032 C014 C023 O008 179.3(4) . . . . ?
O004 O008 C023 C014 179.4(4) . . . . ?
C013 O008 C023 C014 -0.2(7) . . . . ?
C011 C018 C031 C012 0.6(8) . . . . ?
C022 C018 C031 C012 -179.6(5) . . . . ?
C011 C018 C031 Cl02 -178.3(4) . . . . ?
C022 C018 C031 Cl02 1.4(8) . . . . ?
C016 C012 C031 C018 -1.2(8) . . . . ?
C027 C012 C031 C018 -178.9(6) . . . . ?
C016 C012 C031 Cl02 177.8(4) . . . . ?
C027 C012 C031 Cl02 0.1(7) . . . . ?
C017 C021 C034 O007 -176.3(5) . . . . ?
C555 C021 C034 O007 2.5(8) . . . . ?
C017 C021 C034 C013 3.5(7) . . . . ?
C555 C021 C034 C013 -177.7(5) . . . . ?
O008 C013 C034 O007 175.9(5) . . . . ?
O006 C013 C034 O007 -2.1(8) . . . . ?
O008 C013 C034 C021 -3.9(6) . . . . ?
O006 C013 C034 C021 178.1(4) . . . . ?
C021 C017 C666 C777 101.7(7) . . . . ?
O004 C017 C666 C777 -78.5(6) . . . . ?
C020 C015 C888 C999 100.6(7) . . . . ?
O005 C015 C888 C999 -78.8(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.667
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.975
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.039
_database_code_depnum_ccdc_archive 'CCDC 932483'
#######################################################################
#
#                 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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
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
_database_code_depnum_ccdc_archive 'CCDC 970761'
