# Electronic Supplementary Material (ESI) for Chemical Science.
# 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.
#
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#  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
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  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.
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data_kliu_45_0m
_audit_creation_date             2013-10-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C12 H11 Cl O2'
_chemical_formula_sum            'C12 H11 Cl O2'
_chemical_formula_weight         222.66
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   19.3677(7)
_cell_length_b                   4.6908(2)
_cell_length_c                   11.3487(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.521(2)
_cell_angle_gamma                90.00
_cell_volume                     1026.25(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4614
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      65.120
_cell_measurement_theta_min      4.588
_exptl_absorpt_coefficient_mu    3.092
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_correction_T_min  0.6391
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0439 before and 0.0303 after correction.
The Ratio of minimum to maximum transmission is 0.8492.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.214
_exptl_crystal_size_mid          0.061
_exptl_crystal_size_min          0.058
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6419
_diffrn_reflns_theta_full        65.12
_diffrn_reflns_theta_max         65.12
_diffrn_reflns_theta_min         4.59
_diffrn_ambient_temperature      99.97
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_number_gt                1613
_reflns_number_total             1738
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1738
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0296
_refine_ls_R_factor_gt           0.0267
_refine_ls_restrained_S_all      1.084
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0324P)²+0.4676P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0644
_refine_ls_wR_factor_ref         0.0660
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7), C8(H8), C11(H11)
2.d X=CH2 refined with riding coordinates:
 C12(H12A,H12B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.047150(16) 0.42297(7) 0.17792(3) 0.01642(12) Uani 1 1 d . . .
O1 O 0.22398(5) -0.4406(2) -0.01564(9) 0.0179(2) Uani 1 1 d . . .
O2 O 0.31481(5) -0.7195(2) -0.00985(9) 0.0230(3) Uani 1 1 d . . .
C1 C 0.28788(7) -0.5205(3) 0.03430(13) 0.0171(3) Uani 1 1 d . . .
C2 C 0.31963(7) -0.3426(3) 0.13634(12) 0.0176(3) Uani 1 1 d . . .
H2 H 0.3372 -0.1635 0.1018 0.021 Uiso 1 1 calc R . .
C3 C 0.26511(7) -0.2546(3) 0.21881(12) 0.0165(3) Uani 1 1 d . . .
H3A H 0.2511 -0.4232 0.2633 0.020 Uiso 1 1 calc R . .
H3B H 0.2853 -0.1123 0.2767 0.020 Uiso 1 1 calc R . .
C4 C 0.20258(7) -0.1296(3) 0.14832(12) 0.0144(3) Uani 1 1 d . . .
C5 C 0.15931(7) 0.0744(3) 0.19217(12) 0.0144(3) Uani 1 1 d . . .
H5 H 0.1686 0.1433 0.2708 0.017 Uiso 1 1 calc R . .
C6 C 0.10273(7) 0.1761(3) 0.12054(12) 0.0147(3) Uani 1 1 d . . .
C7 C 0.08833(7) 0.0860(3) 0.00463(12) 0.0167(3) Uani 1 1 d . . .
H7 H 0.0500 0.1623 -0.0438 0.020 Uiso 1 1 calc R . .
C8 C 0.13077(7) -0.1173(3) -0.03922(12) 0.0171(3) Uani 1 1 d . . .
H8 H 0.1218 -0.1835 -0.1183 0.020 Uiso 1 1 calc R . .
C9 C 0.18635(7) -0.2232(3) 0.03307(12) 0.0154(3) Uani 1 1 d . . .
C10 C 0.38243(8) -0.4931(3) 0.20178(14) 0.0206(3) Uani 1 1 d . . .
H10A H 0.3661 -0.6532 0.2487 0.025 Uiso 1 1 calc R . .
H10B H 0.4118 -0.5733 0.1431 0.025 Uiso 1 1 calc R . .
C11 C 0.42502(7) -0.2949(4) 0.28242(15) 0.0237(3) Uani 1 1 d . . .
H11 H 0.4452 -0.1350 0.2476 0.028 Uiso 1 1 calc R . .
C12 C 0.43664(8) -0.3250(4) 0.39771(15) 0.0302(4) Uani 1 1 d . . .
H12A H 0.4173 -0.4822 0.4359 0.036 Uiso 1 1 calc R . .
H12B H 0.4644 -0.1895 0.4429 0.036 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
Cl1 0.01558(18) 0.0167(2) 0.0169(2) -0.00049(13) 0.00133(12) 0.00310(13)
O1 0.0204(5) 0.0181(5) 0.0152(5) -0.0023(4) 0.0015(4) 0.0039(4)
O2 0.0271(6) 0.0195(6) 0.0233(5) -0.0005(5) 0.0067(4) 0.0065(5)
C1 0.0200(7) 0.0155(7) 0.0166(7) 0.0053(6) 0.0062(6) 0.0014(6)
C2 0.0178(7) 0.0163(7) 0.0189(7) 0.0022(6) 0.0033(6) 0.0020(6)
C3 0.0166(7) 0.0172(7) 0.0154(7) 0.0014(6) 0.0011(6) 0.0012(6)
C4 0.0152(7) 0.0139(7) 0.0144(7) 0.0023(6) 0.0024(5) -0.0026(5)
C5 0.0157(7) 0.0149(7) 0.0128(7) 0.0000(6) 0.0015(5) -0.0036(6)
C6 0.0143(6) 0.0135(7) 0.0170(7) 0.0015(6) 0.0041(5) -0.0005(6)
C7 0.0163(7) 0.0173(7) 0.0160(7) 0.0033(6) -0.0011(5) -0.0007(6)
C8 0.0201(7) 0.0191(7) 0.0118(7) -0.0007(6) 0.0005(5) -0.0019(6)
C9 0.0178(7) 0.0133(7) 0.0158(7) 0.0008(6) 0.0048(5) -0.0012(6)
C10 0.0181(7) 0.0195(8) 0.0244(8) 0.0027(6) 0.0033(6) 0.0048(6)
C11 0.0132(7) 0.0218(8) 0.0361(9) 0.0039(7) 0.0022(6) 0.0018(6)
C12 0.0199(8) 0.0362(10) 0.0344(10) -0.0070(8) 0.0018(7) -0.0031(7)

_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
Cl1 C6 1.7488(14) . ?
O1 C1 1.3633(18) . ?
O1 C9 1.3979(17) . ?
O2 C1 1.2019(18) . ?
C1 C2 1.510(2) . ?
C2 C3 1.5334(19) . ?
C2 C10 1.535(2) . ?
C3 C4 1.5048(19) . ?
C4 C5 1.395(2) . ?
C4 C9 1.387(2) . ?
C5 C6 1.385(2) . ?
C6 C7 1.384(2) . ?
C7 C8 1.383(2) . ?
C8 C9 1.382(2) . ?
C10 C11 1.496(2) . ?
C11 C12 1.314(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
C1 O1 C9 121.55(11) . . ?
O1 C1 C2 116.96(12) . . ?
O2 C1 O1 116.95(13) . . ?
O2 C1 C2 126.03(13) . . ?
C1 C2 C3 111.31(12) . . ?
C1 C2 C10 111.23(12) . . ?
C3 C2 C10 112.87(12) . . ?
C4 C3 C2 110.29(11) . . ?
C5 C4 C3 123.93(13) . . ?
C9 C4 C3 118.40(12) . . ?
C9 C4 C5 117.67(13) . . ?
C6 C5 C4 119.71(13) . . ?
C5 C6 Cl1 119.35(11) . . ?
C7 C6 Cl1 118.76(11) . . ?
C7 C6 C5 121.88(13) . . ?
C8 C7 C6 118.71(13) . . ?
C9 C8 C7 119.38(13) . . ?
C4 C9 O1 121.64(12) . . ?
C8 C9 O1 115.69(12) . . ?
C8 C9 C4 122.62(13) . . ?
C11 C10 C2 112.02(13) . . ?
C12 C11 C10 125.06(16) . . ?

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
Cl1 C6 C7 C8 -177.55(11) . . . . ?
O1 C1 C2 C3 40.03(17) . . . . ?
O1 C1 C2 C10 166.83(12) . . . . ?
O2 C1 C2 C3 -142.98(14) . . . . ?
O2 C1 C2 C10 -16.2(2) . . . . ?
C1 O1 C9 C4 -17.03(19) . . . . ?
C1 O1 C9 C8 165.43(12) . . . . ?
C1 C2 C3 C4 -49.64(16) . . . . ?
C1 C2 C10 C11 165.68(12) . . . . ?
C2 C3 C4 C5 -151.11(13) . . . . ?
C2 C3 C4 C9 29.39(18) . . . . ?
C2 C10 C11 C12 118.98(17) . . . . ?
C3 C2 C10 C11 -68.38(17) . . . . ?
C3 C4 C5 C6 -179.76(13) . . . . ?
C3 C4 C9 O1 3.9(2) . . . . ?
C3 C4 C9 C8 -178.78(13) . . . . ?
C4 C5 C6 Cl1 177.87(10) . . . . ?
C4 C5 C6 C7 -1.5(2) . . . . ?
C5 C4 C9 O1 -175.68(12) . . . . ?
C5 C4 C9 C8 1.7(2) . . . . ?
C5 C6 C7 C8 1.8(2) . . . . ?
C6 C7 C8 C9 -0.4(2) . . . . ?
C7 C8 C9 O1 176.14(12) . . . . ?
C7 C8 C9 C4 -1.4(2) . . . . ?
C9 O1 C1 O2 176.08(12) . . . . ?
C9 O1 C1 C2 -6.65(18) . . . . ?
C9 C4 C5 C6 -0.3(2) . . . . ?
C10 C2 C3 C4 -175.55(12) . . . . ?

_database_code_depnum_ccdc_archive 'CCDC 969294'
