# Electronic Supplementary Material (ESI) for Chemical Science
# This journal is © The Royal Society of Chemistry 2013

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#
#                 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:
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data_130515_zy_4_27_2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H17 Cl3 N2 O3'
_chemical_formula_sum            'C17 H17 Cl3 N2 O3'
_chemical_formula_weight         403.68

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'
Cl Cl 0.1484 0.1585 '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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   9.7614(10)
_cell_length_b                   10.2988(10)
_cell_length_c                   10.4722(11)
_cell_angle_alpha                80.745(8)
_cell_angle_beta                 71.023(9)
_cell_angle_gamma                89.009(8)
_cell_volume                     981.92(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1408
_cell_measurement_theta_min      3.3519
_cell_measurement_theta_max      29.5862

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.26
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             416
_exptl_absorpt_coefficient_mu    0.484
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8488
_exptl_absorpt_correction_T_max  0.8845
_exptl_absorpt_process_details   
;
CrysAlis PRO (Agilent Technologies, 2011) 
;

_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, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean 10.3592
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6121
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_sigmaI/netI    0.0505
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.36
_diffrn_reflns_theta_max         25.35
_reflns_number_total             3582
_reflns_number_gt                2407
_reflns_threshold_expression     >2sigma(I)

_computing_cell_refinement       'CrysAlis PRO (Agilent Technologies, 2011)'
_computing_data_collection       'CrysAlis PRO'
_computing_data_reduction        'CrysAlis PRO'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  OLEX2
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'

_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^)+(0.2000P)^2^+0.0000P] 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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3582
_refine_ls_number_parameters     238
_refine_ls_number_restraints     34
_refine_ls_R_factor_all          0.1546
_refine_ls_R_factor_gt           0.1187
_refine_ls_wR_factor_ref         0.4023
_refine_ls_wR_factor_gt          0.3593
_refine_ls_goodness_of_fit_ref   1.494
_refine_ls_restrained_S_all      1.515
_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
Cl1 Cl 1.3707(2) 0.6963(3) 0.2529(2) 0.0971(9) Uani 1 1 d . . .
Cl2 Cl 1.1327(4) 0.7974(4) 0.4455(3) 0.1401(14) Uani 1 1 d . . .
Cl3 Cl 1.0829(4) 0.6028(5) 0.3044(7) 0.207(2) Uani 1 1 d . . .
O1 O 0.4875(4) 0.8250(4) 0.5042(4) 0.0518(11) Uani 1 1 d . . .
O2 O 0.8158(5) 0.9840(4) -0.1143(4) 0.0649(13) Uani 1 1 d . . .
O3 O 0.6888(4) 0.7922(4) -0.0402(3) 0.0485(10) Uani 1 1 d . . .
N1 N 0.6857(5) 0.9572(4) 0.3902(4) 0.0440(11) Uani 1 1 d . . .
H1 H 0.6473 1.0207 0.4323 0.053 Uiso 1 1 calc R . .
N2 N 0.9010(12) 0.3077(8) 0.1407(10) 0.069(3) Uani 0.493(9) 1 d PDU A 1
C1 C 0.6556(6) 0.6078(5) 0.4276(5) 0.0444(13) Uani 1 1 d . . .
H1A H 0.6073 0.6008 0.5211 0.053 Uiso 1 1 calc R . .
C2 C 0.7018(6) 0.4965(5) 0.3746(6) 0.0505(15) Uani 1 1 d . . .
H2 H 0.6859 0.4146 0.4305 0.061 Uiso 1 1 calc R . .
C3 C 0.7742(6) 0.5086(5) 0.2335(5) 0.0459(13) Uani 1 1 d . A .
C4 C 0.7971(6) 0.6301(5) 0.1526(5) 0.0434(13) Uani 1 1 d . . .
H4 H 0.8465 0.6361 0.0594 0.052 Uiso 1 1 calc R . .
C5 C 0.7495(5) 0.7444(5) 0.2046(5) 0.0360(11) Uani 1 1 d . . .
C6 C 0.6784(5) 0.7325(5) 0.3463(5) 0.0364(11) Uani 1 1 d . . .
C7 C 0.6082(6) 0.8424(5) 0.4194(5) 0.0387(12) Uani 1 1 d . . .
C8 C 0.8326(6) 0.9788(5) 0.2897(5) 0.0427(13) Uani 1 1 d . . .
H8A H 0.8941 0.9091 0.3101 0.051 Uiso 1 1 calc R . .
H8B H 0.8742 1.0620 0.2946 0.051 Uiso 1 1 calc R . .
C9 C 0.8249(5) 0.9802(5) 0.1490(5) 0.0385(12) Uani 1 1 d . . .
H9 H 0.8506 1.0573 0.0853 0.046 Uiso 1 1 calc R . .
C10 C 0.7817(5) 0.8726(5) 0.1125(5) 0.0377(12) Uani 1 1 d . . .
C11 C 0.7665(6) 0.8905(5) -0.0281(5) 0.0421(13) Uani 1 1 d . . .
C12 C 0.6520(7) 0.7904(6) -0.1687(5) 0.0524(15) Uani 1 1 d . . .
C13 C 0.7871(8) 0.7961(8) -0.2868(6) 0.077(2) Uani 1 1 d . . .
H13A H 0.8583 0.7437 -0.2597 0.116 Uiso 1 1 calc R . .
H13B H 0.8232 0.8857 -0.3177 0.116 Uiso 1 1 calc R . .
H13C H 0.7673 0.7627 -0.3598 0.116 Uiso 1 1 calc R . .
C14 C 0.5729(10) 0.6540(9) -0.1329(8) 0.088(2) Uani 1 1 d . . .
H14A H 0.5026 0.6448 -0.0429 0.133 Uiso 1 1 calc R . .
H14B H 0.6421 0.5863 -0.1354 0.133 Uiso 1 1 calc R . .
H14C H 0.5249 0.6463 -0.1983 0.133 Uiso 1 1 calc R . .
C15 C 0.5537(9) 0.8988(9) -0.1843(8) 0.085(2) Uani 1 1 d . . .
H15A H 0.6086 0.9808 -0.2164 0.128 Uiso 1 1 calc R . .
H15B H 0.4811 0.9024 -0.0974 0.128 Uiso 1 1 calc R . .
H15C H 0.5078 0.8833 -0.2491 0.128 Uiso 1 1 calc R . .
C16 C 0.8285(7) 0.3931(6) 0.1747(6) 0.0641(18) Uani 1 1 d DU . .
C17 C 1.1891(8) 0.7367(8) 0.2893(7) 0.075(2) Uani 1 1 d . . .
H17 H 1.1791 0.8047 0.2162 0.090 Uiso 1 1 calc R . .
N2A N 0.740(2) 0.2898(15) 0.223(2) 0.069(3) Uani 0.244(9) 1 d PDU A 2
N2B N 0.837(2) 0.4012(16) 0.0457(15) 0.069(3) Uani 0.263(9) 1 d PDU A 3

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 0.0590(12) 0.1255(19) 0.1061(16) -0.0406(14) -0.0160(11) 0.0071(11)
Cl2 0.128(2) 0.192(3) 0.0882(16) -0.0323(17) -0.0187(15) 0.075(2)
Cl3 0.122(3) 0.166(4) 0.362(7) -0.055(4) -0.110(4) -0.035(3)
O1 0.047(2) 0.051(2) 0.047(2) -0.0146(16) 0.0030(18) 0.0018(17)
O2 0.088(3) 0.056(3) 0.048(2) 0.0098(19) -0.026(2) -0.019(2)
O3 0.064(2) 0.049(2) 0.0340(18) -0.0029(15) -0.0197(17) -0.0014(18)
N1 0.045(3) 0.046(3) 0.040(2) -0.0132(18) -0.0099(19) 0.004(2)
N2 0.078(5) 0.031(4) 0.063(4) -0.001(3) 0.022(4) 0.021(4)
C1 0.047(3) 0.049(3) 0.034(2) 0.001(2) -0.012(2) -0.002(2)
C2 0.055(3) 0.034(3) 0.052(3) 0.006(2) -0.011(3) 0.003(2)
C3 0.047(3) 0.034(3) 0.054(3) -0.007(2) -0.012(2) 0.004(2)
C4 0.043(3) 0.045(3) 0.037(2) -0.005(2) -0.007(2) 0.008(2)
C5 0.034(2) 0.037(3) 0.041(3) -0.005(2) -0.018(2) 0.000(2)
C6 0.033(2) 0.040(3) 0.036(2) -0.005(2) -0.011(2) 0.002(2)
C7 0.045(3) 0.041(3) 0.033(2) -0.006(2) -0.015(2) 0.001(2)
C8 0.041(3) 0.041(3) 0.049(3) -0.012(2) -0.017(2) -0.002(2)
C9 0.040(3) 0.032(3) 0.040(2) -0.007(2) -0.008(2) 0.001(2)
C10 0.036(3) 0.041(3) 0.034(2) -0.004(2) -0.009(2) 0.003(2)
C11 0.045(3) 0.040(3) 0.035(2) -0.001(2) -0.007(2) 0.000(2)
C12 0.064(4) 0.059(4) 0.043(3) -0.014(2) -0.026(3) 0.004(3)
C13 0.083(5) 0.104(6) 0.046(3) -0.022(3) -0.017(3) 0.010(4)
C14 0.112(7) 0.089(5) 0.081(5) -0.041(4) -0.042(5) -0.005(5)
C15 0.087(5) 0.105(6) 0.080(5) -0.012(4) -0.051(4) 0.022(5)
C16 0.075(4) 0.041(3) 0.058(3) -0.002(3) 0.000(3) 0.004(3)
C17 0.066(4) 0.079(5) 0.077(4) 0.008(4) -0.029(4) 0.004(4)
N2A 0.078(5) 0.031(4) 0.063(4) -0.001(3) 0.022(4) 0.021(4)
N2B 0.078(5) 0.031(4) 0.063(4) -0.001(3) 0.022(4) 0.021(4)

_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 C17 1.746(8) . ?
Cl2 C17 1.761(8) . ?
Cl3 C17 1.695(9) . ?
O1 C7 1.218(6) . ?
O2 C11 1.195(6) . ?
O3 C11 1.322(7) . ?
O3 C12 1.503(7) . ?
N1 C7 1.352(7) . ?
N1 C8 1.472(7) . ?
N1 H1 0.8600 . ?
N2 C16 1.148(9) . ?
C1 C2 1.360(8) . ?
C1 C6 1.400(7) . ?
C1 H1A 0.9300 . ?
C2 C3 1.401(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.371(7) . ?
C3 C16 1.441(8) . ?
C4 C5 1.385(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.405(7) . ?
C5 C10 1.476(7) . ?
C6 C7 1.499(7) . ?
C8 C9 1.498(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.346(7) . ?
C9 H9 0.9300 . ?
C10 C11 1.509(7) . ?
C12 C13 1.480(9) . ?
C12 C15 1.483(10) . ?
C12 C14 1.545(10) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 N2A 1.307(16) . ?
C16 N2B 1.314(16) . ?
C17 H17 0.9800 . ?

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
C11 O3 C12 121.4(4) . . ?
C7 N1 C8 123.2(4) . . ?
C7 N1 H1 118.4 . . ?
C8 N1 H1 118.4 . . ?
C2 C1 C6 122.3(4) . . ?
C2 C1 H1A 118.9 . . ?
C6 C1 H1A 118.9 . . ?
C1 C2 C3 118.2(5) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 H2 120.9 . . ?
C4 C3 C2 120.1(5) . . ?
C4 C3 C16 120.2(5) . . ?
C2 C3 C16 119.6(5) . . ?
C3 C4 C5 122.5(5) . . ?
C3 C4 H4 118.8 . . ?
C5 C4 H4 118.8 . . ?
C4 C5 C6 117.4(4) . . ?
C4 C5 C10 119.7(4) . . ?
C6 C5 C10 122.8(4) . . ?
C1 C6 C5 119.5(4) . . ?
C1 C6 C7 115.0(4) . . ?
C5 C6 C7 125.2(4) . . ?
O1 C7 N1 122.6(4) . . ?
O1 C7 C6 120.0(5) . . ?
N1 C7 C6 117.4(4) . . ?
N1 C8 C9 109.3(4) . . ?
N1 C8 H8A 109.8 . . ?
C9 C8 H8A 109.8 . . ?
N1 C8 H8B 109.8 . . ?
C9 C8 H8B 109.8 . . ?
H8A C8 H8B 108.3 . . ?
C10 C9 C8 121.5(4) . . ?
C10 C9 H9 119.3 . . ?
C8 C9 H9 119.3 . . ?
C9 C10 C5 122.3(4) . . ?
C9 C10 C11 116.1(4) . . ?
C5 C10 C11 121.7(4) . . ?
O2 C11 O3 125.4(5) . . ?
O2 C11 C10 123.4(5) . . ?
O3 C11 C10 111.1(4) . . ?
C13 C12 C15 113.6(6) . . ?
C13 C12 O3 109.6(5) . . ?
C15 C12 O3 109.2(5) . . ?
C13 C12 C14 111.6(5) . . ?
C15 C12 C14 111.8(7) . . ?
O3 C12 C14 100.1(5) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N2 C16 N2A 76.5(10) . . ?
N2 C16 N2B 77.2(10) . . ?
N2A C16 N2B 97.3(15) . . ?
N2 C16 C3 161.7(10) . . ?
N2A C16 C3 114.2(8) . . ?
N2B C16 C3 114.2(8) . . ?
Cl3 C17 Cl1 111.1(4) . . ?
Cl3 C17 Cl2 108.7(5) . . ?
Cl1 C17 Cl2 108.5(4) . . ?
Cl3 C17 H17 109.5 . . ?
Cl1 C17 H17 109.5 . . ?
Cl2 C17 H17 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         1.693
_refine_diff_density_min         -0.777
_refine_diff_density_rms         0.114
_database_code_depnum_ccdc_archive 'CCDC 940344'