# Electronic Supplementary Material (ESI) for ChemComm.
# 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
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# 
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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_zheng

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H13 Cl2 N O3'
_chemical_formula_weight         362.19

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

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

_cell_length_a                   7.4219(15)
_cell_length_b                   9.3714(19)
_cell_length_c                   13.520(3)
_cell_angle_alpha                109.06(3)
_cell_angle_beta                 94.10(3)
_cell_angle_gamma                108.60(3)
_cell_volume                     826.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             372
_exptl_absorpt_coefficient_mu    0.409
_exptl_absorpt_correction_type   ?
_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8068
_diffrn_reflns_av_R_equivalents  0.0204
_diffrn_reflns_av_sigmaI/netI    0.0264
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.08
_diffrn_reflns_theta_max         27.48
_reflns_number_total             3763
_reflns_number_gt                3249
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_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)+(0.0691P)²+0.0948P] 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     SHELXL
_refine_ls_extinction_coef       0.040(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3763
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0378
_refine_ls_wR_factor_ref         0.1210
_refine_ls_wR_factor_gt          0.1150
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_restrained_S_all      1.122
_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 0.23649(7) -0.30034(6) 0.04073(3) 0.06980(18) Uani 1 1 d . . .
Cl2 Cl -0.27149(7) 0.00321(6) 0.11284(4) 0.06923(18) Uani 1 1 d . . .
O2 O 0.13543(17) -0.29579(12) 0.37915(8) 0.0527(3) Uani 1 1 d . . .
C7 C 0.2129(2) 0.04169(16) 0.42265(10) 0.0389(3) Uani 1 1 d . . .
C4 C -0.0087(2) 0.02313(16) 0.26942(10) 0.0411(3) Uani 1 1 d . . .
H4A H -0.0589 0.0911 0.3160 0.049 Uiso 1 1 calc R . .
C9 C 0.32344(19) 0.22399(17) 0.58257(10) 0.0385(3) Uani 1 1 d . . .
C10 C 0.38826(19) 0.38621(16) 0.66472(10) 0.0385(3) Uani 1 1 d . . .
C15 C 0.4045(2) 0.52206(18) 0.63987(11) 0.0438(3) Uani 1 1 d . . .
H15A H 0.3680 0.5104 0.5696 0.053 Uiso 1 1 calc R . .
C5 C 0.1400(2) -0.01703(16) 0.30737(10) 0.0394(3) Uani 1 1 d . . .
C16 C 0.2239(2) -0.19505(18) 0.47709(11) 0.0444(3) Uani 1 1 d . . .
C3 C -0.0801(2) -0.04040(18) 0.16071(11) 0.0453(3) Uani 1 1 d . . .
C2 C -0.0077(2) -0.14034(18) 0.08912(11) 0.0497(4) Uani 1 1 d . . .
H2A H -0.0585 -0.1828 0.0163 0.060 Uiso 1 1 calc R . .
C11 C 0.4405(2) 0.4054(2) 0.77084(11) 0.0478(3) Uani 1 1 d . . .
H11A H 0.4279 0.3153 0.7887 0.057 Uiso 1 1 calc R . .
C8 C 0.25437(19) -0.02528(16) 0.49215(10) 0.0395(3) Uani 1 1 d . . .
C6 C 0.2190(2) -0.11431(18) 0.23707(11) 0.0447(3) Uani 1 1 d . . .
H6A H 0.3216 -0.1379 0.2624 0.054 Uiso 1 1 calc R . .
C1 C 0.1430(2) -0.17534(18) 0.12937(11) 0.0474(3) Uani 1 1 d . . .
O1 O 0.2715(3) -0.23512(17) 0.54608(11) 0.0867(5) Uani 1 1 d . . .
C12 C 0.5109(3) 0.5585(2) 0.84917(12) 0.0560(4) Uani 1 1 d . . .
H12A H 0.5468 0.5712 0.9198 0.067 Uiso 1 1 calc R . .
C17 C 0.0972(2) -0.46689(18) 0.35360(14) 0.0530(4) Uani 1 1 d . . .
H17A H 0.0011 -0.5102 0.3916 0.064 Uiso 1 1 calc R . .
H17B H 0.2150 -0.4833 0.3737 0.064 Uiso 1 1 calc R . .
C13 C 0.5285(2) 0.6927(2) 0.82383(13) 0.0560(4) Uani 1 1 d . . .
H13A H 0.5766 0.7955 0.8771 0.067 Uiso 1 1 calc R . .
C14 C 0.4748(2) 0.67445(19) 0.71955(13) 0.0512(4) Uani 1 1 d . . .
H14A H 0.4858 0.7650 0.7026 0.061 Uiso 1 1 calc R . .
C18 C 0.0240(3) -0.5488(2) 0.23623(16) 0.0669(5) Uani 1 1 d . . .
H18A H -0.0036 -0.6629 0.2159 0.100 Uiso 1 1 calc R . .
H18B H 0.1207 -0.5050 0.1997 0.100 Uiso 1 1 calc R . .
H18C H -0.0921 -0.5313 0.2174 0.100 Uiso 1 1 calc R . .
O3 O 0.25466(14) 0.20289(11) 0.48034(7) 0.0405(2) Uani 1 1 d . . .
N1 N 0.32676(17) 0.09334(14) 0.59377(9) 0.0414(3) Uani 1 1 d . . .


_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 C1 1.7354(16) . ?
Cl2 C3 1.7365(16) . ?
O2 C16 1.3188(19) . ?
O2 C17 1.4508(18) . ?
C7 C8 1.3560(19) . ?
C7 O3 1.3725(17) . ?
C7 C5 1.4676(18) . ?
C4 C3 1.3825(19) . ?
C4 C5 1.390(2) . ?
C4 H4A 0.9300 . ?
C9 N1 1.2893(18) . ?
C9 O3 1.3660(15) . ?
C9 C10 1.460(2) . ?
C10 C15 1.391(2) . ?
C10 C11 1.3959(19) . ?
C15 C14 1.383(2) . ?
C15 H15A 0.9300 . ?
C5 C6 1.390(2) . ?
C16 O1 1.1844(19) . ?
C16 C8 1.475(2) . ?
C3 C2 1.380(2) . ?
C2 C1 1.385(2) . ?
C2 H2A 0.9300 . ?
C11 C12 1.379(2) . ?
C11 H11A 0.9300 . ?
C8 N1 1.3884(18) . ?
C6 C1 1.378(2) . ?
C6 H6A 0.9300 . ?
C12 C13 1.379(3) . ?
C12 H12A 0.9300 . ?
C17 C18 1.489(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C13 C14 1.376(2) . ?
C13 H13A 0.9300 . ?
C14 H14A 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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
C16 O2 C17 117.84(12) . . ?
C8 C7 O3 107.12(11) . . ?
C8 C7 C5 135.51(13) . . ?
O3 C7 C5 117.37(12) . . ?
C3 C4 C5 118.41(13) . . ?
C3 C4 H4A 120.8 . . ?
C5 C4 H4A 120.8 . . ?
N1 C9 O3 113.86(12) . . ?
N1 C9 C10 127.43(12) . . ?
O3 C9 C10 118.69(12) . . ?
C15 C10 C11 119.30(13) . . ?
C15 C10 C9 121.92(12) . . ?
C11 C10 C9 118.76(13) . . ?
C14 C15 C10 120.09(14) . . ?
C14 C15 H15A 120.0 . . ?
C10 C15 H15A 120.0 . . ?
C6 C5 C4 120.57(12) . . ?
C6 C5 C7 119.54(12) . . ?
C4 C5 C7 119.89(12) . . ?
O1 C16 O2 124.39(15) . . ?
O1 C16 C8 123.32(14) . . ?
O2 C16 C8 112.28(12) . . ?
C2 C3 C4 122.35(14) . . ?
C2 C3 Cl2 118.83(11) . . ?
C4 C3 Cl2 118.80(12) . . ?
C3 C2 C1 117.77(13) . . ?
C3 C2 H2A 121.1 . . ?
C1 C2 H2A 121.1 . . ?
C12 C11 C10 119.75(15) . . ?
C12 C11 H11A 120.1 . . ?
C10 C11 H11A 120.1 . . ?
C7 C8 N1 109.59(12) . . ?
C7 C8 C16 131.08(13) . . ?
N1 C8 C16 119.21(12) . . ?
C1 C6 C5 119.02(14) . . ?
C1 C6 H6A 120.5 . . ?
C5 C6 H6A 120.5 . . ?
C6 C1 C2 121.84(14) . . ?
C6 C1 Cl1 119.63(12) . . ?
C2 C1 Cl1 118.53(11) . . ?
C13 C12 C11 120.64(15) . . ?
C13 C12 H12A 119.7 . . ?
C11 C12 H12A 119.7 . . ?
O2 C17 C18 106.76(14) . . ?
O2 C17 H17A 110.4 . . ?
C18 C17 H17A 110.4 . . ?
O2 C17 H17B 110.4 . . ?
C18 C17 H17B 110.4 . . ?
H17A C17 H17B 108.6 . . ?
C14 C13 C12 119.90(15) . . ?
C14 C13 H13A 120.0 . . ?
C12 C13 H13A 120.0 . . ?
C13 C14 C15 120.31(16) . . ?
C13 C14 H14A 119.8 . . ?
C15 C14 H14A 119.8 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C9 O3 C7 104.77(11) . . ?
C9 N1 C8 104.65(11) . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.052
_database_code_depnum_ccdc_archive 'CCDC 982238'
