# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2010

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#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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# 
#  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 
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#  except for the purpose of generating routine backup copies 
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#  data retrieval see:
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data_aaa
_database_code_depnum_ccdc_archive 'CCDC 786136'
#TrackingRef '1916_web_deposit_cif_file_0_CHOEUNJIN_1280280485.cif'


_audit_creation_method           SHELXTL
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H10 Cl3 Cu N3 O2'
_chemical_formula_weight         434.15

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/m

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   10.3495(7)
_cell_length_b                   13.5576(9)
_cell_length_c                   12.7601(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.5980(10)
_cell_angle_gamma                90.00
_cell_volume                     1664.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3561
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      28.28

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.732
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             868
_exptl_absorpt_coefficient_mu    1.806
_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      173(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7471
_diffrn_reflns_av_R_equivalents  0.0853
_diffrn_reflns_av_sigmaI/netI    0.0579
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.72
_diffrn_reflns_theta_max         28.28
_reflns_number_total             2055
_reflns_number_gt                1752
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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^)+(0.0356P)^2^+5.0687P] 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         2055
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0459
_refine_ls_wR_factor_ref         0.1060
_refine_ls_wR_factor_gt          0.1025
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_restrained_S_all      1.121
_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
Cu1 Cu 0.85542(5) 0.0000 0.34250(4) 0.01541(16) Uani 1 2 d S . .
Cl1 Cl 1.23994(13) 0.0000 0.04971(10) 0.0261(3) Uani 1 2 d S . .
Cl2 Cl 0.77727(13) 0.0000 0.48435(9) 0.0250(3) Uani 1 2 d S . .
Cl3 Cl 0.63965(11) 0.0000 0.16895(9) 0.0220(2) Uani 1 2 d S . .
O1W O 0.6497(3) 0.21021(17) 0.0485(2) 0.0328(6) Uani 1 1 d . . .
N1 N 0.8932(3) 0.14795(18) 0.3379(2) 0.0170(5) Uani 1 1 d . . .
N2 N 0.9765(4) 0.0000 0.2563(3) 0.0154(7) Uani 1 2 d S . .
C1 C 0.8474(3) 0.2210(2) 0.3863(3) 0.0204(6) Uani 1 1 d . . .
H1A H 0.7949 0.2048 0.4313 0.024 Uiso 1 1 calc R . .
C2 C 0.8742(3) 0.3196(2) 0.3727(3) 0.0241(7) Uani 1 1 d . . .
H2A H 0.8409 0.3697 0.4083 0.029 Uiso 1 1 calc R . .
C3 C 0.9493(4) 0.3441(2) 0.3072(3) 0.0248(7) Uani 1 1 d . . .
H3A H 0.9685 0.4112 0.2971 0.030 Uiso 1 1 calc R . .
C4 C 0.9966(3) 0.2692(2) 0.2561(3) 0.0203(6) Uani 1 1 d . . .
H4A H 1.0481 0.2843 0.2100 0.024 Uiso 1 1 calc R . .
C5 C 0.9675(3) 0.1721(2) 0.2734(2) 0.0159(6) Uani 1 1 d . . .
C6 C 1.0154(3) 0.0861(2) 0.2263(2) 0.0156(6) Uani 1 1 d . . .
C7 C 1.0973(3) 0.0897(2) 0.1613(2) 0.0183(6) Uani 1 1 d . . .
H7A H 1.1252 0.1507 0.1397 0.022 Uiso 1 1 calc R . .
C8 C 1.1368(5) 0.0000 0.1291(4) 0.0198(9) Uani 1 2 d S . .

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
Cu1 0.0219(3) 0.0127(3) 0.0158(3) 0.000 0.0119(2) 0.000
Cl1 0.0340(6) 0.0227(5) 0.0335(6) 0.000 0.0263(5) 0.000
Cl2 0.0379(7) 0.0233(5) 0.0221(5) 0.000 0.0207(5) 0.000
Cl3 0.0222(5) 0.0235(5) 0.0202(5) 0.000 0.0075(4) 0.000
O1W 0.0420(15) 0.0235(12) 0.0400(14) -0.0028(10) 0.0235(12) 0.0042(11)
N1 0.0188(13) 0.0163(11) 0.0171(12) -0.0020(9) 0.0080(10) 0.0002(10)
N2 0.0154(17) 0.0141(16) 0.0190(17) 0.000 0.0093(14) 0.000
C1 0.0226(15) 0.0220(15) 0.0182(14) -0.0034(11) 0.0095(12) 0.0031(13)
C2 0.0279(18) 0.0193(15) 0.0244(16) -0.0053(12) 0.0086(13) 0.0042(13)
C3 0.0312(19) 0.0136(14) 0.0272(17) -0.0009(12) 0.0080(14) 0.0012(12)
C4 0.0240(16) 0.0157(14) 0.0226(15) 0.0011(11) 0.0102(13) 0.0006(12)
C5 0.0160(14) 0.0169(14) 0.0147(13) -0.0029(10) 0.0054(11) -0.0005(11)
C6 0.0183(14) 0.0131(13) 0.0152(13) -0.0013(10) 0.0059(11) -0.0006(11)
C7 0.0236(16) 0.0129(13) 0.0201(15) 0.0020(11) 0.0102(12) -0.0015(11)
C8 0.019(2) 0.024(2) 0.019(2) 0.000 0.0105(17) 0.000

_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
Cu1 N2 1.948(3) . ?
Cu1 N1 2.049(2) . ?
Cu1 N1 2.049(2) 6 ?
Cu1 Cl2 2.2379(11) . ?
Cu1 Cl3 2.5001(12) . ?
Cl1 C8 1.722(4) . ?
N1 C1 1.343(4) . ?
N1 C5 1.356(4) . ?
N2 C6 1.336(3) 6 ?
N2 C6 1.336(3) . ?
C1 C2 1.388(4) . ?
C2 C3 1.375(5) . ?
C3 C4 1.390(4) . ?
C4 C5 1.386(4) . ?
C5 C6 1.478(4) . ?
C6 C7 1.388(4) . ?
C7 C8 1.392(3) . ?
C8 C7 1.392(3) 6 ?

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
N2 Cu1 N1 79.31(7) . . ?
N2 Cu1 N1 79.31(7) . 6 ?
N1 Cu1 N1 156.54(14) . 6 ?
N2 Cu1 Cl2 162.91(11) . . ?
N1 Cu1 Cl2 98.79(7) . . ?
N1 Cu1 Cl2 98.79(7) 6 . ?
N2 Cu1 Cl3 92.88(11) . . ?
N1 Cu1 Cl3 95.31(7) . . ?
N1 Cu1 Cl3 95.31(7) 6 . ?
Cl2 Cu1 Cl3 104.21(4) . . ?
C1 N1 C5 118.4(3) . . ?
C1 N1 Cu1 127.3(2) . . ?
C5 N1 Cu1 114.25(18) . . ?
C6 N2 C6 121.8(4) 6 . ?
C6 N2 Cu1 119.07(18) 6 . ?
C6 N2 Cu1 119.07(18) . . ?
N1 C1 C2 122.2(3) . . ?
C3 C2 C1 119.5(3) . . ?
C2 C3 C4 119.0(3) . . ?
C5 C4 C3 118.9(3) . . ?
N1 C5 C4 122.1(3) . . ?
N1 C5 C6 113.9(2) . . ?
C4 C5 C6 123.9(3) . . ?
N2 C6 C7 121.1(3) . . ?
N2 C6 C5 113.0(3) . . ?
C7 C6 C5 125.9(3) . . ?
C6 C7 C8 117.1(3) . . ?
C7 C8 C7 121.7(4) . 6 ?
C7 C8 Cl1 119.12(19) . . ?
C7 C8 Cl1 119.12(19) 6 . ?

_diffrn_measured_fraction_theta_max 0.952
_diffrn_reflns_theta_full        28.28
_diffrn_measured_fraction_theta_full 0.952
_refine_diff_density_max         0.796
_refine_diff_density_min         -0.753
_refine_diff_density_rms         0.117