# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A
# This journal is © The Royal Society of Chemistry 2012


#######################################################################
#
#                 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_d
_database_code_depnum_ccdc_archive 'CCDC 896825'
#TrackingRef 'web_deposit_cif_file_0_YabingHe_1345179419.utsa-40.CIF'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H7 Cl Cu N0 O6'
_chemical_formula_weight         418.23

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'
N N 0.0311 0.0180 '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'
Cu Cu -1.9646 0.5888 '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'

_symmetry_cell_setting           Trigonal
_symmetry_space_group_name_H-M   R32

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'y, x, -z'
'x-y, -y, -z'
'-x, -x+y, -z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'y+2/3, x+1/3, -z+1/3'
'x-y+2/3, -y+1/3, -z+1/3'
'-x+2/3, -x+y+1/3, -z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'y+1/3, x+2/3, -z+2/3'
'x-y+1/3, -y+2/3, -z+2/3'
'-x+1/3, -x+y+2/3, -z+2/3'

_cell_length_a                   18.5676(7)
_cell_length_b                   18.5676(7)
_cell_length_c                   52.205(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     15586.8(12)
_cell_formula_units_Z            18
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    0.802
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3762
_exptl_absorpt_coefficient_mu    1.750
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.5329
_exptl_absorpt_correction_T_max  0.7786
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean 10.3592
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10908
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_sigmaI/netI    0.0820
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -54
_diffrn_reflns_limit_l_max       61
_diffrn_reflns_theta_min         4.36
_diffrn_reflns_theta_max         67.51
_reflns_number_total             5973
_reflns_number_gt                3218
_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 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.
;
# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.065 -0.032 0.000 9693 2279 ' '
_platon_squeeze_details          
;
;


_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^)+(0.0815P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.12(10)
_refine_ls_number_reflns         5973
_refine_ls_number_parameters     186
_refine_ls_number_restraints     72
_refine_ls_R_factor_all          0.0962
_refine_ls_R_factor_gt           0.0715
_refine_ls_wR_factor_ref         0.2237
_refine_ls_wR_factor_gt          0.1895
_refine_ls_goodness_of_fit_ref   0.975
_refine_ls_restrained_S_all      0.998
_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 0.47580(11) -0.47649(12) 0.020736(10) 0.0919(3) Uani 1 1 d . . .
O1 O 0.4442(6) -0.9702(4) 0.03348(11) 0.130(3) Uani 1 1 d . . .
O2 O 0.4830(5) -0.8886(5) -0.00178(10) 0.117(2) Uani 1 1 d . . .
O3 O 0.4826(5) -0.6291(4) -0.00154(10) 0.1037(18) Uani 1 1 d . . .
O4 O 0.4405(4) -0.5901(4) 0.03280(10) 0.1040(18) Uani 1 1 d . . .
O5 O 0.4415(8) -0.4351(7) 0.05460(9) 0.174(3) Uani 1 1 d . . .
C1 C 0.4531(7) -0.9107(5) 0.02069(15) 0.099(3) Uani 1 1 d . . .
C2 C 0.4299(8) -0.8508(7) 0.03331(16) 0.114(3) Uani 1 1 d . . .
C3 C 0.4445(3) -0.7772(7) 0.02014(9) 0.1014(14) Uani 1 1 d . . .
H3A H 0.4617 -0.7694 0.0031 0.122 Uiso 1 1 calc R . .
C4 C 0.4339(6) -0.7194(6) 0.03198(17) 0.104(3) Uani 1 1 d . . .
C5 C 0.4559(8) -0.6415(7) 0.01935(15) 0.102(3) Uani 1 1 d . . .
C6 C 0.4042(8) -0.7356(8) 0.05909(18) 0.139(4) Uani 1 1 d . . .
H6A H 0.3940 -0.6974 0.0675 0.167 Uiso 1 1 calc R . .
C7 C 0.3917(5) -0.8050(8) 0.07183(11) 0.131(2) Uani 1 1 d . . .
C8 C 0.4027(6) -0.8641(5) 0.05812(17) 0.105(3) Uani 1 1 d . . .
H8A H 0.3911 -0.9134 0.0661 0.127 Uiso 1 1 calc R . .
C11 C 0.3651(5) -0.8243(6) 0.09914(8) 0.161(4) Uani 1 1 d GU . .
C12 C 0.4209(5) -0.8286(6) 0.11592(10) 0.199(5) Uani 1 1 d GU . .
H12A H 0.4678 -0.8286 0.1096 0.239 Uiso 1 1 calc R . .
C13 C 0.4068(5) -0.8329(6) 0.14217(9) 0.227(6) Uani 1 1 d GU . .
C14 C 0.3369(5) -0.8329(5) 0.15164(8) 0.196(4) Uani 1 1 d GU . .
C15 C 0.2810(4) -0.8287(4) 0.13486(12) 0.297(9) Uiso 1 1 d GU . .
C16 C 0.2951(4) -0.8244(5) 0.10861(11) 0.227(5) Uani 1 1 d GU . .
C17 C 0.2392(6) -0.8201(8) 0.09182(16) 0.380(13) Uiso 1 1 d GU . .
H17A H 0.2486 -0.8172 0.0743 0.456 Uiso 1 1 calc R . .
C18 C 0.1692(6) -0.8202(9) 0.1013(2) 0.51(2) Uiso 1 1 d GU . .
C19 C 0.1551(6) -0.8244(9) 0.1275(2) 0.438(16) Uiso 1 1 d GU . .
H19A H 0.1083 -0.8245 0.1339 0.526 Uiso 1 1 calc R . .
C20 C 0.2110(5) -0.8287(7) 0.14432(18) 0.356(9) Uani 1 1 d GU . .
H20A H 0.2015 -0.8316 0.1619 0.427 Uiso 1 1 calc R . .
Cl1 Cl 0.0688(13) -0.8429(12) 0.0834(2) 0.736(14) Uani 1 1 d U . .
O6 O 0.4505(8) -0.8615(8) 0.1601(2) 0.239(4) Uiso 1 1 d U . .

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 0.1240(9) 0.1245(9) 0.0619(4) -0.0021(7) 0.0042(7) 0.0881(5)
O1 0.217(8) 0.108(5) 0.081(3) 0.006(3) 0.035(4) 0.093(5)
O2 0.177(7) 0.101(5) 0.071(3) 0.008(3) 0.019(4) 0.068(5)
O3 0.144(6) 0.112(5) 0.081(4) 0.011(3) 0.014(4) 0.083(4)
O4 0.130(4) 0.132(5) 0.086(3) 0.005(3) 0.000(3) 0.092(4)
O5 0.271(11) 0.184(6) 0.108(3) -0.008(6) 0.062(7) 0.145(5)
C1 0.141(8) 0.060(4) 0.084(5) -0.008(4) -0.004(5) 0.042(4)
C2 0.168(10) 0.099(6) 0.075(5) -0.006(5) -0.021(5) 0.069(6)
C3 0.121(4) 0.120(7) 0.082(3) 0.001(6) 0.003(2) 0.074(7)
C4 0.116(6) 0.123(7) 0.086(5) 0.021(5) 0.030(5) 0.069(6)
C5 0.153(9) 0.117(7) 0.075(5) 0.006(4) 0.005(5) 0.096(7)
C6 0.200(13) 0.158(9) 0.084(6) -0.002(6) 0.032(7) 0.108(9)
C7 0.190(7) 0.151(9) 0.088(3) 0.043(7) 0.044(4) 0.113(9)
C8 0.147(8) 0.077(5) 0.099(6) 0.003(4) 0.034(5) 0.061(5)
C11 0.299(10) 0.211(9) 0.090(3) 0.022(6) 0.049(5) 0.215(9)
C12 0.326(13) 0.283(12) 0.089(4) 0.009(6) 0.049(6) 0.227(12)
C13 0.333(14) 0.331(15) 0.101(4) 0.053(7) 0.079(7) 0.230(13)
C14 0.310(11) 0.207(10) 0.141(5) 0.116(8) 0.127(6) 0.180(11)
C16 0.339(11) 0.345(14) 0.128(5) 0.101(7) 0.126(7) 0.269(11)
C20 0.400(15) 0.49(2) 0.356(16) 0.248(14) 0.286(13) 0.352(15)
Cl1 0.88(3) 0.96(3) 0.561(14) 0.285(19) -0.130(19) 0.60(3)

_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 O1 1.933(7) 3_755 ?
Cu1 O2 1.968(7) 6_665 ?
Cu1 O4 1.974(6) . ?
Cu1 O3 1.974(6) 4_645 ?
Cu1 O5 2.147(4) . ?
Cu1 Cu1 2.6534(10) 4_645 ?
O1 C1 1.230(10) . ?
O1 Cu1 1.933(7) 2_535 ?
O2 C1 1.275(10) . ?
O2 Cu1 1.968(7) 6_655 ?
O3 C5 1.172(9) . ?
O3 Cu1 1.974(6) 4_645 ?
O4 C5 1.324(11) . ?
C1 C2 1.528(13) . ?
C2 C8 1.367(13) . ?
C2 C3 1.429(15) . ?
C3 C4 1.334(14) . ?
C3 H3A 0.9300 . ?
C4 C5 1.452(13) . ?
C4 C6 1.494(13) . ?
C6 C7 1.363(16) . ?
C6 H6A 0.9300 . ?
C7 C8 1.407(14) . ?
C7 C11 1.492(7) . ?
C8 H8A 0.9300 . ?
C11 C12 1.3900 . ?
C11 C16 1.3900 . ?
C12 C13 1.3900 . ?
C12 H12A 0.9300 . ?
C13 C14 1.3900 . ?
C13 O6 1.498(13) . ?
C14 C15 1.3900 . ?
C14 C14 1.573(8) 12 ?
C15 C16 1.3900 . ?
C15 C20 1.3900 . ?
C16 C17 1.3900 . ?
C17 C18 1.3900 . ?
C17 H17A 0.9300 . ?
C18 C19 1.3900 . ?
C18 Cl1 1.932(17) . ?
C19 C20 1.3900 . ?
C19 H19A 0.9300 . ?
C20 H20A 0.9300 . ?

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
O1 Cu1 O2 92.2(4) 3_755 6_665 ?
O1 Cu1 O4 87.5(2) 3_755 . ?
O2 Cu1 O4 167.5(2) 6_665 . ?
O1 Cu1 O3 168.2(3) 3_755 4_645 ?
O2 Cu1 O3 86.93(17) 6_665 4_645 ?
O4 Cu1 O3 90.8(3) . 4_645 ?
O1 Cu1 O5 93.5(4) 3_755 . ?
O2 Cu1 O5 95.6(3) 6_665 . ?
O4 Cu1 O5 96.9(3) . . ?
O3 Cu1 O5 98.3(4) 4_645 . ?
O1 Cu1 Cu1 84.72(18) 3_755 4_645 ?
O2 Cu1 Cu1 83.73(17) 6_665 4_645 ?
O4 Cu1 Cu1 83.76(16) . 4_645 ?
O3 Cu1 Cu1 83.53(17) 4_645 4_645 ?
O5 Cu1 Cu1 178.1(4) . 4_645 ?
C1 O1 Cu1 122.0(6) . 2_535 ?
C1 O2 Cu1 120.5(7) . 6_655 ?
C5 O3 Cu1 125.5(7) . 4_645 ?
C5 O4 Cu1 121.6(6) . . ?
O1 C1 O2 129.1(10) . . ?
O1 C1 C2 117.4(8) . . ?
O2 C1 C2 113.5(9) . . ?
C8 C2 C3 120.3(8) . . ?
C8 C2 C1 119.4(8) . . ?
C3 C2 C1 120.0(8) . . ?
C4 C3 C2 120.7(5) . . ?
C4 C3 H3A 119.6 . . ?
C2 C3 H3A 119.6 . . ?
C3 C4 C5 120.7(8) . . ?
C3 C4 C6 117.7(9) . . ?
C5 C4 C6 121.5(9) . . ?
O3 C5 O4 125.1(9) . . ?
O3 C5 C4 119.8(9) . . ?
O4 C5 C4 115.0(8) . . ?
C7 C6 C4 121.6(9) . . ?
C7 C6 H6A 119.2 . . ?
C4 C6 H6A 119.2 . . ?
C6 C7 C8 117.8(5) . . ?
C6 C7 C11 125.0(10) . . ?
C8 C7 C11 117.3(9) . . ?
C2 C8 C7 121.7(8) . . ?
C2 C8 H8A 119.2 . . ?
C7 C8 H8A 119.2 . . ?
C12 C11 C16 120.0 . . ?
C12 C11 C7 116.6(5) . . ?
C16 C11 C7 122.5(5) . . ?
C13 C12 C11 120.0 . . ?
C13 C12 H12A 120.0 . . ?
C11 C12 H12A 120.0 . . ?
C12 C13 C14 120.0 . . ?
C12 C13 O6 121.0(6) . . ?
C14 C13 O6 116.7(6) . . ?
C15 C14 C13 120.0 . . ?
C15 C14 C14 125.6(8) . 12 ?
C13 C14 C14 114.4(8) . 12 ?
C16 C15 C14 120.0 . . ?
C16 C15 C20 120.0 . . ?
C14 C15 C20 120.0 . . ?
C17 C16 C15 120.0 . . ?
C17 C16 C11 120.0 . . ?
C15 C16 C11 120.0 . . ?
C16 C17 C18 120.0 . . ?
C16 C17 H17A 120.0 . . ?
C18 C17 H17A 120.0 . . ?
C17 C18 C19 120.0 . . ?
C17 C18 Cl1 128.9(7) . . ?
C19 C18 Cl1 109.2(7) . . ?
C20 C19 C18 120.0 . . ?
C20 C19 H19A 120.0 . . ?
C18 C19 H19A 120.0 . . ?
C19 C20 C15 120.0 . . ?
C19 C20 H20A 120.0 . . ?
C15 C20 H20A 120.0 . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        67.51
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.548
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.054