# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_c:ad-10
_database_code_depnum_ccdc_archive 'CCDC 1054128'
_audit_update_record             
;
2015-03-16 deposited with the CCDC.
2015-05-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        'Tri-n-butylammonium Trichloroacetate '
_chemical_name_common            ?
_chemical_melting_point          355
_chemical_formula_moiety         'C12 H28 N, C2 Cl3 O2'
_chemical_formula_sum            'C14 H28 Cl3 N O2'
_chemical_formula_weight         348.72

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'
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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   9.6337(3)
_cell_length_b                   10.7137(5)
_cell_length_c                   18.8281(9)
_cell_angle_alpha                98.742(4)
_cell_angle_beta                 100.488(3)
_cell_angle_gamma                100.213(3)
_cell_volume                     1846.15(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       rod
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744
_exptl_absorpt_coefficient_mu    4.502
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\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            11710
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_av_sigmaI/netI    0.0476
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         4.27
_diffrn_reflns_theta_max         66.59
_reflns_number_total             6426
_reflns_number_gt                5432
_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)+(0.0797P)²+0.4526P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6426
_refine_ls_number_parameters     367
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0493
_refine_ls_wR_factor_ref         0.1375
_refine_ls_wR_factor_gt          0.1271
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.001
_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 0.53631(6) 0.38339(6) 0.62531(4) 0.03193(17) Uani 1 1 d . . .
Cl6 Cl 0.09827(7) 0.81934(7) 0.86048(4) 0.03901(19) Uani 1 1 d . . .
Cl2 Cl 0.29904(8) 0.42762(6) 0.52400(4) 0.0418(2) Uani 1 1 d . . .
Cl3 Cl 0.26368(8) 0.37877(7) 0.66717(4) 0.0435(2) Uani 1 1 d . . .
Cl5 Cl 0.38823(8) 0.86275(7) 0.94636(4) 0.0435(2) Uani 1 1 d . . .
Cl4 Cl 0.31148(8) 0.71130(8) 0.79872(4) 0.0455(2) Uani 1 1 d . . .
O1 O 0.38280(17) 0.12109(15) 0.57060(10) 0.0256(4) Uani 1 1 d . . .
O4 O 0.11578(19) 0.62080(18) 0.94910(11) 0.0345(4) Uani 1 1 d . . .
N1 N 0.2507(2) 0.86728(18) 0.53294(10) 0.0185(4) Uani 1 1 d . . .
H1 H 0.2900 0.9553 0.5411 0.022 Uiso 1 1 calc R . .
N2 N 0.21662(19) 0.34125(18) 0.96401(11) 0.0193(4) Uani 1 1 d . . .
H2 H 0.2464 0.4198 0.9503 0.023 Uiso 1 1 calc R . .
C2 C 0.4612(2) 0.8378(2) 0.62557(13) 0.0225(5) Uani 1 1 d . . .
H2A H 0.3976 0.8119 0.6589 0.027 Uiso 1 1 calc R . .
H2B H 0.4963 0.9327 0.6387 0.027 Uiso 1 1 calc R . .
O2 O 0.16499(19) 0.15606(18) 0.52780(13) 0.0404(5) Uani 1 1 d . . .
C25 C -0.1604(2) 0.1147(2) 0.89533(13) 0.0224(5) Uani 1 1 d . . .
H25A H -0.1697 0.1154 0.8422 0.027 Uiso 1 1 calc R . .
H25B H -0.2136 0.1778 0.9155 0.027 Uiso 1 1 calc R . .
C6 C 0.2524(3) 0.8864(3) 0.40162(13) 0.0246(5) Uani 1 1 d . . .
H6A H 0.3425 0.8535 0.4037 0.030 Uiso 1 1 calc R . .
H6B H 0.2793 0.9816 0.4170 0.030 Uiso 1 1 calc R . .
O3 O 0.3005(2) 0.55367(18) 0.91086(12) 0.0374(5) Uani 1 1 d . . .
C5 C 0.1691(2) 0.8299(2) 0.45455(13) 0.0217(5) Uani 1 1 d . . .
H5A H 0.0768 0.8597 0.4505 0.026 Uiso 1 1 calc R . .
H5B H 0.1457 0.7346 0.4401 0.026 Uiso 1 1 calc R . .
C13 C 0.3462(3) 0.3375(2) 0.59235(13) 0.0230(5) Uani 1 1 d . . .
C28 C 0.2154(2) 0.6272(2) 0.91706(13) 0.0209(5) Uani 1 1 d . . .
C21 C 0.3547(3) 0.5020(3) 1.16897(14) 0.0279(5) Uani 1 1 d . . .
H21A H 0.3483 0.4205 1.1881 0.033 Uiso 1 1 calc R . .
H21B H 0.4478 0.5600 1.1950 0.033 Uiso 1 1 calc R . .
C4 C 0.6713(3) 0.8014(3) 0.71559(14) 0.0321(6) Uani 1 1 d . . .
H4A H 0.7075 0.8949 0.7313 0.048 Uiso 1 1 calc R . .
H4B H 0.7527 0.7577 0.7203 0.048 Uiso 1 1 calc R . .
H4C H 0.6062 0.7708 0.7466 0.048 Uiso 1 1 calc R . .
C24 C -0.0015(2) 0.1551(2) 0.93379(13) 0.0202(5) Uani 1 1 d . . .
H24A H 0.0080 0.1567 0.9872 0.024 Uiso 1 1 calc R . .
H24B H 0.0517 0.0913 0.9144 0.024 Uiso 1 1 calc R . .
C14 C 0.2922(2) 0.1885(2) 0.56014(13) 0.0209(5) Uani 1 1 d . . .
C15 C 0.3220(2) 0.2600(2) 0.94643(13) 0.0202(5) Uani 1 1 d . . .
H15A H 0.2982 0.1775 0.9636 0.024 Uiso 1 1 calc R . .
H15B H 0.4201 0.3053 0.9740 0.024 Uiso 1 1 calc R . .
C11 C -0.0169(3) 0.7013(2) 0.63804(14) 0.0249(5) Uani 1 1 d . . .
H11A H 0.0299 0.7553 0.6869 0.030 Uiso 1 1 calc R . .
H11B H -0.1005 0.7367 0.6175 0.030 Uiso 1 1 calc R . .
C26 C -0.2276(3) -0.0201(3) 0.90539(15) 0.0283(6) Uani 1 1 d . . .
H26A H -0.1776 -0.0833 0.8837 0.042 Uiso 1 1 calc R . .
H26B H -0.3300 -0.0421 0.8810 0.042 Uiso 1 1 calc R . .
H26C H -0.2181 -0.0212 0.9580 0.042 Uiso 1 1 calc R . .
C23 C 0.0640(2) 0.2883(2) 0.92160(13) 0.0196(5) Uani 1 1 d . . .
H23A H 0.0620 0.2836 0.8685 0.024 Uiso 1 1 calc R . .
H23B H 0.0032 0.3492 0.9358 0.024 Uiso 1 1 calc R . .
C17 C 0.4471(3) 0.1637(2) 0.85319(13) 0.0241(5) Uani 1 1 d . . .
H17A H 0.5400 0.2239 0.8771 0.029 Uiso 1 1 calc R . .
H17B H 0.4405 0.0876 0.8773 0.029 Uiso 1 1 calc R . .
C1 C 0.3756(2) 0.8012(2) 0.54657(13) 0.0200(5) Uani 1 1 d . . .
H1A H 0.4409 0.8239 0.5134 0.024 Uiso 1 1 calc R . .
H1B H 0.3386 0.7066 0.5343 0.024 Uiso 1 1 calc R . .
C9 C 0.1497(2) 0.8491(2) 0.58509(13) 0.0206(5) Uani 1 1 d . . .
H9A H 0.0676 0.8905 0.5704 0.025 Uiso 1 1 calc R . .
H9B H 0.2017 0.8943 0.6353 0.025 Uiso 1 1 calc R . .
C19 C 0.2225(2) 0.3715(2) 1.04548(13) 0.0222(5) Uani 1 1 d . . .
H19A H 0.1345 0.4022 1.0535 0.027 Uiso 1 1 calc R . .
H19B H 0.2231 0.2914 1.0656 0.027 Uiso 1 1 calc R . .
C22 C 0.2318(3) 0.5651(3) 1.18641(14) 0.0307(6) Uani 1 1 d . . .
H22A H 0.2363 0.6453 1.1670 0.046 Uiso 1 1 calc R . .
H22B H 0.2410 0.5847 1.2398 0.046 Uiso 1 1 calc R . .
H22C H 0.1391 0.5060 1.1636 0.046 Uiso 1 1 calc R . .
C10 C 0.0905(3) 0.7091(2) 0.58749(14) 0.0232(5) Uani 1 1 d . . .
H10A H 0.1709 0.6681 0.6058 0.028 Uiso 1 1 calc R . .
H10B H 0.0418 0.6616 0.5373 0.028 Uiso 1 1 calc R . .
C16 C 0.3235(3) 0.2304(2) 0.86500(13) 0.0236(5) Uani 1 1 d . . .
H16A H 0.3351 0.3117 0.8457 0.028 Uiso 1 1 calc R . .
H16B H 0.2305 0.1738 0.8377 0.028 Uiso 1 1 calc R . .
C3 C 0.5898(3) 0.7719(2) 0.63582(14) 0.0259(5) Uani 1 1 d . . .
H3A H 0.5551 0.6773 0.6197 0.031 Uiso 1 1 calc R . .
H3B H 0.6562 0.8018 0.6045 0.031 Uiso 1 1 calc R . .
C20 C 0.3534(3) 0.4723(3) 1.08636(14) 0.0286(6) Uani 1 1 d . . .
H20A H 0.3537 0.5524 1.0661 0.034 Uiso 1 1 calc R . .
H20B H 0.4417 0.4414 1.0793 0.034 Uiso 1 1 calc R . .
C7 C 0.1635(3) 0.8513(3) 0.32277(14) 0.0303(6) Uani 1 1 d . . .
H7A H 0.2274 0.8748 0.2891 0.036 Uiso 1 1 calc R . .
H7B H 0.1267 0.7566 0.3101 0.036 Uiso 1 1 calc R . .
C18 C 0.4464(3) 0.1202(3) 0.77276(16) 0.0394(7) Uani 1 1 d . . .
H18A H 0.3555 0.0593 0.7488 0.059 Uiso 1 1 calc R . .
H18B H 0.5275 0.0778 0.7686 0.059 Uiso 1 1 calc R . .
H18C H 0.4558 0.1953 0.7488 0.059 Uiso 1 1 calc R . .
C27 C 0.2499(2) 0.7486(2) 0.88049(13) 0.0228(5) Uani 1 1 d . . .
C8 C 0.0364(3) 0.9177(3) 0.31024(15) 0.0350(6) Uani 1 1 d . . .
H8A H -0.0328 0.8879 0.3395 0.052 Uiso 1 1 calc R . .
H8B H -0.0110 0.8965 0.2580 0.052 Uiso 1 1 calc R . .
H8C H 0.0711 1.0114 0.3252 0.052 Uiso 1 1 calc R . .
C12 C -0.0706(3) 0.5633(3) 0.64717(16) 0.0346(6) Uani 1 1 d . . .
H12A H -0.1120 0.5083 0.5987 0.052 Uiso 1 1 calc R . .
H12B H -0.1446 0.5619 0.6767 0.052 Uiso 1 1 calc R . .
H12C H 0.0103 0.5308 0.6720 0.052 Uiso 1 1 calc R . .


_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 C13 1.776(2) . ?
Cl6 C27 1.769(2) . ?
Cl2 C13 1.765(2) . ?
Cl3 C13 1.776(2) . ?
Cl5 C27 1.780(3) . ?
Cl4 C27 1.764(2) . ?
O1 C14 1.236(3) . ?
O4 C28 1.220(3) . ?
N1 C5 1.498(3) . ?
N1 C1 1.502(3) . ?
N1 C9 1.513(3) . ?
N2 C15 1.499(3) . ?
N2 C23 1.503(3) . ?
N2 C19 1.507(3) . ?
C2 C1 1.519(3) . ?
C2 C3 1.528(3) . ?
O2 C14 1.227(3) . ?
C25 C24 1.524(3) . ?
C25 C26 1.528(3) . ?
C6 C5 1.519(3) . ?
C6 C7 1.527(4) . ?
O3 C28 1.242(3) . ?
C13 C14 1.576(3) . ?
C28 C27 1.574(3) . ?
C21 C22 1.524(3) . ?
C21 C20 1.537(3) . ?
C4 C3 1.520(4) . ?
C24 C23 1.523(3) . ?
C15 C16 1.521(3) . ?
C11 C12 1.524(3) . ?
C11 C10 1.528(3) . ?
C17 C18 1.514(4) . ?
C17 C16 1.526(3) . ?
C9 C10 1.518(3) . ?
C19 C20 1.503(3) . ?
C7 C8 1.522(4) . ?

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
C5 N1 C1 111.89(17) . . ?
C5 N1 C9 110.84(17) . . ?
C1 N1 C9 113.83(17) . . ?
C15 N2 C23 114.50(18) . . ?
C15 N2 C19 111.90(17) . . ?
C23 N2 C19 110.99(17) . . ?
C1 C2 C3 111.05(19) . . ?
C24 C25 C26 111.64(19) . . ?
C5 C6 C7 111.5(2) . . ?
N1 C5 C6 112.93(19) . . ?
C14 C13 Cl2 110.18(16) . . ?
C14 C13 Cl3 108.82(16) . . ?
Cl2 C13 Cl3 109.43(13) . . ?
C14 C13 Cl1 113.00(15) . . ?
Cl2 C13 Cl1 107.52(13) . . ?
Cl3 C13 Cl1 107.82(13) . . ?
O4 C28 O3 129.6(2) . . ?
O4 C28 C27 117.3(2) . . ?
O3 C28 C27 112.99(19) . . ?
C22 C21 C20 113.5(2) . . ?
C23 C24 C25 110.73(18) . . ?
O2 C14 O1 129.2(2) . . ?
O2 C14 C13 114.8(2) . . ?
O1 C14 C13 116.1(2) . . ?
N2 C15 C16 113.88(18) . . ?
C12 C11 C10 112.2(2) . . ?
N2 C23 C24 114.10(18) . . ?
C18 C17 C16 113.1(2) . . ?
N1 C1 C2 113.15(18) . . ?
N1 C9 C10 114.38(18) . . ?
C20 C19 N2 112.56(19) . . ?
C9 C10 C11 110.14(19) . . ?
C15 C16 C17 110.40(19) . . ?
C4 C3 C2 111.6(2) . . ?
C19 C20 C21 111.1(2) . . ?
C8 C7 C6 113.8(2) . . ?
C28 C27 Cl4 112.32(16) . . ?
C28 C27 Cl6 112.06(15) . . ?
Cl4 C27 Cl6 108.43(13) . . ?
C28 C27 Cl5 106.07(16) . . ?
Cl4 C27 Cl5 109.33(13) . . ?
Cl6 C27 Cl5 108.52(13) . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        66.59
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.797
_refine_diff_density_min         -0.565
_refine_diff_density_rms         0.072
_chemical_compound_source        No
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_c:\users\adnan\desktop\ad-10-~1\6280
_database_code_depnum_ccdc_archive 'CCDC 1054129'
_audit_update_record             
;
2015-03-16 deposited with the CCDC.
2015-05-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        'Tri-n-butylammonium Trichloroacetate '
_chemical_name_common            ?
_chemical_melting_point          355
_chemical_formula_moiety         'C12 H28 N, C2 Cl3 O2'
_chemical_formula_sum            'C14 H28 Cl3 N O2'
_chemical_formula_weight         348.72

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'
N N 0.0311 0.0180 '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

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

_cell_length_a                   9.6704(3)
_cell_length_b                   10.5407(4)
_cell_length_c                   19.7334(9)
_cell_angle_alpha                98.677(4)
_cell_angle_beta                 101.665(4)
_cell_angle_gamma                98.350(3)
_cell_volume                     1915.04(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       rod
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744
_exptl_absorpt_coefficient_mu    4.340
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.4100
_exptl_absorpt_correction_T_max  0.5621
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      220(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\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            20199
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_sigmaI/netI    0.0266
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         4.31
_diffrn_reflns_theta_max         66.59
_reflns_number_total             6738
_reflns_number_gt                5300
_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)+(0.0805P)²+1.2971P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6738
_refine_ls_number_parameters     416
_refine_ls_number_restraints     54
_refine_ls_R_factor_all          0.0793
_refine_ls_R_factor_gt           0.0643
_refine_ls_wR_factor_ref         0.1813
_refine_ls_wR_factor_gt          0.1657
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.001
_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
Cl3 Cl 0.38614(12) 0.17657(11) 0.64502(6) 0.0934(4) Uani 1 1 d . . .
Cl1 Cl 0.09193(14) 0.12929(11) 0.57271(9) 0.1333(7) Uani 1 1 d . . .
Cl2 Cl 0.1921(2) 0.31942(19) 0.69918(7) 0.1379(7) Uani 1 1 d . . .
Cl5A Cl 0.0400(3) 0.3866(3) 0.1244(4) 0.0867(15) Uani 0.74(2) 1 d PU A 7
Cl4A Cl -0.2291(12) 0.4039(6) 0.1569(6) 0.1181(17) Uani 0.66(4) 1 d PU A 5
Cl6A Cl -0.1935(12) 0.4267(6) 0.0198(5) 0.101(2) Uani 0.61(3) 1 d PU A 9
O4 O 0.1655(2) 0.4208(2) 0.56618(13) 0.0630(6) Uani 1 1 d . . .
O11 O -0.1092(2) 0.12642(18) 0.06277(13) 0.0612(6) Uani 1 1 d . . .
C11 C 0.3673(3) 0.1394(3) 0.40139(19) 0.0614(8) Uani 1 1 d . . .
H11A H 0.3635 0.1365 0.3512 0.074 Uiso 1 1 calc R B 2
H11B H 0.3152 0.2073 0.4168 0.074 Uiso 1 1 calc R B 2
O7 O 0.3692(3) 0.3621(3) 0.55234(17) 0.0862(8) Uani 1 1 d . . .
N2 N 0.2377(3) 0.1308(2) -0.03377(12) 0.0504(6) Uani 1 1 d . C .
H2 H 0.2019 0.0432 -0.0390 0.061 Uiso 1 1 calc R . .
C24 C 0.0345(3) 0.1488(3) -0.13122(19) 0.0621(8) Uani 1 1 d . I .
H24A H 0.0057 0.0537 -0.1409 0.074 Uiso 1 1 calc R . .
H24B H 0.0989 0.1722 -0.1617 0.074 Uiso 1 1 calc R . .
N1 N 0.7480(3) 0.3488(2) 0.46991(13) 0.0524(6) Uani 1 1 d . F .
H1 H 0.7764 0.4309 0.4614 0.063 Uiso 1 1 calc R . .
C20A C 0.2512(5) 0.1113(5) 0.0915(2) 0.0584(15) Uani 0.665(9) 1 d PU C 1
H20A H 0.2480 0.0172 0.0788 0.070 Uiso 0.665(9) 1 calc PR C 1
H20B H 0.1529 0.1261 0.0894 0.070 Uiso 0.665(9) 1 calc PR C 1
C28 C -0.2020(3) 0.1938(3) 0.06240(16) 0.0475(6) Uani 1 1 d . A .
C25 C -0.0988(4) 0.2118(4) -0.1475(3) 0.0823(11) Uani 1 1 d . . .
H25A H -0.1644 0.1856 -0.1182 0.099 Uiso 1 1 calc R D 2
H25B H -0.0699 0.3070 -0.1357 0.099 Uiso 1 1 calc R D 2
C17 C 0.4051(4) 0.2792(3) -0.0838(2) 0.0625(8) Uani 1 1 d . . .
H17A H 0.3266 0.3217 -0.1035 0.075 Uiso 1 1 calc R . .
H17B H 0.4515 0.3287 -0.0365 0.075 Uiso 1 1 calc R . .
C27 C -0.1458(3) 0.3443(3) 0.09101(17) 0.0540(7) Uani 1 1 d . . .
C10 C 0.5226(3) 0.1752(3) 0.44198(17) 0.0545(7) Uani 1 1 d . H .
H10A H 0.5271 0.1751 0.4920 0.065 Uiso 1 1 calc R . .
H10B H 0.5760 0.1094 0.4252 0.065 Uiso 1 1 calc R . .
C9 C 0.5918(3) 0.3077(3) 0.43336(15) 0.0480(6) Uani 1 1 d . . .
H9A H 0.5823 0.3078 0.3830 0.058 Uiso 1 1 calc R H .
H9B H 0.5390 0.3728 0.4514 0.058 Uiso 1 1 calc R . .
C14 C 0.2619(3) 0.3564(3) 0.57553(15) 0.0461(6) Uani 1 1 d . . .
C18 C 0.3449(3) 0.1412(3) -0.07886(17) 0.0520(7) Uani 1 1 d . . .
H18A H 0.2991 0.0928 -0.1265 0.062 Uiso 1 1 calc R . .
H18B H 0.4246 0.0992 -0.0600 0.062 Uiso 1 1 calc R . .
O14 O -0.3308(3) 0.1612(2) 0.0403(2) 0.0980(10) Uani 1 1 d . . .
C13 C 0.2365(3) 0.2511(3) 0.62202(17) 0.0558(7) Uani 1 1 d . . .
C23 C 0.1120(3) 0.1942(3) -0.05552(18) 0.0577(8) Uani 1 1 d . . .
H23A H 0.1450 0.2888 -0.0472 0.069 Uiso 1 1 calc R I .
H23B H 0.0443 0.1769 -0.0257 0.069 Uiso 1 1 calc R . .
C19 C 0.3109(6) 0.1768(4) 0.0429(2) 0.0939(15) Uani 1 1 d . . .
H19A H 0.4122 0.1687 0.0492 0.113 Uiso 0.665(9) 1 d PR C 1
H19B H 0.3078 0.2698 0.0552 0.113 Uiso 0.665(9) 1 d PR C 1
H19C H 0.3900 0.2467 0.0436 0.113 Uiso 0.335(9) 1 d PR C 2
H19D H 0.2414 0.2185 0.0635 0.113 Uiso 0.335(9) 1 d PR C 2
C16 C 0.5128(4) 0.2808(4) -0.1295(2) 0.0723(9) Uani 1 1 d . . .
H16A H 0.4674 0.2266 -0.1758 0.087 Uiso 1 1 calc R . .
H16B H 0.5933 0.2421 -0.1082 0.087 Uiso 1 1 calc R . .
C4 C 0.8440(3) 0.2652(3) 0.4426(2) 0.0645(9) Uani 1 1 d . . .
H4A H 0.9435 0.3024 0.4673 0.077 Uiso 1 1 calc R H .
H4B H 0.8211 0.1784 0.4540 0.077 Uiso 1 1 calc R . .
C3 C 0.8341(4) 0.2505(4) 0.3664(2) 0.0772(10) Uani 1 1 d . G .
H3A H 0.8414 0.3367 0.3531 0.093 Uiso 1 1 calc R E 2
H3B H 0.7404 0.1987 0.3409 0.093 Uiso 1 1 calc R E 2
C5 C 0.7808(5) 0.3601(3) 0.54801(19) 0.0814(11) Uani 1 1 d U . .
H5A H 0.7466 0.2749 0.5588 0.098 Uiso 0.743(8) 1 d PR F 1
H5B H 0.8852 0.3803 0.5658 0.098 Uiso 0.743(8) 1 d PR F 1
H5C H 0.6896 0.3284 0.5595 0.098 Uiso 0.257(8) 1 d PR F 2
H5D H 0.8429 0.2969 0.5586 0.098 Uiso 0.257(8) 1 d PR F 2
C15 C 0.5702(5) 0.4173(5) -0.1392(3) 0.0986(15) Uani 1 1 d . . .
H15A H 0.4943 0.4503 -0.1676 0.148 Uiso 1 1 calc R . .
H15B H 0.6491 0.4145 -0.1625 0.148 Uiso 1 1 calc R . .
H15C H 0.6039 0.4744 -0.0935 0.148 Uiso 1 1 calc R . .
C21 C 0.3438(7) 0.1631(5) 0.1666(2) 0.1023(15) Uani 1 1 d . . .
H21A H 0.3714 0.2577 0.1712 0.123 Uiso 0.665(9) 1 d PR C 1
H21B H 0.2803 0.1491 0.1987 0.123 Uiso 0.665(9) 1 d PR C 1
H21C H 0.3497 0.2570 0.1810 0.123 Uiso 0.335(9) 1 d PR C 2
H21D H 0.2564 0.1150 0.1771 0.123 Uiso 0.335(9) 1 d PR C 2
C2 C 0.9534(5) 0.1834(5) 0.3450(3) 0.1039(16) Uani 1 1 d . G 2
H2A H 1.0457 0.2422 0.3652 0.125 Uiso 1 1 calc R G 2
H2B H 0.9557 0.1047 0.3658 0.125 Uiso 1 1 calc R G 2
C12 C 0.2935(4) 0.0087(4) 0.4115(2) 0.0810(11) Uani 1 1 d . H 2
H12A H 0.3420 -0.0595 0.3943 0.122 Uiso 1 1 calc R H 2
H12B H 0.1942 -0.0089 0.3855 0.122 Uiso 1 1 calc R H 2
H12C H 0.2972 0.0109 0.4612 0.122 Uiso 1 1 calc R H 2
C22 C 0.4743(6) 0.1137(7) 0.1941(3) 0.1171(18) Uani 1 1 d . C 2
H22A H 0.4699 0.0269 0.1682 0.141 Uiso 1 1 d R C 2
H22B H 0.4825 0.1105 0.2436 0.141 Uiso 1 1 d R C 2
H22C H 0.5572 0.1717 0.1887 0.141 Uiso 1 1 d R C 2
C26 C -0.1757(5) 0.1724(6) -0.2239(3) 0.1114(17) Uani 1 1 d . I 2
H26A H -0.1117 0.1999 -0.2531 0.167 Uiso 1 1 calc R I 2
H26B H -0.2594 0.2136 -0.2323 0.167 Uiso 1 1 calc R I 2
H26C H -0.2056 0.0784 -0.2356 0.167 Uiso 1 1 calc R I 2
C6A C 0.7196(5) 0.4543(4) 0.5846(2) 0.0588(12) Uani 0.743(8) 1 d PU F 1
H6A1 H 0.6148 0.4282 0.5727 0.071 Uiso 0.743(8) 1 calc PR F 1
H6A2 H 0.7436 0.5386 0.5706 0.071 Uiso 0.743(8) 1 calc PR F 1
C7 C 0.7783(7) 0.4677(5) 0.6661(2) 0.1026(14) Uani 1 1 d U . .
H7A H 0.7659 0.3817 0.6796 0.123 Uiso 0.743(8) 1 d PR F 1
H7B H 0.8806 0.5067 0.6799 0.123 Uiso 0.743(8) 1 d PR F 1
H7C H 0.7229 0.3789 0.6597 0.123 Uiso 0.257(8) 1 d PR F 2
H7D H 0.8656 0.4709 0.7020 0.123 Uiso 0.257(8) 1 d PR F 2
C8 C 0.6937(6) 0.5506(5) 0.7000(2) 0.1028(15) Uani 1 1 d . F .
H8A H 0.7191 0.6394 0.6930 0.154 Uiso 1 1 calc R . .
H8B H 0.7136 0.5491 0.7501 0.154 Uiso 1 1 calc R . .
H8C H 0.5924 0.5185 0.6795 0.154 Uiso 1 1 calc R . .
C1 C 0.9389(9) 0.1475(9) 0.2710(4) 0.179(4) Uani 1 1 d . . .
H1A H 0.8509 0.0847 0.2508 0.269 Uiso 1 1 calc R G 2
H1B H 1.0202 0.1088 0.2622 0.269 Uiso 1 1 calc R G 2
H1C H 0.9359 0.2244 0.2497 0.269 Uiso 1 1 calc R G 2
C6B C 0.8447(18) 0.4702(13) 0.5948(7) 0.068(3) Uani 0.257(8) 1 d PU F 2
H6B1 H 0.8253 0.5469 0.5745 0.081 Uiso 0.257(8) 1 calc PR F 2
H6B2 H 0.9488 0.4742 0.6070 0.081 Uiso 0.257(8) 1 calc PR F 2
C20B C 0.3600(11) 0.1155(10) 0.0845(5) 0.057(3) Uani 0.335(9) 1 d PU C 2
H20C H 0.4622 0.1200 0.0852 0.069 Uiso 0.335(9) 1 calc PR C 2
H20D H 0.3131 0.0239 0.0685 0.069 Uiso 0.335(9) 1 calc PR C 2
Cl6B Cl -0.131(3) 0.4170(8) 0.0190(8) 0.105(4) Uani 0.39(3) 1 d PU A 10
Cl5B Cl 0.018(2) 0.3682(13) 0.1529(11) 0.118(4) Uani 0.26(2) 1 d PU A 8
Cl4B Cl -0.268(3) 0.4082(8) 0.1327(19) 0.116(5) Uani 0.34(4) 1 d PU A 6


_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
Cl3 C13 1.757(3) . ?
Cl1 C13 1.761(3) . ?
Cl2 C13 1.745(3) . ?
Cl5A C27 1.750(4) . ?
Cl4A C27 1.749(7) . ?
Cl6A C27 1.780(7) . ?
O4 C14 1.231(3) . ?
O11 C28 1.221(3) . ?
C11 C10 1.515(4) . ?
C11 C12 1.518(5) . ?
O7 C14 1.213(3) . ?
N2 C23 1.490(4) . ?
N2 C18 1.499(4) . ?
N2 C19 1.507(4) . ?
C24 C23 1.500(5) . ?
C24 C25 1.533(5) . ?
N1 C5 1.492(4) . ?
N1 C4 1.492(4) . ?
N1 C9 1.504(4) . ?
C20A C19 1.427(6) . ?
C20A C21 1.541(6) . ?
C28 O14 1.213(4) . ?
C28 C27 1.577(4) . ?
C25 C26 1.505(7) . ?
C17 C16 1.510(5) . ?
C17 C18 1.511(4) . ?
C27 Cl4B 1.724(11) . ?
C27 Cl6B 1.733(11) . ?
C27 Cl5B 1.750(11) . ?
C10 C9 1.508(4) . ?
C14 C13 1.567(4) . ?
C19 C20B 1.188(11) . ?
C16 C15 1.520(5) . ?
C4 C3 1.470(5) . ?
C3 C2 1.533(5) . ?
C5 C6B 1.348(14) . ?
C5 C6A 1.409(6) . ?
C21 C22 1.469(7) . ?
C21 C20B 1.666(10) . ?
C2 C1 1.425(9) . ?
C6A C7 1.572(6) . ?
C7 C8 1.460(7) . ?
C7 C6B 1.664(14) . ?

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
C10 C11 C12 112.5(3) . . ?
C23 N2 C18 114.3(2) . . ?
C23 N2 C19 112.4(3) . . ?
C18 N2 C19 110.6(3) . . ?
C23 C24 C25 110.4(3) . . ?
C5 N1 C4 107.2(3) . . ?
C5 N1 C9 115.5(3) . . ?
C4 N1 C9 114.4(2) . . ?
C19 C20A C21 109.6(4) . . ?
O14 C28 O11 128.7(3) . . ?
O14 C28 C27 115.7(2) . . ?
O11 C28 C27 115.5(2) . . ?
C26 C25 C24 111.7(4) . . ?
C16 C17 C18 111.1(3) . . ?
C28 C27 Cl4B 109.4(5) . . ?
C28 C27 Cl6B 107.3(4) . . ?
Cl4B C27 Cl6B 109.9(13) . . ?
C28 C27 Cl4A 111.6(3) . . ?
Cl4B C27 Cl4A 18.4(11) . . ?
Cl6B C27 Cl4A 123.8(7) . . ?
C28 C27 Cl5B 109.8(4) . . ?
Cl4B C27 Cl5B 107.9(16) . . ?
Cl6B C27 Cl5B 112.6(14) . . ?
Cl4A C27 Cl5B 90.5(10) . . ?
C28 C27 Cl5A 114.3(2) . . ?
Cl4B C27 Cl5A 122.8(12) . . ?
Cl6B C27 Cl5A 90.6(9) . . ?
Cl4A C27 Cl5A 107.8(5) . . ?
Cl5B C27 Cl5A 22.6(8) . . ?
C28 C27 Cl6A 107.5(3) . . ?
Cl4B C27 Cl6A 91.1(13) . . ?
Cl6B C27 Cl6A 20.5(5) . . ?
Cl4A C27 Cl6A 107.0(7) . . ?
Cl5B C27 Cl6A 128.8(10) . . ?
Cl5A C27 Cl6A 108.4(5) . . ?
C9 C10 C11 111.5(2) . . ?
N1 C9 C10 115.0(2) . . ?
O7 C14 O4 128.7(3) . . ?
O7 C14 C13 117.3(3) . . ?
O4 C14 C13 113.9(2) . . ?
N2 C18 C17 114.6(2) . . ?
C14 C13 Cl2 110.8(2) . . ?
C14 C13 Cl3 113.1(2) . . ?
Cl2 C13 Cl3 108.46(18) . . ?
C14 C13 Cl1 107.5(2) . . ?
Cl2 C13 Cl1 108.85(19) . . ?
Cl3 C13 Cl1 108.10(18) . . ?
N2 C23 C24 114.0(2) . . ?
C20B C19 C20A 47.9(5) . . ?
C20B C19 N2 128.8(6) . . ?
C20A C19 N2 116.0(4) . . ?
C17 C16 C15 112.9(3) . . ?
C3 C4 N1 115.0(3) . . ?
C4 C3 C2 111.4(4) . . ?
C6B C5 C6A 50.1(7) . . ?
C6B C5 N1 125.0(6) . . ?
C6A C5 N1 115.4(3) . . ?
C22 C21 C20A 122.5(4) . . ?
C22 C21 C20B 90.2(5) . . ?
C20A C21 C20B 39.2(4) . . ?
C1 C2 C3 114.9(5) . . ?
C5 C6A C7 109.8(4) . . ?
C8 C7 C6A 106.3(4) . . ?
C8 C7 C6B 133.1(6) . . ?
C6A C7 C6B 42.2(6) . . ?
C5 C6B C7 107.8(10) . . ?
C19 C20B C21 115.4(7) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        66.59
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.506
_refine_diff_density_min         -0.517
_refine_diff_density_rms         0.052
_chemical_compound_source        No
