# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2011


data_global

_journal_coden_Cambridge         182

loop_
_publ_author_name
'Moyer, Bruce'
'Borman, Christopher'
'Custelcean, Radu'
'Hay, Benjamin'
'Bill, Nathan'
'Sessler, Jonathan'

_publ_contact_author_name        'Moyer, Bruce'
_publ_contact_author_email       MOYERBA@ORNL.GOV

_publ_section_title              
;
Supramolecular Organization of Calix[4]pyrrole with a
Methyl-trialkylammonium Anion Exchanger Leads to
Remarkable Reversal of Selectivity for Sulfate
Extraction vs Nitrate
;

# Attachment '- 1.cif'

data_c:\docume~1\radu\mydocu~1\x-ray\343\343s
_database_code_depnum_ccdc_archive 'CCDC 821449'
#TrackingRef '- 1.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C42 H65 Cl4 N6 O6 S'
_chemical_formula_weight         923.86

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'
S S 0.1246 0.1234 '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           monoclinic
_symmetry_space_group_name_H-M   P2(1)/m

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

_cell_length_a                   10.6011(7)
_cell_length_b                   20.9725(15)
_cell_length_c                   11.2587(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.6120(10)
_cell_angle_gamma                90.00
_cell_volume                     2502.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             982
_exptl_absorpt_coefficient_mu    0.326
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8645
_exptl_absorpt_correction_T_max  0.9619
_exptl_absorpt_process_details   SADABS

_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  ?
_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            15435
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_sigmaI/netI    0.0459
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.05
_diffrn_reflns_theta_max         28.32
_reflns_number_total             6353
_reflns_number_gt                4292
_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.

There was significant disorder in the NMe4 cations that could not be completely
resolved. As a result, some Me groups in NMe4 were refined isotropiocally.
Hydrogen atoms in some of the disordered Me groups were not included in the
structure model. The ethanol molecule included in the crystal displayed moderate
disorder and was therefore refined isotropically. The OH hydrogen could not be
located from the Fourier map and was not included in the final model. The source
of the relatively large R1 factor could not be identified, and is presumably a
result of partial twinning.
;

_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         6353
_refine_ls_number_parameters     282
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1829
_refine_ls_R_factor_gt           0.1469
_refine_ls_wR_factor_ref         0.4435
_refine_ls_wR_factor_gt          0.4100
_refine_ls_goodness_of_fit_ref   1.684
_refine_ls_restrained_S_all      1.684
_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 -0.0678(3) 0.06302(12) 0.3455(3) 0.1225(12) Uani 1 1 d . . .
S1 S 0.21525(13) 0.2500 0.53878(11) 0.0264(4) Uani 1 2 d S . .
O1 O 0.0926(5) 0.2500 0.4815(4) 0.075(2) Uani 1 2 d S . .
N1 N 1.1620(3) 0.13602(16) 0.8160(3) 0.0265(8) Uani 1 1 d . . .
H5 H 1.1772 0.1597 0.7536 0.032 Uiso 1 1 calc R . .
C1 C 1.2529(4) 0.1143(2) 0.8983(4) 0.0293(9) Uani 1 1 d . . .
Cl2 Cl -0.2786(4) 0.08373(19) 0.1870(5) 0.187(2) Uani 1 1 d . . .
O2 O 0.2892(5) 0.1948(2) 0.5065(4) 0.0667(14) Uani 1 1 d . . .
N2 N 0.9422(4) 0.2500 0.7622(4) 0.0242(10) Uani 1 2 d S . .
H2 H 1.0130 0.2500 0.7232 0.029 Uiso 1 2 calc SR . .
C2 C 1.1910(5) 0.0782(2) 0.9798(5) 0.0384(11) Uani 1 1 d . . .
H14 H 1.2289 0.0565 1.0457 0.046 Uiso 1 1 calc R . .
O3 O 0.2001(4) 0.2500 0.6716(3) 0.0272(9) Uani 1 2 d S . .
N3 N 1.3815(4) 0.2500 0.8738(4) 0.0229(10) Uani 1 2 d S . .
H7 H 1.3376 0.2500 0.8063 0.028 Uiso 1 2 calc SR . .
C3 C 1.0605(4) 0.0791(2) 0.9488(5) 0.0349(11) Uani 1 1 d . . .
H22 H 0.9956 0.0585 0.9908 0.042 Uiso 1 1 calc R . .
O4 O 0.4043(12) 0.1206(6) 0.3475(11) 0.196(5) Uiso 1 1 d . . .
N4 N 0.0974(5) 0.2500 0.1619(4) 0.0305(12) Uani 1 2 d S . .
C4 C 1.0445(4) 0.1147(2) 0.8476(4) 0.0286(9) Uani 1 1 d . . .
N5 N 0.6421(6) 0.2500 0.4695(6) 0.098(4) Uani 1 2 d S . .
C5 C 0.9272(4) 0.1290(2) 0.7726(4) 0.0327(10) Uani 1 1 d . . .
C6 C 0.8795(4) 0.1962(2) 0.7966(4) 0.0261(9) Uani 1 1 d . . .
C7 C 0.7770(4) 0.2160(2) 0.8572(4) 0.0329(10) Uani 1 1 d . . .
H16 H 0.7164 0.1893 0.8930 0.039 Uiso 1 1 calc R . .
C8 C 1.4856(4) 0.2171(3) 1.0326(4) 0.0412(12) Uani 1 1 d . . .
H24 H 1.5245 0.1906 1.0915 0.049 Uiso 1 1 calc R . .
C9 C 1.4205(4) 0.1965(2) 0.9338(4) 0.0276(9) Uani 1 1 d . . .
C10 C 1.3914(4) 0.1295(2) 0.8880(4) 0.0319(10) Uani 1 1 d . . .
C11 C 0.9540(5) 0.1216(3) 0.6390(5) 0.0417(12) Uani 1 1 d . . .
H20A H 1.0174 0.1529 0.6162 0.063 Uiso 1 1 calc R . .
H20B H 0.8759 0.1286 0.5921 0.063 Uiso 1 1 calc R . .
H20C H 0.9856 0.0785 0.6240 0.063 Uiso 1 1 calc R . .
C12 C 0.8242(5) 0.0813(2) 0.8079(6) 0.0459(13) Uani 1 1 d . . .
H23A H 0.8538 0.0377 0.7943 0.069 Uiso 1 1 calc R . .
H23B H 0.7474 0.0891 0.7596 0.069 Uiso 1 1 calc R . .
H23C H 0.8060 0.0868 0.8921 0.069 Uiso 1 1 calc R . .
C13 C 1.4317(4) 0.1237(2) 0.7569(4) 0.0356(11) Uani 1 1 d . . .
H18A H 1.4145 0.0803 0.7282 0.053 Uiso 1 1 calc R . .
H18B H 1.5221 0.1327 0.7521 0.053 Uiso 1 1 calc R . .
H18C H 1.3839 0.1543 0.7078 0.053 Uiso 1 1 calc R . .
C14 C 1.4685(5) 0.0807(3) 0.9621(6) 0.0544(16) Uani 1 1 d . . .
H25A H 1.4486 0.0853 1.0462 0.082 Uiso 1 1 calc R . .
H25B H 1.5588 0.0884 0.9521 0.082 Uiso 1 1 calc R . .
H25C H 1.4473 0.0375 0.9353 0.082 Uiso 1 1 calc R . .
C15 C 0.0942(8) 0.2500 0.0281(6) 0.0443(18) Uani 1 2 d S . .
H15A H 0.1807 0.2500 -0.0005 0.066 Uiso 1 2 calc SR . .
H15B H 0.0499 0.2882 -0.0011 0.066 Uiso 0.50 1 calc PR . .
H15C H 0.0499 0.2118 -0.0011 0.066 Uiso 0.50 1 calc PR . .
C16 C 0.035(2) 0.1921(8) 0.2146(11) 0.090(6) Uani 0.50 1 d P . .
C16A C 0.176(2) 0.1934(9) 0.2060(11) 0.084(6) Uani 0.50 1 d P . .
C17 C 0.2301(16) 0.2500 0.1969(17) 0.077(7) Uani 0.50 2 d SP . .
C17A C -0.0320(19) 0.2500 0.197(2) 0.082(7) Uani 0.50 2 d SP . .
C18 C 0.5703(9) 0.2500 0.3544(8) 0.104(5) Uani 1 2 d S . .
H27A H 0.4796 0.2500 0.3692 0.156 Uiso 1 2 calc SR . .
H27B H 0.5919 0.2118 0.3091 0.156 Uiso 0.50 1 calc PR . .
H27C H 0.5919 0.2882 0.3091 0.156 Uiso 0.50 1 calc PR . .
C19 C 0.7814(7) 0.2500 0.4524(9) 0.066(3) Uani 1 2 d S . .
H26A H 0.8255 0.2500 0.5301 0.099 Uiso 1 2 calc SR . .
H26B H 0.8051 0.2882 0.4080 0.099 Uiso 0.50 1 calc PR . .
H26C H 0.8051 0.2118 0.4080 0.099 Uiso 0.50 1 calc PR . .
C20 C 0.6077(17) 0.1989(7) 0.5401(15) 0.172(6) Uiso 1 1 d . . .
H6A H 0.5162 0.1994 0.5498 0.258 Uiso 1 1 calc R . .
H6B H 0.6505 0.2025 0.6182 0.258 Uiso 1 1 calc R . .
H6C H 0.6323 0.1589 0.5022 0.258 Uiso 1 1 calc R . .
C21 C 0.3609(11) 0.0637(5) 0.3219(10) 0.108(3) Uiso 1 1 d . . .
H4A H 0.4301 0.0352 0.2979 0.130 Uiso 1 1 calc R . .
H4B H 0.2970 0.0659 0.2562 0.130 Uiso 1 1 calc R . .
C22 C 0.3018(14) 0.0394(7) 0.4347(14) 0.153(5) Uiso 1 1 d . . .
H7A H 0.2721 -0.0044 0.4224 0.229 Uiso 1 1 calc R . .
H7B H 0.2305 0.0668 0.4546 0.229 Uiso 1 1 calc R . .
H7C H 0.3649 0.0403 0.5000 0.229 Uiso 1 1 calc R . .
C23 C -0.1846(8) 0.0318(5) 0.2651(8) 0.089(3) Uani 1 1 d . . .
H5A H -0.2385 0.0070 0.3187 0.106 Uiso 1 1 calc R . .
H5B H -0.1482 0.0014 0.2082 0.106 Uiso 1 1 calc R . .

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 0.182(3) 0.0772(17) 0.1043(19) -0.0178(13) -0.057(2) 0.0050(16)
S1 0.0252(7) 0.0385(9) 0.0153(6) 0.000 -0.0003(5) 0.000
O1 0.029(3) 0.171(7) 0.023(2) 0.000 -0.011(2) 0.000
N1 0.0237(17) 0.0193(17) 0.0369(19) 0.0074(14) 0.0038(14) 0.0009(13)
C1 0.026(2) 0.023(2) 0.039(2) 0.0102(17) 0.0017(17) 0.0043(16)
Cl2 0.158(3) 0.134(3) 0.263(5) -0.048(3) -0.092(3) 0.074(2)
O2 0.092(3) 0.074(3) 0.0343(19) -0.0148(19) -0.003(2) 0.035(3)
N2 0.021(2) 0.029(3) 0.023(2) 0.000 0.0019(17) 0.000
C2 0.042(3) 0.028(2) 0.045(3) 0.013(2) 0.003(2) 0.0028(19)
O3 0.026(2) 0.038(2) 0.0170(18) 0.000 -0.0011(15) 0.000
N3 0.025(2) 0.023(2) 0.021(2) 0.000 -0.0037(18) 0.000
C3 0.035(2) 0.019(2) 0.051(3) 0.0075(19) 0.016(2) -0.0025(17)
N4 0.036(3) 0.035(3) 0.021(2) 0.000 0.002(2) 0.000
C4 0.027(2) 0.019(2) 0.040(2) -0.0015(17) 0.0076(17) -0.0016(15)
N5 0.024(3) 0.248(13) 0.021(3) 0.000 -0.001(2) 0.000
C5 0.025(2) 0.028(2) 0.045(3) -0.0104(19) 0.0026(18) -0.0081(17)
C6 0.0188(17) 0.028(2) 0.031(2) -0.0025(17) -0.0045(15) -0.0032(15)
C7 0.0216(19) 0.037(3) 0.040(2) 0.0000(19) 0.0013(17) -0.0046(17)
C8 0.034(2) 0.064(3) 0.025(2) 0.012(2) -0.0082(18) 0.005(2)
C9 0.0189(17) 0.038(2) 0.0256(19) 0.0066(17) -0.0010(15) 0.0061(16)
C10 0.0237(19) 0.027(2) 0.045(3) 0.0164(19) 0.0030(18) 0.0063(16)
C11 0.037(2) 0.046(3) 0.042(3) -0.018(2) -0.003(2) -0.005(2)
C12 0.029(2) 0.031(3) 0.078(4) -0.006(2) 0.009(2) -0.0110(19)
C13 0.035(2) 0.025(2) 0.047(3) 0.002(2) 0.011(2) 0.0051(18)
C14 0.037(3) 0.048(3) 0.079(4) 0.034(3) 0.000(3) 0.019(2)
C15 0.069(5) 0.044(4) 0.019(3) 0.000 -0.005(3) 0.000
C16 0.154(17) 0.088(11) 0.030(6) 0.010(6) 0.023(8) -0.069(12)
C16A 0.123(15) 0.100(12) 0.028(5) 0.004(7) 0.000(7) 0.062(11)
C17 0.034(8) 0.15(3) 0.045(10) 0.000 0.002(7) 0.000
C17A 0.052(11) 0.102(19) 0.095(17) 0.000 0.035(11) 0.000
C18 0.051(5) 0.232(16) 0.027(4) 0.000 -0.019(4) 0.000
C19 0.026(4) 0.115(9) 0.057(5) 0.000 0.008(3) 0.000
C23 0.083(5) 0.102(7) 0.081(5) 0.011(5) 0.006(4) 0.025(5)

_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 C23 1.648(9) . ?
S1 O1 1.435(5) . ?
S1 O2 1.450(4) 4_565 ?
S1 O2 1.450(4) . ?
S1 O3 1.509(4) . ?
N1 C4 1.379(5) . ?
N1 C1 1.395(5) . ?
C1 C2 1.370(6) . ?
C1 C10 1.510(6) . ?
Cl2 C23 1.703(9) . ?
N2 C6 1.372(5) . ?
N2 C6 1.372(5) 4_565 ?
C2 C3 1.417(7) . ?
N3 C9 1.367(5) 4_565 ?
N3 C9 1.367(5) . ?
C3 C4 1.369(7) . ?
O4 C21 1.308(14) . ?
N4 C17A 1.440(19) . ?
N4 C17 1.450(18) . ?
N4 C15 1.505(7) . ?
N4 C16 1.515(13) 4_565 ?
N4 C16 1.515(13) . ?
N4 C16A 1.524(14) 4_565 ?
N4 C16A 1.524(13) . ?
C4 C5 1.514(6) . ?
N5 C20 1.389(16) . ?
N5 C20 1.389(16) 4_565 ?
N5 C18 1.483(10) . ?
N5 C19 1.495(10) . ?
C5 C6 1.523(6) . ?
C5 C12 1.541(6) . ?
C5 C11 1.546(7) . ?
C6 C7 1.364(6) . ?
C7 C7 1.426(10) 4_565 ?
C8 C9 1.363(6) . ?
C8 C8 1.382(11) 4_565 ?
C9 C10 1.525(7) . ?
C10 C14 1.541(6) . ?
C10 C13 1.553(7) . ?
C16 C17A 1.42(2) . ?
C16 C16A 1.50(3) . ?
C16A C17 1.33(2) . ?
C17 C16A 1.33(2) 4_565 ?
C17A C16 1.42(2) 4_565 ?
C21 C22 1.519(18) . ?

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 S1 O2 112.1(2) . 4_565 ?
O1 S1 O2 112.1(2) . . ?
O2 S1 O2 106.0(5) 4_565 . ?
O1 S1 O3 109.0(3) . . ?
O2 S1 O3 108.76(19) 4_565 . ?
O2 S1 O3 108.76(19) . . ?
C4 N1 C1 109.6(4) . . ?
C2 C1 N1 106.9(4) . . ?
C2 C1 C10 130.8(4) . . ?
N1 C1 C10 122.3(4) . . ?
C6 N2 C6 110.8(5) . 4_565 ?
C1 C2 C3 108.1(4) . . ?
C9 N3 C9 110.3(5) 4_565 . ?
C4 C3 C2 108.0(4) . . ?
C17A N4 C17 148.1(14) . . ?
C17A N4 C15 106.4(12) . . ?
C17 N4 C15 105.5(9) . . ?
C17A N4 C16 57.2(10) . 4_565 ?
C17 N4 C16 109.1(10) . 4_565 ?
C15 N4 C16 113.2(6) . 4_565 ?
C17A N4 C16 57.2(10) . . ?
C17 N4 C16 109.1(10) . . ?
C15 N4 C16 113.2(6) . . ?
C16 N4 C16 106.6(16) 4_565 . ?
C17A N4 C16A 115.1(10) . 4_565 ?
C17 N4 C16A 52.9(9) . 4_565 ?
C15 N4 C16A 108.8(6) . 4_565 ?
C16 N4 C16A 59.3(11) 4_565 4_565 ?
C16 N4 C16A 137.6(8) . 4_565 ?
C17A N4 C16A 115.1(10) . . ?
C17 N4 C16A 52.9(9) . . ?
C15 N4 C16A 108.8(6) . . ?
C16 N4 C16A 137.6(8) 4_565 . ?
C16 N4 C16A 59.3(11) . . ?
C16A N4 C16A 102.4(17) 4_565 . ?
C3 C4 N1 107.4(4) . . ?
C3 C4 C5 130.8(4) . . ?
N1 C4 C5 121.7(4) . . ?
C20 N5 C20 100.9(15) . 4_565 ?
C20 N5 C18 111.3(8) . . ?
C20 N5 C18 111.3(8) 4_565 . ?
C20 N5 C19 110.5(8) . . ?
C20 N5 C19 110.5(8) 4_565 . ?
C18 N5 C19 111.9(7) . . ?
C4 C5 C6 110.9(3) . . ?
C4 C5 C12 107.7(4) . . ?
C6 C5 C12 108.2(4) . . ?
C4 C5 C11 110.6(4) . . ?
C6 C5 C11 109.7(4) . . ?
C12 C5 C11 109.6(4) . . ?
C7 C6 N2 106.8(4) . . ?
C7 C6 C5 130.1(4) . . ?
N2 C6 C5 123.0(4) . . ?
C6 C7 C7 107.8(3) . 4_565 ?
C9 C8 C8 108.4(3) . 4_565 ?
C8 C9 N3 106.4(4) . . ?
C8 C9 C10 131.3(4) . . ?
N3 C9 C10 122.3(4) . . ?
C1 C10 C9 110.9(4) . . ?
C1 C10 C14 108.7(4) . . ?
C9 C10 C14 109.2(4) . . ?
C1 C10 C13 110.5(4) . . ?
C9 C10 C13 109.6(3) . . ?
C14 C10 C13 107.8(4) . . ?
C17A C16 C16A 118.0(14) . . ?
C17A C16 N4 58.8(10) . . ?
C16A C16 N4 60.7(9) . . ?
C17 C16A C16 117.2(14) . . ?
C17 C16A N4 60.7(10) . . ?
C16 C16A N4 60.1(9) . . ?
C16A C17 C16A 127(2) . 4_565 ?
C16A C17 N4 66.4(10) . . ?
C16A C17 N4 66.4(10) 4_565 . ?
C16 C17A C16 118(2) 4_565 . ?
C16 C17A N4 64.1(10) 4_565 . ?
C16 C17A N4 64.1(10) . . ?
O4 C21 C22 105.8(11) . . ?
Cl1 C23 Cl2 116.7(6) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        28.32
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         2.415
_refine_diff_density_min         -1.352
_refine_diff_density_rms         0.168