# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2016

####################################################################### 
# 
# 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_Global
_database_code_depnum_ccdc_archive 'CCDC 981470'
_audit_update_record             
;
2014-01-14 deposited with the CCDC.
2016-06-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'9-Carboxy-10-methylacridinium chloride dihydrate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H12 N O2, Cl, 2(H2 O)'
_chemical_formula_sum            'C15 H16 Cl N O4'

_chemical_formula_weight         309.74

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'
Cl Cl 0.1484 0.1585 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   9.2602(6)
_cell_length_b                   7.3075(4)
_cell_length_c                   22.2069(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.583(5)
_cell_angle_gamma                90.00
_cell_volume                     1499.78(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    1780
_cell_measurement_theta_min      3.3327
_cell_measurement_theta_max      29.0776

_exptl_crystal_description       prism
_exptl_crystal_colour            light-orange
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
__exptl_crystal_density_diffrn   1.372
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648
_exptl_absorpt_coefficient_mu    0.269
_exptl_absorpt_correction_T_min  0.46268
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;


_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(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  'Oxford Diffraction Ruby CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.4002
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9482
_diffrn_reflns_av_R_equivalents  0.0827
_diffrn_reflns_av_sigmaI/netI    0.0720
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.34
_diffrn_reflns_theta_max         25.05
_reflns_number_total             2644
_reflns_number_gt                1440
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'CrysAlis CCD,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)'
_computing_cell_refinement       
'CrysAlis RED,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)'
_computing_data_reduction        
'CrysAlis RED,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 and PLATON (Spek, 2009)'

_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)+(0.0589P)²+0.0000P] 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         2644
_refine_ls_number_parameters     203
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1125
_refine_ls_R_factor_gt           0.0538
_refine_ls_wR_factor_ref         0.1512
_refine_ls_wR_factor_gt          0.1196
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_restrained_S_all      0.979
_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
C1 C 0.3552(4) 0.2015(5) 0.43382(16) 0.0647(9) Uani 1 1 d . . .
H1 H 0.4298 0.1754 0.4625 0.078 Uiso 1 1 calc R . .
O1W O 0.5138(3) 0.2664(3) 0.67465(10) 0.0716(7) Uani 1 1 d D . .
H2W H 0.488(4) 0.169(3) 0.6920(16) 0.107 Uiso 1 1 d D . .
H1W H 0.505(4) 0.357(3) 0.6986(14) 0.107 Uiso 1 1 d D . .
Cl1 Cl 0.43028(11) 0.57601(12) 0.75714(4) 0.0812(4) Uani 1 1 d . . .
C2 C 0.3840(4) 0.2177(5) 0.37554(18) 0.0782(11) Uani 1 1 d . . .
H2 H 0.4780 0.2006 0.3642 0.094 Uiso 1 1 calc R . .
O2W O 0.4015(3) -0.0021(4) 0.73821(13) 0.0843(8) Uani 1 1 d D . .
H4W H 0.420(4) -0.113(3) 0.747(2) 0.126 Uiso 1 1 d D . .
H3W H 0.311(2) 0.016(6) 0.740(2) 0.126 Uiso 1 1 d D . .
C3 C 0.2743(4) 0.2599(5) 0.33201(17) 0.0797(11) Uani 1 1 d . . .
H3 H 0.2970 0.2733 0.2920 0.096 Uiso 1 1 calc R . .
C4 C 0.1340(4) 0.2822(5) 0.34642(16) 0.0695(10) Uani 1 1 d . . .
H4 H 0.0621 0.3089 0.3166 0.083 Uiso 1 1 calc R . .
C5 C -0.2162(4) 0.3077(4) 0.50037(16) 0.0596(9) Uani 1 1 d . . .
H5 H -0.2890 0.3403 0.4716 0.072 Uiso 1 1 calc R . .
C6 C -0.2458(4) 0.2912(5) 0.55899(17) 0.0687(10) Uani 1 1 d . . .
H6 H -0.3397 0.3131 0.5698 0.082 Uiso 1 1 calc R . .
C7 C -0.1413(5) 0.2428(5) 0.60370(17) 0.0706(10) Uani 1 1 d . . .
H7 H -0.1665 0.2291 0.6433 0.085 Uiso 1 1 calc R . .
C8 C -0.0017(4) 0.2153(4) 0.58956(15) 0.0611(9) Uani 1 1 d . . .
H8 H 0.0689 0.1852 0.6196 0.073 Uiso 1 1 calc R . .
C9 C 0.1778(4) 0.2114(4) 0.51215(14) 0.0528(8) Uani 1 1 d . . .
N10 N -0.0401(3) 0.2859(3) 0.42378(11) 0.0517(7) Uani 1 1 d . . .
C11 C 0.2115(4) 0.2237(4) 0.45205(14) 0.0534(8) Uani 1 1 d . . .
C12 C 0.0995(4) 0.2640(4) 0.40744(14) 0.0516(8) Uani 1 1 d . . .
C13 C 0.0352(4) 0.2332(4) 0.52842(14) 0.0513(8) Uani 1 1 d . . .
C14 C -0.0738(4) 0.2752(4) 0.48287(14) 0.0504(8) Uani 1 1 d . . .
C15 C 0.2962(4) 0.1721(5) 0.56061(14) 0.0597(9) Uani 1 1 d . . .
O16 O 0.3545(2) 0.3192(3) 0.58286(10) 0.0731(7) Uani 1 1 d . . .
H16 H 0.3973 0.2960 0.6154 0.110 Uiso 1 1 calc R . .
O17 O 0.3276(3) 0.0183(3) 0.57508(11) 0.0931(9) Uani 1 1 d . . .
C18 C -0.1541(4) 0.3199(5) 0.37538(15) 0.0683(10) Uani 1 1 d . . .
H18A H -0.2470 0.3210 0.3923 0.103 Uiso 1 1 calc R . .
H18B H -0.1518 0.2248 0.3456 0.103 Uiso 1 1 calc R . .
H18C H -0.1373 0.4360 0.3568 0.103 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
C1 C2 1.343(5) . ?
C1 C11 1.424(4) . ?
C1 H1 0.9300 . ?
O1W H2W 0.851(18) . ?
O1W H1W 0.853(18) . ?
C2 C3 1.393(5) . ?
C2 H2 0.9300 . ?
O2W H4W 0.851(18) . ?
O2W H3W 0.851(18) . ?
C3 C4 1.367(5) . ?
C3 H3 0.9300 . ?
C4 C12 1.418(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.352(5) . ?
C5 C14 1.418(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.389(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.364(5) . ?
C7 H7 0.9300 . ?
C8 C13 1.427(4) . ?
C8 H8 0.9300 . ?
C9 C11 1.393(4) . ?
C9 C13 1.400(4) . ?
C9 C15 1.515(5) . ?
N10 C14 1.370(4) . ?
N10 C12 1.374(4) . ?
N10 C18 1.479(4) . ?
C11 C12 1.419(4) . ?
C13 C14 1.417(4) . ?
C15 O17 1.199(4) . ?
C15 O16 1.288(4) . ?
O16 H16 0.8200 . ?
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
C2 C1 C11 120.6(3) . . ?
C2 C1 H1 119.7 . . ?
C11 C1 H1 119.7 . . ?
H2W O1W H1W 109(3) . . ?
C1 C2 C3 120.5(4) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
H4W O2W H3W 108(3) . . ?
C4 C3 C2 121.8(4) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C3 C4 C12 119.1(3) . . ?
C3 C4 H4 120.4 . . ?
C12 C4 H4 120.4 . . ?
C6 C5 C14 119.8(3) . . ?
C6 C5 H5 120.1 . . ?
C14 C5 H5 120.1 . . ?
C5 C6 C7 122.5(3) . . ?
C5 C6 H6 118.8 . . ?
C7 C6 H6 118.8 . . ?
C8 C7 C6 120.1(3) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C8 C13 119.5(3) . . ?
C7 C8 H8 120.3 . . ?
C13 C8 H8 120.3 . . ?
C11 C9 C13 120.8(3) . . ?
C11 C9 C15 119.8(3) . . ?
C13 C9 C15 119.4(3) . . ?
C14 N10 C12 121.4(3) . . ?
C14 N10 C18 120.7(3) . . ?
C12 N10 C18 117.9(3) . . ?
C9 C11 C12 119.0(3) . . ?
C9 C11 C1 122.3(3) . . ?
C12 C11 C1 118.7(3) . . ?
N10 C12 C4 120.9(3) . . ?
N10 C12 C11 119.9(3) . . ?
C4 C12 C11 119.2(3) . . ?
C9 C13 C14 118.8(3) . . ?
C9 C13 C8 121.4(3) . . ?
C14 C13 C8 119.8(3) . . ?
N10 C14 C13 120.1(3) . . ?
N10 C14 C5 121.6(3) . . ?
C13 C14 C5 118.3(3) . . ?
O17 C15 O16 126.2(3) . . ?
O17 C15 C9 121.4(3) . . ?
O16 C15 C9 112.4(3) . . ?
C15 O16 H16 109.5 . . ?
N10 C18 H18A 109.5 . . ?
N10 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N10 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 C1 C2 C3 1.2(6) . . . . ?
C1 C2 C3 C4 -1.5(6) . . . . ?
C2 C3 C4 C12 0.8(6) . . . . ?
C14 C5 C6 C7 -0.1(5) . . . . ?
C5 C6 C7 C8 2.0(5) . . . . ?
C6 C7 C8 C13 -1.2(5) . . . . ?
C13 C9 C11 C12 1.8(4) . . . . ?
C15 C9 C11 C12 -178.8(3) . . . . ?
C13 C9 C11 C1 -179.7(3) . . . . ?
C15 C9 C11 C1 -0.3(4) . . . . ?
C2 C1 C11 C9 -178.8(3) . . . . ?
C2 C1 C11 C12 -0.2(5) . . . . ?
C14 N10 C12 C4 -177.6(3) . . . . ?
C18 N10 C12 C4 3.0(4) . . . . ?
C14 N10 C12 C11 2.0(4) . . . . ?
C18 N10 C12 C11 -177.4(3) . . . . ?
C3 C4 C12 N10 179.8(3) . . . . ?
C3 C4 C12 C11 0.2(5) . . . . ?
C9 C11 C12 N10 -1.5(4) . . . . ?
C1 C11 C12 N10 179.9(3) . . . . ?
C9 C11 C12 C4 178.1(3) . . . . ?
C1 C11 C12 C4 -0.5(4) . . . . ?
C11 C9 C13 C14 -2.4(4) . . . . ?
C15 C9 C13 C14 178.2(3) . . . . ?
C11 C9 C13 C8 178.1(3) . . . . ?
C15 C9 C13 C8 -1.3(4) . . . . ?
C7 C8 C13 C9 178.1(3) . . . . ?
C7 C8 C13 C14 -1.4(4) . . . . ?
C12 N10 C14 C13 -2.6(4) . . . . ?
C18 N10 C14 C13 176.7(3) . . . . ?
C12 N10 C14 C5 176.4(3) . . . . ?
C18 N10 C14 C5 -4.2(4) . . . . ?
C9 C13 C14 N10 2.8(4) . . . . ?
C8 C13 C14 N10 -177.6(2) . . . . ?
C9 C13 C14 C5 -176.3(3) . . . . ?
C8 C13 C14 C5 3.2(4) . . . . ?
C6 C5 C14 N10 178.4(3) . . . . ?
C6 C5 C14 C13 -2.5(4) . . . . ?
C11 C9 C15 O17 -89.5(4) . . . . ?
C13 C9 C15 O17 89.9(4) . . . . ?
C11 C9 C15 O16 90.7(3) . . . . ?
C13 C9 C15 O16 -89.9(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.042


####################################################################### 
# 
# 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_Global
_database_code_depnum_ccdc_archive 'CCDC 981471'
_audit_update_record             
;
2014-01-14 deposited with the CCDC.
2016-06-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'Hydrogen bis(9-carboxy-10-methylacridinium) trifluoromethanesulfonate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H23 N2 O4, C F3 O3 S'
_chemical_formula_sum            'C31 H23 F3 N2 O7 S'

_chemical_formula_weight         624.58

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'
F F 0.0171 0.0103 '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'
S S 0.1246 0.1234 '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'
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   8.2989(9)
_cell_length_b                   9.0995(10)
_cell_length_c                   9.8014(9)
_cell_angle_alpha                72.396(9)
_cell_angle_beta                 77.357(8)
_cell_angle_gamma                78.795(9)
_cell_volume                     681.82(12)
_cell_formula_units_Z            1
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    1645
_cell_measurement_theta_min      3.6367
_cell_measurement_theta_max      29.1048

_exptl_crystal_description       needle
_exptl_crystal_colour            light-orange
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.521
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             322
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_T_min  0.96798
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;


_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(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  'Oxford Diffraction Ruby CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.4002
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4515
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_sigmaI/netI    0.0521
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.64
_diffrn_reflns_theta_max         25.05
_reflns_number_total             2408
_reflns_number_gt                1562
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'CrysAlis CCD,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)'
_computing_cell_refinement       
'CrysAlis RED,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)'
_computing_data_reduction        
'CrysAlis RED,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 and PLATON (Spek, 2009)'

_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)+(0.0473P)²+0.0000P] 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       0.016(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2408
_refine_ls_number_parameters     238
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0827
_refine_ls_R_factor_gt           0.0436
_refine_ls_wR_factor_ref         0.1072
_refine_ls_wR_factor_gt          0.0909
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_restrained_S_all      0.996
_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
C1 C 0.8691(3) 0.6287(2) 0.3480(2) 0.0480(6) Uani 1 1 d . . .
H1 H 0.8710 0.7356 0.3228 0.058 Uiso 1 1 calc R . .
C2 C 0.7589(3) 0.5631(3) 0.4633(2) 0.0570(7) Uani 1 1 d . . .
H2 H 0.6857 0.6243 0.5173 0.068 Uiso 1 1 calc R . .
C3 C 0.7555(3) 0.4019(3) 0.5014(2) 0.0560(6) Uani 1 1 d . . .
H3 H 0.6779 0.3578 0.5799 0.067 Uiso 1 1 calc R . .
C4 C 0.8618(3) 0.3094(2) 0.4269(2) 0.0475(6) Uani 1 1 d . . .
H4 H 0.8577 0.2028 0.4554 0.057 Uiso 1 1 calc R . .
C5 C 1.3043(3) 0.2521(3) 0.0216(2) 0.0483(6) Uani 1 1 d . . .
H5 H 1.3071 0.1446 0.0515 0.058 Uiso 1 1 calc R . .
C6 C 1.4031(3) 0.3188(3) -0.1012(3) 0.0576(7) Uani 1 1 d . . .
H6 H 1.4720 0.2562 -0.1560 0.069 Uiso 1 1 calc R . .
C7 C 1.4050(3) 0.4806(3) -0.1491(2) 0.0559(6) Uani 1 1 d . . .
H7 H 1.4748 0.5235 -0.2343 0.067 Uiso 1 1 calc R . .
C8 C 1.3060(3) 0.5735(3) -0.0716(2) 0.0466(6) Uani 1 1 d . . .
H8 H 1.3081 0.6805 -0.1037 0.056 Uiso 1 1 calc R . .
C9 C 1.0948(2) 0.6027(2) 0.1422(2) 0.0358(5) Uani 1 1 d . . .
N10 N 1.0894(2) 0.28259(16) 0.22861(17) 0.0375(4) Uani 1 1 d . . .
C11 C 0.9825(3) 0.5370(2) 0.2644(2) 0.0359(5) Uani 1 1 d . . .
C12 C 0.9796(3) 0.3737(2) 0.3056(2) 0.0364(5) Uani 1 1 d . . .
C13 C 1.1977(2) 0.5096(2) 0.0594(2) 0.0362(5) Uani 1 1 d . . .
C14 C 1.1966(2) 0.3451(2) 0.1053(2) 0.0361(5) Uani 1 1 d . . .
C15 C 1.1060(3) 0.7753(2) 0.1034(2) 0.0419(5) Uani 1 1 d . . .
O16 O 1.0060(2) 0.85956(16) 0.02089(19) 0.0737(6) Uani 1 1 d . . .
H16 H 1.0000 1.0000 0.0000 0.137(16) Uiso 1 2 d S . .
O17 O 1.2042(2) 0.81711(15) 0.15349(17) 0.0609(5) Uani 1 1 d . . .
C18 C 1.0933(3) 0.1112(2) 0.2838(3) 0.0566(7) Uani 1 1 d . . .
H18A H 1.1907 0.0609 0.2338 0.085 Uiso 1 1 calc R . .
H18B H 0.9953 0.0825 0.2673 0.085 Uiso 1 1 calc R . .
H18C H 1.0963 0.0794 0.3861 0.085 Uiso 1 1 calc R . .
S19 S 0.5372(3) 1.0141(3) 0.4097(2) 0.0443(6) Uani 0.50 1 d P . .
O20 O 0.4749(14) 1.1624(19) 0.321(2) 0.080(4) Uani 0.50 1 d P . .
O21 O 0.719(3) 0.984(2) 0.394(3) 0.082(4) Uani 0.50 1 d P . .
O22 O 0.463(3) 0.900(3) 0.376(3) 0.077(5) Uani 0.50 1 d P . .
C23 C 0.459(3) 0.977(2) 0.598(2) 0.151(8) Uani 0.50 1 d P . .
F24 F 0.5243(17) 0.8299(16) 0.649(2) 0.110(5) Uani 0.50 1 d P . .
F25 F 0.301(2) 0.997(2) 0.630(2) 0.117(6) Uani 0.50 1 d P . .
F26 F 0.509(3) 1.080(2) 0.655(3) 0.088(5) Uani 0.50 1 d P . .


_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
C1 C2 1.350(3) . ?
C1 C11 1.423(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.404(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.350(3) . ?
C3 H3 0.9300 . ?
C4 C12 1.416(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.345(3) . ?
C5 C14 1.412(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.405(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.346(3) . ?
C7 H7 0.9300 . ?
C8 C13 1.428(3) . ?
C8 H8 0.9300 . ?
C9 C13 1.393(3) . ?
C9 C11 1.398(3) . ?
C9 C15 1.517(3) . ?
N10 C12 1.368(2) . ?
N10 C14 1.373(2) . ?
N10 C18 1.485(2) . ?
C11 C12 1.420(2) . ?
C13 C14 1.428(2) . ?
C15 O17 1.208(2) . ?
C15 O16 1.265(2) . ?
O16 H16 1.224(14) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
S19 C23 0.10(2) 2_676 ?
S19 F25 1.304(19) 2_676 ?
S19 F26 1.36(2) 2_676 ?
S19 F24 1.399(14) 2_676 ?
S19 O20 1.435(17) . ?
S19 O22 1.45(3) . ?
S19 O21 1.46(2) . ?
S19 S19 1.700(5) 2_676 ?
S19 C23 1.772(16) . ?
O20 F24 0.33(4) 2_676 ?
O20 C23 1.36(3) 2_676 ?
O21 F25 0.31(6) 2_676 ?
O21 C23 1.44(3) 2_676 ?
O22 F26 0.36(5) 2_676 ?
O22 C23 1.50(3) 2_676 ?
C23 S19 0.10(2) 2_676 ?
C23 F25 1.27(3) . ?
C23 F24 1.33(2) . ?
C23 O20 1.36(3) 2_676 ?
C23 F26 1.39(3) . ?
C23 O21 1.44(3) 2_676 ?
C23 O22 1.50(3) 2_676 ?
C23 C23 1.85(4) 2_676 ?
F24 O20 0.33(4) 2_676 ?
F24 S19 1.399(14) 2_676 ?
F25 O21 0.31(6) 2_676 ?
F25 S19 1.304(19) 2_676 ?
F26 O22 0.36(5) 2_676 ?
F26 S19 1.36(2) 2_676 ?

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
C2 C1 C11 121.01(19) . . ?
C2 C1 H1 119.5 . . ?
C11 C1 H1 119.5 . . ?
C1 C2 C3 119.6(2) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C4 C3 C2 121.7(2) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C3 C4 C12 120.34(19) . . ?
C3 C4 H4 119.8 . . ?
C12 C4 H4 119.8 . . ?
C6 C5 C14 120.1(2) . . ?
C6 C5 H5 119.9 . . ?
C14 C5 H5 119.9 . . ?
C5 C6 C7 121.8(2) . . ?
C5 C6 H6 119.1 . . ?
C7 C6 H6 119.1 . . ?
C8 C7 C6 120.1(2) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C8 C13 120.7(2) . . ?
C7 C8 H8 119.7 . . ?
C13 C8 H8 119.7 . . ?
C13 C9 C11 120.17(17) . . ?
C13 C9 C15 120.54(17) . . ?
C11 C9 C15 119.27(17) . . ?
C12 N10 C14 121.93(15) . . ?
C12 N10 C18 118.08(16) . . ?
C14 N10 C18 119.98(16) . . ?
C9 C11 C12 119.11(17) . . ?
C9 C11 C1 122.11(17) . . ?
C12 C11 C1 118.78(18) . . ?
N10 C12 C4 121.57(17) . . ?
N10 C12 C11 119.91(17) . . ?
C4 C12 C11 118.52(18) . . ?
C9 C13 C14 119.71(17) . . ?
C9 C13 C8 121.93(18) . . ?
C14 C13 C8 118.36(18) . . ?
N10 C14 C5 122.10(17) . . ?
N10 C14 C13 118.96(16) . . ?
C5 C14 C13 118.94(18) . . ?
O17 C15 O16 127.70(19) . . ?
O17 C15 C9 118.46(18) . . ?
O16 C15 C9 113.84(19) . . ?
C15 O16 H16 115.18(15) . . ?
N10 C18 H18A 109.5 . . ?
N10 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N10 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C23 S19 F25 67(10) 2_676 2_676 ?
C23 S19 F26 105(10) 2_676 2_676 ?
F25 S19 F26 104.1(11) 2_676 2_676 ?
C23 S19 F24 42(10) 2_676 2_676 ?
F25 S19 F24 105.8(11) 2_676 2_676 ?
F26 S19 F24 110.9(12) 2_676 2_676 ?
C23 S19 O20 38(10) 2_676 . ?
F25 S19 O20 104.6(11) 2_676 . ?
F26 S19 O20 99.0(13) 2_676 . ?
F24 S19 O20 13.1(16) 2_676 . ?
C23 S19 O22 118(10) 2_676 . ?
F25 S19 O22 113.5(11) 2_676 . ?
F26 S19 O22 14(2) 2_676 . ?
F24 S19 O22 115.9(12) 2_676 . ?
O20 S19 O22 105.7(12) . . ?
C23 S19 O21 77(10) 2_676 . ?
F25 S19 O21 11(2) 2_676 . ?
F26 S19 O21 107.1(11) 2_676 . ?
F24 S19 O21 113.8(9) 2_676 . ?
O20 S19 O21 114.2(10) . . ?
O22 S19 O21 114.2(10) . . ?
C23 S19 S19 135(10) 2_676 2_676 ?
F25 S19 S19 116.8(11) 2_676 2_676 ?
F26 S19 S19 116.2(10) 2_676 2_676 ?
F24 S19 S19 102.7(7) 2_676 2_676 ?
O20 S19 S19 114.0(8) . 2_676 ?
O22 S19 S19 102.0(11) . 2_676 ?
O21 S19 S19 106.3(10) . 2_676 ?
C23 S19 C23 137(10) 2_676 . ?
F25 S19 C23 117.1(12) 2_676 . ?
F26 S19 C23 114.1(11) 2_676 . ?
F24 S19 C23 104.6(10) 2_676 . ?
O20 S19 C23 115.8(9) . . ?
O22 S19 C23 99.9(13) . . ?
O21 S19 C23 106.4(13) . . ?
S19 S19 C23 2.3(7) 2_676 . ?
F24 O20 C23 78(5) 2_676 2_676 ?
F24 O20 S19 77(5) 2_676 . ?
C23 O20 S19 2.6(9) 2_676 . ?
F25 O21 C23 51(6) 2_676 2_676 ?
F25 O21 S19 55(6) 2_676 . ?
C23 O21 S19 3.9(8) 2_676 . ?
F26 O22 S19 68(8) 2_676 . ?
F26 O22 C23 65(8) 2_676 2_676 ?
S19 O22 C23 3.4(8) . 2_676 ?
S19 C23 F25 109(10) 2_676 . ?
S19 C23 F24 135(10) 2_676 . ?
F25 C23 F24 112.5(18) . . ?
S19 C23 O20 140(10) 2_676 2_676 ?
F25 C23 O20 111.3(18) . 2_676 ?
F24 C23 O20 13.9(17) . 2_676 ?
S19 C23 F26 71(10) 2_676 . ?
F25 C23 F26 104.4(17) . . ?
F24 C23 F26 114(2) . . ?
O20 C23 F26 101(2) 2_676 . ?
S19 C23 O21 99(10) 2_676 2_676 ?
F25 C23 O21 11(2) . 2_676 ?
F24 C23 O21 119.8(17) . 2_676 ?
O20 C23 O21 120.6(17) 2_676 2_676 ?
F26 C23 O21 106.6(16) . 2_676 ?
S19 C23 O22 59(10) 2_676 2_676 ?
F25 C23 O22 112.5(16) . 2_676 ?
F24 C23 O22 117(2) . 2_676 ?
O20 C23 O22 107(2) 2_676 2_676 ?
F26 C23 O22 14(2) . 2_676 ?
O21 C23 O22 112.4(15) 2_676 2_676 ?
S19 C23 S19 43(10) 2_676 . ?
F25 C23 S19 114.2(17) . . ?
F24 C23 S19 102.2(13) . . ?
O20 C23 S19 114.0(13) 2_676 . ?
F26 C23 S19 110.3(14) . . ?
O21 C23 S19 103.6(17) 2_676 . ?
O22 C23 S19 96.8(15) 2_676 . ?
S19 C23 C23 41(10) 2_676 2_676 ?
F25 C23 C23 114(2) . 2_676 ?
F24 C23 C23 104.0(18) . 2_676 ?
O20 C23 C23 115.5(18) 2_676 2_676 ?
F26 C23 C23 108.4(18) . 2_676 ?
O21 C23 C23 104(2) 2_676 2_676 ?
O22 C23 C23 94.9(19) 2_676 2_676 ?
S19 C23 C23 2.1(6) . 2_676 ?
O20 F24 C23 88(5) 2_676 . ?
O20 F24 S19 90(5) 2_676 2_676 ?
C23 F24 S19 2.9(9) . 2_676 ?
O21 F25 C23 118(7) 2_676 . ?
O21 F25 S19 114(7) 2_676 2_676 ?
C23 F25 S19 4.2(10) . 2_676 ?
O22 F26 S19 98(8) 2_676 2_676 ?
O22 F26 C23 102(9) 2_676 . ?
S19 F26 C23 4.0(9) 2_676 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 C1 C2 C3 -0.2(3) . . . . ?
C1 C2 C3 C4 1.1(4) . . . . ?
C2 C3 C4 C12 -0.9(3) . . . . ?
C14 C5 C6 C7 1.1(3) . . . . ?
C5 C6 C7 C8 -0.2(3) . . . . ?
C6 C7 C8 C13 -0.2(3) . . . . ?
C13 C9 C11 C12 2.4(3) . . . . ?
C15 C9 C11 C12 -176.12(18) . . . . ?
C13 C9 C11 C1 -176.8(2) . . . . ?
C15 C9 C11 C1 4.7(3) . . . . ?
C2 C1 C11 C9 178.29(19) . . . . ?
C2 C1 C11 C12 -0.9(3) . . . . ?
C14 N10 C12 C4 175.62(17) . . . . ?
C18 N10 C12 C4 -5.8(3) . . . . ?
C14 N10 C12 C11 -4.4(3) . . . . ?
C18 N10 C12 C11 174.19(18) . . . . ?
C3 C4 C12 N10 179.7(2) . . . . ?
C3 C4 C12 C11 -0.3(3) . . . . ?
C9 C11 C12 N10 2.0(3) . . . . ?
C1 C11 C12 N10 -178.81(19) . . . . ?
C9 C11 C12 C4 -178.09(18) . . . . ?
C1 C11 C12 C4 1.1(3) . . . . ?
C11 C9 C13 C14 -4.4(3) . . . . ?
C15 C9 C13 C14 174.13(17) . . . . ?
C11 C9 C13 C8 175.68(17) . . . . ?
C15 C9 C13 C8 -5.8(3) . . . . ?
C7 C8 C13 C9 179.5(2) . . . . ?
C7 C8 C13 C14 -0.4(3) . . . . ?
C12 N10 C14 C5 -176.88(19) . . . . ?
C18 N10 C14 C5 4.5(3) . . . . ?
C12 N10 C14 C13 2.4(3) . . . . ?
C18 N10 C14 C13 -176.16(17) . . . . ?
C6 C5 C14 N10 177.67(19) . . . . ?
C6 C5 C14 C13 -1.6(3) . . . . ?
C9 C13 C14 N10 2.0(3) . . . . ?
C8 C13 C14 N10 -178.04(17) . . . . ?
C9 C13 C14 C5 -178.66(19) . . . . ?
C8 C13 C14 C5 1.3(3) . . . . ?
C13 C9 C15 O17 -88.2(2) . . . . ?
C11 C9 C15 O17 90.3(2) . . . . ?
C13 C9 C15 O16 92.5(2) . . . . ?
C11 C9 C15 O16 -89.0(2) . . . . ?
C23 S19 O20 F24 -102(21) 2_676 . . 2_676 ?
F25 S19 O20 F24 -97(4) 2_676 . . 2_676 ?
F26 S19 O20 F24 156(4) 2_676 . . 2_676 ?
O22 S19 O20 F24 143(4) . . . 2_676 ?
O21 S19 O20 F24 -91(4) . . . 2_676 ?
S19 S19 O20 F24 31(4) 2_676 . . 2_676 ?
C23 S19 O20 F24 33(4) . . . 2_676 ?
F25 S19 O20 C23 5(20) 2_676 . . 2_676 ?
F26 S19 O20 C23 -103(20) 2_676 . . 2_676 ?
F24 S19 O20 C23 102(21) 2_676 . . 2_676 ?
O22 S19 O20 C23 -115(20) . . . 2_676 ?
O21 S19 O20 C23 11(20) . . . 2_676 ?
S19 S19 O20 C23 133(20) 2_676 . . 2_676 ?
C23 S19 O20 C23 135(20) . . . 2_676 ?
C23 S19 O21 F25 -26(13) 2_676 . . 2_676 ?
F26 S19 O21 F25 76(5) 2_676 . . 2_676 ?
F24 S19 O21 F25 -47(5) 2_676 . . 2_676 ?
O20 S19 O21 F25 -33(5) . . . 2_676 ?
O22 S19 O21 F25 89(5) . . . 2_676 ?
S19 S19 O21 F25 -159(5) 2_676 . . 2_676 ?
C23 S19 O21 F25 -162(5) . . . 2_676 ?
F25 S19 O21 C23 26(13) 2_676 . . 2_676 ?
F26 S19 O21 C23 102(12) 2_676 . . 2_676 ?
F24 S19 O21 C23 -21(12) 2_676 . . 2_676 ?
O20 S19 O21 C23 -7(12) . . . 2_676 ?
O22 S19 O21 C23 115(12) . . . 2_676 ?
S19 S19 O21 C23 -133(12) 2_676 . . 2_676 ?
C23 S19 O21 C23 -136(12) . . . 2_676 ?
C23 S19 O22 F26 25(16) 2_676 . . 2_676 ?
F25 S19 O22 F26 -50(8) 2_676 . . 2_676 ?
F24 S19 O22 F26 72(7) 2_676 . . 2_676 ?
O20 S19 O22 F26 64(7) . . . 2_676 ?
O21 S19 O22 F26 -63(8) . . . 2_676 ?
S19 S19 O22 F26 -177(7) 2_676 . . 2_676 ?
C23 S19 O22 F26 -176(7) . . . 2_676 ?
F25 S19 O22 C23 -75(15) 2_676 . . 2_676 ?
F26 S19 O22 C23 -25(16) 2_676 . . 2_676 ?
F24 S19 O22 C23 47(15) 2_676 . . 2_676 ?
O20 S19 O22 C23 39(15) . . . 2_676 ?
O21 S19 O22 C23 -88(15) . . . 2_676 ?
S19 S19 O22 C23 158(15) 2_676 . . 2_676 ?
C23 S19 O22 C23 159(14) . . . 2_676 ?
C23 S19 C23 S19 0.00(4) 2_676 . . 2_676 ?
F25 S19 C23 S19 85(20) 2_676 . . 2_676 ?
F26 S19 C23 S19 -153(20) 2_676 . . 2_676 ?
F24 S19 C23 S19 -32(20) 2_676 . . 2_676 ?
O20 S19 C23 S19 -39(20) . . . 2_676 ?
O22 S19 C23 S19 -152(20) . . . 2_676 ?
O21 S19 C23 S19 89(20) . . . 2_676 ?
C23 S19 C23 F25 92(20) 2_676 . . . ?
F25 S19 C23 F25 176.7(10) 2_676 . . . ?
F26 S19 C23 F25 -61.5(18) 2_676 . . . ?
F24 S19 C23 F25 59.9(16) 2_676 . . . ?
O20 S19 C23 F25 52.5(16) . . . . ?
O22 S19 C23 F25 -60.4(16) . . . . ?
O21 S19 C23 F25 -179.4(16) . . . . ?
S19 S19 C23 F25 92(20) 2_676 . . . ?
C23 S19 C23 F24 -146(21) 2_676 . . . ?
F25 S19 C23 F24 -61.6(17) 2_676 . . . ?
F26 S19 C23 F24 60.2(17) 2_676 . . . ?
F24 S19 C23 F24 -178.4(10) 2_676 . . . ?
O20 S19 C23 F24 174.2(16) . . . . ?
O22 S19 C23 F24 61.3(16) . . . . ?
O21 S19 C23 F24 -57.7(14) . . . . ?
S19 S19 C23 F24 -146(21) 2_676 . . . ?
C23 S19 C23 O20 -139(21) 2_676 . . 2_676 ?
F25 S19 C23 O20 -53.9(18) 2_676 . . 2_676 ?
F26 S19 C23 O20 68.0(19) 2_676 . . 2_676 ?
F24 S19 C23 O20 -170.6(18) 2_676 . . 2_676 ?
O20 S19 C23 O20 -178.0(11) . . . 2_676 ?
O22 S19 C23 O20 69.1(18) . . . 2_676 ?
O21 S19 C23 O20 -49.9(16) . . . 2_676 ?
S19 S19 C23 O20 -139(21) 2_676 . . 2_676 ?
C23 S19 C23 F26 -25(19) 2_676 . . . ?
F25 S19 C23 F26 59.5(17) 2_676 . . . ?
F26 S19 C23 F26 -178.7(10) 2_676 . . . ?
F24 S19 C23 F26 -57.3(17) 2_676 . . . ?
O20 S19 C23 F26 -64.7(18) . . . . ?
O22 S19 C23 F26 -178(2) . . . . ?
O21 S19 C23 F26 63.4(17) . . . . ?
S19 S19 C23 F26 -25(19) 2_676 . . . ?
C23 S19 C23 O21 89(20) 2_676 . . 2_676 ?
F25 S19 C23 O21 173.3(14) 2_676 . . 2_676 ?
F26 S19 C23 O21 -64.9(15) 2_676 . . 2_676 ?
F24 S19 C23 O21 56.5(13) 2_676 . . 2_676 ?
O20 S19 C23 O21 49.1(13) . . . 2_676 ?
O22 S19 C23 O21 -63.8(14) . . . 2_676 ?
O21 S19 C23 O21 177.2(8) . . . 2_676 ?
S19 S19 C23 O21 89(20) 2_676 . . 2_676 ?
C23 S19 C23 O22 -26(19) 2_676 . . 2_676 ?
F25 S19 C23 O22 58.2(15) 2_676 . . 2_676 ?
F26 S19 C23 O22 -180(2) 2_676 . . 2_676 ?
F24 S19 C23 O22 -58.5(14) 2_676 . . 2_676 ?
O20 S19 C23 O22 -65.9(16) . . . 2_676 ?
O22 S19 C23 O22 -178.8(9) . . . 2_676 ?
O21 S19 C23 O22 62.2(14) . . . 2_676 ?
S19 S19 C23 O22 -26(19) 2_676 . . 2_676 ?
F25 S19 C23 C23 85(20) 2_676 . . 2_676 ?
F26 S19 C23 C23 -153(20) 2_676 . . 2_676 ?
F24 S19 C23 C23 -32(20) 2_676 . . 2_676 ?
O20 S19 C23 C23 -39(20) . . . 2_676 ?
O22 S19 C23 C23 -152(20) . . . 2_676 ?
O21 S19 C23 C23 89(20) . . . 2_676 ?
S19 S19 C23 C23 0.0(3) 2_676 . . 2_676 ?
S19 C23 F24 O20 117(21) 2_676 . . 2_676 ?
F25 C23 F24 O20 -88(4) . . . 2_676 ?
F26 C23 F24 O20 30(5) . . . 2_676 ?
O21 C23 F24 O20 -97(4) 2_676 . . 2_676 ?
O22 C23 F24 O20 45(5) 2_676 . . 2_676 ?
S19 C23 F24 O20 149(4) . . . 2_676 ?
C23 C23 F24 O20 148(4) 2_676 . . 2_676 ?
F25 C23 F24 S19 155(21) . . . 2_676 ?
O20 C23 F24 S19 -117(21) 2_676 . . 2_676 ?
F26 C23 F24 S19 -87(20) . . . 2_676 ?
O21 C23 F24 S19 146(21) 2_676 . . 2_676 ?
O22 C23 F24 S19 -72(20) 2_676 . . 2_676 ?
S19 C23 F24 S19 32(19) . . . 2_676 ?
C23 C23 F24 S19 31(19) 2_676 . . 2_676 ?
S19 C23 F25 O21 29(15) 2_676 . . 2_676 ?
F24 C23 F25 O21 -133(5) . . . 2_676 ?
O20 C23 F25 O21 -148(5) 2_676 . . 2_676 ?
F26 C23 F25 O21 103(5) . . . 2_676 ?
O22 C23 F25 O21 92(5) 2_676 . . 2_676 ?
S19 C23 F25 O21 -17(5) . . . 2_676 ?
C23 C23 F25 O21 -15(6) 2_676 . . 2_676 ?
F24 C23 F25 S19 -162(14) . . . 2_676 ?
O20 C23 F25 S19 -177(14) 2_676 . . 2_676 ?
F26 C23 F25 S19 75(13) . . . 2_676 ?
O21 C23 F25 S19 -29(15) 2_676 . . 2_676 ?
O22 C23 F25 S19 63(13) 2_676 . . 2_676 ?
S19 C23 F25 S19 -46(13) . . . 2_676 ?
C23 C23 F25 S19 -44(12) 2_676 . . 2_676 ?
S19 C23 F26 O22 -23(15) 2_676 . . 2_676 ?
F25 C23 F26 O22 -128(7) . . . 2_676 ?
F24 C23 F26 O22 109(7) . . . 2_676 ?
O20 C23 F26 O22 116(7) 2_676 . . 2_676 ?
O21 C23 F26 O22 -117(7) 2_676 . . 2_676 ?
S19 C23 F26 O22 -5(8) . . . 2_676 ?
C23 C23 F26 O22 -6(8) 2_676 . . 2_676 ?
F25 C23 F26 S19 -105(14) . . . 2_676 ?
F24 C23 F26 S19 132(15) . . . 2_676 ?
O20 C23 F26 S19 139(14) 2_676 . . 2_676 ?
O21 C23 F26 S19 -94(14) 2_676 . . 2_676 ?
O22 C23 F26 S19 23(15) 2_676 . . 2_676 ?
S19 C23 F26 S19 18(13) . . . 2_676 ?
C23 C23 F26 S19 17(12) 2_676 . . 2_676 ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.128
_refine_diff_density_rms         0.037
####################################################################### 
# 
# 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_Global
_database_code_depnum_ccdc_archive 'CCDC 981472'
_audit_update_record             
;
2014-01-14 deposited with the CCDC.
2016-06-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'Hydrogen bis(9-carboxy-10-methylacridinium) chloride  dihydrate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H23 N2 O4, Cl, 4(H2 O)'
_chemical_formula_sum            'C30 H31 Cl N2 O8'

_chemical_formula_weight         583.02

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'
O O 0.0106 0.0060 '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'
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   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   9.4378(4)
_cell_length_b                   7.0489(3)
_cell_length_c                   21.1972(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.158(4)
_cell_angle_gamma                90.00
_cell_volume                     1399.17(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    3300
_cell_measurement_theta_min      3.3994
_cell_measurement_theta_max      29.1636

_exptl_crystal_description       needle
_exptl_crystal_colour            light-orange
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             612
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_T_min  0.53601
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;


_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      110(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  'Oxford Diffraction Ruby CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.4002
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8760
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_sigmaI/netI    0.0340
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.48
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2454
_reflns_number_gt                2093
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'CrysAlis CCD,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)'
_computing_cell_refinement       
'CrysAlis RED,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)'
_computing_data_reduction        
'CrysAlis RED,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 and PLATON (Spek, 2009)'

_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)+(0.1449P)²+0.9406P] 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         2454
_refine_ls_number_parameters     204
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0773
_refine_ls_R_factor_gt           0.0684
_refine_ls_wR_factor_ref         0.2259
_refine_ls_wR_factor_gt          0.2128
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_restrained_S_all      1.109
_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
C1 C 0.5940(3) 0.2689(4) 0.41837(12) 0.0252(6) Uani 1 1 d . . .
H1 H 0.6864 0.2957 0.4072 0.030 Uiso 1 1 calc R . .
C2 C 0.4849(3) 0.2354(4) 0.37172(13) 0.0288(6) Uani 1 1 d . . .
H2 H 0.5004 0.2392 0.3283 0.035 Uiso 1 1 calc R . .
C3 C 0.3476(3) 0.1946(4) 0.38863(13) 0.0283(6) Uani 1 1 d . . .
H3 H 0.2718 0.1679 0.3560 0.034 Uiso 1 1 calc R . .
C4 C 0.3209(3) 0.1924(3) 0.45060(13) 0.0262(6) Uani 1 1 d . . .
H4 H 0.2274 0.1658 0.4604 0.031 Uiso 1 1 calc R . .
C5 C 0.4930(3) 0.2770(4) 0.67484(13) 0.0309(7) Uani 1 1 d . . .
H5 H 0.3996 0.2560 0.6857 0.037 Uiso 1 1 calc R . .
C6 C 0.6035(3) 0.3145(5) 0.72136(14) 0.0375(7) Uani 1 1 d . . .
H6 H 0.5853 0.3197 0.7644 0.045 Uiso 1 1 calc R . .
C7 C 0.7438(3) 0.3456(5) 0.70705(14) 0.0382(7) Uani 1 1 d . . .
H7 H 0.8187 0.3712 0.7402 0.046 Uiso 1 1 calc R . .
C8 C 0.7712(3) 0.3389(4) 0.64575(13) 0.0311(7) Uani 1 1 d . . .
H8 H 0.8657 0.3596 0.6362 0.037 Uiso 1 1 calc R . .
C9 C 0.6848(3) 0.2951(3) 0.53199(12) 0.0221(6) Uani 1 1 d . . .
N10 N 0.4100(2) 0.2303(3) 0.56280(10) 0.0227(5) Uani 1 1 d . . .
C11 C 0.5728(3) 0.2648(3) 0.48376(12) 0.0217(6) Uani 1 1 d . . .
C12 C 0.4324(3) 0.2297(3) 0.50020(12) 0.0214(6) Uani 1 1 d . . .
C13 C 0.6601(3) 0.3014(4) 0.59566(12) 0.0242(6) Uani 1 1 d . . .
C14 C 0.5185(3) 0.2696(4) 0.61046(12) 0.0236(6) Uani 1 1 d . . .
C15 C 0.8364(3) 0.3130(4) 0.51584(12) 0.0242(6) Uani 1 1 d . . .
O16 O 0.8764(2) 0.4848(3) 0.51021(10) 0.0360(6) Uani 1 1 d . . .
H16 H 1.0000 0.5000 0.5000 0.047(13) Uiso 1 2 d S . .
O17 O 0.9046(2) 0.1705(3) 0.50967(10) 0.0362(6) Uani 1 1 d . . .
C18 C 0.2671(3) 0.1904(4) 0.58154(13) 0.0299(7) Uani 1 1 d . . .
H18A H 0.2043 0.1423 0.5447 0.045 Uiso 1 1 calc R . .
H18B H 0.2268 0.3073 0.5969 0.045 Uiso 1 1 calc R . .
H18C H 0.2756 0.0950 0.6155 0.045 Uiso 1 1 calc R . .
Cl1 Cl 0.85194(13) 0.41617(18) 0.31941(6) 0.0294(4) Uani 0.50 1 d P . .
O1W O 0.8938(3) 0.8065(4) 0.27688(13) 0.0573(7) Uani 1 1 d D . .
H1W H 0.916(5) 0.896(4) 0.3002(19) 0.086 Uiso 1 1 d D . .
H2W H 0.886(6) 0.698(3) 0.290(2) 0.086 Uiso 1 1 d D . .
O2W O 0.9946(3) 0.0744(6) 0.37066(12) 0.0718(10) Uani 1 1 d D . .
H3W H 1.016(6) 0.031(6) 0.4091(13) 0.108 Uiso 1 1 d D . .
H4W H 0.999(6) 0.199(3) 0.376(2) 0.108 Uiso 1 1 d 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
C1 C2 1.357(4) . ?
C1 C11 1.425(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.417(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.368(4) . ?
C3 H3 0.9500 . ?
C4 C12 1.416(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.368(4) . ?
C5 C14 1.416(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.412(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.357(4) . ?
C7 H7 0.9500 . ?
C8 C13 1.422(4) . ?
C8 H8 0.9500 . ?
C9 C11 1.393(4) . ?
C9 C13 1.399(4) . ?
C9 C15 1.517(3) . ?
N10 C12 1.369(3) . ?
N10 C14 1.374(3) . ?
N10 C18 1.480(3) . ?
C11 C12 1.433(4) . ?
C13 C14 1.427(4) . ?
C15 O17 1.209(3) . ?
C15 O16 1.278(3) . ?
O16 H16 1.2177(18) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
O1W H1W 0.812(18) . ?
O1W H2W 0.823(19) . ?
O2W H3W 0.870(19) . ?
O2W H4W 0.885(19) . ?

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
C2 C1 C11 121.3(2) . . ?
C2 C1 H1 119.4 . . ?
C11 C1 H1 119.4 . . ?
C1 C2 C3 119.1(2) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C4 C3 C2 121.9(2) . . ?
C4 C3 H3 119.0 . . ?
C2 C3 H3 119.0 . . ?
C3 C4 C12 120.1(2) . . ?
C3 C4 H4 119.9 . . ?
C12 C4 H4 119.9 . . ?
C6 C5 C14 119.7(2) . . ?
C6 C5 H5 120.1 . . ?
C14 C5 H5 120.1 . . ?
C5 C6 C7 121.7(3) . . ?
C5 C6 H6 119.1 . . ?
C7 C6 H6 119.1 . . ?
C8 C7 C6 119.7(3) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C7 C8 C13 120.7(3) . . ?
C7 C8 H8 119.6 . . ?
C13 C8 H8 119.6 . . ?
C11 C9 C13 120.7(2) . . ?
C11 C9 C15 119.9(2) . . ?
C13 C9 C15 119.4(2) . . ?
C12 N10 C14 121.5(2) . . ?
C12 N10 C18 121.0(2) . . ?
C14 N10 C18 117.5(2) . . ?
C9 C11 C1 121.7(2) . . ?
C9 C11 C12 119.2(2) . . ?
C1 C11 C12 119.1(2) . . ?
N10 C12 C4 122.0(2) . . ?
N10 C12 C11 119.6(2) . . ?
C4 C12 C11 118.4(2) . . ?
C9 C13 C8 122.0(2) . . ?
C9 C13 C14 118.7(2) . . ?
C8 C13 C14 119.3(2) . . ?
N10 C14 C5 121.0(2) . . ?
N10 C14 C13 120.1(2) . . ?
C5 C14 C13 118.8(2) . . ?
O17 C15 O16 127.6(2) . . ?
O17 C15 C9 119.0(2) . . ?
O16 C15 C9 113.4(2) . . ?
C15 O16 H16 113.62(19) . . ?
N10 C18 H18A 109.5 . . ?
N10 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N10 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
H1W O1W H2W 123(4) . . ?
H3W O2W H4W 103(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 C1 C2 C3 -0.3(4) . . . . ?
C1 C2 C3 C4 1.6(4) . . . . ?
C2 C3 C4 C12 -0.6(4) . . . . ?
C14 C5 C6 C7 -0.3(4) . . . . ?
C5 C6 C7 C8 0.1(5) . . . . ?
C6 C7 C8 C13 0.2(5) . . . . ?
C13 C9 C11 C1 176.3(2) . . . . ?
C15 C9 C11 C1 -6.5(4) . . . . ?
C13 C9 C11 C12 -3.3(3) . . . . ?
C15 C9 C11 C12 174.0(2) . . . . ?
C2 C1 C11 C9 178.7(2) . . . . ?
C2 C1 C11 C12 -1.8(4) . . . . ?
C14 N10 C12 C4 -179.0(2) . . . . ?
C18 N10 C12 C4 0.4(3) . . . . ?
C14 N10 C12 C11 2.0(3) . . . . ?
C18 N10 C12 C11 -178.6(2) . . . . ?
C3 C4 C12 N10 179.5(2) . . . . ?
C3 C4 C12 C11 -1.5(4) . . . . ?
C9 C11 C12 N10 1.3(3) . . . . ?
C1 C11 C12 N10 -178.3(2) . . . . ?
C9 C11 C12 C4 -177.8(2) . . . . ?
C1 C11 C12 C4 2.7(3) . . . . ?
C11 C9 C13 C8 -177.7(2) . . . . ?
C15 C9 C13 C8 5.1(4) . . . . ?
C11 C9 C13 C14 2.1(4) . . . . ?
C15 C9 C13 C14 -175.2(2) . . . . ?
C7 C8 C13 C9 179.5(3) . . . . ?
C7 C8 C13 C14 -0.3(4) . . . . ?
C12 N10 C14 C5 177.5(2) . . . . ?
C18 N10 C14 C5 -1.9(4) . . . . ?
C12 N10 C14 C13 -3.2(4) . . . . ?
C18 N10 C14 C13 177.4(2) . . . . ?
C6 C5 C14 N10 179.3(3) . . . . ?
C6 C5 C14 C13 0.1(4) . . . . ?
C9 C13 C14 N10 1.2(4) . . . . ?
C8 C13 C14 N10 -179.1(2) . . . . ?
C9 C13 C14 C5 -179.6(2) . . . . ?
C8 C13 C14 C5 0.2(4) . . . . ?
C11 C9 C15 O17 -83.7(3) . . . . ?
C13 C9 C15 O17 93.6(3) . . . . ?
C11 C9 C15 O16 96.1(3) . . . . ?
C13 C9 C15 O16 -86.6(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         1.163
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.100

