# Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2005


data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182

_publ_contact_author_name        'Dr Norimitsu Tohnai'
_publ_contact_author_address     
;
Department of Material and Life Science
Graduate School of Engineering
Osaka University
2-1 Yamadaoka, Suita, Osaka 565-0871 (Japan)
;
_publ_contact_author_email       tohnai@molrec.mls.eng.osaka-u.ac.jp
_publ_contact_author_phone       '+81-6-6879-7406 '
_publ_contact_author_fax         +81-6-6879-7404
loop_
_publ_author_name
_publ_author_address
Y.Mizobe
;Department of Material and Life Science
Graduate School of Engineering
Osaka University
2-1 Yamadaoka, Suita, Osaka 565-0871 (Japan)
;
N.Tohnai
;Department of Material and Life Science
Graduate School of Engineering
Osaka University
2-1 Yamadaoka, Suita, Osaka 565-0871 (Japan)
;
M.Miyata
;Department of Material and Life Science
Graduate School of Engineering
Osaka University
2-1 Yamadaoka, Suita, Osaka 565-0871 (Japan)
;
Y.Hasegawa
;Department of Material and Life Science
Graduate School of Engineering
Osaka University
2-1 Yamadaoka, Suita, Osaka 565-0871 (Japan)
;

_publ_section_title              
;
Tunable solid-state fluorescence system consisted of
organic salts of anthracene-2,6-disulfnic acid with primary amines
;

_publ_section_references         
;
ENTER OTHER REFERENCES
Molecular Structure Corporation, Rigaku Corporation. (1999). teXsan.
Single Crystal Structure Analysis Software. Version 1.10.
MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA.
Rigaku, 3-9-12 Akishima, Tokyo, Japan.
;

#------------------------------------------------------------------------------

data_ads_me
_database_code_depnum_ccdc_archive 'CCDC 243059'

_audit_creation_date             'Mon Jan 17 16:35:57 2005'
_audit_creation_method           'by teXsan'
_audit_update_record             ?

#------------------------------------------------------------------------------
# CHEMICAL DATA
_chemical_formula_sum            'C8 H10 N O3 S '
_chemical_name_common            'methylammonium anthracene-2,6-disulfonate'

_chemical_formula_moiety         ?
_chemical_formula_weight         200.23
_chemical_melting_point          ?
#------------------------------------------------------------------------------
# CRYSTAL DATA
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
1/2-x,1/2+y,-z
-x,-y,-z
1/2+x,1/2-y,z
_cell_length_a                   12.028(9)
_cell_length_b                   5.654(4)
_cell_length_c                   12.89(1)
_cell_angle_alpha                90
_cell_angle_beta                 99.20(6)
_cell_angle_gamma                90
_cell_volume                     865(1)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1699
_cell_measurement_theta_min      7.4
_cell_measurement_theta_max      66.9
_cell_measurement_temperature    93.2
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.200
_exptl_crystal_size_rad          ?
_exptl_crystal_density_diffrn    1.537
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_absorpt_coefficient_mu    3.136
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Higashi, 1995)'
_exptl_absorpt_correction_T_min  0.218
_exptl_absorpt_correction_T_max  0.534
#------------------------------------------------------------------------------
# EXPERIMENTAL DATA
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5419
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID Imaging Plate'
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7029
_diffrn_reflns_av_R_equivalents  0.077
_diffrn_reflns_theta_max         68.22
_diffrn_measured_fraction_theta_max 0.9595
_diffrn_reflns_theta_full        68.22
_diffrn_measured_fraction_theta_full 0.9595
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
#------------------------------------------------------------------------------
# REFINEMENT DATA
_refine_special_details          
;
Refinement using reflections with F^2^ > -10.0 sigma(F^2^). The weighted
R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are
based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only
for calculating R-factor (gt).
;
_reflns_number_total             1519
_reflns_number_gt                1417
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0590
_refine_ls_wR_factor_ref         0.2224
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_reflns         1519
_refine_ls_number_parameters     118
_refine_ls_goodness_of_fit_ref   1.924
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[\s^2^(Fo^2^) + (0.09000(Max(Fo^2^,0) + 2Fc^2^)/3)^2^]'
_refine_ls_shift/su_max          0.0003
_refine_diff_density_max         1.08
_refine_diff_density_min         -0.84
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.018 0.009
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
H H 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
O O 0.049 0.032
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
N N 0.031 0.018
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
S S 0.333 0.557
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
#------------------------------------------------------------------------------
# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S(1) S 0.85531(6) 0.1236(1) 0.81784(5) 0.0148(3) Uani 1.00 d . . .
O(1) O 0.9698(2) 0.1208(4) 0.7882(2) 0.0200(6) Uani 1.00 d . . .
O(2) O 0.8461(2) -0.0515(4) 0.8982(2) 0.0185(6) Uani 1.00 d . . .
O(3) O 0.8167(2) 0.3528(4) 0.8452(2) 0.0214(6) Uani 1.00 d . . .
N(1) N 0.6404(3) -0.3367(5) 0.9035(2) 0.0183(7) Uani 1.00 d . . .
C(1) C 0.7578(3) 0.0287(6) 0.7072(2) 0.0146(7) Uani 1.00 d . . .
C(2) C 0.6626(3) 0.1625(6) 0.6704(3) 0.0185(8) Uani 1.00 d . . .
C(3) C 0.7784(3) -0.1908(6) 0.6614(3) 0.0182(8) Uani 1.00 d . . .
C(4) C 0.5797(3) 0.0830(6) 0.5848(2) 0.0168(8) Uani 1.00 d . . .
C(5) C 0.7016(3) -0.2698(6) 0.5786(2) 0.0174(7) Uani 1.00 d . . .
C(6) C 0.5998(3) -0.1358(5) 0.5372(2) 0.0157(8) Uani 1.00 d . . .
C(7) C 0.5198(3) -0.2149(6) 0.4537(2) 0.0161(8) Uani 1.00 d . . .
C(8) C 0.5738(3) -0.1123(6) 0.8966(3) 0.0222(9) Uani 1.00 d . . .
H(1) H 0.8524 -0.2912 0.6936 0.0266 Uiso 1.00 calc . . .
H(2) H 0.6478 0.3010 0.6987 0.0266 Uiso 1.00 calc . . .
H(3) H 0.7169 -0.4051 0.5557 0.0266 Uiso 1.00 calc . . .
H(4) H 0.5381 -0.3687 0.4220 0.0266 Uiso 1.00 calc . . .
H(5) H 0.7111 -0.3337 0.8949 0.0266 Uiso 1.00 calc . . .
H(6) H 0.6495 -0.3840 0.9733 0.0266 Uiso 1.00 calc . . .
H(7) H 0.6087 -0.4474 0.8675 0.0266 Uiso 1.00 calc . . .
H(8) H 0.5701 -0.0459 0.8355 0.0266 Uiso 1.00 calc . . .
H(9) H 0.6143 -0.0236 0.9510 0.0266 Uiso 1.00 calc . . .
H(10) H 0.4941 -0.1289 0.9283 0.0266 Uiso 1.00 calc . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
S(1) 0.0163(6) 0.0163(6) 0.0111(6) -0.0004(3) 0.0002(4) -0.0003(2)
O(1) 0.017(1) 0.026(1) 0.017(1) -0.0003(9) 0.0032(10) 0.0020(8)
O(2) 0.026(1) 0.018(1) 0.011(1) -0.0012(9) 0.0015(9) -0.0003(9)
O(3) 0.028(1) 0.017(1) 0.018(1) 0.0013(9) -0.002(1) -0.0045(9)
N(1) 0.022(1) 0.017(1) 0.016(1) 0.002(1) 0.003(1) 0.000(1)
C(1) 0.016(1) 0.018(2) 0.010(1) -0.002(1) 0.000(1) -0.001(1)
C(2) 0.029(2) 0.015(1) 0.013(1) -0.003(1) 0.007(1) -0.003(1)
C(3) 0.021(2) 0.017(2) 0.016(1) 0.001(1) 0.002(1) 0.001(1)
C(4) 0.024(2) 0.015(1) 0.011(1) -0.002(1) 0.003(1) 0.000(1)
C(5) 0.019(2) 0.019(1) 0.015(1) 0.001(1) 0.004(1) -0.001(1)
C(6) 0.024(2) 0.015(2) 0.008(1) 0.001(1) 0.003(1) 0.002(1)
C(7) 0.017(2) 0.017(2) 0.014(1) -0.001(1) 0.003(1) 0.001(1)
C(8) 0.026(2) 0.018(2) 0.022(2) 0.002(1) 0.003(1) 0.003(1)
#------------------------------------------------------------------------------
_computing_data_collection       PROCESS-AUTO
_computing_cell_refinement       PROCESS-AUTO
_computing_data_reduction        'teXsan Ver. 1.10'
_computing_structure_solution    SIR92
_computing_structure_refinement  'teXsan Ver. 1.10'
_computing_publication_material  'teXsan Ver. 1.10'
_computing_molecular_graphics    ?
#------------------------------------------------------------------------------
_geom_special_details            
;
?
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S(1) O(1) 1.486(3) . . yes
S(1) O(2) 1.449(2) . . yes
S(1) O(3) 1.439(2) . . yes
S(1) C(1) 1.778(3) . . yes
N(1) C(8) 1.496(4) . . yes
C(1) C(2) 1.391(5) . . yes
C(1) C(3) 1.413(4) . . yes
C(2) C(4) 1.436(5) . . yes
C(3) C(5) 1.370(5) . . yes
C(4) C(6) 1.419(5) . . yes
C(4) C(7) 1.431(5) . 3_656 yes
C(5) C(6) 1.466(5) . . yes
C(6) C(7) 1.396(5) . . yes
#------------------------------------------------------------------------------
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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O(1) S(1) O(2) 110.8(1) . 1_555 1_555 yes
O(1) S(1) O(3) 114.9(1) . 1_555 1_555 yes
O(1) S(1) C(1) 108.1(1) . 1_555 1_555 yes
O(2) S(1) O(3) 112.1(1) . 1_555 1_555 yes
O(2) S(1) C(1) 104.5(1) . 1_555 1_555 yes
O(3) S(1) C(1) 105.7(2) . 1_555 1_555 yes
S(1) C(1) C(2) 120.7(2) . 1_555 1_555 yes
S(1) C(1) C(3) 117.6(2) . 1_555 1_555 yes
C(2) C(1) C(3) 121.7(3) . 1_555 1_555 yes
C(1) C(2) C(4) 121.6(3) . 1_555 1_555 yes
C(1) C(3) C(5) 118.0(3) . 1_555 1_555 yes
C(2) C(4) C(6) 117.4(3) . 1_555 1_555 yes
C(2) C(4) C(7) 123.0(3) . 1_555 3_656 yes
C(6) C(4) C(7) 119.7(3) . 1_555 3_656 yes
C(3) C(5) C(6) 122.4(3) . 1_555 1_555 yes
C(4) C(6) C(5) 118.9(3) . 1_555 1_555 yes
C(4) C(6) C(7) 117.9(3) . 1_555 1_555 yes
C(5) C(6) C(7) 123.2(3) . 1_555 1_555 yes
C(4) C(7) C(6) 122.4(3) . 3_656 1_555 yes
#------------------------------------------------------------------------------
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
S(1) C(1) C(2) C(4) -176.6(3) 1_555 1_555 1_555 1_555 yes
S(1) C(1) C(3) C(5) 177.6(2) 1_555 1_555 1_555 1_555 yes
O(1) S(1) C(1) C(2) -128.2(3) 1_555 1_555 1_555 1_555 yes
O(1) S(1) C(1) C(3) 54.3(3) 1_555 1_555 1_555 1_555 yes
O(2) S(1) C(1) C(2) 113.7(3) 1_555 1_555 1_555 1_555 yes
O(2) S(1) C(1) C(3) -63.8(3) 1_555 1_555 1_555 1_555 yes
O(3) S(1) C(1) C(2) -4.7(3) 1_555 1_555 1_555 1_555 yes
O(3) S(1) C(1) C(3) 177.8(2) 1_555 1_555 1_555 1_555 yes
C(1) C(2) C(4) C(6) -1.5(5) 1_555 1_555 1_555 1_555 yes
C(1) C(2) C(4) C(7) 179.0(3) 1_555 1_555 1_555 3_656 yes
C(1) C(3) C(5) C(6) -0.3(5) 1_555 1_555 1_555 1_555 yes
C(2) C(1) C(3) C(5) 0.1(5) 1_555 1_555 1_555 1_555 yes
C(2) C(4) C(6) C(5) 1.2(5) 1_555 1_555 1_555 1_555 yes
C(2) C(4) C(6) C(7) -179.9(3) 1_555 1_555 1_555 1_555 yes
C(2) C(4) C(7) C(6) 179.9(3) 1_555 1_555 3_656 3_656 yes
C(3) C(1) C(2) C(4) 0.8(5) 1_555 1_555 1_555 1_555 yes
C(3) C(5) C(6) C(4) -0.4(5) 1_555 1_555 1_555 1_555 yes
C(3) C(5) C(6) C(7) -179.2(3) 1_555 1_555 1_555 1_555 yes
C(4) C(7) C(6) C(5) -179.2(3) 1_555 3_656 3_656 3_656 yes
C(5) C(6) C(4) C(7) -179.3(3) 1_555 1_555 1_555 3_656 yes
#------------------------------------------------------------------------------
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
S(1) N(1) 3.591(3) . 2_657 ?
O(1) N(1) 2.833(4) . 4_545 ?
O(1) C(2) 3.211(4) . 4_555 ?
O(1) C(8) 3.268(4) . 4_555 ?
O(1) C(7) 3.275(4) . 2_656 ?
O(1) C(8) 3.350(4) . 4_545 ?
O(1) C(4) 3.540(4) . 4_555 ?
O(2) N(1) 2.811(4) . 2_657 ?
O(2) N(1) 2.963(4) . . ?
O(2) C(8) 3.290(5) . . ?
O(2) C(8) 3.336(5) . 4_545 ?
O(2) O(3) 3.444(3) . 1_545 ?
O(2) N(1) 3.586(5) . 4_545 ?
O(3) N(1) 2.940(4) . 1_565 ?
O(3) N(1) 3.373(4) . 2_657 ?
O(3) C(8) 3.384(4) . 2_657 ?
O(3) C(8) 3.392(5) . 4_555 ?
O(3) C(3) 3.482(4) . 1_565 ?
C(2) C(5) 3.478(5) . 1_565 ?
C(7) C(7) 3.497(6) . 3_646 ?
#------------------------------------------------------------------------------
#------------------------------------------------------------------------------
data_ads_et
_database_code_depnum_ccdc_archive 'CCDC 243060'

_audit_creation_date             'Tue Jan 18 21:55:17 2005'
_audit_creation_method           'by teXsan'
_audit_update_record             ?

#------------------------------------------------------------------------------
# CHEMICAL DATA
_chemical_formula_sum            'C9 H12 N O3 S'
_chemical_name_common            'ethylammonium anthracene-2,6-disulfonate'

_chemical_formula_moiety         ?
_chemical_formula_weight         214.26
_chemical_melting_point          ?
#------------------------------------------------------------------------------
# CRYSTAL DATA
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_Int_Tables_number      15
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,y,1/2-z
-x,-y,-z
x,-y,1/2+z
1/2+x,1/2+y,z
1/2-x,1/2+y,1/2-z
1/2-x,1/2-y,-z
1/2+x,1/2-y,1/2+z
_cell_length_a                   35.574(5)
_cell_length_b                   7.465(1)
_cell_length_c                   7.659(1)
_cell_angle_alpha                90
_cell_angle_beta                 99.48(1)
_cell_angle_gamma                90
_cell_volume                     2006.3(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7856
_cell_measurement_theta_min      5.0
_cell_measurement_theta_max      68.3
_cell_measurement_temperature    213.2
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.100
_exptl_crystal_size_rad          ?
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_absorpt_coefficient_mu    2.741
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Higashi, 1995)'
_exptl_absorpt_correction_T_min  0.385
_exptl_absorpt_correction_T_max  0.760
_diffrn_radiation_probe          ?
#------------------------------------------------------------------------------
# EXPERIMENTAL DATA
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5419
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID Imaging Plate'
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8504
_diffrn_reflns_av_R_equivalents  0.091
_diffrn_reflns_theta_max         68.24
_diffrn_measured_fraction_theta_max 0.9710
_diffrn_reflns_theta_full        68.24
_diffrn_measured_fraction_theta_full 0.9710
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
#------------------------------------------------------------------------------
# REFINEMENT DATA
_refine_special_details          
;
Refinement using reflections with F^2^ > -10.0 sigma(F^2^). The weighted
R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are
based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only
for calculating R-factor (gt).
;
_reflns_number_total             1776
_reflns_number_gt                1275
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.1064
_refine_ls_wR_factor_ref         0.2950
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_reflns         1776
_refine_ls_number_parameters     127
_refine_ls_goodness_of_fit_ref   1.910
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[\s^2^(Fo^2^) + (0.07000(Max(Fo^2^,0) + 2Fc^2^)/3)^2^]'
_refine_ls_shift/su_max          0.0006
_refine_diff_density_max         1.21
_refine_diff_density_min         -1.04
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.018 0.009
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
H H 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
O O 0.049 0.032
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
N N 0.031 0.018
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
S S 0.333 0.557
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
#------------------------------------------------------------------------------
# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S(1) S 0.88906(5) 0.2541(2) -0.2079(2) 0.0325(4) Uani 1.00 d . . .
O(1) O 0.8971(1) 0.4216(6) -0.2888(7) 0.055(2) Uani 1.00 d . . .
O(2) O 0.9112(1) 0.2232(7) -0.0350(6) 0.051(1) Uani 1.00 d . . .
O(3) O 0.8908(1) 0.1092(6) -0.3320(6) 0.047(1) Uani 1.00 d . . .
N(1) N 0.9140(2) 0.7715(8) -0.1568(7) 0.043(2) Uani 1.00 d . . .
C(1) C 0.8398(2) 0.2669(8) -0.1844(9) 0.035(2) Uani 1.00 d . . .
C(2) C 0.8145(2) 0.3409(10) -0.3276(9) 0.047(2) Uani 1.00 d . . .
C(3) C 0.8283(2) 0.2094(9) -0.0300(9) 0.043(2) Uani 1.00 d . . .
C(4) C 0.7767(2) 0.3602(10) -0.3146(10) 0.048(2) Uani 1.00 d . . .
C(5) C 0.7885(2) 0.2287(7) -0.0162(8) 0.034(2) Uani 1.00 d . . .
C(6) C 0.7628(2) 0.3006(8) -0.1568(8) 0.037(2) Uani 1.00 d . . .
C(7) C 0.7758(2) 0.1740(9) 0.1413(9) 0.042(2) Uani 1.00 d . . .
C(8) C 0.9557(3) 0.763(2) -0.126(2) 0.116(5) Uani 1.00 d . . .
C(9) C 0.9767(5) 0.742(4) 0.001(2) 0.32(2) Uani 1.00 d . . .
H(1) H 0.8239 0.3803 -0.4321 0.0556 Uiso 1.00 calc . . .
H(2) H 0.8465 0.1574 0.0661 0.0494 Uiso 1.00 calc . . .
H(3) H 0.7591 0.4097 -0.4106 0.0559 Uiso 1.00 calc . . .
H(4) H 0.7969 0.1330 0.2542 0.0648 Uiso 1.00 calc . . .
H(5) H 0.9043 0.6542 -0.1373 0.0501 Uiso 1.00 calc . . .
H(6) H 0.9048 0.8036 -0.2776 0.0501 Uiso 1.00 calc . . .
H(7) H 0.9048 0.8539 -0.0810 0.0501 Uiso 1.00 calc . . .
H(8) H 0.9619 0.6859 -0.2115 0.1520 Uiso 1.00 calc . . .
H(9) H 0.9625 0.8854 -0.1545 0.1520 Uiso 1.00 calc . . .
H(10) H 1.0024 0.7438 -0.0210 0.3113 Uiso 1.00 calc . . .
H(11) H 0.9735 0.8132 0.0943 0.3113 Uiso 1.00 calc . . .
H(12) H 0.9728 0.6136 0.0376 0.3113 Uiso 1.00 calc . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
S(1) 0.0383(9) 0.0244(7) 0.0383(9) 0.0008(6) 0.0168(6) 0.0004(6)
O(1) 0.061(3) 0.036(3) 0.075(4) 0.004(2) 0.032(3) 0.023(2)
O(2) 0.048(3) 0.070(3) 0.036(3) 0.002(2) 0.011(2) 0.007(2)
O(3) 0.054(3) 0.042(3) 0.050(3) -0.001(2) 0.023(2) -0.018(2)
N(1) 0.042(3) 0.058(3) 0.033(3) 0.003(3) 0.013(2) 0.007(3)
C(1) 0.034(3) 0.035(3) 0.038(3) 0.003(3) 0.018(3) 0.004(3)
C(2) 0.049(4) 0.054(4) 0.040(4) 0.009(3) 0.016(3) 0.015(3)
C(3) 0.042(4) 0.043(4) 0.044(4) 0.002(3) 0.009(3) 0.005(3)
C(4) 0.048(4) 0.049(4) 0.047(4) 0.006(3) 0.010(3) 0.013(3)
C(5) 0.036(3) 0.029(3) 0.038(3) -0.004(2) 0.014(3) 0.001(2)
C(6) 0.044(4) 0.033(3) 0.040(4) 0.000(3) 0.019(3) -0.003(3)
C(7) 0.044(4) 0.033(3) 0.048(4) -0.001(3) 0.010(3) 0.006(3)
C(8) 0.043(5) 0.24(2) 0.070(6) 0.009(7) 0.014(5) -0.019(8)
C(9) 0.08(1) 0.79(8) 0.09(1) 0.03(2) 0.006(9) -0.08(2)
#------------------------------------------------------------------------------
_computing_data_collection       PROCESS-AUTO
_computing_cell_refinement       PROCESS-AUTO
_computing_data_reduction        'teXsan Ver. 1.10'
_computing_structure_solution    SIR92
_computing_structure_refinement  'teXsan Ver. 1.10'
_computing_publication_material  'teXsan Ver. 1.10'
_computing_molecular_graphics    ?
#------------------------------------------------------------------------------
_geom_special_details            
;
?
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S(1) O(1) 1.445(4) . . yes
S(1) O(2) 1.445(5) . . yes
S(1) O(3) 1.448(4) . . yes
S(1) C(1) 1.793(7) . . yes
N(1) C(8) 1.46(1) . . yes
C(1) C(2) 1.413(9) . . yes
C(1) C(3) 1.382(9) . . yes
C(2) C(4) 1.372(10) . . yes
C(3) C(5) 1.446(10) . . yes
C(4) C(6) 1.449(9) . . yes
C(5) C(6) 1.398(9) . . yes
C(5) C(7) 1.416(9) . . yes
C(6) C(7) 1.411(10) . 7_655 yes
C(8) C(9) 1.14(2) . . yes
#------------------------------------------------------------------------------
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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O(1) S(1) O(2) 114.5(3) . 1_555 1_555 yes
O(1) S(1) O(3) 109.4(3) . 1_555 1_555 yes
O(1) S(1) C(1) 105.2(3) . 1_555 1_555 yes
O(2) S(1) O(3) 114.0(3) . 1_555 1_555 yes
O(2) S(1) C(1) 108.1(3) . 1_555 1_555 yes
O(3) S(1) C(1) 104.7(3) . 1_555 1_555 yes
S(1) C(1) C(2) 116.8(5) . 1_555 1_555 yes
S(1) C(1) C(3) 120.1(5) . 1_555 1_555 yes
C(2) C(1) C(3) 123.0(6) . 1_555 1_555 yes
C(1) C(2) C(4) 119.5(6) . 1_555 1_555 yes
C(1) C(3) C(5) 117.6(6) . 1_555 1_555 yes
C(2) C(4) C(6) 120.0(6) . 1_555 1_555 yes
C(3) C(5) C(6) 120.3(6) . 1_555 1_555 yes
C(3) C(5) C(7) 119.2(6) . 1_555 1_555 yes
C(6) C(5) C(7) 120.5(6) . 1_555 1_555 yes
C(4) C(6) C(5) 119.5(6) . 1_555 1_555 yes
C(4) C(6) C(7) 119.9(6) . 1_555 7_655 yes
C(5) C(6) C(7) 120.5(6) . 1_555 7_655 yes
C(5) C(7) C(6) 119.0(6) . 1_555 7_655 yes
N(1) C(8) C(9) 130(1) . 1_555 1_555 yes
#------------------------------------------------------------------------------
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
S(1) C(1) C(2) C(4) -177.6(6) 1_555 1_555 1_555 1_555 yes
S(1) C(1) C(3) C(5) 177.9(4) 1_555 1_555 1_555 1_555 yes
O(1) S(1) C(1) C(2) 41.6(6) 1_555 1_555 1_555 1_555 yes
O(1) S(1) C(1) C(3) -137.1(5) 1_555 1_555 1_555 1_555 yes
O(2) S(1) C(1) C(2) 164.3(5) 1_555 1_555 1_555 1_555 yes
O(2) S(1) C(1) C(3) -14.3(6) 1_555 1_555 1_555 1_555 yes
O(3) S(1) C(1) C(2) -73.7(6) 1_555 1_555 1_555 1_555 yes
O(3) S(1) C(1) C(3) 107.6(6) 1_555 1_555 1_555 1_555 yes
C(1) C(2) C(4) C(6) -1(1) 1_555 1_555 1_555 1_555 yes
C(1) C(3) C(5) C(6) 1.0(9) 1_555 1_555 1_555 1_555 yes
C(1) C(3) C(5) C(7) -179.0(6) 1_555 1_555 1_555 1_555 yes
C(2) C(1) C(3) C(5) -0.6(10) 1_555 1_555 1_555 1_555 yes
C(2) C(4) C(6) C(5) 1(1) 1_555 1_555 1_555 1_555 yes
C(2) C(4) C(6) C(7) 177.9(7) 1_555 1_555 1_555 7_655 yes
C(3) C(1) C(2) C(4) 0(1) 1_555 1_555 1_555 1_555 yes
C(3) C(5) C(6) C(4) -1.7(9) 1_555 1_555 1_555 1_555 yes
C(3) C(5) C(6) C(7) -177.5(6) 1_555 1_555 1_555 7_655 yes
C(3) C(5) C(7) C(6) 177.6(6) 1_555 1_555 1_555 7_655 yes
C(4) C(6) C(5) C(7) 178.3(6) 1_555 1_555 1_555 1_555 yes
C(4) C(6) C(7) C(5) -178.2(6) 1_555 1_555 7_655 7_655 yes
#------------------------------------------------------------------------------
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O(1) N(1) 2.830(8) . . ?
O(1) N(1) 3.308(8) . 4_564 ?
O(1) O(2) 3.340(7) . 4_564 ?
O(1) C(8) 3.40(1) . . ?
O(2) N(1) 2.882(7) . 4_565 ?
O(2) O(3) 3.078(6) . 4_555 ?
O(2) C(8) 3.27(1) . 4_565 ?
O(2) N(1) 3.504(8) . 1_545 ?
O(3) N(1) 2.888(7) . 4_564 ?
O(3) N(1) 2.911(8) . 1_545 ?
O(3) C(3) 3.433(8) . 4_554 ?
C(2) C(5) 3.582(9) . 4_564 ?
C(4) C(5) 3.491(9) . 4_564 ?
C(4) C(7) 3.493(10) . 4_564 ?
C(4) C(4) 3.55(2) . 7_654 ?
C(4) C(6) 3.568(9) . 6_654 ?

#------------------------------------------------------------------------------
data_mizobe
_database_code_depnum_ccdc_archive 'CCDC 243061'

_audit_creation_date             'Mon Jan 17 16:38:01 2005'
_audit_creation_method           'by teXsan'
_audit_update_record             ?
#------------------------------------------------------------------------------
# CHEMICAL DATA
_chemical_formula_sum            'C12 H18 N O3 S '
_chemical_name_common            'n-amylammonium anthracene-2,6-disulfonate'

_chemical_formula_moiety         ?
_chemical_formula_weight         256.34
_chemical_melting_point          ?
#------------------------------------------------------------------------------
# CRYSTAL DATA
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_Int_Tables_number      2

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

_cell_length_a                   5.925(3)
_cell_length_b                   7.508(4)
_cell_length_c                   14.947(4)
_cell_angle_alpha                77.02(2)
_cell_angle_beta                 82.659(8)
_cell_angle_gamma                86.15(2)
_cell_volume                     642.1(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1861
_cell_measurement_theta_min      6.1
_cell_measurement_theta_max      66.9
_cell_measurement_temperature    213.2
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_crystal_size_rad          ?
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_absorpt_coefficient_mu    2.226
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(Higashi, 1999)'
_exptl_absorpt_correction_T_min  0.393
_exptl_absorpt_correction_T_max  0.800
#------------------------------------------------------------------------------
# EXPERIMENTAL DATA
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID Imaging Plate'
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5190
_diffrn_reflns_av_R_equivalents  0.066
_diffrn_reflns_theta_max         68.19
_diffrn_measured_fraction_theta_max 0.8883
_diffrn_reflns_theta_full        68.19
_diffrn_measured_fraction_theta_full 0.8883
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
#------------------------------------------------------------------------------
# REFINEMENT DATA
_refine_special_details          
;
Refinement using reflections with F^2^ > -10.0 sigma(F^2^). The weighted
R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are
based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only
for calculating R-factor (gt).
;
_reflns_number_total             2061
_reflns_number_gt                1856
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0749
_refine_ls_wR_factor_ref         0.2412
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_reflns         2061
_refine_ls_number_parameters     154
_refine_ls_goodness_of_fit_ref   1.959
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[\s^2^(Fo^2^) + (0.11000(Max(Fo^2^,0) + 2Fc^2^)/3)^2^]'
_refine_ls_shift/su_max          0.0002
_refine_diff_density_max         0.45
_refine_diff_density_min         -0.59
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.018 0.009
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
H H 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
O O 0.049 0.032
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
N N 0.031 0.018
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
S S 0.333 0.557
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
#------------------------------------------------------------------------------
# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S(1) S -0.1669(2) -0.1983(1) 0.37249(5) 0.0315(3) Uani 1.00 d . . .
O(1) O -0.4163(5) -0.2137(5) 0.3750(2) 0.0529(10) Uani 1.00 d . . .
O(2) O -0.1019(5) -0.0645(4) 0.4185(2) 0.0434(9) Uani 1.00 d . . .
O(3) O -0.0447(5) -0.3715(4) 0.4023(2) 0.0416(8) Uani 1.00 d . . .
N(1) N -0.2569(6) 0.2774(4) 0.4615(2) 0.0373(9) Uani 1.00 d . . .
C(1) C -0.4554(8) 0.3131(6) 0.4065(3) 0.043(1) Uani 1.00 d . . .
C(2) C -0.3749(10) 0.3563(6) 0.3047(3) 0.053(1) Uani 1.00 d . . .
C(3) C -0.586(1) 0.4158(7) 0.2525(3) 0.061(2) Uani 1.00 d . . .
C(4) C -0.525(1) 0.4600(7) 0.1494(4) 0.074(2) Uani 1.00 d . . .
C(5) C -0.744(1) 0.5144(9) 0.1027(5) 0.097(3) Uani 1.00 d . . .
C(6) C -0.0572(7) -0.1176(5) 0.2550(2) 0.0293(10) Uani 1.00 d . . .
C(7) C 0.1671(7) -0.0383(5) 0.2333(2) 0.033(1) Uani 1.00 d . . .
C(8) C -0.1838(7) -0.1308(5) 0.1872(2) 0.032(1) Uani 1.00 d . . .
C(9) C 0.2507(7) 0.0285(6) 0.1447(3) 0.036(1) Uani 1.00 d . . .
C(10) C -0.0943(7) -0.0664(5) 0.0926(2) 0.0295(10) Uani 1.00 d . . .
C(11) C 0.1258(7) 0.0178(5) 0.0707(2) 0.0297(10) Uani 1.00 d . . .
C(12) C -0.2156(7) -0.0831(5) 0.0216(2) 0.032(1) Uani 1.00 d . . .
H(1) H 0.2475 -0.0342 0.2937 0.0487 Uiso 1.00 calc . . .
H(2) H 0.4149 0.0837 0.1230 0.0487 Uiso 1.00 calc . . .
H(3) H -0.3404 -0.1952 0.2092 0.0487 Uiso 1.00 calc . . .
H(4) H -0.3886 -0.1405 0.0400 0.0487 Uiso 1.00 calc . . .
H(5) H -0.1715 0.1844 0.4615 0.0487 Uiso 1.00 calc . . .
H(6) H -0.1603 0.3763 0.4449 0.0487 Uiso 1.00 calc . . .
H(7) H -0.3153 0.2504 0.5224 0.0487 Uiso 1.00 calc . . .
H(8) H -0.5455 0.2075 0.4206 0.0516 Uiso 1.00 calc . . .
H(9) H -0.5466 0.4137 0.4218 0.0516 Uiso 1.00 calc . . .
H(10) H -0.3004 0.2510 0.2872 0.0632 Uiso 1.00 calc . . .
H(11) H -0.2708 0.4527 0.2911 0.0632 Uiso 1.00 calc . . .
H(12) H -0.6888 0.3189 0.2683 0.0713 Uiso 1.00 calc . . .
H(13) H -0.6569 0.5210 0.2709 0.0713 Uiso 1.00 calc . . .
H(14) H -0.4523 0.3559 0.1303 0.0863 Uiso 1.00 calc . . .
H(15) H -0.4241 0.5587 0.1327 0.0863 Uiso 1.00 calc . . .
H(16) H -0.8402 0.4144 0.1171 0.1168 Uiso 1.00 calc . . .
H(17) H -0.7043 0.5486 0.0374 0.1168 Uiso 1.00 calc . . .
H(18) H -0.8187 0.6155 0.1239 0.1168 Uiso 1.00 calc . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
S(1) 0.0396(7) 0.0372(6) 0.0174(5) -0.0023(4) -0.0019(4) -0.0058(4)
O(1) 0.037(2) 0.100(3) 0.020(1) -0.011(2) 0.000(1) -0.010(1)
O(2) 0.068(2) 0.041(2) 0.025(1) -0.003(1) -0.006(1) -0.015(1)
O(3) 0.062(2) 0.032(1) 0.029(1) -0.002(1) -0.008(1) -0.003(1)
N(1) 0.048(2) 0.035(2) 0.028(2) -0.001(1) -0.001(1) -0.007(1)
C(1) 0.049(3) 0.048(2) 0.034(2) 0.001(2) -0.004(2) -0.011(2)
C(2) 0.089(4) 0.041(2) 0.031(2) -0.004(2) -0.007(2) -0.012(2)
C(3) 0.097(4) 0.056(3) 0.036(3) 0.002(3) -0.018(3) -0.018(2)
C(4) 0.133(6) 0.048(3) 0.042(3) -0.004(3) -0.025(3) -0.007(2)
C(5) 0.153(7) 0.072(4) 0.075(4) 0.049(4) -0.058(4) -0.029(3)
C(6) 0.042(2) 0.032(2) 0.013(2) -0.001(2) -0.002(1) -0.004(1)
C(7) 0.040(2) 0.040(2) 0.021(2) -0.004(2) -0.006(2) -0.008(1)
C(8) 0.039(2) 0.036(2) 0.022(2) -0.005(2) -0.003(2) -0.005(1)
C(9) 0.038(2) 0.047(2) 0.025(2) -0.009(2) -0.003(2) -0.008(2)
C(10) 0.035(2) 0.031(2) 0.021(2) -0.002(1) -0.002(1) -0.005(1)
C(11) 0.038(2) 0.029(2) 0.021(2) -0.003(1) -0.002(1) -0.002(1)
C(12) 0.035(2) 0.037(2) 0.023(2) -0.007(2) -0.003(2) -0.003(1)
#------------------------------------------------------------------------------
_computing_data_collection       PROCESS-AUTO
_computing_cell_refinement       PROCESS-AUTO
_computing_data_reduction        'teXsan Ver. 1.10'
_computing_structure_solution    SIR92
_computing_structure_refinement  'teXsan Ver. 1.10'
_computing_publication_material  'teXsan Ver. 1.10'
_computing_molecular_graphics    ?
#------------------------------------------------------------------------------
_geom_special_details            
;
?
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S(1) O(1) 1.485(3) . . yes
S(1) O(2) 1.436(3) . . yes
S(1) O(3) 1.452(3) . . yes
S(1) C(6) 1.776(3) . . yes
N(1) C(1) 1.495(5) . . yes
C(1) C(2) 1.504(6) . . yes
C(2) C(3) 1.546(7) . . yes
C(3) C(4) 1.502(7) . . yes
C(4) C(5) 1.538(9) . . yes
C(6) C(7) 1.461(6) . . yes
C(6) C(8) 1.360(5) . . yes
C(7) C(9) 1.348(5) . . yes
C(8) C(10) 1.432(5) . . yes
C(9) C(11) 1.427(5) . . yes
C(10) C(11) 1.455(6) . . yes
C(10) C(12) 1.388(5) . . yes
C(11) C(12) 1.404(5) . 2_555 yes
#------------------------------------------------------------------------------
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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O(1) S(1) O(2) 114.9(2) . 1_555 1_555 yes
O(1) S(1) O(3) 114.2(2) . 1_555 1_555 yes
O(1) S(1) C(6) 107.1(2) . 1_555 1_555 yes
O(2) S(1) O(3) 110.3(2) . 1_555 1_555 yes
O(2) S(1) C(6) 104.1(2) . 1_555 1_555 yes
O(3) S(1) C(6) 105.2(2) . 1_555 1_555 yes
N(1) C(1) C(2) 110.5(4) . 1_555 1_555 yes
C(1) C(2) C(3) 107.8(4) . 1_555 1_555 yes
C(2) C(3) C(4) 112.3(5) . 1_555 1_555 yes
C(3) C(4) C(5) 109.1(6) . 1_555 1_555 yes
S(1) C(6) C(7) 119.3(3) . 1_555 1_555 yes
S(1) C(6) C(8) 119.3(3) . 1_555 1_555 yes
C(7) C(6) C(8) 121.4(3) . 1_555 1_555 yes
C(6) C(7) C(9) 120.3(3) . 1_555 1_555 yes
C(6) C(8) C(10) 119.1(4) . 1_555 1_555 yes
C(7) C(9) C(11) 120.8(4) . 1_555 1_555 yes
C(8) C(10) C(11) 119.7(3) . 1_555 1_555 yes
C(8) C(10) C(12) 120.7(4) . 1_555 1_555 yes
C(11) C(10) C(12) 119.6(3) . 1_555 1_555 yes
C(9) C(11) C(10) 118.7(3) . 1_555 1_555 yes
C(9) C(11) C(12) 120.8(4) . 1_555 2_555 yes
C(10) C(11) C(12) 120.6(3) . 1_555 2_555 yes
C(10) C(12) C(11) 119.8(4) . 1_555 2_555 yes
#------------------------------------------------------------------------------
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
S(1) C(6) C(7) C(9) -178.1(3) 1_555 1_555 1_555 1_555 yes
S(1) C(6) C(8) C(10) -179.7(3) 1_555 1_555 1_555 1_555 yes
O(1) S(1) C(6) C(7) 162.1(3) 1_555 1_555 1_555 1_555 yes
O(1) S(1) C(6) C(8) -17.9(4) 1_555 1_555 1_555 1_555 yes
O(2) S(1) C(6) C(7) 39.9(3) 1_555 1_555 1_555 1_555 yes
O(2) S(1) C(6) C(8) -140.1(3) 1_555 1_555 1_555 1_555 yes
O(3) S(1) C(6) C(7) -76.1(3) 1_555 1_555 1_555 1_555 yes
O(3) S(1) C(6) C(8) 103.9(3) 1_555 1_555 1_555 1_555 yes
N(1) C(1) C(2) C(3) -172.8(4) 1_555 1_555 1_555 1_555 yes
C(1) C(2) C(3) C(4) -179.2(4) 1_555 1_555 1_555 1_555 yes
C(2) C(3) C(4) C(5) 179.0(4) 1_555 1_555 1_555 1_555 yes
C(6) C(7) C(9) C(11) -2.1(6) 1_555 1_555 1_555 1_555 yes
C(6) C(8) C(10) C(11) -2.2(6) 1_555 1_555 1_555 1_555 yes
C(6) C(8) C(10) C(12) 177.9(4) 1_555 1_555 1_555 1_555 yes
C(7) C(6) C(8) C(10) 0.3(6) 1_555 1_555 1_555 1_555 yes
C(7) C(9) C(11) C(10) 0.2(6) 1_555 1_555 1_555 1_555 yes
C(7) C(9) C(11) C(12) -178.3(4) 1_555 1_555 1_555 2_555 yes
C(8) C(6) C(7) C(9) 1.9(6) 1_555 1_555 1_555 1_555 yes
C(8) C(10) C(11) C(9) 2.0(6) 1_555 1_555 1_555 1_555 yes
C(8) C(10) C(11) C(12) -179.5(3) 1_555 1_555 1_555 2_555 yes
C(8) C(10) C(12) C(11) 179.5(3) 1_555 1_555 1_555 2_555 yes
C(9) C(11) C(10) C(12) -178.1(4) 1_555 1_555 1_555 1_555 yes
C(9) C(11) C(12) C(10) 178.1(4) 1_555 1_555 2_555 2_555 yes
#------------------------------------------------------------------------------
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O(1) N(1) 2.888(4) . 2_456 ?
O(1) C(1) 3.185(5) . 2_456 ?
O(1) C(7) 3.459(5) . 1_455 ?
O(1) C(1) 3.497(6) . 1_545 ?
O(1) C(2) 3.598(6) . 1_545 ?
O(2) N(1) 2.849(4) . . ?
O(2) N(1) 3.086(4) . 2_556 ?
O(2) O(2) 3.210(5) . 2_556 ?
O(2) C(1) 3.395(5) . . ?
O(3) N(1) 2.903(4) . 1_545 ?
O(3) N(1) 3.096(4) . 2_556 ?
O(3) O(3) 3.204(5) . 2_546 ?
O(3) C(1) 3.493(5) . 1_545 ?
O(3) C(2) 3.569(6) . 1_545 ?
C(5) C(9) 3.561(8) . 1_455 ?
C(8) C(9) 3.567(6) . 1_455 ?
C(9) C(12) 3.597(6) . 1_655 ?
C(12) C(12) 3.600(8) . 2_455 ?