#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/61/1506170.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1506170
loop_
_publ_author_name
'Mizobe, Yuji'
'Miyata, Mikiji'
'Hisaki, Ichiro'
'Hasegawa, Yasuchika'
'Tohnai, Norimitsu'
_publ_section_title
;
 Anomalous anthracene arrangement and rare excimer emission in the solid
 state: transcription and translation of molecular information.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              4295
_journal_page_last               4298
_journal_paper_doi               10.1021/ol0616440
_journal_volume                  8
_journal_year                    2006
_chemical_formula_sum            'C13 H20 N O2.5 S1.5'
_chemical_formula_weight         278.40
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                74.48(1)
_cell_angle_beta                 78.50(1)
_cell_angle_gamma                75.38(1)
_cell_formula_units_Z            2
_cell_length_a                   5.6042(9)
_cell_length_b                   10.207(1)
_cell_length_c                   14.106(2)
_cell_measurement_reflns_used    7602
_cell_measurement_temperature    213.2
_cell_measurement_theta_max      68.3
_cell_measurement_theta_min      3.3
_cell_volume                     744.74(18)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        'teXsan Ver. 1.10'
_computing_publication_material  'teXsan Ver. 1.10'
_computing_structure_refinement  'teXsan Ver. 1.10'
_computing_structure_solution    SIR92
_diffrn_measured_fraction_theta_full 0.9340
_diffrn_measured_fraction_theta_max 0.9340
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID Imaging Plate'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5419
_diffrn_reflns_av_R_equivalents  0.071
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8268
_diffrn_reflns_theta_full        68.21
_diffrn_reflns_theta_max         68.21
_exptl_absorpt_coefficient_mu    2.570
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_correction_T_min  0.523
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(Higashi, 1999)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_refine_diff_density_max         2.31
_refine_diff_density_min         -1.37
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.733
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2366
_refine_ls_R_factor_gt           0.1318
_refine_ls_shift/su_max          0.0019
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²) + (0.05000(Max(Fo²,0) + 2Fc²)/3)²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.3250
_reflns_number_gt                1730
_reflns_number_total             2534
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            ol0616440si20060803_013924.cif
_cod_data_source_block           secBu_thiox2_
_cod_original_cell_volume        744.7(2)
_cod_original_sg_symbol_H-M      'P -1         '
_cod_original_formula_sum        'C13 H20 N O2.50 S1.50 '
_cod_database_code               1506170
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
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
S(1) S -0.0274(3) -0.3348(2) 1.3711(1) 0.0592(6) Uani 1.00 d
O(1) O 0.178(1) -0.4434(7) 1.3777(5) 0.094(2) Uani 1.00 d
O(2) O -0.037(1) -0.2550(8) 1.4519(5) 0.091(2) Uani 1.00 d
O(3) O -0.270(1) -0.3563(7) 1.3792(5) 0.086(2) Uani 1.00 d
O(4) O 0.387(2) -0.6346(9) 1.0587(8) 0.132(4) Uani 1.00 d
N(1) N -0.375(1) 0.3649(6) 1.4389(5) 0.056(2) Uani 1.00 d
C(1) C -0.096(1) -0.1970(7) 1.1799(6) 0.050(2) Uani 1.00 d
C(2) C 0.030(1) -0.2125(7) 1.2577(5) 0.045(2) Uani 1.00 d
C(3) C 0.210(1) -0.1351(8) 1.2475(5) 0.051(2) Uani 1.00 d
C(4) C 0.257(1) -0.0369(8) 1.1630(5) 0.052(2) Uani 1.00 d
C(5) C 0.173(1) 0.0789(7) 0.9913(5) 0.048(2) Uani 1.00 d
C(6) C 0.129(1) -0.0178(7) 1.0800(5) 0.044(2) Uani 1.00 d
C(7) C 0.051(1) 0.0966(7) 0.9114(5) 0.040(2) Uani 1.00 d
C(8) C -0.353(2) 0.282(2) 1.365(1) 0.113(5) Uani 1.00 d
C(9) C -0.131(3) 0.314(2) 1.286(1) 0.136(6) Uani 1.00 d
C(10) C -0.381(4) 0.157(2) 1.400(2) 0.175(9) Uani 1.00 d
C(11) C -0.416(3) 0.083(2) 1.318(2) 0.162(8) Uani 1.00 d
C(12) C 0.314(3) -0.496(2) 1.085(1) 0.161(7) Uani 1.00 d
C(13) C 0.533(3) -0.410(1) 1.058(1) 0.120(5) Uani 1.00 d
H(1) H -0.2208 -0.2502 1.1872 0.0589 Uiso 1.00 calc
H(2) H 0.3068 -0.1534 1.3004 0.0616 Uiso 1.00 calc
H(3) H 0.3728 0.0194 1.1589 0.0633 Uiso 1.00 calc
H(4) H 0.2929 0.1340 0.9862 0.0565 Uiso 1.00 calc
H(5) H -0.4985 0.3212 1.3360 0.1421 Uiso 1.00 calc
H(6) H 0.0188 0.2932 1.3127 0.1596 Uiso 1.00 calc
H(7) H -0.1652 0.4120 1.2533 0.1596 Uiso 1.00 calc
H(8) H -0.1091 0.2632 1.2352 0.1596 Uiso 1.00 calc
H(9) H -0.5115 0.1438 1.4543 0.1849 Uiso 1.00 calc
H(10) H -0.2258 0.0961 1.4278 0.1849 Uiso 1.00 calc
H(11) H -0.2818 0.0859 1.2667 0.1871 Uiso 1.00 calc
H(12) H -0.4308 -0.0117 1.3468 0.1871 Uiso 1.00 calc
H(13) H -0.5676 0.1333 1.2934 0.1871 Uiso 1.00 calc
H(14) H 0.2379 -0.5009 1.1521 0.1844 Uiso 1.00 calc
H(15) H 0.1752 -0.4334 1.0452 0.1844 Uiso 1.00 calc
H(16) H 0.6589 -0.4642 1.0982 0.1419 Uiso 1.00 calc
H(17) H 0.4734 -0.3219 1.0777 0.1419 Uiso 1.00 calc
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)
;
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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O(1) S(1) O(2) 108.0(5) 1_555 1_555 yes
O(1) S(1) O(3) 122.1(5) 1_555 1_555 yes
O(1) S(1) C(2) 107.8(3) 1_555 1_555 yes
O(2) S(1) O(3) 106.0(4) 1_555 1_555 yes
O(2) S(1) C(2) 103.7(4) 1_555 1_555 yes
O(3) S(1) C(2) 107.8(3) 1_555 1_555 yes
C(12) O(4) C(13) 101(1) 1_555 2_647 yes
C(2) C(1) C(7) 120.4(6) 1_555 2_557 yes
S(1) C(2) C(1) 120.6(5) 1_555 1_555 yes
S(1) C(2) C(3) 119.0(5) 1_555 1_555 yes
C(1) C(2) C(3) 120.3(6) 1_555 1_555 yes
C(2) C(3) C(4) 121.4(6) 1_555 1_555 yes
C(3) C(4) C(6) 119.7(6) 1_555 1_555 yes
C(6) C(5) C(7) 122.1(6) 1_555 1_555 yes
C(4) C(6) C(5) 122.1(6) 1_555 1_555 yes
C(4) C(6) C(7) 119.4(6) 1_555 2_557 yes
C(5) C(6) C(7) 118.4(6) 1_555 2_557 yes
C(1) C(7)* C(5)* 121.9(6) 2_557 1_555 yes
C(1) C(7)* C(6) 118.5(6) 2_557 2_557 yes
C(5) C(7) C(6) 119.5(6) 1_555 2_557 yes
N(1) C(8) C(9) 107(1) 1_555 1_555 yes
N(1) C(8) C(10) 116(1) 1_555 1_555 yes
C(9) C(8) C(10) 120(1) 1_555 1_555 yes
C(8) C(10) C(11) 113(2) 1_555 1_555 yes
O(4) C(12) C(13) 114(1) 1_555 1_555 yes
O(4) C(13)* C(12)* 111(1) 2_647 1_555 yes
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
S(1) O(1) 1.380(6) . yes
S(1) O(2) 1.555(7) . yes
S(1) O(3) 1.410(6) . yes
S(1) C(2) 1.773(7) . yes
O(4) C(12) 1.50(2) . yes
O(4) C(13) 1.59(2) 2_647 yes
N(1) C(8) 1.48(1) . yes
C(1) C(2) 1.37(1) . yes
C(1) C(7) 1.438(9) 2_557 yes
C(2) C(3) 1.399(9) . yes
C(3) C(4) 1.365(9) . yes
C(4) C(6) 1.435(10) . yes
C(5) C(6) 1.392(9) . yes
C(5) C(7) 1.380(10) . yes
C(6) C(7) 1.414(9) 2_557 yes
C(8) C(9) 1.54(2) . yes
C(8) C(10) 1.27(2) . yes
C(10) C(11) 1.61(3) . yes
C(12) C(13) 1.61(2) . yes
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
O(1) N(1) 2.887(9) 1_645
O(1) C(8) 3.34(1) 1_645
O(1) N(1) 3.35(1) 2_558
O(1) O(3) 3.432(10) 1_655
O(1) O(2) 3.521(9) 2_548
O(1) O(3) 3.553(9) 2_548
O(2) N(1) 2.853(10) 2_558
O(2) C(10) 3.57(2) 2_458
O(3) N(1) 2.912(8) 2_458
O(3) N(1) 2.918(9) 1_545
N(1) N(1) 3.49(1) 2_468
C(2) C(11) 3.58(2) .
C(4) C(5) 3.49(1) 2_657
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(2) C(1) C(7) 179.2(5) 1_555 1_555 1_555 2_557 yes
S(1) C(2) C(3) C(4) -178.1(6) 1_555 1_555 1_555 1_555 yes
O(1) S(1) C(2) C(1) 108.2(7) 1_555 1_555 1_555 1_555 yes
O(1) S(1) C(2) C(3) -69.7(7) 1_555 1_555 1_555 1_555 yes
O(2) S(1) C(2) C(1) -137.5(6) 1_555 1_555 1_555 1_555 yes
O(2) S(1) C(2) C(3) 44.6(7) 1_555 1_555 1_555 1_555 yes
O(3) S(1) C(2) C(1) -25.3(8) 1_555 1_555 1_555 1_555 yes
O(3) S(1) C(2) C(3) 156.8(6) 1_555 1_555 1_555 1_555 yes
N(1) C(8) C(10) C(11) 166(1) 1_555 1_555 1_555 1_555 yes
C(1) C(2) C(3) C(4) 3(1) 1_555 1_555 1_555 1_555 yes
C(1) C(7) C(5) C(6) -179.7(7) 1_555 2_557 2_557 2_557 yes
C(1) C(7) C(6) C(4) -1(1) 1_555 2_557 1_555 1_555 yes
C(1) C(7) C(6) C(5) 179.7(7) 1_555 2_557 1_555 1_555 yes
C(2) C(1) C(7) C(5) 179.5(7) 1_555 1_555 2_557 2_557 yes
C(2) C(1) C(7) C(6) 1(1) 1_555 1_555 2_557 1_555 yes
C(2) C(3) C(4) C(6) -3(1) 1_555 1_555 1_555 1_555 yes
C(3) C(2) C(1) C(7) -2(1) 1_555 1_555 1_555 2_557 yes
C(3) C(4) C(6) C(5) -178.8(8) 1_555 1_555 1_555 1_555 yes
C(3) C(4) C(6) C(7) 3(1) 1_555 1_555 1_555 2_557 yes
C(4) C(6) C(5) C(7) 179.6(7) 1_555 1_555 1_555 1_555 yes
C(4) C(6) C(7) C(5) -179.6(7) 1_555 1_555 2_557 2_557 yes
C(9) C(8) C(10) C(11) -61(2) 1_555 1_555 1_555 1_555 yes
