#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/90/4029032.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_4029032
loop_
_publ_author_name
'Kamimura, Akio'
'Nokubi, Tomomi'
'Watanabe, Ryusuke'
'Ishikawa, Mari'
'Nasu, Kotaro'
'Uno, Hidemitsu'
'Sumimoto, Michinori'
_publ_section_title
;
 4,4'-Diarylsulfanyl-2,2',5,5'-tetraoxybiaryl Derivatives as a
 Water-Soluble Fluorescent Dye.
;
_journal_issue                   3
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1068
_journal_paper_doi               10.1021/jo402522y
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C14 H12 N3 O2 S '
_chemical_formula_sum            'C14 H12 N3 O2 S'
_chemical_formula_weight         286.33
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      5
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_cell_angle_alpha                90.0000
_cell_angle_beta                 91.193(6)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   14.549(3)
_cell_length_b                   5.7568(12)
_cell_length_c                   14.436(3)
_cell_measurement_reflns_used    2369
_cell_measurement_temperature    296.1
_cell_measurement_theta_max      27.8
_cell_measurement_theta_min      3.1
_cell_volume                     1208.8(4)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.8'
_computing_structure_refinement  CRYSTALS
_computing_structure_solution    SIR92
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.052
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            1496
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_exptl_absorpt_coefficient_mu    0.273
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             596.00
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.25
_refine_diff_density_min         -0.34
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   5.750
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     168
_refine_ls_number_reflns         1009
_refine_ls_R_factor_gt           0.0548
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1.0'
_refine_ls_weighting_scheme      unit
_refine_ls_wR_factor_ref         0.0561
_reflns_number_gt                1001
_reflns_number_total             1496
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            jo402522y_si_002.cif
_cod_data_source_block           '_nokubi'
_cod_original_formula_sum        'C14 H12 N3 O2 S '
_cod_database_code               4029032
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,+Y,-Z
3 1/2+X,1/2+Y,+Z
4 1/2-X,1/2+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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S(1) S 0.40098(12) 0.0194(5) 0.14604(11) 0.0535(5) Uani 1.00 1 d .
O(1) O 0.5794(3) 0.4145(9) 0.4160(3) 0.0515(14) Uani 1.00 1 d .
O(2) O 0.3245(3) -0.2489(9) 0.3042(3) 0.0530(15) Uani 1.00 1 d .
C(4) C 0.480880(10) 0.1033(11) 0.451140(10) 0.0374(17) Uani 1.00 1 d .
C(5) C 0.4857(4) 0.2345(13) 0.2926(4) 0.0405(18) Uani 1.00 1 d .
C(6) C 0.4224(3) 0.0635(13) 0.2671(3) 0.0407(18) Uani 1.00 1 d .
C(7) C 0.3872(4) -0.0838(12) 0.3326(4) 0.0391(17) Uani 1.00 1 d .
C(8) C 0.2816(4) 0.0740(12) 0.1309(3) 0.0384(17) Uani 1.00 1 d .
C(9) C 0.2281(4) -0.0900(13) 0.0859(4) 0.048(2) Uani 1.00 1 d .
C(10) C 0.4177(4) -0.0625(12) 0.4249(4) 0.0394(17) Uani 1.00 1 d .
C(11) C 0.2437(4) 0.2842(13) 0.1566(4) 0.046(2) Uani 1.00 1 d .
C(12) C 0.5162(4) 0.2549(12) 0.3851(4) 0.0391(17) Uani 1.00 1 d .
C(13) C 0.6172(5) 0.5661(14) 0.3484(4) 0.061(2) Uani 1.00 1 d .
C(14) C 0.1504(5) 0.3236(14) 0.1399(4) 0.053(2) Uani 1.00 1 d .
C(15) C 0.2859(5) -0.3903(15) 0.3733(5) 0.063(2) Uani 1.00 1 d .
C(16) C 0.1354(4) -0.0451(14) 0.0685(4) 0.054(2) Uani 1.00 1 d .
C(17) C 0.0967(5) 0.1603(15) 0.0950(5) 0.055(2) Uani 1.00 1 d .
H(1) H 0.5000 0.1150 0.5000 0.045 Uiso 1.00 2 c R
H(2) H 0.5087 0.3374 0.2471 0.049 Uiso 1.00 1 c R
H(3) H 0.3932 -0.1623 0.4706 0.047 Uiso 1.00 1 c R
H(4) H 0.2548 -0.2323 0.0668 0.058 Uiso 1.00 1 c R
H(7) H 0.2812 0.3995 0.1855 0.055 Uiso 1.00 1 c R
H(8) H 0.6710 0.4969 0.3243 0.074 Uiso 1.00 1 c R
H(9) H 0.6329 0.7097 0.3771 0.074 Uiso 1.00 1 c R
H(10) H 0.5739 0.5926 0.2994 0.074 Uiso 1.00 1 c R
H(11) H 0.1235 0.4651 0.1597 0.064 Uiso 1.00 1 c R
H(12) H 0.3230 -0.5250 0.3810 0.076 Uiso 1.00 1 c R
H(13) H 0.2253 -0.4350 0.3552 0.076 Uiso 1.00 1 c R
H(14) H 0.2843 -0.3072 0.4300 0.076 Uiso 1.00 1 c R
H(15) H 0.0980 -0.1587 0.0383 0.065 Uiso 1.00 1 c R
H(16) H 0.0335 0.1908 0.0824 0.066 Uiso 1.00 1 c R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
N N 0.006 0.003
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
C C 0.003 0.002
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.011 0.006
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
S S 0.125 0.123
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
