#------------------------------------------------------------------------------
#$Date: 2017-01-06 07:40:26 +0200 (Fri, 06 Jan 2017) $
#$Revision: 189938 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/00/26/4002689.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_4002689
loop_
_publ_author_name
'Zhang, Zhiyun'
'Chen, Yi-An'
'Hung, Wen-Yi'
'Tang, Wei-Feng'
'Hsu, Yen-Hao'
'Chen, Chi-Lin'
'Meng, Fan-Yi'
'Chou, Pi-Tai'
_publ_section_title
;
 Control of the Reversibility of Excited-State Intramolecular Proton
 Transfer (ESIPT) Reaction: Host-Polarity Tuning White Organic Light
 Emitting Diode on a New Thiazolo[5,4-d]thiazole ESIPT System
;
_journal_issue                   23
_journal_name_full               'Chemistry of Materials'
_journal_page_first              8815
_journal_paper_doi               10.1021/acs.chemmater.6b04707
_journal_volume                  28
_journal_year                    2016
_chemical_formula_sum            'C26 H30 N2 O2 S2'
_chemical_formula_weight         466.64
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 111.1987(12)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.3481(4)
_cell_length_b                   11.3487(4)
_cell_length_c                   10.7207(3)
_cell_measurement_reflns_used    3896
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      2.72
_cell_volume                     1173.82(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_unetI/netI     0.0311
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7891
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.493
_diffrn_reflns_theta_min         2.716
_exptl_absorpt_coefficient_mu    0.253
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6314
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         2691
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0342
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0402P)²+0.4394P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0805
_refine_ls_wR_factor_ref         0.0858
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2195
_reflns_number_total             2691
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cm6b04707_si_004.cif
_cod_data_source_block           ic17624
_cod_depositor_comments
'Adding full bibliography for 4002689--4002690.cif.'
_cod_database_code               4002689
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelx_estimated_absorpt_t_min   0.956
_shelx_estimated_absorpt_t_max   0.978
loop_
_space_group_symop_operation_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'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
S1 S 0.55355(4) 0.17154(3) -0.01928(3) 0.02022(11) Uani 1 1 d . .
O1 O 0.62398(11) 0.37924(9) 0.09982(10) 0.0235(2) Uani 1 1 d . .
N1 N 0.50916(13) 0.04296(10) 0.16336(11) 0.0181(3) Uani 1 1 d . .
C1 C 0.50943(15) 0.02561(12) -0.05423(13) 0.0166(3) Uani 1 1 d . .
C2 C 0.54404(14) 0.15019(12) 0.14025(13) 0.0162(3) Uani 1 1 d . .
C3 C 0.57848(14) 0.24256(12) 0.24325(13) 0.0160(3) Uani 1 1 d . .
C4 C 0.57188(15) 0.21503(13) 0.36814(13) 0.0173(3) Uani 1 1 d . .
H4 H 0.5408 0.1388 0.3811 0.021 Uiso 1 1 calc R U
C5 C 0.60899(15) 0.29477(13) 0.47439(14) 0.0178(3) Uani 1 1 d . .
C6 C 0.65374(16) 0.40574(13) 0.45128(14) 0.0215(3) Uani 1 1 d . .
H6 H 0.6810 0.4618 0.5219 0.026 Uiso 1 1 calc R U
C7 C 0.65964(16) 0.43689(13) 0.32806(14) 0.0216(3) Uani 1 1 d . .
H7 H 0.6894 0.5136 0.3152 0.026 Uiso 1 1 calc R U
C8 C 0.62221(15) 0.35618(13) 0.22398(13) 0.0177(3) Uani 1 1 d . .
C9 C 0.59871(16) 0.25879(13) 0.60840(13) 0.0200(3) Uani 1 1 d . .
C10 C 0.68267(19) 0.14596(15) 0.66106(16) 0.0310(4) Uani 1 1 d . .
H10A H 0.6452 0.0818 0.5969 0.047 Uiso 1 1 calc R U
H10B H 0.6765 0.1245 0.7473 0.047 Uiso 1 1 calc R U
H10C H 0.7799 0.1596 0.6726 0.047 Uiso 1 1 calc R U
C11 C 0.44590(18) 0.23652(17) 0.58705(16) 0.0311(4) Uani 1 1 d . .
H11A H 0.3922 0.3083 0.5528 0.047 Uiso 1 1 calc R U
H11B H 0.4379 0.2146 0.6724 0.047 Uiso 1 1 calc R U
H11C H 0.4101 0.1725 0.5224 0.047 Uiso 1 1 calc R U
C12 C 0.65506(18) 0.35540(15) 0.71452(15) 0.0283(4) Uani 1 1 d . .
H12A H 0.7520 0.3717 0.7272 0.042 Uiso 1 1 calc R U
H12B H 0.6491 0.3289 0.7993 0.042 Uiso 1 1 calc R U
H12C H 0.6000 0.4273 0.6848 0.042 Uiso 1 1 calc R U
C13 C 0.67674(18) 0.49060(14) 0.07702(15) 0.0260(3) Uani 1 1 d . .
H13A H 0.6221 0.5543 0.0952 0.039 Uiso 1 1 calc R U
H13B H 0.6704 0.4953 -0.0163 0.039 Uiso 1 1 calc R U
H13C H 0.7738 0.4984 0.1365 0.039 Uiso 1 1 calc R U
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
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
C1 S1 C2 88.60(6) . .
C8 O1 C13 118.46(11) . .
C2 N1 C1 109.26(11) . 3_655
N1 C1 C1 117.79(16) 3_655 3_655
N1 C1 S1 132.94(10) 3_655 .
C1 C1 S1 109.26(13) 3_655 .
N1 C2 C3 121.72(12) . .
N1 C2 S1 115.08(10) . .
C3 C2 S1 123.14(10) . .
C4 C3 C8 118.33(12) . .
C4 C3 C2 118.47(12) . .
C8 C3 C2 123.16(12) . .
C5 C4 C3 122.79(13) . .
C6 C5 C4 116.84(13) . .
C6 C5 C9 123.15(13) . .
C4 C5 C9 120.01(13) . .
C7 C6 C5 122.01(13) . .
C8 C7 C6 120.09(14) . .
O1 C8 C7 124.10(13) . .
O1 C8 C3 115.98(12) . .
C7 C8 C3 119.92(13) . .
C5 C9 C11 108.71(12) . .
C5 C9 C12 111.57(12) . .
C11 C9 C12 108.84(13) . .
C5 C9 C10 110.16(12) . .
C11 C9 C10 109.46(13) . .
C12 C9 C10 108.08(13) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C1 1.7227(14) .
S1 C2 1.7650(14) .
O1 C8 1.3633(16) .
O1 C13 1.4323(17) .
N1 C2 1.3180(18) .
N1 C1 1.3597(17) 3_655
C1 N1 1.3597(17) 3_655
C1 C1 1.375(3) 3_655
C2 C3 1.4700(18) .
C3 C4 1.4003(19) .
C3 C8 1.4063(19) .
C4 C5 1.3955(19) .
C5 C6 1.395(2) .
C5 C9 1.5338(19) .
C6 C7 1.390(2) .
C7 C8 1.386(2) .
C9 C11 1.535(2) .
C9 C12 1.535(2) .
C9 C10 1.536(2) .
