#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/20/1502081.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_1502081
loop_
_publ_author_name
'Dong, Yanmei'
'Bolduc, Andréanne'
'McGregor, Nicholas'
'Skene, W. G.'
_publ_section_title
;
 Push-pull aminobithiophenes--highly fluorescent stable fluorophores.
;
_journal_issue                   7
_journal_name_full               'Organic letters'
_journal_page_first              1844
_journal_page_last               1847
_journal_paper_doi               10.1021/ol200353k
_journal_volume                  13
_journal_year                    2011
_chemical_compound_source        'Synthesized by the authors. See text'
_chemical_formula_moiety         'C12 H11 N O3 S2'
_chemical_formula_sum            'C12 H11 N O3 S2'
_chemical_formula_weight         281.34
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 92.787(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.5461(7)
_cell_length_b                   5.6788(3)
_cell_length_c                   16.1132(8)
_cell_measurement_reflns_used    15645
_cell_measurement_temperature    150
_cell_measurement_theta_max      69.33
_cell_measurement_theta_min      3.27
_cell_volume                     1238.05(11)
_computing_cell_refinement       'SAINT V7.68A(Bruker AXS, 2009)'
_computing_data_collection       'APEX2  (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A(Bruker AXS, 2009)'
_computing_molecular_graphics    'SHELXTL v6.12 (Bruker AXS, 2001)'
_computing_publication_material  'UdMX (Maris, 2004)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker Microstar'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'Helios optics'
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.036
_diffrn_reflns_av_sigmaI/netI    0.0132
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            25307
_diffrn_reflns_theta_full        69.66
_diffrn_reflns_theta_max         69.66
_diffrn_reflns_theta_min         3.27
_exptl_absorpt_coefficient_mu    3.913
_exptl_absorpt_correction_T_max  0.8892
_exptl_absorpt_correction_T_min  0.5703
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle-like
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2313
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0276
_refine_ls_R_factor_gt           0.0262
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0447P)²+0.3205P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0713
_refine_ls_wR_factor_ref         0.0724
_reflns_number_gt                2168
_reflns_number_total             2313
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ol200353k_si_002.cif
_cod_data_source_block           boldu4
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_geom_bond_publ_flag' value 'Y' changed to 'y'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (19
times).

'_geom_angle_publ_flag' value 'Y' changed to 'y' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29 (26
times).

'_geom_torsion_publ_flag' value 'Y' changed to 'y' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29 (34 times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               1502081
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S 0.15522(2) 1.22353(6) 0.47777(2) 0.02616(11) Uani 1 1 d .
S2 S -0.06751(2) 1.26113(5) 0.396823(19) 0.02543(11) Uani 1 1 d .
N1 N 0.34091(9) 1.1627(2) 0.53887(8) 0.0331(3) Uani 1 1 d .
H1A H 0.3970(14) 1.111(3) 0.5361(11) 0.045(5) Uiso 1 1 d .
H1B H 0.3337(12) 1.291(3) 0.5647(10) 0.028(4) Uiso 1 1 d .
C1 C 0.26869(9) 1.0826(2) 0.48668(8) 0.0260(3) Uani 1 1 d .
C2 C 0.27029(9) 0.8862(2) 0.43422(8) 0.0255(3) Uani 1 1 d .
C3 C 0.17911(9) 0.8526(2) 0.38883(8) 0.0248(3) Uani 1 1 d .
H3 H 0.1677 0.7266 0.3508 0.030 Uiso 1 1 calc R
C4 C 0.10913(9) 1.0176(2) 0.40462(7) 0.0238(3) Uani 1 1 d .
C5 C 0.00866(9) 1.0313(2) 0.37128(7) 0.0230(3) Uani 1 1 d .
C6 C -0.04018(9) 0.8747(2) 0.31773(7) 0.0254(3) Uani 1 1 d .
H6 H -0.0104 0.7373 0.2965 0.030 Uiso 1 1 calc R
C7 C -0.13779(9) 0.9402(2) 0.29825(8) 0.0270(3) Uani 1 1 d .
H7 H -0.1814 0.8515 0.2625 0.032 Uiso 1 1 calc R
C8 C -0.16458(9) 1.1468(2) 0.33614(8) 0.0264(3) Uani 1 1 d .
C9 C -0.25969(11) 1.2602(2) 0.33075(9) 0.0317(3) Uani 1 1 d .
H9 H -0.3102 1.1890 0.2963 0.038 Uiso 1 1 calc R
O9 O -0.28045(8) 1.44060(19) 0.36697(7) 0.0439(3) Uani 1 1 d .
C10 C 0.36007(10) 0.7501(2) 0.42652(8) 0.0263(3) Uani 1 1 d .
O10 O 0.43816(7) 0.79255(18) 0.46455(6) 0.0348(2) Uani 1 1 d .
O11 O 0.35028(6) 0.57254(16) 0.37152(5) 0.0283(2) Uani 1 1 d .
C12 C 0.43847(10) 0.4291(3) 0.36365(8) 0.0317(3) Uani 1 1 d .
H12A H 0.4575 0.3535 0.4174 0.038 Uiso 1 1 calc R
H12B H 0.4942 0.5281 0.3468 0.038 Uiso 1 1 calc R
C13 C 0.41436(13) 0.2451(3) 0.29871(10) 0.0387(4) Uani 1 1 d .
H13A H 0.3548 0.1594 0.3132 0.058 Uiso 1 1 calc R
H13B H 0.4698 0.1349 0.2961 0.058 Uiso 1 1 calc R
H13C H 0.4028 0.3213 0.2445 0.058 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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_publ_flag
C1 S1 C4 91.89(6) y
C5 S2 C8 91.61(6) y
C1 N1 H1A 119.8(13) ?
C1 N1 H1B 120.2(11) ?
H1A N1 H1B 117.6(17) ?
N1 C1 C2 128.15(12) y
N1 C1 S1 120.89(10) y
C2 C1 S1 110.96(9) y
C1 C2 C3 112.32(11) y
C1 C2 C10 120.89(11) y
C3 C2 C10 126.67(12) y
C4 C3 C2 114.03(12) y
C4 C3 H3 123.0 ?
C2 C3 H3 123.0 ?
C3 C4 C5 128.27(12) y
C3 C4 S1 110.80(9) y
C5 C4 S1 120.90(9) y
C6 C5 C4 127.72(11) y
C6 C5 S2 111.16(9) y
C4 C5 S2 121.12(9) y
C5 C6 C7 112.84(11) y
C5 C6 H6 123.6 ?
C7 C6 H6 123.6 ?
C8 C7 C6 113.21(12) y
C8 C7 H7 123.4 ?
C6 C7 H7 123.4 ?
C7 C8 C9 127.45(12) y
C7 C8 S2 111.17(10) y
C9 C8 S2 121.36(10) y
O9 C9 C8 125.04(14) y
O9 C9 H9 117.5 ?
C8 C9 H9 117.5 ?
O10 C10 O11 122.29(12) y
O10 C10 C2 124.16(12) y
O11 C10 C2 113.54(11) y
C10 O11 C12 114.93(10) y
O11 C12 C13 107.32(11) y
O11 C12 H12A 110.2 ?
C13 C12 H12A 110.2 ?
O11 C12 H12B 110.2 ?
C13 C12 H12B 110.2 ?
H12A C12 H12B 108.5 ?
C12 C13 H13A 109.5 ?
C12 C13 H13B 109.5 ?
H13A C13 H13B 109.5 ?
C12 C13 H13C 109.5 ?
H13A C13 H13C 109.5 ?
H13B C13 H13C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C1 1.7326(13) y
S1 C4 1.7537(13) y
S2 C5 1.7261(12) y
S2 C8 1.7268(13) y
N1 C1 1.3385(18) y
N1 H1a 0.818(19) ?
N1 H1b 0.846(17) ?
C1 C2 1.4003(18) y
C2 C3 1.4174(18) y
C2 C10 1.4513(18) y
C3 C4 1.3652(18) y
C3 H3 0.9500 ?
C4 C5 1.4407(17) y
C5 C6 1.3845(18) y
C6 C7 1.3946(18) y
C6 H6 0.9500 ?
C7 C8 1.3789(18) y
C7 H7 0.9500 ?
C8 C9 1.4394(19) y
C9 O9 1.2186(17) y
C9 H9 0.9500 ?
C10 O10 1.2204(17) y
C10 O11 1.3449(16) y
O11 C12 1.4565(15) y
C12 C13 1.503(2) y
C12 H12a 0.9900 ?
C12 H12b 0.9900 ?
C13 H13a 0.9800 ?
C13 H13b 0.9800 ?
C13 H13c 0.9800 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O10 0.818(19) 2.231(19) 2.7825(17) 125.1(16) .
N1 H1A O10 0.818(19) 2.299(19) 3.0066(16) 145.1(17) 3_676
N1 H1B O9 0.846(17) 2.034(18) 2.8579(17) 164.4(15) 3_586
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_publ_flag
C4 S1 C1 N1 -178.99(12) y
C4 S1 C1 C2 0.65(10) y
N1 C1 C2 C3 178.84(13) y
S1 C1 C2 C3 -0.78(14) y
N1 C1 C2 C10 -4.9(2) y
S1 C1 C2 C10 175.51(10) y
C1 C2 C3 C4 0.51(16) y
C10 C2 C3 C4 -175.51(12) y
C2 C3 C4 C5 -178.02(12) y
C2 C3 C4 S1 -0.01(14) y
C1 S1 C4 C3 -0.37(10) y
C1 S1 C4 C5 177.81(10) y
C3 C4 C5 C6 2.4(2) y
S1 C4 C5 C6 -175.45(10) y
C3 C4 C5 S2 -177.92(10) y
S1 C4 C5 S2 4.26(14) y
C8 S2 C5 C6 0.21(9) y
C8 S2 C5 C4 -179.54(10) y
C4 C5 C6 C7 179.44(11) y
S2 C5 C6 C7 -0.29(14) y
C5 C6 C7 C8 0.24(16) y
C6 C7 C8 C9 -178.57(13) y
C6 C7 C8 S2 -0.08(14) y
C5 S2 C8 C7 -0.07(10) y
C5 S2 C8 C9 178.52(11) y
C7 C8 C9 O9 178.30(14) y
S2 C8 C9 O9 -0.1(2) y
C1 C2 C10 O10 0.9(2) y
C3 C2 C10 O10 176.66(13) y
C1 C2 C10 O11 -177.74(11) y
C3 C2 C10 O11 -2.02(19) y
O10 C10 O11 C12 2.60(18) y
C2 C10 O11 C12 -178.69(10) y
C10 O11 C12 C13 -178.74(11) y
