#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:08:19 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178459 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/80/4028048.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_4028048
loop_
_publ_author_name
'Tao Tao'
'Yu-Xin Peng'
'Wei Huang'
'Xiao-Zeng You'
_publ_section_title
;
 Coplanar Bithiazole-Centered Heterocyclic Aromatic Fluorescent Compounds
 Having Different Donor/Acceptor Terminal Groups
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2472
_journal_page_last               2481
_journal_paper_doi               10.1021/jo302706t
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C34 H42 N4 O6 S2'
_chemical_formula_sum            'C34 H42 N4 O6 S2'
_chemical_formula_weight         666.86
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                100.073(5)
_cell_angle_beta                 96.591(7)
_cell_angle_gamma                101.281(6)
_cell_formula_units_Z            1
_cell_length_a                   5.4606(19)
_cell_length_b                   12.111(4)
_cell_length_c                   14.081(5)
_cell_measurement_reflns_used    8282
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      2.5
_cell_volume                     888.4(5)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (BRUKER 2000)'
_computing_data_reduction        'SAINT (BRUKER 2000)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (BRUKER 2000)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 0.909
_diffrn_measured_fraction_theta_max 0.909
_diffrn_measurement_device_type  'BRUKER Smart Apex CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0652
_diffrn_reflns_av_sigmaI/netI    0.1210
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4680
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.49
_exptl_absorpt_coefficient_mu    0.198
_exptl_absorpt_correction_T_max  0.9805
_exptl_absorpt_correction_T_min  0.9710
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, BRUKER(2000)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_description       needle
_exptl_crystal_F_000             354
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         2850
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.1748
_refine_ls_R_factor_gt           0.0908
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1444P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2409
_refine_ls_wR_factor_ref         0.2773
_reflns_number_gt                1434
_reflns_number_total             2850
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo302706t_si_003_6.cif
_cod_data_source_block           2BA2TZ
_cod_database_code               4028048
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.4196(11) 0.9637(5) 0.0180(4) 0.0424(15) Uani 1 1 d . . .
C2 C -0.2642(11) 0.8085(4) 0.0268(4) 0.0384(15) Uani 1 1 d . . .
C3 C -0.1151(11) 0.8821(5) 0.1077(4) 0.0394(15) Uani 1 1 d . . .
C4 C 0.0792(11) 0.8623(4) 0.1812(4) 0.0408(15) Uani 1 1 d . . .
C5 C 0.2341(11) 0.7876(4) 0.1545(5) 0.0448(16) Uani 1 1 d . . .
H5 H 0.2210 0.7525 0.0893 0.054 Uiso 1 1 calc R . .
C6 C 0.4095(12) 0.7648(5) 0.2248(5) 0.0462(16) Uani 1 1 d . . .
H6 H 0.5078 0.7125 0.2062 0.055 Uiso 1 1 calc R . .
C7 C 0.4385(12) 0.8188(5) 0.3209(5) 0.0456(16) Uani 1 1 d . . .
C8 C 0.2904(13) 0.8967(5) 0.3479(5) 0.0583(19) Uani 1 1 d . . .
H8 H 0.3101 0.9346 0.4126 0.070 Uiso 1 1 calc R . .
C9 C 0.1131(12) 0.9179(5) 0.2784(5) 0.0483(17) Uani 1 1 d . . .
H9 H 0.0152 0.9703 0.2973 0.058 Uiso 1 1 calc R . .
C10 C 0.6267(13) 0.7910(6) 0.3938(5) 0.0525(17) Uani 1 1 d . . .
C11 C -0.2690(11) 0.6843(4) -0.0111(4) 0.0453(16) Uani 1 1 d . . .
H11A H -0.4435 0.6427 -0.0305 0.054 Uiso 1 1 calc R . .
H11B H -0.1949 0.6530 0.0412 0.054 Uiso 1 1 calc R . .
C12 C -0.1271(13) 0.6643(5) -0.0981(5) 0.0574(19) Uani 1 1 d . . .
H12A H -0.1923 0.7007 -0.1486 0.069 Uiso 1 1 calc R . .
H12B H 0.0502 0.7008 -0.0773 0.069 Uiso 1 1 calc R . .
C13 C -0.1494(17) 0.5384(6) -0.1409(6) 0.077(2) Uani 1 1 d . . .
H13A H -0.3259 0.5031 -0.1652 0.093 Uiso 1 1 calc R . .
H13B H -0.0945 0.5011 -0.0893 0.093 Uiso 1 1 calc R . .
C14 C 0.0038(18) 0.5168(7) -0.2235(6) 0.093(3) Uani 1 1 d . . .
H14A H -0.0172 0.5682 -0.2670 0.139 Uiso 1 1 calc R . .
H14B H -0.0541 0.4387 -0.2587 0.139 Uiso 1 1 calc R . .
H14C H 0.1793 0.5297 -0.1968 0.139 Uiso 1 1 calc R . .
C16 C 0.4758(19) 0.7960(8) 0.7016(7) 0.114(3) Uani 1 1 d . . .
H16A H 0.6540 0.8058 0.7002 0.170 Uiso 1 1 calc R . .
H16B H 0.4364 0.7690 0.7594 0.170 Uiso 1 1 calc R . .
H16C H 0.4282 0.8683 0.7019 0.170 Uiso 1 1 calc R . .
C17 C 0.4256(19) 0.6054(8) 0.5899(8) 0.115(4) Uani 1 1 d . . .
H17A H 0.3128 0.5557 0.5351 0.172 Uiso 1 1 calc R . .
H17B H 0.4288 0.5677 0.6445 0.172 Uiso 1 1 calc R . .
H17C H 0.5925 0.6230 0.5733 0.172 Uiso 1 1 calc R . .
N1 N -0.4376(9) 0.8583(4) -0.0237(4) 0.0446(13) Uani 1 1 d . . .
N2 N 0.3376(12) 0.7125(5) 0.6159(5) 0.0693(17) Uani 1 1 d . B .
O1 O 0.7103(10) 0.7024(4) 0.3722(4) 0.0774(16) Uani 1 1 d . . .
O2 O 0.6949(11) 0.8625(5) 0.4764(4) 0.0846(18) Uani 1 1 d . . .
H2 H 0.8122 0.8453 0.5080 0.127 Uiso 1 1 calc R . .
S1 S -0.1917(3) 1.01653(12) 0.11968(12) 0.0474(6) Uani 1 1 d . . .
C15 C 0.1512(18) 0.7395(9) 0.5644(7) 0.088(3) Uani 1 1 d . . .
H15 H 0.0848 0.6939 0.5031 0.106 Uiso 1 1 calc R A 1
O3 O 0.0519(19) 0.8281(9) 0.5947(7) 0.088(4) Uani 0.567(12) 1 d P B 1
O3' O 0.044(3) 0.6493(11) 0.4868(9) 0.089(5) Uani 0.433(12) 1 d P B 2
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
N1 C1 C1 122.9(7) . 2_475
N1 C1 S1 116.0(4) . .
C1 C1 S1 121.1(6) 2_475 .
C3 C2 N1 114.1(4) . .
C3 C2 C11 128.6(5) . .
N1 C2 C11 117.3(5) . .
C2 C3 C4 130.8(5) . .
C2 C3 S1 109.6(4) . .
C4 C3 S1 119.6(4) . .
C5 C4 C9 118.1(6) . .
C5 C4 C3 120.6(5) . .
C9 C4 C3 121.3(5) . .
C4 C5 C6 120.5(6) . .
C4 C5 H5 119.7 . .
C6 C5 H5 119.7 . .
C7 C6 C5 120.8(5) . .
C7 C6 H6 119.6 . .
C5 C6 H6 119.6 . .
C6 C7 C8 119.2(6) . .
C6 C7 C10 119.0(5) . .
C8 C7 C10 121.8(6) . .
C9 C8 C7 120.1(6) . .
C9 C8 H8 119.9 . .
C7 C8 H8 119.9 . .
C8 C9 C4 121.2(5) . .
C8 C9 H9 119.4 . .
C4 C9 H9 119.4 . .
O1 C10 O2 123.8(6) . .
O1 C10 C7 119.5(6) . .
O2 C10 C7 116.7(5) . .
C2 C11 C12 113.7(5) . .
C2 C11 H11A 108.8 . .
C12 C11 H11A 108.8 . .
C2 C11 H11B 108.8 . .
C12 C11 H11B 108.8 . .
H11A C11 H11B 107.7 . .
C13 C12 C11 113.5(5) . .
C13 C12 H12A 108.9 . .
C11 C12 H12A 108.9 . .
C13 C12 H12B 108.9 . .
C11 C12 H12B 108.9 . .
H12A C12 H12B 107.7 . .
C12 C13 C14 114.2(6) . .
C12 C13 H13A 108.7 . .
C14 C13 H13A 108.7 . .
C12 C13 H13B 108.7 . .
C14 C13 H13B 108.7 . .
H13A C13 H13B 107.6 . .
C13 C14 H14A 109.5 . .
C13 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C13 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
N2 C16 H16A 109.5 . .
N2 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
N2 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
N2 C17 H17A 109.5 . .
N2 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
N2 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
C1 N1 C2 111.1(5) . .
C15 N2 C16 118.1(7) . .
C15 N2 C17 124.3(8) . .
C16 N2 C17 117.5(7) . .
C10 O2 H2 109.5 . .
C1 S1 C3 89.3(3) . .
N2 C15 O3 123.7(9) . .
N2 C15 O3' 109.1(9) . .
O3 C15 O3' 125.8(10) . .
N2 C15 H15 118.2 . .
O3 C15 H15 118.2 . .
O3' C15 H15 14.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.287(7) .
C1 C1 1.469(12) 2_475
C1 S1 1.723(6) .
C2 C3 1.380(8) .
C2 N1 1.409(7) .
C2 C11 1.499(6) .
C3 C4 1.480(8) .
C3 S1 1.743(5) .
C4 C5 1.389(7) .
C4 C9 1.391(8) .
C5 C6 1.398(9) .
C5 H5 0.9300 .
C6 C7 1.372(8) .
C6 H6 0.9300 .
C7 C8 1.390(8) .
C7 C10 1.496(9) .
C8 C9 1.389(9) .
C8 H8 0.9300 .
C9 H9 0.9300 .
C10 O1 1.250(7) .
C10 O2 1.289(7) .
C11 C12 1.532(9) .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C12 C13 1.513(8) .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C13 C14 1.525(10) .
C13 H13A 0.9700 .
C13 H13B 0.9700 .
C14 H14A 0.9600 .
C14 H14B 0.9600 .
C14 H14C 0.9600 .
C16 N2 1.455(10) .
C16 H16A 0.9600 .
C16 H16B 0.9600 .
C16 H16C 0.9600 .
C17 N2 1.471(9) .
C17 H17A 0.9600 .
C17 H17B 0.9600 .
C17 H17C 0.9600 .
N2 C15 1.309(10) .
O2 H2 0.8200 .
C15 O3 1.322(11) .
C15 O3' 1.384(14) .
C15 H15 0.9300 .
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
N1 C2 C3 C4 177.2(6) .
C11 C2 C3 C4 -0.8(11) .
N1 C2 C3 S1 -0.7(6) .
C11 C2 C3 S1 -178.7(5) .
C2 C3 C4 C5 35.0(10) .
S1 C3 C4 C5 -147.3(5) .
C2 C3 C4 C9 -145.3(7) .
S1 C3 C4 C9 32.4(8) .
C9 C4 C5 C6 3.3(9) .
C3 C4 C5 C6 -177.0(6) .
C4 C5 C6 C7 -2.3(10) .
C5 C6 C7 C8 0.1(10) .
C5 C6 C7 C10 179.4(6) .
C6 C7 C8 C9 1.0(10) .
C10 C7 C8 C9 -178.3(6) .
C7 C8 C9 C4 0.1(10) .
C5 C4 C9 C8 -2.2(9) .
C3 C4 C9 C8 178.1(6) .
C6 C7 C10 O1 -16.6(10) .
C8 C7 C10 O1 162.7(7) .
C6 C7 C10 O2 162.8(6) .
C8 C7 C10 O2 -17.9(10) .
C3 C2 C11 C12 -101.2(7) .
N1 C2 C11 C12 80.8(7) .
C2 C11 C12 C13 -175.6(6) .
C11 C12 C13 C14 -176.4(7) .
C1 C1 N1 C2 -179.0(7) 2_475
S1 C1 N1 C2 1.4(7) .
C3 C2 N1 C1 -0.4(7) .
C11 C2 N1 C1 177.9(5) .
N1 C1 S1 C3 -1.5(5) .
C1 C1 S1 C3 178.9(7) 2_475
C2 C3 S1 C1 1.1(4) .
C4 C3 S1 C1 -177.0(5) .
C16 N2 C15 O3 -12.7(14) .
C17 N2 C15 O3 170.6(10) .
C16 N2 C15 O3' -179.8(9) .
C17 N2 C15 O3' 3.5(13) .
