#------------------------------------------------------------------------------
#$Date: 2018-04-04 04:38:23 +0300 (Wed, 04 Apr 2018) $
#$Revision: 207223 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/04/7230411.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_7230411
loop_
_publ_author_name
'Yu, Chin-Yang'
'Hsu, Chia-Chieh'
'Weng, Hsi-Chen'
_publ_section_title
;
 Synthesis, characterization, aggregation-induced emission,
 solvatochromism and mechanochromism of fluorinated benzothiadiazole
 bonded to tetraphenylethenes
;
_journal_issue                   23
_journal_name_full               'RSC Advances'
_journal_page_first              12619
_journal_paper_doi               10.1039/C8RA01448E
_journal_volume                  8
_journal_year                    2018
_chemical_formula_moiety         'C20 H20 F2 N2 S1'
_chemical_formula_sum            'C60 H42 Cl4 F2 N2 S'
_chemical_formula_weight         1002.82
_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
_audit_update_record
;
2018-02-10 deposited with the CCDC.
2018-03-28 downloaded from the CCDC.
;
_cell_angle_alpha                93.116(4)
_cell_angle_beta                 97.317(4)
_cell_angle_gamma                115.044(4)
_cell_formula_units_Z            1
_cell_length_a                   9.1294(12)
_cell_length_b                   9.2735(13)
_cell_length_c                   16.422(2)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     1240.2(3)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_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  0.0585
_diffrn_reflns_av_sigmaI/netI    0.0301
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            32746
_diffrn_reflns_theta_full        25.04
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         2.50
_exptl_absorpt_coefficient_mu    0.331
_exptl_absorpt_correction_T_max  0.9645
_exptl_absorpt_correction_T_min  0.8039
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             518
_exptl_crystal_size_max          0.69
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.436
_refine_diff_density_min         -0.530
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         4314
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0447
_refine_ls_shift/su_max          0.027
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0440P)²+0.9596P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1107
_refine_ls_wR_factor_ref         0.1147
_reflns_number_gt                3948
_reflns_number_total             4314
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8ra01448e2.cif
_cod_data_source_block           d19031
_cod_database_code               7230411
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 0.0310(2) 0.3754(2) 0.47248(11) 0.0243(4) Uani 1 1 d . . .
C2 C 0.1356(2) 0.4718(2) 0.54367(10) 0.0239(4) Uani 1 1 d . . .
C3 C -0.1006(2) 0.4019(2) 0.43059(10) 0.0244(4) Uani 1 1 d . . .
C4 C 0.2718(2) 0.4423(2) 0.58649(10) 0.0250(4) Uani 1 1 d . . .
C5 C 0.2473(2) 0.2884(2) 0.60289(11) 0.0262(4) Uani 1 1 d . B .
H5 H 0.1420 0.2011 0.5870 0.031 Uiso 1 1 calc R . .
C6 C 0.3756(2) 0.2620(2) 0.64219(11) 0.0259(4) Uani 1 1 d . . .
H6 H 0.3568 0.1563 0.6525 0.031 Uiso 1 1 calc R B .
C7 C 0.5321(2) 0.3872(2) 0.66698(10) 0.0236(4) Uani 1 1 d . B .
C8 C 0.5559(2) 0.5398(2) 0.64916(12) 0.0298(4) Uani 1 1 d . . .
H8 H 0.6618 0.6266 0.6640 0.036 Uiso 1 1 calc R B .
C9 C 0.4279(2) 0.5674(2) 0.61019(12) 0.0304(4) Uani 1 1 d . B .
H9 H 0.4470 0.6730 0.5995 0.037 Uiso 1 1 calc R . .
C10 C 0.6686(2) 0.3543(2) 0.70811(10) 0.0239(4) Uani 1 1 d . . .
C11 C 0.6846(2) 0.2154(2) 0.66728(11) 0.0242(4) Uani 1 1 d . B .
C12 C 0.6799(2) 0.1992(2) 0.58210(11) 0.0307(4) Uani 1 1 d . . .
H12 H 0.6603 0.2736 0.5502 0.037 Uiso 1 1 calc R B .
C13 C 0.7036(3) 0.0762(2) 0.54312(13) 0.0394(5) Uani 1 1 d . B .
H13 H 0.7012 0.0674 0.4850 0.047 Uiso 1 1 calc R . .
C14 C 0.7306(3) -0.0336(2) 0.58873(15) 0.0437(5) Uani 1 1 d . . .
H14 H 0.7491 -0.1168 0.5624 0.052 Uiso 1 1 calc R B .
C15 C 0.7305(3) -0.0213(2) 0.67278(15) 0.0452(5) Uani 1 1 d . B .
H15 H 0.7470 -0.0978 0.7042 0.054 Uiso 1 1 calc R . .
C16 C 0.7067(2) 0.1007(2) 0.71183(12) 0.0342(4) Uani 1 1 d . . .
H16 H 0.7053 0.1065 0.7696 0.041 Uiso 1 1 calc R B .
C17 C 0.7730(2) 0.4451(2) 0.77683(10) 0.0236(4) Uani 1 1 d . B .
C18 C 0.9157(2) 0.4175(2) 0.81418(10) 0.0236(4) Uani 1 1 d . . .
C19 C 1.0364(2) 0.4209(2) 0.76969(11) 0.0308(4) Uani 1 1 d . B .
H19 H 1.0311 0.4448 0.7142 0.037 Uiso 1 1 calc R . .
C20 C 1.1642(2) 0.3901(3) 0.80510(12) 0.0388(5) Uani 1 1 d . . .
H20 H 1.2472 0.3948 0.7743 0.047 Uiso 1 1 calc R B .
C21 C 1.1714(2) 0.3523(3) 0.88547(12) 0.0378(5) Uani 1 1 d . B .
H21 H 1.2575 0.3279 0.9093 0.045 Uiso 1 1 calc R . .
C22 C 1.0538(2) 0.3500(2) 0.93074(11) 0.0349(4) Uani 1 1 d . . .
H22 H 1.0588 0.3244 0.9860 0.042 Uiso 1 1 calc R B .
C23 C 0.9281(2) 0.3850(2) 0.89582(11) 0.0294(4) Uani 1 1 d . B .
H23 H 0.8493 0.3867 0.9280 0.035 Uiso 1 1 calc R . .
C24 C 0.7538(2) 0.5764(2) 0.82433(11) 0.0271(4) Uani 1 1 d . . .
C25 C 0.8773(3) 0.7314(2) 0.83516(12) 0.0361(4) Uani 1 1 d . B .
H25 H 0.9714 0.7548 0.8098 0.043 Uiso 1 1 calc R . .
C26 C 0.8649(3) 0.8534(3) 0.88278(14) 0.0480(6) Uani 1 1 d . . .
H26 H 0.9495 0.9597 0.8891 0.058 Uiso 1 1 calc R B .
C27 C 0.7300(3) 0.8198(3) 0.92078(14) 0.0529(7) Uani 1 1 d . B .
H27 H 0.7215 0.9027 0.9536 0.064 Uiso 1 1 calc R . .
C28 C 0.6074(3) 0.6659(3) 0.91105(14) 0.0492(6) Uani 1 1 d . . .
H28 H 0.5148 0.6426 0.9377 0.059 Uiso 1 1 calc R B .
C29 C 0.6180(2) 0.5445(3) 0.86272(13) 0.0372(5) Uani 1 1 d . B .
H29 H 0.5319 0.4389 0.8558 0.045 Uiso 1 1 calc R . .
C30 C 0.6326(4) 0.1193(4) 0.14538(19) 0.0757(9) Uani 1 1 d . . .
H30A H 0.5140 0.0909 0.1398 0.091 Uiso 1 1 calc R . .
H30B H 0.6910 0.2079 0.1909 0.091 Uiso 1 1 calc R . .
F1 F -0.1767(19) 0.297(2) 0.3672(10) 0.0265(19) Uani 0.50 1 d P A 2
F1' F 0.0487(12) 0.2529(12) 0.4379(6) 0.038(3) Uani 0.50 1 d P B 3
N1 N 0.0483(17) 0.2506(15) 0.4353(8) 0.028(4) Uani 0.50 1 d P B 1
N1' N -0.202(3) 0.298(3) 0.3558(15) 0.026(2) Uani 0.50 1 d P B 1
S1 S -0.09386(12) 0.17654(11) 0.35575(6) 0.0313(2) Uani 0.50 1 d P B 1
Cl1 Cl 0.70003(9) 0.18373(8) 0.05429(4) 0.0619(2) Uani 1 1 d . . .
Cl2 Cl 0.66510(12) -0.04645(10) 0.17032(6) 0.0881(3) Uani 1 1 d . . .
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'
F F 0.0171 0.0103 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
F1' C1 N1 1.3(10) . .
F1' C1 C2 122.1(4) . .
N1 C1 C2 123.1(6) . .
F1' C1 C3 114.6(4) . .
N1 C1 C3 113.6(6) . .
C2 C1 C3 123.35(17) . .
C3 C2 C1 113.66(16) 2_566 .
C3 C2 C4 123.73(15) 2_566 .
C1 C2 C4 122.60(16) . .
F1 C3 C2 126.4(6) . 2_566
F1 C3 C1 110.6(6) . .
C2 C3 C1 122.99(16) 2_566 .
F1 C3 N1' 9.4(15) . .
C2 C3 N1' 117.0(9) 2_566 .
C1 C3 N1' 120.0(9) . .
C9 C4 C5 118.33(16) . .
C9 C4 C2 120.76(16) . .
C5 C4 C2 120.91(15) . .
C6 C5 C4 120.42(16) . .
C6 C5 H5 119.8 . .
C4 C5 H5 119.8 . .
C5 C6 C7 121.55(16) . .
C5 C6 H6 119.2 . .
C7 C6 H6 119.2 . .
C8 C7 C6 117.59(15) . .
C8 C7 C10 122.14(15) . .
C6 C7 C10 120.23(15) . .
C9 C8 C7 121.22(17) . .
C9 C8 H8 119.4 . .
C7 C8 H8 119.4 . .
C8 C9 C4 120.86(17) . .
C8 C9 H9 119.6 . .
C4 C9 H9 119.6 . .
C17 C10 C11 121.80(15) . .
C17 C10 C7 122.92(15) . .
C11 C10 C7 115.27(14) . .
C16 C11 C12 118.18(17) . .
C16 C11 C10 122.07(16) . .
C12 C11 C10 119.75(15) . .
C13 C12 C11 120.96(18) . .
C13 C12 H12 119.5 . .
C11 C12 H12 119.5 . .
C14 C13 C12 120.03(19) . .
C14 C13 H13 120.0 . .
C12 C13 H13 120.0 . .
C15 C14 C13 119.39(18) . .
C15 C14 H14 120.3 . .
C13 C14 H14 120.3 . .
C14 C15 C16 120.79(19) . .
C14 C15 H15 119.6 . .
C16 C15 H15 119.6 . .
C15 C16 C11 120.59(19) . .
C15 C16 H16 119.7 . .
C11 C16 H16 119.7 . .
C10 C17 C18 122.38(15) . .
C10 C17 C24 123.91(15) . .
C18 C17 C24 113.66(14) . .
C19 C18 C23 118.33(16) . .
C19 C18 C17 122.19(15) . .
C23 C18 C17 119.47(15) . .
C20 C19 C18 120.88(17) . .
C20 C19 H19 119.6 . .
C18 C19 H19 119.6 . .
C19 C20 C21 119.98(18) . .
C19 C20 H20 120.0 . .
C21 C20 H20 120.0 . .
C22 C21 C20 119.91(17) . .
C22 C21 H21 120.0 . .
C20 C21 H21 120.0 . .
C21 C22 C23 120.01(17) . .
C21 C22 H22 120.0 . .
C23 C22 H22 120.0 . .
C22 C23 C18 120.82(17) . .
C22 C23 H23 119.6 . .
C18 C23 H23 119.6 . .
C25 C24 C29 118.69(18) . .
C25 C24 C17 120.06(17) . .
C29 C24 C17 121.13(17) . .
C24 C25 C26 120.7(2) . .
C24 C25 H25 119.6 . .
C26 C25 H25 119.6 . .
C27 C26 C25 119.9(2) . .
C27 C26 H26 120.0 . .
C25 C26 H26 120.0 . .
C28 C27 C26 119.8(2) . .
C28 C27 H27 120.1 . .
C26 C27 H27 120.1 . .
C27 C28 C29 120.5(2) . .
C27 C28 H28 119.7 . .
C29 C28 H28 119.7 . .
C28 C29 C24 120.3(2) . .
C28 C29 H29 119.8 . .
C24 C29 H29 119.8 . .
Cl1 C30 Cl2 112.14(17) . .
Cl1 C30 H30A 109.2 . .
Cl2 C30 H30A 109.2 . .
Cl1 C30 H30B 109.2 . .
Cl2 C30 H30B 109.2 . .
H30A C30 H30B 107.9 . .
C1 N1 S1 106.5(8) . .
C3 N1' S1 94.6(10) . .
N1 S1 N1' 105.3(8) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 F1' 1.322(9) .
C1 N1 1.357(10) .
C1 C2 1.399(3) .
C1 C3 1.426(2) .
C2 C3 1.397(2) 2_566
C2 C4 1.483(2) .
C3 F1 1.285(16) .
C3 C2 1.397(2) 2_566
C3 N1' 1.46(2) .
C4 C9 1.392(3) .
C4 C5 1.396(2) .
C5 C6 1.384(2) .
C5 H5 0.9500 .
C6 C7 1.396(2) .
C6 H6 0.9500 .
C7 C8 1.392(2) .
C7 C10 1.494(2) .
C8 C9 1.386(2) .
C8 H8 0.9500 .
C9 H9 0.9500 .
C10 C17 1.354(2) .
C10 C11 1.490(2) .
C11 C16 1.391(3) .
C11 C12 1.392(3) .
C12 C13 1.387(3) .
C12 H12 0.9500 .
C13 C14 1.381(3) .
C13 H13 0.9500 .
C14 C15 1.379(3) .
C14 H14 0.9500 .
C15 C16 1.380(3) .
C15 H15 0.9500 .
C16 H16 0.9500 .
C17 C18 1.494(2) .
C17 C24 1.495(2) .
C18 C19 1.389(2) .
C18 C23 1.391(2) .
C19 C20 1.382(3) .
C19 H19 0.9500 .
C20 C21 1.385(3) .
C20 H20 0.9500 .
C21 C22 1.375(3) .
C21 H21 0.9500 .
C22 C23 1.386(3) .
C22 H22 0.9500 .
C23 H23 0.9500 .
C24 C25 1.385(3) .
C24 C29 1.390(3) .
C25 C26 1.392(3) .
C25 H25 0.9500 .
C26 C27 1.377(4) .
C26 H26 0.9500 .
C27 C28 1.376(4) .
C27 H27 0.9500 .
C28 C29 1.386(3) .
C28 H28 0.9500 .
C29 H29 0.9500 .
C30 Cl1 1.730(3) .
C30 Cl2 1.744(3) .
C30 H30A 0.9900 .
C30 H30B 0.9900 .
N1 S1 1.606(14) .
N1' S1 1.79(2) .
