#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/71/7117194.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_7117194
loop_
_publ_author_name
'Roop Shikha Singh'
'Rakesh Kumar Gupta'
'Rajendra Prasad Paitandi'
'Mrigendra Dubey'
'Gunjan Sharma'
'Biplob Koch'
'Daya Shankar Pandey'
_publ_section_title
;
 Morphological tuning via structural modulations in AIE luminogens with
 the minimum number of possible variables and their use in live cell
 imaging
;
_journal_name_full               Chem.Commun.
_journal_page_first              9125
_journal_paper_doi               10.1039/C5cc02488A
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C20 H16 B F2 N3 S, 0.5(C6 H14)'
_chemical_formula_sum            'C23 H23 B F2 N3 S'
_chemical_formula_weight         422.31
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2014-12-17 deposited with the CCDC.
2015-04-09 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 109.759(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.3271(10)
_cell_length_b                   8.3270(4)
_cell_length_c                   16.9926(8)
_cell_measurement_reflns_used    5023
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.87
_cell_measurement_theta_min      2.55
_cell_volume                     2174.2(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SIR-92 (Altomare et al.,1993)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_sigmaI/netI    0.0305
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            17292
_diffrn_reflns_theta_full        26.78
_diffrn_reflns_theta_max         26.78
_diffrn_reflns_theta_min         1.50
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.180
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_correction_T_min  0.958
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/2 - Bruker AXS area detector scaling and absorption correction  
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             884
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4650
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.0642
_refine_ls_R_factor_gt           0.0450
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0801P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1312
_refine_ls_wR_factor_ref         0.1410
_reflns_number_gt                3421
_reflns_number_total             4650
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc02488a2.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7117194
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.83590(14) 0.9667(2) 0.81309(11) 0.0523(5) Uani 1 1 d . . .
H1 H 0.8594 0.9205 0.7757 0.063 Uiso 1 1 calc R . .
C2 C 0.75314(15) 0.9376(3) 0.81389(12) 0.0632(6) Uani 1 1 d . . .
H2 H 0.7118 0.8704 0.7778 0.076 Uiso 1 1 calc R . .
C3 C 0.74304(13) 1.0269(3) 0.87825(11) 0.0567(5) Uani 1 1 d . . .
H3 H 0.6937 1.0308 0.8939 0.068 Uiso 1 1 calc R . .
C4 C 0.82108(11) 1.1108(2) 0.91592(10) 0.0421(4) Uani 1 1 d . . .
C5 C 0.84793(11) 1.2129(2) 0.98515(9) 0.0379(4) Uani 1 1 d . . .
C6 C 0.93244(11) 1.27044(19) 1.01501(9) 0.0362(4) Uani 1 1 d . . .
C7 C 0.97796(11) 1.3612(2) 1.08708(10) 0.0418(4) Uani 1 1 d . . .
H7 H 0.9545 1.4044 1.1253 0.050 Uiso 1 1 calc R . .
C8 C 1.06195(12) 1.3738(2) 1.09025(11) 0.0484(5) Uani 1 1 d . . .
H8 H 1.1068 1.4260 1.1312 0.058 Uiso 1 1 calc R . .
C9 C 1.06821(11) 1.2934(2) 1.02035(10) 0.0446(4) Uani 1 1 d . . .
H9 H 1.1189 1.2847 1.0072 0.054 Uiso 1 1 calc R . .
C10 C 0.78577(11) 1.2571(2) 1.02872(10) 0.0378(4) Uani 1 1 d . . .
C11 C 0.71745(10) 1.3696(2) 0.99177(9) 0.0378(4) Uani 1 1 d . . .
C12 C 0.66350(10) 1.3436(2) 1.09983(10) 0.0378(4) Uani 1 1 d . . .
C13 C 0.60068(11) 1.3869(2) 1.13547(11) 0.0461(4) Uani 1 1 d . . .
H13 H 0.5544 1.4525 1.1060 0.055 Uiso 1 1 calc R . .
C14 C 0.60743(12) 1.3327(2) 1.21338(11) 0.0486(5) Uani 1 1 d . . .
H14 H 0.5653 1.3624 1.2362 0.058 Uiso 1 1 calc R . .
C15 C 0.67628(13) 1.2336(2) 1.25972(11) 0.0506(5) Uani 1 1 d . . .
C16 C 0.73602(13) 1.1856(2) 1.22450(11) 0.0524(5) Uani 1 1 d . . .
H16 H 0.7807 1.1167 1.2540 0.063 Uiso 1 1 calc R . .
C17 C 0.73123(11) 1.2390(2) 1.14367(10) 0.0407(4) Uani 1 1 d . . .
C18 C 0.79217(11) 1.1948(2) 1.10473(10) 0.0434(4) Uani 1 1 d . . .
H18 H 0.8367 1.1232 1.1311 0.052 Uiso 1 1 calc R . .
C19 C 0.63283(16) 1.6093(3) 0.88473(15) 0.0806(8) Uani 1 1 d . . .
H19A H 0.6264 1.6714 0.8354 0.121 Uiso 1 1 calc R . .
H19B H 0.6471 1.6792 0.9324 0.121 Uiso 1 1 calc R . .
H19C H 0.5793 1.5545 0.8785 0.121 Uiso 1 1 calc R . .
C20 C 0.68326(17) 1.1827(3) 1.34745(13) 0.0787(8) Uani 1 1 d . . .
H20A H 0.6309 1.1283 1.3458 0.118 Uiso 1 1 calc R . .
H20B H 0.6913 1.2759 1.3825 0.118 Uiso 1 1 calc R . .
H20C H 0.7320 1.1117 1.3695 0.118 Uiso 1 1 calc R . .
C21 C 0.5136(2) 0.0172(4) 0.96201(17) 0.0949(9) Uani 1 1 d . . .
H21A H 0.5723 0.0602 0.9815 0.114 Uiso 1 1 calc R . .
H21B H 0.5151 -0.0835 0.9339 0.114 Uiso 1 1 calc R . .
C22 C 0.4567(2) 0.1308(5) 0.9003(2) 0.1201(12) Uani 1 1 d . . .
H22A H 0.4547 0.2316 0.9281 0.144 Uiso 1 1 calc R . .
H22B H 0.3981 0.0875 0.8797 0.144 Uiso 1 1 calc R . .
C23 C 0.4869(3) 0.1633(5) 0.8258(2) 0.1261(12) Uani 1 1 d . . .
H23A H 0.4469 0.2353 0.7876 0.189 Uiso 1 1 calc R . .
H23B H 0.4891 0.0641 0.7978 0.189 Uiso 1 1 calc R . .
H23C H 0.5438 0.2110 0.8453 0.189 Uiso 1 1 calc R . .
N1 N 0.87795(10) 1.07052(18) 0.87360(8) 0.0427(4) Uani 1 1 d . . .
N2 N 0.99180(9) 1.23117(16) 0.97511(8) 0.0371(3) Uani 1 1 d . . .
N3 N 0.65784(8) 1.40853(18) 1.02391(8) 0.0418(3) Uani 1 1 d . . .
B1 B 0.96639(13) 1.1525(2) 0.88764(11) 0.0398(4) Uani 1 1 d . . .
F1 F 0.95626(8) 1.26965(12) 0.82669(6) 0.0545(3) Uani 1 1 d . . .
F2 F 1.02823(7) 1.04393(13) 0.88344(7) 0.0573(3) Uani 1 1 d . . .
S1 S 0.71723(3) 1.46668(7) 0.89929(3) 0.05680(19) 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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 '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'
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 C2 110.81(18) . .
N1 C1 H1 124.6 . .
C2 C1 H1 124.6 . .
C1 C2 C3 107.12(18) . .
C1 C2 H2 126.4 . .
C3 C2 H2 126.4 . .
C2 C3 C4 107.26(18) . .
C2 C3 H3 126.4 . .
C4 C3 H3 126.4 . .
N1 C4 C5 120.46(15) . .
N1 C4 C3 107.77(15) . .
C5 C4 C3 131.70(16) . .
C6 C5 C4 120.64(15) . .
C6 C5 C10 119.60(15) . .
C4 C5 C10 119.75(15) . .
C5 C6 N2 120.67(15) . .
C5 C6 C7 131.90(15) . .
N2 C6 C7 107.29(14) . .
C8 C7 C6 107.64(15) . .
C8 C7 H7 126.2 . .
C6 C7 H7 126.2 . .
C7 C8 C9 107.01(16) . .
C7 C8 H8 126.5 . .
C9 C8 H8 126.5 . .
N2 C9 C8 110.75(15) . .
N2 C9 H9 124.6 . .
C8 C9 H9 124.6 . .
C18 C10 C11 117.65(15) . .
C18 C10 C5 122.01(15) . .
C11 C10 C5 120.33(14) . .
N3 C11 C10 124.03(14) . .
N3 C11 S1 118.68(12) . .
C10 C11 S1 117.23(12) . .
N3 C12 C13 118.54(15) . .
N3 C12 C17 122.17(14) . .
C13 C12 C17 119.26(14) . .
C14 C13 C12 120.13(16) . .
C14 C13 H13 119.9 . .
C12 C13 H13 119.9 . .
C13 C14 C15 121.65(16) . .
C13 C14 H14 119.2 . .
C15 C14 H14 119.2 . .
C16 C15 C14 118.82(16) . .
C16 C15 C20 121.44(18) . .
C14 C15 C20 119.75(17) . .
C15 C16 C17 121.23(17) . .
C15 C16 H16 119.4 . .
C17 C16 H16 119.4 . .
C12 C17 C18 117.62(14) . .
C12 C17 C16 118.82(15) . .
C18 C17 C16 123.55(16) . .
C10 C18 C17 120.20(16) . .
C10 C18 H18 119.9 . .
C17 C18 H18 119.9 . .
S1 C19 H19A 109.5 . .
S1 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
S1 C19 H19C 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
C15 C20 H20A 109.5 . .
C15 C20 H20B 109.5 . .
H20A C20 H20B 109.5 . .
C15 C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
C22 C21 C21 115.2(4) . 3_657
C22 C21 H21A 108.5 . .
C21 C21 H21A 108.5 3_657 .
C22 C21 H21B 108.5 . .
C21 C21 H21B 108.5 3_657 .
H21A C21 H21B 107.5 . .
C21 C22 C23 113.5(3) . .
C21 C22 H22A 108.9 . .
C23 C22 H22A 108.9 . .
C21 C22 H22B 108.9 . .
C23 C22 H22B 108.9 . .
H22A C22 H22B 107.7 . .
C22 C23 H23A 109.5 . .
C22 C23 H23B 109.5 . .
H23A C23 H23B 109.5 . .
C22 C23 H23C 109.5 . .
H23A C23 H23C 109.5 . .
H23B C23 H23C 109.5 . .
C1 N1 C4 107.04(15) . .
C1 N1 B1 127.90(15) . .
C4 N1 B1 124.48(14) . .
C9 N2 C6 107.31(14) . .
C9 N2 B1 127.94(14) . .
C6 N2 B1 124.12(14) . .
C11 N3 C12 118.14(14) . .
F2 B1 F1 109.09(14) . .
F2 B1 N1 111.50(15) . .
F1 B1 N1 109.03(15) . .
F2 B1 N2 111.42(14) . .
F1 B1 N2 110.14(15) . .
N1 B1 N2 105.61(12) . .
C11 S1 C19 101.46(9) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.341(2) .
C1 C2 1.377(3) .
C1 H1 0.9300 .
C2 C3 1.378(3) .
C2 H2 0.9300 .
C3 C4 1.404(2) .
C3 H3 0.9300 .
C4 N1 1.394(2) .
C4 C5 1.396(2) .
C5 C6 1.385(2) .
C5 C10 1.491(2) .
C6 N2 1.396(2) .
C6 C7 1.417(2) .
C7 C8 1.358(3) .
C7 H7 0.9300 .
C8 C9 1.397(2) .
C8 H8 0.9300 .
C9 N2 1.330(2) .
C9 H9 0.9300 .
C10 C18 1.363(2) .
C10 C11 1.429(2) .
C11 N3 1.308(2) .
C11 S1 1.7662(16) .
C12 N3 1.373(2) .
C12 C13 1.403(2) .
C12 C17 1.407(2) .
C13 C14 1.367(2) .
C13 H13 0.9300 .
C14 C15 1.402(3) .
C14 H14 0.9300 .
C15 C16 1.365(3) .
C15 C20 1.517(3) .
C16 C17 1.420(2) .
C16 H16 0.9300 .
C17 C18 1.417(2) .
C18 H18 0.9300 .
C19 S1 1.772(2) .
C19 H19A 0.9600 .
C19 H19B 0.9600 .
C19 H19C 0.9600 .
C20 H20A 0.9600 .
C20 H20B 0.9600 .
C20 H20C 0.9600 .
C21 C22 1.483(4) .
C21 C21 1.528(6) 3_657
C21 H21A 0.9700 .
C21 H21B 0.9700 .
C22 C23 1.530(5) .
C22 H22A 0.9700 .
C22 H22B 0.9700 .
C23 H23A 0.9600 .
C23 H23B 0.9600 .
C23 H23C 0.9600 .
N1 B1 1.541(2) .
N2 B1 1.547(2) .
B1 F2 1.375(2) .
B1 F1 1.391(2) .
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
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
N1 C1 C2 C3 -0.3(2) . . . .
C1 C2 C3 C4 0.3(2) . . . .
C2 C3 C4 N1 -0.2(2) . . . .
C2 C3 C4 C5 -177.15(19) . . . .
N1 C4 C5 C6 -2.7(2) . . . .
C3 C4 C5 C6 173.99(19) . . . .
N1 C4 C5 C10 178.89(15) . . . .
C3 C4 C5 C10 -4.4(3) . . . .
C4 C5 C6 N2 1.8(2) . . . .
C10 C5 C6 N2 -179.78(14) . . . .
C4 C5 C6 C7 -173.27(17) . . . .
C10 C5 C6 C7 5.2(3) . . . .
C5 C6 C7 C8 174.89(18) . . . .
N2 C6 C7 C8 -0.64(19) . . . .
C6 C7 C8 C9 0.7(2) . . . .
C7 C8 C9 N2 -0.6(2) . . . .
C6 C5 C10 C18 -72.2(2) . . . .
C4 C5 C10 C18 106.2(2) . . . .
C6 C5 C10 C11 106.85(19) . . . .
C4 C5 C10 C11 -74.7(2) . . . .
C18 C10 C11 N3 -4.4(3) . . . .
C5 C10 C11 N3 176.48(16) . . . .
C18 C10 C11 S1 172.93(13) . . . .
C5 C10 C11 S1 -6.2(2) . . . .
N3 C12 C13 C14 -175.80(16) . . . .
C17 C12 C13 C14 2.6(3) . . . .
C12 C13 C14 C15 0.0(3) . . . .
C13 C14 C15 C16 -2.5(3) . . . .
C13 C14 C15 C20 177.3(2) . . . .
C14 C15 C16 C17 2.3(3) . . . .
C20 C15 C16 C17 -177.4(2) . . . .
N3 C12 C17 C18 -3.2(3) . . . .
C13 C12 C17 C18 178.44(17) . . . .
N3 C12 C17 C16 175.65(17) . . . .
C13 C12 C17 C16 -2.7(3) . . . .
C15 C16 C17 C12 0.2(3) . . . .
C15 C16 C17 C18 179.03(19) . . . .
C11 C10 C18 C17 1.5(3) . . . .
C5 C10 C18 C17 -179.44(16) . . . .
C12 C17 C18 C10 2.1(3) . . . .
C16 C17 C18 C10 -176.77(18) . . . .
C21 C21 C22 C23 179.3(3) 3_657 . . .
C2 C1 N1 C4 0.2(2) . . . .
C2 C1 N1 B1 -171.23(17) . . . .
C5 C4 N1 C1 177.34(16) . . . .
C3 C4 N1 C1 -0.05(19) . . . .
C5 C4 N1 B1 -10.8(2) . . . .
C3 C4 N1 B1 171.80(16) . . . .
C8 C9 N2 C6 0.16(19) . . . .
C8 C9 N2 B1 171.32(16) . . . .
C5 C6 N2 C9 -175.85(15) . . . .
C7 C6 N2 C9 0.29(18) . . . .
C5 C6 N2 B1 12.6(2) . . . .
C7 C6 N2 B1 -171.29(14) . . . .
C10 C11 N3 C12 3.3(3) . . . .
S1 C11 N3 C12 -173.96(12) . . . .
C13 C12 N3 C11 178.92(16) . . . .
C17 C12 N3 C11 0.6(2) . . . .
C1 N1 B1 F2 -47.7(2) . . . .
C4 N1 B1 F2 142.23(15) . . . .
C1 N1 B1 F1 72.8(2) . . . .
C4 N1 B1 F1 -97.26(18) . . . .
C1 N1 B1 N2 -168.84(16) . . . .
C4 N1 B1 N2 21.1(2) . . . .
C9 N2 B1 F2 47.1(2) . . . .
C6 N2 B1 F2 -143.13(15) . . . .
C9 N2 B1 F1 -74.1(2) . . . .
C6 N2 B1 F1 95.67(18) . . . .
C9 N2 B1 N1 168.29(16) . . . .
C6 N2 B1 N1 -21.9(2) . . . .
N3 C11 S1 C19 4.80(18) . . . .
C10 C11 S1 C19 -172.68(15) . . . .
