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#$Date: 2025-08-19 00:06:14 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301780 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/73/1557386.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_1557386
loop_
_publ_author_name
'Jyothi, Mane'
'Annadhasan, Mari'
'Vinay Pradeep, Vuppu'
'Chandrasekar, Rajadurai'
_publ_section_title
;
 Direct micro-scale monitoring of molecular aggregation, its growth and
 diffusion via aggregation-induced emission.
;
_journal_issue                   11
_journal_name_full               'Soft matter'
_journal_page_first              2664
_journal_page_last               2668
_journal_paper_doi               10.1039/d0sm00108b
_journal_volume                  16
_journal_year                    2020
_chemical_formula_moiety         'C23 H12 Br F6 N'
_chemical_formula_sum            'C23 H12 Br F6 N'
_chemical_formula_weight         496.25
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-12-13 deposited with the CCDC.	2020-02-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.113(9)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.327(4)
_cell_length_b                   9.854(2)
_cell_length_c                   28.274(7)
_cell_measurement_reflns_used    4879
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      22.88
_cell_measurement_theta_min      2.48
_cell_volume                     4141.4(17)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1168
_diffrn_reflns_av_unetI/netI     0.0730
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            29508
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.453
_diffrn_reflns_theta_min         2.480
_exptl_absorpt_coefficient_mu    2.048
_exptl_absorpt_correction_T_max  0.7912
_exptl_absorpt_correction_T_min  0.7094
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.592
_exptl_crystal_description       block
_exptl_crystal_F_000             1968
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.747
_refine_diff_density_min         -0.516
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       0.0038(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4256
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.1443
_refine_ls_R_factor_gt           0.0736
_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)+(0.0688P)²+21.2989P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1628
_refine_ls_wR_factor_ref         0.1931
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2414
_reflns_number_total             4256
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sm00108b1.cif
_cod_data_source_block           shelx
_cod_depositor_comments          'Adding full bibliography for 1557386.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               1557386
_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   0.709
_shelx_estimated_absorpt_t_max   0.791
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.21501(6) 1.42393(7) -0.25866(2) 0.0824(4) Uani 1 1 d . . . . .
F7 F -0.0281(4) 0.4314(6) 0.1884(2) 0.130(2) Uani 1 1 d . . . . .
F8 F 0.0636(3) 0.2757(7) 0.2099(2) 0.149(3) Uani 1 1 d . . . . .
F9 F -0.0450(3) 0.2573(6) 0.14754(19) 0.1195(18) Uani 1 1 d . . . . .
F10 F 0.3483(4) 0.4203(11) 0.0966(3) 0.266(6) Uani 1 1 d . . . . .
F11 F 0.3564(4) 0.4093(11) 0.1661(4) 0.231(5) Uani 1 1 d . . . . .
F12 F 0.3259(4) 0.2509(7) 0.1299(4) 0.191(4) Uani 1 1 d . . . . .
C1 C -0.2048(4) 1.0007(6) -0.0636(2) 0.0617(17) Uani 1 1 d . . . . .
C1I C -0.1081(5) 1.2377(7) -0.1931(2) 0.0735(19) Uani 1 1 d . . . . .
H1I H -0.0640 1.2592 -0.2093 0.088 Uiso 1 1 calc R U . . .
C2N C -0.1914(4) 1.2954(6) -0.20743(19) 0.0541(15) Uani 1 1 d . . . . .
C3B C -0.2555(4) 1.2619(6) -0.1843(2) 0.0644(17) Uani 1 1 d . . . . .
H3B H -0.3124 1.3005 -0.1941 0.077 Uiso 1 1 calc R U . . .
C4O C -0.2368(4) 1.1705(6) -0.1461(2) 0.0553(15) Uani 1 1 d . . . . .
H4O H -0.2818 1.1486 -0.1305 0.066 Uiso 1 1 calc R U . . .
C5 C -0.1539(3) 1.1110(5) -0.13050(19) 0.0429(13) Uani 1 1 d . . . . .
C6X C -0.0893(4) 1.1472(7) -0.1545(2) 0.0687(18) Uani 1 1 d . . . . .
H6X H -0.0319 1.1103 -0.1445 0.082 Uiso 1 1 calc R U . . .
C7T C -0.1348(3) 1.0134(5) -0.08927(18) 0.0406(12) Uani 1 1 d . . . . .
C8K C -0.0586(4) 0.9427(5) -0.07522(18) 0.0432(12) Uani 1 1 d . . . . .
H8K H -0.0173 0.9608 -0.0936 0.052 Uiso 1 1 calc R U . . .
C9D C -0.0271(3) 0.8425(5) -0.03666(17) 0.0385(12) Uani 1 1 d . . . . .
C10 C -0.0780(4) 0.7855(6) -0.0071(2) 0.0579(16) Uani 1 1 d . . . . .
H10 H -0.1376 0.8117 -0.0111 0.070 Uiso 1 1 calc R U . . .
C11 C -0.0410(4) 0.6903(6) 0.0279(2) 0.0578(16) Uani 1 1 d . . . . .
H11 H -0.0770 0.6538 0.0469 0.069 Uiso 1 1 calc R U . . .
C12Q C 0.0469(3) 0.6473(5) 0.03592(18) 0.0393(12) Uani 1 1 d . . . . .
C13 C 0.0966(4) 0.7041(6) 0.0060(2) 0.0586(16) Uani 1 1 d . . . . .
H13 H 0.1563 0.6779 0.0099 0.070 Uiso 1 1 calc R U . . .
C14E C 0.0858(3) 0.5458(5) 0.07399(17) 0.0376(12) Uani 1 1 d . . . . .
C15U C 0.0368(4) 0.4892(6) 0.10442(19) 0.0479(13) Uani 1 1 d . . . . .
H15U H -0.0230 0.5144 0.1005 0.058 Uiso 1 1 calc R U . . .
C16Y C 0.0740(4) 0.3972(6) 0.14006(19) 0.0491(14) Uani 1 1 d . . . . .
C17H C 0.0179(4) 0.3399(8) 0.1719(2) 0.0673(19) Uani 1 1 d . . . . .
C18F C 0.1631(4) 0.3583(6) 0.14751(18) 0.0467(13) Uani 1 1 d . . . . .
H18F H 0.1887 0.2967 0.1719 0.056 Uiso 1 1 calc R U . . .
C19 C 0.2130(4) 0.4139(6) 0.1177(2) 0.0506(14) Uani 1 1 d . . . . .
C20 C 0.1754(4) 0.5042(6) 0.0819(2) 0.0496(14) Uani 1 1 d . . . . .
H20 H 0.2105 0.5392 0.0622 0.060 Uiso 1 1 calc R U . . .
C21Q C 0.3081(5) 0.3746(9) 0.1245(3) 0.084(2) Uani 1 1 d . . . . .
C45 C 0.0603(4) 0.7980(7) -0.0291(2) 0.0616(17) Uani 1 1 d . . . . .
H45 H 0.0960 0.8328 -0.0485 0.074 Uiso 1 1 calc R U . . .
N1 N -0.2626(4) 0.9955(7) -0.0442(3) 0.097(2) 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'
Br Br -0.2901 2.4595 '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'
H H 0.0000 0.0000 '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
_geom_angle_publ_flag
N1 C1 C7T 176.9(7) . . ?
C2N C1I C6X 120.2(6) . . ?
C2N C1I H1I 119.9 . . ?
C6X C1I H1I 119.9 . . ?
C3B C2N C1I 119.6(6) . . ?
C3B C2N Br1 120.6(5) . . ?
C1I C2N Br1 119.8(5) . . ?
C2N C3B C4O 120.1(6) . . ?
C2N C3B H3B 119.9 . . ?
C4O C3B H3B 119.9 . . ?
C5 C4O C3B 121.9(6) . . ?
C5 C4O H4O 119.0 . . ?
C3B C4O H4O 119.0 . . ?
C4O C5 C6X 116.9(5) . . ?
C4O C5 C7T 121.3(5) . . ?
C6X C5 C7T 121.8(5) . . ?
C5 C6X C1I 121.2(6) . . ?
C5 C6X H6X 119.4 . . ?
C1I C6X H6X 119.4 . . ?
C8K C7T C1 120.7(5) . . ?
C8K C7T C5 124.3(5) . . ?
C1 C7T C5 115.0(5) . . ?
C7T C8K C9D 132.9(5) . . ?
C7T C8K H8K 113.6 . . ?
C9D C8K H8K 113.6 . . ?
C45 C9D C10 116.4(5) . . ?
C45 C9D C8K 117.6(5) . . ?
C10 C9D C8K 126.0(5) . . ?
C11 C10 C9D 120.9(5) . . ?
C11 C10 H10 119.6 . . ?
C9D C10 H10 119.6 . . ?
C12Q C11 C10 122.6(5) . . ?
C12Q C11 H11 118.7 . . ?
C10 C11 H11 118.7 . . ?
C11 C12Q C13 115.9(5) . . ?
C11 C12Q C14E 122.0(5) . . ?
C13 C12Q C14E 122.1(5) . . ?
C45 C13 C12Q 121.8(5) . . ?
C45 C13 H13 119.1 . . ?
C12Q C13 H13 119.1 . . ?
C15U C14E C20 116.1(5) . . ?
C15U C14E C12Q 122.5(5) . . ?
C20 C14E C12Q 121.3(5) . . ?
C16Y C15U C14E 122.0(5) . . ?
C16Y C15U H15U 119.0 . . ?
C14E C15U H15U 119.0 . . ?
C15U C16Y C18F 120.8(5) . . ?
C15U C16Y C17H 119.6(5) . . ?
C18F C16Y C17H 119.6(5) . . ?
F8 C17H F7 105.8(7) . . ?
F8 C17H F9 108.1(7) . . ?
F7 C17H F9 103.0(6) . . ?
F8 C17H C16Y 114.1(5) . . ?
F7 C17H C16Y 113.3(6) . . ?
F9 C17H C16Y 111.8(6) . . ?
C19 C18F C16Y 118.0(5) . . ?
C19 C18F H18F 121.0 . . ?
C16Y C18F H18F 121.0 . . ?
C20 C19 C18F 120.9(5) . . ?
C20 C19 C21Q 119.6(6) . . ?
C18F C19 C21Q 119.5(5) . . ?
C19 C20 C14E 122.1(5) . . ?
C19 C20 H20 118.9 . . ?
C14E C20 H20 118.9 . . ?
F10 C21Q F12 108.4(9) . . ?
F10 C21Q F11 103.3(10) . . ?
F12 C21Q F11 95.0(8) . . ?
F10 C21Q C19 117.7(6) . . ?
F12 C21Q C19 116.8(8) . . ?
F11 C21Q C19 112.5(8) . . ?
C13 C45 C9D 122.4(5) . . ?
C13 C45 H45 118.8 . . ?
C9D C45 H45 118.8 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C2N 1.892(6) . ?
F7 C17H 1.299(8) . ?
F8 C17H 1.295(7) . ?
F9 C17H 1.320(8) . ?
F10 C21Q 1.201(8) . ?
F11 C21Q 1.276(10) . ?
F12 C21Q 1.250(9) . ?
C1 N1 1.151(8) . ?
C1 C7T 1.440(8) . ?
C1I C2N 1.365(9) . ?
C1I C6X 1.384(8) . ?
C1I H1I 0.9300 . ?
C2N C3B 1.347(9) . ?
C3B C4O 1.383(8) . ?
C3B H3B 0.9300 . ?
C4O C5 1.371(7) . ?
C4O H4O 0.9300 . ?
C5 C6X 1.377(8) . ?
C5 C7T 1.485(7) . ?
C6X H6X 0.9300 . ?
C7T C8K 1.333(7) . ?
C8K C9D 1.463(7) . ?
C8K H8K 0.9300 . ?
C9D C45 1.376(7) . ?
C9D C10 1.392(7) . ?
C10 C11 1.382(8) . ?
C10 H10 0.9300 . ?
C11 C12Q 1.379(7) . ?
C11 H11 0.9300 . ?
C12Q C13 1.387(7) . ?
C12Q C14E 1.483(7) . ?
C13 C45 1.372(8) . ?
C13 H13 0.9300 . ?
C14E C15U 1.389(7) . ?
C14E C20 1.397(7) . ?
C15U C16Y 1.372(7) . ?
C15U H15U 0.9300 . ?
C16Y C18F 1.385(8) . ?
C16Y C17H 1.499(8) . ?
C18F C19 1.382(7) . ?
C18F H18F 0.9300 . ?
C19 C20 1.364(7) . ?
C19 C21Q 1.475(9) . ?
C20 H20 0.9300 . ?
C45 H45 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
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6X C1I C2N C3B -1.1(10) . . . . ?
C6X C1I C2N Br1 177.7(5) . . . . ?
C1I C2N C3B C4O 0.4(9) . . . . ?
Br1 C2N C3B C4O -178.4(5) . . . . ?
C2N C3B C4O C5 -0.1(9) . . . . ?
C3B C4O C5 C6X 0.5(9) . . . . ?
C3B C4O C5 C7T 179.7(5) . . . . ?
C4O C5 C6X C1I -1.2(9) . . . . ?
C7T C5 C6X C1I 179.6(6) . . . . ?
C2N C1I C6X C5 1.5(11) . . . . ?
C4O C5 C7T C8K 173.6(5) . . . . ?
C6X C5 C7T C8K -7.2(8) . . . . ?
C4O C5 C7T C1 -7.7(7) . . . . ?
C6X C5 C7T C1 171.5(6) . . . . ?
C1 C7T C8K C9D 2.0(9) . . . . ?
C5 C7T C8K C9D -179.3(5) . . . . ?
C7T C8K C9D C45 -173.9(6) . . . . ?
C7T C8K C9D C10 7.3(9) . . . . ?
C45 C9D C10 C11 0.5(9) . . . . ?
C8K C9D C10 C11 179.4(6) . . . . ?
C9D C10 C11 C12Q 0.4(10) . . . . ?
C10 C11 C12Q C13 -0.8(9) . . . . ?
C10 C11 C12Q C14E 179.5(6) . . . . ?
C11 C12Q C13 C45 0.4(9) . . . . ?
C14E C12Q C13 C45 -180.0(6) . . . . ?
C11 C12Q C14E C15U -1.0(8) . . . . ?
C13 C12Q C14E C15U 179.4(5) . . . . ?
C11 C12Q C14E C20 -179.4(5) . . . . ?
C13 C12Q C14E C20 0.9(8) . . . . ?
C20 C14E C15U C16Y -0.3(8) . . . . ?
C12Q C14E C15U C16Y -178.8(5) . . . . ?
C14E C15U C16Y C18F 0.9(9) . . . . ?
C14E C15U C16Y C17H 179.8(6) . . . . ?
C15U C16Y C17H F8 -167.2(7) . . . . ?
C18F C16Y C17H F8 11.7(10) . . . . ?
C15U C16Y C17H F7 -46.0(9) . . . . ?
C18F C16Y C17H F7 132.9(6) . . . . ?
C15U C16Y C17H F9 69.8(8) . . . . ?
C18F C16Y C17H F9 -111.3(6) . . . . ?
C15U C16Y C18F C19 -0.7(8) . . . . ?
C17H C16Y C18F C19 -179.6(6) . . . . ?
C16Y C18F C19 C20 0.0(8) . . . . ?
C16Y C18F C19 C21Q -179.8(6) . . . . ?
C18F C19 C20 C14E 0.6(9) . . . . ?
C21Q C19 C20 C14E -179.6(6) . . . . ?
C15U C14E C20 C19 -0.4(8) . . . . ?
C12Q C14E C20 C19 178.1(5) . . . . ?
C20 C19 C21Q F10 -2.9(14) . . . . ?
C18F C19 C21Q F10 176.9(10) . . . . ?
C20 C19 C21Q F12 -134.6(9) . . . . ?
C18F C19 C21Q F12 45.2(12) . . . . ?
C20 C19 C21Q F11 117.0(9) . . . . ?
C18F C19 C21Q F11 -63.2(11) . . . . ?
C12Q C13 C45 C9D 0.6(10) . . . . ?
C10 C9D C45 C13 -1.0(9) . . . . ?
C8K C9D C45 C13 -179.9(6) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168306153
