#------------------------------------------------------------------------------
#$Date: 2022-09-23 01:56:11 +0300 (Fri, 23 Sep 2022) $
#$Revision: 278092 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/13/7711314.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_7711314
loop_
_publ_author_name
'P, Chinna Ayya Swamy'
'Raveendran, Archana V.'
'Sivakrishna, Narra'
'Nandi, Rajendra Prasad'
_publ_section_title
;
 Triarylborane-triphenylamine based luminophore for the mitochondria
 targeted live cell imaging and colorimetric detection of aqueous fluoride
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D2DT01887J
_journal_year                    2022
_chemical_formula_moiety         'C36 H34 B1 N1 Br2'
_chemical_formula_sum            'C18 H17 B0.5 Br N0.5'
_chemical_formula_weight         325.64
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-01-02 deposited with the CCDC.	2022-09-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.682(6)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.682(5)
_cell_length_b                   14.346(3)
_cell_length_c                   12.215(3)
_cell_measurement_reflns_used    6151
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      22.54
_cell_measurement_theta_min      3.32
_cell_volume                     3336.4(14)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'WinGX v2014.1'
_computing_publication_material  'WinGX v2014.1'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_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  0.1495
_diffrn_reflns_av_unetI/netI     0.1018
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            49667
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.559
_diffrn_reflns_theta_min         3.323
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    2.453
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_description       block
_exptl_crystal_F_000             1328
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Diethylether'
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.410
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         3839
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.994
_refine_ls_R_factor_all          0.1952
_refine_ls_R_factor_gt           0.0546
_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)+(0.0390P)²+5.5501P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0977
_refine_ls_wR_factor_ref         0.1323
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1568
_reflns_number_total             3839
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2dt01887j2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_atom_sites_solution_secondary' value 'diffmap' was
changed to 'difmap'.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_cell_volume        3336.2(13)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_original_formula_sum        'C18 H17 B0.50 Br N0.50'
_cod_database_code               7711314
_shelx_shelxl_version_number     2018/3
_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.
;
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 0.26510(3) 0.47172(4) 0.43100(5) 0.1120(3) Uani 1 1 d . . . . .
C1 C 0.7725(2) 1.2842(4) 0.7941(5) 0.115(2) Uani 1 1 d . . . . .
H1A H 0.770553 1.322312 0.728765 0.173 Uiso 1 1 calc R U . . .
H1B H 0.808957 1.238462 0.800936 0.173 Uiso 1 1 calc R U . . .
H1C H 0.782373 1.322671 0.860605 0.173 Uiso 1 1 calc R U . . .
C2 C 0.7022(2) 1.2353(3) 0.7815(5) 0.0705(13) Uani 1 1 d . . . . .
C3 C 0.6624(2) 1.2508(3) 0.8566(4) 0.0689(12) Uani 1 1 d . . . . .
H3 H 0.679212 1.291610 0.916507 0.083 Uiso 1 1 calc R U . . .
C4 C 0.5981(2) 1.2082(3) 0.8473(3) 0.0574(11) Uani 1 1 d . . . . .
C5 C 0.57163(18) 1.1441(2) 0.7594(3) 0.0466(9) Uani 1 1 d . . . . .
C10 C 0.500000 0.9834(4) 0.750000 0.0420(12) Uani 1 2 d S T P . .
C11 C 0.43807(18) 0.9309(3) 0.7159(3) 0.0478(10) Uani 1 1 d . . . . .
H11 H 0.395474 0.962199 0.692577 0.057 Uiso 1 1 calc R U . . .
C12 C 0.43776(18) 0.8351(3) 0.7155(3) 0.0522(10) Uani 1 1 d . . . . .
H12 H 0.395386 0.803274 0.691806 0.063 Uiso 1 1 calc R U . . .
C13 C 0.500000 0.7852(3) 0.750000 0.0480(14) Uani 1 2 d S T P . .
N1 N 0.500000 0.6877(3) 0.750000 0.0604(13) Uani 1 2 d S T P . .
C14 C 0.44510(19) 0.6373(3) 0.6755(3) 0.0566(11) Uani 1 1 d . . . . .
C19 C 0.4245(2) 0.6582(3) 0.5618(4) 0.0687(12) Uani 1 1 d . . . . .
H19 H 0.447012 0.705868 0.533116 0.082 Uiso 1 1 calc R U . . .
C18 C 0.3711(2) 0.6098(3) 0.4902(4) 0.0755(13) Uani 1 1 d . . . . .
H18 H 0.357341 0.625322 0.413836 0.091 Uiso 1 1 calc R U . . .
C17 C 0.3381(2) 0.5390(3) 0.5308(4) 0.0706(13) Uani 1 1 d . . . . .
C16 C 0.3575(3) 0.5171(3) 0.6436(4) 0.0917(16) Uani 1 1 d . . . . .
H16 H 0.334849 0.469280 0.671682 0.110 Uiso 1 1 calc R U . . .
C15 C 0.4110(3) 0.5665(3) 0.7155(4) 0.0849(15) Uani 1 1 d . . . . .
H15 H 0.424020 0.551650 0.792099 0.102 Uiso 1 1 calc R U . . .
C8 C 0.5579(2) 1.2312(4) 0.9348(4) 0.0973(17) Uani 1 1 d . . . . .
H8A H 0.550607 1.175234 0.973364 0.146 Uiso 1 1 calc R U . . .
H8B H 0.513301 1.258000 0.897781 0.146 Uiso 1 1 calc R U . . .
H8C H 0.584372 1.274896 0.988502 0.146 Uiso 1 1 calc R U . . .
C7 C 0.6763(2) 1.1741(3) 0.6947(4) 0.0707(13) Uani 1 1 d . . . . .
H7 H 0.702334 1.163155 0.642189 0.085 Uiso 1 1 calc R U . . .
C6 C 0.6131(2) 1.1279(3) 0.6821(3) 0.0553(10) Uani 1 1 d . . . . .
C9 C 0.5896(2) 1.0631(3) 0.5816(4) 0.0832(14) Uani 1 1 d . . . . .
H9A H 0.612612 1.080158 0.524022 0.125 Uiso 1 1 calc R U . . .
H9B H 0.539659 1.067954 0.551986 0.125 Uiso 1 1 calc R U . . .
H9C H 0.601658 1.000073 0.605186 0.125 Uiso 1 1 calc R U . . .
B1 B 0.500000 1.0909(4) 0.750000 0.0430(15) Uani 1 2 d S T P . .
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'
B B 0.0013 0.0007 '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'
N N 0.0061 0.0033 '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
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C7 117.3(4) . . ?
C3 C2 C1 121.2(5) . . ?
C7 C2 C1 121.5(5) . . ?
C2 C3 C4 122.7(4) . . ?
C2 C3 H3 118.6 . . ?
C4 C3 H3 118.6 . . ?
C3 C4 C5 120.4(4) . . ?
C3 C4 C8 118.4(4) . . ?
C5 C4 C8 121.3(4) . . ?
C4 C5 C6 116.8(4) . . ?
C4 C5 B1 121.4(3) . . ?
C6 C5 B1 121.7(3) . . ?
C11 C10 C11 115.1(5) 2_656 . ?
C11 C10 B1 122.5(2) 2_656 . ?
C11 C10 B1 122.5(2) . . ?
C12 C11 C10 122.7(4) . . ?
C12 C11 H11 118.6 . . ?
C10 C11 H11 118.6 . . ?
C11 C12 C13 120.7(4) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C12 C13 C12 118.0(5) 2_656 . ?
C12 C13 N1 121.0(2) 2_656 . ?
C12 C13 N1 121.0(2) . . ?
C13 N1 C14 120.6(2) . 2_656 ?
C13 N1 C14 120.6(2) . . ?
C14 N1 C14 118.8(4) 2_656 . ?
C15 C14 C19 118.3(4) . . ?
C15 C14 N1 120.6(4) . . ?
C19 C14 N1 121.1(4) . . ?
C18 C19 C14 120.9(4) . . ?
C18 C19 H19 119.5 . . ?
C14 C19 H19 119.5 . . ?
C17 C18 C19 120.2(4) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C18 C17 C16 120.0(4) . . ?
C18 C17 Br1 119.9(3) . . ?
C16 C17 Br1 120.1(4) . . ?
C17 C16 C15 119.6(4) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C14 C15 C16 121.0(4) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C2 C7 C6 122.7(4) . . ?
C2 C7 H7 118.6 . . ?
C6 C7 H7 118.6 . . ?
C7 C6 C5 120.1(4) . . ?
C7 C6 C9 117.7(4) . . ?
C5 C6 C9 122.2(4) . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C10 B1 C5 118.9(2) . . ?
C10 B1 C5 118.9(2) . 2_656 ?
C5 B1 C5 122.2(5) . 2_656 ?
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 C17 1.896(4) . ?
C1 C2 1.524(6) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.368(6) . ?
C2 C7 1.372(6) . ?
C3 C4 1.382(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.409(5) . ?
C4 C8 1.519(6) . ?
C5 C6 1.414(5) . ?
C5 B1 1.582(5) . ?
C10 C11 1.403(4) 2_656 ?
C10 C11 1.403(4) . ?
C10 B1 1.542(8) . ?
C11 C12 1.374(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.388(4) . ?
C12 H12 0.9300 . ?
C13 N1 1.399(6) . ?
N1 C14 1.421(4) 2_656 ?
N1 C14 1.421(4) . ?
C14 C15 1.373(6) . ?
C14 C19 1.378(5) . ?
C19 C18 1.373(5) . ?
C19 H19 0.9300 . ?
C18 C17 1.364(6) . ?
C18 H18 0.9300 . ?
C17 C16 1.370(6) . ?
C16 C15 1.383(6) . ?
C16 H16 0.9300 . ?
C15 H15 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C7 C6 1.384(6) . ?
C7 H7 0.9300 . ?
C6 C9 1.515(5) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
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
C7 C2 C3 C4 -0.6(6) . . . . ?
C1 C2 C3 C4 179.5(4) . . . . ?
C2 C3 C4 C5 1.6(6) . . . . ?
C2 C3 C4 C8 -179.3(4) . . . . ?
C3 C4 C5 C6 -1.2(5) . . . . ?
C8 C4 C5 C6 179.8(4) . . . . ?
C3 C4 C5 B1 177.1(4) . . . . ?
C8 C4 C5 B1 -2.0(6) . . . . ?
C11 C10 C11 C12 -0.1(3) 2_656 . . . ?
B1 C10 C11 C12 179.9(3) . . . . ?
C10 C11 C12 C13 0.3(5) . . . . ?
C11 C12 C13 C12 -0.1(3) . . . 2_656 ?
C11 C12 C13 N1 179.9(3) . . . . ?
C12 C13 N1 C14 26.0(3) 2_656 . . 2_656 ?
C12 C13 N1 C14 -154.0(3) . . . 2_656 ?
C12 C13 N1 C14 -154.0(3) 2_656 . . . ?
C12 C13 N1 C14 26.0(3) . . . . ?
C13 N1 C14 C15 -130.4(3) . . . . ?
C14 N1 C14 C15 49.6(3) 2_656 . . . ?
C13 N1 C14 C19 49.3(4) . . . . ?
C14 N1 C14 C19 -130.7(4) 2_656 . . . ?
C15 C14 C19 C18 0.1(7) . . . . ?
N1 C14 C19 C18 -179.5(4) . . . . ?
C14 C19 C18 C17 -0.8(7) . . . . ?
C19 C18 C17 C16 1.1(7) . . . . ?
C19 C18 C17 Br1 -179.4(3) . . . . ?
C18 C17 C16 C15 -0.6(8) . . . . ?
Br1 C17 C16 C15 179.8(4) . . . . ?
C19 C14 C15 C16 0.4(7) . . . . ?
N1 C14 C15 C16 -180.0(4) . . . . ?
C17 C16 C15 C14 -0.1(8) . . . . ?
C3 C2 C7 C6 -0.7(6) . . . . ?
C1 C2 C7 C6 179.2(4) . . . . ?
C2 C7 C6 C5 1.1(6) . . . . ?
C2 C7 C6 C9 179.1(4) . . . . ?
C4 C5 C6 C7 -0.1(5) . . . . ?
B1 C5 C6 C7 -178.4(3) . . . . ?
C4 C5 C6 C9 -178.0(4) . . . . ?
B1 C5 C6 C9 3.7(5) . . . . ?
C11 C10 B1 C5 15.3(2) 2_656 . . . ?
C11 C10 B1 C5 -164.7(2) . . . . ?
C11 C10 B1 C5 -164.7(2) 2_656 . . 2_656 ?
C11 C10 B1 C5 15.3(2) . . . 2_656 ?
C4 C5 B1 C10 -122.4(3) . . . . ?
C6 C5 B1 C10 55.8(3) . . . . ?
C4 C5 B1 C5 57.6(3) . . . 2_656 ?
C6 C5 B1 C5 -124.2(3) . . . 2_656 ?
