#------------------------------------------------------------------------------
#$Date: 2025-04-05 04:32:29 +0200 (Sat 05 de Apr de 2025) $
#$Revision: 298831 $
#$URL: svn://www.crystallography.net/cod/cif/1/57/40/1574025.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_1574025
loop_
_publ_author_name
'Parui, Retwik'
'Roy, Hirakjyoti'
'Meher, Niranjan'
'Ghosh, Siddhartha Sankar'
'Iyer, Parameswar Krishnan'
_publ_section_title
;
 Mechanistic investigation on cellular internalization triggering
 structure-induced conformational modulation of boron-nitrogen luminogens.
;
_journal_issue                   14
_journal_name_full               'Chemical science'
_journal_page_first              6023
_journal_page_last               6034
_journal_paper_doi               10.1039/d4sc08296f
_journal_volume                  16
_journal_year                    2025
_chemical_formula_sum            'C16 H12 B Cl N2'
_chemical_formula_weight         278.54
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2024-02-28 deposited with the CCDC.	2025-02-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.628(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.7299(7)
_cell_length_b                   10.3015(15)
_cell_length_c                   13.5889(19)
_cell_measurement_reflns_used    9368
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      24.99
_cell_measurement_theta_min      4.23
_cell_volume                     657.69(16)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      300(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_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  0.0415
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12533
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         1.509
_exptl_absorpt_coefficient_mu    0.278
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
;
 Flack x determined using 1003 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         2295
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0306
_refine_ls_R_factor_gt           0.0289
_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)+(0.0428P)²+0.1018P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0760
_refine_ls_wR_factor_ref         0.0824
_reflns_Friedel_coverage         0.883
_reflns_Friedel_fraction_full    0.984
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                2211
_reflns_number_total             2295
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc08296f2.cif
_cod_data_source_block           NBCl_0m_a
_cod_depositor_comments
'Adding full bibliography for 1574024--1574028.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1574025
_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+1/2, -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_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
Cl01 Cl 1.03651(15) 0.87738(10) 0.07528(5) 0.0564(2) Uani 1 1 d . . . . .
N002 N 0.1817(5) 0.5031(2) 0.34989(16) 0.0401(5) Uani 1 1 d . . . . .
H1 H 0.252(7) 0.558(4) 0.390(2) 0.060 Uiso 1 1 d . U . . .
N003 N 0.1196(5) 0.3892(3) 0.19594(15) 0.0414(5) Uani 1 1 d . . . . .
H1A H 0.145(7) 0.377(4) 0.142(2) 0.062 Uiso 1 1 d . U . . .
C005 C 0.4630(6) 0.5879(3) 0.20810(19) 0.0370(6) Uani 1 1 d . . . . .
C006 C -0.3367(6) 0.2363(3) 0.3676(2) 0.0407(6) Uani 1 1 d . . . . .
C007 C -0.0741(5) 0.3041(2) 0.23079(19) 0.0382(6) Uani 1 1 d . . . . .
C008 C -0.2011(6) 0.2060(3) 0.1729(2) 0.0484(7) Uani 1 1 d . . . . .
H008 H -0.158757 0.195159 0.108310 0.058 Uiso 1 1 calc R U . . .
C009 C -0.0112(5) 0.4224(2) 0.39016(19) 0.0378(6) Uani 1 1 d . . . . .
B0 B 0.2537(6) 0.4917(3) 0.2522(2) 0.0369(6) Uani 1 1 d . . . . .
C00A C 0.7797(6) 0.7747(3) 0.2251(2) 0.0471(7) Uani 1 1 d . . . . .
H00A H 0.869657 0.839728 0.264534 0.056 Uiso 1 1 calc R U . . .
C00B C -0.4025(6) 0.2567(3) 0.4655(2) 0.0471(7) Uani 1 1 d . . . . .
H00B H -0.532552 0.202656 0.491654 0.057 Uiso 1 1 calc R U . . .
C00C C -0.0799(6) 0.4377(3) 0.4853(2) 0.0475(7) Uani 1 1 d . . . . .
H00C H 0.004771 0.503411 0.525345 0.057 Uiso 1 1 calc R U . . .
C00D C -0.4621(6) 0.1369(3) 0.3059(2) 0.0495(7) Uani 1 1 d . . . . .
H00D H -0.592164 0.080698 0.329772 0.059 Uiso 1 1 calc R U . . .
C00E C 0.6899(7) 0.6686(3) 0.0684(2) 0.0505(7) Uani 1 1 d . . . . .
H00E H 0.720246 0.661835 0.002177 0.061 Uiso 1 1 calc R U . . .
C00F C -0.2765(6) 0.3546(3) 0.5214(2) 0.0516(8) Uani 1 1 d . . . . .
H00F H -0.322735 0.366579 0.585426 0.062 Uiso 1 1 calc R U . . .
C00G C 0.8191(5) 0.7648(3) 0.1267(2) 0.0404(6) Uani 1 1 d . . . . .
C00H C 0.5138(7) 0.5814(3) 0.1090(2) 0.0491(7) Uani 1 1 d . . . . .
H00H H 0.426157 0.516366 0.068934 0.059 Uiso 1 1 calc R U . . .
C00I C 0.6042(6) 0.6864(3) 0.2641(2) 0.0458(7) Uani 1 1 d . . . . .
H00I H 0.579074 0.692884 0.330822 0.055 Uiso 1 1 calc R U . . .
C00J C -0.3948(7) 0.1224(3) 0.2116(2) 0.0521(7) Uani 1 1 d . . . . .
H00J H -0.478706 0.055802 0.172224 0.063 Uiso 1 1 calc R U . . .
C4 C -0.1388(5) 0.3213(2) 0.32947(18) 0.0364(5) 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'
B B 0.0013 0.0007 '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'
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
C009 N002 B0 124.0(2) . . ?
C007 N003 B0 124.1(2) . . ?
C00I C005 C00H 115.9(2) . . ?
C00I C005 B0 122.4(2) . . ?
C00H C005 B0 121.7(2) . . ?
C00D C006 C00B 122.9(3) . . ?
C00D C006 C4 118.7(2) . . ?
C00B C006 C4 118.4(3) . . ?
C008 C007 N003 122.0(2) . . ?
C008 C007 C4 120.2(2) . . ?
N003 C007 C4 117.7(2) . . ?
C007 C008 C00J 119.9(3) . . ?
C00C C009 N002 122.5(2) . . ?
C00C C009 C4 119.9(2) . . ?
N002 C009 C4 117.6(2) . . ?
N003 B0 N002 115.4(2) . . ?
N003 B0 C005 122.0(2) . . ?
N002 B0 C005 122.5(2) . . ?
C00G C00A C00I 118.8(3) . . ?
C00F C00B C006 120.3(3) . . ?
C009 C00C C00F 119.9(3) . . ?
C00J C00D C006 120.7(3) . . ?
C00G C00E C00H 119.3(3) . . ?
C00B C00F C00C 121.8(2) . . ?
C00E C00G C00A 121.0(3) . . ?
C00E C00G Cl01 119.6(2) . . ?
C00A C00G Cl01 119.5(2) . . ?
C00E C00H C005 122.2(3) . . ?
C00A C00I C005 122.9(3) . . ?
C00D C00J C008 121.2(3) . . ?
C009 C4 C007 121.1(2) . . ?
C009 C4 C006 119.6(2) . . ?
C007 C4 C006 119.3(2) . . ?
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
Cl01 C00G 1.748(3) . ?
N002 C009 1.392(3) . ?
N002 B0 1.413(4) . ?
N003 C007 1.390(4) . ?
N003 B0 1.411(4) . ?
C005 C00I 1.392(4) . ?
C005 C00H 1.397(4) . ?
C005 B0 1.567(4) . ?
C006 C00D 1.410(4) . ?
C006 C00B 1.417(4) . ?
C006 C4 1.422(4) . ?
C007 C008 1.375(4) . ?
C007 C4 1.420(4) . ?
C008 C00J 1.403(4) . ?
C009 C00C 1.377(4) . ?
C009 C4 1.420(4) . ?
C00A C00G 1.375(4) . ?
C00A C00I 1.378(4) . ?
C00B C00F 1.358(4) . ?
C00C C00F 1.394(4) . ?
C00D C00J 1.364(4) . ?
C00E C00G 1.368(4) . ?
C00E C00H 1.382(4) . ?
