#------------------------------------------------------------------------------
#$Date: 2024-01-06 11:55:43 +0200 (Sat, 06 Jan 2024) $
#$Revision: 288908 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/76/7247675.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_7247675
loop_
_publ_author_name
'Bhattacharyya, Arghyadeep'
'Das, Akash'
'Guchhait, Nikhil'
_publ_section_title
;
 Interrogating the nature of aggregates formed in a model azine based
 ESIPT coupled AIE active probe: stark differences in photodynamics in the
 solid state and aggregates in water.
;
_journal_issue                   46
_journal_name_full               'Physical chemistry chemical physics : PCCP'
_journal_page_first              31702
_journal_page_last               31713
_journal_paper_doi               10.1039/d3cp03603k
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         C19H15BrN2O
_chemical_formula_sum            'C19 H15 Br N2 O'
_chemical_formula_weight         367.2443
_chemical_melting_point          503
_chemical_name_common            BNHMP
_chemical_name_systematic
4-bromo-2-((E)-((Z)-(1-(naphthalen-2-yl)ethylidene)hydrazono)methyl)phenol
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2023-08-28 deposited with the CCDC.	2023-10-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.681(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.2672(6)
_cell_length_b                   14.7584(12)
_cell_length_c                   17.2093(13)
_cell_measurement_reflns_used    2884
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.13
_cell_measurement_theta_min      3.58
_cell_volume                     1586.4(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-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_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  0.0471
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13985
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        20.456
_diffrn_reflns_theta_max         20.456
_diffrn_reflns_theta_min         2.747
_exptl_absorpt_coefficient_mu    2.597
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_description       rhombic
_exptl_crystal_F_000             1140
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   2.013
_exptl_transmission_factor_min   1.257
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.0004(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         1556
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0278
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0390P)²+0.8088P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0727
_refine_ls_wR_factor_ref         0.0758
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1339
_reflns_number_total             1556
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cp03603k2.cif
_cod_data_source_block           BNHMP
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'EMPIRICAL' was
changed to 'empirical' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7247675.cif.
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7247675
_shelx_shelxl_version_number     2016/6
_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   0.746
_shelx_estimated_absorpt_t_max   0.572
loop_
_space_group_symop_operation_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_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 0.84318(7) 0.40143(3) 0.94112(2) 0.0823(3) Uani 1 1 d . . . . .
O1 O 0.1821(4) 0.45992(18) 0.67364(15) 0.0653(7) Uani 1 1 d . . . . .
H1 H 0.230226 0.449293 0.631688 0.098 Uiso 1 1 calc R U . . .
N2 N 0.5275(4) 0.37235(17) 0.50989(17) 0.0499(7) Uani 1 1 d . . . . .
N1 N 0.4554(5) 0.39898(18) 0.58141(17) 0.0501(7) Uani 1 1 d . . . . .
C6 C 0.5386(5) 0.4107(2) 0.7182(2) 0.0426(8) Uani 1 1 d . . . . .
C8 C 0.3846(5) 0.3805(2) 0.4527(2) 0.0455(9) Uani 1 1 d . . . . .
C10 C 0.4441(5) 0.3526(2) 0.37506(19) 0.0441(8) Uani 1 1 d . . . . .
C17 C 0.3692(5) 0.3403(2) 0.23395(19) 0.0447(8) Uani 1 1 d . . . . .
C18 C 0.5720(5) 0.3012(2) 0.2274(2) 0.0465(9) Uani 1 1 d . . . . .
C5 C 0.6865(5) 0.3968(2) 0.7819(2) 0.0476(9) Uani 1 1 d . . . . .
H4 H 0.820954 0.373416 0.774127 0.057 Uiso 1 1 calc R U . . .
C1 C 0.3350(5) 0.4452(2) 0.7318(2) 0.0485(9) Uani 1 1 d . . . . .
C7 C 0.5923(6) 0.3891(2) 0.6399(2) 0.0473(9) Uani 1 1 d . . . . .
H5 H 0.728628 0.367840 0.632185 0.057 Uiso 1 1 calc R U . . .
C00D C 0.3115(5) 0.3654(2) 0.3083(2) 0.0468(9) Uani 1 1 d . . . . .
H7 H 0.178086 0.391754 0.312473 0.056 Uiso 1 1 calc R U . . .
C11 C 0.6455(5) 0.3112(2) 0.3671(2) 0.0529(9) Uani 1 1 d . . . . .
H13 H 0.737467 0.300368 0.411301 0.063 Uiso 1 1 calc R U . . .
C2 C 0.2894(6) 0.4645(2) 0.8072(2) 0.0555(10) Uani 1 1 d . . . . .
H2 H 0.155370 0.487327 0.816255 0.067 Uiso 1 1 calc R U . . .
C12 C 0.7057(5) 0.2872(2) 0.2964(2) 0.0558(10) Uani 1 1 d . . . . .
H12 H 0.839292 0.260699 0.293007 0.067 Uiso 1 1 calc R U . . .
C16 C 0.2279(6) 0.3537(2) 0.1640(2) 0.0563(10) Uani 1 1 d . . . . .
H8 H 0.092589 0.378500 0.167318 0.068 Uiso 1 1 calc R U . . .
C3 C 0.4379(6) 0.4505(2) 0.8686(2) 0.0575(10) Uani 1 1 d . . . . .
H3 H 0.404683 0.463741 0.919060 0.069 Uiso 1 1 calc R U . . .
C4 C 0.6368(5) 0.4169(2) 0.8557(2) 0.0510(9) Uani 1 1 d . . . . .
C13 C 0.6306(6) 0.2787(2) 0.1524(2) 0.0626(10) Uani 1 1 d . . . . .
H11 H 0.764473 0.253411 0.146898 0.075 Uiso 1 1 calc R U . . .
C14 C 0.4950(7) 0.2932(3) 0.0882(2) 0.0680(11) Uani 1 1 d . . . . .
H10 H 0.536635 0.278522 0.039155 0.082 Uiso 1 1 calc R U . . .
C15 C 0.2916(7) 0.3305(3) 0.0957(2) 0.0702(11) Uani 1 1 d . . . . .
H9 H 0.199268 0.339133 0.051210 0.084 Uiso 1 1 calc R U . . .
C9 C 0.1669(6) 0.4191(3) 0.4617(2) 0.0690(11) Uani 1 1 d . . . . .
H6B H 0.097093 0.384167 0.499229 0.103 Uiso 1 1 calc R U . . .
H6A H 0.083336 0.417166 0.412377 0.103 Uiso 1 1 calc R U . . .
H6C H 0.180664 0.480792 0.479090 0.103 Uiso 1 1 calc R U . . .
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'
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'
O O 0.0106 0.0060 '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
C1 O1 H1 109.5 . . ?
C8 N2 N1 113.1(3) . . ?
C7 N1 N2 114.6(3) . . ?
C5 C6 C1 118.4(3) . . ?
C5 C6 C7 120.6(3) . . ?
C1 C6 C7 121.0(3) . . ?
N2 C8 C10 117.2(3) . . ?
N2 C8 C9 122.9(3) . . ?
C10 C8 C9 119.9(3) . . ?
C00D C10 C11 117.4(3) . . ?
C00D C10 C8 122.6(3) . . ?
C11 C10 C8 120.0(3) . . ?
C00D C17 C18 118.8(3) . . ?
C00D C17 C16 122.3(3) . . ?
C18 C17 C16 118.9(3) . . ?
C17 C18 C13 118.3(3) . . ?
C17 C18 C12 118.0(3) . . ?
C13 C18 C12 123.6(3) . . ?
C4 C5 C6 120.8(3) . . ?
C4 C5 H4 119.6 . . ?
C6 C5 H4 119.6 . . ?
O1 C1 C2 118.4(3) . . ?
O1 C1 C6 122.3(3) . . ?
C2 C1 C6 119.3(3) . . ?
N1 C7 C6 121.0(3) . . ?
N1 C7 H5 119.5 . . ?
C6 C7 H5 119.5 . . ?
C10 C00D C17 122.7(3) . . ?
C10 C00D H7 118.6 . . ?
C17 C00D H7 118.6 . . ?
C12 C11 C10 121.1(3) . . ?
C12 C11 H13 119.5 . . ?
C10 C11 H13 119.5 . . ?
C3 C2 C1 121.0(3) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C11 C12 C18 121.9(3) . . ?
C11 C12 H12 119.0 . . ?
C18 C12 H12 119.0 . . ?
C15 C16 C17 119.8(3) . . ?
C15 C16 H8 120.1 . . ?
C17 C16 H8 120.1 . . ?
C2 C3 C4 119.9(3) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 120.5(3) . . ?
C5 C4 Br1 120.2(3) . . ?
C3 C4 Br1 119.3(3) . . ?
C14 C13 C18 121.0(4) . . ?
C14 C13 H11 119.5 . . ?
C18 C13 H11 119.5 . . ?
C13 C14 C15 120.1(4) . . ?
C13 C14 H10 119.9 . . ?
C15 C14 H10 119.9 . . ?
C16 C15 C14 121.8(4) . . ?
C16 C15 H9 119.1 . . ?
C14 C15 H9 119.1 . . ?
C8 C9 H6B 109.5 . . ?
C8 C9 H6A 109.5 . . ?
H6B C9 H6A 109.5 . . ?
C8 C9 H6C 109.5 . . ?
H6B C9 H6C 109.5 . . ?
H6A C9 H6C 109.5 . . ?
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 C4 1.892(4) . ?
O1 C1 1.346(4) . ?
O1 H1 0.8200 . ?
N2 C8 1.281(4) . ?
N2 N1 1.402(4) . ?
N1 C7 1.277(4) . ?
C6 C5 1.392(5) . ?
C6 C1 1.411(5) . ?
C6 C7 1.451(5) . ?
C8 C10 1.475(4) . ?
C8 C9 1.498(5) . ?
C10 C00D 1.375(4) . ?
C10 C11 1.419(5) . ?
C17 C00D 1.408(4) . ?
C17 C18 1.408(4) . ?
C17 C16 1.449(5) . ?
C18 C13 1.410(5) . ?
C18 C12 1.411(5) . ?
C5 C4 1.364(5) . ?
C5 H4 0.9300 . ?
C1 C2 1.380(5) . ?
C7 H5 0.9300 . ?
C00D H7 0.9300 . ?
C11 C12 1.351(5) . ?
C11 H13 0.9300 . ?
C2 C3 1.366(5) . ?
C2 H2 0.9300 . ?
C12 H12 0.9300 . ?
C16 C15 1.316(5) . ?
C16 H8 0.9300 . ?
C3 C4 1.377(5) . ?
C3 H3 0.9300 . ?
C13 C14 1.354(5) . ?
C13 H11 0.9300 . ?
C14 C15 1.404(5) . ?
C14 H10 0.9300 . ?
C15 H9 0.9300 . ?
C9 H6B 0.9600 . ?
C9 H6A 0.9600 . ?
C9 H6C 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
C8 N2 N1 C7 178.0(3) . . . . ?
N1 N2 C8 C10 -179.0(2) . . . . ?
N1 N2 C8 C9 2.9(4) . . . . ?
N2 C8 C10 C00D -174.2(3) . . . . ?
C9 C8 C10 C00D 4.0(5) . . . . ?
N2 C8 C10 C11 5.5(4) . . . . ?
C9 C8 C10 C11 -176.4(3) . . . . ?
C00D C17 C18 C13 -178.2(3) . . . . ?
C16 C17 C18 C13 1.4(4) . . . . ?
C00D C17 C18 C12 1.5(4) . . . . ?
C16 C17 C18 C12 -178.8(3) . . . . ?
C1 C6 C5 C4 -0.7(5) . . . . ?
C7 C6 C5 C4 180.0(3) . . . . ?
C5 C6 C1 O1 -179.5(3) . . . . ?
C7 C6 C1 O1 -0.2(5) . . . . ?
C5 C6 C1 C2 0.4(4) . . . . ?
C7 C6 C1 C2 179.7(3) . . . . ?
N2 N1 C7 C6 -177.8(3) . . . . ?
C5 C6 C7 N1 177.8(3) . . . . ?
C1 C6 C7 N1 -1.5(5) . . . . ?
C11 C10 C00D C17 -0.8(5) . . . . ?
C8 C10 C00D C17 178.9(3) . . . . ?
C18 C17 C00D C10 -0.6(5) . . . . ?
C16 C17 C00D C10 179.7(3) . . . . ?
C00D C10 C11 C12 1.4(5) . . . . ?
C8 C10 C11 C12 -178.3(3) . . . . ?
O1 C1 C2 C3 179.8(3) . . . . ?
C6 C1 C2 C3 -0.1(5) . . . . ?
C10 C11 C12 C18 -0.6(5) . . . . ?
C17 C18 C12 C11 -0.9(5) . . . . ?
C13 C18 C12 C11 178.8(3) . . . . ?
C00D C17 C16 C15 178.7(3) . . . . ?
C18 C17 C16 C15 -1.0(5) . . . . ?
C1 C2 C3 C4 0.2(5) . . . . ?
C6 C5 C4 C3 0.8(5) . . . . ?
C6 C5 C4 Br1 -177.9(2) . . . . ?
C2 C3 C4 C5 -0.5(5) . . . . ?
C2 C3 C4 Br1 178.2(3) . . . . ?
C17 C18 C13 C14 -0.7(5) . . . . ?
C12 C18 C13 C14 179.6(3) . . . . ?
C18 C13 C14 C15 -0.6(6) . . . . ?
C17 C16 C15 C14 -0.3(6) . . . . ?
C13 C14 C15 C16 1.1(6) . . . . ?
