#------------------------------------------------------------------------------
#$Date: 2025-03-04 21:15:35 +0200 (Tue, 04 Mar 2025) $
#$Revision: 298119 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/33/1573310.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_1573310
loop_
_publ_author_name
'Mandal, Mrinal'
'Mardanya, Sukumar'
'Saha, Arijit'
'Singh, Manjeev'
'Ghosh, Swarnali'
'Chatterjee, Tanmay'
'Patra, Ramen'
'Bhunia, Surojit'
'Mandal, Saptarshi'
'Mukherjee, Soumen'
'Debnath, Rahul'
'Reddy, C. Malla'
'Das, Mousumi'
'Mandal, Prasun K.'
_publ_section_title
;
 Charge-transfer mediated J-aggregation in red emitting
 ultra-small-single-benzenic meta-fluorophore crystals.
;
_journal_issue                   2
_journal_name_full               'Chemical science'
_journal_page_first              901
_journal_page_last               909
_journal_paper_doi               10.1039/d4sc06851c
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C12 H11 N3'
_chemical_formula_sum            'C12 H11 N3'
_chemical_formula_weight         197.24
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2020-10-31
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2022-10-01 deposited with the CCDC.	2024-11-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.614(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.292(4)
_cell_length_b                   10.450(3)
_cell_length_c                   6.872(2)
_cell_measurement_reflns_used    2119
_cell_measurement_temperature    301(2)
_cell_measurement_theta_max      26.76
_cell_measurement_theta_min      3.32
_cell_volume                     1088.5(5)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      301.05
_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_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1244
_diffrn_reflns_av_unetI/netI     0.0987
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            8292
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.367
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.4157
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1464 before and 0.0925 after correction.
The Ratio of minimum to maximum transmission is 0.5576.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear reddish orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_description       needle
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       0.027(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         1908
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.126
_refine_ls_R_factor_all          0.1509
_refine_ls_R_factor_gt           0.1058
_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)+(0.0961P)²+1.4564P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2431
_refine_ls_wR_factor_ref         0.2667
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1260
_reflns_number_total             1908
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc06851c2.cif
_cod_data_source_block           test5_a
_cod_depositor_comments
'Adding full bibliography for 1573309--1573310.cif.'
_cod_database_code               1573310
_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.
;
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.956
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C003(H003), C005(H005), C009(H009), C00C(H00C), C00D(H00D)
2.b Idealised Me refined as rotating group:
 C00E(H00A,H00B,H00E), C00F(H00F,H00G,H00H)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
N001 N 0.6332(3) 0.0121(4) 0.2874(6) 0.0562(12) Uani 1 1 d . . . . .
C002 C 0.8350(3) 0.2086(4) 0.3462(6) 0.0346(10) Uani 1 1 d . . . . .
C003 C 0.8656(3) 0.3398(4) 0.3559(6) 0.0385(11) Uani 1 1 d . . . . .
H003 H 0.926612 0.348716 0.373947 0.046 Uiso 1 1 calc R . . . .
C004 C 0.8212(3) 0.4506(4) 0.3434(6) 0.0373(11) Uani 1 1 d . . . . .
C005 C 0.7463(3) 0.1735(4) 0.3227(6) 0.0376(11) Uani 1 1 d . . . . .
H005 H 0.703234 0.236884 0.314119 0.045 Uiso 1 1 calc R . . . .
C006 C 0.7277(3) 0.4665(4) 0.3139(7) 0.0446(12) Uani 1 1 d . . . . .
C007 C 0.7205(3) 0.0445(4) 0.3117(6) 0.0431(11) Uani 1 1 d . . . . .
N008 N 0.6532(3) 0.4830(5) 0.2922(8) 0.0729(15) Uani 1 1 d . . . . .
C009 C 0.9000(3) 0.1144(5) 0.3609(6) 0.0470(12) Uani 1 1 d . . . . .
H009 H 0.959355 0.136742 0.375537 0.056 Uiso 1 1 calc R . . . .
N00A N 0.9109(3) 0.6599(4) 0.3782(8) 0.0720(14) Uani 1 1 d . . . . .
C00B C 0.8704(3) 0.5685(5) 0.3608(7) 0.0483(12) Uani 1 1 d . . . . .
C00C C 0.7873(4) -0.0465(5) 0.3296(7) 0.0522(13) Uani 1 1 d . . . . .
H00C H 0.772217 -0.132735 0.325233 0.063 Uiso 1 1 calc R . . . .
C00D C 0.8748(3) -0.0132(5) 0.3535(7) 0.0520(13) Uani 1 1 d . . . . .
H00D H 0.917699 -0.076792 0.364808 0.062 Uiso 1 1 calc R . . . .
C00E C 0.5654(3) 0.1101(6) 0.2684(10) 0.0781(19) Uani 1 1 d . . . . .
H00A H 0.572789 0.163726 0.382781 0.117 Uiso 1 1 calc GR . . . .
H00B H 0.508341 0.070390 0.255665 0.117 Uiso 1 1 calc GR . . . .
H00E H 0.570282 0.161036 0.154034 0.117 Uiso 1 1 calc GR . . . .
C00F C 0.6056(5) -0.1197(6) 0.2803(10) 0.088(2) Uani 1 1 d . . . . .
H00F H 0.634034 -0.164620 0.184262 0.132 Uiso 1 1 calc GR . . . .
H00G H 0.542742 -0.124039 0.245021 0.132 Uiso 1 1 calc GR . . . .
H00H H 0.621442 -0.158301 0.406760 0.132 Uiso 1 1 calc GR . . . .
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'
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
C007 N001 C00E 120.7(4) . . ?
C007 N001 C00F 121.3(5) . . ?
C00F N001 C00E 118.0(5) . . ?
C005 C002 C003 123.9(4) . . ?
C009 C002 C003 116.3(4) . . ?
C009 C002 C005 119.8(4) . . ?
C002 C003 H003 114.4 . . ?
C004 C003 C002 131.2(4) . . ?
C004 C003 H003 114.4 . . ?
C003 C004 C006 126.8(4) . . ?
C003 C004 C00B 118.6(4) . . ?
C006 C004 C00B 114.5(4) . . ?
C002 C005 H005 119.3 . . ?
C002 C005 C007 121.4(4) . . ?
C007 C005 H005 119.3 . . ?
N008 C006 C004 177.9(5) . . ?
N001 C007 C005 120.5(4) . . ?
N001 C007 C00C 122.4(4) . . ?
C00C C007 C005 117.0(4) . . ?
C002 C009 H009 120.5 . . ?
C00D C009 C002 119.0(4) . . ?
C00D C009 H009 120.5 . . ?
N00A C00B C004 178.1(5) . . ?
C007 C00C H00C 118.9 . . ?
C00D C00C C007 122.1(4) . . ?
C00D C00C H00C 118.9 . . ?
C009 C00D H00D 119.7 . . ?
C00C C00D C009 120.7(4) . . ?
C00C C00D H00D 119.7 . . ?
N001 C00E H00A 109.5 . . ?
N001 C00E H00B 109.5 . . ?
N001 C00E H00E 109.5 . . ?
H00A C00E H00B 109.5 . . ?
H00A C00E H00E 109.5 . . ?
H00B C00E H00E 109.5 . . ?
N001 C00F H00F 109.5 . . ?
N001 C00F H00G 109.5 . . ?
N001 C00F H00H 109.5 . . ?
H00F C00F H00G 109.5 . . ?
H00F C00F H00H 109.5 . . ?
H00G C00F H00H 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
N001 C007 1.366(6) . ?
N001 C00E 1.450(7) . ?
N001 C00F 1.440(7) . ?
C002 C003 1.447(6) . ?
C002 C005 1.394(6) . ?
C002 C009 1.393(6) . ?
C003 H003 0.9300 . ?
C003 C004 1.339(6) . ?
C004 C006 1.427(6) . ?
C004 C00B 1.440(6) . ?
C005 H005 0.9300 . ?
C005 C007 1.403(6) . ?
C006 N008 1.142(6) . ?
C007 C00C 1.389(7) . ?
C009 H009 0.9300 . ?
C009 C00D 1.387(7) . ?
N00A C00B 1.136(6) . ?
C00C H00C 0.9300 . ?
C00C C00D 1.371(7) . ?
C00D H00D 0.9300 . ?
C00E H00A 0.9600 . ?
C00E H00B 0.9600 . ?
C00E H00E 0.9600 . ?
C00F H00F 0.9600 . ?
C00F H00G 0.9600 . ?
C00F H00H 0.9600 . ?
