#------------------------------------------------------------------------------
#$Date: 2023-05-05 05:51:37 +0300 (Fri, 05 May 2023) $
#$Revision: 283373 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/22/7062259.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_7062259
loop_
_publ_author_name
'Ahangar, Aadil A.'
'Ahmad, Ishtiyaq'
'Dar, Aijaz A.'
_publ_section_title
;
 AIE in the halogenated anils and their utilization as fluorescent probes
 for explosive nitro-aromatics
;
_journal_issue                   10
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              4775
_journal_page_last               4783
_journal_paper_doi               10.1039/D2NJ05306C
_journal_volume                  47
_journal_year                    2023
_chemical_formula_moiety         'C13 H8 Cl I2 N O'
_chemical_formula_sum            'C13 H8 Cl I2 N O'
_chemical_formula_weight         483.45
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/1
_audit_update_record
;
2022-06-04 deposited with the CCDC.	2023-02-06 downloaded from the CCDC.
;
_cell_angle_alpha                87.144(2)
_cell_angle_beta                 76.439(2)
_cell_angle_gamma                66.457(3)
_cell_formula_units_Z            2
_cell_length_a                   7.9582(2)
_cell_length_b                   8.5499(2)
_cell_length_c                   11.2354(3)
_cell_measurement_reflns_used    2251
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.0000
_cell_measurement_theta_min      2.3450
_cell_volume                     680.48(3)
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type
'Saxi-CrysAlisPro-abstract goniometer imported SAXI images'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0139
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4832
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.602
_exptl_absorpt_coefficient_mu    4.804
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91468
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    2.364
_exptl_crystal_description       needle
_exptl_crystal_F_000             450
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.623
_refine_diff_density_min         -0.809
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2387
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0228
_refine_ls_R_factor_gt           0.0210
_refine_ls_shift/su_max          0.054
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0244P)²+1.0701P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0501
_refine_ls_wR_factor_ref         0.0512
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2251
_reflns_number_total             2387
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2nj05306c2.cif
_cod_data_source_block           MAA15
_cod_depositor_comments
'Adding full bibliography for 7062258--7062260.cif.'
_cod_database_code               7062259
_shelx_shelxl_version_number     2018/1
_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   0.596
_shelx_estimated_absorpt_t_max   0.795
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
I1 I 0.71804(3) 0.13346(3) 0.99112(2) 0.03025(9) Uani 1 1 d . . . . .
I2 I 0.11719(3) 0.33103(3) 0.12351(2) 0.03067(9) Uani 1 1 d . . . . .
Cl1 Cl -0.19685(13) 1.02483(11) 0.30852(9) 0.0338(2) Uani 1 1 d . . . . .
O1 O 0.2884(3) 0.3084(3) 0.3483(2) 0.0285(6) Uani 1 1 d . . . . .
N1 N 0.3454(4) 0.3979(4) 0.5447(3) 0.0240(6) Uani 1 1 d . . . . .
C4 C 0.4274(4) 0.3486(4) 0.6471(3) 0.0218(7) Uani 1 1 d . . . . .
C3 C 0.4197(5) 0.4598(4) 0.7360(3) 0.0256(7) Uani 1 1 d . . . . .
H3 H 0.357087 0.579580 0.729916 0.031 Uiso 1 1 calc R U . . .
C5 C 0.5219(5) 0.1742(5) 0.6567(3) 0.0273(8) Uani 1 1 d . . . . .
H5 H 0.529874 0.097142 0.595486 0.033 Uiso 1 1 calc R U . . .
C1 C 0.5946(4) 0.2233(4) 0.8418(3) 0.0231(7) Uani 1 1 d . . . . .
C11 C -0.0309(5) 0.6922(4) 0.2353(3) 0.0244(7) Uani 1 1 d . . . . .
H11 H -0.090372 0.725313 0.168623 0.029 Uiso 1 1 calc R U . . .
C12 C -0.0564(5) 0.8118(4) 0.3228(3) 0.0247(7) Uani 1 1 d . . . . .
C9 C 0.1750(5) 0.4726(4) 0.3422(3) 0.0235(7) Uani 1 1 d . . . . .
C8 C 0.1448(5) 0.5979(4) 0.4306(3) 0.0230(7) Uani 1 1 d . . . . .
C2 C 0.5025(5) 0.3977(4) 0.8337(3) 0.0266(8) Uani 1 1 d . . . . .
H2 H 0.496007 0.474414 0.894602 0.032 Uiso 1 1 calc R U . . .
C6 C 0.6048(5) 0.1104(4) 0.7539(3) 0.0278(8) Uani 1 1 d . . . . .
H6 H 0.667802 -0.009267 0.760053 0.033 Uiso 1 1 calc R U . . .
C10 C 0.0836(5) 0.5216(4) 0.2461(3) 0.0228(7) Uani 1 1 d . . . . .
C7 C 0.2316(5) 0.5515(4) 0.5344(3) 0.0234(7) Uani 1 1 d . . . . .
H7 H 0.203588 0.636548 0.595841 0.028 Uiso 1 1 calc R U . . .
C13 C 0.0280(5) 0.7678(4) 0.4199(3) 0.0255(7) Uani 1 1 d . . . . .
H13 H 0.006933 0.852638 0.479608 0.031 Uiso 1 1 calc R U . . .
H1A H 0.337(8) 0.316(7) 0.418(6) 0.079(18) Uiso 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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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
C9 O1 H1A 101(3) . . ?
C7 N1 C4 122.1(3) . . ?
C5 C4 C3 118.8(3) . . ?
C5 C4 N1 115.9(3) . . ?
C3 C4 N1 125.3(3) . . ?
C2 C3 C4 120.6(3) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C6 C5 C4 121.2(3) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C6 C1 C2 120.8(3) . . ?
C6 C1 I1 120.6(2) . . ?
C2 C1 I1 118.6(2) . . ?
C12 C11 C10 118.9(3) . . ?
C12 C11 H11 120.6 . . ?
C10 C11 H11 120.6 . . ?
C13 C12 C11 121.8(3) . . ?
C13 C12 Cl1 119.2(3) . . ?
C11 C12 Cl1 118.9(3) . . ?
O1 C9 C10 119.5(3) . . ?
O1 C9 C8 121.8(3) . . ?
C10 C9 C8 118.8(3) . . ?
C13 C8 C9 119.9(3) . . ?
C13 C8 C7 119.5(3) . . ?
C9 C8 C7 120.6(3) . . ?
C1 C2 C3 119.6(3) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C1 C6 C5 119.1(3) . . ?
C1 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C11 C10 C9 120.9(3) . . ?
C11 C10 I2 121.3(2) . . ?
C9 C10 I2 117.8(2) . . ?
N1 C7 C8 121.1(3) . . ?
N1 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
C12 C13 C8 119.7(3) . . ?
C12 C13 H13 120.1 . . ?
C8 C13 H13 120.1 . . ?
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
I1 C1 2.100(3) . ?
I2 C10 2.080(3) . ?
Cl1 C12 1.738(3) . ?
O1 C9 1.341(4) . ?
O1 H1A 0.96(6) . ?
N1 C7 1.281(4) . ?
N1 C4 1.419(4) . ?
C4 C5 1.388(5) . ?
C4 C3 1.388(5) . ?
C3 C2 1.386(5) . ?
C3 H3 0.9500 . ?
C5 C6 1.384(5) . ?
C5 H5 0.9500 . ?
C1 C6 1.381(5) . ?
C1 C2 1.384(5) . ?
C11 C12 1.377(5) . ?
C11 C10 1.395(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.373(5) . ?
C9 C10 1.397(5) . ?
C9 C8 1.407(5) . ?
C8 C13 1.394(5) . ?
C8 C7 1.452(5) . ?
C2 H2 0.9500 . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C13 H13 0.9500 . ?
