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#$Date: 2025-07-18 04:25:18 +0300 (Fri, 18 Jul 2025) $
#$Revision: 301288 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/25/06/7250696.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_7250696
loop_
_publ_author_name
'Afri, Michal'
'Gottlieb, Hugo E.'
'Fridman, Natalia'
'Saady, Abed'
_publ_section_title
;
 An NMR insight into the solvatochromic behaviour of Brooker's merocyanine
 dyes
;
_journal_issue                   31
_journal_name_full               'RSC Advances'
_journal_page_first              25436
_journal_page_last               25440
_journal_paper_doi               10.1039/D5RA03758A
_journal_volume                  15
_journal_year                    2025
_chemical_formula_moiety         'C14 H14 N, I, H2 O'
_chemical_formula_sum            'C14 H16 I N O'
_chemical_formula_weight         341.18
_chemical_name_common            Abed17R
_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   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2025-07-01 deposited with the CCDC.	2025-07-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.310(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.3941(10)
_cell_length_b                   10.5533(14)
_cell_length_c                   17.659(2)
_cell_measurement_reflns_used    2433
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.992
_cell_measurement_theta_min      4.890
_cell_volume                     1369.6(3)
_computing_cell_refinement       'CrysAlisPro 1.171.42.54a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.54a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.54a (Rigaku OD, 2022)'
_computing_molecular_graphics    Mercury
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 95
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.922
_diffrn_measurement_device_type  'XtaLAB Synergy-S'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0893
_diffrn_reflns_av_unetI/netI     0.0695
_diffrn_reflns_Laue_measured_fraction_full 0.964
_diffrn_reflns_Laue_measured_fraction_max 0.922
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            5658
_diffrn_reflns_point_group_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.922
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.992
_diffrn_reflns_theta_min         4.890
_exptl_absorpt_coefficient_mu    18.238
_exptl_absorpt_correction_T_max  0.151
_exptl_absorpt_correction_T_min  0.118
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.54a (Rigaku Oxford Diffraction, 2022)
Spherical absorption correction
using equivalent radius and absorption coefficient.
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.655
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.150
_refine_diff_density_max         1.678
_refine_diff_density_min         -2.338
_refine_diff_density_rms         0.252
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2433
_refine_ls_number_restraints     151
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0972
_refine_ls_R_factor_gt           0.0798
_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)+(0.1586P)²+4.5749P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2147
_refine_ls_wR_factor_ref         0.2404
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1918
_reflns_number_total             2433
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5ra03758a2.cif
_cod_data_source_block           Abed17R
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7250696
_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_min   0.138
_shelx_estimated_absorpt_t_max   0.171
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
I1 I 0.64179(9) 0.66887(6) 0.38515(4) 0.0371(4) Uani 0.92 1 d . U P A -1
C6 C 0.0361(14) 0.6552(10) 0.6814(6) 0.036(2) Uani 1 1 d . U . . .
H6A H -0.086389 0.624272 0.663969 0.054 Uiso 1 1 calc R U . . .
H6B H 0.036834 0.692580 0.732221 0.054 Uiso 1 1 calc R U . . .
H6C H 0.122367 0.584469 0.683514 0.054 Uiso 1 1 calc R U . . .
C11 C 0.4676(12) 1.3131(9) 0.3306(6) 0.033(2) Uani 1 1 d . U . . .
H11 H 0.508881 1.394503 0.347808 0.040 Uiso 1 1 calc R U . . .
C5 C 0.0835(13) 0.7234(10) 0.5538(6) 0.035(2) Uani 1 1 d . U . . .
H5 H 0.038193 0.643690 0.535303 0.042 Uiso 1 1 calc R U . . .
C9 C 0.3414(11) 1.1093(9) 0.3551(6) 0.0310(18) Uani 1 1 d . U . . .
C1 C 0.1488(12) 0.8648(10) 0.6558(6) 0.0320(18) Uani 1 1 d . U . . .
H1 H 0.151809 0.883898 0.708508 0.038 Uiso 1 1 calc R U . . .
C13 C 0.4074(13) 1.1653(9) 0.2289(6) 0.035(2) Uani 1 1 d . U . . .
H13 H 0.410017 1.143179 0.176915 0.042 Uiso 1 1 calc R U . . .
C8 C 0.2787(11) 1.0137(9) 0.4060(5) 0.0320(19) Uani 1 1 d . U . . .
H8 H 0.240725 0.934741 0.383840 0.038 Uiso 1 1 calc R U . . .
C4 C 0.1426(13) 0.8095(10) 0.5040(6) 0.036(2) Uani 1 1 d . U . . .
H4 H 0.140495 0.788074 0.451677 0.043 Uiso 1 1 calc R U . . .
C14 C 0.3404(12) 1.0812(10) 0.2784(6) 0.034(2) Uani 1 1 d . U . . .
H14 H 0.292548 1.002254 0.259667 0.041 Uiso 1 1 calc R U . . .
N1 N 0.0886(10) 0.7503(7) 0.6289(4) 0.0293(15) Uani 1 1 d . U . . .
O1 O 0.2393(10) 0.5172(8) 0.4477(4) 0.0485(19) Uani 1 1 d G . . . .
H1A H 0.339273 0.552688 0.440541 0.073 Uiso 1 1 d G U . . .
H1B H 0.255101 0.492217 0.493742 0.073 Uiso 1 1 d G U . . .
C10 C 0.4068(12) 1.2301(10) 0.3809(6) 0.0331(19) Uani 1 1 d . U . . .
H10 H 0.408007 1.252732 0.433012 0.040 Uiso 1 1 calc R U . . .
C12 C 0.4704(12) 1.2815(10) 0.2551(6) 0.034(2) Uani 1 1 d . U . . .
H12 H 0.516017 1.340062 0.221032 0.041 Uiso 1 1 calc R U . . .
C3 C 0.2067(11) 0.9300(9) 0.5296(5) 0.0308(18) Uani 1 1 d . U . . .
C7 C 0.2696(12) 1.0263(10) 0.4793(6) 0.0332(19) Uani 1 1 d . U . . .
H7 H 0.307350 1.105165 0.501639 0.040 Uiso 1 1 calc R U . . .
C2 C 0.2050(12) 0.9522(9) 0.6067(5) 0.0306(18) Uani 1 1 d . U . . .
H2 H 0.245116 1.032376 0.626345 0.037 Uiso 1 1 calc R U . . .
I1B I 0.658(3) 0.6678(15) 0.3447(13) 0.0371(4) Uani 0.04 1 d . U P B -2
I1A I 0.632(3) 0.6674(15) 0.4244(14) 0.0371(4) Uani 0.04 1 d . U P B -2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
N1 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C10 C11 C12 121.2(9) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
N1 C5 C4 120.9(9) . . ?
N1 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C14 C9 C10 118.1(8) . . ?
C14 C9 C8 119.1(9) . . ?
C10 C9 C8 122.8(9) . . ?
N1 C1 C2 119.4(9) . . ?
N1 C1 H1 120.3 . . ?
C2 C1 H1 120.3 . . ?
C12 C13 C14 119.7(9) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C7 C8 C9 126.3(9) . . ?
C7 C8 H8 116.8 . . ?
C9 C8 H8 116.8 . . ?
C5 C4 C3 120.7(9) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C13 C14 C9 121.3(9) . . ?
C13 C14 H14 119.4 . . ?
C9 C14 H14 119.4 . . ?
C5 N1 C1 120.2(8) . . ?
C5 N1 C6 120.2(8) . . ?
C1 N1 C6 119.6(8) . . ?
H1A O1 H1B 104.4 . . ?
C11 C10 C9 119.6(9) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C13 C12 C11 120.1(9) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C2 C3 C4 115.4(8) . . ?
C2 C3 C7 121.3(9) . . ?
C4 C3 C7 123.3(9) . . ?
C8 C7 C3 125.8(9) . . ?
C8 C7 H7 117.1 . . ?
C3 C7 H7 117.1 . . ?
C1 C2 C3 123.3(9) . . ?
C1 C2 H2 118.3 . . ?
C3 C2 H2 118.3 . . ?
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
C6 N1 1.448(12) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C11 C10 1.359(14) . ?
C11 C12 1.377(14) . ?
C11 H11 0.9500 . ?
C5 N1 1.352(12) . ?
C5 C4 1.369(14) . ?
C5 H5 0.9500 . ?
C9 C14 1.385(13) . ?
C9 C10 1.421(14) . ?
C9 C8 1.460(12) . ?
C1 N1 1.356(13) . ?
C1 C2 1.362(13) . ?
C1 H1 0.9500 . ?
C13 C12 1.373(14) . ?
C13 C14 1.376(14) . ?
C13 H13 0.9500 . ?
C8 C7 1.309(13) . ?
C8 H8 0.9500 . ?
C4 C3 1.414(14) . ?
C4 H4 0.9500 . ?
C14 H14 0.9500 . ?
O1 H1A 0.8502 . ?
O1 H1B 0.8508 . ?
C10 H10 0.9500 . ?
C12 H12 0.9500 . ?
C3 C2 1.382(13) . ?
C3 C7 1.460(13) . ?
C7 H7 0.9500 . ?
C2 H2 0.9500 . ?
I1B I1A 1.44(4) . ?
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
C14 C9 C8 C7 -179.2(9) . . . . ?
C10 C9 C8 C7 1.8(15) . . . . ?
N1 C5 C4 C3 -1.5(15) . . . . ?
C12 C13 C14 C9 -2.5(15) . . . . ?
C10 C9 C14 C13 2.6(14) . . . . ?
C8 C9 C14 C13 -176.4(9) . . . . ?
C4 C5 N1 C1 1.5(14) . . . . ?
C4 C5 N1 C6 -176.2(9) . . . . ?
C2 C1 N1 C5 -0.4(13) . . . . ?
C2 C1 N1 C6 177.4(8) . . . . ?
C12 C11 C10 C9 -1.3(14) . . . . ?
C14 C9 C10 C11 -0.7(13) . . . . ?
C8 C9 C10 C11 178.3(8) . . . . ?
C14 C13 C12 C11 0.4(14) . . . . ?
C10 C11 C12 C13 1.5(14) . . . . ?
C5 C4 C3 C2 0.2(14) . . . . ?
C5 C4 C3 C7 -179.3(9) . . . . ?
C9 C8 C7 C3 -180.0(8) . . . . ?
C2 C3 C7 C8 179.0(9) . . . . ?
C4 C3 C7 C8 -1.5(15) . . . . ?
N1 C1 C2 C3 -0.9(14) . . . . ?
C4 C3 C2 C1 1.0(13) . . . . ?
C7 C3 C2 C1 -179.5(8) . . . . ?
