#------------------------------------------------------------------------------
#$Date: 2025-08-21 23:04:39 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301851 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/83/7058329.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_7058329
loop_
_publ_author_name
'Sharada, Durgam'
'Saha, Arijit'
'Saha, Binoy K.'
_publ_section_title
;
 Charge transfer complexes as colour changing and
 disappearing--reappearing colour materials
;
_journal_issue                   20
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              7562
_journal_paper_doi               10.1039/C9NJ00823C
_journal_volume                  43
_journal_year                    2019
_chemical_formula_moiety         'C6 H3 N3 O6, 2(C5 H7)'
_chemical_formula_sum            'C16 H17 N3 O6'
_chemical_formula_weight         347.32
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2019-02-06
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2019-02-09 deposited with the CCDC.    2019-04-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.294(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.0581(5)
_cell_length_b                   10.7355(4)
_cell_length_c                   15.7163(8)
_cell_measurement_reflns_used    5803
_cell_measurement_temperature    226.00(14)
_cell_measurement_theta_max      29.0830
_cell_measurement_theta_min      3.1259
_cell_volume                     1692.26(14)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      226.00(14)
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.897
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -23.00    3.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.0272  -57.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega  -19.00   21.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.0272  -99.0000   30.0000 40

#__ type_ start__ end____ width___ exp.time_
  3 omega  -42.00   53.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.0272   37.0000   30.0000 95

#__ type_ start__ end____ width___ exp.time_
  4 omega  -23.00    3.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.0272  -99.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
  5 omega  -81.00  -50.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.0272 -178.0000  -60.0000 31

#__ type_ start__ end____ width___ exp.time_
  6 omega  -17.00   13.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.0272  -99.0000 -180.0000 30

#__ type_ start__ end____ width___ exp.time_
  7 omega  -85.00    8.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.0272  -37.0000 -150.0000 93

#__ type_ start__ end____ width___ exp.time_
  8 omega  -25.00   17.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.0272  -99.0000   90.0000 42

#__ type_ start__ end____ width___ exp.time_
  9 omega   -6.00   20.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.0272  -99.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 10 omega  -25.00    1.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.0272  -99.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
 11 omega  -30.00    2.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.0272   37.0000 -150.0000 32

#__ type_ start__ end____ width___ exp.time_
 12 omega    9.00   36.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.0272   37.0000 -150.0000 27

#__ type_ start__ end____ width___ exp.time_
 13 omega  -27.00    2.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.0272  123.0000   70.0000 29

#__ type_ start__ end____ width___ exp.time_
 14 omega  -84.00  -41.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.0272  -57.0000  120.0000 43
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0311577000
_diffrn_orient_matrix_UB_12      0.0012250000
_diffrn_orient_matrix_UB_13      -0.0390216000
_diffrn_orient_matrix_UB_21      -0.0618620000
_diffrn_orient_matrix_UB_22      -0.0142399000
_diffrn_orient_matrix_UB_23      -0.0225413000
_diffrn_orient_matrix_UB_31      -0.0142398000
_diffrn_orient_matrix_UB_32      0.0645022000
_diffrn_orient_matrix_UB_33      -0.0042366000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.897
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            18964
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.897
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         29.147
_diffrn_reflns_theta_min         3.132
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89735
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_description       plate
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.68
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       0.014(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         4100
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0824
_refine_ls_R_factor_gt           0.0660
_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)+(0.0574P)²+1.9058P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1755
_refine_ls_wR_factor_ref         0.1855
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3216
_reflns_number_total             4100
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9nj00823c2.cif
_cod_data_source_block           DR-TN
_cod_depositor_comments
'Adding full bibliography for 7058327--7058331.cif.'
_cod_original_cell_volume        1692.28(13)
_cod_database_code               7058329
_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.
;
_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:
 C4(H4), C6(H6), C2(H2), C7(H7), C12(H12)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C10(H10A,H10B,H10C), C15(H15A,H15B,H15C), C16(H16A,H16B,
 H16C)
;
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
O6 O 0.43468(18) 0.0920(2) 0.44428(14) 0.0549(5) Uani 1 1 d .
O5 O 0.5771(2) 0.0222(2) 0.35919(13) 0.0657(7) Uani 1 1 d .
O3 O 1.0498(2) 0.3833(2) 0.44927(18) 0.0716(7) Uani 1 1 d .
N3 N 0.5455(2) 0.0888(2) 0.41777(13) 0.0410(5) Uani 1 1 d .
O4 O 0.9621(2) 0.2959(2) 0.33403(15) 0.0716(7) Uani 1 1 d .
O1 O 0.8104(2) 0.3859(2) 0.70253(14) 0.0680(7) Uani 1 1 d .
O2 O 0.6288(2) 0.2798(2) 0.70682(13) 0.0638(6) Uani 1 1 d .
N1 N 0.7227(3) 0.3191(2) 0.66984(14) 0.0463(5) Uani 1 1 d .
N2 N 0.9623(2) 0.3230(2) 0.40915(17) 0.0482(6) Uani 1 1 d .
C5 C 0.6489(2) 0.1690(2) 0.45951(14) 0.0306(5) Uani 1 1 d .
C4 C 0.7565(2) 0.2023(2) 0.41480(14) 0.0329(5) Uani 1 1 d .
H4 H 0.765945 0.173343 0.359122 0.039 Uiso 1 1 calc R
C3 C 0.8496(2) 0.2802(2) 0.45607(15) 0.0336(5) Uani 1 1 d .
C1 C 0.7324(2) 0.2813(2) 0.58045(14) 0.0333(5) Uani 1 1 d .
C6 C 0.6333(2) 0.2073(2) 0.54231(14) 0.0327(5) Uani 1 1 d .
H6 H 0.558619 0.183894 0.571109 0.039 Uiso 1 1 calc R
C2 C 0.8409(2) 0.3211(2) 0.53885(16) 0.0357(5) Uani 1 1 d .
H2 H 0.905924 0.373770 0.565652 0.043 Uiso 1 1 calc R
C9 C 0.4535(3) 0.4394(2) 0.42356(15) 0.0387(5) Uani 1 1 d .
C8 C 0.5694(2) 0.5113(2) 0.42549(16) 0.0389(5) Uani 1 1 d .
C7 C 0.6127(2) 0.5705(2) 0.50189(16) 0.0403(6) Uani 1 1 d .
H7 H 0.690424 0.619288 0.503030 0.048 Uiso 1 1 calc R
C11 C 0.4012(3) 0.3728(3) 0.34337(18) 0.0554(7) Uani 1 1 d .
H11A H 0.383256 0.432996 0.297926 0.083 Uiso 1 1 calc GR
H11B H 0.319490 0.329238 0.353851 0.083 Uiso 1 1 calc GR
H11C H 0.467097 0.313356 0.326770 0.083 Uiso 1 1 calc GR
C10 C 0.6467(3) 0.5266(3) 0.34727(19) 0.0583(8) Uani 1 1 d .
H10A H 0.664536 0.445258 0.323734 0.087 Uiso 1 1 calc GR
H10B H 0.730418 0.568524 0.362954 0.087 Uiso 1 1 calc GR
H10C H 0.594883 0.575738 0.304960 0.087 Uiso 1 1 calc GR
C14 C -0.0585(2) 0.9315(2) 0.43052(16) 0.0396(5) Uani 1 1 d .
C13 C 0.0541(2) 1.0045(2) 0.41957(15) 0.0385(5) Uani 1 1 d .
C12 C 0.1099(2) 1.0711(2) 0.48939(16) 0.0409(6) Uani 1 1 d .
H12 H 0.185686 1.120165 0.482283 0.049 Uiso 1 1 calc R
C15 C 0.1143(3) 1.0133(3) 0.33479(18) 0.0547(7) Uani 1 1 d .
H15A H 0.132283 0.930253 0.314279 0.082 Uiso 1 1 calc GR
H15B H 0.196885 1.060167 0.341525 0.082 Uiso 1 1 calc GR
H15C H 0.052432 1.055253 0.294005 0.082 Uiso 1 1 calc GR
C16 C -0.1245(3) 0.8558(3) 0.3579(2) 0.0579(8) Uani 1 1 d .
H16A H -0.145980 0.909777 0.309243 0.087 Uiso 1 1 calc GR
H16B H -0.205606 0.818438 0.375793 0.087 Uiso 1 1 calc GR
H16C H -0.064138 0.790825 0.341937 0.087 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'
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
O6 N3 O5 124.6(2) . .
O6 N3 C5 117.8(2) . .
O5 N3 C5 117.6(2) . .
O1 N1 O2 124.3(2) . .
O1 N1 C1 117.8(2) . .
O2 N1 C1 117.9(2) . .
O3 N2 C3 117.2(2) . .
O4 N2 O3 125.0(2) . .
O4 N2 C3 117.8(2) . .
C4 C5 N3 118.7(2) . .
C4 C5 C6 123.3(2) . .
C6 C5 N3 117.9(2) . .
C5 C4 H4 121.7 . .
C3 C4 C5 116.6(2) . .
C3 C4 H4 121.7 . .
C4 C3 N2 118.3(2) . .
C4 C3 C2 123.1(2) . .
C2 C3 N2 118.6(2) . .
C6 C1 N1 118.5(2) . .
C6 C1 C2 123.0(2) . .
C2 C1 N1 118.6(2) . .
C5 C6 H6 121.6 . .
C1 C6 C5 116.8(2) . .
C1 C6 H6 121.6 . .
C3 C2 H2 121.5 . .
C1 C2 C3 117.1(2) . .
C1 C2 H2 121.5 . .
C8 C9 C11 121.2(2) . .
C7 C9 C8 118.3(2) 3_666 .
C7 C9 C11 120.5(2) 3_666 .
C9 C8 C7 118.4(2) . .
C9 C8 C10 121.4(3) . .
C7 C8 C10 120.1(3) . .
C9 C7 C8 123.3(2) 3_666 .
C9 C7 H7 118.3 3_666 .
C8 C7 H7 118.3 . .
C9 C11 H11A 109.5 . .
C9 C11 H11B 109.5 . .
C9 C11 H11C 109.5 . .
H11A C11 H11B 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C8 C10 H10A 109.5 . .
C8 C10 H10B 109.5 . .
C8 C10 H10C 109.5 . .
H10A C10 H10B 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
C13 C14 C16 121.4(2) . .
C12 C14 C13 118.7(2) 3_576 .
C12 C14 C16 119.9(3) 3_576 .
C14 C13 C15 121.8(2) . .
C12 C13 C14 118.2(2) . .
C12 C13 C15 120.0(2) . .
C14 C12 H12 118.5 3_576 .
C13 C12 C14 123.1(2) . 3_576
C13 C12 H12 118.5 . .
C13 C15 H15A 109.5 . .
C13 C15 H15B 109.5 . .
C13 C15 H15C 109.5 . .
H15A C15 H15B 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
C14 C16 H16A 109.5 . .
C14 C16 H16B 109.5 . .
C14 C16 H16C 109.5 . .
H16A C16 H16B 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O6 N3 1.220(3) .
O5 N3 1.226(3) .
O3 N2 1.228(3) .
N3 C5 1.466(3) .
O4 N2 1.216(3) .
O1 N1 1.220(3) .
O2 N1 1.221(3) .
N1 C1 1.473(3) .
N2 C3 1.471(3) .
C5 C4 1.381(3) .
C5 C6 1.385(3) .
C4 H4 0.9400 .
C4 C3 1.380(3) .
C3 C2 1.382(3) .
C1 C6 1.377(3) .
C1 C2 1.381(3) .
C6 H6 0.9400 .
C2 H2 0.9400 .
C9 C8 1.397(4) .
C9 C7 1.395(4) 3_666
C9 C11 1.509(4) .
C8 C7 1.399(4) .
C8 C10 1.512(4) .
C7 H7 0.9400 .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C11 H11C 0.9700 .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C10 H10C 0.9700 .
C14 C13 1.399(4) .
C14 C12 1.396(4) 3_576
C14 C16 1.513(4) .
C13 C12 1.392(4) .
C13 C15 1.507(4) .
C12 H12 0.9400 .
C15 H15A 0.9700 .
C15 H15B 0.9700 .
C15 H15C 0.9700 .
C16 H16A 0.9700 .
C16 H16B 0.9700 .
C16 H16C 0.9700 .
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_4
O6 N3 C5 C4 -157.0(2) . .
O6 N3 C5 C6 23.2(3) . .
O5 N3 C5 C4 23.8(3) . .
O5 N3 C5 C6 -156.1(2) . .
O3 N2 C3 C4 -173.9(2) . .
O3 N2 C3 C2 7.0(3) . .
N3 C5 C4 C3 178.52(19) . .
N3 C5 C6 C1 179.27(19) . .
O4 N2 C3 C4 6.0(3) . .
O4 N2 C3 C2 -173.2(2) . .
O1 N1 C1 C6 -179.2(2) . .
O1 N1 C1 C2 1.2(3) . .
O2 N1 C1 C6 2.2(3) . .
O2 N1 C1 C2 -177.5(2) . .
N1 C1 C6 C5 -177.2(2) . .
N1 C1 C2 C3 177.7(2) . .
N2 C3 C2 C1 178.7(2) . .
C5 C4 C3 N2 -177.0(2) . .
C5 C4 C3 C2 2.2(3) . .
C4 C5 C6 C1 -0.6(3) . .
C4 C3 C2 C1 -0.4(3) . .
C6 C5 C4 C3 -1.6(3) . .
C6 C1 C2 C3 -2.0(3) . .
C2 C1 C6 C5 2.5(3) . .
C9 C8 C7 C9 0.4(4) . 3_666
C7 C9 C8 C7 -0.4(4) 3_666 .
C7 C9 C8 C10 -179.9(2) 3_666 .
C11 C9 C8 C7 -179.9(2) . .
C11 C9 C8 C10 0.5(4) . .
C10 C8 C7 C9 180.0(2) . 3_666
C14 C13 C12 C14 -0.1(4) . 3_576
C12 C14 C13 C12 0.1(4) 3_576 .
C12 C14 C13 C15 -179.2(2) 3_576 .
C15 C13 C12 C14 179.2(2) . 3_576
C16 C14 C13 C12 -179.7(2) . .
C16 C14 C13 C15 1.0(4) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139179245
