#------------------------------------------------------------------------------
#$Date: 2026-03-21 00:55:42 +0100 (Sat 21 de Mar de 2026) $
#$Revision: 305158 $
#$URL: svn://www.crystallography.net/cod/cif/7/72/07/7720737.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_7720737
loop_
_publ_author_name
'Shaw, Ashwini Kumari'
'Shukla, Nitin'
'Patra, Ashis Kumar'
_publ_section_title
;
 Rational design and evaluation of the sensing mechanism of a
 europium(III)-based luminescent turn-ON chemosensor for citrate
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D5DT02901E
_journal_year                    2026
_chemical_formula_moiety         'C28 H28 N6 O6'
_chemical_formula_sum            'C28 H28 N6 O6'
_chemical_formula_weight         544.56
_chemical_name_systematic        EDTAQUIN
_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
_atom_sites_solution_primary     iterative
_audit_creation_date             2025-09-16
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2023.11.24 svn.r209d9fb2 for OlexSys, GUI svn.r6869)
;
_audit_update_record
;
2025-09-16 deposited with the CCDC.	2026-03-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.143(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.0077(7)
_cell_length_b                   7.3991(5)
_cell_length_c                   15.8713(11)
_cell_measurement_reflns_used    5313
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      28.32
_cell_measurement_theta_min      2.63
_cell_volume                     1241.70(14)
_computing_cell_refinement       'SAINT V8.41 (?, 2016)'
_computing_data_reduction        'SAINT V8.41 (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5-alpha (Bourhis et al., 2015)'
_diffrn_ambient_temperature      273.15
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0581
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            17658
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.047
_diffrn_reflns_theta_max         25.047
_diffrn_reflns_theta_min         3.060
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6819
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1291 before and 0.0653 after correction.
The Ratio of minimum to maximum transmission is 0.9144.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_description       needle
_exptl_crystal_F_000             572
_exptl_crystal_preparation       'Layering DMF:ETHER'
_exptl_crystal_recrystallization_method 'Layering DMF:ETHER'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.224
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2192
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.224
_refine_ls_R_factor_all          0.0902
_refine_ls_R_factor_gt           0.0812
_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)+(0.0316P)²+3.5793P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1530
_refine_ls_wR_factor_ref         0.1570
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1975
_reflns_number_total             2192
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5dt02901e2.cif
_cod_data_source_block           21octa_0m_a
_cod_database_code               7720737
_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   0.979
_shelx_estimated_absorpt_t_min   0.979
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2A), C6(H6), C7(H7), C8(H8), C9(H9), C3(H3), C5(H5)
2.c Idealised tetrahedral OH refined as rotating group with stretchable bonds:
 O2(H2)
;
_olex2_exptl_crystal_mounting_method 'Glass ring'
_olex2_submission_original_sample_id EDTAQUIN
_olex2_submission_special_instructions 'No special instructions were received'
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
O1 O 0.1631(2) 1.0369(3) 0.44484(15) 0.0174(6) Uani 1 1 d . . . . .
O3 O 0.3578(2) 0.4246(3) 0.43067(17) 0.0240(6) Uani 1 1 d . . . . .
O2 O 0.1090(2) 1.2016(3) 0.32175(15) 0.0187(6) Uani 1 1 d . . . . .
H2 H 0.056(4) 1.251(5) 0.3464(17) 0.028 Uiso 1 1 calc R U . . .
N1 N 0.0576(3) 0.6203(4) 0.62282(18) 0.0156(6) Uani 1 1 d . . . . .
N2 N 0.2620(3) 0.6615(4) 0.47961(18) 0.0164(6) Uani 1 1 d . . . . .
H2A H 0.249779 0.776040 0.473220 0.020 Uiso 1 1 calc R U . . .
N3 N 0.3766(3) 0.9093(4) 0.40275(19) 0.0163(6) Uani 1 1 d . . . . .
C2 C 0.1587(3) 0.3302(5) 0.6226(2) 0.0156(7) Uani 1 1 d . . . . .
C1 C 0.0801(3) 0.4467(5) 0.6542(2) 0.0164(8) Uani 1 1 d . . . . .
C6 C 0.0232(3) 0.3858(5) 0.7184(2) 0.0202(8) Uani 1 1 d . . . . .
H6 H -0.029793 0.462343 0.738441 0.024 Uiso 1 1 calc R U . . .
C7 C 0.0458(3) 0.2143(5) 0.7513(2) 0.0208(8) Uani 1 1 d . . . . .
H7 H 0.010183 0.175750 0.794961 0.025 Uiso 1 1 calc R U . . .
C8 C 0.1229(3) 0.0960(5) 0.7192(2) 0.0213(8) Uani 1 1 d . . . . .
H8 H 0.136416 -0.021217 0.740986 0.026 Uiso 1 1 calc R U . . .
C9 C 0.1776(3) 0.1514(5) 0.6570(2) 0.0185(8) Uani 1 1 d . . . . .
H9 H 0.228198 0.071666 0.636467 0.022 Uiso 1 1 calc R U . . .
C3 C 0.2196(3) 0.3966(5) 0.5618(2) 0.0178(8) Uani 1 1 d . . . . .
H3 H 0.271705 0.321706 0.540077 0.021 Uiso 1 1 calc R U . . .
C4 C 0.2011(3) 0.5744(5) 0.5351(2) 0.0161(7) Uani 1 1 d . . . . .
C5 C 0.1148(3) 0.6793(5) 0.5664(2) 0.0162(7) Uani 1 1 d . . . . .
H5 H 0.098041 0.796737 0.545528 0.019 Uiso 1 1 calc R U . . .
C10 C 0.3378(3) 0.5866(5) 0.4350(2) 0.0162(8) Uani 1 1 d . . . . .
C11 C 0.4001(3) 0.7214(5) 0.3882(2) 0.0166(8) Uani 1 1 d . . . . .
H11A H 0.490654 0.700914 0.406642 0.020 Uiso 1 1 calc R U . . .
H11B H 0.370964 0.697542 0.325666 0.020 Uiso 1 1 calc R U . . .
C12 C 0.2799(3) 1.0048(5) 0.3378(2) 0.0191(8) Uani 1 1 d . . . . .
H12A H 0.241006 0.922689 0.290333 0.023 Uiso 1 1 calc R U . . .
H12B H 0.318760 1.102199 0.313656 0.023 Uiso 1 1 calc R U . . .
C13 C 0.1780(3) 1.0827(5) 0.3751(2) 0.0140(7) Uani 1 1 d . . . . .
C14 C 0.4848(3) 1.0157(5) 0.4512(2) 0.0155(7) Uani 1 1 d . . . . .
H14A H 0.466899 1.142947 0.438993 0.019 Uiso 1 1 calc R U . . .
H14B H 0.557805 0.984397 0.431302 0.019 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'
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
C13 O2 H2 109.5 . . ?
C5 N1 C1 119.2(3) . . ?
C4 N2 H2A 116.1 . . ?
C10 N2 H2A 116.1 . . ?
C10 N2 C4 127.8(3) . . ?
C11 N3 C14 116.7(3) . . ?
C12 N3 C11 119.1(3) . . ?
C12 N3 C14 116.4(3) . . ?
C1 C2 C9 118.1(3) . . ?
C3 C2 C1 119.2(3) . . ?
C3 C2 C9 122.7(3) . . ?
N1 C1 C2 120.6(3) . . ?
N1 C1 C6 119.3(3) . . ?
C2 C1 C6 120.1(3) . . ?
C1 C6 H6 119.9 . . ?
C7 C6 C1 120.1(3) . . ?
C7 C6 H6 119.9 . . ?
C6 C7 H7 120.0 . . ?
C6 C7 C8 120.1(3) . . ?
C8 C7 H7 120.0 . . ?
C7 C8 H8 119.7 . . ?
C9 C8 C7 120.7(3) . . ?
C9 C8 H8 119.7 . . ?
C2 C9 H9 119.6 . . ?
C8 C9 C2 120.9(3) . . ?
C8 C9 H9 119.6 . . ?
C2 C3 H3 120.5 . . ?
C4 C3 C2 119.0(3) . . ?
C4 C3 H3 120.5 . . ?
N2 C4 C5 116.9(3) . . ?
C3 C4 N2 125.1(3) . . ?
C3 C4 C5 118.0(3) . . ?
N1 C5 C4 123.7(3) . . ?
N1 C5 H5 118.1 . . ?
C4 C5 H5 118.1 . . ?
O3 C10 N2 125.2(3) . . ?
O3 C10 C11 120.3(3) . . ?
N2 C10 C11 114.6(3) . . ?
N3 C11 C10 115.4(3) . . ?
N3 C11 H11A 108.4 . . ?
N3 C11 H11B 108.4 . . ?
C10 C11 H11A 108.4 . . ?
C10 C11 H11B 108.4 . . ?
H11A C11 H11B 107.5 . . ?
N3 C12 H12A 109.1 . . ?
N3 C12 H12B 109.1 . . ?
N3 C12 C13 112.7(3) . . ?
H12A C12 H12B 107.8 . . ?
C13 C12 H12A 109.1 . . ?
C13 C12 H12B 109.1 . . ?
O1 C13 O2 125.3(3) . . ?
O1 C13 C12 123.5(3) . . ?
O2 C13 C12 111.3(3) . . ?
N3 C14 C14 112.0(3) . 3_676 ?
N3 C14 H14A 109.2 . . ?
N3 C14 H14B 109.2 . . ?
C14 C14 H14A 109.2 3_676 . ?
C14 C14 H14B 109.2 3_676 . ?
H14A C14 H14B 107.9 . . ?
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
O1 C13 1.212(4) . ?
O3 C10 1.225(4) . ?
O2 H2 0.87(4) . ?
O2 C13 1.307(4) . ?
N1 C1 1.375(4) . ?
N1 C5 1.305(4) . ?
N2 H2A 0.8600 . ?
N2 C4 1.403(4) . ?
N2 C10 1.354(4) . ?
N3 C11 1.445(4) . ?
N3 C12 1.444(4) . ?
N3 C14 1.455(4) . ?
C2 C1 1.409(5) . ?
C2 C9 1.424(5) . ?
C2 C3 1.407(5) . ?
C1 C6 1.411(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.368(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.410(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.356(5) . ?
C9 H9 0.9300 . ?
C3 H3 0.9300 . ?
C3 C4 1.380(5) . ?
C4 C5 1.420(5) . ?
C5 H5 0.9300 . ?
C10 C11 1.516(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.519(5) . ?
C14 C14 1.510(6) 3_676 ?
C14 H14A 0.9700 . ?
C14 H14B 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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 C10 C11 N3 -175.9(3) . . . . ?
N1 C1 C6 C7 -179.1(3) . . . . ?
N2 C4 C5 N1 -175.3(3) . . . . ?
N2 C10 C11 N3 4.1(4) . . . . ?
N3 C12 C13 O1 -15.7(5) . . . . ?
N3 C12 C13 O2 165.3(3) . . . . ?
C2 C1 C6 C7 1.1(5) . . . . ?
C2 C3 C4 N2 175.6(3) . . . . ?
C2 C3 C4 C5 -3.7(5) . . . . ?
C1 N1 C5 C4 -0.4(5) . . . . ?
C1 C2 C9 C8 -0.9(5) . . . . ?
C1 C2 C3 C4 0.2(5) . . . . ?
C1 C6 C7 C8 -2.0(5) . . . . ?
C6 C7 C8 C9 1.4(5) . . . . ?
C7 C8 C9 C2 0.1(5) . . . . ?
C9 C2 C1 N1 -179.5(3) . . . . ?
C9 C2 C1 C6 0.3(5) . . . . ?
C9 C2 C3 C4 -176.8(3) . . . . ?
C3 C2 C1 N1 3.5(5) . . . . ?
C3 C2 C1 C6 -176.8(3) . . . . ?
C3 C2 C9 C8 176.1(3) . . . . ?
C3 C4 C5 N1 4.0(5) . . . . ?
C4 N2 C10 O3 6.0(6) . . . . ?
C4 N2 C10 C11 -173.9(3) . . . . ?
C5 N1 C1 C2 -3.4(5) . . . . ?
C5 N1 C1 C6 176.9(3) . . . . ?
C10 N2 C4 C3 7.8(5) . . . . ?
C10 N2 C4 C5 -172.9(3) . . . . ?
C11 N3 C12 C13 121.7(3) . . . . ?
C11 N3 C14 C14 -79.5(4) . . . 3_676 ?
C12 N3 C11 C10 -98.6(4) . . . . ?
C12 N3 C14 C14 131.5(4) . . . 3_676 ?
C14 N3 C11 C10 113.3(3) . . . . ?
C14 N3 C12 C13 -90.1(4) . . . . ?
