The crucial role of lattice water in directing supramolecular networks of deferiprone analogues: a combined X-ray and DFT study
García-Raso, Ángel; Rocha, Mariana; Terrón, Ángel; Fiol, Juan J.; López-Zafra, Adela; Rodríguez, Carlos A.; Vázquez-López, Ezequiel M.; Barceló-Oliver, Miquel; Frontera, Antonio; CrystEngComm 28 (2026) 951–961; doi:10.1039/D5CE01136A

data_7251501
_publ_section_title
;
 The crucial role of lattice water in directing supramolecular networks of
 deferiprone analogues: a combined X-ray and DFT study
;
_journal_issue                   5
_journal_name_full               CrystEngComm
_journal_page_first              951
_journal_page_last               961
_journal_paper_doi               10.1039/D5CE01136A
_journal_volume                  28
_journal_year                    2026
_chemical_formula_moiety         'C12 H13 N3 O4, 2(H2 O)'
_chemical_formula_sum            'C12 H17 N3 O6'
_chemical_formula_weight         299.28
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2024-06-04
_audit_creation_method
;
Olex2 1.5
(compiled 2024.01.12 svn.r2f8d729c for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-11-24 deposited with the CCDC.	2026-01-06 downloaded from the CCDC.
;
_cell_angle_alpha                89.195(4)
_cell_angle_beta                 88.506(4)
_cell_angle_gamma                68.574(4)
_cell_formula_units_Z            2
_cell_length_a                   7.0597(9)
_cell_length_b                   8.8765(11)
_cell_length_c                   11.2263(14)
_cell_measurement_reflns_used    9974
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      68.39
_cell_measurement_theta_min      6.64
_cell_volume                     654.65(14)
_computing_cell_refinement       'Bruker Apex4, 2021'
_computing_data_collection       'Bruker Apex4, 2021'
_computing_data_reduction        'SAINT v8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0565
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            23230
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.453
_diffrn_reflns_theta_min         5.353
_diffrn_source                   'high brilliance microfocus sealed tube'
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.049
_exptl_absorpt_correction_T_max  0.7476
_exptl_absorpt_correction_T_min  0.5442
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.1704 before and 0.0887 after correction.
The Ratio of minimum to maximum transmission is 0.7279.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_description       prism
_exptl_crystal_F_000             316
_exptl_crystal_recrystallization_method
'The material was recrystallised from water by slow evaporation'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.535
_refine_diff_density_min         -0.563
_refine_diff_density_rms         0.158
_refine_ls_extinction_coef       0.033(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2386
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.137
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0525
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0831P)^2^+0.4008P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1400
_refine_ls_wR_factor_ref         0.1405
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2353
_reflns_number_total             2386
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce01136a2.cif
_cod_data_source_block           1_CCDC1
_cod_database_code               7251501
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.930
_shelx_estimated_absorpt_t_min   0.779
_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 C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O1W(H1WA,H1WB), O2W(H2WA,H2WB)
2.b Ternary CH refined with riding coordinates:
 C7(H7)
2.c Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.d Aromatic/amide H refined with riding coordinates:
 N13(H13), C12(H12), N11(H11), C10(H10), C5(H5), C6(H6)
2.e Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
2.f Idealised tetrahedral OH refined as rotating group:
 O31(H31)
;
_shelx_res_checksum              67109
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a mylar loop in perfluoroether oil'
_olex2_submission_special_instructions 'No special instructions were received'