Designing lenalidomide cocrystals with an extended-release profile for improved pulmonary drug delivery
Screen, Martin A.; Tomkinson, Gary; McCabe, James F.; Askin, Sean; Mahon, Clare S.; Wilson, Mark R.; Steed, Jonathan W.; New Journal of Chemistry 49 (2025) 6535–6543; doi:10.1039/D5NJ00425J

data_7063723
_publ_section_title
;
 Designing lenalidomide cocrystals with an extended-release profile for
 improved pulmonary drug delivery
;
_journal_issue                   16
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              6535
_journal_page_last               6543
_journal_paper_doi               10.1039/D5NJ00425J
_journal_volume                  49
_journal_year                    2025
_chemical_formula_moiety         'C13 H13 N3 O3, C3 H6 N6, C H5 O1.5'
_chemical_formula_sum            'C17 H24 N9 O4.5'
_chemical_formula_weight         426.45
_chemical_name_systematic        'Lenalidomide melamine methanol hemihydrate'
_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     direct
_audit_creation_date             2023-06-22
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2024-11-14 deposited with the CCDC.	2025-03-31 downloaded from the CCDC.
;
_cell_angle_alpha                93.5640(10)
_cell_angle_beta                 94.6780(10)
_cell_angle_gamma                111.0870(10)
_cell_formula_units_Z            2
_cell_length_a                   7.9402(3)
_cell_length_b                   10.2062(3)
_cell_length_c                   12.5527(4)
_cell_measurement_reflns_used    9426
_cell_measurement_temperature    120.00
_cell_measurement_theta_max      31.37
_cell_measurement_theta_min      2.83
_cell_volume                     941.39(5)
_computing_cell_refinement       'SAINT v8.40A (Bruker AXS, 2019)'
_computing_data_collection       'APEX4 v.2022.10_0 (Bruker AXS, 2022)'
_computing_data_reduction        'SAINT v8.40A (Bruker AXS, 2019)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      120.00
_diffrn_detector                 'Bruker PHOTON III C14 MM CPAD'
_diffrn_detector_area_resol_mean 54.4
_diffrn_detector_type            'CPA sensor'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Bruker D8 Venture'
_diffrn_measurement_device_type  '3-circle diffractometer'
_diffrn_measurement_method       '\w- and \f-scan'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0639
_diffrn_reflns_av_unetI/netI     0.0424
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            29232
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.999
_diffrn_reflns_theta_min         2.767
_diffrn_source                   'Incoatec I\mS 3.0 microsource'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_type              'microfocus sealed X-ray tube'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.5798
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1468 before and 0.0690 after correction.
The Ratio of minimum to maximum transmission is 0.7770.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_description       plate
_exptl_crystal_F_000             450
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.764
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     370
_refine_ls_number_reflns         4552
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.127
_refine_ls_R_factor_all          0.0943
_refine_ls_R_factor_gt           0.0800
_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/[\s^2^(Fo^2^)+(0.0573P)^2^+1.6795P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1738
_refine_ls_wR_factor_ref         0.1816
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3844
_reflns_number_total             4552
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5nj00425j2.cif
_cod_data_source_block           23srv215
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7063723.cif.
;
_cod_original_formula_sum        'C17 H24 N9 O4.50'
_cod_database_code               7063723
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.998
_shelx_estimated_absorpt_t_min   0.958
_computing_bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Restrained distances
 O4-C1SA
 1.46 with sigma of 0.005
 N3-H3A \\sim N3-H3B
 with sigma of 0.005
3. Uiso/Uaniso restraints and constraints
Uanis(C1SA) \\sim Ueq: with sigma of 0.003 and sigma for terminal atoms of 0.009
4. Others
 Fixed Sof: C1S(0.7) H1SA(0.7) H1SB(0.7) H1SC(0.7) C1SA(0.3) H1SD(0.3)
 H1SE(0.3) H1SF(0.3) O5(0.5) H5A(0.5) H5B(0.5)
5.a Riding coordinates:
 O4(H4A)
5.b Free rotating group:
 O5(H5A,H5B)
5.c Idealised Me refined as rotating group:
 C1S(H1SA,H1SB,H1SC), C1SA(H1SD,H1SE,H1SF)
;
_olex2_submission_special_instructions 'No special instructions were received'