# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
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data_d8v17156
_audit_block_doi                 10.5517/ccdc.csd.cc2dhzc8
_database_code_depnum_ccdc_archive 'CCDC 2219890'
loop_
_audit_author_name
_audit_author_address
'Qi Zhang'
;East China University of Science and Technology
China
;
_audit_update_record             
;
2022-11-15 deposited with the CCDC.	2025-03-26 downloaded from the CCDC.
;
_audit_creation_date             2017-06-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/8
_chemical_name_common            'Lenalidomide Dihydrate'
_chemical_name_systematic        
3-(4-Amino-1-oxoisoindolin-2-yl)piperidine-2,6-dione
_chemical_formula_moiety         'C13 H13 N3 O3, 2(H2 O)'
_chemical_formula_sum            'C13 H17 N3 O5'
_chemical_formula_weight         295.29
_chemical_melting_point          ?
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'
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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'

_cell_length_a                   13.4300(14)
_cell_length_b                   8.8535(10)
_cell_length_c                   11.7594(12)
_cell_angle_alpha                90
_cell_angle_beta                 99.231(6)
_cell_angle_gamma                90
_cell_volume                     1380.1(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2137
_cell_measurement_temperature    281(2)
_cell_measurement_theta_max      70.01
_cell_measurement_theta_min      3.33
_shelx_estimated_absorpt_T_max   0.873
_shelx_estimated_absorpt_T_min   0.821
_exptl_absorpt_coefficient_mu    0.933
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.5737
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1301 before and 0.0878 after correction. The Ratio of minimum to maximum transmission is 0.7616. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0808
_diffrn_reflns_av_unetI/netI     0.0615
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13400
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.195
_diffrn_reflns_theta_min         3.334
_diffrn_ambient_temperature      281.59
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1784
_reflns_number_total             2590
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       0.026(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/8 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2590
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1059
_refine_ls_R_factor_gt           0.0806
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1511P)²+0.4709P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2268
_refine_ls_wR_factor_ref         0.2677
_refine_special_details          ?
_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,H) groups
2.a Free rotating group:
 O5(H5A,H5B)
2.b Ternary CH refined with riding coordinates:
 C9(H9)
2.c Secondary CH2 refined with riding coordinates:
 C1(H1C,H1D), C11(H11A,H11B), C12(H12A,H12B)
2.d Aromatic/amide H refined with riding coordinates:
 N3(H3), C4(H4), C5(H5), C6(H6)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.6853(2) 0.4405(3) 0.9440(2) 0.0769(8) Uani 1 1 d . . . . .
O2 O 0.7995(3) 0.4745(4) 0.6636(3) 0.1051(12) Uani 1 1 d . . . . .
O3 O 0.5302(2) 0.6393(3) 0.4216(2) 0.0803(8) Uani 1 1 d . . . . .
N1 N 1.0480(3) 0.8359(4) 1.0137(4) 0.0813(10) Uani 1 1 d . . . . .
H1A H 1.111(3) 0.845(4) 1.053(4) 0.073(11) Uiso 1 1 d . . . . .
H1B H 1.031(4) 0.865(5) 0.941(5) 0.104(18) Uiso 1 1 d . . . . .
N2 N 0.7564(2) 0.6336(3) 0.8529(3) 0.0685(8) Uani 1 1 d . . . . .
N3 N 0.6656(2) 0.5632(4) 0.5439(3) 0.0688(8) Uani 1 1 d . . . . .
H3 H 0.6840 0.5117 0.4888 0.083 Uiso 1 1 calc R . . . .
C1 C 0.8460(3) 0.7306(4) 0.8719(3) 0.0665(9) Uani 1 1 d . . . . .
H1C H 0.8276 0.8364 0.8735 0.080 Uiso 1 1 calc R . . . .
H1D H 0.8879 0.7150 0.8131 0.080 Uiso 1 1 calc R . . . .
C2 C 0.8979(3) 0.6785(4) 0.9873(3) 0.0623(9) Uani 1 1 d . . . . .
C3 C 0.9895(3) 0.7222(4) 1.0505(3) 0.0644(9) Uani 1 1 d . . . . .
C4 C 1.0217(3) 0.6455(4) 1.1539(3) 0.0685(9) Uani 1 1 d . . . . .
H4 H 1.0830 0.6722 1.1981 0.082 Uiso 1 1 calc R . . . .
C5 C 0.9654(3) 0.5311(4) 1.1927(3) 0.0705(10) Uani 1 1 d . . . . .
H5 H 0.9895 0.4831 1.2619 0.085 Uiso 1 1 calc R . . . .
C6 C 0.8743(3) 0.4873(4) 1.1305(3) 0.0676(9) Uani 1 1 d . . . . .
H6 H 0.8360 0.4107 1.1561 0.081 Uiso 1 1 calc R . . . .
C7 C 0.8425(3) 0.5630(4) 1.0276(3) 0.0608(8) Uani 1 1 d . . . . .
C8 C 0.7528(3) 0.5357(4) 0.9411(3) 0.0648(9) Uani 1 1 d . . . . .
C9 C 0.6830(3) 0.6307(4) 0.7482(3) 0.0689(10) Uani 1 1 d . . . . .
H9 H 0.6251 0.5724 0.7652 0.083 Uiso 1 1 calc R . . . .
C10 C 0.7238(3) 0.5481(4) 0.6513(3) 0.0726(10) Uani 1 1 d . . . . .
C11 C 0.6433(3) 0.7836(4) 0.7056(3) 0.0712(10) Uani 1 1 d . . . . .
H11A H 0.6965 0.8418 0.6794 0.085 Uiso 1 1 calc R . . . .
H11B H 0.6198 0.8388 0.7675 0.085 Uiso 1 1 calc R . . . .
C12 C 0.5564(3) 0.7595(5) 0.6065(3) 0.0763(11) Uani 1 1 d . . . . .
H12A H 0.4986 0.7209 0.6374 0.092 Uiso 1 1 calc R . . . .
H12B H 0.5375 0.8562 0.5707 0.092 Uiso 1 1 calc R . . . .
C13 C 0.5811(3) 0.6522(4) 0.5161(3) 0.0661(9) Uani 1 1 d . . . . .
O4 O 0.3779(3) 0.8487(5) 0.3470(3) 0.1062(13) Uani 1 1 d . . . . .
H4A H 0.357(3) 0.880(5) 0.407(4) 0.079(13) Uiso 1 1 d . . . . .
H4B H 0.428(5) 0.762(7) 0.369(5) 0.13(2) Uiso 1 1 d . . . . .
O5 O 0.2776(2) 0.8598(3) 0.1256(3) 0.0802(8) Uani 1 1 d . . . . .
H5A H 0.2868 0.7733 0.0977 0.120 Uiso 1 1 d G . . . .
H5B H 0.3092 0.8651 0.1941 0.120 Uiso 1 1 d G . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C8 1.243(4) . ?
O2 C10 1.197(5) . ?
O3 C13 1.213(4) . ?
N1 H1A 0.90(4) . ?
N1 H1B 0.89(5) . ?
N1 C3 1.389(5) . ?
N2 C1 1.465(4) . ?
N2 C8 1.358(5) . ?
N2 C9 1.449(5) . ?
N3 H3 0.8600 . ?
N3 C10 1.381(4) . ?
N3 C13 1.377(4) . ?
C1 H1C 0.9700 . ?
C1 H1D 0.9700 . ?
C1 C2 1.496(5) . ?
C2 C3 1.386(5) . ?
C2 C7 1.392(5) . ?
C3 C4 1.399(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.384(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.376(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.389(5) . ?
C7 C8 1.467(5) . ?
C9 H9 0.9800 . ?
C9 C10 1.527(6) . ?
C9 C11 1.511(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.527(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.502(5) . ?
O4 H4A 0.85(5) . ?
O4 H4B 1.02(7) . ?
O5 H5A 0.8502 . ?
O5 H5B 0.8500 . ?

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
H1A N1 H1B 123(4) . . ?
C3 N1 H1A 116(3) . . ?
C3 N1 H1B 116(3) . . ?
C8 N2 C1 112.7(3) . . ?
C8 N2 C9 122.3(3) . . ?
C9 N2 C1 124.8(3) . . ?
C10 N3 H3 116.7 . . ?
C13 N3 H3 116.7 . . ?
C13 N3 C10 126.6(3) . . ?
N2 C1 H1C 111.3 . . ?
N2 C1 H1D 111.3 . . ?
N2 C1 C2 102.1(3) . . ?
H1C C1 H1D 109.2 . . ?
C2 C1 H1C 111.3 . . ?
C2 C1 H1D 111.3 . . ?
C3 C2 C1 130.2(3) . . ?
C3 C2 C7 119.9(3) . . ?
C7 C2 C1 109.8(3) . . ?
N1 C3 C4 120.7(3) . . ?
C2 C3 N1 122.2(4) . . ?
C2 C3 C4 117.1(3) . . ?
C3 C4 H4 119.0 . . ?
C5 C4 C3 122.1(3) . . ?
C5 C4 H4 119.0 . . ?
C4 C5 H5 119.4 . . ?
C6 C5 C4 121.2(3) . . ?
C6 C5 H5 119.4 . . ?
C5 C6 H6 121.6 . . ?
C5 C6 C7 116.7(4) . . ?
C7 C6 H6 121.6 . . ?
C2 C7 C8 108.0(3) . . ?
C6 C7 C2 123.0(3) . . ?
C6 C7 C8 128.9(3) . . ?
O1 C8 N2 124.7(3) . . ?
O1 C8 C7 127.9(3) . . ?
N2 C8 C7 107.4(3) . . ?
N2 C9 H9 106.9 . . ?
N2 C9 C10 111.4(3) . . ?
N2 C9 C11 114.9(3) . . ?
C10 C9 H9 106.9 . . ?
C11 C9 H9 106.9 . . ?
C11 C9 C10 109.4(3) . . ?
O2 C10 N3 120.5(4) . . ?
O2 C10 C9 124.8(3) . . ?
N3 C10 C9 114.7(3) . . ?
C9 C11 H11A 110.0 . . ?
C9 C11 H11B 110.0 . . ?
C9 C11 C12 108.3(3) . . ?
H11A C11 H11B 108.4 . . ?
C12 C11 H11A 110.0 . . ?
C12 C11 H11B 110.0 . . ?
C11 C12 H12A 108.8 . . ?
C11 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
C13 C12 C11 113.6(3) . . ?
C13 C12 H12A 108.8 . . ?
C13 C12 H12B 108.8 . . ?
O3 C13 N3 119.1(3) . . ?
O3 C13 C12 123.5(3) . . ?
N3 C13 C12 117.4(3) . . ?
H4A O4 H4B 109(5) . . ?
H5A O5 H5B 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3 O5 0.86 2.03 2.878(4) 170.4 2_645
O4 H4A O1 0.85(5) 2.00(5) 2.844(5) 175(4) 2_656
O4 H4B O3 1.02(7) 1.79(7) 2.795(4) 168(5) .
O5 H5A O1 0.85 2.01 2.849(4) 171.6 3_666
O5 H5B O4 0.85 1.89 2.735(4) 172.4 .

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
