Lenalidomide, an antineoplastic drug, and its hemihydrate
Ravikumar, Krishnan; Sridhar, Balasubramanian; Acta Crystallographica Section C 65 (2009) o502–o505; doi:10.1107/S0108270109033642

data_2017358
_publ_section_title
;
 Lenalidomide, an antineoplastic drug, and its hemihydrate
;
_journal_coeditor_code           SF3114
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o502
_journal_page_last               o505
_journal_paper_doi               10.1107/S0108270109033642
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C13 H13 N3 O3'
_chemical_formula_moiety         'C13 H13 N3 O3'
_chemical_formula_sum            'C13 H13 N3 O3'
_chemical_formula_weight         259.26
_chemical_name_common            Lenalidomide
_chemical_name_systematic
;
(<i>RS</i>)-3-(4-amino-1-oxoisoindolin-2-yl)piperidine-2,6-dione
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                75.7110(10)
_cell_angle_beta                 84.6600(10)
_cell_angle_gamma                86.0380(10)
_cell_formula_units_Z            2
_cell_length_a                   5.9983(5)
_cell_length_b                   8.9198(8)
_cell_length_c                   11.5785(10)
_cell_measurement_reflns_used    5070
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      28.05
_cell_measurement_theta_min      2.36
_cell_volume                     597.04(9)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2005)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0155
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_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_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            5703
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.82
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.195
_refine_ls_extinction_coef       0.069(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2092
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0393
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.0565P)^2^+0.1503P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1022
_refine_ls_wR_factor_ref         0.1037
_reflns_number_gt                1975
_reflns_number_total             2092
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            sf3114.cif
_cod_data_source_block           I
_cod_database_code               2017358
_cod_database_fobs_code          2017358