Understanding the formation of apremilast cocrystals
Dudek, Marta K.; Wielgus, Ewelina; Paluch, Piotr; Śniechowska, Justyna; Kostrzewa, Maciej; Day, Graeme M.; Bujacz, Grzegorz D.; Potrzebowski, Marek J.; Acta Crystallographica Section B 75 (2019) –; doi:10.1107/S205252061900917X

data_2108471
_publ_section_title
;
 Understanding the formation of apremilast cocrystals
;
_journal_coeditor_code           XK5057SUP1
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S205252061900917X
_journal_volume                  75
_journal_year                    2019
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C22 H24 N2 O7 S'
_chemical_formula_sum            'C22 H24 N2 O7 S'
_chemical_formula_weight         460.49
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2019-05-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 97.9370(14)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.71353(13)
_cell_length_b                   29.4960(6)
_cell_length_c                   17.6717(2)
_cell_measurement_reflns_used    14995
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      74.2430
_cell_measurement_theta_min      2.8960
_cell_volume                     4498.37(13)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 4.1685
_diffrn_detector_type            TitanS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details
;
  1 omega  -16.00   28.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.7274   37.0000 -120.0000 44

  2 omega  -43.00    3.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.7274   37.0000   60.0000 46

  3 omega -112.00  -19.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.7274  -37.0000  -90.0000 93

  4 omega   51.00   96.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       43.7274 -125.0000 -180.0000 45

  5 omega   49.00   97.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0840  -45.0000  -60.0000 48

  6 omega   70.00  171.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0840   15.0000    0.0000 101

  7 omega   91.00  118.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0840 -125.0000 -150.0000 27

  8 omega   39.00  103.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0840  -94.0000  -30.0000 64

  9 omega   37.00   90.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0840  -45.0000   90.0000 53

 10 omega   34.00   90.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0840  -30.0000   30.0000 56

 11 omega   23.00  107.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0840  -94.0000 -120.0000 84

 12 omega  112.00  163.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7090   30.0000    0.0000 51

 13 omega -118.00  -73.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.9774 -125.0000 -180.0000 45

 14 omega -116.00  -20.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.9774  -37.0000 -180.0000 96

 15 omega -114.00  -18.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.9774  -57.0000   90.0000 96

 16 omega   80.00  177.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7090   61.0000   30.0000 97

 17 omega   80.00  178.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7090   30.0000 -150.0000 98

 18 omega   81.00  177.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7090   45.0000  150.0000 96

 19 omega   24.00  109.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7090  -94.0000   90.0000 85

 20 omega   81.00  177.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7090   45.0000   90.0000 96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, TitanS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0411311000
_diffrn_orient_matrix_UB_12      0.0181677000
_diffrn_orient_matrix_UB_13      0.0820167000
_diffrn_orient_matrix_UB_21      0.0138543000
_diffrn_orient_matrix_UB_22      -0.0489541000
_diffrn_orient_matrix_UB_23      0.0304821000
_diffrn_orient_matrix_UB_31      0.1732277000
_diffrn_orient_matrix_UB_32      -0.0004148000
_diffrn_orient_matrix_UB_33      -0.0094029000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_av_unetI/netI     0.0402
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            43359
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.372
_diffrn_reflns_theta_min         2.524
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.678
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81707
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_description
;
;
_exptl_crystal_F_000             1936
_exptl_crystal_size_max          0.314
_exptl_crystal_size_mid          0.058
_exptl_crystal_size_min          0.024
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 5723 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.004(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1169
_refine_ls_number_reflns         17606
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0448
_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^)+(0.0529P)^2^+0.3705P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1097
_refine_ls_wR_factor_ref         0.1187
_reflns_Friedel_coverage         0.887
_reflns_Friedel_fraction_full    0.962
_reflns_Friedel_fraction_max     0.909
_reflns_number_gt                14660
_reflns_number_total             17606
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            xk5057sup1.cif
_cod_data_source_block           apre1
_cod_original_cell_volume        4498.36(12)
_cod_database_code               2108471
_cod_database_fobs_code          2108471
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.99
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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
2.a Riding coordinates:
 N2B(H2B)
2.b Ternary CH refined with riding coordinates:
 C11A(H11A), C11B(H11B), C11C(H11C), C11D(H11D)
2.c Secondary CH2 refined with riding coordinates:
 C12A(H12A,H12B), C20A(H20A,H20B), C12B(H12C,H12D), C20B(H20C,H20D), C12C(H12E,
 H12F), C20C(H20E,H20F), C12D(H12G,H12H), C20D(H20G,H20H)
2.d Aromatic/amide H refined with riding coordinates:
 N2A(H2A), C2A(H2AA), C3A(H3A), C4A(H4A), C15A(H15A), C16A(H16A), C19A(H19A),
 C2B(H2BA), C3B(H3B), C4B(H4B), C15B(H15B), C16B(H16B), C19B(H19B), N2C(H2C),
 C2C(H2CA), C3C(H3C), C4C(H4C), C15C(H15C), C18C(H18C), C19C(H19C), N2D(H2D),
 C2D(H2DA), C3D(H3D), C4D(H4D), C15D(H15D), C18D(H18D), C19D(H19D)
2.e Idealised Me refined as rotating group:
 C10A(H10A,H10B,H10C), C13A(H13A,H13B,H13C), C21A(H21A,H21B,H21C), C22A(H22A,
 H22B,H22C), C10B(H10D,H10E,H10F), C13B(H13D,H13E,H13F), C21B(H21D,H21E,H21F),
 C22B(H22D,H22E,H22F), C10C(H10G,H10H,H10I), C13C(H13G,H13H,H13I), C21C(H21G,
 H21H,H21I), C22C(H22G,H22H,H22I), C10D(H10J,H10K,H10L), C13D(H13J,H13K,H13L),
 C21D(H21J,H21K,H21L), C22D(H22J,H22K,H22L)
;
_shelx_res_checksum              92442
_shelx_hkl_checksum              24377
_olex2_date_sample_data_collection 2018-11-13
_olex2_submission_special_instructions 'No special instructions were received'