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_2108472
_publ_section_title
;
 Understanding the formation of apremilast cocrystals
;
_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, 0.5(C6 H6 O2), 0.5(H2 O)'
_chemical_formula_sum            'C25 H28 N2 O8.5 S'
_chemical_formula_weight         524.55
_space_group_crystal_system      tetragonal
_space_group_IT_number           92
_space_group_name_Hall           'P 4abw 2nw'
_space_group_name_H-M_alt        'P 41 21 2'
_symmetry_space_group_name_Hall  'P 4abw 2nw'
_symmetry_space_group_name_H-M   'P 41 21 2'
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.89179(7)
_cell_length_b                   12.89179(7)
_cell_length_c                   29.5087(3)
_cell_measurement_reflns_used    29116
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      74.5720
_cell_measurement_theta_min      3.3610
_cell_volume                     4904.29(6)
_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_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_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 0.998
_diffrn_measurement_details
;
  1 omega  -75.00   31.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.4774   77.0000   90.0000 106

  2 omega   12.00  118.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       43.4774   77.0000  -60.0000 106

  3 omega   74.00  178.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      105.4590   77.0000    0.0000 104

  4 omega   74.00  178.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      105.4590   77.0000 -150.0000 104

  5 omega   74.00  178.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      105.4590   77.0000  -30.0000 104

  6 omega   74.00  178.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      105.4590   77.0000   90.0000 104

  7 omega   12.00  118.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       43.4774   77.0000  150.0000 106

  8 omega   18.00  113.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       43.4774   57.0000   60.0000 95

  9 omega   32.00  122.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      105.4590 -125.0000 -180.0000 90

 10 omega   79.00  175.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      105.4590   61.0000  -90.0000 96

 11 omega   79.00  122.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      105.4590   61.0000   60.0000 43

 12 omega   74.00  178.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      105.4590   77.0000  150.0000 104
;
_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      -0.0474537000
_diffrn_orient_matrix_UB_12      0.0480241000
_diffrn_orient_matrix_UB_13      0.0430777000
_diffrn_orient_matrix_UB_21      -0.1073412000
_diffrn_orient_matrix_UB_22      -0.0422529000
_diffrn_orient_matrix_UB_23      -0.0136135000
_diffrn_orient_matrix_UB_31      0.0224081000
_diffrn_orient_matrix_UB_32      -0.1009248000
_diffrn_orient_matrix_UB_33      0.0261888000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            38451
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.776
_diffrn_reflns_theta_min         3.742
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.658
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.25040
_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    1.421
_exptl_crystal_description
;
;
_exptl_crystal_F_000             2208
_exptl_crystal_size_max          0.4818
_exptl_crystal_size_mid          0.3026
_exptl_crystal_size_min          0.1635
_refine_diff_density_max         0.902
_refine_diff_density_min         -0.632
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details
;
 Flack x determined using 1998 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.001(6)
_refine_ls_extinction_coef       0.00080(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     360
_refine_ls_number_reflns         5001
_refine_ls_number_restraints     96
_refine_ls_restrained_S_all      1.266
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0471
_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^)+(0.0752P)^2^+4.1347P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1321
_refine_ls_wR_factor_ref         0.1322
_reflns_Friedel_coverage         0.700
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                4965
_reflns_number_total             5001
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            xk5057sup1.cif
_cod_data_source_block           cocr1l
_cod_original_cell_volume        4904.29(7)
_cod_original_formula_sum        'C25 H28 N2 O8.50 S'
_cod_database_code               2108472
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, H53 of O53, All C(H,H) groups, All N(H) groups, All O(H,H)
  groups
 At 1.5 times of:
  All C(H,H,H) groups, H51 of O51
2. Restrained distances
 C51-O51 = C53-O53
 1.36 with sigma of 0.01
 O51-C52 = O51-C56 = O53-C52 = O53-C54
 1.93 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C51 \\sim C52 \\sim C53 \\sim C54 \\sim C55 \\sim C56: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02
O51 \\sim O53 \\sim O1W: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02
Uanis(C51) \\sim Ueq, Uanis(C52) \\sim Ueq, Uanis(C53) \\sim Ueq, Uanis(C54)
\\sim Ueq, Uanis(C55) \\sim Ueq, Uanis(C56) \\sim Ueq, Uanis(O51) \\sim Ueq,
Uanis(O53) \\sim Ueq, Uanis(O1W) \\sim Ueq: with sigma of 0.002 and sigma for
terminal atoms of 0.005
4. Others
 Fixed Sof: C51(0.5) C52(0.5) H52(0.5) C53(0.5) C54(0.5) H54(0.5) C55(0.5)
 H55(0.5) C56(0.5) H56(0.5) O51(0.5) H51(0.5) O53(0.5) H53(0.5) H1WA(0.5)
 H1WB(0.5)
5.a Riding coordinates:
 O1W(H1WA,H1WB)
5.b Ternary CH refined with riding coordinates:
 C11(H11)
5.c Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C20(H20A,H20B)
5.d Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), N2(H2A), C15(H15), C18(H18), C19(H19), C52(H52),
 C54(H54), C55(H55), C56(H56)
5.e Fitted hexagon refined as free rotating group:
 C51(C52,C53,C54,C55,C56)
5.f Tetrahedral OH refined with riding coordinates:
 O53(H53)
5.g Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C13(H13A,H13B,H13C), C21(H21A,H21B,H21C), C22(H22A,H22B,
 H22C)
5.h Idealised tetrahedral OH refined as rotating group:
 O51(H51)
;
_shelx_res_checksum              18319
_shelx_hkl_checksum              65899
_olex2_date_sample_data_collection 2018-05-15
_olex2_submission_special_instructions 'No special instructions were received'
_cod_database_fobs_code 2108472