Spontaneous single-crystal to single-crystal transition with self-healing cracks involving solvent exchange
Shen, Jie; Bai, Hongzhen; Zhou, Xinbo; Liu, Jiyong; Hu, Xiurong; Chu, Paul K.; Tang, Guping; CrystEngComm 21 (2019) 1102–; doi:10.1039/C8CE02110D

data_7239601
_publ_section_title
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 Spontaneous single-crystal to single-crystal transition with self-healing
 cracks involving solvent exchange
;
_journal_issue                   7
_journal_name_full               CrystEngComm
_journal_page_first              1102
_journal_paper_doi               10.1039/C8CE02110D
_journal_volume                  21
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C27 H37 N3 O7 S, C2 H6 O'
_chemical_formula_sum            'C29 H43 N3 O8 S'
_chemical_formula_weight         593.72
_chemical_name_common            'darunavir ethanol solvate'
_chemical_name_systematic
'(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl((2S,3R)-4-((4-amino-N-isobutylphenyl)sulfonamido)-3-hydroxy-1-phenylbutan-2-yl)carbamate ethanol solvate'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-08-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-08-24 deposited with the CCDC.
2019-02-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.9846(5)
_cell_length_b                   16.6017(10)
_cell_length_c                   19.0274(10)
_cell_measurement_reflns_used    26982
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      51.992
_cell_measurement_theta_min      6.382
_cell_volume                     3154.0(3)
_computing_cell_refinement       'PROCESS-AUTO  (Rigaku,2006)'
_computing_data_collection       'PROCESS-AUTO  (Rigaku,2006)'
_computing_data_reduction        'CrystalStructure (Rigaku,2007)'
_computing_molecular_graphics
'Ortep3 for windows (Farrugia,1997) and Diamond (Brandengurg & Putz, 2005)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  R-AXIS-RAPID
_diffrn_measurement_method       \w
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1089
_diffrn_reflns_av_unetI/netI     0.0931
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            26982
_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         25.996
_diffrn_reflns_theta_min         3.191
_diffrn_source                   'rotating anode'
_exptl_absorpt_coefficient_mu    0.154
_exptl_absorpt_correction_T_max  0.9758
_exptl_absorpt_correction_T_min  0.9313
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Higashi, T. (1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       chunk
_exptl_crystal_F_000             1272
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 1053 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     375
_refine_ls_number_reflns         6191
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.1451
_refine_ls_R_factor_gt           0.0923
_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^)+(0.0523P)^2^+1.4336P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1391
_refine_ls_wR_factor_ref         0.1592
_reflns_Friedel_coverage         0.779
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3911
_reflns_number_total             6191
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ce02110d2.cif
_cod_data_source_block           dl-ethy
_cod_database_code               7239601
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.976
_shelx_estimated_absorpt_t_min   0.931
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C28-C29
 1.54 with sigma of 0.002
3. Uiso/Uaniso restraints and constraints
Uanis(C28) \\sim Ueq, Uanis(C29) \\sim Ueq: with sigma of 0.0005 and sigma for
terminal atoms of 0.001
4.a Riding coordinates:
 N3(H3A,H3B)
4.b Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C7(H7), C10(H10), C19(H19)
4.c Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C6(H6A,H6B), C8(H8A,H8B), C9(H9A,H9B), C11(H11A,H11B), C18(H18A,
 H18B), C28(H28A,H28B)
4.d Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C15(H15), C16(H16), C17(H17), C23(H23), C24(H24),
 C26(H26), C27(H27), N2(H2A)
4.e Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C29(H29A,H29B,H29C)
4.f Idealised tetrahedral OH refined as rotating group:
 O3(H3C), O8(H8)
;
_olex2_submission_original_sample_id DLNW-C2H5OH
_olex2_submission_special_instructions 'No special instructions were received'