How Cocrystallization Affects Solid-State Tautomerism: Stanozolol Case Study
Tilborg, Anaëlle; Springuel, Géraldine; Norberg, Bernadette; Wouters, Johan; Leyssens, Tom; Crystal Growth & Design 14 (2014) 3408–; doi:10.1021/cg500358h

data_4511300
_publ_section_title
;
 How Cocrystallization Affects Solid-State Tautomerism: Stanozolol Case
 Study
;
_journal_issue                   7
_journal_name_full               'Crystal Growth &amp; Design'
_journal_page_first              3408
_journal_paper_doi               10.1021/cg500358h
_journal_volume                  14
_journal_year                    2014
_chemical_absolute_configuration rm
_chemical_formula_moiety         '2(C21 H32 N2 O), C9 H10 O3, C2 H3 N'
_chemical_formula_sum            'C53 H77 N5 O5'
_chemical_formula_weight         864.20
_chemical_name_common            'Stanozolol / D-phenyllactic acid cocrystal'
_chemical_name_systematic
;
(R)-2-hydroxy-3-phenylpropanoic acid compound with 
acetonitrile and
(1S,10aS,12aS)-1,10a,12a-trimethyl-
1,2,3,3a,3b,4,5,5a,6,8,10,10a,10b,11,12,12a-hexadecahydrocyclopenta
[5,6]naphtho[1,2-f]indazol-1-ol (1:1:2)
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2014-03-03 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 97.989(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   58.6098(12)
_cell_length_b                   7.5624(2)
_cell_length_c                   10.7139(4)
_cell_measurement_reflns_used    9549
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.5350
_cell_measurement_theta_min      2.9910
_cell_volume                     4702.6(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 5.1856
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0975
_diffrn_reflns_av_sigmaI/netI    0.0634
_diffrn_reflns_limit_h_max       66
_diffrn_reflns_limit_h_min       -69
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            18654
_diffrn_reflns_theta_full        66.60
_diffrn_reflns_theta_max         66.60
_diffrn_reflns_theta_min         3.05
_exptl_absorpt_coefficient_mu    0.612
_exptl_absorpt_correction_T_max  0.9413
_exptl_absorpt_correction_T_min  0.896
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1880
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.089
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.7(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     559
_refine_ls_number_reflns         6280
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0960
_refine_ls_R_factor_gt           0.0837
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1652P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2139
_refine_ls_wR_factor_ref         0.2237
_reflns_number_gt                5357
_reflns_number_total             8282
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg500358h_si_006.cif
_cod_data_source_block           bn_tlgs3335
_cod_depositor_comments
'Adding full bibliography for 4511300--4511302.cif.'
_cod_original_sg_symbol_H-M      C2
_cod_database_code               4511300