Enantioselective synthesis of adamantylalanine and carboranylalanine and their incorporation into the proteasome inhibitor bortezomib.
de Bruin, Gerjan; Mock, Elliot D.; Hoogendoorn, Sascha; van den Nieuwendijk, Adrianus M. C. H.; Mazurek, Jaroslaw; van der Marel, Gijsbert A.; Florea, Bogdan I.; Overkleeft, Herman S.; Chemical communications (Cambridge, England) 52 (2016) 4064–4067; doi:10.1039/c6cc01156j

data_7118764
_publ_section_title
;
 Enantioselective synthesis of adamantylalanine and carboranylalanine and
 their incorporation into the proteasome inhibitor bortezomib.
;
_journal_issue                   21
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              4064
_journal_page_last               4067
_journal_paper_doi               10.1039/c6cc01156j
_journal_volume                  52
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C9 H24 B10 N2 O S'
_chemical_formula_sum            'C9 H24 B10 N2 O S'
_chemical_formula_weight         316.46
_chemical_name_common
' (Ss)-(+)-N-[(R)-1-Cyano-2-(1?,2?-dicarba-closo-dodecaboranyl)ethyl]-tert-butylsulfinamide '
_chemical_name_systematic        '21 b (EDM345)'
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2015-12-14 deposited with the CCDC.
2016-02-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 115.831(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   26.2252(15)
_cell_length_b                   6.7734(3)
_cell_length_c                   11.5919(6)
_cell_measurement_reflns_used    6658
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      32.577
_cell_measurement_theta_min      0.998
_cell_volume                     1853.37(17)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Hooft, 1998)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'enCIFer (Allen et al., 2004)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  'KappaCCD, Bruker-AXS'
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_laue_measured_fraction_full 0.995
_diffrn_reflns_laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13344
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.601
_diffrn_reflns_theta_min         3.129
_exptl_absorpt_coefficient_mu    0.170
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.134
_exptl_crystal_description       Needle
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
;
 Flack x determined using 1942 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         6764
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0470
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0486P)^2^+0.2463P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1033
_refine_ls_wR_factor_ref         0.1099
_reflns_Friedel_coverage         0.866
_reflns_friedel_fraction_full    0.998
_reflns_friedel_fraction_max     0.997
_reflns_number_gt                5431
_reflns_number_total             6764
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc01156j2.cif
_cod_data_source_block           EDM345
_cod_depositor_comments
'Adding full bibliography for 7118764--7118765.cif.'
_cod_original_cell_volume        1853.38(17)
_cod_database_code               7118764
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              27032
_shelx_hkl_checksum              90108