Piezoactive amino acid derivatives containing fragments of planar-chiral ortho-carboranes
Gruzdev, Dmitry A.; Nuraeva, Alla S.; Slepukhin, Pavel A.; Levit, Galina L.; Zelenovskiy, Pavel S.; Shur, Vladimir Ya.; Krasnov, Victor P.; Journal of Materials Chemistry C 6 (2018) 8638–; doi:10.1039/C8TC02266F

data_7237354
_publ_section_title
;
 Piezoactive amino acid derivatives containing fragments of planar-chiral
 ortho-carboranes
;
_journal_issue                   32
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              8638
_journal_paper_doi               10.1039/C8TC02266F
_journal_volume                  6
_journal_year                    2018
_chemical_absolute_configuration (S,S)
_chemical_formula_moiety         'C19 H34 B10 N2 O4'
_chemical_formula_sum            'C19 H34 B10 N2 O4'
_chemical_formula_weight         462.58
_chemical_melting_point          440.0(10)
_chemical_name_common
;
(S,S)-tert-Butyl N-(3-acetamido-1,2-dicarba-closo-dodecaboran-1-yl)acetylphenylalaninate
;
_chemical_name_systematic
; 
(S,S)-tert-Butyl N-(3-acetamido-1,2-dicarba-closo-dodecaboran-1-yl)acetylphenylalaninate
;
_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_Int_Tables_number      4
_atom_sites_solution_primary     iterative
_audit_creation_method           SHELXL-97
_audit_update_record
;
2018-04-23 deposited with the CCDC.
2018-07-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.99(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.565(11)
_cell_length_b                   17.879(6)
_cell_length_c                   13.048(5)
_cell_measurement_reflns_used    2963
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      65.5101
_cell_measurement_theta_min      3.6660
_cell_volume                     2698(3)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.9663
_diffrn_measured_fraction_theta_max 0.9634
_diffrn_measurement_device_type  'Xcalibur 3'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0775
_diffrn_reflns_av_unetI/netI     0.0647
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            25360
_diffrn_reflns_theta_full        67.7449
_diffrn_reflns_theta_max         67.74
_diffrn_reflns_theta_min         3.68
_exptl_absorpt_coefficient_mu    0.550
_exptl_absorpt_correction_T_max  1.45908
_exptl_absorpt_correction_T_min  0.58421
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET)
(compiled Mar 23 2006,23:39:28)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.1386
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             975.8240
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: MeOH-H2O'
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.1707
_refine_diff_density_min         -0.2428
_refine_diff_density_rms         0.0475
_refine_ls_d_res_high            0.8330
_refine_ls_d_res_low             12.0115
_refine_ls_goodness_of_fit_ref   0.9817
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    132
_refine_ls_number_parameters     723
_refine_ls_number_reflns         4870
_refine_ls_number_restraints     121
_refine_ls_restrained_S_all      0.9678
_refine_ls_R_factor_all          0.0972
_refine_ls_R_factor_gt           0.0501
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0420P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1006
_refine_ls_wR_factor_ref         0.1094
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              13
_reflns_limit_h_min              -14
_reflns_limit_k_max              21
_reflns_limit_k_min              0
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                2302
_reflns_number_total             4870
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c8tc02266f2.cif
_cod_data_source_block           dc1_CCDC6
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '439-441 K' was changed to
'440.0(10)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_Hall     ' P 2yb'
_cod_database_code               7237354
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, 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. Restrained distances
 C1B-O4B
 1.3 with sigma of 0.02
 C1-O4
 1.3 with sigma of 0.02
 C1A-O4A
 1.3 with sigma of 0.02
 C1C-O4C
 1.3 with sigma of 0.02
 C1A-O2A
 1.2 with sigma of 0.02
 C1C-O2C
 1.2 with sigma of 0.02
 C16A-C17A
 1.5 with sigma of 0.02
 C16A-C18A
 1.5 with sigma of 0.02
 C16A-C19A
 1.5 with sigma of 0.02
 C16A-C17C
 1.5 with sigma of 0.02
 C16A-C18C
 1.5 with sigma of 0.02
 C16A-C19C
 1.5 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C1) \\sim Ueq, Uanis(C1A) \\sim Ueq, Uanis(C1B) \\sim Ueq, Uanis(C1C)
\\sim Ueq, Uanis(O2) \\sim Ueq, Uanis(O2A) \\sim Ueq, Uanis(O2B) \\sim Ueq,
Uanis(O2C) \\sim Ueq, Uanis(O4) \\sim Ueq, Uanis(O4A) \\sim Ueq, Uanis(O4B)
\\sim Ueq, Uanis(O4C) \\sim Ueq: with sigma of 0.01 and sigma for terminal
atoms of 0.02
Uanis(C17A) \\sim Ueq, Uanis(C18A) \\sim Ueq, Uanis(C19A) \\sim Ueq,
Uanis(C17C) \\sim Ueq, Uanis(C18C) \\sim Ueq, Uanis(C19C) \\sim Ueq: with sigma
of 0.02 and sigma for terminal atoms of 0.04
4. Others
 Fixed Sof: O2(0.5) O4(0.5) C1(0.5) C1A(0.6) O2A(0.6) O4A(0.6) C17A(0.6)
 H17D(0.6) H17E(0.6) H17F(0.6) C18A(0.6) H18D(0.6) H18E(0.6) H18F(0.6)
 C19A(0.6) H19D(0.6) H19E(0.6) H19F(0.6) C1B(0.5) O2B(0.5) O4B(0.5) C1C(0.4)
 O2C(0.4) O4C(0.4) C19C(0.4) H19G(0.4) H19H(0.4) H19I(0.4) C17C(0.4) H17G(0.4)
 H17H(0.4) H17I(0.4) C18C(0.4) H18G(0.4) H18H(0.4) H18I(0.4) H2ad(0.5)
 H2be(0.5) H2Aa(0.6) H2Ab(0.4) H17a(0.6) H17b(0.6) H17c(0.6) H18a(0.6)
 H18b(0.6) H18c(0.6) H19a(0.6) H19b(0.6) H19c(0.6) H19d(0.4) H19e(0.4)
 H19f(0.4) H17d(0.4) H17e(0.4) H17f(0.4) H18d(0.4) H18e(0.4) H18f(0.4)
5.a Ternary CH refined with riding coordinates:
 C2(H2ad), C2(H2be), C2A(H2Aa), C2A(H2Ab)
5.b Secondary CH2 refined with riding coordinates:
 C3(H3b,H3c), C11(H11c,H11d), C3A(H3Aa,H3Ab), C11A(H11a,H11b)
5.c Aromatic/amide H refined with riding coordinates:
 C9A(H9Aa), C8A(H8Aa), C7A(H7Aa), C6A(H6Aa), C5A(H5Aa), C9(H9b), C8(H8b),
 C7(H7b), C6(H6b), C5(H5b), N1A(H1A), N2(H2), N1(H1b), N2A(H2A)
5.d Idealised Me refined as rotating group:
 C15(H15d,H15e,H15f), C17(H17g,H17h,H17i), C18(H18g,H18h,H18i), C19(H19g,H19h,
 H19i), C15A(H15a,H15b,H15c), C17A(H17a,H17b,H17c), C18A(H18a,H18b,H18c),
 C19A(H19a,H19b,H19c), C19C(H19d,H19e,H19f), C17C(H17d,H17e,H17f), C18C(H18d,
 H18e,H18f)
5.e Boron cage BH refined with riding coordinates:
 B1(H1), B2(H2b), B3(H3), B4(H4), B5(H5), B6(H6), B7(H7), B8(H8), B9(H9),
 C13(H13), B1A(H1Aa), B2A(H2Ac), B3A(H3A), B4A(H4A), B5A(H5A), B6A(H6A),
 B7A(H7A), B8A(H8A), B9A(H9A), C13A(H13A)
;
_olex2_submission_special_instructions 'No special instructions were received'