Methyl effect in azumamides provides insight into histone deacetylase inhibition by macrocycles.
Maolanon, Alex R.; Villadsen, Jesper S.; Christensen, Niels J.; Hoeck, Casper; Friis, Tina; Harris, Pernille; Gotfredsen, Charlotte H.; Fristrup, Peter; Olsen, Christian A.; Journal of medicinal chemistry 57 (2014) 9644–9657; doi:10.1021/jm501399d

data_1518236
_publ_section_title
;
 Methyl effect in azumamides provides insight into histone deacetylase
 inhibition by macrocycles.
;
_journal_issue                   22
_journal_name_full               'Journal of medicinal chemistry'
_journal_page_first              9644
_journal_page_last               9657
_journal_paper_doi               10.1021/jm501399d
_journal_volume                  57
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C13 H27 N O4 S'
_chemical_formula_sum            'C13 H27 N O4 S'
_chemical_formula_weight         293.41
_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_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2014-07-04
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.12 svn.r2899 for OlexSys, GUI svn.r4796)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.895(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.0994(17)
_cell_length_b                   22.475(6)
_cell_length_c                   11.962(4)
_cell_measurement_reflns_used    1454
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      18.904
_cell_measurement_theta_min      3.342
_cell_volume                     1638.9(8)
_computing_data_reduction        'SAINT v6.45A (Bruker, 2003)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_diffrn_ambient_temperature      120.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1133
_diffrn_reflns_av_unetI/netI     0.1730
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17843
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.231
_diffrn_reflns_theta_min         1.703
_exptl_absorpt_coefficient_mu    0.207
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.673074
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS v.2.10 (Bruker,2003) was used for absorption correction.
R(int) was 0.1012 before and 0.0547 after correction.
The Ratio of minimum to maximum transmission is 0.6731.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_density_diffrn    1.189
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.598
_refine_diff_density_rms         0.085
_refine_ls_abs_structure_details
;
 Flack x determined using 1429 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.09(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         7951
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.1670
_refine_ls_R_factor_gt           0.0828
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0671P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1511
_refine_ls_wR_factor_ref         0.1890
_reflns_Friedel_coverage         0.931
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.974
_reflns_number_gt                4406
_reflns_number_total             7951
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jm501399d_si_003.cif
_cod_data_source_block           cpd25
_cod_depositor_comments
'Adding full bibliography for 1518235--1518236.cif.'
_cod_original_cell_volume        1638.8(8)
_cod_database_code               1518236
_shelxl_version_number           2013-2
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All N(H) groups, All O(H) groups
2. Restrained distances
 N21-H21
 0.86 with sigma of 0.02
 N11-H11
 0.86 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C15(H15), C25(H25)
3.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B), C26(H26A,H26B), C27(H27A,
 H27B), C28(H28A,H28B)
3.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C111(H11A,H11B,
 H11C), C112(H11D,H11E,H11F), C113(H11G,H11H,H11I), C22(H22A,H22B,H22C),
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C211(H21A,H21B,H21C), C212(H21D,H21E,
 H21F), C213(H21G,H21H,H21I)
3.d Idealised tetrahedral OH refined as rotating group:
 O12(H12), O22(H22)
;
_shelx_res_checksum              49385
_shelx_hkl_checksum              71308
_olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2008)'