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_1518235
_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         'C15 H31 N O4 S, H2 O'
_chemical_formula_sum            'C15 H33 N O5 S'
_chemical_formula_weight         339.48
_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
_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                 102.833(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.9092(13)
_cell_length_b                   6.1043(5)
_cell_length_c                   17.9815(13)
_cell_measurement_reflns_used    3095
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      25.418
_cell_measurement_theta_min      2.333
_cell_volume                     1916.7(3)
_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(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.994
_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  0.0414
_diffrn_reflns_av_unetI/netI     0.0678
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            11996
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.340
_diffrn_reflns_theta_min         2.323
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.189
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.838952
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS v.2.10 (Bruker,2003) was used for absorption correction.
R(int) was 0.0698 before and 0.0344 after correction.
The Ratio of minimum to maximum transmission is 0.8390.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.176
_exptl_crystal_description       needle
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.532
_refine_diff_density_min         -0.561
_refine_diff_density_rms         0.090
_refine_ls_abs_structure_details
;
 Flack x determined using 1332 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.08(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.186
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         4659
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.186
_refine_ls_R_factor_all          0.0784
_refine_ls_R_factor_gt           0.0479
_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^)+3.7854P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0760
_refine_ls_wR_factor_ref         0.1118
_reflns_Friedel_coverage         0.793
_reflns_Friedel_fraction_full    0.948
_reflns_Friedel_fraction_max     0.947
_reflns_number_gt                3636
_reflns_number_total             4659
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jm501399d_si_002.cif
_cod_data_source_block           cpd18
_cod_depositor_comments
'Adding full bibliography for 1518235--1518236.cif.'
_cod_database_code               1518235
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O1(H1A,H1B)
2.b Ternary CH refined with riding coordinates:
 C8(H8)
2.c Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C16(H16A,H16B)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C12(H12A,H12B,H12C), C14(H14A,H14B,H14C), C15(H15A,H15B,
 H15C), C17(H17A,H17B,H17C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,
 H21B,H21C)
2.e Idealised tetrahedral OH refined as rotating group:
 O5(H5)
;
_shelx_res_checksum              37773
_shelx_hkl_checksum              41385
_olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2008)'