Axinellamines as broad-spectrum antibacterial agents: scalable synthesis and biology.
Rodriguez, Rodrigo A.; Barrios Steed, Danielle; Kawamata, Yu; Su, Shun; Smith, Peter A.; Steed, Tyler C.; Romesberg, Floyd E.; Baran, Phil S.; Journal of the American Chemical Society 136 (2014) 15403–15413; doi:10.1021/ja508632y

data_4122819
_publ_section_title
;
 Axinellamines as broad-spectrum antibacterial agents: scalable synthesis
 and biology.
;
_journal_issue                   43
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15403
_journal_page_last               15413
_journal_paper_doi               10.1021/ja508632y
_journal_volume                  136
_journal_year                    2014
_chemical_formula_moiety         'C7 H17 N O3'
_chemical_formula_sum            'C7 H17 N O3'
_chemical_formula_weight         163.21
_chemical_name_common            'RRVI N oxide diol'
_chemical_name_systematic        3-(N,N-diethylamine)-propan-1,2-diol-N-oxide
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-09-26
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_cell_angle_alpha                90
_cell_angle_beta                 95.341(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.6142(5)
_cell_length_b                   12.7026(8)
_cell_length_c                   12.0019(8)
_cell_measurement_reflns_used    2998
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.367
_cell_measurement_theta_min      2.340
_cell_volume                     852.20(11)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX II TXS'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         26.402
_diffrn_reflns_theta_min         2.340
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker TXS'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6499
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1524 before and 0.0322 after correction.
The Ratio of minimum to maximum transmission is 0.8719.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            Colorless
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    Colorless
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_method    'Not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     115
_refine_ls_number_reflns         1740
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0324
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0425P)^2^+0.3061P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0846
_refine_ls_wR_factor_ref         0.0872
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1515
_reflns_number_total             1740
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja508632y_si_005.cif
_cod_data_source_block           Baran313
_cod_depositor_comments
;
The following automatic conversions were performed:

'_diffrn_radiation_probe' value 'X-ray' changed to 'x-ray' according
to
/home/saulius/struct/COD-crude-data--automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_exptl_crystal_colour_lustre' value 'Clear' changed to
'clear' according to
/home/saulius/struct/COD-crude-data--automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2827 2014-09-09 07:05:25Z andrius 

 Adding full bibliography for 4122817--4122821.cif.
;
_cod_database_code               4122819
_shelxl_version_number           2013-3
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.969
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O1-H1
 0.9 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(O2A) = Uanis(O2)
4. Others
 Sof(H2B)=Sof(O2A)=Sof(H2AA)=1-FVAR(1)
 Sof(O2)=Sof(H2)=Sof(H2A)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C2(H2A), C2(H2B)
5.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C3(H3A,H3B), C4(H4A,H4B), C6(H6A,H6B)
5.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C7(H7A,H7B,H7C)
5.d Idealised tetrahedral OH refined as rotating group:
 O2A(H2AA)
;
_shelx_res_checksum              14257
_shelx_hkl_checksum              72349