Synthesis, physicochemical properties and antimicrobial activity of mono-/dinitroxyl amides.
Kavala, Miroslav; Brezová, Vlasta; Svorc, Lubomír; Vihonská, Zuzana; Olejníková, Petra; Moncol, Ján; Kožíšek, Jozef; Herich, Peter; Szolcsányi, Peter; Organic & biomolecular chemistry 12 (2014) 4491–4502; doi:10.1039/c4ob00302k

data_7153882
_publ_section_title
;
 Synthesis, physicochemical properties and antimicrobial activity of
 mono-/dinitroxyl amides.
;
_journal_issue                   25
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4491
_journal_page_last               4502
_journal_paper_doi               10.1039/c4ob00302k
_journal_volume                  12
_journal_year                    2014
_chemical_formula_moiety         'C14 H27 N2 O2'
_chemical_formula_sum            'C14 H27 N2 O2'
_chemical_formula_weight         255.38
_chemical_name_systematic
;
N-(1-Oxo-2,2,6,6-tetramethylpiperidin-4-yl)-pivalamide
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_primary     direct
_audit_creation_date             2013-07-27
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.7026(4)
_cell_length_b                   9.9471(3)
_cell_length_c                   28.8577(12)
_cell_measurement_reflns_used    4836
_cell_measurement_temperature    293
_cell_measurement_theta_max      26.0050
_cell_measurement_theta_min      3.4020
_cell_volume                     3359.2(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al., 2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al., 2009)
;
_computing_structure_refinement
;
OLEX2.REFINE (Dolomanov et al., 2009)
;
_computing_structure_solution
;
OLEX2.SOLVE (Dolomanov et al., 2009)
;
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean 8.4353
_diffrn_measured_fraction_theta_full 0.9967
_diffrn_measured_fraction_theta_max 0.9969
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0115686000
_diffrn_orient_matrix_UB_12      -0.0687923000
_diffrn_orient_matrix_UB_13      -0.0044953000
_diffrn_orient_matrix_UB_21      -0.0082108000
_diffrn_orient_matrix_UB_22      -0.0149771000
_diffrn_orient_matrix_UB_23      0.0237888000
_diffrn_orient_matrix_UB_31      -0.0589359000
_diffrn_orient_matrix_UB_32      -0.0113650000
_diffrn_orient_matrix_UB_33      -0.0042081000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0181
_diffrn_reflns_av_unetI/netI     0.0127
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            15894
_diffrn_reflns_theta_full        26.0000
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.04
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.954
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            'orange '
_exptl_crystal_density_diffrn    1.0099
_exptl_crystal_description       plate
_exptl_crystal_F_000             1128.4824
_exptl_crystal_size_max          0.951
_exptl_crystal_size_mid          0.593
_exptl_crystal_size_min          0.285
_refine_diff_density_max         0.2151
_refine_diff_density_min         -0.1593
_refine_diff_density_rms         0.0340
_refine_ls_d_res_high            0.8002
_refine_ls_d_res_low             6.7098
_refine_ls_goodness_of_fit_ref   1.0712
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    65
_refine_ls_number_parameters     184
_refine_ls_number_reflns         3417
_refine_ls_number_restraints     27
_refine_ls_restrained_S_all      1.0668
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0507
_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^)+(0.0731P)^2^+0.5117P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1554
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              14
_reflns_limit_h_min              0
_reflns_limit_k_max              12
_reflns_limit_k_min              0
_reflns_limit_l_max              36
_reflns_limit_l_min              0
_reflns_number_gt                2518
_reflns_number_total             3417
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c4ob00302k2.cif
_cod_data_source_block           CCDC-953446
_cod_database_code               7153882
_chemical_oxdiff_formula         'C20 H32 N3 O3 F3'
_chemical_oxdiff_usercomment     '0.8 mm 2 kW'
_reflns_odcompleteness_completeness 99.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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
2. Restrained distances
 C11-C12A = C11-C12B = C11-C12C
 1.54 with sigma of 0.01
 C11-C13A = C11-C13B = C11-C13C
 1.54 with sigma of 0.01
 C11-C14A = C11-C14B = C11-C14C
 1.54 with sigma of 0.01
 C10-C12A \\sim C10-C12B \\sim C10-C12C
 with sigma of 0.02
 C10-C13A \\sim C10-C13B \\sim C10-C13C
 with sigma of 0.02
 C10-C14A \\sim C10-C14B \\sim C10-C14C
 with sigma of 0.02
 C12A-C13A \\sim C12A-C14A \\sim C13A-C14A
 with sigma of 0.02
 C12B-C13B \\sim C12B-C14B \\sim C13B-C14B
 with sigma of 0.02
 C12C-C13C \\sim C12C-C14C \\sim C13C-C14C
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C14A) = Uanis(C14B) = Uanis(C14C)
Uanis(C12A) = Uanis(C12B) = Uanis(C12C)
Uanis(C13A) = Uanis(C13B) = Uanis(C13C)
4. Others
 Fixed Sof: C12A(0.62) H12a(0.62) H12b(0.62) H12c(0.62) C13A(0.62) H13a(0.62)
 H13b(0.62) H13c(0.62) C14A(0.62) H14a(0.62) H14b(0.62) H14c(0.62) C12B(0.22)
 H12d(0.22) H12e(0.22) H12f(0.22) C13B(0.22) H13d(0.22) H13e(0.22) H13f(0.22)
 C14B(0.22) H14d(0.22) H14e(0.22) H14f(0.22) C12C(0.16) H12g(0.16) H12h(0.16)
 H12i(0.16) C13C(0.16) H13g(0.16) H13h(0.16) H13i(0.16) C14C(0.16) H14g(0.16)
 H14h(0.16) H14i(0.16)
5.a Ternary CH refined with riding coordinates:
 C3(H3)
5.b Secondary CH2 refined with riding coordinates:
 C2(H2a,H2b), C4(H4a,H4b)
5.c Me refined with riding coordinates:
 C12A(H12a,H12b,H12c), C13A(H13a,H13b,H13c), C14A(H14a,H14b,H14c), C12B(H12d,
 H12e,H12f), C13B(H13d,H13e,H13f), C14B(H14d,H14e,H14f), C12C(H12g,H12h,H12i),
 C13C(H13g,H13h,H13i), C14C(H14g,H14h,H14i)
5.d Aromatic/amide H refined with riding coordinates:
 N2(H2)
5.e Idealised Me refined as rotating group:
 C6(H6a,H6b,H6c), C7(H7a,H7b,H7c), C8(H8a,H8b,H8c), C9(H9a,H9b,H9c)
;