#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2006944.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2006944
loop_
_publ_author_name
'Merino, P.'
'Merchan, F. L.'
'Tejero, T.'
'Lanaspa, A.'
_publ_section_title
;
 Chiral Hydroxylamines. V.
 (2<i>S</i>,3<i>S</i>)-<i>N</i>-Benzyl-<i>N</i>-[3-(<i>tert</i>-butoxycarbonylamino)-2-butyl]hydroxylamine
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              85
_journal_page_last               86
_journal_volume                  54
_journal_year                    1998
_chemical_formula_sum            'C16 H26 N2 O3'
_chemical_formula_weight         294.39
_chemical_melting_point          397
_chemical_name_systematic
;
 (2S,3S)-N-Benzyl-N-[3-(tert-butoxycarbonylamino)-2-butyl]hydroxylamine
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.0
_cell_angle_beta                 94.57(5)
_cell_angle_gamma                90.0
_cell_formula_units_Z            2
_cell_length_a                   6.358(5)
_cell_length_b                   10.463(5)
_cell_length_c                   12.842(5)
_cell_measurement_reflns_used    38
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.025
_cell_measurement_theta_min      10.099
_cell_volume                     851.6(9)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Siemens, 1992)'
_computing_data_reduction        XSCANS
_computing_molecular_graphics    'SHELXTL-Plus (Sheldrick, 1991)'
_computing_publication_material  SHELXTL-Plus
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       '2\q/\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0683
_diffrn_reflns_av_sigmaI/netI    0.0704
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            2349
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         2.51
_diffrn_standards_decay_%        7.24
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.148
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_description       'transparent block'
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.235
_refine_ls_extinction_coef       none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.025
_refine_ls_goodness_of_fit_obs   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         1749
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.063
_refine_ls_restrained_S_obs      1.055
_refine_ls_R_factor_all          0.0730
_refine_ls_R_factor_obs          0.0505
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w = 1/[\s^2^(Fo^2^)+(0.0889P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_all         0.1481
_refine_ls_wR_factor_obs         0.1292
_reflns_number_gt                1458
_reflns_number_total             1841
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    na1318.cif
_[local]_cod_data_source_block   ala3
_[local]_cod_cif_authors_sg_H-M  P21
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '397 K' was changed to '397' - the
value should be numeric and without a unit designator.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2006944
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O2 0.0179(12) 0.053(2) 0.0301(12) 0.0012(14) -0.0031(10) -0.0102(15)
O1 0.0174(11) 0.036(2) 0.0261(12) -0.0004(13) -0.0056(10) -0.0035(14)
O3 0.0211(13) 0.058(2) 0.0385(15) 0.0044(15) -0.0048(11) -0.022(2)
N1 0.0202(14) 0.030(2) 0.0216(13) 0.0004(14) -0.0047(11) -0.0004(15)
N2 0.0155(13) 0.039(2) 0.034(2) -0.003(2) 0.0013(12) -0.008(2)
C4 0.031(2) 0.027(2) 0.038(2) 0.003(2) 0.003(2) -0.006(2)
C7 0.029(2) 0.037(3) 0.048(2) 0.000(2) 0.003(2) -0.005(2)
C3 0.022(2) 0.023(2) 0.023(2) -0.001(2) -0.0025(14) -0.002(2)
C6 0.032(2) 0.032(2) 0.027(2) -0.001(2) 0.002(2) 0.006(2)
C2 0.019(2) 0.027(2) 0.034(2) 0.000(2) 0.0003(15) -0.001(2)
C5 0.035(2) 0.037(3) 0.026(2) -0.001(2) 0.007(2) -0.003(2)
C12 0.019(2) 0.039(2) 0.026(2) -0.002(2) 0.0029(14) -0.001(2)
C8 0.043(3) 0.035(3) 0.060(3) 0.002(2) 0.006(2) 0.001(3)
C11 0.036(2) 0.049(3) 0.038(2) -0.004(2) 0.010(2) 0.006(2)
C13 0.025(2) 0.051(3) 0.039(2) 0.003(2) 0.002(2) -0.014(2)
C1 0.033(2) 0.040(3) 0.055(3) -0.011(2) 0.016(2) -0.003(2)
C10 0.034(2) 0.048(3) 0.050(3) -0.013(2) 0.004(2) 0.009(3)
C9 0.047(2) 0.031(3) 0.055(3) -0.007(2) -0.005(2) 0.003(2)
C14 0.039(2) 0.068(4) 0.032(2) 0.004(3) 0.002(2) -0.017(3)
C15 0.045(3) 0.060(4) 0.054(3) 0.017(3) 0.002(2) -0.020(3)
C16 0.051(3) 0.053(3) 0.059(3) -0.005(3) 0.004(2) -0.017(3)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
O2 0.4601(4) 0.8043(3) 0.8973(2) 0.0340(7) Uani d . 1 O
O1 0.7412(3) 0.7303(3) 0.7607(2) 0.0270(6) Uani d . 1 O
H(O) 0.746(9) 0.789(4) 0.806(3) 0.12(3) Uiso calc R 1 H
O3 0.1221(4) 0.8770(4) 0.8784(2) 0.0394(8) Uani d . 1 O
N1 0.5740(4) 0.7576(3) 0.6795(2) 0.0243(8) Uani d . 1 N
N2 0.2079(4) 0.7133(4) 0.7848(3) 0.0295(8) Uani d . 1 N
H(N) 0.0785(4) 0.7219(4) 0.7559(3) 0.061(6) Uiso calc R 1 H
C4 0.5944(6) 0.5258(4) 0.6274(3) 0.0319(10) Uani d . 1 C
H4A 0.6709(6) 0.5493(4) 0.5669(3) 0.068(5) Uiso calc R 1 H
H4B 0.5044(6) 0.4516(4) 0.6098(3) 0.068(5) Uiso calc R 1 H
H4C 0.6956(6) 0.5045(4) 0.6864(3) 0.068(5) Uiso calc R 1 H
C7 0.6075(7) 1.0319(5) 0.6539(4) 0.0379(11) Uani d . 1 C
H7 0.4717(7) 1.0035(5) 0.6696(4) 0.061(6) Uiso calc R 1 H
C3 0.4580(5) 0.6377(4) 0.6570(3) 0.0229(8) Uani d . 1 C
H3 0.3525(5) 0.6543(4) 0.5965(3) 0.039(6) Uiso calc R 1 H
C6 0.7460(6) 0.9457(4) 0.6135(3) 0.0306(9) Uani d . 1 C
C2 0.3340(6) 0.6055(4) 0.7521(3) 0.0266(9) Uani d . 1 C
H2 0.4386(6) 0.5833(4) 0.8116(3) 0.039(6) Uiso calc R 1 H
C5 0.6814(6) 0.8094(5) 0.5923(3) 0.0326(10) Uani d . 1 C
H5A 0.5860(6) 0.8052(5) 0.5276(3) 0.039(6) Uiso calc R 1 H
H5B 0.8079(6) 0.7572(5) 0.5818(3) 0.039(6) Uiso calc R 1 H
C12 0.2780(5) 0.7985(5) 0.8553(3) 0.0276(9) Uani d . 1 C
C8 0.6623(8) 1.1561(5) 0.6713(4) 0.0461(12) Uani d . 1 C
H8 0.5650(8) 1.2131(5) 0.6993(4) 0.061(6) Uiso calc R 1 H
C11 0.9441(7) 0.9880(6) 0.5914(3) 0.0407(12) Uani d . 1 C
H11 1.0411(7) 0.9307(6) 0.5636(3) 0.061(6) Uiso calc R 1 H
C13 0.1561(6) 0.9833(5) 0.9530(3) 0.0382(11) Uani d . 1 C
C1 0.1898(7) 0.4902(5) 0.7311(4) 0.0422(12) Uani d . 1 C
H1A 0.1139(7) 0.4726(5) 0.7930(4) 0.068(5) Uiso calc R 1 H
H1B 0.2748(7) 0.4155(5) 0.7153(4) 0.068(5) Uiso calc R 1 H
H1C 0.0882(7) 0.5084(5) 0.6715(4) 0.068(5) Uiso calc R 1 H
C10 1.0003(7) 1.1158(5) 0.6101(4) 0.0444(12) Uani d . 1 C
H10 1.1372(7) 1.1441(5) 0.5962(4) 0.061(6) Uiso calc R 1 H
C9 0.8614(7) 1.2005(5) 0.6483(4) 0.0449(12) Uani d . 1 C
H9 0.8992(7) 1.2877(5) 0.6590(4) 0.061(6) Uiso calc R 1 H
C14 0.2335(7) 0.9327(6) 1.0597(3) 0.0463(13) Uani d . 1 C
H14A 0.1323(7) 0.8702(6) 1.0828(3) 0.068(5) Uiso calc R 1 H
H14B 0.2471(7) 1.0036(6) 1.1097(3) 0.068(5) Uiso calc R 1 H
H14C 0.3711(7) 0.8916(6) 1.0558(3) 0.068(5) Uiso calc R 1 H
C15 -0.0672(7) 1.0367(6) 0.9556(4) 0.0530(14) Uani d . 1 C
H15A -0.1158(7) 1.0691(6) 0.8862(4) 0.068(5) Uiso calc R 1 H
H15B -0.0668(7) 1.1064(6) 1.0066(4) 0.068(5) Uiso calc R 1 H
H15C -0.1621(7) 0.9688(6) 0.9756(4) 0.068(5) Uiso calc R 1 H
C16 0.3044(8) 1.0817(6) 0.9106(4) 0.0545(14) Uani d . 1 C
H16A 0.2464(8) 1.1108(6) 0.8416(4) 0.068(5) Uiso calc R 1 H
H16B 0.4431(8) 1.0427(6) 0.9045(4) 0.068(5) Uiso calc R 1 H
H16C 0.3190(8) 1.1547(6) 0.9584(4) 0.068(5) Uiso calc R 1 H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
N1 O1 H(O) 109.5(2) ?
C12 O3 C13 122.3(3) ?
O1 N1 C5 105.2(3) yes
O1 N1 C3 107.4(3) yes
C5 N1 C3 115.0(3) yes
C12 N2 C2 123.6(3) ?
C12 N2 H(N) 118.2(2) ?
C2 N2 H(N) 118.2(2) ?
C3 C4 H4A 109.5(2) ?
C3 C4 H4B 109.5(2) ?
H4A C4 H4B 109.5 ?
C3 C4 H4C 109.5(2) ?
H4A C4 H4C 109.5 ?
H4B C4 H4C 109.5 ?
C8 C7 C6 121.3(4) ?
C8 C7 H7 119.3(3) ?
C6 C7 H7 119.3(3) ?
N1 C3 C4 114.7(3) ?
N1 C3 C2 108.1(3) ?
C4 C3 C2 111.5(3) ?
N1 C3 H3 107.4(2) ?
C4 C3 H3 107.4(2) ?
C2 C3 H3 107.4(2) ?
C11 C6 C7 118.8(5) ?
C11 C6 C5 120.4(4) ?
C7 C6 C5 120.8(4) ?
N2 C2 C1 109.0(3) yes
N2 C2 C3 112.6(3) yes
C1 C2 C3 111.8(3) yes
N2 C2 H2 107.8(2) ?
C1 C2 H2 107.8(2) ?
C3 C2 H2 107.8(2) ?
N1 C5 C6 110.6(3) ?
N1 C5 H5A 109.5(2) ?
C6 C5 H5A 109.5(2) ?
N1 C5 H5B 109.5(2) ?
C6 C5 H5B 109.5(2) ?
H5A C5 H5B 108.1 ?
O2 C12 N2 125.6(4) yes
O2 C12 O3 123.8(4) yes
N2 C12 O3 110.5(3) yes
C7 C8 C9 120.5(5) ?
C7 C8 H8 119.8(3) ?
C9 C8 H8 119.8(3) ?
C6 C11 C10 119.6(5) ?
C6 C11 H11 120.2(3) ?
C10 C11 H11 120.2(3) ?
O3 C13 C14 110.2(4) ?
O3 C13 C16 109.9(4) ?
C14 C13 C16 113.2(4) ?
O3 C13 C15 101.6(3) ?
C14 C13 C15 110.1(4) ?
C16 C13 C15 111.3(5) ?
C2 C1 H1A 109.5(2) ?
C2 C1 H1B 109.5(2) ?
H1A C1 H1B 109.5 ?
C2 C1 H1C 109.5(2) ?
H1A C1 H1C 109.5 ?
H1B C1 H1C 109.5 ?
C9 C10 C11 121.1(4) ?
C9 C10 H10 119.4(3) ?
C11 C10 H10 119.4(3) ?
C10 C9 C8 118.6(5) ?
C10 C9 H9 120.7(3) ?
C8 C9 H9 120.7(3) ?
C13 C14 H14A 109.5(3) ?
C13 C14 H14B 109.5(3) ?
H14A C14 H14B 109.5 ?
C13 C14 H14C 109.5(2) ?
H14A C14 H14C 109.5 ?
H14B C14 H14C 109.5 ?
C13 C15 H15A 109.5(3) ?
C13 C15 H15B 109.5(3) ?
H15A C15 H15B 109.5 ?
C13 C15 H15C 109.5(3) ?
H15A C15 H15C 109.5 ?
H15B C15 H15C 109.5 ?
C13 C16 H16A 109.5(3) ?
C13 C16 H16B 109.5(3) ?
H16A C16 H16B 109.5 ?
C13 C16 H16C 109.5(3) ?
H16A C16 H16C 109.5 ?
H16B C16 H16C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O2 C12 1.239(4) yes
O1 N1 1.457(4) yes
O1 H(O) 0.84 ?
O3 C12 1.338(5) yes
O3 C13 1.472(6) yes
N1 C5 1.461(5) yes
N1 C3 1.472(5) yes
N2 C12 1.323(5) yes
N2 C2 1.465(6) yes
N2 H(N) 0.88 ?
C4 C3 1.523(6) yes
C4 H4A 0.98 ?
C4 H4B 0.98 ?
C4 H4C 0.98 ?
C7 C8 1.359(8) ?
C7 C6 1.389(7) ?
C7 H7 0.95 ?
C3 C2 1.543(5) yes
C3 H3 1.00 ?
C6 C11 1.386(6) ?
C6 C5 1.503(7) ?
C2 C1 1.526(6) yes
C2 H2 1.00 ?
C5 H5A 0.99 ?
C5 H5B 0.99 ?
C8 C9 1.403(7) ?
C8 H8 0.95 ?
C11 C10 1.400(8) ?
C11 H11 0.95 ?
C13 C14 1.515(6) ?
C13 C16 1.526(8) ?
C13 C15 1.528(6) ?
C1 H1A 0.98 ?
C1 H1B 0.98 ?
C1 H1C 0.98 ?
C10 C9 1.369(7) ?
C10 H10 0.95 ?
C9 H9 0.95 ?
C14 H14A 0.98 ?
C14 H14B 0.98 ?
C14 H14C 0.98 ?
C15 H15A 0.98 ?
C15 H15B 0.98 ?
C15 H15C 0.98 ?
C16 H16A 0.98 ?
C16 H16B 0.98 ?
C16 H16C 0.98 ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_publ_flag
C1 C2 C3 C4 -59.3(4) yes
N1 C3 C2 N2 50.8(4) yes
C1 C2 C3 N1 173.8(3) yes
C4 C3 C2 N2 177.7(3) yes
N2 C12 O3 C13 -178.5(4) ?
C6 C7 C8 C9 0.3(8) ?
C7 C8 C9 C10 -1.3(8) ?
C8 C9 C10 C11 1.8(7) ?