#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/06/2230680.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_2230680
loop_
_publ_author_name
'Pinheiro, Alessandra C.'
'de Souza, Marcus V. N.'
'Tiekink, Edward R. T.'
'Wardell, Solange M. S. V.'
'Wardell, James L.'
_publ_section_title
;
 tert-Butyl
 N-((1S)-2-hydroxy-1-{N'-[(1E)-4-methoxybenzylidene]hydrazinecarbonyl}ethyl)carbamate
;
_journal_coeditor_code           HB5921
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1805
_journal_page_last               o1806
_journal_paper_doi               10.1107/S1600536811024263
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C16 H23 N3 O5'
_chemical_formula_moiety         'C16 H23 N3 O5'
_chemical_formula_sum            'C16 H23 N3 O5'
_chemical_formula_weight         337.38
_chemical_name_systematic
;
tert-Butyl N-((1S)-2-hydroxy-1-{N'-[(1E)-
4-methoxybenzylidene]hydrazinecarbonyl}ethyl)carbamate
;
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                79.919(4)
_cell_angle_beta                 83.686(4)
_cell_angle_gamma                76.505(4)
_cell_formula_units_Z            1
_cell_length_a                   5.3323(4)
_cell_length_b                   5.7200(4)
_cell_length_c                   14.3319(10)
_cell_measurement_reflns_used    14323
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.9
_cell_volume                     417.41(5)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_data_collection       'COLLECT (Hooft, 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type
'Bruker--Nonius Roper CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_av_sigmaI/netI    0.0451
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7495
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         3.71
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.887
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             180
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.247
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         1900
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0653
_refine_ls_R_factor_gt           0.0510
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0304P)²+0.3732P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1033
_refine_ls_wR_factor_ref         0.1133
_reflns_number_gt                1661
_reflns_number_total             1900
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5921.cif
_cod_data_source_block           I
_cod_database_code               2230680
_cod_database_fobs_code          2230680
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 1.6917(5) 0.8513(5) 0.7563(2) 0.0280(7) Uani d . 1 1 . .
O O2 0.9933(5) 0.3081(5) 0.3426(2) 0.0259(6) Uani d . 1 1 . .
O O3 0.4988(5) 0.1450(5) 0.3533(2) 0.0244(6) Uani d D 1 1 . .
H H3O 0.340(3) 0.190(9) 0.369(3) 0.037 Uiso d D 1 1 . .
O O4 0.4967(5) 0.9626(5) 0.06608(19) 0.0228(6) Uani d . 1 1 . .
O O5 0.2010(5) 0.7831(5) 0.1623(2) 0.0250(6) Uani d . 1 1 . .
N N1 1.0286(6) 0.6618(6) 0.4406(2) 0.0215(7) Uani d . 1 1 . .
N N2 0.8274(6) 0.6827(6) 0.3836(2) 0.0209(7) Uani d D 1 1 . .
H H2N 0.709(6) 0.818(5) 0.373(3) 0.025 Uiso d D 1 1 . .
N N3 0.6282(6) 0.6919(6) 0.1906(2) 0.0212(7) Uani d D 1 1 . .
H H3N 0.777(5) 0.731(8) 0.171(3) 0.025 Uiso d D 1 1 . .
C C1 1.2010(7) 0.8412(7) 0.5502(3) 0.0194(8) Uani d . 1 1 . .
C C2 1.4019(7) 0.6394(7) 0.5725(3) 0.0211(8) Uani d . 1 1 . .
H H2 1.4244 0.5028 0.5406 0.025 Uiso calc R 1 1 . .
C C3 1.5699(7) 0.6361(7) 0.6412(3) 0.0222(8) Uani d . 1 1 . .
H H3 1.7053 0.4975 0.6560 0.027 Uiso calc R 1 1 . .
C C4 1.5392(7) 0.8349(7) 0.6876(3) 0.0229(8) Uani d . 1 1 . .
C C5 1.3430(8) 1.0405(7) 0.6634(3) 0.0256(9) Uani d . 1 1 . .
H H5 1.3242 1.1793 0.6937 0.031 Uiso calc R 1 1 . .
C C6 1.1777(8) 1.0429(7) 0.5961(3) 0.0251(9) Uani d . 1 1 . .
H H6 1.0453 1.1836 0.5805 0.030 Uiso calc R 1 1 . .
C C7 1.8959(8) 0.6473(8) 0.7822(3) 0.0280(9) Uani d . 1 1 . .
H H7A 1.8249 0.5017 0.8027 0.042 Uiso calc R 1 1 . .
H H7B 1.9827 0.6773 0.8343 0.042 Uiso calc R 1 1 . .
H H7C 2.0207 0.6225 0.7274 0.042 Uiso calc R 1 1 . .
C C8 1.0108(8) 0.8446(7) 0.4829(3) 0.0229(8) Uani d . 1 1 . .
H H8 0.8738 0.9833 0.4709 0.027 Uiso calc R 1 1 . .
C C9 0.8245(7) 0.4972(7) 0.3388(3) 0.0195(7) Uani d . 1 1 . .
C C10 0.5925(7) 0.5327(7) 0.2797(3) 0.0188(7) Uani d . 1 1 . .
H H10 0.4336 0.6117 0.3161 0.023 Uiso calc R 1 1 . .
C C11 0.5605(7) 0.2847(7) 0.2643(3) 0.0226(8) Uani d . 1 1 . .
H H11A 0.4206 0.3063 0.2214 0.027 Uiso calc R 1 1 . .
H H11B 0.7227 0.1972 0.2339 0.027 Uiso calc R 1 1 . .
C C12 0.4209(7) 0.8111(7) 0.1416(3) 0.0188(7) Uani d . 1 1 . .
C C13 0.3072(7) 1.1111(7) -0.0009(3) 0.0213(8) Uani d . 1 1 . .
C C14 0.4761(8) 1.2529(7) -0.0707(3) 0.0264(9) Uani d . 1 1 . .
H H14A 0.5607 1.3426 -0.0360 0.040 Uiso calc R 1 1 . .
H H14B 0.3684 1.3678 -0.1172 0.040 Uiso calc R 1 1 . .
H H14C 0.6079 1.1395 -0.1037 0.040 Uiso calc R 1 1 . .
C C15 0.0964(8) 1.2826(7) 0.0503(3) 0.0250(8) Uani d . 1 1 . .
H H15A -0.0152 1.1886 0.0920 0.038 Uiso calc R 1 1 . .
H H15B -0.0070 1.4008 0.0034 0.038 Uiso calc R 1 1 . .
H H15C 0.1759 1.3688 0.0882 0.038 Uiso calc R 1 1 . .
C C16 0.1993(8) 0.9468(7) -0.0514(3) 0.0244(8) Uani d . 1 1 . .
H H16A 0.3423 0.8281 -0.0770 0.037 Uiso calc R 1 1 . .
H H16B 0.0995 1.0457 -0.1036 0.037 Uiso calc R 1 1 . .
H H16C 0.0868 0.8610 -0.0063 0.037 Uiso calc R 1 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C4 O1 C7 . . 117.4(3) ?
C11 O3 H3O . . 109(3) ?
C12 O4 C13 . . 120.5(3) ?
C8 N1 N2 . . 114.4(3) ?
C9 N2 N1 . . 118.8(3) ?
C9 N2 H2N . . 119(3) ?
N1 N2 H2N . . 122(3) ?
C12 N3 C10 . . 119.8(3) ?
C12 N3 H3N . . 117(3) ?
C10 N3 H3N . . 122(3) ?
C2 C1 C6 . . 118.3(4) ?
C2 C1 C8 . . 122.2(3) ?
C6 C1 C8 . . 119.5(3) ?
C1 C2 C3 . . 120.8(3) ?
C1 C2 H2 . . 119.6 ?
C3 C2 H2 . . 119.6 ?
C4 C3 C2 . . 120.0(3) ?
C4 C3 H3 . . 120.0 ?
C2 C3 H3 . . 120.0 ?
O1 C4 C3 . . 125.0(3) ?
O1 C4 C5 . . 115.6(3) ?
C3 C4 C5 . . 119.4(3) ?
C6 C5 C4 . . 120.4(4) ?
C6 C5 H5 . . 119.8 ?
C4 C5 H5 . . 119.8 ?
C5 C6 C1 . . 121.0(4) ?
C5 C6 H6 . . 119.5 ?
C1 C6 H6 . . 119.5 ?
O1 C7 H7A . . 109.5 ?
O1 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
O1 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
N1 C8 C1 . . 120.4(3) ?
N1 C8 H8 . . 119.8 ?
C1 C8 H8 . . 119.8 ?
O2 C9 N2 . . 124.3(4) ?
O2 C9 C10 . . 120.3(3) ?
N2 C9 C10 . . 115.4(3) ?
N3 C10 C11 . . 112.2(3) ?
N3 C10 C9 . . 109.8(3) ?
C11 C10 C9 . . 109.1(3) ?
N3 C10 H10 . . 108.6 ?
C11 C10 H10 . . 108.6 ?
C9 C10 H10 . . 108.6 ?
O3 C11 C10 . . 110.0(3) ?
O3 C11 H11A . . 109.7 ?
C10 C11 H11A . . 109.7 ?
O3 C11 H11B . . 109.7 ?
C10 C11 H11B . . 109.7 ?
H11A C11 H11B . . 108.2 ?
O5 C12 N3 . . 124.9(3) ?
O5 C12 O4 . . 125.6(3) ?
N3 C12 O4 . . 109.5(3) ?
O4 C13 C15 . . 110.6(3) ?
O4 C13 C16 . . 110.2(3) ?
C15 C13 C16 . . 112.6(3) ?
O4 C13 C14 . . 101.7(3) ?
C15 C13 C14 . . 110.9(3) ?
C16 C13 C14 . . 110.4(3) ?
C13 C14 H14A . . 109.5 ?
C13 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C13 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C13 C15 H15A . . 109.5 ?
C13 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C13 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C13 C16 H16A . . 109.5 ?
C13 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C13 C16 H16C . . 109.5 ?
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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C4 . 1.372(5) ?
O1 C7 . 1.425(5) ?
O2 C9 . 1.233(5) ?
O3 C11 . 1.431(4) ?
O3 H3O . 0.841(10) ?
O4 C12 . 1.350(4) ?
O4 C13 . 1.480(4) ?
O5 C12 . 1.218(4) ?
N1 C8 . 1.278(5) ?
N1 N2 . 1.389(4) ?
N2 C9 . 1.336(5) ?
N2 H2N . 0.880(10) ?
N3 C12 . 1.353(5) ?
N3 C10 . 1.455(5) ?
N3 H3N . 0.880(10) ?
C1 C2 . 1.397(5) ?
C1 C6 . 1.401(6) ?
C1 C8 . 1.469(5) ?
C2 C3 . 1.397(5) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.385(5) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.400(6) ?
C5 C6 . 1.372(6) ?
C5 H5 . 0.9500 ?
C6 H6 . 0.9500 ?
C7 H7A . 0.9800 ?
C7 H7B . 0.9800 ?
C7 H7C . 0.9800 ?
C8 H8 . 0.9500 ?
C9 C10 . 1.530(5) ?
C10 C11 . 1.524(5) ?
C10 H10 . 1.0000 ?
C11 H11A . 0.9900 ?
C11 H11B . 0.9900 ?
C13 C15 . 1.523(5) ?
C13 C16 . 1.523(5) ?
C13 C14 . 1.526(5) ?
C14 H14A . 0.9800 ?
C14 H14B . 0.9800 ?
C14 H14C . 0.9800 ?
C15 H15A . 0.9800 ?
C15 H15B . 0.9800 ?
C15 H15C . 0.9800 ?
C16 H16A . 0.9800 ?
C16 H16B . 0.9800 ?
C16 H16C . 0.9800 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O3 H3o O2 1_455 0.84(3) 1.87(3) 2.651(4) 153(4)
N2 H2n O3 1_565 0.88(3) 1.93(3) 2.803(4) 169(3)
N3 H3n O5 1_655 0.88(3) 2.34(3) 3.188(4) 164(4)
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C8 N1 N2 C9 . . . . -177.8(3) ?
C6 C1 C2 C3 . . . . 2.0(6) ?
C8 C1 C2 C3 . . . . -176.0(4) ?
C1 C2 C3 C4 . . . . -0.3(6) ?
C7 O1 C4 C3 . . . . -0.5(5) ?
C7 O1 C4 C5 . . . . -179.2(4) ?
C2 C3 C4 O1 . . . . 179.7(4) ?
C2 C3 C4 C5 . . . . -1.6(6) ?
O1 C4 C5 C6 . . . . -179.4(4) ?
C3 C4 C5 C6 . . . . 1.8(6) ?
C4 C5 C6 C1 . . . . -0.1(6) ?
C2 C1 C6 C5 . . . . -1.8(6) ?
C8 C1 C6 C5 . . . . 176.2(4) ?
N2 N1 C8 C1 . . . . 176.1(3) ?
C2 C1 C8 N1 . . . . -1.8(5) ?
C6 C1 C8 N1 . . . . -179.8(4) ?
N1 N2 C9 O2 . . . . -1.9(5) ?
N1 N2 C9 C10 . . . . 178.5(3) ?
C12 N3 C10 C11 . . . . 79.8(4) ?
C12 N3 C10 C9 . . . . -158.7(3) ?
O2 C9 C10 N3 . . . . -102.2(4) ?
N2 C9 C10 N3 . . . . 77.5(4) ?
O2 C9 C10 C11 . . . . 21.1(5) ?
N2 C9 C10 C11 . . . . -159.2(3) ?
N3 C10 C11 O3 . . . . -173.9(3) ?
C9 C10 C11 O3 . . . . 64.3(4) ?
C10 N3 C12 O5 . . . . -5.9(6) ?
C10 N3 C12 O4 . . . . 174.9(3) ?
C13 O4 C12 O5 . . . . -0.7(5) ?
C13 O4 C12 N3 . . . . 178.6(3) ?
C12 O4 C13 C15 . . . . 60.9(4) ?
C12 O4 C13 C16 . . . . -64.3(4) ?
C12 O4 C13 C14 . . . . 178.7(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656771
