#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/55/2225517.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_2225517
loop_
_publ_author_name
'Pinheiro, Alessandra C.'
'de Souza, Marcus V. N.'
'Wardell, Solange M. S. V.'
'Wardell, James L.'
'Tiekink, Edward R. T.'
_publ_section_title
;
 tert-Butyl
 N-[(S)-1-hydrazinecarbonyl-2-hydroxyethyl]carbamate
;
_journal_coeditor_code           HB5376
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o994
_journal_paper_doi               10.1107/S1600536810011438
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C8 H17 N3 O4'
_chemical_formula_moiety         'C8 H17 N3 O4'
_chemical_formula_sum            'C8 H17 N3 O4'
_chemical_formula_weight         219.25
_chemical_name_systematic
;
tert-Butyl
N-[(S)-1-hydrazinecarbonyl-2-hydroxyethyl]carbamate
;
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 94.483(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.9274(5)
_cell_length_b                   5.0074(4)
_cell_length_c                   16.2388(15)
_cell_measurement_reflns_used    10838
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.9
_cell_volume                     561.57(8)
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  '10 cm confocal mirrors'
_diffrn_radiation_source         'Enraf--Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.062
_diffrn_reflns_av_sigmaI/netI    0.049
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            6687
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         3.0
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.616
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             236
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.30
_refine_diff_density_min         -0.34
_refine_ls_abs_structure_details nd
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.23
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         1428
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.23
_refine_ls_R_factor_all          0.068
_refine_ls_R_factor_gt           0.046
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0838P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.110
_refine_ls_wR_factor_ref         0.149
_reflns_number_gt                1168
_reflns_number_total             1428
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5376.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2225517
_cod_database_fobs_code          2225517
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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_disorder_assembly
_atom_site_disorder_group
O O1 0.2906(3) 0.6236(5) 0.55336(15) 0.0226(6) Uani d . 1 . .
O O2 -0.0983(3) 0.3069(5) 0.64307(16) 0.0245(6) Uani d D 1 . .
H H1O -0.149(6) 0.452(5) 0.627(3) 0.037 Uiso d D 1 . .
O O3 0.4633(4) -0.1207(6) 0.74118(17) 0.0298(7) Uani d . 1 . .
O O4 0.6317(3) 0.2100(5) 0.81155(14) 0.0223(6) Uani d . 1 . .
N N1 0.2779(4) 0.2663(6) 0.42051(18) 0.0223(7) Uani d D 1 . .
H H1N 0.205(5) 0.414(5) 0.409(3) 0.027 Uiso d D 1 . .
H H2N 0.4053(15) 0.288(9) 0.412(2) 0.027 Uiso d D 1 . .
N N2 0.2663(4) 0.1984(5) 0.50498(18) 0.0198(6) Uani d D 1 . .
H H3N 0.230(5) 0.033(3) 0.513(2) 0.024 Uiso d D 1 . .
N N3 0.4237(4) 0.3155(5) 0.70510(18) 0.0207(6) Uani d D 1 . .
H H4N 0.429(6) 0.485(2) 0.720(2) 0.025 Uiso d D 1 . .
C C1 0.2715(4) 0.3813(8) 0.5650(2) 0.0181(7) Uani d . 1 . .
C C2 0.2480(4) 0.2659(8) 0.65093(19) 0.0182(7) Uani d . 1 . .
H H2 0.2267 0.0688 0.6460 0.022 Uiso calc R 1 . .
C C3 0.0743(2) 0.3924(5) 0.68777(11) 0.0213(7) Uani d . 1 . .
H H3A 0.0723 0.3398 0.7465 0.026 Uiso calc R 1 . .
H H3B 0.0842 0.5894 0.6852 0.026 Uiso calc R 1 . .
C C4 0.5023(2) 0.1141(5) 0.75191(11) 0.0193(7) Uani d . 1 . .
C C5 0.7406(2) 0.0190(5) 0.86737(11) 0.0218(7) Uani d . 1 . .
C C6 0.8669(2) 0.2032(5) 0.92338(11) 0.0317(9) Uani d . 1 . .
H H6A 0.9567 0.3001 0.8904 0.047 Uiso calc R 1 . .
H H6B 0.9406 0.0969 0.9657 0.047 Uiso calc R 1 . .
H H6C 0.7847 0.3310 0.9501 0.047 Uiso calc R 1 . .
C C7 0.6005(6) -0.1336(9) 0.9179(2) 0.0300(8) Uani d . 1 . .
H H7A 0.5109 -0.0078 0.9411 0.045 Uiso calc R 1 . .
H H7B 0.6735 -0.2291 0.9629 0.045 Uiso calc R 1 . .
H H7C 0.5272 -0.2620 0.8823 0.045 Uiso calc R 1 . .
C C8 0.8656(5) -0.1602(7) 0.8176(2) 0.0246(8) Uani d . 1 . .
H H8A 0.7860 -0.3046 0.7922 0.037 Uiso calc R 1 . .
H H8B 0.9705 -0.2366 0.8542 0.037 Uiso calc R 1 . .
H H8C 0.9207 -0.0549 0.7743 0.037 Uiso calc R 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C3 O2 H1O . . 102(3) ?
C4 O4 C5 . . 119.0(2) ?
N2 N1 H1N . . 109(3) ?
N2 N1 H2N . . 107(2) ?
H1N N1 H2N . . 114(4) ?
C1 N2 N1 . . 122.7(3) ?
C1 N2 H3N . . 122(3) ?
N1 N2 H3N . . 114(3) ?
C4 N3 C2 . . 119.3(3) ?
C4 N3 H4N . . 124(3) ?
C2 N3 H4N . . 110(3) ?
O1 C1 N2 . . 123.9(3) ?
O1 C1 C2 . . 122.0(3) ?
N2 C1 C2 . . 114.0(3) ?
N3 C2 C3 . . 109.8(2) ?
N3 C2 C1 . . 109.9(3) ?
C3 C2 C1 . . 110.2(2) ?
N3 C2 H2 . . 109.0 ?
C3 C2 H2 . . 109.0 ?
C1 C2 H2 . . 109.0 ?
O2 C3 C2 . . 109.54(19) ?
O2 C3 H3A . . 109.8 ?
C2 C3 H3A . . 109.8 ?
O2 C3 H3B . . 109.8 ?
C2 C3 H3B . . 109.8 ?
H3A C3 H3B . . 108.2 ?
O3 C4 N3 . . 124.4(2) ?
O3 C4 O4 . . 124.9(2) ?
N3 C4 O4 . . 110.6(2) ?
O4 C5 C8 . . 109.80(19) ?
O4 C5 C6 . . 102.46(12) ?
C8 C5 C6 . . 110.49(15) ?
O4 C5 C7 . . 109.8(2) ?
C8 C5 C7 . . 113.7(2) ?
C6 C5 C7 . . 109.99(17) ?
C5 C6 H6A . . 109.5 ?
C5 C6 H6B . . 109.5 ?
H6A C6 H6B . . 109.5 ?
C5 C6 H6C . . 109.5 ?
H6A C6 H6C . . 109.5 ?
H6B C6 H6C . . 109.5 ?
C5 C7 H7A . . 109.5 ?
C5 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
C5 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
C5 C8 H8A . . 109.5 ?
C5 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C5 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 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 C1 . 1.236(4) ?
O2 C3 . 1.416(3) ?
O2 H1O . 0.84(3) ?
O3 C4 . 1.216(3) ?
O4 C4 . 1.355(3) ?
O4 C5 . 1.482(3) ?
N1 N2 . 1.421(4) ?
N1 H1N . 0.91(3) ?
N1 H2N . 0.911(13) ?
N2 C1 . 1.336(5) ?
N2 H3N . 0.878(18) ?
N3 C4 . 1.352(3) ?
N3 C2 . 1.466(4) ?
N3 H4N . 0.883(14) ?
C1 C2 . 1.531(5) ?
C2 C3 . 1.523(4) ?
C2 H2 . 1.0000 ?
C3 H3A . 0.9900 ?
C3 H3B . 0.9900 ?
C5 C8 . 1.523(4) ?
C5 C6 . 1.523(3) ?
C5 C7 . 1.525(4) ?
C6 H6A . 0.9800 ?
C6 H6B . 0.9800 ?
C6 H6C . 0.9800 ?
C7 H7A . 0.9800 ?
C7 H7B . 0.9800 ?
C7 H7C . 0.9800 ?
C8 H8A . 0.9800 ?
C8 H8B . 0.9800 ?
C8 H8C . 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
O2 H1o N1 2_556 0.84(3) 1.94(3) 2.776(4) 174(5)
N1 H1n O2 2_556 0.91(3) 2.24(3) 3.121(4) 162(4)
N1 H2n O1 2_646 0.911(13) 2.29(2) 3.070(4) 144(3)
N2 H3n O1 1_545 0.878(18) 2.183(18) 2.985(4) 152(3)
N3 H4n O3 1_565 0.883(14) 2.015(12) 2.892(4) 172(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24744786
