#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/26/2212690.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_2212690
loop_
_publ_author_name
'Sharon E. Engel'
'Gregory M. Ferrence'
_publ_section_title
;
 2-Methylpropionohydrazide
;
_journal_coeditor_code           SG2138
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1475
_journal_page_last               o1477
_journal_paper_doi               10.1107/S1600536807008896
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C4 H10 N2 O'
_chemical_formula_moiety         'C4 H10 N2 O'
_chemical_formula_sum            'C4 H10 N2 O'
_chemical_formula_weight         102.08
_chemical_name_systematic
;
2-Methylpropionohydrazide
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.0189(19)
_cell_length_b                   4.8781(9)
_cell_length_c                   21.677(4)
_cell_measurement_reflns_used    9311
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      61.037
_cell_measurement_theta_min      5.272
_cell_volume                     1165.2(4)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT-Plus
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006)'
_computing_publication_material
'WinGX (Farrugia, 1997) and publCIF (Westrip, 2007)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR2004 (Burla et al., 2005)'
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0626
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            8412
_diffrn_reflns_theta_full        30.52
_diffrn_reflns_theta_max         30.52
_diffrn_reflns_theta_min         1.88
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   '(SADABS in SAINT-Plus; Bruker, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.165
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.442
_refine_diff_density_min         -0.288
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     104
_refine_ls_number_reflns         1755
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.118
_refine_ls_R_factor_gt           0.0733
_refine_ls_shift/su_max          0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0748P)²+0.9877P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1906
_reflns_number_gt                1246
_reflns_number_total             1755
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sg2138.cif
_cod_data_source_block           I
_cod_database_code               2212690
_cod_database_fobs_code          2212690
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
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_occupancy
N N1 0.34101(18) 0.7903(4) 0.48473(8) 0.0254(4) Uani d 1
N N2 0.38704(17) 0.8527(3) 0.54404(8) 0.0244(4) Uani d 1
C C1 0.42395(19) 0.6629(4) 0.58377(10) 0.0238(4) Uani d 1
O O1 0.41985(15) 0.4143(3) 0.57242(7) 0.0290(4) Uani d 1
C C2 0.4730(2) 0.7685(4) 0.64454(10) 0.0266(5) Uani d 1
C C3 0.6052(2) 0.6864(6) 0.65061(12) 0.0348(6) Uani d 1
C C4 0.3968(2) 0.6531(5) 0.69710(11) 0.0339(5) Uani d 1
H H1A 0.292(3) 0.643(6) 0.4885(12) 0.033(7) Uiso d 1
H H1B 0.408(3) 0.734(6) 0.4627(13) 0.037(7) Uiso d 1
H H2N 0.392(2) 1.021(7) 0.5539(12) 0.032(7) Uiso d 1
H H2A 0.469(2) 0.966(6) 0.6446(10) 0.028(6) Uiso d 1
H H3A 0.611(3) 0.482(7) 0.6498(13) 0.037(7) Uiso d 1
H H3B 0.640(3) 0.748(6) 0.6876(13) 0.038(7) Uiso d 1
H H3C 0.649(3) 0.755(7) 0.6196(15) 0.048(8) Uiso d 1
H H4A 0.403(2) 0.447(6) 0.6966(12) 0.038(7) Uiso d 1
H H4B 0.426(2) 0.708(5) 0.7355(12) 0.030(6) Uiso d 1
H H4C 0.309(3) 0.696(6) 0.6935(13) 0.040(7) Uiso d 1
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
N1 0.0269(9) 0.0188(8) 0.0306(9) -0.0019(7) -0.0010(7) -0.0016(7)
N2 0.0290(9) 0.0126(8) 0.0315(9) 0.0000(7) -0.0022(7) -0.0021(6)
C1 0.0244(10) 0.0152(9) 0.0317(10) 0.0002(7) 0.0015(8) -0.0005(7)
O1 0.0377(9) 0.0113(7) 0.0380(8) 0.0000(6) -0.0036(6) -0.0019(6)
C2 0.0317(11) 0.0166(9) 0.0314(10) -0.0011(8) -0.0020(8) -0.0005(7)
C3 0.0327(13) 0.0374(14) 0.0343(12) -0.0053(10) -0.0013(10) -0.0035(10)
C4 0.0362(13) 0.0321(12) 0.0333(11) 0.0007(10) 0.0036(9) -0.0024(9)
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 0 '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 0.006 '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 N2 C1 123.28(17) y
N2 C1 O1 122.9(2) y
O1 C1 C2 121.26(19) y
N2 C1 C2 115.86(18) y
C1 C2 C3 109.18(18) y
C1 C2 C4 109.16(18) y
C3 C2 C4 111.5(2) y
C1 C2 H2A 109.0(14) ?
C3 C2 H2A 107.9(16) ?
C4 C2 H2A 110.0(14) ?
C2 C3 H3A 108.9(17) ?
C2 C3 H3B 112.4(18) ?
H3A C3 H3B 108(2) ?
C2 C3 H3C 111(2) ?
H3A C3 H3C 109(3) ?
H3B C3 H3C 108(3) ?
C2 C4 H4A 108.7(16) ?
C2 C4 H4B 112.0(16) ?
H4A C4 H4B 106(2) ?
C2 C4 H4C 113.7(16) ?
H4A C4 H4C 106(2) ?
H4B C4 H4C 110(2) ?
N2 N1 H1A 107.7(17) ?
N2 N1 H1B 104.3(17) ?
H1A N1 H1B 107(2) ?
C1 N2 H2N 119.3(19) ?
N1 N2 H2N 117.4(19) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 N2 1.415(2) y
N2 C1 1.328(3) y
C1 O1 1.238(2) y
C1 C2 1.514(3) y
C2 C3 1.516(3) y
C2 C4 1.523(3) y
N1 H1A 0.90(3) ?
N1 H1B 0.92(3) ?
N2 H2N 0.85(3) ?
C2 H2A 0.96(3) ?
C3 H3A 1.00(3) ?
C3 H3B 0.94(3) ?
C3 H3C 0.89(3) ?
C4 H4A 1.01(3) ?
C4 H4B 0.93(3) ?
C4 H4C 1.00(3) ?
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
N2 H2N O1 1_565 0.85(3) 1.98(3) 2.831(2) 175(3)
N1 H1B O1 5_666 0.92(3) 2.17(3) 3.078(3) 169(2)
N1 H1A N1 7_655 0.90(3) 2.26(3) 3.158(3) 172(2)
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
O1 C1 C2 C3 62.2(3)
N2 C1 C2 C3 -117.4(2)
O1 C1 C2 C4 -60.0(3)
N2 C1 C2 C4 120.4(2)
O1 C1 N2 N1 -0.9(3)
C2 C1 N2 N1 178.73(18)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 18154
