#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/13/2011375.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_2011375
loop_
_publ_author_name
'Sakamoto, Jun'
'Nakagawa, Takashi'
'Kanehisa, Nobuko'
'Kai, Yasushi'
'Katsura, Masahiro'
_publ_section_title
;
 Methylmalonamide and ethylmalonamide
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              e411
_journal_page_last               e412
_journal_paper_doi               10.1107/S0108270100010866
_journal_volume                  56
_journal_year                    2000
_chemical_formula_moiety         'C4 H8 N2 O2'
_chemical_formula_sum            'C4 H8 N2 O2'
_chemical_formula_weight         116.12
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.778(2)
_cell_length_b                   10.879(2)
_cell_length_c                   5.706(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    296.2
_cell_measurement_theta_max      14.9
_cell_measurement_theta_min      13.8
_cell_volume                     607.0(3)
_computing_cell_refinement
;
MSC/AFC Diffractometer Control Software
;
_computing_data_collection
;
MSC/AFC Diffractometer Control Software
(Molecular Structure Corporation, 1990)
;
_computing_data_reduction
;
TEXSAN (Molecular Structure Corporation & Rigaku Corporation, 1999)
;
_computing_publication_material  TEXSAN
_computing_structure_refinement  TEXSAN
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 1.0000
_diffrn_measurement_device_type  'Rigaku AFC-5R'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .7107
_diffrn_reflns_av_R_equivalents  .000
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            854
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_standards_decay_%        3.48
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .102
_exptl_absorpt_correction_T_max  .997
_exptl_absorpt_correction_T_min  .980
_exptl_absorpt_correction_type   '\y scan'
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_size_max          .25
_exptl_crystal_size_mid          .20
_exptl_crystal_size_min          .10
_refine_diff_density_max         .35
_refine_diff_density_min         -.27
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.152
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     58
_refine_ls_number_reflns         735
_refine_ls_R_factor_gt           .0404
_refine_ls_shift/su_max          .0019
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/(σ²(Fo²) + {0.050[Max(Fo²,0) + 2Fc²]/3}²)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .1146
_reflns_number_gt                451
_reflns_number_total             735
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            qd0020.cif
_cod_data_source_block           I
_cod_original_cell_volume        607.0(2)
_cod_database_code               2011375
_cod_database_fobs_code          2011375
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
1/2+x,1/2-y,1/2-z
-x,1/2+y,-z
1/2-x,-y,1/2+z
-x,-y,-z
1/2-x,1/2+y,1/2+z
x,1/2-y,z
1/2+x,y,1/2-z
loop_
_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
_atom_site_type_symbol
O(1) .92580(10) .10580(10) .2067(2) .0596(4) Uani d . 1.00 . . O
N(1) 1.14960(10) .0804(2) .1445(3) .0494(4) Uani d . 1.00 . . N
C(1) 1.0771(3) .2500 .3921(4) .0418(6) Uani d S 1.00 . . C
C(2) 1.04520(10) .1379(2) .2414(3) .0402(4) Uani d . 1.00 . . C
C(3) .9925(4) .2500 .6160(5) .0629(10) Uani d S 1.00 . . C
H(1) 1.238(2) .102(2) .170(4) .068(6) Uiso calc . 1.00 . . H
H(2) 1.131(2) .012(2) .041(3) .058(5) Uiso calc . 1.00 . . H
H(3) 1.172(2) .2500 .423(4) .031(6) Uiso calc S 1.00 . . H
H(4) 1.020(2) .179(2) .703(4) .090(8) Uiso calc . 1.00 . . H
H(5) .899(4) .2500 .571(6) .080(10) Uiso calc S 1.00 . . H
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
O(1) .0284(6) .0761(10) .0741(9) -.0074(6) .0034(6) -.0253(7)
N(1) .0288(8) .0556(9) .0637(9) .0012(7) -.0029(7) -.0114(8)
C(1) .0350(10) .0500(10) .0410(10) .0000 -.0080(10) .0000
C(2) .0305(7) .0487(9) .0413(8) -.0015(7) -.0026(6) .0021(8)
C(3) .085(2) .069(2) .0350(10) .0000 .0000(10) .0000
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .003 .002
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
H H .000 .000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
O O .011 .006
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
N N .006 .003
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C(2) N(1) H(1) 1_555 1_555 123.0(10) no
C(2) N(1) H(2) 1_555 1_555 118.0(10) no
H(1) N(1) H(2) 1_555 1_555 118.0(10) no
C(2) C(1) C(2) 1_555 7_555 106.2(2) no
C(2) C(1) C(3) 1_555 1_555 111.30(10) no
C(2) C(1) H(3) 1_555 1_555 107.8(7) no
C(2) C(1) C(3) 7_555 1_555 111.30(10) no
C(2) C(1) H(3) 7_555 1_555 107.8(7) no
C(3) C(1) H(3) 1_555 1_555 112.0(10) no
O(1) C(2) N(1) 1_555 1_555 122.1(2) no
O(1) C(2) C(1) 1_555 1_555 120.7(2) no
N(1) C(2) C(1) 1_555 1_555 117.2(2) no
C(1) C(3) H(4) 1_555 1_555 106.0(10) no
C(1) C(3) H(4) 1_555 7_555 106.0(10) no
C(1) C(3) H(5) 1_555 1_555 107(2) no
H(4) C(3) H(4) 1_555 7_555 108(2) no
H(4) C(3) H(5) 1_555 1_555 114.0(10) no
H(4) C(3) H(5) 7_555 1_555 114.0(10) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O(1) C(2) . . 1.235(2) no
N(1) C(2) . . 1.319(2) no
N(1) H(1) . . .90(2) no
N(1) H(2) . . .96(2) no
C(1) C(2) . . 1.524(2) no
C(1) C(2) . 7_555 1.524(2) no
C(1) C(3) . . 1.522(4) no
C(1) H(3) . . .95(2) no
C(3) H(4) . . .96(3) no
C(3) H(4) . 7_555 .96(3) no
C(3) H(5) . . .95(3) no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
O(1) N(1) 2.844(2) 8_455
O(1) N(1) 2.943(2) 5_755
O(1) H(3) 3.02(2) 2_455
O(1) H(4) 3.12(2) 1_554
O(1) H(4) 3.18(3) 5_756
O(1) H(2) 3.38(2) 8_455
O(1) H(1) 3.50(2) 5_755
N(1) H(4) 3.02(2) 1_554
N(1) H(2) 3.11(2) 5_755
N(1) H(2) 3.28(2) 4_755
N(1) H(5) 3.30(3) 2_555
N(1) H(4) 3.38(3) 5_756
N(1) H(1) 3.53(2) 4_754
C(2) H(2) 2.87(2) 5_755
C(2) H(1) 3.07(2) 8_455
C(2) H(4) 3.12(2) 1_554
C(2) H(4) 3.52(3) 5_756
C(3) H(1) 3.39(2) 2_455
C(3) H(1) 3.39(2) 8_455
H(1) H(5) 2.64(3) 2_555
H(1) H(2) 2.77(3) 4_755
H(1) H(4) 3.52(3) 1_554
H(1) H(4) 3.58(3) 8_555
H(2) H(2) 2.62(4) 5_755
H(2) H(4) 2.86(3) 1_554
H(2) H(4) 2.94(3) 5_756
H(2) H(3) 3.50(2) 4_754
H(3) H(5) 3.59(4) 2_555
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
_geom_hbond_publ_flag
N1 H1 O1 8_555 .91(2) 1.97(2) 2.8445(18) 162(2) yes
N1 H2 O1 5_755 .97(2) 1.987(19) 2.943(2) 169.4(17) yes
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
O(1) C(2) C(1) C(2) 1_555 1_555 1_555 7_555 -76.0(2) no
O(1) C(2) C(1) C(3) 1_555 1_555 1_555 1_555 45.3(3) no
N(1) C(2) C(1) C(2) 1_555 1_555 1_555 7_555 101.7(2) no
N(1) C(2) C(1) C(3) 1_555 1_555 1_555 1_555 -137.0(2) no
