#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2011376.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_2011376
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_volume                  56
_journal_year                    2000
_chemical_formula_moiety         'C5 H10 N2 O2 '
_chemical_formula_sum            'C5 H10 N2 O2'
_chemical_formula_weight         130.15
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_cell_angle_alpha                90
_cell_angle_beta                 96.690(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.5700(10)
_cell_length_b                   9.5020(10)
_cell_length_c                   11.0320(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    296.2
_cell_measurement_theta_max      13.5
_cell_measurement_theta_min      12.8
_cell_volume                     684.02(14)
_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 .9994
_diffrn_measured_fraction_theta_max .9994
_diffrn_measurement_device_type  'Rigaku AFC-5R'
_diffrn_measurement_method       \w-2\q
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .7107
_diffrn_reflns_av_R_equivalents  .029
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            1830
_diffrn_reflns_theta_full        27.57
_diffrn_reflns_theta_max         27.57
_diffrn_standards_decay_%        .50
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .098
_exptl_absorpt_correction_T_max  .998
_exptl_absorpt_correction_T_min  .974
_exptl_absorpt_correction_type   '\y scan'
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_size_max          .20
_exptl_crystal_size_mid          .20
_exptl_crystal_size_min          .20
_refine_diff_density_max         .60
_refine_diff_density_min         -.27
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     121
_refine_ls_number_reflns         1589
_refine_ls_R_factor_gt           .0509
_refine_ls_shift/su_max          .0033
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/(\s^2^(Fo^2^) + {0.048[Max(Fo^2^,0) + 2Fc^2^]/3}^2^)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .1203
_reflns_number_gt                1077
_reflns_number_total             1589
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    qd0020.cif
_[local]_cod_data_source_block   II
_[local]_cod_cif_authors_sg_H-M  'P 21/n'
_[local]_cod_chemical_formula_sum_orig 'C5 H10 N2 O2 '
_cod_original_cell_volume        684.1(2)
_cod_database_code               2011376
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
1/2-x,1/2+y,1/2-z
-x,-y,-z
1/2+x,1/2-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_occupancy
_atom_site_type_symbol
O(1) .1713(2) .07560(10) .40070(10) .0459(4) Uani d 1.00 O
O(2) .1758(2) .08010(10) .12230(10) .0392(4) Uani d 1.00 O
N(1) .1488(3) -.1502(2) .0806(2) .0404(5) Uani d 1.00 N
N(2) .1278(3) -.1549(2) .4256(2) .0448(5) Uani d 1.00 N
C(1) .3394(3) -.0800(2) .2716(2) .0313(5) Uani d 1.00 C
C(3) .2053(3) -.0466(2) .3723(2) .0315(5) Uani d 1.00 C
C(4) .5393(3) .0029(3) .2888(2) .0453(7) Uani d 1.00 C
C(5) .6802(4) -.0347(5) .1951(3) .0760(10) Uani d 1.00 C
C(6) .2145(3) -.0436(2) .1504(2) .0292(5) Uani d 1.00 C
H(1) .193(3) -.238(3) .098(2) .056(7) Uiso calc 1.00 H
H(2) .071(3) -.132(2) .015(2) .054(7) Uiso calc 1.00 H
H(3) .041(3) -.136(2) .481(2) .049(6) Uiso calc 1.00 H
H(4) .161(4) -.238(3) .406(2) .059(7) Uiso calc 1.00 H
H(5) .367(3) -.180(2) .273(2) .028(5) Uiso calc 1.00 H
H(6) .507(3) .104(2) .286(2) .047(6) Uiso calc 1.00 H
H(7) .602(4) -.022(2) .368(2) .062(7) Uiso calc 1.00 H
H(8) .705(5) -.136(4) .196(3) .120(10) Uiso calc 1.00 H
H(9) .614(5) -.021(3) .109(3) .095(9) Uiso calc 1.00 H
H(10) .799(5) .021(3) .208(3) .082(8) Uiso calc 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) .0621(9) .0284(7) .0524(9) -.0017(7) .0285(7) -.0042(7)
O(2) .0446(8) .0263(7) .0451(8) -.0002(6) -.0009(6) .0039(6)
N(1) .0500(10) .0300(9) .0389(10) .0035(8) -.0029(8) -.0022(8)
N(2) .0620(10) .0296(10) .0480(10) .0005(9) .0279(10) -.0001(8)
C(1) .0341(10) .0284(9) .0323(10) .0040(8) .0082(7) .0010(8)
C(3) .0347(10) .0294(10) .0308(10) .0006(8) .0057(8) .0000(8)
C(4) .0320(10) .064(2) .0410(10) -.0020(10) .0041(9) .0010(10)
C(5) .0370(10) .120(3) .076(2) -.005(2) .0230(10) -.006(2)
C(6) .0268(8) .0294(10) .0332(10) .0004(8) .0111(7) .0019(8)
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)
;
N N .006 .003
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
O O .011 .006
;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(6) N(1) H(1) 1_555 1_555 121.0(10) no
C(6) N(1) H(2) 1_555 1_555 117.0(10) no
H(1) N(1) H(2) 1_555 1_555 120(2) no
C(3) N(2) H(3) 1_555 1_555 117.0(10) no
C(3) N(2) H(4) 1_555 1_555 119.0(10) no
H(3) N(2) H(4) 1_555 1_555 123(2) no
C(3) C(1) C(4) 1_555 1_555 111.3(2) no
C(3) C(1) C(6) 1_555 1_555 107.10(10) no
C(3) C(1) H(5) 1_555 1_555 108.0(10) no
C(4) C(1) C(6) 1_555 1_555 111.1(2) no
C(4) C(1) H(5) 1_555 1_555 110.0(10) no
C(6) C(1) H(5) 1_555 1_555 108.0(10) no
O(1) C(3) N(2) 1_555 1_555 122.2(2) no
O(1) C(3) C(1) 1_555 1_555 121.2(2) no
N(2) C(3) C(1) 1_555 1_555 116.6(2) no
C(1) C(4) C(5) 1_555 1_555 112.5(2) no
C(1) C(4) H(6) 1_555 1_555 109.0(10) no
C(1) C(4) H(7) 1_555 1_555 105.0(10) no
C(5) C(4) H(6) 1_555 1_555 111.0(10) no
C(5) C(4) H(7) 1_555 1_555 110(2) no
H(6) C(4) H(7) 1_555 1_555 110.0(10) no
C(4) C(5) H(8) 1_555 1_555 112(2) no
C(4) C(5) H(9) 1_555 1_555 113.0(10) no
C(4) C(5) H(10) 1_555 1_555 109.0(10) no
H(8) C(5) H(9) 1_555 1_555 98(2) no
H(8) C(5) H(10) 1_555 1_555 113(2) no
H(9) C(5) H(10) 1_555 1_555 109(2) no
O(2) C(6) N(1) 1_555 1_555 122.9(2) no
O(2) C(6) C(1) 1_555 1_555 120.7(2) no
N(1) C(6) C(1) 1_555 1_555 116.5(2) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O(1) C(3) 1.230(2) no
O(2) C(6) 1.235(2) no
N(1) C(6) 1.314(3) no
N(1) H(1) .90(3) no
N(1) H(2) .85(3) no
N(2) C(3) 1.317(3) no
N(2) H(3) .91(2) no
N(2) H(4) .86(3) no
C(1) C(3) 1.530(3) no
C(1) C(4) 1.524(3) no
C(1) C(6) 1.525(3) no
C(1) H(5) .96(2) no
C(4) C(5) 1.508(4) no
C(4) H(6) .98(2) no
C(4) H(7) .95(3) no
C(5) H(8) .98(4) no
C(5) H(9) 1.00(3) no
C(5) H(10) .96(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) H(7) 2.85(3) 3_656
O(1) N(1) 2.858(2) 2_555
O(1) N(2) 2.996(2) 3_556
O(1) H(5) 3.00(2) 2_555
O(1) H(10) 3.07(3) 1_455
O(1) H(2) 3.33(3) 2_555
O(1) H(4) 3.58(3) 3_556
O(2) H(5) 2.59(2) 2_555
O(2) H(10) 2.79(3) 1_455
O(2) N(2) 2.906(2) 2_555
O(2) N(1) 2.982(3) 3_555
O(2) H(9) 3.07(3) 3_655
O(2) C(1) 3.441(2) 2_555
O(2) H(3) 3.54(2) 2_555
O(2) H(1) 3.55(3) 2_555
O(2) H(1) 3.56(3) 3_555
N(1) H(6) 3.02(2) 2_545
N(1) H(2) 3.17(3) 3_555
N(1) H(9) 3.19(3) 3_655
N(1) H(10) 3.26(3) 1_455
N(1) H(8) 3.32(3) 1_455
N(1) H(10) 3.47(3) 3_655
N(1) H(3) 3.55(2) 4_544
N(2) H(3) 3.19(2) 3_556
N(2) H(7) 3.20(3) 3_656
N(2) H(6) 3.31(2) 2_545
N(2) H(10) 3.45(3) 1_455
N(2) H(8) 3.54(4) 4_445
N(2) H(8) 3.55(4) 1_455
N(2) H(2) 3.59(2) 4_545
C(1) H(1) 3.56(3) 2_555
C(3) H(3) 2.97(2) 3_556
C(3) H(1) 3.01(3) 2_555
C(3) H(7) 3.07(3) 3_656
C(3) H(10) 3.09(3) 1_455
C(4) H(1) 3.22(2) 2_555
C(4) H(4) 3.42(3) 2_555
C(5) H(2) 3.38(2) 3_655
C(5) H(2) 3.55(2) 1_655
C(6) H(10) 2.92(3) 1_455
C(6) H(2) 2.97(3) 3_555
C(6) H(4) 3.09(3) 2_555
C(6) H(9) 3.24(3) 3_655
C(6) H(8) 3.52(3) 1_455
H(1) H(3) 3.00(3) 4_544
H(1) H(7) 3.37(3) 2_545
H(1) H(7) 3.41(4) 4_444
H(1) H(8) 3.59(4) 1_455
H(2) H(2) 2.69(5) 3_555
H(2) H(10) 2.89(4) 3_655
H(2) H(9) 2.98(4) 3_655
H(2) H(4) 3.07(3) 4_444
H(2) H(8) 3.30(4) 1_455
H(2) H(10) 3.28(4) 1_455
H(2) H(5) 3.36(3) 4_444
H(2) H(6) 3.42(3) 2_545
H(2) H(9) 3.43(4) 1_455
H(3) H(3) 2.68(5) 3_556
H(3) H(7) 3.10(3) 3_656
H(3) H(7) 3.19(3) 1_455
H(3) H(8) 3.27(4) 4_445
H(3) H(9) 3.54(4) 4_445
H(3) H(10) 3.56(4) 1_455
H(4) H(6) 2.72(3) 2_545
H(4) H(9) 3.22(4) 4_445
H(4) H(9) 3.25(4) 2_545
H(4) H(8) 3.36(4) 4_445
H(5) H(6) 3.22(3) 2_545
H(5) H(10) 3.56(4) 2_645
H(6) H(8) 3.09(5) 2_655
H(7) H(7) 3.39(5) 3_656
H(8) H(10) 3.43(5) 2_645
H(9) H(9) 2.72(7) 3_655
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
N2 H4 O2 2_545 .85(3) 2.08(3) 2.906(2) 164(2) yes
N2 H3 O1 3_556 .90(2) 2.10(2) 2.996(2) 174.5(18) yes
N1 H1 O1 2_545 .90(3) 1.98(3) 2.859(2) 165(2) yes
N1 H2 O2 3_555 .85(2) 2.14(2) 2.982(2) 167.1(19) yes
C1 H5 O2 2_545 .967(19) 2.59(2) 3.441(2) 147.5(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(3) C(1) C(4) 1_555 1_555 1_555 1_555 48.4(2) no
O(1) C(3) C(1) C(6) 1_555 1_555 1_555 1_555 -73.1(2) no
O(2) C(6) C(1) C(3) 1_555 1_555 1_555 1_555 69.7(2) no
O(2) C(6) C(1) C(4) 1_555 1_555 1_555 1_555 -52.0(2) no
N(1) C(6) C(1) C(3) 1_555 1_555 1_555 1_555 -108.9(2) no
N(1) C(6) C(1) C(4) 1_555 1_555 1_555 1_555 129.4(2) no
N(2) C(3) C(1) C(4) 1_555 1_555 1_555 1_555 -132.1(2) no
N(2) C(3) C(1) C(6) 1_555 1_555 1_555 1_555 106.4(2) no
C(3) C(1) C(4) C(5) 1_555 1_555 1_555 1_555 176.5(2) no
C(5) C(4) C(1) C(6) 1_555 1_555 1_555 1_555 -64.3(3) no