#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/68/2206888.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_2206888
loop_
_publ_author_name
'Nichol, Gary S.'
'Clegg, William'
_publ_section_title
;
 Malonamide: an orthorhombic polymorph
;
_journal_coeditor_code           BT6746
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3427
_journal_page_last               o3429
_journal_paper_doi               10.1107/S1600536805030540
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C3 H6 N2 O2'
_chemical_formula_moiety         'C3 H6 N2 O2'
_chemical_formula_sum            'C3 H6 N2 O2'
_chemical_formula_weight         102.10
_chemical_name_common            Malonamide
_chemical_name_systematic        Malonamide
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.3602(9)
_cell_length_b                   7.5178(8)
_cell_length_c                   11.791(2)
_cell_measurement_reflns_used    6050
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.5
_cell_volume                     475.14(12)
_computing_cell_refinement       'EvalCCD (Duisenberg et al., 2003)'
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction        EvalCCD
_computing_molecular_graphics
;
DIAMOND3 (Brandenburg & Putz, 2004) and  MERCURY (Version 1.3; Bruno et
al., 2002)
;
_computing_publication_material  'Bruker SHELXTL and local programs'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 2001)'
_diffrn_ambient_temperature      150(2)
_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'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_sigmaI/netI    0.0089
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8872
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         4.67
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_correction_T_min  0.911
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'block cut from large plate'
_exptl_crystal_F_000             216
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.196
_refine_ls_extinction_coef       0.077(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     43
_refine_ls_number_reflns         539
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.111
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0306
_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)+(0.0412P)²+0.1866P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0807
_refine_ls_wR_factor_ref         0.0829
_reflns_number_gt                490
_reflns_number_total             539
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt6746.cif
_cod_data_source_block           I
_cod_database_code               2206888
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'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_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
O 0.06613(15) 0.25831(10) 0.37641(7) 0.0222(3) Uani d . 1 O
N -0.2702(2) 0.08531(14) 0.40865(9) 0.0250(3) Uani d . 1 N
H1N -0.313(3) 0.1499(19) 0.4686(14) 0.030 Uiso d . 1 H
H2N -0.355(3) -0.005(3) 0.3895(13) 0.030 Uiso d . 1 H
C1 -0.06739(19) 0.12942(13) 0.35078(8) 0.0161(3) Uani d . 1 C
C2 0.0000 0.01335(19) 0.2500 0.0161(4) Uani d S 1 C
H2 0.136(3) -0.0629(16) 0.2721(11) 0.019 Uiso d . 1 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 0.0269(5) 0.0211(5) 0.0187(5) -0.0057(3) 0.0001(3) -0.0038(3)
N 0.0295(6) 0.0226(5) 0.0228(5) -0.0060(4) 0.0109(4) -0.0065(4)
C1 0.0200(5) 0.0152(5) 0.0131(5) 0.0013(4) -0.0008(4) 0.0014(3)
C2 0.0195(7) 0.0142(7) 0.0144(6) 0.000 0.0012(5) 0.000
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
H1N N H2N . . 120.8(15)
H1N N C1 . . 119.0(10)
H2N N C1 . . 120.1(11)
O C1 N . . 122.85(10)
O C1 C2 . . 120.12(9)
N C1 C2 . . 117.02(9)
C1 C2 C1 . 3 109.82(12)
C1 C2 H2 . . 108.1(8)
C1 C2 H2 3 . 112.0(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O C1 1.2420(13) y
N H1N 0.887(16) ?
N H2N 0.846(19) ?
N C1 1.3257(14) y
C1 C2 1.5178(13) y
C2 H2 0.963(13) ?
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
N H1N O 4_456 0.887(16) 2.058(17) 2.9282(13) 166.4(13) y
N H2N O 8 0.846(19) 2.116(19) 2.9502(14) 168.7(15) y
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_4
_geom_torsion
_geom_torsion_publ_flag
O C1 C2 C1 3 -45.99(8) y
N C1 C2 C1 3 134.54(10) y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 7623
