#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/13/2231307.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_2231307
loop_
_publ_author_name
'Seuring, Jan'
'Agarwal, Seema'
'Harms, Klaus'
_publ_section_title
;
 N-Acryloyl glycinamide
;
_journal_coeditor_code           SJ5179
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2170
_journal_paper_doi               10.1107/S1600536811029758
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C5 H8 N2 O2'
_chemical_formula_moiety         'C5 H8 N2 O2'
_chemical_formula_sum            'C5 H8 N2 O2'
_chemical_formula_weight         128.13
_chemical_melting_point          143
_chemical_name_common            N-Acryloylglycinamide
_chemical_name_systematic
;
N-(Carbamoylmethyl)prop-2-enamide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 98.109(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.938(2)
_cell_length_b                   4.8055(4)
_cell_length_c                   8.4920(12)
_cell_measurement_reflns_used    7769
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27
_cell_measurement_theta_min      2.6
_cell_volume                     643.90(13)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2006)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2006)'
_computing_data_reduction        'X-AREA (Stoe & Cie, 2006)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2007)'
_computing_publication_material
'publCIF (Westrip, 2010), PLATON (Spek, 2009) and WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Stoe IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_av_sigmaI/netI    0.0337
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6001
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.78
_diffrn_reflns_theta_min         2.58
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.9967
_exptl_absorpt_correction_T_min  0.9907
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED; Stoe & Cie, 2006)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.152
_refine_ls_extinction_coef       0.032(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   0.974
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     115
_refine_ls_number_reflns         1362
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.974
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0323
_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)+(0.0548P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0802
_refine_ls_wR_factor_ref         0.0846
_reflns_number_gt                1065
_reflns_number_total             1362
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj5179.cif
_cod_data_source_block           I
_cod_original_cell_volume        643.91(14)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2231307
_cod_database_fobs_code          2231307
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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
_atom_site_symmetry_multiplicity
C C1 0.91738(9) 0.4644(3) 0.66968(16) 0.0334(3) Uani d 1 1
C C2 0.87077(8) 0.6065(3) 0.75755(15) 0.0269(3) Uani d 1 1
C C3 0.80276(7) 0.4732(3) 0.83438(13) 0.0218(3) Uani d 1 1
C C6 0.68733(7) 0.5421(3) 0.98560(13) 0.0229(3) Uani d 1 1
C C7 0.61296(7) 0.4355(3) 0.86952(13) 0.0209(3) Uani d 1 1
N N5 0.75513(6) 0.6473(2) 0.90665(12) 0.0221(3) Uani d 1 1
N N8 0.56460(7) 0.2477(2) 0.92691(12) 0.0271(3) Uani d 1 1
O O4 0.79110(6) 0.21891(18) 0.83202(10) 0.0280(2) Uani d 1 1
O O9 0.59828(5) 0.52628(19) 0.73164(9) 0.0248(2) Uani d 1 1
H H1A 0.9069(10) 0.273(4) 0.6562(19) 0.038(4) Uiso d 1 1
H H1B 0.9623(10) 0.553(4) 0.620(2) 0.041(4) Uiso d 1 1
H H2 0.8770(10) 0.802(4) 0.7774(18) 0.036(4) Uiso d 1 1
H H5 0.7628(10) 0.822(4) 0.8996(19) 0.034(4) Uiso d 1 1
H H6A 0.7081(8) 0.395(3) 1.0551(17) 0.023(3) Uiso d 1 1
H H6B 0.6661(9) 0.697(3) 1.0471(17) 0.025(3) Uiso d 1 1
H H8A 0.5799(10) 0.181(4) 1.029(2) 0.042(4) Uiso d 1 1
H H8B 0.5176(11) 0.194(4) 0.867(2) 0.040(4) Uiso d 1 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
C1 0.0316(7) 0.0359(8) 0.0336(7) 0.0022(6) 0.0078(5) 0.0017(6)
C2 0.0260(6) 0.0247(7) 0.0300(6) -0.0003(5) 0.0039(5) 0.0015(5)
C3 0.0246(6) 0.0198(6) 0.0201(5) 0.0000(5) 0.0001(4) 0.0001(4)
C6 0.0261(6) 0.0237(6) 0.0189(6) -0.0002(5) 0.0028(4) -0.0010(5)
C7 0.0231(6) 0.0211(6) 0.0193(5) 0.0030(5) 0.0058(4) -0.0008(4)
N5 0.0244(5) 0.0177(6) 0.0246(5) -0.0012(4) 0.0040(4) -0.0010(4)
N8 0.0286(5) 0.0318(7) 0.0204(5) -0.0076(4) 0.0020(4) 0.0030(4)
O4 0.0361(5) 0.0180(5) 0.0304(5) -0.0008(4) 0.0065(4) -0.0011(4)
O9 0.0273(4) 0.0291(5) 0.0178(4) 0.0006(4) 0.0028(3) 0.0025(3)
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
C2 C1 H1A 118.2(10)
C2 C1 H1B 121.6(10)
H1A C1 H1B 120.2(15)
C1 C2 C3 122.01(13)
C1 C2 H2 123.8(10)
C3 C2 H2 114.2(10)
O4 C3 N5 122.19(11)
O4 C3 C2 122.42(11)
N5 C3 C2 115.39(11)
N5 C6 C7 112.57(9)
N5 C6 H6A 109.3(8)
C7 C6 H6A 108.9(8)
N5 C6 H6B 108.4(8)
C7 C6 H6B 107.4(8)
H6A C6 H6B 110.1(11)
O9 C7 N8 123.05(11)
O9 C7 C6 121.30(11)
N8 C7 C6 115.62(10)
C3 N5 C6 120.42(11)
C3 N5 H5 119.2(11)
C6 N5 H5 120.2(11)
C7 N8 H8A 119.6(11)
C7 N8 H8B 118.6(11)
H8A N8 H8B 121.8(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.3160(19)
C1 H1A 0.937(18)
C1 H1B 0.981(18)
C2 C3 1.4867(17)
C2 H2 0.956(18)
C3 O4 1.2360(15)
C3 N5 1.3356(16)
C6 N5 1.4412(15)
C6 C7 1.5198(16)
C6 H6A 0.950(15)
C6 H6B 0.994(15)
C7 O9 1.2405(13)
C7 N8 1.3235(16)
N5 H5 0.850(19)
N8 H8A 0.927(18)
N8 H8B 0.881(17)
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
N5 H5 O4 1_565 0.850(19) 2.062(19) 2.8946(14) 166.3(15)
N8 H8B O9 2_646 0.881(17) 2.081(17) 2.9494(14) 168.2(15)
N8 H8A O9 4_566 0.927(18) 1.971(18) 2.8855(14) 168.6(16)
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
C1 C2 C3 O4 6.58(19)
C1 C2 C3 N5 -173.59(12)
N5 C6 C7 O9 -26.19(17)
N5 C6 C7 N8 155.59(11)
O4 C3 N5 C6 -0.03(16)
C2 C3 N5 C6 -179.87(10)
C7 C6 N5 C3 -70.81(14)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 13578531
