#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:08:28 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201955 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/88/2008855.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_2008855
loop_
_publ_author_name
'Xiang-Jun Zheng'
'Zhe-Ming Wang'
'Yan-Qia Wang'
'Lin-Pei Jin'
'Jian-Quan Guo'
'Chun-Hua Yan'
_publ_section_title
;
 N,N-Bis(2-oxopyrrolidin-1-ylmethyl)glycine
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1333
_journal_page_last               1335
_journal_paper_doi               10.1107/S0108270199005259
_journal_volume                  55
_journal_year                    1999
_chemical_formula_sum            'C12 H19 N3 O4'
_chemical_formula_weight         269.30
_chemical_melting_point          144.5(5)
_chemical_name_systematic        N,N-bis(N-methylene-2-pyrrolidone)glycine
_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'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.852(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.7310(6)
_cell_length_b                   9.1357(5)
_cell_length_c                   10.8227(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13.56
_cell_measurement_theta_min      9.98
_cell_volume                     1341.45(11)
_computing_cell_refinement       'Nonius CAD4 Argus'
_computing_data_collection       'Nonius CAD4 Argus (Nonius B. V., 1996)'
_computing_data_reduction        'MoLEN (Fair, 1990)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1990)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Nonius CAD4 MACH3'
_diffrn_measurement_method       θ/2θ
_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  0.0117
_diffrn_reflns_av_sigmaI/netI    0.0269
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3097
_diffrn_reflns_theta_full        27.04
_diffrn_reflns_theta_max         27.04
_diffrn_reflns_theta_min         1.50
_diffrn_standards_decay_%        3.3
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.145
_refine_ls_extinction_coef       0.0053(15)
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         2936
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0784
_refine_ls_R_factor_gt           0.0445
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w =1/[σ²(Fo²)+(0.0537P)²+0.2819P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1193
_reflns_number_gt                2072
_reflns_number_total             2936
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ta1237.cif
_cod_data_source_block           last
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_chemical_melting_point' value '144-145' was changed to '144.5(5)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_chemical_melting_point' value '144-145' was changed to '144.5(5)' -
the average value was taken and precision was
estimated.

'_symmetry_cell_setting' value 'Monoclinic' changed to
'monoclinic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2008855
_cod_database_fobs_code          2008855
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_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
O1 -0.00045(9) 0.22257(17) -0.09390(14) 0.0650(4) Uani d . 1 . . O
O2 0.14939(9) 0.25062(15) -0.14576(13) 0.0602(4) Uani d . 1 . . O
O3 0.49610(10) 0.17338(16) 0.03127(12) 0.0596(4) Uani d . 1 . . O
O4 0.09350(10) -0.14065(15) -0.21300(13) 0.0635(4) Uani d . 1 . . O
N1 0.22933(9) 0.05862(15) 0.05572(12) 0.0401(3) Uani d . 1 . . N
N2 0.38809(9) 0.11883(16) 0.16604(12) 0.0435(3) Uani d . 1 . . N
N3 0.21399(10) -0.17481(16) -0.04666(13) 0.0448(4) Uani d . 1 . . N
C1 0.09560(12) 0.20081(19) -0.07886(16) 0.0448(4) Uani d . 1 . . C
C2 0.12716(12) 0.1048(2) 0.03473(16) 0.0422(4) Uani d . 1 . . C
C3 0.29932(13) 0.1762(2) 0.09423(19) 0.0488(4) Uani d . 1 . . C
C4 0.47739(12) 0.11864(19) 0.12778(15) 0.0425(4) Uani d . 1 . . C
C5 0.54802(14) 0.0371(3) 0.22428(17) 0.0562(5) Uani d . 1 . . C
C6 0.49608(16) 0.0274(3) 0.33642(18) 0.0626(6) Uani d . 1 . . C
C7 0.38747(15) 0.0420(3) 0.28367(18) 0.0572(5) Uani d . 1 . . C
C8 0.25691(12) -0.0301(2) -0.04432(16) 0.0433(4) Uani d . 1 . . C
C9 0.13888(13) -0.2204(2) -0.13170(17) 0.0493(4) Uani d . 1 . . C
C10 0.1211(2) -0.3795(3) -0.1128(3) 0.0724(6) Uani d . 1 . . C
C11 0.1911(2) -0.4214(3) 0.0032(3) 0.0758(7) Uani d . 1 . . C
C12 0.2517(2) -0.2864(3) 0.0439(3) 0.0730(7) Uani d . 1 . . C
H1 -0.0209(18) 0.275(3) -0.166(2) 0.093(8) Uiso d . 1 . . H
H2 0.0862(12) 0.017(2) 0.0232(16) 0.044(5) Uiso d . 1 . . H
H3 0.1100(13) 0.155(2) 0.1062(18) 0.050(5) Uiso d . 1 . . H
H4 0.2656(15) 0.245(2) 0.1440(19) 0.063(6) Uiso d . 1 . . H
H5 0.3219(13) 0.229(2) 0.0233(18) 0.053(5) Uiso d . 1 . . H
H6 0.5588(16) -0.060(3) 0.188(2) 0.078(7) Uiso d . 1 . . H
H7 0.6112(17) 0.089(2) 0.243(2) 0.075(7) Uiso d . 1 . . H
H8 0.5069(18) -0.065(3) 0.384(2) 0.089(8) Uiso d . 1 . . H
H9 0.515(2) 0.120(3) 0.394(3) 0.112(9) Uiso d . 1 . . H
H10 0.3529(18) -0.051(3) 0.267(2) 0.090(8) Uiso d . 1 . . H
H11 0.3510(17) 0.098(3) 0.337(2) 0.085(8) Uiso d . 1 . . H
H12 0.2395(13) 0.017(2) -0.1259(17) 0.047(5) Uiso d . 1 . . H
H13 0.3287(12) -0.0408(18) -0.0308(15) 0.039(4) Uiso d . 1 . . H
H14 0.1321(19) -0.432(3) -0.186(3) 0.099(9) Uiso d . 1 . . H
H15 0.051(2) -0.389(3) -0.105(3) 0.115(10) Uiso d . 1 . . H
H16 0.2365(17) -0.500(3) -0.012(2) 0.087(7) Uiso d . 1 . . H
H17 0.1541(19) -0.444(3) 0.063(3) 0.093(9) Uiso d . 1 . . H
H18 0.322(2) -0.298(3) 0.036(3) 0.113(10) Uiso d . 1 . . H
H19 0.2462(19) -0.254(3) 0.124(3) 0.096(9) Uiso d . 1 . . H
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_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
2 3 1
-3 -2 -3
0 -2 2
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
C1 O1 H1 110.4(16) ?
C8 N1 C2 113.83(13) y
C8 N1 C3 112.89(14) y
C2 N1 C3 114.18(14) y
C4 N2 C3 124.54(15) y
C4 N2 C7 113.25(15) y
C3 N2 C7 121.97(15) y
C9 N3 C8 124.41(15) y
C9 N3 C12 113.72(17) y
C8 N3 C12 121.85(15) y
O2 C1 O1 124.39(16) y
O2 C1 C2 125.58(15) y
O1 C1 C2 110.03(15) y
N1 C2 C1 116.37(14) y
N1 C2 H2 107.7(10) ?
C1 C2 H2 106.6(10) ?
N1 C2 H3 111.4(11) ?
C1 C2 H3 107.6(11) ?
H2 C2 H3 106.7(15) ?
N2 C3 N1 110.61(15) y
N2 C3 H4 111.5(12) ?
N1 C3 H4 106.3(12) ?
N2 C3 H5 104.7(11) ?
N1 C3 H5 113.9(11) ?
H4 C3 H5 109.9(16) ?
O3 C4 N2 125.55(16) y
O3 C4 C5 126.68(17) y
N2 C4 C5 107.77(15) y
C6 C5 C4 104.72(16) y
C6 C5 H6 112.4(14) ?
C4 C5 H6 106.9(13) ?
C6 C5 H7 112.4(13) ?
C4 C5 H7 110.8(13) ?
H6 C5 H7 109.4(18) ?
C5 C6 C7 104.60(16) y
C5 C6 H8 114.9(15) ?
C7 C6 H8 109.3(15) ?
C5 C6 H9 109.1(15) ?
C7 C6 H9 106.9(15) ?
H8 C6 H9 112(2) ?
N2 C7 C6 103.50(16) y
N2 C7 H10 109.0(15) ?
C6 C7 H10 114.6(15) ?
N2 C7 H11 109.9(15) ?
C6 C7 H11 113.1(14) ?
H10 C7 H11 107(2) ?
N3 C8 N1 111.83(14) y
N3 C8 H12 109.9(10) ?
N1 C8 H12 112.1(11) ?
N3 C8 H13 108.0(10) ?
N1 C8 H13 108.5(10) ?
H12 C8 H13 106.2(14) ?
O4 C9 N3 123.87(18) y
O4 C9 C10 126.64(18) y
N3 C9 C10 109.49(18) y
C9 C10 C11 105.29(19) y
C9 C10 H14 108.7(17) ?
C11 C10 H14 113.6(16) ?
C9 C10 H15 106.3(18) ?
C11 C10 H15 114.7(18) ?
H14 C10 H15 108(2) ?
C10 C11 C12 106.68(19) y
C10 C11 H16 112.7(15) ?
C12 C11 H16 108.0(14) ?
C10 C11 H17 107.2(17) ?
C12 C11 H17 108.7(17) ?
H16 C11 H17 113(2) ?
N3 C12 C11 104.63(18) y
N3 C12 H18 105.5(17) ?
C11 C12 H18 112.6(18) ?
N3 C12 H19 109.6(17) ?
C11 C12 H19 114.2(17) ?
H18 C12 H19 110(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . 1.319(2) y
O1 H1 . 0.93(3) ?
O2 C1 . 1.201(2) y
O3 C4 . 1.220(2) y
O4 C9 . 1.235(2) y
N1 C8 . 1.449(2) y
N1 C2 . 1.4491(19) y
N1 C3 . 1.459(2) y
N2 C4 . 1.353(2) y
N2 C3 . 1.440(2) y
N2 C7 . 1.455(2) y
N3 C9 . 1.339(2) y
N3 C8 . 1.446(2) y
N3 C12 . 1.453(3) y
C1 C2 . 1.518(2) y
C2 H2 . 0.979(18) ?
C2 H3 . 0.958(19) ?
C3 H4 . 0.99(2) ?
C3 H5 . 1.00(2) ?
C4 C5 . 1.508(3) y
C5 C6 . 1.502(3) y
C5 H6 . 0.99(2) ?
C5 H7 . 0.98(2) ?
C6 C7 . 1.519(3) y
C6 H8 . 0.99(3) ?
C6 H9 . 1.06(3) ?
C7 H10 . 0.97(3) ?
C7 H11 . 0.96(2) ?
C8 H12 . 0.977(19) ?
C8 H13 . 0.978(17) ?
C9 C10 . 1.494(3) y
C10 C11 . 1.508(4) y
C10 H14 . 0.95(3) ?
C10 H15 . 0.98(3) ?
C11 C12 . 1.514(4) y
C11 H16 . 0.98(2) ?
C11 H17 . 0.91(3) ?
C12 H18 . 0.98(3) ?
C12 H19 . 0.93(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
O1 H1 O4 2_554 0.93(3) 1.70(3) 2.5961(18) 162(2)
C6 H8 O3 2_645 0.99(3) 2.56(3) 3.532(3) 167(2)
C6 H9 O3 4_566 1.06(3) 2.44(3) 3.453(3) 160(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
N1 C2 C1 O1 173.75(15)
N1 C2 C1 O2 -6.4(3)
C3 N1 C2 C1 69.8(2)
N2 C3 N1 C2 153.67(15)
C4 N2 C3 N1 112.91(19)
O3 C4 N2 C3 4.1(3)
C5 C4 N2 C3 -174.95(17)
C6 C5 C4 N2 -14.9(2)
C7 N2 C3 N1 -61.1(2)
C7 C6 C5 C4 23.6(2)
C8 N1 C2 C1 -61.9(2)
C9 N3 C8 N1 106.33(18)
O4 C9 N3 C8 -5.0(3)
C10 C9 N3 C8 174.27(18)
C11 C10 C9 N3 4.5(3)
C12 N3 C8 N1 -75.3(2)
C12 C11 C10 C9 -3.1(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21105755
