#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/63/2206398.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_2206398
loop_
_publ_author_name
'Jing  Xiong'
'Miao-Chang Liu'
'Ji-Xin  Yuan'
_publ_section_title
;
 1-(Carboxymethyl)uracil
;
_journal_coeditor_code           CV6542
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2665
_journal_page_last               o2667
_journal_paper_doi               10.1107/S1600536805022774
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C6 H6 N2 O4'
_chemical_formula_moiety         'C6 H6 N2 O4'
_chemical_formula_sum            'C6 H6 N2 O4'
_chemical_formula_weight         170.13
_chemical_name_systematic
;
1-(Carboxymethyl)uracil
;
_space_group_IT_number           7
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P -2yc'
_symmetry_space_group_name_H-M   'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 107.093(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.0999(8)
_cell_length_b                   4.6273(8)
_cell_length_c                   15.0106(19)
_cell_measurement_reflns_used    861
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.76
_cell_measurement_theta_min      2.84
_cell_volume                     338.58(9)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 2002)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0349
_diffrn_reflns_av_sigmaI/netI    0.0274
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            3071
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         25.24
_diffrn_reflns_theta_min         2.84
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.143
_exptl_absorpt_correction_T_max  0.9829
_exptl_absorpt_correction_T_min  0.9706
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.669
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Rod
_exptl_crystal_F_000             176
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.312
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.265
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     75
_refine_ls_number_reflns         621
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.260
_refine_ls_R_factor_all          0.0675
_refine_ls_R_factor_gt           0.0659
_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)+(0.0727P)²+0.2892P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1472
_refine_ls_wR_factor_ref         0.1481
_reflns_number_gt                607
_reflns_number_total             621
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv6542.cif
_cod_data_source_block           I
_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:

'_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 c'
_cod_database_code               2206398
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, 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_type_symbol
O1 0.9156(10) 0.3732(10) 0.5139(3) 0.0398(13) Uani d . 1 O
O2 0.4403(10) 0.9587(11) 0.2833(3) 0.0396(13) Uani d . 1 O
O3 0.9652(10) 0.5312(11) 0.7798(3) 0.0373(12) Uani d . 1 O
O4 0.9946(9) 0.8467(10) 0.6727(3) 0.0341(12) Uani d D 1 O
N1 0.5691(10) 0.6351(11) 0.5402(3) 0.0252(12) Uani d . 1 N
N2 0.6688(11) 0.6708(13) 0.3997(4) 0.0292(13) Uani d D 1 N
C1 0.7309(12) 0.5479(13) 0.4864(4) 0.0246(14) Uani d . 1 C
C2 0.4686(13) 0.8753(13) 0.3631(5) 0.0275(14) Uani d . 1 C
C3 0.3159(13) 0.9613(16) 0.4239(5) 0.0297(15) Uani d . 1 C
H3 0.1790 1.1003 0.4051 0.036 Uiso calc R 1 H
C4 0.3702(12) 0.8410(14) 0.5085(5) 0.0292(15) Uani d . 1 C
H4A 0.2685 0.8998 0.5476 0.035 Uiso calc R 1 H
C5 0.6290(14) 0.5115(14) 0.6334(4) 0.0306(15) Uani d . 1 C
H5A 0.6522 0.3044 0.6290 0.037 Uiso calc R 1 H
H5B 0.4720 0.5430 0.6562 0.037 Uiso calc R 1 H
C6 0.8787(12) 0.6316(13) 0.7031(4) 0.0231(13) Uani d . 1 C
H2 0.741(14) 0.593(14) 0.362(4) 0.028 Uiso d D 1 H
H4 1.139(9) 0.873(15) 0.715(4) 0.028 Uiso d 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
O1 0.039(3) 0.037(3) 0.041(3) 0.013(2) 0.009(2) 0.007(2)
O2 0.043(3) 0.048(3) 0.030(2) 0.015(3) 0.014(2) 0.015(3)
O3 0.042(3) 0.041(3) 0.028(2) -0.009(2) 0.0091(19) 0.013(2)
O4 0.040(3) 0.032(2) 0.027(2) -0.015(2) 0.006(2) 0.003(2)
N1 0.026(3) 0.023(3) 0.027(3) -0.001(2) 0.008(2) -0.001(2)
N2 0.034(3) 0.036(3) 0.020(3) 0.008(3) 0.012(2) -0.003(2)
C1 0.019(3) 0.017(3) 0.031(3) 0.001(3) -0.002(2) -0.009(3)
C2 0.027(3) 0.021(3) 0.033(4) 0.001(3) 0.006(3) -0.002(3)
C3 0.026(3) 0.026(3) 0.038(4) 0.002(3) 0.011(3) 0.000(3)
C4 0.027(4) 0.029(3) 0.035(3) -0.010(3) 0.015(3) -0.008(3)
C5 0.039(4) 0.022(3) 0.032(3) -0.003(3) 0.012(3) 0.004(3)
C6 0.032(3) 0.017(3) 0.027(3) 0.003(3) 0.019(3) 0.007(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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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
C6 O4 H4 104(5)
C4 N1 C1 120.8(5)
C4 N1 C5 122.0(5)
C1 N1 C5 117.1(5)
C1 N2 C2 126.9(5)
C1 N2 H2 116(5)
C2 N2 H2 116(5)
O1 C1 N2 122.6(6)
O1 C1 N1 122.3(6)
N2 C1 N1 115.1(5)
O2 C2 N2 117.7(6)
O2 C2 C3 127.6(6)
N2 C2 C3 114.7(6)
C4 C3 C2 119.6(6)
C4 C3 H3 120.2
C2 C3 H3 120.2
C3 C4 N1 122.9(6)
C3 C4 H4A 118.6
N1 C4 H4A 118.6
N1 C5 C6 114.9(5)
N1 C5 H5A 108.6
C6 C5 H5A 108.6
N1 C5 H5B 108.6
C6 C5 H5B 108.6
H5A C5 H5B 107.5
O3 C6 O4 123.6(6)
O3 C6 C5 121.7(6)
O4 C6 C5 114.7(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 1.217(7) yes
O2 C2 1.227(8) yes
O3 C6 1.199(7) ?
O4 C6 1.306(7) ?
O4 H4 0.82(2) ?
N1 C4 1.371(8) yes
N1 C1 1.374(8) yes
N1 C5 1.459(8) ?
N2 C1 1.369(9) yes
N2 C2 1.382(8) yes
N2 H2 0.84(2) ?
C2 C3 1.419(10) yes
C3 C4 1.339(10) ?
C3 H3 0.9300 ?
C4 H4A 0.9300 ?
C5 C6 1.497(10) ?
C5 H5A 0.9700 ?
C5 H5B 0.9700 ?
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
O4 H4 O2 2_675 0.82(2) 1.76(3) 2.553(7) 160(7) yes
N2 H2 O3 2_564 0.84(2) 2.00(3) 2.828(7) 169(7) 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
C2 N2 C1 O1 -178.3(6)
C2 N2 C1 N1 1.9(9)
C4 N1 C1 O1 177.3(6)
C5 N1 C1 O1 0.7(9)
C4 N1 C1 N2 -2.9(8)
C5 N1 C1 N2 -179.5(5)
C1 N2 C2 O2 -179.2(7)
C1 N2 C2 C3 0.0(9)
O2 C2 C3 C4 178.1(7)
N2 C2 C3 C4 -1.0(9)
C2 C3 C4 N1 -0.1(10)
C1 N1 C4 C3 2.1(9)
C5 N1 C4 C3 178.6(6)
C4 N1 C5 C6 -101.4(7)
C1 N1 C5 C6 75.2(7)
N1 C5 C6 O3 -173.2(5)
N1 C5 C6 O4 5.4(8)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 224243
