#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:03:29 +0200 (vie 13 de oct de 2017) $
#$Revision: 201974 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/24/2212493.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_2212493
loop_
_publ_author_name
'Li, Jian'
'Liang, Zu-Pei'
'Guo, Huan-Mei'
_publ_section_title
;
 1-(1,3-Dioxoisoindolin-2-yl)urea
;
_journal_coeditor_code           BT2274
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1467
_journal_page_last               o1468
_journal_paper_doi               10.1107/S1600536807008252
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C9 H7 N3 O3'
_chemical_formula_moiety         'C9 H7 N3 O3'
_chemical_formula_sum            'C9 H7 N3 O3'
_chemical_formula_weight         205.18
_chemical_name_systematic
;
1-(1,3-dioxoisoindolin-2-yl)urea
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 96.025(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.408(3)
_cell_length_b                   4.596(2)
_cell_length_c                   27.805(13)
_cell_measurement_reflns_used    1179
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      22.82
_cell_measurement_theta_min      2.95
_cell_volume                     941.5(7)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART CCD 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  0.0601
_diffrn_reflns_av_sigmaI/netI    0.0681
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            4518
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         1.47
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  0.9867
_exptl_absorpt_correction_T_min  0.9757
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.243
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1668
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.1061
_refine_ls_R_factor_gt           0.0663
_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)+(0.063P)²+1.4756P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1629
_refine_ls_wR_factor_ref         0.1888
_reflns_number_gt                1092
_reflns_number_total             1668
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt2274.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_cell_volume        941.4(7)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2212493
_cod_database_fobs_code          2212493
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_refinement_flags
_atom_site_occupancy
O O1 1.1057(4) 0.3061(8) 0.17262(12) 0.0655(10) Uani d . 1
O O2 0.6541(4) 0.3588(7) 0.04596(10) 0.0572(9) Uani d . 1
O O3 1.1285(4) 0.5715(6) 0.05753(10) 0.0468(8) Uani d . 1
N N1 0.8964(4) 0.2675(7) 0.10444(12) 0.0404(9) Uani d . 1
N N2 1.0080(5) 0.1317(7) 0.07440(13) 0.0489(10) Uani d . 1
H H2 1.0022 -0.0529 0.0694 0.059 Uiso calc R 1
N N3 1.2421(4) 0.1570(7) 0.02742(12) 0.0428(9) Uani d D 1
H H3A 1.2349 -0.0365 0.0234 0.051 Uiso d RD 1
H H3B 1.3176 0.2449 0.0089 0.051 Uiso d RD 1
C C1 0.9591(5) 0.3669(9) 0.15122(15) 0.0405(10) Uani d . 1
C C2 0.8113(5) 0.5564(9) 0.16609(14) 0.0369(9) Uani d . 1
C C3 0.7971(6) 0.7015(10) 0.20928(16) 0.0504(11) Uani d . 1
H H3 0.8886 0.6902 0.2348 0.060 Uiso calc R 1
C C4 0.6420(7) 0.8634(11) 0.21303(18) 0.0614(13) Uani d . 1
H H4 0.6297 0.9648 0.2414 0.074 Uiso calc R 1
C C5 0.5035(7) 0.8777(11) 0.1750(2) 0.0615(14) Uani d . 1
H H5 0.4003 0.9877 0.1785 0.074 Uiso calc R 1
C C6 0.5173(6) 0.7293(10) 0.13169(18) 0.0535(12) Uani d . 1
H H6 0.4250 0.7384 0.1063 0.064 Uiso calc R 1
C C7 0.6732(5) 0.5681(9) 0.12782(14) 0.0374(9) Uani d . 1
C C8 0.7293(5) 0.3928(9) 0.08660(15) 0.0391(10) Uani d . 1
C C9 1.1284(5) 0.3030(8) 0.05290(13) 0.0329(9) Uani d . 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
O1 0.0468(19) 0.083(3) 0.065(2) 0.0237(18) -0.0042(16) 0.0078(18)
O2 0.0553(19) 0.070(2) 0.0442(18) -0.0088(17) -0.0020(15) -0.0043(16)
O3 0.0602(19) 0.0194(14) 0.0618(19) 0.0010(14) 0.0116(15) -0.0032(13)
N1 0.0376(19) 0.0373(19) 0.047(2) 0.0050(15) 0.0076(16) -0.0025(16)
N2 0.057(2) 0.0242(18) 0.070(2) -0.0030(17) 0.0281(19) -0.0077(17)
N3 0.049(2) 0.0248(17) 0.057(2) 0.0023(16) 0.0164(17) -0.0031(16)
C1 0.037(2) 0.039(2) 0.045(2) 0.0082(19) 0.0019(19) 0.0046(19)
C2 0.032(2) 0.036(2) 0.043(2) -0.0014(18) 0.0046(17) 0.0011(18)
C3 0.049(3) 0.059(3) 0.043(2) -0.001(2) 0.004(2) -0.006(2)
C4 0.071(3) 0.056(3) 0.060(3) 0.006(3) 0.023(3) -0.012(2)
C5 0.050(3) 0.054(3) 0.085(4) 0.013(2) 0.030(3) 0.004(3)
C6 0.038(2) 0.056(3) 0.066(3) 0.007(2) 0.003(2) 0.006(2)
C7 0.034(2) 0.036(2) 0.043(2) 0.0023(18) 0.0065(18) 0.0027(18)
C8 0.038(2) 0.035(2) 0.044(2) -0.0099(18) 0.0015(19) 0.0057(18)
C9 0.036(2) 0.023(2) 0.039(2) 0.0008(17) -0.0036(17) -0.0021(17)
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
N2 N1 C8 122.1(3)
N2 N1 C1 122.9(3)
C8 N1 C1 112.7(3)
C9 N2 N1 117.4(3)
C9 N2 H2 121.3
N1 N2 H2 121.3
C9 N3 H3A 122.1
C9 N3 H3B 123.0
H3A N3 H3B 114.0
O1 C1 N1 124.7(4)
O1 C1 C2 130.0(4)
N1 C1 C2 105.3(3)
C3 C2 C7 121.7(4)
C3 C2 C1 130.2(4)
C7 C2 C1 108.2(3)
C4 C3 C2 117.6(4)
C4 C3 H3 121.2
C2 C3 H3 121.2
C3 C4 C5 121.3(4)
C3 C4 H4 119.4
C5 C4 H4 119.4
C4 C5 C6 121.0(4)
C4 C5 H5 119.5
C6 C5 H5 119.5
C7 C6 C5 117.7(4)
C7 C6 H6 121.1
C5 C6 H6 121.1
C6 C7 C2 120.7(4)
C6 C7 C8 130.4(4)
C2 C7 C8 108.8(3)
O2 C8 N1 125.1(4)
O2 C8 C7 130.1(4)
N1 C8 C7 104.8(3)
O3 C9 N3 124.1(4)
O3 C9 N2 121.3(4)
N3 C9 N2 114.7(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.214(5)
O2 C8 1.217(5)
O3 C9 1.241(4)
N1 N2 1.384(4)
N1 C8 1.407(5)
N1 C1 1.411(5)
N2 C9 1.372(5)
N2 H2 0.8600
N3 C9 1.337(5)
N3 H3A 0.8973
N3 H3B 0.8963
C1 C2 1.492(5)
C2 C3 1.387(6)
C2 C7 1.397(5)
C3 C4 1.382(6)
C3 H3 0.9300
C4 C5 1.396(7)
C4 H4 0.9300
C5 C6 1.397(7)
C5 H5 0.9300
C6 C7 1.386(6)
C6 H6 0.9300
C7 C8 1.495(6)
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
N2 H2 O3 1_545 0.86 2.01 2.781(4) 149.1
N3 H3A O3 1_545 0.90 2.22 2.966(4) 140.3
N3 H3A O2 3_755 0.90 2.63 3.271(5) 129.1
N3 H3B O2 3_765 0.90 2.40 3.168(5) 144.1
N3 H3B O2 1_655 0.90 2.65 3.179(5) 118.9
C6 H6 O3 1_455 0.93 2.57 3.439(6) 154.8
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
C8 N1 N2 C9 86.6(5)
C1 N1 N2 C9 -74.4(5)
N2 N1 C1 O1 -11.9(6)
C8 N1 C1 O1 -174.4(4)
N2 N1 C1 C2 167.2(3)
C8 N1 C1 C2 4.6(4)
O1 C1 C2 C3 -3.9(8)
N1 C1 C2 C3 177.1(4)
O1 C1 C2 C7 177.2(4)
N1 C1 C2 C7 -1.8(4)
C7 C2 C3 C4 -1.0(7)
C1 C2 C3 C4 -179.9(4)
C2 C3 C4 C5 0.8(7)
C3 C4 C5 C6 -0.2(8)
C4 C5 C6 C7 -0.1(7)
C5 C6 C7 C2 -0.1(7)
C5 C6 C7 C8 -178.7(4)
C3 C2 C7 C6 0.7(6)
C1 C2 C7 C6 179.8(4)
C3 C2 C7 C8 179.6(4)
C1 C2 C7 C8 -1.4(4)
N2 N1 C8 O2 11.6(6)
C1 N1 C8 O2 174.3(4)
N2 N1 C8 C7 -168.1(3)
C1 N1 C8 C7 -5.4(4)
C6 C7 C8 O2 3.1(7)
C2 C7 C8 O2 -175.6(4)
C6 C7 C8 N1 -177.3(4)
C2 C7 C8 N1 4.0(4)
N1 N2 C9 O3 -4.9(6)
N1 N2 C9 N3 175.0(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2711799
