#------------------------------------------------------------------------------
#$Date: 2016-02-20 04:06:23 +0100 (Sat 20 de Feb de 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/24/2202439.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_2202439
loop_
_publ_author_name
'Moreno-Fuquen, Rodolfo'
'Valencia, Hoover'
'Abonia, Rodrigo'
'Kennedy, Alan R.'
'Graham Duncan'
_publ_section_title
;
 p-Nitrophenylmaleimide
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1717
_journal_page_last               o1718
_journal_paper_doi               10.1107/S1600536803022426
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C10 H6 N2 O4'
_chemical_formula_moiety         'C10 H6 N2 O4'
_chemical_formula_sum            'C10 H6 N2 O4'
_chemical_formula_weight         218.17
_chemical_melting_point          436.0(10)
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 109.69(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.535(2)
_cell_length_b                   11.624(3)
_cell_length_c                   8.148(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      16
_cell_measurement_theta_min      8
_cell_volume                     939.5(4)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction        'CAD-4 SDP (Frenz, 1978)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.00
_diffrn_measured_fraction_theta_max 0.99
_diffrn_measurement_device_type  'Enraf-Nonius CAD-4'
_diffrn_measurement_method       ω/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  0.0166
_diffrn_reflns_av_sigmaI/netI    0.0106
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            870
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_min         2.70
_diffrn_standards_decay_%        1.2
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.201
_refine_ls_extinction_coef       0.0169(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     76
_refine_ls_number_reflns         824
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0302
_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)+(0.0429P)²+0.4529P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0815
_refine_ls_wR_factor_ref         0.0845
_reflns_number_gt                738
_reflns_number_total             824
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cf6281.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2202439
_cod_database_fobs_code          2202439
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
N1 0.5000 0.21145(13) 0.2500 0.0394(4) Uani d S 1 . . N
N2 0.5000 -0.27159(14) 0.2500 0.0426(4) Uani d S 1 . . N
C4 0.5000 0.08902(15) 0.2500 0.0345(4) Uani d S 1 . . C
C1 0.5000 -0.14578(15) 0.2500 0.0359(4) Uani d S 1 . . C
C3 0.39783(13) 0.03000(11) 0.12627(18) 0.0407(4) Uani d . 1 . . C
H3 0.3294 0.0703 0.0438 0.049 Uiso calc R 1 . . H
O2 0.43544(12) -0.32156(9) 0.11594(15) 0.0611(4) Uani d . 1 . . O
C2 0.39760(13) -0.08862(12) 0.12539(17) 0.0405(4) Uani d . 1 . . C
H2 0.3297 -0.1292 0.0424 0.049 Uiso calc R 1 . . H
O1 0.27411(10) 0.24654(10) 0.20227(15) 0.0572(4) Uani d . 1 . . O
C5 0.38614(15) 0.28100(12) 0.22655(18) 0.0441(4) Uani d . 1 . . C
C6 0.43556(17) 0.40155(13) 0.2380(2) 0.0566(4) Uani d . 1 . . C
H6 0.3828 0.4669 0.2293 0.068 Uiso calc R 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
N1 0.0392(8) 0.0297(8) 0.0479(9) 0.000 0.0128(7) 0.000
N2 0.0480(9) 0.0326(9) 0.0474(10) 0.000 0.0164(8) 0.000
C4 0.0349(9) 0.0311(9) 0.0402(9) 0.000 0.0161(8) 0.000
C1 0.0399(10) 0.0299(9) 0.0408(10) 0.000 0.0175(8) 0.000
C3 0.0364(7) 0.0370(8) 0.0431(8) 0.0024(5) 0.0062(6) 0.0039(6)
O2 0.0801(8) 0.0380(6) 0.0563(7) -0.0050(5) 0.0113(6) -0.0102(5)
C2 0.0374(7) 0.0370(7) 0.0428(7) -0.0048(6) 0.0078(6) -0.0020(6)
O1 0.0444(6) 0.0538(7) 0.0729(8) 0.0088(5) 0.0189(5) -0.0050(5)
C5 0.0481(8) 0.0384(8) 0.0430(8) 0.0079(6) 0.0115(6) -0.0009(6)
C6 0.0698(9) 0.0341(8) 0.0570(9) 0.0086(7) 0.0098(8) -0.0023(7)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 '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'
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'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
1 -7 -5
4 -2 -4
0 -2 1
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
C5 N1 C5 2_655 . 109.75(16)
C5 N1 C4 2_655 . 125.12(8)
C5 N1 C4 . . 125.12(8)
O2 N2 O2 . 2_655 123.22(17)
O2 N2 C1 . . 118.39(8)
O2 N2 C1 2_655 . 118.39(8)
C3 C4 C3 . 2_655 120.56(17)
C3 C4 N1 . . 119.72(9)
C3 C4 N1 2_655 . 119.72(9)
C2 C1 C2 2_655 . 122.33(17)
C2 C1 N2 2_655 . 118.83(9)
C2 C1 N2 . . 118.83(9)
C2 C3 C4 . . 119.94(13)
C2 C3 H3 . . 120.0
C4 C3 H3 . . 120.0
C1 C2 C3 . . 118.61(12)
C1 C2 H2 . . 120.7
C3 C2 H2 . . 120.7
O1 C5 N1 . . 125.34(13)
O1 C5 C6 . . 129.06(14)
N1 C5 C6 . . 105.59(13)
C6 C6 C5 2_655 . 109.52(9)
C6 C6 H6 2_655 . 125.2
C5 C6 H6 . . 125.2
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
N1 C5 2_655 1.4052(17) ?
N1 C5 . 1.4052(17) ?
N1 C4 . 1.423(2) ?
N2 O2 . 1.2217(13) ?
N2 O2 2_655 1.2217(13) ?
N2 C1 . 1.462(2) ?
C4 C3 . 1.3835(16) ?
C4 C3 2_655 1.3835(16) ?
C1 C2 2_655 1.3777(16) ?
C1 C2 . 1.3777(16) ?
C3 C2 . 1.379(2) ?
C3 H3 . 0.930 ?
C2 H2 . 0.930 ?
O1 C5 . 1.1979(18) ?
C5 C6 . 1.487(2) ?
C6 C6 2_655 1.305(3) ?
C6 H6 . 0.930 ?
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_1
_geom_torsion_site_symmetry_4
_geom_torsion
C5 N1 C4 C3 2_655 . -136.82(10)
C5 N1 C4 C3 . . 43.18(10)
C5 N1 C4 C3 2_655 2_655 43.18(10)
C5 N1 C4 C3 . 2_655 -136.82(10)
O2 N2 C1 C2 . 2_655 -159.26(10)
O2 N2 C1 C2 2_655 2_655 20.74(10)
O2 N2 C1 C2 . . 20.74(10)
O2 N2 C1 C2 2_655 . -159.26(10)
C3 C4 C3 C2 2_655 . -0.20(9)
N1 C4 C3 C2 . . 179.80(9)
C2 C1 C2 C3 2_655 . -0.20(9)
N2 C1 C2 C3 . . 179.80(9)
C4 C3 C2 C1 . . 0.39(18)
C5 N1 C5 O1 2_655 . 179.43(17)
C4 N1 C5 O1 . . -0.57(17)
C5 N1 C5 C6 2_655 . -0.39(7)
C4 N1 C5 C6 . . 179.61(7)
O1 C5 C6 C6 . 2_655 -178.66(18)
N1 C5 C6 C6 . 2_655 1.2(2)
