#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/94/2209436.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_2209436
loop_
_publ_author_name
'Moreno-Fuquen, Rodolfo'
'Valencia, Hoover'
'Pardo, Zulay Diney'
'D'Vries, Richard'
'Kennedy, Alan R.'
_publ_section_title
;
 N-(3-Nitrophenyl)maleimide
;
_journal_coeditor_code           CF2029
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2734
_journal_page_last               o2735
_journal_paper_doi               10.1107/S1600536806020940
_journal_volume                  62
_journal_year                    2006
_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          395.0(10)
_chemical_name_systematic        m-Nitrophenylmaleimide
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   18.9815(6)
_cell_length_b                   6.6643(2)
_cell_length_c                   14.8702(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      27.51
_cell_measurement_theta_min      2.55
_cell_volume                     1881.06(10)
_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_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4 diffractometer'
_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  0.032
_diffrn_reflns_av_sigmaI/netI    0.040
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            4072
_diffrn_reflns_theta_full        13.76
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         2.55
_diffrn_standards_decay_%        0.1
_diffrn_standards_interval_time  150
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.267
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         2238
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.068
_refine_ls_R_factor_gt           0.045
_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)+(0.0754P)²+0.0433P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.105
_refine_ls_wR_factor_ref         0.119
_reflns_number_gt                1693
_reflns_number_total             2238
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cf2029.cif
_cod_data_source_block           I
_cod_database_code               2209436
_cod_database_fobs_code          2209436
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'
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 0.55002(13) 0.9037(4) 0.9815(2) 0.0418(7) Uani d . 1
O O2 0.61359(13) 1.1499(4) 1.0305(2) 0.0336(6) Uani d . 1
O O3 0.91013(14) 0.7232(5) 1.0915(2) 0.0443(7) Uani d . 1
O O4 0.84956(12) 1.2131(4) 0.8924(2) 0.0330(6) Uani d . 1
O O5 0.81692(13) 0.5768(4) 0.7350(2) 0.0373(6) Uani d . 1
O O6 0.88410(13) 0.3317(3) 0.6919(2) 0.0324(6) Uani d . 1
O O7 1.17689(15) 0.7919(5) 0.6292(2) 0.0474(8) Uani d . 1
O O8 1.11689(14) 0.2920(3) 0.82382(19) 0.0310(6) Uani d . 1
N N1 0.60690(15) 0.9805(4) 0.9992(2) 0.0288(7) Uani d . 1
N N2 0.86358(14) 0.9338(4) 0.98297(19) 0.0237(6) Uani d . 1
N N3 0.87500(15) 0.5040(4) 0.7210(2) 0.0281(7) Uani d . 1
N N4 1.13008(15) 0.5751(4) 0.73457(19) 0.0237(6) Uani d . 1
C C1 0.67096(18) 0.8626(5) 0.9812(2) 0.0254(8) Uani d . 1
C C2 0.6639(2) 0.6636(5) 0.9546(2) 0.0282(8) Uani d . 1
H H2 0.6188 0.6041 0.9476 0.034 Uiso calc R 1
C C3 0.7248(2) 0.5549(5) 0.9387(3) 0.0320(8) Uani d . 1
H H3 0.7216 0.4178 0.9217 0.038 Uiso calc R 1
C C4 0.7910(2) 0.6447(5) 0.9473(3) 0.0279(8) Uani d . 1
H H4 0.8326 0.5699 0.9350 0.033 Uiso calc R 1
C C5 0.79573(18) 0.8449(5) 0.9739(2) 0.0239(8) Uani d . 1
C C6 0.73525(17) 0.9557(5) 0.9921(2) 0.0240(7) Uani d . 1
H H6 0.7382 1.0913 1.0114 0.029 Uiso calc R 1
C C7 0.91483(18) 0.8697(6) 1.0447(3) 0.0303(8) Uani d . 1
C C8 0.97290(19) 1.0196(6) 1.0392(3) 0.0360(9) Uani d . 1
H H8 1.0162 1.0124 1.0712 0.043 Uiso calc R 1
C C9 0.95494(19) 1.1638(5) 0.9830(3) 0.0323(8) Uani d . 1
H H9 0.9827 1.2780 0.9686 0.039 Uiso calc R 1
C C10 0.88335(19) 1.1171(5) 0.9458(3) 0.0258(7) Uani d . 1
C C11 0.93765(18) 0.6284(5) 0.7381(2) 0.0232(7) Uani d . 1
C C12 0.92815(18) 0.8288(5) 0.7621(2) 0.0272(8) Uani d . 1
H H12 0.8824 0.8839 0.7696 0.033 Uiso calc R 1
C C13 0.9875(2) 0.9439(5) 0.7746(3) 0.0295(8) Uani d . 1
H H13 0.9828 1.0820 0.7893 0.035 Uiso calc R 1
C C14 1.05406(19) 0.8610(5) 0.7661(2) 0.0266(8) Uani d . 1
H H14 1.0945 0.9420 0.7757 0.032 Uiso calc R 1
C C15 1.06188(17) 0.6608(4) 0.7437(2) 0.0229(7) Uani d . 1
C C16 1.00312(17) 0.5423(5) 0.7282(2) 0.0225(7) Uani d . 1
H H16 1.0079 0.4055 0.7111 0.027 Uiso calc R 1
C C17 1.18201(18) 0.6437(6) 0.6752(3) 0.0324(8) Uani d . 1
C C18 1.24049(19) 0.4970(6) 0.6797(3) 0.0361(9) Uani d . 1
H H18 1.2836 0.5061 0.6475 0.043 Uiso calc R 1
C C19 1.22294(19) 0.3507(5) 0.7361(3) 0.0332(8) Uani d . 1
H H19 1.2515 0.2386 0.7511 0.040 Uiso calc R 1
C C20 1.15106(18) 0.3915(5) 0.7721(2) 0.0255(8) Uani d . 1
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
1 1 2
0 1 3
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
O1 N1 O2 123.9(3) ?
O1 N1 C1 117.8(3) ?
O2 N1 C1 118.3(3) ?
C10 N2 C7 109.9(3) ?
C10 N2 C5 124.8(3) yes
C7 N2 C5 124.2(3) yes
O5 N3 O6 123.6(3) ?
O5 N3 C11 118.4(3) ?
O6 N3 C11 118.0(3) ?
C17 N4 C20 109.6(3) ?
C17 N4 C15 124.8(3) yes
C20 N4 C15 124.8(3) yes
C6 C1 C2 123.2(3) ?
C6 C1 N1 118.0(3) ?
C2 C1 N1 118.8(3) yes
C3 C2 C1 117.9(3) ?
C3 C2 H2 121.1 ?
C1 C2 H2 121.1 ?
C2 C3 C4 120.7(3) ?
C2 C3 H3 119.6 ?
C4 C3 H3 119.6 ?
C5 C4 C3 119.5(3) ?
C5 C4 H4 120.2 ?
C3 C4 H4 120.2 ?
C6 C5 C4 120.7(3) ?
C6 C5 N2 120.4(3) ?
C4 C5 N2 118.9(3) ?
C1 C6 C5 117.9(3) ?
C1 C6 H6 121.0 ?
C5 C6 H6 121.0 ?
O3 C7 N2 125.0(3) ?
O3 C7 C8 129.2(3) ?
N2 C7 C8 105.8(3) ?
C9 C8 C7 109.4(3) ?
C9 C8 H8 125.3 ?
C7 C8 H8 125.3 ?
C8 C9 C10 108.5(3) ?
C8 C9 H9 125.7 ?
C10 C9 H9 125.7 ?
O4 C10 N2 125.7(3) ?
O4 C10 C9 128.0(3) ?
N2 C10 C9 106.2(3) ?
C16 C11 C12 122.9(3) ?
C16 C11 N3 118.4(3) yes
C12 C11 N3 118.6(3) ?
C13 C12 C11 117.6(3) ?
C13 C12 H12 121.2 ?
C11 C12 H12 121.2 ?
C12 C13 C14 120.8(3) ?
C12 C13 H13 119.6 ?
C14 C13 H13 119.6 ?
C15 C14 C13 120.3(3) ?
C15 C14 H14 119.8 ?
C13 C14 H14 119.8 ?
C14 C15 C16 120.2(3) ?
C14 C15 N4 120.5(3) ?
C16 C15 N4 119.2(3) ?
C11 C16 C15 118.1(3) ?
C11 C16 H16 121.0 ?
C15 C16 H16 121.0 ?
O7 C17 N4 124.7(3) ?
O7 C17 C18 128.9(4) ?
N4 C17 C18 106.5(3) ?
C19 C18 C17 109.0(3) ?
C19 C18 H18 125.5 ?
C17 C18 H18 125.5 ?
C18 C19 C20 108.8(3) ?
C18 C19 H19 125.6 ?
C20 C19 H19 125.6 ?
O8 C20 N4 125.5(3) ?
O8 C20 C19 128.4(3) ?
N4 C20 C19 106.1(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 N1 1.223(4) ?
O2 N1 1.228(4) ?
O3 C7 1.202(5) ?
O4 C10 1.204(4) ?
O5 N3 1.222(4) ?
O6 N3 1.239(3) ?
O7 C17 1.205(5) ?
O8 C20 1.205(5) ?
N1 C1 1.473(4) ?
N2 C10 1.393(4) yes
N2 C7 1.404(4) yes
N2 C5 1.424(4) yes
N3 C11 1.472(4) ?
N4 C17 1.400(5) yes
N4 C20 1.403(4) yes
N4 C15 1.421(4) yes
C1 C6 1.379(5) ?
C1 C2 1.390(5) ?
C2 C3 1.385(5) ?
C2 H2 0.950 ?
C3 C4 1.398(5) ?
C3 H3 0.950 ?
C4 C5 1.394(5) yes
C4 H4 0.950 ?
C5 C6 1.392(4) yes
C6 H6 0.950 ?
C7 C8 1.490(5) ?
C8 C9 1.318(6) yes
C8 H8 0.950 ?
C9 C10 1.500(5) ?
C9 H9 0.950 ?
C11 C16 1.377(5) ?
C11 C12 1.394(4) ?
C12 C13 1.375(5) ?
C12 H12 0.950 ?
C13 C14 1.385(5) ?
C13 H13 0.950 ?
C14 C15 1.383(4) yes
C14 H14 0.950 ?
C15 C16 1.386(5) yes
C16 H16 0.950 ?
C17 C18 1.481(5) ?
C18 C19 1.329(6) yes
C18 H18 0.950 ?
C19 C20 1.490(5) ?
C19 H19 0.950 ?
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
_geom_torsion_publ_flag
O1 N1 C1 C6 173.4(3) ?
O2 N1 C1 C6 -6.3(5) ?
O1 N1 C1 C2 -6.9(5) yes
O2 N1 C1 C2 173.4(3) ?
C6 C1 C2 C3 0.1(5) ?
N1 C1 C2 C3 -179.5(3) ?
C1 C2 C3 C4 -1.4(5) ?
C2 C3 C4 C5 1.3(6) ?
C3 C4 C5 C6 0.1(5) ?
C3 C4 C5 N2 179.5(3) ?
C10 N2 C5 C6 -50.0(5) ?
C7 N2 C5 C6 116.7(4) yes
C10 N2 C5 C4 130.6(4) ?
C7 N2 C5 C4 -62.7(5) ?
C2 C1 C6 C5 1.2(5) ?
N1 C1 C6 C5 -179.2(3) ?
C4 C5 C6 C1 -1.3(5) ?
N2 C5 C6 C1 179.3(3) ?
C10 N2 C7 O3 175.1(4) ?
C5 N2 C7 O3 6.7(6) ?
C10 N2 C7 C8 -4.5(4) ?
C5 N2 C7 C8 -172.9(3) ?
O3 C7 C8 C9 -176.2(4) ?
N2 C7 C8 C9 3.3(4) ?
C7 C8 C9 C10 -1.0(4) ?
C7 N2 C10 O4 -178.0(3) ?
C5 N2 C10 O4 -9.7(6) ?
C7 N2 C10 C9 3.9(4) ?
C5 N2 C10 C9 172.3(3) ?
C8 C9 C10 O4 -179.8(4) ?
C8 C9 C10 N2 -1.8(4) ?
O5 N3 C11 C16 175.7(3) yes
O6 N3 C11 C16 -5.3(5) ?
O5 N3 C11 C12 -5.4(5) ?
O6 N3 C11 C12 173.6(3) ?
C16 C11 C12 C13 1.1(5) ?
N3 C11 C12 C13 -177.7(3) ?
C11 C12 C13 C14 -1.8(5) ?
C12 C13 C14 C15 0.8(6) ?
C13 C14 C15 C16 1.0(5) ?
C13 C14 C15 N4 179.8(3) ?
C17 N4 C15 C14 -57.8(5) ?
C20 N4 C15 C14 133.5(4) ?
C17 N4 C15 C16 121.0(4) ?
C20 N4 C15 C16 -47.8(5) yes
C12 C11 C16 C15 0.6(5) ?
N3 C11 C16 C15 179.5(3) ?
C14 C15 C16 C11 -1.7(5) ?
N4 C15 C16 C11 179.5(3) ?
C20 N4 C17 O7 175.6(4) ?
C15 N4 C17 O7 5.4(6) ?
C20 N4 C17 C18 -2.9(4) ?
C15 N4 C17 C18 -173.1(3) ?
O7 C17 C18 C19 -176.9(4) ?
N4 C17 C18 C19 1.5(4) ?
C17 C18 C19 C20 0.4(4) ?
C17 N4 C20 O8 -178.0(3) ?
C15 N4 C20 O8 -7.7(6) ?
C17 N4 C20 C19 3.1(4) ?
C15 N4 C20 C19 173.3(3) ?
C18 C19 C20 O8 178.9(4) ?
C18 C19 C20 N4 -2.1(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 206707
