#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/29/2232923.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_2232923
loop_
_publ_author_name
'Karthikeyan, S.'
'Sethusankar, K.'
'Devaraj, Anthonisamy'
'Bakthadoss, Manickam'
_publ_section_title
;
 2-[(6-Nitro-1,3-benzodioxol-5-yl)methylidene]malononitrile
;
_journal_coeditor_code           RK2314
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3469
_journal_paper_doi               10.1107/S1600536811049816
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C11 H5 N3 O4'
_chemical_formula_moiety         'C11 H5 N3 O4'
_chemical_formula_sum            'C11 H5 N3 O4'
_chemical_formula_weight         243.18
_chemical_name_systematic
;
2-[(6-Nitro-1,3-benzodioxol-5-yl)methylidene]malononitrile
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                84.470(2)
_cell_angle_beta                 67.634(2)
_cell_angle_gamma                78.874(2)
_cell_formula_units_Z            2
_cell_length_a                   7.0953(2)
_cell_length_b                   8.8847(3)
_cell_length_c                   9.2212(3)
_cell_measurement_reflns_used    3494
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      31.57
_cell_measurement_theta_min      0.990
_cell_volume                     527.30(3)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al.
2008)
;
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       'ω scans'
_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  0.0251
_diffrn_reflns_av_sigmaI/netI    0.0207
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13806
_diffrn_reflns_theta_full        31.57
_diffrn_reflns_theta_max         31.57
_diffrn_reflns_theta_min         2.34
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             248
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.301
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         3494
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0476
_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)+(0.0779P)²+0.0833P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1300
_refine_ls_wR_factor_ref         0.1422
_reflns_number_gt                2700
_reflns_number_total             3494
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rk2314.cif
_cod_data_source_block           I
_cod_database_code               2232923
_cod_database_fobs_code          2232923
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
_atom_site_symmetry_multiplicity
C C1 0.1956(2) 0.45131(18) 0.79855(15) 0.0499(3) Uani d . 1 1
H H1A 0.2553 0.3433 0.7969 0.060 Uiso calc R 1 1
H H1B 0.2182 0.4995 0.8792 0.060 Uiso calc R 1 1
C C2 0.13009(16) 0.60560(13) 0.61230(12) 0.0335(2) Uani d . 1 1
C C3 0.13982(17) 0.70725(13) 0.48999(12) 0.0345(2) Uani d . 1 1
H H3 0.2663 0.7286 0.4190 0.041 Uiso calc R 1 1
C C4 -0.04642(16) 0.77900(12) 0.47404(12) 0.0309(2) Uani d . 1 1
C C5 -0.23081(16) 0.74097(12) 0.58573(13) 0.0331(2) Uani d . 1 1
C C6 -0.24088(17) 0.63890(13) 0.71134(13) 0.0373(2) Uani d . 1 1
H H6 -0.3660 0.6171 0.7842 0.045 Uiso calc R 1 1
C C7 -0.05588(18) 0.57270(13) 0.72113(12) 0.0351(2) Uani d . 1 1
C C8 -0.04545(17) 0.90159(12) 0.35650(13) 0.0347(2) Uani d . 1 1
H H8 -0.1612 0.9786 0.3818 0.042 Uiso calc R 1 1
C C9 0.10476(19) 0.91503(13) 0.21576(14) 0.0386(2) Uani d . 1 1
C C10 0.0900(2) 1.05218(15) 0.12130(16) 0.0478(3) Uani d . 1 1
C C11 0.2814(2) 0.79907(17) 0.14691(15) 0.0491(3) Uani d . 1 1
N N1 -0.42888(15) 0.80802(11) 0.57275(13) 0.0417(2) Uani d . 1 1
N N2 0.0804(3) 1.16093(16) 0.04706(18) 0.0707(4) Uani d . 1 1
N N3 0.4220(2) 0.7081(2) 0.09043(17) 0.0760(5) Uani d . 1 1
O O1 -0.02108(14) 0.46924(11) 0.82958(10) 0.0483(2) Uani d . 1 1
O O2 0.28869(13) 0.52328(11) 0.64860(10) 0.0457(2) Uani d . 1 1
O O3 -0.43369(15) 0.84163(11) 0.44228(12) 0.0507(3) Uani d . 1 1
O O4 -0.58153(15) 0.82535(14) 0.69255(14) 0.0674(4) Uani d . 1 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_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 C1 O2 107.04(9)
O1 C1 H1A 110.3
O2 C1 H1A 110.3
O1 C1 H1B 110.3
O2 C1 H1B 110.3
H1A C1 H1B 108.6
O2 C2 C3 128.07(10)
O2 C2 C7 109.65(9)
C3 C2 C7 122.28(10)
C2 C3 C4 118.30(10)
C2 C3 H3 120.9
C4 C3 H3 120.9
C5 C4 C3 117.50(9)
C5 C4 C8 121.96(9)
C3 C4 C8 120.12(9)
C6 C5 C4 124.20(10)
C6 C5 N1 115.70(10)
C4 C5 N1 120.10(10)
C7 C6 C5 115.83(10)
C7 C6 H6 122.1
C5 C6 H6 122.1
O1 C7 C6 128.09(10)
O1 C7 C2 110.03(10)
C6 C7 C2 121.87(10)
C9 C8 C4 126.91(10)
C9 C8 H8 116.5
C4 C8 H8 116.5
C8 C9 C11 124.80(11)
C8 C9 C10 119.43(12)
C11 C9 C10 115.74(11)
N2 C10 C9 179.14(15)
N3 C11 C9 179.09(15)
O4 N1 O3 123.24(11)
O4 N1 C5 118.09(11)
O3 N1 C5 118.67(10)
C7 O1 C1 105.81(9)
C2 O2 C1 105.89(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.4319(17)
C1 O2 1.4334(15)
C1 H1A 0.9700
C1 H1B 0.9700
C2 O2 1.3547(13)
C2 C3 1.3641(15)
C2 C7 1.3850(16)
C3 C4 1.4068(14)
C3 H3 0.9300
C4 C5 1.4016(15)
C4 C8 1.4597(14)
C5 C6 1.3887(15)
C5 N1 1.4614(14)
C6 C7 1.3635(15)
C6 H6 0.9300
C7 O1 1.3525(13)
C8 C9 1.3420(16)
C8 H8 0.9300
C9 C11 1.4342(19)
C9 C10 1.4388(16)
C10 N2 1.1355(18)
C11 N3 1.138(2)
N1 O4 1.2145(15)
N1 O3 1.2230(14)
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
C1 H1B O1 2_567 0.97 2.53 3.2692(16) 133
C8 H8 O4 2_476 0.93 2.52 3.3640(17) 152
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
O2 C2 C3 C4 179.32(11)
C7 C2 C3 C4 -0.78(17)
C2 C3 C4 C5 0.01(16)
C2 C3 C4 C8 172.74(10)
C3 C4 C5 C6 0.80(17)
C8 C4 C5 C6 -171.78(10)
C3 C4 C5 N1 -178.10(9)
C8 C4 C5 N1 9.32(16)
C4 C5 C6 C7 -0.81(17)
N1 C5 C6 C7 178.14(10)
C5 C6 C7 O1 -179.34(11)
C5 C6 C7 C2 0.01(17)
O2 C2 C7 O1 0.17(14)
C3 C2 C7 O1 -179.75(10)
O2 C2 C7 C6 -179.29(10)
C3 C2 C7 C6 0.79(18)
C5 C4 C8 C9 -154.85(11)
C3 C4 C8 C9 32.75(16)
C4 C8 C9 C11 8.72(19)
C4 C8 C9 C10 -173.31(10)
C6 C5 N1 O4 29.91(16)
C4 C5 N1 O4 -151.10(12)
C6 C5 N1 O3 -148.95(11)
C4 C5 N1 O3 30.04(15)
C6 C7 O1 C1 -173.03(12)
C2 C7 O1 C1 7.55(14)
O2 C1 O1 C7 -12.15(14)
C3 C2 O2 C1 172.11(12)
C7 C2 O2 C1 -7.80(14)
O1 C1 O2 C2 12.26(14)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 617296
