#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/32/2213206.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_2213206
loop_
_publ_author_name
'C. Remya'
'D. Gayathri'
'D. Velmurugan'
'K. Ravikumar'
'M. Poornachandran'
_publ_section_title
1'-Nitro-2'-(3-nitrophenyl)-2',3',5',6',7',7a'-hexahydroindan-2-spiro-3'-1'H-pyrrolizine-1,3-dione
_journal_coeditor_code           CI2320
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2218
_journal_page_last               o2220
_journal_paper_doi               10.1107/S1600536807014286
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C21 H17 N3 O6'
_chemical_formula_moiety         'C21 H17 N3 O6'
_chemical_formula_sum            'C21 H17 N3 O6'
_chemical_formula_weight         407.38
_chemical_name_systematic
;
1'-Nitro-2'-(3-nitrophenyl)-2',3',5',6',7',7a'-hexahydroindan-2-spiro-
3'-1'H-pyrrolizine-1,3-dione
;
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_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                   26.1766(15)
_cell_length_b                   8.1726(5)
_cell_length_c                   17.7838(10)
_cell_measurement_reflns_used    2185
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.03
_cell_measurement_theta_min      2.29
_cell_volume                     3804.5(4)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 and PARST (Nardelli, 1995)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device       'Bruker SMART APEX CCD'
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       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  0.0262
_diffrn_reflns_av_sigmaI/netI    0.0180
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            30526
_diffrn_reflns_theta_full        28.03
_diffrn_reflns_theta_max         28.03
_diffrn_reflns_theta_min         2.29
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1696
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.189
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4520
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0860
_refine_ls_R_factor_gt           0.0597
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1015P)²+1.0427P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1701
_refine_ls_wR_factor_ref         0.1945
_reflns_number_gt                3036
_reflns_number_total             4520
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci2320.cif
_cod_data_source_block           I
_cod_database_code               2213206
_cod_database_fobs_code          2213206
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, 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
C C1 0.57952(13) 0.5449(4) 0.2524(2) 0.1048(11) Uani d . 1
H H1A 0.5437 0.5747 0.2493 0.126 Uiso calc R 1
H H1B 0.5977 0.5942 0.2107 0.126 Uiso calc R 1
C C2 0.60190(14) 0.5963(4) 0.3258(2) 0.1080(11) Uani d . 1
H H2A 0.6100 0.7121 0.3261 0.130 Uiso calc R 1
H H2B 0.5790 0.5722 0.3673 0.130 Uiso calc R 1
C C3 0.64867(11) 0.4950(4) 0.32952(18) 0.0897(9) Uani d . 1
H H3A 0.6603 0.4836 0.3810 0.108 Uiso calc R 1
H H3B 0.6758 0.5432 0.2998 0.108 Uiso calc R 1
C C4 0.63267(9) 0.3284(3) 0.29712(12) 0.0624(5) Uani d . 1
H H4 0.6242 0.2534 0.3383 0.075 Uiso calc R 1
C C5 0.67000(8) 0.2433(2) 0.24176(11) 0.0520(5) Uani d . 1
H H5 0.6690 0.1250 0.2504 0.062 Uiso calc R 1
C C6 0.64935(7) 0.2793(2) 0.16423(10) 0.0468(4) Uani d . 1
H H6 0.6593 0.3917 0.1518 0.056 Uiso calc R 1
C C7 0.59131(8) 0.2811(3) 0.18035(12) 0.0565(5) Uani d . 1
C C8 0.66610(7) 0.1721(2) 0.09944(10) 0.0448(4) Uani d . 1
C C9 0.67085(7) 0.0026(2) 0.10568(11) 0.0492(4) Uani d . 1
H H9 0.6652 -0.0493 0.1515 0.059 Uiso calc R 1
C C10 0.68403(7) -0.0862(2) 0.04307(12) 0.0529(5) Uani d . 1
C C11 0.69335(8) -0.0176(3) -0.02588(13) 0.0617(5) Uani d . 1
H H11 0.7021 -0.0815 -0.0672 0.074 Uiso calc R 1
C C12 0.68931(9) 0.1500(3) -0.03149(12) 0.0643(6) Uani d . 1
H H12 0.6959 0.2009 -0.0772 0.077 Uiso calc R 1
C C13 0.67554(8) 0.2433(2) 0.02998(11) 0.0551(5) Uani d . 1
H H13 0.6725 0.3561 0.0247 0.066 Uiso calc R 1
C C14 0.56706(8) 0.1100(3) 0.18843(13) 0.0620(5) Uani d . 1
C C15 0.52226(8) 0.1035(3) 0.13853(13) 0.0698(6) Uani d . 1
C C16 0.48735(11) -0.0245(4) 0.12877(17) 0.0946(9) Uani d . 1
H H16 0.4898 -0.1208 0.1564 0.114 Uiso calc R 1
C C17 0.44938(12) -0.0014(6) 0.0766(2) 0.1131(13) Uani d . 1
H H17 0.4257 -0.0844 0.0687 0.136 Uiso calc R 1
C C18 0.44540(11) 0.1384(7) 0.0364(2) 0.1156(13) Uani d . 1
H H18 0.4189 0.1486 0.0019 0.139 Uiso calc R 1
C C19 0.47935(10) 0.2667(5) 0.04483(18) 0.0941(9) Uani d . 1
H H19 0.4765 0.3622 0.0168 0.113 Uiso calc R 1
C C20 0.51810(8) 0.2452(4) 0.09759(14) 0.0722(7) Uani d . 1
C C21 0.56005(9) 0.3589(3) 0.11630(15) 0.0693(6) Uani d . 1
N N1 0.58597(7) 0.3644(3) 0.25275(11) 0.0676(5) Uani d . 1
N N2 0.72315(7) 0.3039(3) 0.25456(11) 0.0673(5) Uani d . 1
N N3 0.68717(8) -0.2649(2) 0.05024(15) 0.0727(6) Uani d . 1
O O1 0.74122(8) 0.4013(3) 0.21189(13) 0.1115(8) Uani d . 1
O O2 0.74468(8) 0.2511(3) 0.30968(12) 0.1019(7) Uani d . 1
O O3 0.68728(11) -0.3242(2) 0.11208(15) 0.1192(9) Uani d . 1
O O4 0.68983(10) -0.3462(2) -0.00626(15) 0.1119(8) Uani d . 1
O O5 0.58248(7) 0.0023(2) 0.22942(11) 0.0809(5) Uani d . 1
O O6 0.56975(8) 0.4864(3) 0.08570(13) 0.1009(7) 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_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
N1 C1 C2 103.4(3) ?
N1 C1 H1A 111.1 ?
C2 C1 H1A 111.1 ?
N1 C1 H1B 111.1 ?
C2 C1 H1B 111.1 ?
H1A C1 H1B 109.0 ?
C3 C2 C1 101.9(2) ?
C3 C2 H2A 111.4 ?
C1 C2 H2A 111.4 ?
C3 C2 H2B 111.4 ?
C1 C2 H2B 111.4 ?
H2A C2 H2B 109.3 ?
C2 C3 C4 104.7(2) ?
C2 C3 H3A 110.8 ?
C4 C3 H3A 110.8 ?
C2 C3 H3B 110.8 ?
C4 C3 H3B 110.8 ?
H3A C3 H3B 108.9 ?
N1 C4 C3 104.38(19) ?
N1 C4 C5 105.67(16) ?
C3 C4 C5 117.6(2) ?
N1 C4 H4 109.6 ?
C3 C4 H4 109.6 ?
C5 C4 H4 109.6 ?
N2 C5 C6 114.07(16) ?
N2 C5 C4 109.95(16) ?
C6 C5 C4 105.46(16) ?
N2 C5 H5 109.1 ?
C6 C5 H5 109.1 ?
C4 C5 H5 109.1 ?
C5 C6 C8 118.62(16) ?
C5 C6 C7 100.61(15) ?
C8 C6 C7 115.55(15) ?
C5 C6 H6 107.1 ?
C8 C6 H6 107.1 ?
C7 C6 H6 107.1 ?
N1 C7 C21 114.06(18) ?
N1 C7 C14 107.50(18) ?
C21 C7 C14 102.98(18) ?
N1 C7 C6 105.15(15) ?
C21 C7 C6 112.87(18) ?
C14 C7 C6 114.43(17) ?
C13 C8 C9 118.09(18) ?
C13 C8 C6 119.15(16) ?
C9 C8 C6 122.72(16) ?
C10 C9 C8 118.86(18) ?
C10 C9 H9 120.6 ?
C8 C9 H9 120.6 ?
C11 C10 C9 123.64(18) ?
C11 C10 N3 118.4(2) ?
C9 C10 N3 117.99(19) ?
C10 C11 C12 117.3(2) ?
C10 C11 H11 121.4 ?
C12 C11 H11 121.4 ?
C11 C12 C13 120.8(2) ?
C11 C12 H12 119.6 ?
C13 C12 H12 119.6 ?
C12 C13 C8 121.35(18) ?
C12 C13 H13 119.3 ?
C8 C13 H13 119.3 ?
O5 C14 C15 127.0(2) ?
O5 C14 C7 125.3(2) ?
C15 C14 C7 107.7(2) ?
C20 C15 C16 120.9(3) ?
C20 C15 C14 110.7(2) ?
C16 C15 C14 128.4(3) ?
C17 C16 C15 117.0(4) ?
C17 C16 H16 121.5 ?
C15 C16 H16 121.5 ?
C18 C17 C16 122.0(3) ?
C18 C17 H17 119.0 ?
C16 C17 H17 119.0 ?
C17 C18 C19 122.3(3) ?
C17 C18 H18 118.9 ?
C19 C18 H18 118.9 ?
C18 C19 C20 116.5(4) ?
C18 C19 H19 121.8 ?
C20 C19 H19 121.8 ?
C15 C20 C19 121.4(3) ?
C15 C20 C21 110.6(2) ?
C19 C20 C21 127.9(3) ?
O6 C21 C20 126.9(2) ?
O6 C21 C7 125.5(2) ?
C20 C21 C7 107.6(2) ?
C7 N1 C4 107.3(2) y
C7 N1 C1 118.0(2) y
C4 N1 C1 107.0(2) y
O1 N2 O2 124.5(2) y
O1 N2 C5 119.4(2) y
O2 N2 C5 116.0(2) y
O3 N3 O4 122.7(2) y
O3 N3 C10 118.7(2) y
O4 N3 C10 118.6(2) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 1.485(4) y
C1 C2 1.491(5) ?
C1 H1A 0.97 ?
C1 H1B 0.97 ?
C2 C3 1.479(4) ?
C2 H2A 0.97 ?
C2 H2B 0.97 ?
C3 C4 1.536(4) ?
C3 H3A 0.97 ?
C3 H3B 0.97 ?
C4 N1 1.484(3) y
C4 C5 1.552(3) ?
C4 H4 0.98 ?
C5 N2 1.494(3) y
C5 C6 1.510(3) ?
C5 H5 0.98 ?
C6 C8 1.512(3) ?
C6 C7 1.546(3) ?
C6 H6 0.98 ?
C7 N1 1.463(3) y
C7 C21 1.540(3) ?
C7 C14 1.542(3) ?
C8 C13 1.387(3) ?
C8 C9 1.395(3) ?
C9 C10 1.373(3) ?
C9 H9 0.93 ?
C10 C11 1.370(3) ?
C10 N3 1.469(3) y
C11 C12 1.377(3) ?
C11 H11 0.93 ?
C12 C13 1.380(3) ?
C12 H12 0.93 ?
C13 H13 0.93 ?
C14 O5 1.212(3) y
C14 C15 1.471(3) ?
C15 C20 1.372(4) ?
C15 C16 1.400(4) ?
C16 C17 1.373(5) ?
C16 H16 0.93 ?
C17 C18 1.351(6) ?
C17 H17 0.93 ?
C18 C19 1.383(5) ?
C18 H18 0.93 ?
C19 C20 1.393(4) ?
C19 H19 0.93 ?
C20 C21 1.476(4) ?
C21 O6 1.203(3) y
N2 O1 1.197(3) y
N2 O2 1.210(3) y
N3 O3 1.201(3) y
N3 O4 1.206(3) y
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 O6 . 0.97 2.50 3.014(4) 113
C3 H3B O1 . 0.97 2.59 3.291(4) 129
C3 H3B N2 . 0.97 2.45 2.831(4) 103
C5 H5 O5 . 0.98 2.51 3.029(3) 113
C3 H3A O4 7_556 0.97 2.43 3.342(4) 158
C6 H6 O3 1_565 0.98 2.54 3.514(2) 176
C12 H12 O2 2_654 0.93 2.57 3.408(3) 150
C13 H13 O4 1_565 0.93 2.54 3.437(2) 163
C19 H19 O6 5_665 0.93 2.51 3.333(4) 147
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
N1 C1 C2 C3 42.8(4)
C1 C2 C3 C4 -38.8(4)
C2 C3 C4 N1 20.3(3)
C2 C3 C4 C5 137.0(3)
N1 C4 C5 N2 139.69(18)
C3 C4 C5 N2 23.7(3)
N1 C4 C5 C6 16.3(2)
C3 C4 C5 C6 -99.7(2)
N2 C5 C6 C8 78.7(2)
C4 C5 C6 C8 -160.56(16)
N2 C5 C6 C7 -154.30(17)
C4 C5 C6 C7 -33.55(19)
C5 C6 C7 N1 40.01(19)
C8 C6 C7 N1 169.04(16)
C5 C6 C7 C21 164.94(18)
C8 C6 C7 C21 -66.0(2)
C5 C6 C7 C14 -77.7(2)
C8 C6 C7 C14 51.3(2)
C5 C6 C8 C13 -141.22(18)
C7 C6 C8 C13 99.2(2)
C5 C6 C8 C9 41.1(2)
C7 C6 C8 C9 -78.5(2)
C13 C8 C9 C10 -0.7(3)
C6 C8 C9 C10 177.05(16)
C8 C9 C10 C11 0.6(3)
C8 C9 C10 N3 -178.01(17)
C9 C10 C11 C12 0.3(3)
N3 C10 C11 C12 178.90(19)
C10 C11 C12 C13 -1.1(3)
C11 C12 C13 C8 1.0(3)
C9 C8 C13 C12 -0.1(3)
C6 C8 C13 C12 -177.89(19)
N1 C7 C14 O5 -64.7(3)
C21 C7 C14 O5 174.5(2)
C6 C7 C14 O5 51.7(3)
N1 C7 C14 C15 114.70(19)
C21 C7 C14 C15 -6.1(2)
C6 C7 C14 C15 -128.93(19)
O5 C14 C15 C20 -176.8(2)
C7 C14 C15 C20 3.8(3)
O5 C14 C15 C16 1.7(4)
C7 C14 C15 C16 -177.7(2)
C20 C15 C16 C17 0.3(4)
C14 C15 C16 C17 -178.1(3)
C15 C16 C17 C18 -0.3(5)
C16 C17 C18 C19 0.3(6)
C17 C18 C19 C20 -0.4(5)
C16 C15 C20 C19 -0.3(4)
C14 C15 C20 C19 178.3(2)
C16 C15 C20 C21 -178.3(2)
C14 C15 C20 C21 0.3(3)
C18 C19 C20 C15 0.3(4)
C18 C19 C20 C21 178.0(3)
C15 C20 C21 O6 173.0(3)
C19 C20 C21 O6 -4.8(5)
C15 C20 C21 C7 -4.3(3)
C19 C20 C21 C7 177.8(2)
N1 C7 C21 O6 72.7(3)
C14 C7 C21 O6 -171.2(3)
C6 C7 C21 O6 -47.3(3)
N1 C7 C21 C20 -109.9(2)
C14 C7 C21 C20 6.2(2)
C6 C7 C21 C20 130.1(2)
C21 C7 N1 C4 -155.19(19)
C14 C7 N1 C4 91.3(2)
C6 C7 N1 C4 -31.0(2)
C21 C7 N1 C1 -34.4(3)
C14 C7 N1 C1 -147.9(2)
C6 C7 N1 C1 89.8(2)
C3 C4 N1 C7 134.0(2)
C5 C4 N1 C7 9.3(2)
C3 C4 N1 C1 6.4(3)
C5 C4 N1 C1 -118.2(2)
C2 C1 N1 C7 -151.5(2)
C2 C1 N1 C4 -30.6(3)
C6 C5 N2 O1 15.1(3)
C4 C5 N2 O1 -103.1(3)
C6 C5 N2 O2 -166.23(19)
C4 C5 N2 O2 75.5(2)
C11 C10 N3 O3 168.1(2)
C9 C10 N3 O3 -13.2(3)
C11 C10 N3 O4 -11.4(3)
C9 C10 N3 O4 167.2(2)
