#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/88/2208839.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_2208839
loop_
_publ_author_name
'D. Gayathri'
'D. Sujatha'
'D. Velmurugan'
'K. Ravikumar'
'M. Poornachandran'
_publ_section_title
;
 1-(3-Nitrophenyl)-5-tosylperhydropyrrolo[3,4-b]pyrrole
;
_journal_coeditor_code           CI2054
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2045
_journal_page_last               o2047
_journal_paper_doi               10.1107/S1600536806014243
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C19 H21 N3 O4 S'
_chemical_formula_moiety         'C19 H21 N3 O4 S'
_chemical_formula_sum            'C19 H21 N3 O4 S'
_chemical_formula_weight         387.45
_chemical_name_systematic
;
1-(3-Nitrophenyl)-5-tosylperhydropyrrolo[3,4-b]pyrrole
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 104.2860(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.4456(4)
_cell_length_b                   25.2680(15)
_cell_length_c                   10.0594(6)
_cell_measurement_reflns_used    1588
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      1.61
_cell_volume                     1834.00(18)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Bruker SMART APEX'
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_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  0.0246
_diffrn_reflns_av_sigmaI/netI    0.0181
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            17515
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.61
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.208
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.224
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.144
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3217
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.144
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0461
_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)+(0.0504P)²+0.7696P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1131
_refine_ls_wR_factor_ref         0.1161
_reflns_number_gt                2942
_reflns_number_total             3217
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci2054.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2208839
_cod_database_fobs_code          2208839
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
C C1 0.8692(3) 0.70348(8) 0.7704(2) 0.0472(5) Uani d . 1
H H1A 0.9034 0.7377 0.7405 0.057 Uiso calc R 1
H H1B 0.8836 0.7045 0.8688 0.057 Uiso calc R 1
C C2 0.6706(3) 0.68963(8) 0.6968(2) 0.0431(5) Uani d . 1
H H2 0.5916 0.6893 0.7616 0.052 Uiso calc R 1
C C3 0.6802(3) 0.63403(8) 0.63640(19) 0.0378(4) Uani d . 1
H H3 0.5825 0.6111 0.6539 0.045 Uiso calc R 1
C C4 0.8716(3) 0.61281(8) 0.7066(2) 0.0393(5) Uani d . 1
H H4A 0.8702 0.5946 0.7912 0.047 Uiso calc R 1
H H4B 0.9169 0.5888 0.6470 0.047 Uiso calc R 1
C C5 0.5852(4) 0.72383(10) 0.5738(2) 0.0627(7) Uani d . 1
H H5A 0.4510 0.7231 0.5546 0.075 Uiso calc R 1
H H5B 0.6271 0.7602 0.5891 0.075 Uiso calc R 1
C C6 0.6517(4) 0.69934(8) 0.4573(2) 0.0516(6) Uani d . 1
H H6A 0.5669 0.7068 0.3693 0.062 Uiso calc R 1
H H6B 0.7744 0.7120 0.4562 0.062 Uiso calc R 1
C C7 0.6582(2) 0.60435(7) 0.39624(19) 0.0357(4) Uani d . 1
C C8 0.6701(3) 0.61654(8) 0.2632(2) 0.0391(5) Uani d . 1
H H8 0.6786 0.6516 0.2370 0.047 Uiso calc R 1
C C9 0.6689(3) 0.57613(8) 0.1711(2) 0.0419(5) Uani d . 1
C C10 0.6565(3) 0.52366(9) 0.2025(2) 0.0505(5) Uani d . 1
H H10 0.6540 0.4973 0.1375 0.061 Uiso calc R 1
C C11 0.6479(3) 0.51175(8) 0.3337(2) 0.0519(6) Uani d . 1
H H11 0.6407 0.4765 0.3583 0.062 Uiso calc R 1
C C12 0.6497(3) 0.55046(8) 0.4299(2) 0.0434(5) Uani d . 1
H H12 0.6452 0.5410 0.5184 0.052 Uiso calc R 1
C C13 1.1909(3) 0.63953(8) 0.9931(2) 0.0415(5) Uani d . 1
C C14 1.1760(3) 0.58707(9) 1.0276(2) 0.0494(5) Uani d . 1
H H14 1.1736 0.5606 0.9630 0.059 Uiso calc R 1
C C15 1.1649(3) 0.57427(10) 1.1586(3) 0.0581(6) Uani d . 1
H H15 1.1557 0.5389 1.1815 0.070 Uiso calc R 1
C C16 1.1669(3) 0.61273(11) 1.2564(2) 0.0555(6) Uani d . 1
C C17 1.1806(3) 0.66486(10) 1.2195(2) 0.0551(6) Uani d . 1
H H17 1.1819 0.6913 1.2840 0.066 Uiso calc R 1
C C18 1.1924(3) 0.67877(9) 1.0894(2) 0.0485(5) Uani d . 1
H H18 1.2014 0.7142 1.0666 0.058 Uiso calc R 1
C C19 1.1585(4) 0.59821(14) 1.3999(3) 0.0810(9) Uani d . 1
H H19A 1.0957 0.5649 1.3983 0.122 Uiso calc R 1
H H19B 1.0923 0.6251 1.4356 0.122 Uiso calc R 1
H H19C 1.2820 0.5953 1.4571 0.122 Uiso calc R 1
N N1 0.9849(2) 0.66127(6) 0.73342(17) 0.0387(4) Uani d . 1
N N2 0.6543(2) 0.64347(6) 0.48937(16) 0.0409(4) Uani d . 1
N N3 0.6841(3) 0.59033(9) 0.03284(19) 0.0529(5) Uani d . 1
O O1 1.2766(2) 0.70814(6) 0.82750(17) 0.0553(4) Uani d . 1
O O2 1.2790(2) 0.61314(7) 0.76845(17) 0.0558(4) Uani d . 1
O O3 0.6943(3) 0.63668(8) 0.00452(17) 0.0731(5) Uani d . 1
O O4 0.6884(3) 0.55461(8) -0.04817(18) 0.0785(6) Uani d . 1
S S1 1.19851(7) 0.65638(2) 0.82405(5) 0.04216(18) 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'
S S 0.1246 0.1234 '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 105.60(16) ?
N1 C1 H1A 110.6 ?
C2 C1 H1A 110.6 ?
N1 C1 H1B 110.6 ?
C2 C1 H1B 110.6 ?
H1A C1 H1B 108.8 ?
C5 C2 C1 115.3(2) ?
C5 C2 C3 104.45(17) ?
C1 C2 C3 105.50(16) ?
C5 C2 H2 110.4 ?
C1 C2 H2 110.4 ?
C3 C2 H2 110.4 ?
N2 C3 C4 113.65(16) ?
N2 C3 C2 104.04(15) ?
C4 C3 C2 105.55(16) ?
N2 C3 H3 111.1 ?
C4 C3 H3 111.1 ?
C2 C3 H3 111.1 ?
N1 C4 C3 102.72(15) ?
N1 C4 H4A 111.2 ?
C3 C4 H4A 111.2 ?
N1 C4 H4B 111.2 ?
C3 C4 H4B 111.2 ?
H4A C4 H4B 109.1 ?
C6 C5 C2 104.35(17) ?
C6 C5 H5A 110.9 ?
C2 C5 H5A 110.9 ?
C6 C5 H5B 110.9 ?
C2 C5 H5B 110.9 ?
H5A C5 H5B 108.9 ?
N2 C6 C5 102.42(18) ?
N2 C6 H6A 111.3 ?
C5 C6 H6A 111.3 ?
N2 C6 H6B 111.3 ?
C5 C6 H6B 111.3 ?
H6A C6 H6B 109.2 ?
N2 C7 C8 120.95(17) ?
N2 C7 C12 121.62(18) ?
C8 C7 C12 117.43(18) ?
C9 C8 C7 119.29(18) ?
C9 C8 H8 120.4 ?
C7 C8 H8 120.4 ?
C10 C9 C8 123.50(19) ?
C10 C9 N3 118.67(19) ?
C8 C9 N3 117.83(19) ?
C11 C10 C9 117.1(2) ?
C11 C10 H10 121.4 ?
C9 C10 H10 121.4 ?
C10 C11 C12 121.8(2) ?
C10 C11 H11 119.1 ?
C12 C11 H11 119.1 ?
C11 C12 C7 120.80(19) ?
C11 C12 H12 119.6 ?
C7 C12 H12 119.6 ?
C14 C13 C18 119.9(2) ?
C14 C13 S1 119.78(17) ?
C18 C13 S1 120.28(17) ?
C15 C14 C13 119.5(2) ?
C15 C14 H14 120.2 ?
C13 C14 H14 120.2 ?
C14 C15 C16 121.6(2) ?
C14 C15 H15 119.2 ?
C16 C15 H15 119.2 ?
C17 C16 C15 118.0(2) ?
C17 C16 C19 121.0(3) ?
C15 C16 C19 121.1(3) ?
C18 C17 C16 121.7(2) ?
C18 C17 H17 119.2 ?
C16 C17 H17 119.2 ?
C17 C18 C13 119.4(2) ?
C17 C18 H18 120.3 ?
C13 C18 H18 120.3 ?
C16 C19 H19A 109.5 ?
C16 C19 H19B 109.5 ?
H19A C19 H19B 109.5 ?
C16 C19 H19C 109.5 ?
H19A C19 H19C 109.5 ?
H19B C19 H19C 109.5 ?
C4 N1 C1 107.7(2) y
C4 N1 S1 118.30(10) y
C1 N1 S1 117.60(10) y
C7 N2 C6 123.6(2) y
C7 N2 C3 123.7(2) y
C6 N2 C3 112.1(2) y
O3 N3 O4 122.9(2) y
O3 N3 C9 118.9(2) y
O4 N3 C9 118.2(2) y
O2 S1 O1 120.20(10) y
O2 S1 N1 106.60(10) y
O1 S1 N1 106.20(10) y
O2 S1 C13 108.00(10) y
O1 S1 C13 107.90(10) y
N1 S1 C13 107.30(10) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 1.475(3) y
C1 C2 1.522(3) ?
C1 H1A 0.97 ?
C1 H1B 0.97 ?
C2 C5 1.514(3) ?
C2 C3 1.539(3) ?
C2 H2 0.98 ?
C3 N2 1.463(2) y
C3 C4 1.523(3) ?
C3 H3 0.98 ?
C4 N1 1.474(2) y
C4 H4A 0.97 ?
C4 H4B 0.97 ?
C5 C6 1.513(3) ?
C5 H5A 0.97 ?
C5 H5B 0.97 ?
C6 N2 1.447(3) y
C6 H6A 0.97 ?
C6 H6B 0.97 ?
C7 N2 1.367(2) y
C7 C8 1.398(3) ?
C7 C12 1.409(3) ?
C8 C9 1.377(3) ?
C8 H8 0.93 ?
C9 C10 1.371(3) ?
C9 N3 1.468(3) y
C10 C11 1.371(3) ?
C10 H10 0.93 ?
C11 C12 1.374(3) ?
C11 H11 0.93 ?
C12 H12 0.93 ?
C13 C14 1.382(3) ?
C13 C18 1.385(3) ?
C13 S1 1.767(2) y
C14 C15 1.379(3) ?
C14 H14 0.93 ?
C15 C16 1.381(4) ?
C15 H15 0.93 ?
C16 C17 1.379(3) ?
C16 C19 1.505(4) ?
C17 C18 1.378(3) ?
C17 H17 0.93 ?
C18 H18 0.93 ?
C19 H19A 0.96 ?
C19 H19B 0.96 ?
C19 H19C 0.96 ?
N1 S1 1.631(2) y
N3 O3 1.212(3) y
N3 O4 1.221(2) y
O1 S1 1.428(2) y
O2 S1 1.425(2) 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
C4 H4A O4 1_556 0.97 2.56 3.431(3) 150
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 C5 -106.4(2)
N1 C1 C2 C3 8.3(2)
C5 C2 C3 N2 15.9(2)
C1 C2 C3 N2 -106.11(18)
C5 C2 C3 C4 135.79(18)
C1 C2 C3 C4 13.8(2)
N2 C3 C4 N1 82.83(18)
C2 C3 C4 N1 -30.55(19)
C1 C2 C5 C6 83.5(2)
C3 C2 C5 C6 -31.8(2)
C2 C5 C6 N2 35.3(2)
N2 C7 C8 C9 -178.37(18)
C12 C7 C8 C9 1.4(3)
C7 C8 C9 C10 0.1(3)
C7 C8 C9 N3 -179.20(17)
C8 C9 C10 C11 -1.1(3)
N3 C9 C10 C11 178.15(19)
C9 C10 C11 C12 0.7(3)
C10 C11 C12 C7 0.8(3)
N2 C7 C12 C11 178.0(2)
C8 C7 C12 C11 -1.8(3)
C18 C13 C14 C15 -0.7(3)
S1 C13 C14 C15 -178.18(17)
C13 C14 C15 C16 0.4(3)
C14 C15 C16 C17 0.0(3)
C14 C15 C16 C19 -178.8(2)
C15 C16 C17 C18 -0.2(3)
C19 C16 C17 C18 178.6(2)
C16 C17 C18 C13 -0.1(3)
C14 C13 C18 C17 0.5(3)
S1 C13 C18 C17 178.01(16)
C3 C4 N1 C1 36.99(19)
C3 C4 N1 S1 173.41(12)
C2 C1 N1 C4 -28.6(2)
C2 C1 N1 S1 -165.45(14)
C8 C7 N2 C6 3.5(3)
C12 C7 N2 C6 -176.3(2)
C8 C7 N2 C3 -166.94(18)
C12 C7 N2 C3 13.3(3)
C5 C6 N2 C7 162.14(19)
C5 C6 N2 C3 -26.4(2)
C4 C3 N2 C7 63.9(2)
C2 C3 N2 C7 178.17(17)
C4 C3 N2 C6 -107.5(2)
C2 C3 N2 C6 6.8(2)
C10 C9 N3 O3 179.7(2)
C8 C9 N3 O3 -1.1(3)
C10 C9 N3 O4 -1.3(3)
C8 C9 N3 O4 178.0(2)
C4 N1 S1 O2 47.77(16)
C1 N1 S1 O2 179.94(15)
C4 N1 S1 O1 177.06(14)
C1 N1 S1 O1 -50.76(17)
C4 N1 S1 C13 -67.77(16)
C1 N1 S1 C13 64.41(17)
C14 C13 S1 O2 -28.86(19)
C18 C13 S1 O2 153.66(17)
C14 C13 S1 O1 -160.24(16)
C18 C13 S1 O1 22.28(19)
C14 C13 S1 N1 85.70(18)
C18 C13 S1 N1 -91.78(18)
