#------------------------------------------------------------------------------
#$Date: 2009-11-23 07:50:56 +0200 (Mon, 23 Nov 2009) $
#$Revision: 903 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2218174.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_2218174
loop_
_publ_author_name
'Ramachandran, G.'
'Kanakam, Charles Christopher'
'Manivannan, V.'
_publ_section_title
;
 2,4-Dinitro-1-naphthyl 4-toluenesulfonate
;
_journal_coeditor_code           IS2287
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o873
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C17 H12 N2 O7 S'
_chemical_formula_moiety         'C17 H12 N2 O7 S'
_chemical_formula_sum            'C17 H12 N2 O7 S'
_chemical_formula_weight         388.35
_chemical_name_systematic
;
2,4-Dinitro-1-naphthyl 4-toluenesulfonate
;
_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                 90.757(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.071(2)
_cell_length_b                   7.8660(13)
_cell_length_c                   16.595(3)
_cell_measurement_reflns_used    4023
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25.2
_cell_measurement_theta_min      1.8
_cell_volume                     1706.0(5)
_computing_cell_refinement       'APEX2 (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'APEX2 (Bruker, 2004)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Kappa APEXII'
_diffrn_measurement_method       '\w and \f'
_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  0.0306
_diffrn_reflns_av_sigmaI/netI    0.0308
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12222
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.45
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.235
_exptl_absorpt_correction_T_max  0.9701
_exptl_absorpt_correction_T_min  0.9202
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(<i>SADABS</i>; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.234
_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     245
_refine_ls_number_reflns         3116
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0439
_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/[\s^2^(Fo^2^)+(0.0486P)^2^+0.4765P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0958
_refine_ls_wR_factor_ref         0.1043
_reflns_number_gt                2291
_reflns_number_total             3116
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    is2287.cif
_[local]_cod_data_source_block   I
_[local]_cod_cif_authors_sg_H-M  'P 21/c'
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_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_
_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
S S1 0.75961(5) 0.14928(8) 0.91732(3) 0.04636(19) Uani d . 1
N N2 0.47400(18) 0.4441(3) 1.21402(12) 0.0509(5) Uani d . 1
N N1 0.77051(15) 0.1383(3) 1.12836(11) 0.0511(5) Uani d . 1
C C8 0.62399(17) 0.1694(3) 1.03092(12) 0.0379(5) Uani d . 1
C C9 0.66905(17) 0.2018(3) 1.10432(13) 0.0396(5) Uani d . 1
C C10 0.61838(18) 0.2985(3) 1.16206(13) 0.0418(5) Uani d . 1
H H10 0.6505 0.3244 1.2109 0.050 Uiso calc R 1
C C11 0.52268(18) 0.3540(3) 1.14659(12) 0.0394(5) Uani d . 1
C C12 0.47017(17) 0.3258(3) 1.07210(12) 0.0383(5) Uani d . 1
C C13 0.52516(16) 0.2336(3) 1.01249(12) 0.0366(5) Uani d . 1
C C14 0.37180(18) 0.3875(3) 1.05167(14) 0.0462(6) Uani d . 1
H H14 0.3347 0.4476 1.0897 0.055 Uiso calc R 1
C C15 0.33082(18) 0.3603(3) 0.97732(15) 0.0502(6) Uani d . 1
H H15 0.2658 0.4016 0.9651 0.060 Uiso calc R 1
C C16 0.38494(19) 0.2709(3) 0.91879(15) 0.0494(6) Uani d . 1
H H16 0.3558 0.2542 0.8680 0.059 Uiso calc R 1
C C17 0.47966(18) 0.2082(3) 0.93546(13) 0.0421(5) Uani d . 1
H H17 0.5148 0.1484 0.8962 0.051 Uiso calc R 1
C C1 0.82025(17) -0.0380(3) 0.88993(14) 0.0467(6) Uani d . 1
C C4 0.9179(2) -0.3362(4) 0.84598(18) 0.0639(7) Uani d . 1
C C2 0.8941(2) -0.1075(4) 0.94025(17) 0.0660(8) Uani d . 1
H H2 0.9113 -0.0548 0.9888 0.079 Uiso calc R 1
C C3 0.9421(2) -0.2557(4) 0.91778(19) 0.0744(9) Uani d . 1
H H3 0.9918 -0.3026 0.9516 0.089 Uiso calc R 1
C C6 0.7943(2) -0.1167(4) 0.81845(15) 0.0583(7) Uani d . 1
H H6 0.7439 -0.0708 0.7848 0.070 Uiso calc R 1
C C5 0.8437(2) -0.2639(4) 0.79741(18) 0.0671(8) Uani d . 1
H H5 0.8264 -0.3163 0.7489 0.081 Uiso calc R 1
C C7 0.9719(2) -0.4974(4) 0.8216(2) 0.0947(11) Uani d . 1
H H7A 1.0222 -0.4715 0.7818 0.142 Uiso calc R 1
H H7B 0.9230 -0.5762 0.7995 0.142 Uiso calc R 1
H H7C 1.0049 -0.5470 0.8680 0.142 Uiso calc R 1
O O1 0.70983(14) 0.2246(2) 0.84979(9) 0.0613(5) Uani d . 1
O O2 0.82266(13) 0.2523(2) 0.96766(10) 0.0584(5) Uani d . 1
O O3 0.67103(11) 0.06829(18) 0.97377(8) 0.0431(4) Uani d . 1
O O4 0.82359(15) 0.2326(3) 1.16921(12) 0.0810(6) Uani d . 1
O O5 0.79512(14) -0.0046(3) 1.10830(11) 0.0644(5) Uani d . 1
O O6 0.53013(16) 0.5300(3) 1.25734(11) 0.0738(6) Uani d . 1
O O7 0.38300(16) 0.4246(3) 1.22514(11) 0.0713(6) Uani d . 1
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
S1 0.0527(4) 0.0503(4) 0.0362(3) -0.0065(3) 0.0072(3) -0.0017(3)
N2 0.0698(15) 0.0451(12) 0.0382(11) 0.0054(11) 0.0093(11) 0.0005(9)
N1 0.0516(13) 0.0644(15) 0.0372(11) -0.0010(12) -0.0001(9) 0.0005(11)
C8 0.0473(13) 0.0341(12) 0.0324(11) -0.0068(10) 0.0055(10) 0.0000(9)
C9 0.0447(13) 0.0384(12) 0.0358(12) -0.0044(10) 0.0001(10) 0.0041(10)
C10 0.0582(15) 0.0389(12) 0.0285(11) -0.0081(11) 0.0000(10) 0.0002(10)
C11 0.0532(14) 0.0313(11) 0.0338(11) -0.0022(10) 0.0087(10) 0.0017(9)
C12 0.0485(13) 0.0300(11) 0.0364(12) -0.0069(10) 0.0043(10) 0.0048(9)
C13 0.0446(13) 0.0309(11) 0.0344(11) -0.0090(10) 0.0013(10) 0.0028(9)
C14 0.0521(14) 0.0383(13) 0.0485(14) -0.0017(11) 0.0078(11) 0.0060(11)
C15 0.0448(14) 0.0490(14) 0.0566(15) -0.0038(11) -0.0045(12) 0.0106(13)
C16 0.0564(15) 0.0488(14) 0.0427(13) -0.0126(12) -0.0088(12) 0.0061(11)
C17 0.0517(14) 0.0394(12) 0.0352(12) -0.0088(11) 0.0001(10) 0.0011(10)
C1 0.0405(13) 0.0579(15) 0.0420(13) -0.0071(11) 0.0076(11) -0.0057(11)
C4 0.0484(15) 0.0653(18) 0.078(2) -0.0063(14) 0.0158(14) -0.0175(16)
C2 0.0531(16) 0.087(2) 0.0578(16) 0.0052(15) -0.0036(13) -0.0213(15)
C3 0.0555(17) 0.089(2) 0.079(2) 0.0164(16) -0.0041(15) -0.0103(18)
C6 0.0564(16) 0.0690(18) 0.0496(15) 0.0026(14) 0.0009(12) -0.0111(13)
C5 0.0612(17) 0.076(2) 0.0641(18) -0.0081(15) 0.0040(14) -0.0264(16)
C7 0.075(2) 0.077(2) 0.133(3) 0.0067(18) 0.022(2) -0.028(2)
O1 0.0794(12) 0.0660(12) 0.0387(9) 0.0039(9) 0.0059(9) 0.0086(8)
O2 0.0630(11) 0.0584(11) 0.0539(10) -0.0189(9) 0.0080(8) -0.0100(9)
O3 0.0514(9) 0.0404(9) 0.0377(8) -0.0031(7) 0.0076(7) -0.0054(7)
O4 0.0617(12) 0.1075(17) 0.0734(13) -0.0049(11) -0.0180(11) -0.0267(12)
O5 0.0660(12) 0.0632(12) 0.0640(12) 0.0149(10) -0.0005(9) 0.0042(10)
O6 0.0898(15) 0.0723(13) 0.0593(12) 0.0021(11) 0.0009(11) -0.0308(10)
O7 0.0664(13) 0.0885(15) 0.0596(12) 0.0031(11) 0.0229(10) -0.0065(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O1 1.4179(17)
S1 O2 1.4196(16)
S1 O3 1.6287(16)
S1 C1 1.736(3)
N2 O7 1.216(3)
N2 O6 1.224(3)
N2 C11 1.476(3)
N1 O4 1.216(3)
N1 O5 1.216(3)
N1 C9 1.467(3)
C8 C9 1.370(3)
C8 O3 1.388(2)
C8 C13 1.416(3)
C9 C10 1.397(3)
C10 C11 1.346(3)
C10 H10 0.9300
C11 C12 1.423(3)
C12 C14 1.411(3)
C12 C13 1.429(3)
C13 C17 1.417(3)
C14 C15 1.356(3)
C14 H14 0.9300
C15 C16 1.399(3)
C15 H15 0.9300
C16 C17 1.358(3)
C16 H16 0.9300
C17 H17 0.9300
C1 C6 1.377(3)
C1 C2 1.381(3)
C4 C5 1.376(4)
C4 C3 1.382(4)
C4 C7 1.509(4)
C2 C3 1.378(4)
C2 H2 0.9300
C3 H3 0.9300
C6 C5 1.373(4)
C6 H6 0.9300
C5 H5 0.9300
C7 H7A 0.9600
C7 H7B 0.9600
C7 H7C 0.9600
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 S1 O2 118.91(11)
O1 S1 O3 107.20(10)
O2 S1 O3 107.24(9)
O1 S1 C1 110.71(11)
O2 S1 C1 112.01(11)
O3 S1 C1 98.58(10)
O7 N2 O6 124.1(2)
O7 N2 C11 119.1(2)
O6 N2 C11 116.7(2)
O4 N1 O5 124.4(2)
O4 N1 C9 116.8(2)
O5 N1 C9 118.8(2)
C9 C8 O3 121.7(2)
C9 C8 C13 120.4(2)
O3 C8 C13 117.89(18)
C8 C9 C10 120.6(2)
C8 C9 N1 123.7(2)
C10 C9 N1 115.71(19)
C11 C10 C9 119.6(2)
C11 C10 H10 120.2
C9 C10 H10 120.2
C10 C11 C12 123.4(2)
C10 C11 N2 114.8(2)
C12 C11 N2 121.7(2)
C14 C12 C11 125.6(2)
C14 C12 C13 118.3(2)
C11 C12 C13 116.1(2)
C8 C13 C17 121.0(2)
C8 C13 C12 119.83(19)
C17 C13 C12 119.1(2)
C15 C14 C12 120.8(2)
C15 C14 H14 119.6
C12 C14 H14 119.6
C14 C15 C16 120.9(2)
C14 C15 H15 119.5
C16 C15 H15 119.5
C17 C16 C15 120.6(2)
C17 C16 H16 119.7
C15 C16 H16 119.7
C16 C17 C13 120.2(2)
C16 C17 H17 119.9
C13 C17 H17 119.9
C6 C1 C2 120.4(2)
C6 C1 S1 119.9(2)
C2 C1 S1 119.70(19)
C5 C4 C3 117.8(3)
C5 C4 C7 121.3(3)
C3 C4 C7 120.9(3)
C3 C2 C1 119.2(3)
C3 C2 H2 120.4
C1 C2 H2 120.4
C2 C3 C4 121.4(3)
C2 C3 H3 119.3
C4 C3 H3 119.3
C5 C6 C1 119.2(3)
C5 C6 H6 120.4
C1 C6 H6 120.4
C6 C5 C4 122.0(3)
C6 C5 H5 119.0
C4 C5 H5 119.0
C4 C7 H7A 109.5
C4 C7 H7B 109.5
H7A C7 H7B 109.5
C4 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
C8 O3 S1 119.58(13)
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
O3 C8 C9 C10 -177.46(19)
C13 C8 C9 C10 0.0(3)
O3 C8 C9 N1 1.8(3)
C13 C8 C9 N1 179.21(19)
O4 N1 C9 C8 143.2(2)
O5 N1 C9 C8 -38.6(3)
O4 N1 C9 C10 -37.5(3)
O5 N1 C9 C10 140.7(2)
C8 C9 C10 C11 2.9(3)
N1 C9 C10 C11 -176.4(2)
C9 C10 C11 C12 -2.8(3)
C9 C10 C11 N2 175.77(19)
O7 N2 C11 C10 -143.1(2)
O6 N2 C11 C10 34.3(3)
O7 N2 C11 C12 35.5(3)
O6 N2 C11 C12 -147.1(2)
C10 C11 C12 C14 -177.1(2)
N2 C11 C12 C14 4.5(3)
C10 C11 C12 C13 -0.1(3)
N2 C11 C12 C13 -178.59(19)
C9 C8 C13 C17 176.87(19)
O3 C8 C13 C17 -5.6(3)
C9 C8 C13 C12 -2.9(3)
O3 C8 C13 C12 174.60(17)
C14 C12 C13 C8 -179.86(19)
C11 C12 C13 C8 3.0(3)
C14 C12 C13 C17 0.3(3)
C11 C12 C13 C17 -176.83(19)
C11 C12 C14 C15 176.7(2)
C13 C12 C14 C15 -0.2(3)
C12 C14 C15 C16 -0.2(3)
C14 C15 C16 C17 0.5(3)
C15 C16 C17 C13 -0.3(3)
C8 C13 C17 C16 -179.9(2)
C12 C13 C17 C16 -0.1(3)
O1 S1 C1 C6 -17.0(2)
O2 S1 C1 C6 -152.30(19)
O3 S1 C1 C6 95.1(2)
O1 S1 C1 C2 163.2(2)
O2 S1 C1 C2 27.9(2)
O3 S1 C1 C2 -84.7(2)
C6 C1 C2 C3 0.5(4)
S1 C1 C2 C3 -179.7(2)
C1 C2 C3 C4 0.0(5)
C5 C4 C3 C2 -0.3(4)
C7 C4 C3 C2 179.2(3)
C2 C1 C6 C5 -0.8(4)
S1 C1 C6 C5 179.4(2)
C1 C6 C5 C4 0.6(4)
C3 C4 C5 C6 0.0(4)
C7 C4 C5 C6 -179.5(3)
C9 C8 O3 S1 -80.6(2)
C13 C8 O3 S1 101.93(19)
O1 S1 O3 C8 -86.68(17)
O2 S1 O3 C8 42.07(17)
C1 S1 O3 C8 158.41(16)
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
_geom_hbond_publ_flag
C2 H2 O5 . 0.93 2.55 3.194(3) 127 Y
C14 H14 O7 . 0.93 2.33 2.895(3) 119 Y
C17 H17 O3 . 0.93 2.48 2.798(3) 100 Y
C10 H10 O1 4_566 0.93 2.45 3.327(3) 157 Y