#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/55/2015502.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_2015502
loop_
_publ_author_name
'Brito, Iván'
'López-Rodríguez, Matías'
'Cárdenas, Alejandro'
'Vargas, Danitza'
_publ_section_title
;
 4-(2,4-Dinitrophenylsulfanyl)morpholine
;
_journal_coeditor_code           HJ3013
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o461
_journal_page_last               o463
_journal_paper_doi               10.1107/S0108270106021524
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C10 H11 N3 O5 S'
_chemical_formula_moiety         'C10 H11 N3 O5 S'
_chemical_formula_sum            'C10 H11 N3 O5 S'
_chemical_formula_weight         285.28
_chemical_melting_point          196.4
_chemical_name_systematic
;
4-(2,4-Dinitrophenylsulfanyl)morpholine
;
_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'
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 97.4900(16)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.4280(2)
_cell_length_b                   16.0850(7)
_cell_length_c                   12.1500(6)
_cell_measurement_reflns_used    6390
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.90
_cell_measurement_theta_min      2.12
_cell_volume                     1245.52(9)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction        DENZO-SMN
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al.,  1999)'
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector'
_diffrn_measurement_method       'φ scans, and ω scans with κ  offsets'
_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  0.0861
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7918
_diffrn_reflns_theta_full        27.92
_diffrn_reflns_theta_max         27.92
_diffrn_reflns_theta_min         2.11
_exptl_absorpt_coefficient_mu    0.281
_exptl_absorpt_correction_T_max  0.950
_exptl_absorpt_correction_T_min  0.915
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SORTAV; Blessing, 1995)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.521
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.374
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2901
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.122
_refine_ls_R_factor_gt           0.0692
_refine_ls_shift/su_max          0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.1026P)²+0.3584P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.2058
_reflns_number_gt                2311
_reflns_number_total             2901
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hj3013.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2015502
_cod_database_fobs_code          2015502
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
S S1 -0.28752(10) 0.07516(5) 0.57249(6) 0.0556(3) Uani d . 1
O O1 -0.1272(4) -0.06892(13) 0.8830(2) 0.0744(7) Uani d . 1
O O2 -0.4449(4) 0.14649(19) 0.3893(2) 0.0884(8) Uani d . 1
O O3 -0.3347(4) 0.24689(18) 0.2970(2) 0.0899(8) Uani d . 1
O O4 0.5261(3) 0.32752(16) 0.5449(2) 0.0762(7) Uani d . 1
O O5 0.3200(4) 0.37217(15) 0.40325(19) 0.0720(6) Uani d . 1
N N1 -0.1800(3) 0.03842(14) 0.69808(18) 0.0514(6) Uani d . 1
N N2 -0.3142(3) 0.19874(16) 0.37465(19) 0.0554(6) Uani d . 1
N N3 0.3595(3) 0.32676(15) 0.4839(2) 0.0526(6) Uani d . 1
C C1 0.0267(5) -0.0637(2) 0.8098(3) 0.0702(9) Uani d . 1
H H1A 0.0982 -0.1167 0.8082 0.084 Uiso calc R 1
H H1B 0.13 -0.0221 0.8368 0.084 Uiso calc R 1
C C2 -0.0696(5) -0.04138(18) 0.6945(3) 0.0597(7) Uani d . 1
H H2A 0.0388 -0.0369 0.6463 0.072 Uiso calc R 1
H H2B -0.1674 -0.0843 0.6652 0.072 Uiso calc R 1
C C3 -0.3366(5) 0.03413(18) 0.7767(3) 0.0617(8) Uani d . 1
H H3A -0.4447 -0.0059 0.7506 0.074 Uiso calc R 1
H H3B -0.4025 0.088 0.7817 0.074 Uiso calc R 1
C C4 -0.2309(6) 0.0090(2) 0.8872(3) 0.0729(9) Uani d . 1
H H4A -0.1293 0.0511 0.9147 0.088 Uiso calc R 1
H H4B -0.334 0.0052 0.9386 0.088 Uiso calc R 1
C C5 -0.1028(3) 0.15150(14) 0.54972(19) 0.0397(5) Uani d . 1
C C6 -0.1267(3) 0.20323(15) 0.45573(18) 0.0407(5) Uani d . 1
C C7 0.0213(3) 0.26079(15) 0.43413(19) 0.0414(5) Uani d . 1
H H7 0.0006 0.2942 0.3712 0.05 Uiso calc R 1
C C8 0.2000(3) 0.26718(15) 0.50838(19) 0.0401(5) Uani d . 1
C C9 0.2318(3) 0.21931(17) 0.60350(19) 0.0449(6) Uani d . 1
H H9 0.3536 0.2255 0.6533 0.054 Uiso calc R 1
C C10 0.0820(4) 0.16247(15) 0.62395(19) 0.0437(5) Uani d . 1
H H10 0.1032 0.1306 0.6883 0.052 Uiso calc R 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'
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 S1 C5 100.41(11) y
C1 O1 C4 109.8(2) y
C2 N1 C3 110.5(2) y
C2 N1 S1 114.76(19) y
C3 N1 S1 111.44(19) y
O3 N2 O2 123.1(2) ?
O3 N2 C6 119.4(2) ?
O2 N2 C6 117.5(2) ?
O4 N3 O5 123.7(2) ?
O4 N3 C8 117.8(2) ?
O5 N3 C8 118.5(2) ?
O1 C1 C2 111.3(3) ?
O1 C1 H1A 109.4 ?
C2 C1 H1A 109.4 ?
O1 C1 H1B 109.4 ?
C2 C1 H1B 109.4 ?
H1A C1 H1B 108 ?
N1 C2 C1 108.9(2) ?
N1 C2 H2A 109.9 ?
C1 C2 H2A 109.9 ?
N1 C2 H2B 109.9 ?
C1 C2 H2B 109.9 ?
H2A C2 H2B 108.3 ?
N1 C3 C4 109.2(3) ?
N1 C3 H3A 109.8 ?
C4 C3 H3A 109.8 ?
N1 C3 H3B 109.8 ?
C4 C3 H3B 109.8 ?
H3A C3 H3B 108.3 ?
O1 C4 C3 111.7(3) ?
O1 C4 H4A 109.3 ?
C3 C4 H4A 109.3 ?
O1 C4 H4B 109.3 ?
C3 C4 H4B 109.3 ?
H4A C4 H4B 107.9 ?
C6 C5 C10 116.2(2) ?
C6 C5 S1 122.54(17) ?
C10 C5 S1 121.28(19) ?
C7 C6 C5 123.2(2) ?
C7 C6 N2 115.9(2) ?
C5 C6 N2 120.9(2) ?
C8 C7 C6 117.8(2) ?
C8 C7 H7 121.1 ?
C6 C7 H7 121.1 ?
C7 C8 C9 122.0(2) ?
C7 C8 N3 117.8(2) ?
C9 C8 N3 120.3(2) ?
C10 C9 C8 119.4(2) ?
C10 C9 H9 120.3 ?
C8 C9 H9 120.3 ?
C9 C10 C5 121.4(2) ?
C9 C10 H10 119.3 ?
C5 C10 H10 119.3 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 N1 1.697(2) y
S1 C5 1.755(2) y
O1 C1 1.417(4) ?
O1 C4 1.423(4) ?
O2 N2 1.218(3) ?
O3 N2 1.214(3) ?
O4 N3 1.220(3) ?
O5 N3 1.222(3) ?
N1 C2 1.470(4) ?
N1 C3 1.477(3) ?
N2 C6 1.456(3) y
N3 C8 1.462(3) y
C1 C2 1.500(5) ?
C1 H1A 0.97 ?
C1 H1B 0.97 ?
C2 H2A 0.97 ?
C2 H2B 0.97 ?
C3 C4 1.481(5) ?
C3 H3A 0.97 ?
C3 H3B 0.97 ?
C4 H4A 0.97 ?
C4 H4B 0.97 ?
C5 C6 1.405(3) ?
C5 C10 1.406(3) ?
C6 C7 1.377(3) ?
C7 C8 1.369(3) ?
C7 H7 0.93 ?
C8 C9 1.382(3) ?
C9 C10 1.374(3) ?
C9 H9 0.93 ?
C10 H10 0.93 ?
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
C3 H3B O5 4_466 0.97 2.54 3.224(4) 127 yes
C9 H9 O3 4_666 0.93 2.52 3.446(4) 174 yes
C10 H10 N1 . 0.93 2.36 2.833(3) 111 yes
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
C5 S1 N1 C2 -102.4(2)
C5 S1 N1 C3 131.02(18)
C4 O1 C1 C2 -59.9(4)
C3 N1 C2 C1 -56.0(3)
S1 N1 C2 C1 176.94(19)
O1 C1 C2 N1 58.2(3)
C2 N1 C3 C4 56.1(3)
S1 N1 C3 C4 -175.0(2)
C1 O1 C4 C3 60.1(4)
N1 C3 C4 O1 -58.0(4)
N1 S1 C5 C6 -177.40(18)
N1 S1 C5 C10 4.5(2)
C10 C5 C6 C7 1.2(3)
S1 C5 C6 C7 -176.94(17)
C10 C5 C6 N2 -178.5(2)
S1 C5 C6 N2 3.3(3)
O3 N2 C6 C7 -3.2(3)
O2 N2 C6 C7 177.5(2)
O3 N2 C6 C5 176.6(2)
O2 N2 C6 C5 -2.7(3)
C5 C6 C7 C8 0.2(3)
N2 C6 C7 C8 179.9(2)
C6 C7 C8 C9 -1.4(3)
C6 C7 C8 N3 178.42(19)
O4 N3 C8 C7 -173.9(2)
O5 N3 C8 C7 5.3(3)
O4 N3 C8 C9 5.9(4)
O5 N3 C8 C9 -174.9(2)
C7 C8 C9 C10 1.1(4)
N3 C8 C9 C10 -178.7(2)
C8 C9 C10 C5 0.4(4)
C6 C5 C10 C9 -1.5(3)
S1 C5 C10 C9 176.68(19)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 1456203
