#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/92/2019208.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_2019208
loop_
_publ_author_name
'Wade, Colin B.'
'Mohanty, Dillip K.'
'Squattrito, Philip J.'
'Amato, Nicholas J.'
'Kirschbaum, Kristin'
_publ_section_title
;
 A series of N-(2-phenylethyl)nitroaniline derivatives as
 precursors for slow and sustained nitric oxide release agents
;
_journal_coeditor_code           CU3041
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1383
_journal_page_last               1389
_journal_paper_doi               10.1107/S0108270113025869
_journal_volume                  69
_journal_year                    2013
_chemical_formula_moiety         'C15 H16 N2 O4 S'
_chemical_formula_sum            'C15 H16 N2 O4 S'
_chemical_formula_weight         320.36
_chemical_melting_point          414
_chemical_name_common
4-(methylsulfonyl)-2-nitro-N-(2-phenylethyl)aniline
_chemical_name_systematic
;
4-(methylsulfonyl)-2-nitro-N-(2-phenylethyl)aniline
;
_space_group_IT_number           88
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  '-I 4ad'
_symmetry_space_group_name_H-M   'I 41/a :2'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   20.4639(13)
_cell_length_b                   20.4639(13)
_cell_length_c                   14.3952(14)
_cell_measurement_reflns_used    53474
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.86
_cell_measurement_theta_min      2.63
_cell_volume                     6028.3(8)
_computing_cell_refinement       'APEX2 (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'APEX2 (Bruker, 2005)'
_computing_molecular_graphics    'CrystalMaker (Palmer, 2013)'
_computing_publication_material  'APEX2 (Bruker, 2005)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker APEX DUO CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0181
_diffrn_reflns_av_sigmaI/netI    0.0090
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            52424
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         32.92
_diffrn_reflns_theta_min         1.73
_exptl_absorpt_coefficient_mu    0.235
_exptl_absorpt_correction_T_max  0.9546
_exptl_absorpt_correction_T_min  0.9120
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cuboid
_exptl_crystal_F_000             2688
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.507
_refine_diff_density_min         -0.306
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         5524
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0312
_refine_ls_R_factor_gt           0.0290
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0494P)²+3.0117P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0842
_refine_ls_wR_factor_ref         0.0863
_reflns_number_gt                5155
_reflns_number_total             5524
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cu3041.cif
_cod_data_source_block           C15H16N2O4S
_cod_original_cell_volume        6028.3(10)
_cod_original_sg_symbol_H-M      'I 41/a'
_cod_database_code               2019208
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-y+3/4, x+1/4, z+1/4'
'y+3/4, -x+3/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+5/4, x+3/4, z+3/4'
'y+5/4, -x+5/4, z+5/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-3/4, -x-1/4, -z-1/4'
'-y-3/4, x-3/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y-1/4, -x+1/4, -z+1/4'
'-y-1/4, x-1/4, -z-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_occupancy
_atom_site_symmetry_multiplicity
S S1 0.918999(8) 0.384073(8) 0.115221(13) 0.01486(5) Uani d 1 1
O O21 0.72956(3) 0.62358(3) 0.13034(5) 0.02619(14) Uani d 1 1
O O22 0.83430(3) 0.61924(3) 0.15113(5) 0.02251(12) Uani d 1 1
O O41 0.91451(3) 0.33599(3) 0.04188(4) 0.02179(12) Uani d 1 1
O O42 0.96848(3) 0.43425(3) 0.10731(5) 0.02180(12) Uani d 1 1
N N1 0.66040(3) 0.51537(3) 0.11584(5) 0.01679(12) Uani d 1 1
H H1 0.6604(7) 0.5584(8) 0.1202(10) 0.038(4) Uiso d 1 1
N N2 0.78132(3) 0.59202(3) 0.13760(5) 0.01652(11) Uani d 1 1
C C1 0.71927(3) 0.48639(3) 0.12182(5) 0.01391(12) Uani d 1 1
C C2 0.77942(3) 0.52165(3) 0.13051(5) 0.01370(12) Uani d 1 1
C C3 0.84001(3) 0.49002(3) 0.13130(5) 0.01447(12) Uani d 1 1
H H3 0.8791(7) 0.5168(6) 0.1359(9) 0.026(3) Uiso d 1 1
C C4 0.84249(3) 0.42282(3) 0.12432(5) 0.01465(12) Uani d 1 1
C C5 0.78421(4) 0.38584(4) 0.11955(5) 0.01666(13) Uani d 1 1
H H5 0.7859(6) 0.3384(6) 0.1168(8) 0.023(3) Uiso d 1 1
C C6 0.72458(4) 0.41678(4) 0.11892(5) 0.01637(13) Uani d 1 1
H H6 0.6879(6) 0.3928(6) 0.1145(9) 0.023(3) Uiso d 1 1
C C7 0.59791(4) 0.48089(4) 0.11108(5) 0.01798(13) Uani d 1 1
H H7A 0.5906(5) 0.4561(5) 0.1693(8) 0.015(2) Uiso d 1 1
H H7B 0.5982(6) 0.4507(6) 0.0597(8) 0.018(3) Uiso d 1 1
C C8 0.54312(4) 0.53117(4) 0.09737(5) 0.01863(13) Uani d 1 1
H H8A 0.5029(6) 0.5080(6) 0.0915(9) 0.021(3) Uiso d 1 1
H H8B 0.5525(6) 0.5542(6) 0.0391(9) 0.025(3) Uiso d 1 1
C C9 0.53881(3) 0.57928(4) 0.17680(5) 0.01547(12) Uani d 1 1
C C10 0.56452(4) 0.64241(4) 0.17008(5) 0.01871(13) Uani d 1 1
H H10 0.5853(6) 0.6565(7) 0.1136(9) 0.026(3) Uiso d 1 1
C C11 0.56197(4) 0.68488(4) 0.24613(6) 0.02200(15) Uani d 1 1
H H11 0.5775(6) 0.7276(7) 0.2407(10) 0.029(3) Uiso d 1 1
C C12 0.53446(4) 0.66439(4) 0.32954(6) 0.02297(15) Uani d 1 1
H H12 0.5339(7) 0.6937(7) 0.3812(10) 0.034(4) Uiso d 1 1
C C13 0.50872(4) 0.60148(4) 0.33686(5) 0.02155(14) Uani d 1 1
H H13 0.4898(7) 0.5856(7) 0.3950(10) 0.031(3) Uiso d 1 1
C C14 0.51036(4) 0.55957(4) 0.26071(5) 0.01777(13) Uani d 1 1
H H14 0.4927(6) 0.5155(6) 0.2656(9) 0.022(3) Uiso d 1 1
C C15 0.92951(4) 0.34181(4) 0.22080(6) 0.02208(14) Uani d 1 1
H H15A 0.9299(6) 0.3726(7) 0.2701(10) 0.031(3) Uiso d 1 1
H H15B 0.8929(7) 0.3095(7) 0.2271(10) 0.034(3) Uiso d 1 1
H H15C 0.9713(7) 0.3212(7) 0.2172(10) 0.037(4) Uiso 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'
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
O41 S1 O42 118.03(4)
O41 S1 C4 107.72(4)
O42 S1 C4 107.99(3)
O41 S1 C15 107.66(4)
O42 S1 C15 109.33(4)
C4 S1 C15 105.40(4)
C1 N1 C7 125.00(6)
C1 N1 H1 115.8(10)
C7 N1 H1 118.9(10)
O22 N2 O21 121.76(7)
O22 N2 C2 119.00(6)
O21 N2 C2 119.24(6)
N1 C1 C6 120.36(7)
N1 C1 C2 123.58(7)
C6 C1 C2 116.06(6)
C3 C2 C1 121.96(6)
C3 C2 N2 115.91(6)
C1 C2 N2 122.12(6)
C4 C3 C2 119.55(6)
C4 C3 H3 122.5(8)
C2 C3 H3 117.9(8)
C3 C4 C5 120.39(7)
C3 C4 S1 119.15(5)
C5 C4 S1 120.37(5)
C6 C5 C4 120.17(7)
C6 C5 H5 119.5(8)
C4 C5 H5 120.4(8)
C5 C6 C1 121.75(7)
C5 C6 H6 119.4(8)
C1 C6 H6 118.9(8)
N1 C7 C8 108.76(6)
N1 C7 H7A 109.9(6)
C8 C7 H7A 110.0(6)
N1 C7 H7B 109.8(7)
C8 C7 H7B 109.6(7)
H7A C7 H7B 108.8(10)
C9 C8 C7 112.47(6)
C9 C8 H8A 109.9(7)
C7 C8 H8A 108.0(7)
C9 C8 H8B 110.2(8)
C7 C8 H8B 106.9(7)
H8A C8 H8B 109.3(10)
C10 C9 C14 118.84(7)
C10 C9 C8 121.84(7)
C14 C9 C8 119.29(7)
C9 C10 C11 120.39(7)
C9 C10 H10 120.1(8)
C11 C10 H10 119.4(8)
C12 C11 C10 120.22(8)
C12 C11 H11 119.5(8)
C10 C11 H11 120.3(9)
C11 C12 C13 119.76(7)
C11 C12 H12 119.2(9)
C13 C12 H12 121.0(9)
C14 C13 C12 120.00(7)
C14 C13 H13 118.6(8)
C12 C13 H13 121.4(8)
C13 C14 C9 120.78(7)
C13 C14 H14 120.3(7)
C9 C14 H14 118.9(7)
S1 C15 H15A 108.7(8)
S1 C15 H15B 108.1(8)
H15A C15 H15B 112.0(11)
S1 C15 H15C 106.2(9)
H15A C15 H15C 109.1(12)
H15B C15 H15C 112.6(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O41 1.4462(6)
S1 O42 1.4467(6)
S1 C4 1.7599(7)
S1 C15 1.7619(8)
O21 N2 1.2449(9)
O22 N2 1.2345(9)
N1 C1 1.3454(9)
N1 C7 1.4623(10)
N1 H1 0.882(16)
N2 C2 1.4441(9)
C1 C6 1.4293(10)
C1 C2 1.4322(10)
C2 C3 1.3989(10)
C3 C4 1.3797(10)
C3 H3 0.973(14)
C4 C5 1.4142(10)
C5 C6 1.3746(10)
C5 H5 0.972(13)
C6 H6 0.898(13)
C7 C8 1.5344(11)
C7 H7A 0.992(11)
C7 H7B 0.964(12)
C8 C9 1.5114(10)
C8 H8A 0.954(12)
C8 H8B 0.982(13)
C9 C10 1.3983(11)
C9 C14 1.4002(10)
C10 C11 1.3989(11)
C10 H10 0.962(13)
C11 C12 1.3909(12)
C11 H11 0.934(13)
C12 C13 1.3949(12)
C12 H12 0.955(14)
C13 C14 1.3922(11)
C13 H13 0.977(14)
C14 H14 0.974(12)
C15 H15A 0.949(14)
C15 H15B 1.003(14)
C15 H15C 0.955(14)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1 O21 0.882(16) 1.951(16) 2.6364(9) 133.4(14)
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
C7 N1 C1 C6 3.38(11)
C7 N1 C1 C2 -177.13(7)
N1 C1 C2 C3 -176.34(7)
C6 C1 C2 C3 3.18(10)
N1 C1 C2 N2 2.73(11)
C6 C1 C2 N2 -177.76(6)
O22 N2 C2 C3 -5.65(10)
O21 N2 C2 C3 174.68(7)
O22 N2 C2 C1 175.24(7)
O21 N2 C2 C1 -4.44(10)
C1 C2 C3 C4 -0.55(10)
N2 C2 C3 C4 -179.66(6)
C2 C3 C4 C5 -2.14(10)
C2 C3 C4 S1 174.53(5)
O41 S1 C4 C3 -134.28(6)
O42 S1 C4 C3 -5.78(7)
C15 S1 C4 C3 110.98(6)
O41 S1 C4 C5 42.39(7)
O42 S1 C4 C5 170.88(6)
C15 S1 C4 C5 -72.35(7)
C3 C4 C5 C6 2.03(11)
S1 C4 C5 C6 -174.59(6)
C4 C5 C6 C1 0.80(11)
N1 C1 C6 C5 176.24(7)
C2 C1 C6 C5 -3.29(10)
C1 N1 C7 C8 -175.70(7)
N1 C7 C8 C9 -61.20(8)
C7 C8 C9 C10 101.15(8)
C7 C8 C9 C14 -76.55(8)
C14 C9 C10 C11 0.21(11)
C8 C9 C10 C11 -177.50(7)
C9 C10 C11 C12 0.74(12)
C10 C11 C12 C13 -0.70(12)
C11 C12 C13 C14 -0.30(12)
C12 C13 C14 C9 1.27(12)
C10 C9 C14 C13 -1.21(11)
C8 C9 C14 C13 176.56(7)
