# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2009

data_I
_database_code_depnum_ccdc_archive 'CCDC 677516'
_audit_creation_method SHELXL97
_chemical_name_systematic
;
<i>N</i>-(2-Chloro-2-nitro-1-phenylpropyl)-4-methylbenzenesulfonamide
;

_chemical_name_common ?
_chemical_formula_moiety 'C16 H17 Cl N2 O4 S'
_chemical_formula_sum 'C16 H17 Cl N2 O4 S'
_chemical_formula_iupac 'C16 H17 Cl N2 O4 S'
_chemical_formula_weight 368.83
_chemical_melting_point 423.2
_symmetry_cell_setting orthorhombic
_symmetry_space_group_name_H-M 'P b c a'
_symmetry_space_group_name_Hall '-P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz

'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'


_cell_length_a 7.8254(8)

_cell_length_b 19.610(2)

_cell_length_c 22.533(3)

_cell_angle_alpha 90.00

_cell_angle_beta 90.00

_cell_angle_gamma 90.00

_cell_volume 3457.8(7)

_cell_formula_units_Z 8

_cell_measurement_reflns_used 7468

_cell_measurement_theta_min 2.26

_cell_measurement_theta_max 27.93

_cell_measurement_temperature 291(2)

_exptl_crystal_description block

_exptl_crystal_colour colourless

_exptl_crystal_size_max 0.30

_exptl_crystal_size_mid 0.26

_exptl_crystal_size_min 0.24

_exptl_crystal_density_diffrn 1.417

_exptl_crystal_density_meas ?

_exptl_crystal_density_method 'not measured'

_exptl_crystal_F_000 1536

_exptl_absorpt_coefficient_mu 0.364

_exptl_absorpt_correction_type multi-scan

_exptl_absorpt_process_details '(SADABS; Bruker, 2000)'

_exptl_absorpt_correction_T_min 0.901

_exptl_absorpt_correction_T_max 0.921

_exptl_special_details
;
;


_diffrn_ambient_temperature 291(2)

_diffrn_radiation_type MoK\a

_diffrn_radiation_wavelength 0.71073

_diffrn_radiation_source 'sealed tube'

_diffrn_radiation_monochromator graphite

_diffrn_measurement_device_type 'Bruker SMART APEX CCD area-detector'

_diffrn_measurement_method '\f and \w'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number 17527

_diffrn_reflns_av_R_equivalents 0.0702

_diffrn_reflns_av_sigmaI/netI 0.0651

_diffrn_reflns_theta_min 2.08

_diffrn_reflns_theta_max 26.00

_diffrn_reflns_theta_full 26.00

_diffrn_measured_fraction_theta_max 1.000

_diffrn_measured_fraction_theta_full 1.000

_diffrn_reflns_limit_h_min -9

_diffrn_reflns_limit_h_max 8

_diffrn_reflns_limit_k_min -24

_diffrn_reflns_limit_k_max 24

_diffrn_reflns_limit_l_min -16

_diffrn_reflns_limit_l_max 27

_diffrn_standards_number ?

_diffrn_standards_interval_count ?

_diffrn_standards_interval_time ?

_diffrn_standards_decay_% ?

_reflns_number_total 3396

_reflns_number_gt 2467

_reflns_threshold_expression I>2\s(I)

_refine_ls_structure_factor_coef Fsqd

_refine_ls_matrix_type full

_refine_ls_R_factor_all 0.0782

_refine_ls_R_factor_gt 0.0563

_refine_ls_wR_factor_gt 0.1203

_refine_ls_wR_factor_ref 0.1251

_refine_ls_goodness_of_fit_ref 1.012

_refine_ls_restrained_S_all 1.012

_refine_ls_number_reflns 3396

_refine_ls_number_parameters 222

_refine_ls_number_restraints 0

_refine_ls_hydrogen_treatment mixed

_refine_ls_weighting_scheme calc

_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.06P)^2^+0.58P] where P=(Fo^2^+2Fc^2^)/3'

_atom_sites_solution_hydrogens geom

_atom_sites_solution_primary direct

_atom_sites_solution_secondary difmap

_refine_ls_shift/su_max 0.000

_refine_ls_shift/su_mean 0.000

_refine_diff_density_max 0.276

_refine_diff_density_min -0.262

_refine_ls_extinction_method none

_refine_ls_extinction_coef ?

_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'


_computing_data_collection 'SMART (Bruker, 2000)'

_computing_cell_refinement 'SMART (Bruker, 2000)'

_computing_data_reduction 'SAINT (Bruker, 2000)'

_computing_structure_solution 'SHELXTL (Bruker, 2000)'

_computing_structure_refinement 'SHELXTL (Bruker, 2000)'

_computing_molecular_graphics 'SHELXTL (Bruker, 2000)'

_computing_publication_material
'SHELXTL (Bruker, 2000) and PLATON (Spek, 2003)'
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
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group

C C1 0.7916(4) 0.10320(17) 0.61740(13) 0.0374(7) Uani d . 1 1 . .
H H1A 0.7709 0.1030 0.6594 0.056 Uiso calc R 1 1 . .
H H1B 0.8606 0.1420 0.6072 0.056 Uiso calc R 1 1 . .
H H1C 0.8503 0.0621 0.6064 0.056 Uiso calc R 1 1 . .
C C2 0.6185(4) 0.10723(16) 0.58376(13) 0.0333(7) Uani d . 1 1 . .
C C3 0.5059(4) 0.16923(14) 0.59888(13) 0.0292(6) Uani d . 1 1 . .
H H3 0.3995 0.1645 0.5763 0.035 Uiso calc R 1 1 . .
C C4 0.5853(3) 0.23727(15) 0.58138(13) 0.0293(6) Uani d . 1 1 . .
C C5 0.5405(4) 0.26704(17) 0.52790(13) 0.0362(7) Uani d . 1 1 . .
H H5 0.4651 0.2445 0.5028 0.043 Uiso calc R 1 1 . .
C C6 0.6055(4) 0.32954(17) 0.51103(14) 0.0415(8) Uani d . 1 1 . .
H H6 0.5765 0.3484 0.4745 0.050 Uiso calc R 1 1 . .
C C7 0.7156(4) 0.36407(18) 0.54968(15) 0.0437(8) Uani d . 1 1 . .
H H7 0.7570 0.4070 0.5396 0.052 Uiso calc R 1 1 . .
C C8 0.7623(4) 0.33466(18) 0.60226(15) 0.0444(8) Uani d . 1 1 . .
H H8 0.8381 0.3572 0.6273 0.053 Uiso calc R 1 1 . .
C C9 0.6972(4) 0.27113(17) 0.61859(14) 0.0414(8) Uani d . 1 1 . .
H H9 0.7290 0.2516 0.6545 0.050 Uiso calc R 1 1 . .
C C10 0.3185(3) 0.28495(15) 0.69070(12) 0.0314(6) Uani d . 1 1 . .
C C11 0.2653(4) 0.32776(18) 0.64579(14) 0.0402(7) Uani d . 1 1 . .
H H11 0.2085 0.3099 0.6131 0.048 Uiso calc R 1 1 . .
C C12 0.2959(5) 0.39679(18) 0.64904(15) 0.0465(8) Uani d . 1 1 . .
H H12 0.2601 0.4252 0.6184 0.056 Uiso calc R 1 1 . .
C C13 0.3804(4) 0.42454(18) 0.69822(14) 0.0419(8) Uani d . 1 1 . .
C C14 0.4350(4) 0.38054(17) 0.74268(15) 0.0423(8) Uani d . 1 1 . .
H H14 0.4939 0.3980 0.7751 0.051 Uiso calc R 1 1 . .
C C15 0.4037(4) 0.31171(16) 0.73966(13) 0.0349(7) Uani d . 1 1 . .
H H15 0.4392 0.2831 0.7702 0.042 Uiso calc R 1 1 . .
C C16 0.4064(4) 0.49975(18) 0.70326(17) 0.0491(9) Uani d . 1 1 . .
H H16A 0.3241 0.5184 0.7304 0.074 Uiso calc R 1 1 . .
H H16B 0.3922 0.5204 0.6650 0.074 Uiso calc R 1 1 . .
H H16C 0.5196 0.5087 0.7177 0.074 Uiso calc R 1 1 . .
Cl Cl1 0.65350(9) 0.10276(4) 0.50665(3) 0.03580(19) Uani d . 1 1 . .
N N1 0.5083(4) 0.04372(13) 0.59707(12) 0.0407(6) Uani d . 1 1 . .
N N2 0.4620(3) 0.16217(13) 0.66251(11) 0.0334(6) Uani d . 1 1 . .
H H2A 0.547(4) 0.1794(17) 0.6841(15) 0.040 Uiso d . 1 1 . .
O O1 0.1557(3) 0.18367(12) 0.64347(10) 0.0439(6) Uani d . 1 1 . .
O O2 0.2635(3) 0.17162(12) 0.74582(9) 0.0432(6) Uani d . 1 1 . .
O O3 0.3667(3) 0.04155(12) 0.57591(12) 0.0547(7) Uani d . 1 1 . .
O O4 0.5674(3) -0.00057(13) 0.62846(12) 0.0595(7) Uani d . 1 1 . .
S S1 0.28433(9) 0.19677(4) 0.68662(3) 0.03081(19) Uani d . 1 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

C1 0.0406(16) 0.0483(18) 0.0233(14) 0.0236(14) -0.0020(12) -0.0033(14)
C2 0.0365(16) 0.0373(16) 0.0261(14) 0.0020(13) 0.0056(12) -0.0015(13)
C3 0.0296(15) 0.0309(14) 0.0270(14) -0.0002(12) 0.0055(11) -0.0002(12)
C4 0.0267(14) 0.0322(15) 0.0290(15) -0.0027(11) 0.0033(12) -0.0024(12)
C5 0.0344(15) 0.0448(17) 0.0295(15) -0.0005(14) -0.0042(12) 0.0001(13)
C6 0.056(2) 0.0446(19) 0.0242(16) 0.0022(15) 0.0026(14) 0.0134(14)
C7 0.0534(19) 0.0383(18) 0.0393(19) -0.0083(15) 0.0079(15) 0.0100(15)
C8 0.0513(19) 0.0471(19) 0.0349(18) -0.0214(16) 0.0037(15) 0.0031(15)
C9 0.0496(18) 0.0467(19) 0.0279(15) -0.0154(15) -0.0060(14) 0.0084(14)
C10 0.0265(14) 0.0402(17) 0.0275(15) 0.0008(12) 0.0057(11) 0.0011(12)
C11 0.0452(17) 0.0461(19) 0.0293(16) 0.0124(14) -0.0042(14) 0.0062(14)
C12 0.059(2) 0.0433(19) 0.0368(18) 0.0120(16) -0.0016(16) 0.0137(16)
C13 0.0474(19) 0.0432(18) 0.0350(17) -0.0008(14) 0.0099(14) 0.0068(15)
C14 0.0435(18) 0.0471(19) 0.0363(17) -0.0077(14) -0.0042(14) -0.0025(15)
C15 0.0373(15) 0.0392(16) 0.0281(15) -0.0009(13) -0.0026(12) 0.0021(13)
C16 0.0394(17) 0.050(2) 0.058(2) -0.0181(15) 0.0056(17) 0.0087(18)
Cl1 0.0403(4) 0.0396(4) 0.0275(4) 0.0017(3) 0.0128(3) -0.0108(3)
N1 0.0507(17) 0.0366(15) 0.0347(15) -0.0014(13) 0.0048(13) -0.0007(12)
N2 0.0326(13) 0.0325(14) 0.0351(15) 0.0000(10) 0.0028(11) -0.0005(11)
O1 0.0323(10) 0.0607(15) 0.0387(12) -0.0070(10) -0.0006(10) -0.0059(11)
O2 0.0565(14) 0.0451(13) 0.0281(11) -0.0041(10) 0.0182(11) 0.0042(10)
O3 0.0564(15) 0.0482(14) 0.0597(17) -0.0259(12) 0.0007(13) -0.0081(12)
O4 0.0644(16) 0.0474(15) 0.0667(18) 0.0107(12) 0.0152(14) 0.0303(14)
S1 0.0299(3) 0.0364(4) 0.0261(4) -0.0028(3) 0.0059(3) 0.0004(3)


_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag

C1 C2 . 1.555(4) ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C2 C3 . 1.539(4) ?
C2 N1 . 1.544(4) no
C2 Cl1 . 1.761(3) no
C3 N2 . 1.481(4) no
C3 C4 . 1.524(4) ?
C3 H3 . 0.9800 ?
C4 C9 . 1.382(4) ?
C4 C5 . 1.384(4) ?
C5 C6 . 1.380(4) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.400(5) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.367(5) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.395(4) ?
C8 H8 . 0.9300 ?
C9 H9 . 0.9300 ?
C10 C11 . 1.379(4) ?
C10 C15 . 1.392(4) ?
C10 S1 . 1.752(3) ?
C11 C12 . 1.377(5) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.400(5) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.390(5) ?
C13 C16 . 1.493(5) ?
C14 C15 . 1.373(4) ?
C14 H14 . 0.9300 ?
C15 H15 . 0.9300 ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 0.9600 ?
N1 O3 . 1.207(3) ?
N1 O4 . 1.212(3) ?
N2 S1 . 1.639(3) no
N2 H2A . 0.89(3) ?
O1 S1 . 1.423(2) ?
O2 S1 . 1.432(2) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag

C2 C1 H1A . . 109.5 ?
C2 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
C2 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
C3 C2 N1 . . 105.9(2) ?
C3 C2 C1 . . 115.5(2) ?
N1 C2 C1 . . 110.5(2) ?
C3 C2 Cl1 . . 110.3(2) ?
N1 C2 Cl1 . . 103.78(19) ?
C1 C2 Cl1 . . 110.1(2) ?
N2 C3 C4 . . 115.3(2) ?
N2 C3 C2 . . 105.9(2) no
C4 C3 C2 . . 113.6(2) ?
N2 C3 H3 . . 107.2 ?
C4 C3 H3 . . 107.2 ?
C2 C3 H3 . . 107.2 ?
C9 C4 C5 . . 119.1(3) ?
C9 C4 C3 . . 121.5(3) ?
C5 C4 C3 . . 119.4(3) ?
C6 C5 C4 . . 121.4(3) ?
C6 C5 H5 . . 119.3 ?
C4 C5 H5 . . 119.3 ?
C5 C6 C7 . . 119.0(3) ?
C5 C6 H6 . . 120.5 ?
C7 C6 H6 . . 120.5 ?
C8 C7 C6 . . 120.0(3) ?
C8 C7 H7 . . 120.0 ?
C6 C7 H7 . . 120.0 ?
C7 C8 C9 . . 120.5(3) ?
C7 C8 H8 . . 119.8 ?
C9 C8 H8 . . 119.8 ?
C4 C9 C8 . . 120.0(3) ?
C4 C9 H9 . . 120.0 ?
C8 C9 H9 . . 120.0 ?
C11 C10 C15 . . 119.8(3) ?
C11 C10 S1 . . 121.1(2) ?
C15 C10 S1 . . 119.1(2) ?
C12 C11 C10 . . 120.5(3) ?
C12 C11 H11 . . 119.8 ?
C10 C11 H11 . . 119.8 ?
C11 C12 C13 . . 120.4(3) ?
C11 C12 H12 . . 119.8 ?
C13 C12 H12 . . 119.8 ?
C14 C13 C12 . . 118.3(3) ?
C14 C13 C16 . . 121.1(3) ?
C12 C13 C16 . . 120.6(3) ?
C15 C14 C13 . . 121.3(3) ?
C15 C14 H14 . . 119.3 ?
C13 C14 H14 . . 119.3 ?
C14 C15 C10 . . 119.7(3) ?
C14 C15 H15 . . 120.2 ?
C10 C15 H15 . . 120.2 ?
C13 C16 H16A . . 109.5 ?
C13 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C13 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
O3 N1 O4 . . 123.8(3) no
O3 N1 C2 . . 117.7(3) ?
O4 N1 C2 . . 118.6(3) ?
C3 N2 S1 . . 118.6(2) ?
C3 N2 H2A . . 109(2) ?
S1 N2 H2A . . 107(2) ?
O1 S1 O2 . . 119.59(14) no
O1 S1 N2 . . 107.37(14) ?
O2 S1 N2 . . 105.25(14) ?
O1 S1 C10 . . 108.79(14) ?
O2 S1 C10 . . 107.97(14) no
N2 S1 C10 . . 107.24(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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag

N1 C2 C3 N2 . . . . 59.6(3) ?
C1 C2 C3 N2 . . . . -63.2(3) ?
Cl1 C2 C3 N2 . . . . 171.28(19) ?
N1 C2 C3 C4 . . . . -172.9(2) ?
C1 C2 C3 C4 . . . . 64.4(3) ?
Cl1 C2 C3 C4 . . . . -61.2(3) ?
N2 C3 C4 C9 . . . . 36.7(4) ?
C2 C3 C4 C9 . . . . -85.7(3) ?
N2 C3 C4 C5 . . . . -141.2(3) ?
C2 C3 C4 C5 . . . . 96.3(3) ?
C9 C4 C5 C6 . . . . 0.2(5) ?
C3 C4 C5 C6 . . . . 178.1(3) ?
C4 C5 C6 C7 . . . . -1.6(5) ?
C5 C6 C7 C8 . . . . 2.4(5) ?
C6 C7 C8 C9 . . . . -1.8(5) ?
C5 C4 C9 C8 . . . . 0.5(5) ?
C3 C4 C9 C8 . . . . -177.4(3) ?
C7 C8 C9 C4 . . . . 0.4(5) ?
C15 C10 C11 C12 . . . . 0.0(5) ?
S1 C10 C11 C12 . . . . -178.8(3) ?
C10 C11 C12 C13 . . . . -0.4(5) ?
C11 C12 C13 C14 . . . . 1.2(5) ?
C11 C12 C13 C16 . . . . -177.1(3) ?
C12 C13 C14 C15 . . . . -1.7(5) ?
C16 C13 C14 C15 . . . . 176.7(3) ?
C13 C14 C15 C10 . . . . 1.2(5) ?
C11 C10 C15 C14 . . . . -0.4(4) ?
S1 C10 C15 C14 . . . . 178.4(2) ?
C3 C2 N1 O3 . . . . 50.9(3) ?
C1 C2 N1 O3 . . . . 176.7(3) ?
Cl1 C2 N1 O3 . . . . -65.3(3) ?
C3 C2 N1 O4 . . . . -128.4(3) ?
C1 C2 N1 O4 . . . . -2.5(4) ?
Cl1 C2 N1 O4 . . . . 115.5(3) ?
C4 C3 N2 S1 . . . . 80.2(3) ?
C2 C3 N2 S1 . . . . -153.3(2) ?
C3 N2 S1 O1 . . . . 41.9(3) ?
C3 N2 S1 O2 . . . . 170.3(2) ?
C3 N2 S1 C10 . . . . -74.9(2) ?
C11 C10 S1 O1 . . . . -18.0(3) ?
C15 C10 S1 O1 . . . . 163.2(2) ?
C11 C10 S1 O2 . . . . -149.2(2) ?
C15 C10 S1 O2 . . . . 32.0(3) ?
C11 C10 S1 N2 . . . . 97.8(3) ?
C15 C10 S1 N2 . . . . -80.9(2) ?

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 H3 O1 . 0.98 2.46 2.933(4) 109 yes
C3 H3 O3 . 0.98 2.42 2.779(4) 101 yes
C1 H1A O2 6_657 0.96 2.52 3.369(4) 147 yes
C1 H1B O1 1_655 0.96 2.58 3.310(4) 133 yes
N2 H2A O2 6_657 0.89(2) 2.32(3) 3.141(3) 153 yes