#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2200777.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_2200777
loop_
_publ_author_name
'Michaux, Catherine'
'Charlier, Caroline'
'Jul\'emont, Fabien'
'Norberg, Bernadette'
'Dogn\'e, Jean-Michel'
'Durant, Fran\,cois'
_publ_section_title
;
 FJ6,
 <i>N</i>-methyl-<i>N</i>-(4-nitro-2-phenoxyphenyl)methanesulfonamide
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1012
_journal_page_last               o1013
_journal_volume                  57
_journal_year                    2001
_chemical_formula_iupac          'C14 H14 N2 O5 S'
_chemical_formula_moiety         'C14 H14 N2 O5 S'
_chemical_formula_sum            'C14 H14 N2 O5 S'
_chemical_formula_weight         322.33
_chemical_name_systematic
;
N-methyl-N-(4-nitro-2-phenoxyphenyl)methanesulfonamide
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 109.460(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.5220(10)
_cell_length_b                   10.4390(10)
_cell_length_c                   10.5230(10)
_cell_measurement_reflns_used    24
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      40
_cell_measurement_theta_min      32
_cell_volume                     1504.1(2)
_computing_cell_refinement       'CAD-4 EXPRESS'
_computing_data_collection       'CAD-4 EXPRESS (Enraf-Nonius, 1992)'
_computing_data_reduction        'PLATON (Spek, 2001)'
_computing_molecular_graphics    PLATON
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  Nonius
_diffrn_measurement_method       \w/\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'long fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  .0335
_diffrn_reflns_av_sigmaI/netI    .0330
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5119
_diffrn_reflns_theta_full        71.87
_diffrn_reflns_theta_max         71.87
_diffrn_reflns_theta_min         3.23
_diffrn_standards_decay_%        5
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    2.155
_exptl_absorpt_correction_T_max  .743
_exptl_absorpt_correction_T_min  .411
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   '(de Meulenaer & Tompa, 1965)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       polyhedral
_exptl_crystal_F_000             672
_exptl_crystal_size_max          .46
_exptl_crystal_size_mid          .36
_exptl_crystal_size_min          .15
_refine_diff_density_max         .228
_refine_diff_density_min         -.311
_refine_ls_extinction_coef       .0139(8)
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2951
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          .0440
_refine_ls_R_factor_gt           .0413
_refine_ls_shift/su_max          .005
_refine_ls_shift/su_mean         .001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.061P)^2^+0.373P] where P= (Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .1176
_reflns_number_gt                2747
_reflns_number_total             2951
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    wn6057.cif
_[local]_cod_data_source_block   I
_[local]_cod_cif_authors_sg_H-M  'P 21/c'
_cod_database_code               2200777
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_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_type_symbol
S19 .09820(3) .39270(5) .16659(4) .05765(19) Uani d . 1 S
O21 .04416(12) .27815(16) .12467(17) .0850(5) Uani d . 1 O
O7 .22028(10) .50640(18) .50900(13) .0797(5) Uani d . 1 O
O16 .51319(13) .77639(18) .56081(16) .0869(5) Uani d . 1 O
O15 .55160(14) .7375(2) .38477(18) .0973(6) Uani d . 1 O
O20 .12730(11) .4642(2) .07183(15) .0857(5) Uani d . 1 O
N17 .19856(10) .35423(14) .28886(15) .0552(4) Uani d . 1 N
N14 .50130(11) .71966(16) .45550(16) .0618(4) Uani d . 1 N
C10 .42369(11) .62339(16) .41260(16) .0491(4) Uani d . 1 C
C12$ .33644(13) .46585(18) .25715(17) .0542(4) Uani d . 1 C
C8 .28922(11) .52039(17) .44807(16) .0504(4) Uani d . 1 C
C13 .27459(11) .44752(16) .33146(15) .0469(3) Uani d . 1 C
C9 .36518(12) .60666(17) .49095(16) .0521(4) Uani d . 1 C
H9 .3766 .6523 .5706 .063 Uiso calc R 1 H
C11 .41069(13) .55540(19) .29531(17) .0563(4) Uani d . 1 C
H11 .4507 .5695 .2436 .068 Uiso calc R 1 H
C3 .31187(16) .4931(2) .7455(2) .0681(5) Uani d . 1 C
H3 .3537 .4333 .7283 .082 Uiso calc R 1 H
C4 .23891(13) .54821(19) .64109(17) .0567(4) Uani d . 1 C
C22 .03142(16) .4925(3) .2367(3) .0801(6) Uani d . 1 C
H22A .0673 .5701 .2678 .120 Uiso calc R 1 H
H22B .0205 .4496 .3112 .120 Uiso calc R 1 H
H22C -.0302 .5125 .1697 .120 Uiso calc R 1 H
C1 .26067(18) .6124(2) .9017(2) .0724(6) Uani d . 1 C
H1 .2673 .6329 .9903 .087 Uiso calc R 1 H
C2 .32242(18) .5271(2) .8760(2) .0719(5) Uani d . 1 C
H2 .3724 .4913 .9471 .086 Uiso calc R 1 H
C5 .17718(15) .6381(2) .6648(2) .0714(5) Uani d . 1 C
H5 .1291 .6777 .5942 .086 Uiso calc R 1 H
C6 .18948(18) .6677(2) .7993(3) .0796(6) Uani d . 1 C
H6 .1478 .7266 .8184 .095 Uiso calc R 1 H
C18 .18954(18) .2569(2) .3867(3) .0826(7) Uani d . 1 C
H18A .2531 .2380 .4498 .124 Uiso calc R 1 H
H18B .1613 .1801 .3395 .124 Uiso calc R 1 H
H18C .1485 .2894 .4343 .124 Uiso calc R 1 H
H12 .3296 .4224 .1782 .071(6) Uiso d R 1 H
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
S19 .0491(3) .0693(3) .0530(3) -.00738(17) .01497(18) -.00689(18)
O21 .0707(9) .0824(10) .0943(11) -.0200(7) .0170(8) -.0286(8)
O7 .0535(7) .1426(14) .0514(7) -.0261(8) .0286(6) -.0203(8)
O16 .0821(10) .1003(12) .0759(9) -.0309(9) .0229(8) -.0212(8)
O15 .0878(11) .1210(14) .0976(11) -.0441(10) .0503(9) -.0093(10)
O20 .0648(8) .1299(14) .0572(8) -.0108(9) .0132(6) .0203(8)
N17 .0506(7) .0555(8) .0597(8) -.0035(6) .0187(6) .0047(6)
N14 .0523(8) .0684(9) .0625(9) -.0063(7) .0164(7) .0074(7)
C10 .0408(7) .0566(9) .0484(8) .0006(6) .0131(6) .0084(6)
C12$ .0517(9) .0661(10) .0493(8) .0004(7) .0227(7) -.0039(7)
C8 .0428(8) .0678(10) .0434(8) .0027(7) .0183(6) .0053(7)
C13 .0421(7) .0529(8) .0461(8) .0039(6) .0150(6) .0061(6)
C9 .0467(8) .0653(10) .0445(8) .0025(7) .0155(6) -.0002(7)
C11 .0491(8) .0751(11) .0511(8) -.0015(8) .0253(7) .0046(8)
C3 .0701(12) .0756(12) .0620(11) .0078(9) .0268(9) -.0037(9)
C4 .0529(9) .0754(11) .0493(8) -.0099(8) .0271(7) -.0036(8)
C22 .0548(11) .0934(15) .0839(14) .0104(10) .0122(10) -.0186(12)
C1 .0928(15) .0701(12) .0627(11) -.0159(11) .0371(11) -.0128(9)
C2 .0870(14) .0734(12) .0548(10) -.0037(10) .0229(10) .0033(9)
C5 .0615(11) .0752(12) .0790(13) .0038(9) .0254(10) .0055(10)
C6 .0859(15) .0712(13) .0953(16) .0028(11) .0484(13) -.0201(12)
C18 .0760(13) .0714(13) .0967(16) -.0074(10) .0239(12) .0275(11)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0181 .0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0311 .0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0492 .0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S .3331 .5567 '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
O21 S19 O20 119.28(11)
O21 S19 N17 107.01(9)
O20 S19 N17 106.58(8)
O21 S19 C22 107.87(12)
O20 S19 C22 108.71(13)
N17 S19 C22 106.74(10)
C8 O7 C4 120.37(13)
C13 N17 C18 119.16(15)
C13 N17 S19 118.12(11)
C18 N17 S19 116.83(13)
O16 N14 O15 123.36(17)
O16 N14 C10 118.41(15)
O15 N14 C10 118.22(16)
C9 C10 C11 122.79(16)
C9 C10 N14 117.85(15)
C11 C10 N14 119.35(15)
C11 C12$ C13 121.26(16)
C11 C12$ H12 115.7
C13 C12$ H12 123.0
O7 C8 C9 123.26(16)
O7 C8 C13 115.68(15)
C9 C8 C13 120.91(14)
C12$ C13 C8 118.82(15)
C12$ C13 N17 119.71(15)
C8 C13 N17 121.46(14)
C10 C9 C8 118.21(15)
C10 C9 H9 120.9
C8 C9 H9 120.9
C10 C11 C12$ 117.94(15)
C10 C11 H11 121.0
C12$ C11 H11 121.0
C4 C3 C2 119.3(2)
C4 C3 H3 120.3
C2 C3 H3 120.3
C3 C4 C5 121.05(18)
C3 C4 O7 120.55(18)
C5 C4 O7 118.18(18)
S19 C22 H22A 109.5
S19 C22 H22B 109.5
H22A C22 H22B 109.5
S19 C22 H22C 109.5
H22A C22 H22C 109.5
H22B C22 H22C 109.5
C6 C1 C2 120.3(2)
C6 C1 H1 119.8
C2 C1 H1 119.8
C1 C2 C3 120.5(2)
C1 C2 H2 119.7
C3 C2 H2 119.7
C4 C5 C6 117.5(2)
C4 C5 H5 121.2
C6 C5 H5 121.2
C1 C6 C5 121.2(2)
C1 C6 H6 119.4
C5 C6 H6 119.4
N17 C18 H18A 109.5
N17 C18 H18B 109.5
H18A C18 H18B 109.5
N17 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S19 O21 1.4177(15)
S19 O20 1.4183(16)
S19 N17 1.6405(15)
S19 C22 1.745(2)
O7 C8 1.3647(19)
O7 C4 1.395(2)
O16 N14 1.217(2)
O15 N14 1.218(2)
N17 C13 1.428(2)
N17 C18 1.484(2)
N14 C10 1.465(2)
C10 C9 1.378(2)
C10 C11 1.381(3)
C12$ C11 1.382(3)
C12$ C13 1.387(2)
C12$ H12 .9229
C8 C9 1.378(2)
C8 C13 1.399(2)
C9 H9 .9300
C11 H11 .9300
C3 C4 1.373(3)
C3 C2 1.376(3)
C3 H3 .9300
C4 C5 1.377(3)
C22 H22A .9600
C22 H22B .9600
C22 H22C .9600
C1 C6 1.349(3)
C1 C2 1.353(3)
C1 H1 .9300
C2 H2 .9300
C5 C6 1.400(3)
C5 H5 .9300
C6 H6 .9300
C18 H18A .9600
C18 H18B .9600
C18 H18C .9600
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
O21 S19 N17 C13 168.05(13)
O20 S19 N17 C13 39.39(16)
C22 S19 N17 C13 -76.65(16)
O21 S19 N17 C18 -39.15(18)
O20 S19 N17 C18 -167.82(17)
C22 S19 N17 C18 76.14(18)
O16 N14 C10 C9 3.0(2)
O15 N14 C10 C9 -178.01(18)
O16 N14 C10 C11 -178.23(17)
O15 N14 C10 C11 .7(3)
C4 O7 C8 C9 -20.3(3)
C4 O7 C8 C13 164.13(17)
C11 C12$ C13 C8 -.9(3)
C11 C12$ C13 N17 179.91(16)
O7 C8 C13 C12$ 173.96(16)
C9 C8 C13 C12$ -1.7(2)
O7 C8 C13 N17 -6.9(2)
C9 C8 C13 N17 177.49(15)
C18 N17 C13 C12$ 128.11(19)
S19 N17 C13 C12$ -79.74(18)
C18 N17 C13 C8 -51.1(2)
S19 N17 C13 C8 101.08(16)
C11 C10 C9 C8 -1.6(3)
N14 C10 C9 C8 177.13(15)
O7 C8 C9 C10 -172.45(16)
C13 C8 C9 C10 2.9(2)
C9 C10 C11 C12$ -.9(3)
N14 C10 C11 C12$ -179.59(16)
C13 C12$ C11 C10 2.2(3)
C2 C3 C4 C5 .9(3)
C2 C3 C4 O7 -173.58(18)
C8 O7 C4 C3 -63.9(3)
C8 O7 C4 C5 121.5(2)
C6 C1 C2 C3 -1.8(3)
C4 C3 C2 C1 1.1(3)
C3 C4 C5 C6 -2.2(3)
O7 C4 C5 C6 172.44(19)
C2 C1 C6 C5 .4(4)
C4 C5 C6 C1 1.5(3)