data_2012213
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2001
_journal_volume  57
_journal_page_first  1081
_journal_page_last  1083
_publ_section_title
;
N-[5-(4-Chlorophenyl)furan-2-ylmethyl]-4-methyl-N-prop-2-
ynylbenzenesulfonamide and N-[5-(2-chlorophenyl)furan-2-ylmethyl]-4-methyl-
N-prop-2-ynylbenzenesulfonamide, two isomorphous crystal structures determined
by intermolecular C-H...O, C-H...\p and C-H...Cl interactions.
;
loop_
_publ_author_name
  'Bats, Jan W.'
  'Frost, Tanja M.'
  'Hashmi, A. Stephen K.'
_chemical_formula_moiety  'C21 H18 Cl N O3 S'
_chemical_formula_sum  'C21 H18 Cl N O3 S'
_chemical_formula_weight  399.87
_symmetry_cell_setting  triclinic
_symmetry_space_group_name_H-M  'P -1'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, -y, -z'
_cell_length_a  7.6526(13)
_cell_length_b  9.679(2)
_cell_length_c  13.6308(19)
_cell_angle_alpha  79.910(13)
_cell_angle_beta  75.152(13)
_cell_angle_gamma  74.435(12)
_cell_volume  934.0(3)
_cell_formula_units_Z  2
_cell_measurement_temperature  140(2)
_exptl_crystal_density_diffrn  1.422
_diffrn_ambient_temperature  140(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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
  Cl  .65820(6)  .99972(4)  .11706(3)  .03172(10) Uani d . 1 . . Cl
  S  .37642(4)  .55893(4)  .72833(3)  .02020(9) Uani d . 1 . . S
  O1  .54390(13)  .81985(10)  .44958(7)  .0193(2) Uani d . 1 . . O
  O2  .48538(14)  .63515(13)  .76035(8)  .0296(2) Uani d . 1 . . O
  O3  .44409(14)  .40722(11)  .71881(8)  .0275(2) Uani d . 1 . . O
  N  .35159(15)  .63846(12)  .61347(9)  .0189(2) Uani d . 1 . . N
  C1  .90423(19)  .79566(16)  .34722(11)  .0232(3) Uani d . 1 . . C
  H1  .8716  .7645  .4181  .028 Uiso calc R 1 . . H
  C2 1.0903(2)  .76800(18)  .29754(12)  .0285(3) Uani d . 1 . . C
  H2 1.1829  .7180  .3344  .034 Uiso calc R 1 . . H
  C3 1.1414(2)  .81313(17)  .19423(12)  .0283(3) Uani d . 1 . . C
  H3 1.2690  .7959  .1604  .034 Uiso calc R 1 . . H
  C4 1.0056(2)  .88333(15)  .14089(11)  .0259(3) Uani d . 1 . . C
  H4 1.0396  .9131  .0698  .031 Uiso calc R 1 . . H
  C5  .81893(19)  .91053(14)  .19106(11)  .0205(3) Uani d . 1 . . C
  C6  .76272(18)  .86853(14)  .29554(10)  .0181(3) Uani d . 1 . . C
  C7  .56929(18)  .89571(14)  .35321(10)  .0178(3) Uani d . 1 . . C
  C8  .4037(2)  .98215(16)  .33891(12)  .0256(3) Uani d . 1 . . C
  H8  .3819 1.0459  .2795  .031 Uiso calc R 1 . . H
  C9  .2688(2)  .95870(17)  .43025(12)  .0275(3) Uani d . 1 . . C
  H9  .1399 1.0041  .4433  .033 Uiso calc R 1 . . H
  C10  .35837(18)  .86026(15)  .49440(11)  .0206(3) Uani d . 1 . . C
  C11  .29922(19)  .79840(15)  .60215(11)  .0218(3) Uani d . 1 . . C
  H11A  .3580  .8340  .6464  .026 Uiso calc R 1 . . H
  H11B  .1627  .8316  .6250  .026 Uiso calc R 1 . . H
  C12  .26103(19)  .57047(15)  .55732(11)  .0208(3) Uani d . 1 . . C
  H12A  .3000  .5996  .4832  .025 Uiso calc R 1 . . H
  H12B  .3044  .4643  .5695  .025 Uiso calc R 1 . . H
  C13  .0566(2)  .60995(16)  .58748(11)  .0231(3) Uani d . 1 . . C
  C14  -.1072(2)  .64134(18)  .61597(13)  .0307(3) Uani d . 1 . . C
  H14  -.2386  .6665  .6388  .037 Uiso calc R 1 . . H
  C15  .15477(18)  .58783(14)  .81087(10)  .0181(3) Uani d . 1 . . C
  C16  .05678(19)  .48039(15)  .83493(11)  .0224(3) Uani d . 1 . . C
  H16  .1112  .3891  .8103  .027 Uiso calc R 1 . . H
  C17  -.1221(2)  .50822(16)  .89562(11)  .0243(3) Uani d . 1 . . C
  H17  -.1887  .4343  .9132  .029 Uiso calc R 1 . . H
  C18  -.20563(19)  .64170(15)  .93115(10)  .0209(3) Uani d . 1 . . C
  C19  -.1045(2)  .74817(16)  .90564(12)  .0266(3) Uani d . 1 . . C
  H19  -.1598  .8401  .9291  .032 Uiso calc R 1 . . H
  C20  .0753(2)  .72198(16)  .84652(11)  .0252(3) Uani d . 1 . . C
  H20  .1436  .7948  .8305  .030 Uiso calc R 1 . . H
  C21  -.4010(2)  .67046(17)  .99532(12)  .0284(3) Uani d . 1 . . C
  H21A  -.4896  .6868  .9514  .043 Uiso calc R 1 . . H
  H21B  -.4240  .7562 1.0301  .043 Uiso calc R 1 . . H
  H21C  -.4164  .5871 1.0463  .043 Uiso calc 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
  Cl  .0343(2)  .0335(2)  .01961(17)  .00061(15)  -.00544(14)  .00306(14)
  S  .01403(15)  .02546(17)  .01882(16)  -.00380(12)  -.00073(12)  -.00216(12)
  O1  .0169(4)  .0206(5)  .0171(4)  -.0041(3)  .0008(3)  -.0003(4)
  O2  .0189(5)  .0470(7)  .0268(6)  -.0134(5)  -.0040(4)  -.0067(5)
  O3  .0220(5)  .0246(5)  .0281(6)  .0024(4)  -.0017(4)  -.0008(4)
  N  .0173(5)  .0203(5)  .0176(5)  -.0057(4)  .0006(4)  -.0027(4)
  C1  .0197(6)  .0288(7)  .0194(6)  -.0052(5)  -.0020(5)  -.0023(5)
  C2  .0192(7)  .0353(8)  .0301(8)  -.0040(6)  -.0051(6)  -.0052(6)
  C3  .0199(7)  .0298(8)  .0319(8)  -.0083(6)  .0056(6)  -.0078(6)
  C4  .0296(7)  .0219(7)  .0214(7)  -.0090(6)  .0056(6)  -.0013(5)
  C5  .0238(6)  .0164(6)  .0192(6)  -.0045(5)  -.0020(5)  -.0011(5)
  C6  .0190(6)  .0162(6)  .0181(6)  -.0055(5)  -.0004(5)  -.0030(5)
  C7  .0199(6)  .0167(6)  .0159(6)  -.0061(5)  -.0014(5)  -.0009(5)
  C8  .0208(7)  .0263(7)  .0251(7)  -.0036(5)  -.0030(5)  .0034(6)
  C9  .0164(6)  .0300(7)  .0303(8)  -.0028(5)  .0002(6)  .0002(6)
  C10  .0172(6)  .0194(6)  .0229(7)  -.0064(5)  .0027(5)  -.0039(5)
  C11  .0208(6)  .0193(6)  .0219(7)  -.0062(5)  .0042(5)  -.0046(5)
  C12  .0201(6)  .0222(6)  .0195(6)  -.0051(5)  -.0017(5)  -.0048(5)
  C13  .0240(7)  .0243(7)  .0216(7)  -.0084(5)  -.0053(5)  -.0002(5)
  C14  .0225(7)  .0381(9)  .0314(8)  -.0086(6)  -.0063(6)  -.0012(7)
  C15  .0156(6)  .0220(6)  .0153(6)  -.0046(5)  -.0007(5)  -.0018(5)
  C16  .0230(7)  .0189(6)  .0227(7)  -.0058(5)  .0007(5)  -.0025(5)
  C17  .0225(7)  .0243(7)  .0256(7)  -.0111(5)  .0013(5)  -.0030(5)
  C18  .0184(6)  .0257(7)  .0165(6)  -.0054(5)  -.0005(5)  -.0012(5)
  C19  .0283(7)  .0223(7)  .0261(7)  -.0075(6)  .0051(6)  -.0082(6)
  C20  .0268(7)  .0245(7)  .0245(7)  -.0126(6)  .0042(6)  -.0074(6)
  C21  .0203(7)  .0331(8)  .0272(8)  -.0058(6)  .0032(6)  -.0047(6)
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
  Cl C5 . 1.7425(15) ?
  S O2 . 1.4351(11) ?
  S O3 . 1.4372(11) ?
  S N . 1.6528(12) ?
  S C15 . 1.7603(13) ?
  O1 C10 . 1.3723(16) ?
  O1 C7 . 1.3821(16) ?
  N C12 . 1.4807(18) ?
  N C11 . 1.4819(18) ?
  C1 C2 . 1.386(2) ?
  C1 C6 . 1.405(2) ?
  C1 H1 .  .9500 ?
  C2 C3 . 1.386(2) ?
  C2 H2 .  .9500 ?
  C3 C4 . 1.381(2) ?
  C3 H3 .  .9500 ?
  C4 C5 . 1.392(2) ?
  C4 H4 .  .9500 ?
  C5 C6 . 1.3984(19) ?
  C6 C7 . 1.4647(18) ?
  C7 C8 . 1.3581(19) ?
  C8 C9 . 1.427(2) ?
  C8 H8 .  .9500 ?
  C9 C10 . 1.344(2) ?
  C9 H9 .  .9500 ?
  C10 C11 . 1.4890(19) ?
  C11 H11A .  .9900 ?
  C11 H11B .  .9900 ?
  C12 C13 . 1.472(2) ?
  C12 H12A .  .9900 ?
  C12 H12B .  .9900 ?
  C13 C14 . 1.184(2) ?
  C14 H14 .  .9500 ?
  C15 C16 . 1.3871(19) ?
  C15 C20 . 1.3921(19) ?
  C16 C17 . 1.3893(19) ?
  C16 H16 .  .9500 ?
  C17 C18 . 1.389(2) ?
  C17 H17 .  .9500 ?
  C18 C19 . 1.395(2) ?
  C18 C21 . 1.5064(19) ?
  C19 C20 . 1.387(2) ?
  C19 H19 .  .9500 ?
  C20 H20 .  .9500 ?
  C21 H21A .  .9800 ?
  C21 H21B .  .9800 ?
  C21 H21C .  .9800 ?