data_2012023
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2001
_journal_volume  57
_journal_page_first  740
_journal_page_last  741
_publ_section_title
;
(Z)-7-Chloro-3-[(3-chlorophenyl)methylidene]-4-p-tosyl-3,4-dihydro-2H-1,4-
benzoxazine
;
loop_
_publ_author_name
  'Chaudhuri, Gopeswar'
  'Helliwell, Madeleine'
  'Kundu, Nitya G.'
_chemical_formula_moiety  'C22 H17 Cl2 N O3 S'
_chemical_formula_sum  'C22 H17 Cl2 N O3 S'
_chemical_formula_weight  446.33
_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  10.899(5)
_cell_length_b  12.211(4)
_cell_length_c  7.775(3)
_cell_angle_alpha  102.23(2)
_cell_angle_beta  92.21(3)
_cell_angle_gamma  96.64(3)
_cell_volume  1002.4(6)
_cell_formula_units_Z  2
_cell_measurement_temperature  296.2
_exptl_crystal_density_diffrn  1.479
_diffrn_ambient_temperature  296.2
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
  Cl1  .60753(9)  .47686(8)  .28836(13)  .0776(3) Uani d . 1 . . Cl
  Cl2  .16901(8) 1.25696(7)  -.16951(11)  .0661(2) Uani d . 1 . . Cl
  S1  .26517(6)  .92383(5)  .51062(8)  .03593(16) Uani d . 1 . . S
  O1  .22911(16)  .63114(14)  .1063(2)  .0470(5) Uani d . 1 . . O
  O2  .37269(16)  .94479(15)  .6270(2)  .0478(5) Uani d . 1 . . O
  O3  .20554(17) 1.01453(14)  .4742(2)  .0478(5) Uani d . 1 . . O
  N1  .30633(17)  .85392(16)  .3145(2)  .0338(4) Uani d . 1 . . N
  C1  .3788(2)  .7624(2)  .3124(3)  .0346(5) Uani d . 1 . . C
  C2  .4938(2)  .7797(2)  .4019(3)  .0416(6) Uani d . 1 . . C
  H2  .5246  .8515  .4662  .050 Uiso calc R 1 . . H
  C3  .5632(3)  .6920(2)  .3971(4)  .0495(7) Uani d . 1 . . C
  H3  .6390  .7035  .4617  .059 Uiso calc R 1 . . H
  C4  .5198(3)  .5879(2)  .2963(4)  .0484(7) Uani d . 1 . . C
  C5  .4092(3)  .5688(2)  .1995(4)  .0468(6) Uani d . 1 . . C
  H5  .3824  .4980  .1285  .056 Uiso calc R 1 . . H
  C6  .3373(2)  .6562(2)  .2081(3)  .0381(6) Uani d . 1 . . C
  C7  .1435(2)  .7123(2)  .1472(3)  .0404(6) Uani d . 1 . . C
  H7A  .1034  .7033  .2535  .049 Uiso calc R 1 . . H
  H7B  .0801  .6998  .0516  .049 Uiso calc R 1 . . H
  C8  .2104(2)  .8296(2)  .1736(3)  .0356(5) Uani d . 1 . . C
  C9  .1884(2)  .8997(2)  .0715(3)  .0386(6) Uani d . 1 . . C
  H9  .1207  .8739  -.0093  .046 Uiso calc R 1 . . H
  C10  .2513(2) 1.0107(2)  .0623(3)  .0372(5) Uani d . 1 . . C
  C11  .1902(2) 1.0758(2)  -.0310(3)  .0403(6) Uani d . 1 . . C
  H11  .1099 1.0502  -.0793  .048 Uiso calc R 1 . . H
  C12  .2479(2) 1.1778(2)  -.0521(3)  .0422(6) Uani d . 1 . . C
  C13  .3669(3) 1.2175(2)  .0145(4)  .0522(7) Uani d . 1 . . C
  H13  .4053 1.2863  -.0018  .063 Uiso calc R 1 . . H
  C14  .4282(3) 1.1528(3)  .1060(4)  .0563(8) Uani d . 1 . . C
  H14  .5091 1.1783  .1517  .068 Uiso calc R 1 . . H
  C15  .3716(2) 1.0514(2)  .1309(4)  .0481(7) Uani d . 1 . . C
  H15  .4143 1.0094  .1942  .058 Uiso calc R 1 . . H
  C16  .1555(2)  .8288(2)  .5823(3)  .0358(5) Uani d . 1 . . C
  C17  .0320(2)  .8437(2)  .5768(3)  .0453(6) Uani d . 1 . . C
  H17  .0071  .9064  .5418  .054 Uiso calc R 1 . . H
  C18  -.0539(3)  .7655(3)  .6232(4)  .0526(7) Uani d . 1 . . C
  H18  -.1368  .7768  .6219  .063 Uiso calc R 1 . . H
  C19  -.0195(3)  .6704(2)  .6717(4)  .0522(7) Uani d . 1 . . C
  C20  .1046(3)  .6577(2)  .6780(4)  .0517(7) Uani d . 1 . . C
  H20  .1293  .5947  .7125  .062 Uiso calc R 1 . . H
  C21  .1931(2)  .7359(2)  .6345(3)  .0431(6) Uani d . 1 . . C
  H21  .2765  .7263  .6403  .052 Uiso calc R 1 . . H
  C22  -.1147(4)  .5833(3)  .7161(5)  .0831(12) Uani d . 1 . . C
  H22A  -.0744  .5235  .7466  .125 Uiso calc PR  .50 . . H
  H22B  -.1721  .5531  .6160  .125 Uiso calc PR  .50 . . H
  H22C  -.1583  .6176  .8141  .125 Uiso calc PR  .50 . . H
  H22D  -.1955  .6060  .7046  .125 Uiso calc PR  .50 . . H
  H22E  -.0977  .5764  .8351  .125 Uiso calc PR  .50 . . H
  H22F  -.1116  .5119  .6370  .125 Uiso calc PR  .50 . . 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
  Cl1  .0802(6)  .0717(6)  .0954(7)  .0454(5)  .0147(5)  .0299(5)
  Cl2  .0673(5)  .0728(5)  .0754(5)  .0307(4)  .0108(4)  .0417(4)
  S1  .0397(3)  .0328(3)  .0349(3)  .0061(3)  .0009(3)  .0058(2)
  O1  .0453(11)  .0366(10)  .0537(11)  .0043(8)  -.0033(9)  -.0005(8)
  O2  .0449(10)  .0533(11)  .0392(10)  .0009(9)  -.0043(8)  .0006(8)
  O3  .0615(12)  .0342(10)  .0505(11)  .0148(9)  .0063(9)  .0107(8)
  N1  .0347(11)  .0344(10)  .0321(10)  .0043(8)  -.0003(8)  .0077(8)
  C1  .0356(13)  .0365(13)  .0342(13)  .0063(10)  .0082(10)  .0113(10)
  C2  .0358(14)  .0444(14)  .0444(14)  .0051(11)  .0026(11)  .0092(11)
  C3  .0390(14)  .0642(19)  .0507(16)  .0160(13)  .0040(12)  .0192(14)
  C4  .0517(17)  .0487(16)  .0538(17)  .0222(13)  .0170(14)  .0203(13)
  C5  .0529(17)  .0361(14)  .0538(16)  .0093(12)  .0123(14)  .0115(12)
  C6  .0358(13)  .0389(14)  .0399(14)  .0029(11)  .0073(11)  .0093(11)
  C7  .0353(13)  .0433(14)  .0409(14)  .0025(11)  .0000(11)  .0069(11)
  C8  .0337(13)  .0378(13)  .0339(13)  .0062(10)  .0005(10)  .0041(10)
  C9  .0370(13)  .0442(14)  .0333(13)  .0071(11)  -.0029(10)  .0057(11)
  C10  .0402(14)  .0404(13)  .0320(12)  .0081(11)  .0001(11)  .0087(10)
  C11  .0369(14)  .0508(16)  .0359(13)  .0120(12)  .0028(11)  .0116(11)
  C12  .0494(16)  .0447(15)  .0378(14)  .0181(12)  .0062(12)  .0140(11)
  C13  .0614(19)  .0454(16)  .0508(17)  .0009(14)  .0037(14)  .0161(13)
  C14  .0495(17)  .0598(19)  .0596(18)  -.0067(14)  -.0101(14)  .0231(15)
  C15  .0453(16)  .0561(17)  .0463(16)  .0050(13)  -.0074(12)  .0214(13)
  C16  .0416(14)  .0355(13)  .0298(12)  .0062(10)  .0020(10)  .0056(10)
  C17  .0424(15)  .0506(16)  .0455(15)  .0108(13)  .0011(12)  .0140(12)
  C18  .0390(15)  .0651(19)  .0503(17)  .0011(14)  .0026(13)  .0080(14)
  C19  .0633(19)  .0462(16)  .0400(15)  -.0085(14)  .0113(14)  .0007(12)
  C20  .074(2)  .0388(15)  .0466(16)  .0104(14)  .0147(15)  .0144(12)
  C21  .0475(15)  .0439(15)  .0417(14)  .0149(12)  .0070(12)  .0120(12)
  C22  .092(3)  .072(2)  .073(2)  -.025(2)  .027(2)  .0044(19)
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
  Cl1 C4 . 1.740(3) ?
  Cl2 C12 . 1.735(3) ?
  S1 O2 . 1.4169(19) ?
  S1 O3 . 1.4191(18) ?
  S1 N1 . 1.687(2) ?
  S1 C16 . 1.758(3) ?
  O1 C6 . 1.361(3) ?
  O1 C7 . 1.434(3) ?
  N1 C1 . 1.439(3) ?
  N1 C8 . 1.443(3) ?
  C1 C2 . 1.382(3) ?
  C1 C6 . 1.391(3) ?
  C2 C3 . 1.377(3) ?
  C2 H2 .  .9300 ?
  C3 C4 . 1.365(4) ?
  C3 H3 .  .9300 ?
  C4 C5 . 1.365(4) ?
  C5 C6 . 1.387(3) ?
  C5 H5 .  .9300 ?
  C7 C8 . 1.499(3) ?
  C7 H7A .  .9700 ?
  C7 H7B .  .9700 ?
  C8 C9 . 1.320(3) ?
  C9 C10 . 1.464(3) ?
  C9 H9 .  .9300 ?
  C10 C11 . 1.389(3) ?
  C10 C15 . 1.390(4) ?
  C11 C12 . 1.374(4) ?
  C11 H11 .  .9300 ?
  C12 C13 . 1.372(4) ?
  C13 C14 . 1.378(4) ?
  C13 H13 .  .9300 ?
  C14 C15 . 1.373(4) ?
  C14 H14 .  .9300 ?
  C15 H15 .  .9300 ?
  C16 C17 . 1.379(3) ?
  C16 C21 . 1.382(3) ?
  C17 C18 . 1.373(4) ?
  C17 H17 .  .9300 ?
  C18 C19 . 1.380(4) ?
  C18 H18 .  .9300 ?
  C19 C20 . 1.380(4) ?
  C19 C22 . 1.502(4) ?
  C20 C21 . 1.380(4) ?
  C20 H20 .  .9300 ?
  C21 H21 .  .9300 ?
  C22 H22A .  .9600 ?
  C22 H22B .  .9600 ?
  C22 H22C .  .9600 ?
  C22 H22D .  .9600 ?
  C22 H22E .  .9600 ?
  C22 H22F .  .9600 ?