#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2012023.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_2012023
loop_
_publ_author_name
'Chaudhuri, Gopeswar'
'Helliwell, Madeleine'
'Kundu, Nitya G.'
_publ_section_title
;
 (<i>Z</i>)-7-Chloro-3-[(3-chlorophenyl)methylidene]-4-<i>p</i>-tosyl-3,4-dihydro-2<i>H</i>-1,4-benzoxazine
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              740
_journal_page_last               741
_journal_volume                  57
_journal_year                    2001
_chemical_formula_moiety         'C22 H17 Cl2 N O3 S'
_chemical_formula_sum            'C22 H17 Cl2 N O3 S'
_chemical_formula_weight         446.33
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                102.23(2)
_cell_angle_beta                 92.21(3)
_cell_angle_gamma                96.64(3)
_cell_formula_units_Z            2
_cell_length_a                   10.899(5)
_cell_length_b                   12.211(4)
_cell_length_c                   7.775(3)
_cell_measurement_reflns_used    20
_cell_measurement_temperature    296.2
_cell_measurement_theta_max      8.2
_cell_measurement_theta_min      6.8
_cell_volume                     1002.4(7)
_computing_cell_refinement       'MSC/AFC Diffractometer Control Software'
_computing_data_collection
;
MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1995)
;
_computing_data_reduction
'TEXSAN (Molecular Structure Corporation, 1995)'
_computing_publication_material  TEXSAN
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1985)'
_diffrn_ambient_temperature      296.2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Rigaku AFC5R'
_diffrn_measurement_method       \w-2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rigaku rotating anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     .7107
_diffrn_reflns_av_R_equivalents  .0177
_diffrn_reflns_av_sigmaI/netI    .0437
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4862
_diffrn_reflns_theta_full        27.56
_diffrn_reflns_theta_max         27.56
_diffrn_reflns_theta_min         1.72
_diffrn_standards_decay_%        .30
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .453
_exptl_absorpt_correction_T_max  .846
_exptl_absorpt_correction_T_min  .800
_exptl_absorpt_correction_type   '\y scans (North et al., 1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             460
_exptl_crystal_size_max          .40
_exptl_crystal_size_mid          .37
_exptl_crystal_size_min          .37
_refine_diff_density_max         .330
_refine_diff_density_min         -.218
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4619
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          .0935
_refine_ls_R_factor_gt           .0491
_refine_ls_shift/su_max          .001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w=1/[\s^2^(Fo^2^)+(0.0422P)^2^+0.3626P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_ref         .1178
_reflns_number_gt                3158
_reflns_number_total             4619
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    gd1131.cif
_[local]_cod_data_source_block   III
_[local]_cod_cif_authors_sg_H-M  'P -1       '
_cod_original_cell_volume        1002.4(6)
_cod_database_code               2012023
loop_
_symmetry_equiv_pos_as_xyz
'   +x,   +y,   +z'
'   -x,   -y,   -z'
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
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_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 '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 .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S .1246 .1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl .1484 .1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-1 -2 -2
-1 3 2
-1 4 0
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O2 S1 O3 120.68(12)
O2 S1 N1 106.29(11)
O3 S1 N1 105.86(10)
O2 S1 C16 108.54(12)
O3 S1 C16 108.71(12)
N1 S1 C16 105.79(11)
C6 O1 C7 114.86(19)
C1 N1 C8 112.98(18)
C1 N1 S1 118.36(15)
C8 N1 S1 115.05(15)
C2 C1 C6 118.8(2)
C2 C1 N1 121.2(2)
C6 C1 N1 119.8(2)
C3 C2 C1 120.8(3)
C3 C2 H2 119.6
C1 C2 H2 119.6
C4 C3 C2 119.3(3)
C4 C3 H3 120.4
C2 C3 H3 120.4
C3 C4 C5 121.6(2)
C3 C4 Cl1 119.6(2)
C5 C4 Cl1 118.9(2)
C4 C5 C6 119.3(3)
C4 C5 H5 120.4
C6 C5 H5 120.4
O1 C6 C5 115.9(2)
O1 C6 C1 124.0(2)
C5 C6 C1 120.1(2)
O1 C7 C8 109.9(2)
O1 C7 H7A 109.7
C8 C7 H7A 109.7
O1 C7 H7B 109.7
C8 C7 H7B 109.7
H7A C7 H7B 108.2
C9 C8 N1 124.1(2)
C9 C8 C7 123.2(2)
N1 C8 C7 112.6(2)
C8 C9 C10 131.6(2)
C8 C9 H9 114.2
C10 C9 H9 114.2
C11 C10 C15 118.2(2)
C11 C10 C9 117.9(2)
C15 C10 C9 123.8(2)
C12 C11 C10 120.2(2)
C12 C11 H11 119.9
C10 C11 H11 119.9
C13 C12 C11 121.6(2)
C13 C12 Cl2 119.3(2)
C11 C12 Cl2 119.1(2)
C12 C13 C14 118.3(3)
C12 C13 H13 120.8
C14 C13 H13 120.8
C15 C14 C13 121.0(3)
C15 C14 H14 119.5
C13 C14 H14 119.5
C14 C15 C10 120.7(2)
C14 C15 H15 119.7
C10 C15 H15 119.7
C17 C16 C21 120.4(2)
C17 C16 S1 120.01(19)
C21 C16 S1 119.46(19)
C18 C17 C16 119.7(3)
C18 C17 H17 120.2
C16 C17 H17 120.2
C17 C18 C19 121.3(3)
C17 C18 H18 119.4
C19 C18 H18 119.4
C18 C19 C20 118.1(3)
C18 C19 C22 120.9(3)
C20 C19 C22 121.0(3)
C19 C20 C21 121.8(3)
C19 C20 H20 119.1
C21 C20 H20 119.1
C20 C21 C16 118.7(2)
C20 C21 H21 120.6
C16 C21 H21 120.6
C19 C22 H22A 109.5
C19 C22 H22B 109.5
H22A C22 H22B 109.5
C19 C22 H22C 109.5
H22A C22 H22C 109.5
H22B C22 H22C 109.5
C19 C22 H22D 109.5
H22A C22 H22D 141.1
H22B C22 H22D 56.3
H22C C22 H22D 56.3
C19 C22 H22E 109.5
H22A C22 H22E 56.3
H22B C22 H22E 141.1
H22C C22 H22E 56.3
H22D C22 H22E 109.5
C19 C22 H22F 109.5
H22A C22 H22F 56.3
H22B C22 H22F 56.3
H22C C22 H22F 141.1
H22D C22 H22F 109.5
H22E C22 H22F 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
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
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
O2 S1 N1 C1 45.3(2)
O3 S1 N1 C1 174.74(17)
C16 S1 N1 C1 -69.99(19)
O2 S1 N1 C8 -176.83(16)
O3 S1 N1 C8 -47.36(19)
C16 S1 N1 C8 67.90(18)
C8 N1 C1 C2 161.6(2)
S1 N1 C1 C2 -59.7(3)
C8 N1 C1 C6 -13.5(3)
S1 N1 C1 C6 125.2(2)
C6 C1 C2 C3 -3.9(4)
N1 C1 C2 C3 -179.1(2)
C1 C2 C3 C4 2.8(4)
C2 C3 C4 C5 .3(4)
C2 C3 C4 Cl1 179.6(2)
C3 C4 C5 C6 -2.1(4)
Cl1 C4 C5 C6 178.56(19)
C7 O1 C6 C5 166.0(2)
C7 O1 C6 C1 -15.8(3)
C4 C5 C6 O1 179.2(2)
C4 C5 C6 C1 .9(4)
C2 C1 C6 O1 -176.1(2)
N1 C1 C6 O1 -.9(4)
C2 C1 C6 C5 2.0(4)
N1 C1 C6 C5 177.2(2)
C6 O1 C7 C8 44.2(3)
C1 N1 C8 C9 -133.0(2)
S1 N1 C8 C9 86.9(3)
C1 N1 C8 C7 43.1(3)
S1 N1 C8 C7 -97.1(2)
O1 C7 C8 C9 116.7(3)
O1 C7 C8 N1 -59.4(3)
N1 C8 C9 C10 3.4(4)
C7 C8 C9 C10 -172.3(2)
C8 C9 C10 C11 -165.4(3)
C8 C9 C10 C15 19.2(4)
C15 C10 C11 C12 -.7(4)
C9 C10 C11 C12 -176.3(2)
C10 C11 C12 C13 1.2(4)
C10 C11 C12 Cl2 179.95(18)
C11 C12 C13 C14 -.7(4)
Cl2 C12 C13 C14 -179.5(2)
C12 C13 C14 C15 -.3(5)
C13 C14 C15 C10 .7(5)
C11 C10 C15 C14 -.3(4)
C9 C10 C15 C14 175.1(3)
O2 S1 C16 C17 139.9(2)
O3 S1 C16 C17 6.9(2)
N1 S1 C16 C17 -106.4(2)
O2 S1 C16 C21 -43.7(2)
O3 S1 C16 C21 -176.70(19)
N1 S1 C16 C21 70.0(2)
C21 C16 C17 C18 -.1(4)
S1 C16 C17 C18 176.2(2)
C16 C17 C18 C19 -1.5(4)
C17 C18 C19 C20 2.1(4)
C17 C18 C19 C22 -177.8(3)
C18 C19 C20 C21 -1.1(4)
C22 C19 C20 C21 178.8(3)
C19 C20 C21 C16 -.4(4)
C17 C16 C21 C20 1.1(4)
S1 C16 C21 C20 -175.3(2)