#------------------------------------------------------------------------------
#$Date: 2015-04-02 12:22:18 +0100 (Thu, 02 Apr 2015) $
#$Revision: 134621 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/83/2008309.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_2008309
loop_
_publ_author_name
'Kumaradhas, P.'
'Kalyanam, N.'
'Ravikumar, K.'
'Chandra Mohan, K.'
'Sridhar, M.A.'
'Shashidhara Prasad, J.'
'Nirmala, K.A.'
_publ_section_title
;(+)-<i>cis</i>-3-Hydroxy-2-(4-methoxyphenyl)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepine
 1-oxide
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              614
_journal_page_last               615
_journal_paper_doi               10.1107/S0108270198012827
_journal_volume                  55
_journal_year                    1999
_chemical_formula_moiety         'C16 H15 N O4 S'
_chemical_formula_sum            'C16 H15 N O4 S'
_chemical_formula_weight         317.35
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_type_scat_source           'SHELXL93 (Sheldrick, 1993)'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.6980(10)
_cell_length_b                   7.1710(10)
_cell_length_c                   30.604(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      19
_cell_measurement_theta_min      8
_cell_volume                     1470.0(4)
_computing_cell_refinement       'R3m/V Software'
_computing_data_collection       'R3m/V Software (Siemens, 1983)'
_computing_data_reduction        'SHELXTL-Plus (Sheldrick, 1990a)'
_computing_molecular_graphics
'ORTEPII (Johnson, 1976) in NRCVAX (Gabe et al., 1989)'
_computing_publication_material  SHELXL93
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990b)'
_diffrn_measurement_device       'Siemens R3m/V'
_diffrn_measurement_method       \w
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0802
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1591
_diffrn_reflns_theta_max         25.03
_diffrn_standards_decay_%        <1
_diffrn_standards_interval_count 98
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.238
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_meas      1.423(3)
_exptl_crystal_density_method    'flotation in xylene-CCl~4~'
_exptl_crystal_description       Equidimensional
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.217
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   1.120
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_parameters     199
_refine_ls_number_reflns         1527
_refine_ls_R_factor_obs          0.0438
_refine_ls_shift/esd_max         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0452P)^2^+0.0522P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.0897
_reflns_number_observed          1171
_reflns_number_total             1527
_reflns_observed_criterion       I>2sigma(I)
_[local]_cod_data_source_file    bk1392.cif
_[local]_cod_data_source_block   k1486
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'None' changed to 'none'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.0452P)^2^+0.0522P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w =
1/[\s^2^(Fo^2^)+(0.0452P)^2^+0.0522P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_database_code               2008309
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
1/2-x,-y,1/2+z
-x,1/2+y,1/2-z
1/2+x,1/2-y,-z
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
C(1) 0.042(3) 0.039(3) 0.036(2) 0.008(3) 0.009(2) 0.003(2)
C(2) 0.032(2) 0.037(3) 0.034(2) 0.003(2) -0.001(2) 0.001(2)
C(3) 0.035(3) 0.032(3) 0.035(2) 0.004(2) 0.000(2) 0.001(2)
C(4) 0.047(3) 0.036(3) 0.044(3) 0.000(3) -0.011(2) 0.000(2)
C(5) 0.072(4) 0.044(3) 0.034(3) 0.003(3) -0.003(3) 0.001(2)
C(6) 0.064(4) 0.052(3) 0.031(3) 0.008(3) 0.012(2) 0.008(2)
C(9) 0.031(2) 0.038(3) 0.030(2) 0.008(3) 0.000(2) 0.002(2)
C(10) 0.032(2) 0.038(3) 0.032(2) -0.002(3) 0.002(2) -0.003(2)
C(11) 0.037(3) 0.045(3) 0.032(2) 0.011(3) 0.007(2) 0.002(2)
C(12) 0.046(3) 0.047(3) 0.033(2) 0.007(3) -0.001(2) 0.008(2)
C(13) 0.048(3) 0.035(3) 0.029(2) -0.003(3) 0.005(2) -0.003(2)
C(14) 0.048(3) 0.056(3) 0.036(3) 0.018(3) 0.004(2) -0.005(3)
C(15) 0.038(3) 0.061(4) 0.036(3) 0.014(3) -0.008(2) -0.005(3)
C(17) 0.089(4) 0.072(4) 0.041(3) 0.023(4) 0.005(3) -0.014(3)
C(18) 0.034(3) 0.038(3) 0.026(2) 0.001(2) 0.001(2) 0.002(2)
C(20) 0.031(3) 0.045(3) 0.035(3) -0.004(2) 0.001(2) 0.000(2)
N(22) 0.031(2) 0.047(3) 0.037(2) 0.004(2) 0.002(2) 0.005(2)
O(8) 0.032(2) 0.055(2) 0.052(2) -0.010(2) -0.006(2) 0.009(2)
O(16) 0.062(2) 0.059(2) 0.029(2) 0.016(2) 0.001(2) -0.003(2)
O(19) 0.050(2) 0.040(2) 0.054(2) -0.002(2) -0.001(2) 0.013(2)
O(21) 0.042(2) 0.083(3) 0.047(2) -0.003(2) 0.014(2) 0.018(2)
S(7) 0.0341(6) 0.0364(6) 0.0348(6) -0.0006(7) -0.0018(5) 0.0007(5)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
C(1) 0.3960(7) 0.0453(6) 0.75310(10) 0.0390(10) Uani d . 1 . C
H(1) 0.5286 0.0821 0.75586 0.047 Uiso calc R 1 . H
C(2) 0.2772(7) 0.0223(7) 0.78960(10) 0.0340(10) Uani d . 1 . C
C(3) 0.0779(7) -0.0290(6) 0.78620(10) 0.0340(10) Uani d . 1 . C
C(4) -0.0029(9) -0.0589(6) 0.74520(10) 0.0420(10) Uani d . 1 . C
H(4) -0.1359 -0.0941 0.74232 0.051 Uiso calc R 1 . H
C(5) 0.1153(9) -0.0363(7) 0.70830(10) 0.05000(10) Uani d . 1 . C
H(5) 0.0599 -0.0544 0.68080 0.060 Uiso calc R 1 . H
C(6) 0.3139(8) 0.0125(7) 0.71200(10) 0.0490(10) Uani d . 1 . C
H(6) 0.3926 0.0235 0.68704 0.059 Uiso calc R 1 . H
C(9) 0.3687(7) -0.1282(6) 0.87310(10) 0.0330(10) Uani d . 1 . C
H(9) 0.4970 -0.1898 0.86768 0.040 Uiso calc R 1 . H
C(10) 0.3652(7) -0.0776(7) 0.92110(10) 0.0340(10) Uani d . 1 . C
C(11) 0.5043(7) -0.1543(6) 0.94920(10) 0.0380(10) Uani d . 1 . C
H(11) 0.5998 -0.2363 0.93838 0.046 Uiso calc R 1 . H
C(12) 0.5037(7) -0.1109(7) 0.99340(10) 0.0420(10) Uani d . 1 . C
H(12) 0.5960 -0.1662 1.01207 0.051 Uiso calc R 1 . H
C(13) 0.3656(8) 0.0148(6) 1.00980(10) 0.0370(10) Uani d . 1 . C
C(14) 0.2238(7) 0.0915(8) 0.98240(10) 0.0470(10) Uani d . 1 . C
H(14) 0.1282 0.1730 0.99342 0.056 Uiso calc R 1 . H
C(15) 0.2252(7) 0.0457(7) 0.93840(10) 0.0450(10) Uani d . 1 . C
H(15) 0.1304 0.0985 0.91993 0.054 Uiso calc R 1 . H
C(17) 0.2345(9) 0.1679(8) 1.0732(2) 0.067(2) Uani d . 1 . C
H(17A) 0.2646 0.1841 1.1036 0.101 Uiso calc R 1 . H
H(17B) 0.1064 0.1091 1.0702 0.101 Uiso calc R 1 . H
H(17C) 0.2321 0.2873 1.0590 0.101 Uiso calc R 1 . H
C(18) 0.2049(6) -0.2642(6) 0.85750(10) 0.0330(10) Uani d . 1 . C
H(18) 0.2374 -0.3023 0.82756 0.039 Uiso calc R 1 . H
C(20) -0.0007(7) -0.1748(7) 0.85690(10) 0.0370(10) Uani d . 1 . C
N(22) -0.0399(6) -0.0513(6) 0.82430(10) 0.0380(10) Uani d . 1 . N
H(22) -0.1437 0.0183 0.82705 0.046 Uiso calc R 1 . H
O(8) 0.5886(4) 0.1382(5) 0.83440(10) 0.0460(10) Uani d . 1 . O
O(16) 0.3825(5) 0.0544(5) 1.05360(10) 0.0500(10) Uani d . 1 . O
O(19) 0.2059(5) -0.4247(5) 0.88390(10) 0.0480(10) Uani d . 1 . O
H(19) 0.0943 -0.4408 0.89425 0.072 Uiso calc R 1 . H
O(21) -0.1230(5) -0.2132(6) 0.88490(10) 0.0570(10) Uani d . 1 . O
S(7) 0.3732(2) 0.0945(2) 0.84201(4) 0.0351(3) Uani d . 1 . S
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C(2) C(1) C(6) 118.9(5)
C(2) C(1) H(1) 120.6(3)
C(6) C(1) H(1) 120.6(3)
C(1) C(2) C(3) 121.6(4)
C(1) C(2) S(7) 118.7(4)
C(3) C(2) S(7) 119.1(3)
C(4) C(3) C(2) 119.1(5)
C(4) C(3) N(22) 120.8(4)
C(2) C(3) N(22) 120.1(4)
C(3) C(4) C(5) 119.7(5)
C(3) C(4) H(4) 120.1(3)
C(5) C(4) H(4) 120.1(3)
C(6) C(5) C(4) 121.0(5)
C(6) C(5) H(5) 119.5(3)
C(4) C(5) H(5) 119.5(3)
C(5) C(6) C(1) 119.7(5)
C(5) C(6) H(6) 120.1(3)
C(1) C(6) H(6) 120.1(3)
C(10) C(9) C(18) 116.2(4)
C(10) C(9) S(7) 106.9(3)
C(18) C(9) S(7) 113.3(3)
C(10) C(9) H(9) 106.6(3)
C(18) C(9) H(9) 106.6(2)
S(7) C(9) H(9) 106.63(14)
C(11) C(10) C(15) 118.0(4)
C(11) C(10) C(9) 119.9(4)
C(15) C(10) C(9) 122.1(4)
C(10) C(11) C(12) 121.1(4)
C(10) C(11) H(11) 119.5(2)
C(12) C(11) H(11) 119.5(3)
C(13) C(12) C(11) 120.0(4)
C(13) C(12) H(12) 120.0(3)
C(11) C(12) H(12) 120.0(3)
O(16) C(13) C(14) 124.4(4)
O(16) C(13) C(12) 115.5(4)
C(14) C(13) C(12) 120.0(4)
C(13) C(14) C(15) 119.3(5)
C(13) C(14) H(14) 120.3(3)
C(15) C(14) H(14) 120.3(3)
C(14) C(15) C(10) 121.6(4)
C(14) C(15) H(15) 119.2(3)
C(10) C(15) H(15) 119.2(2)
O(16) C(17) H(17A) 109.5(3)
O(16) C(17) H(17B) 109.5(3)
H(17A) C(17) H(17B) 109.5
O(16) C(17) H(17C) 109.5(3)
H(17A) C(17) H(17C) 109.5
H(17B) C(17) H(17C) 109.5
O(19) C(18) C(20) 110.9(4)
O(19) C(18) C(9) 109.6(3)
C(20) C(18) C(9) 112.4(4)
O(19) C(18) H(18) 107.9(2)
C(20) C(18) H(18) 107.9(2)
C(9) C(18) H(18) 107.9(2)
O(21) C(20) N(22) 122.3(4)
O(21) C(20) C(18) 120.4(4)
N(22) C(20) C(18) 117.3(4)
C(20) N(22) C(3) 124.7(4)
C(20) N(22) H(22) 117.6(3)
C(3) N(22) H(22) 117.6(2)
C(13) O(16) C(17) 118.3(4)
C(18) O(19) H(19) 109.5(2)
O(8) S(7) C(2) 105.5(2)
O(8) S(7) C(9) 106.0(2)
C(2) S(7) C(9) 101.7(2)
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
C(1) C(2) . 1.383(6) ?
C(1) C(6) . 1.393(6) ?
C(1) H(1) . 0.93 ?
C(2) C(3) . 1.388(6) ?
C(2) S(7) . 1.803(4) ?
C(3) C(4) . 1.383(6) ?
C(3) N(22) . 1.419(5) ?
C(4) C(5) . 1.387(7) ?
C(4) H(4) . 0.93 ?
C(5) C(6) . 1.380(7) ?
C(5) H(5) . 0.93 ?
C(6) H(6) . 0.93 ?
C(9) C(10) . 1.512(5) ?
C(9) C(18) . 1.544(6) ?
C(9) S(7) . 1.859(4) ?
C(9) H(9) . 0.98 ?
C(10) C(11) . 1.384(6) ?
C(10) C(15) . 1.393(6) ?
C(11) C(12) . 1.388(6) ?
C(11) H(11) . 0.93 ?
C(12) C(13) . 1.385(6) ?
C(12) H(12) . 0.93 ?
C(13) O(16) . 1.376(5) ?
C(13) C(14) . 1.380(6) ?
C(14) C(15) . 1.389(6) ?
C(14) H(14) . 0.93 ?
C(15) H(15) . 0.93 ?
C(17) O(16) . 1.416(6) ?
C(17) H(17A) . 0.96 ?
C(17) H(17B) . 0.96 ?
C(17) H(17C) . 0.96 ?
C(18) O(19) . 1.407(5) ?
C(18) C(20) . 1.519(6) ?
C(18) H(18) . 0.98 ?
C(20) O(21) . 1.218(5) ?
C(20) N(22) . 1.359(5) ?
N(22) H(22) . 0.86 ?
O(8) S(7) . 1.495(3) ?
O(19) H(19) . 0.82 ?
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
O(19) H(19) O(16) 1_455 0.82 2.285(3) 3.036(5) 152.4(2)
N(22) H(22) O(8) 4_447 0.86 2.001(3) 2.852(5) 169.9(3)
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
C(6) C(1) C(2) C(3) -1.3(7)
C(6) C(1) C(2) S(7) -171.8(4)
C(1) C(2) C(3) C(4) 0.5(7)
S(7) C(2) C(3) C(4) 171.0(4)
C(1) C(2) C(3) N(22) -180.0(4)
S(7) C(2) C(3) N(22) -9.5(6)
C(2) C(3) C(4) C(5) -0.4(7)
N(22) C(3) C(4) C(5) -179.9(4)
C(3) C(4) C(5) C(6) 1.1(7)
C(4) C(5) C(6) C(1) -2.0(8)
C(2) C(1) C(6) C(5) 2.0(7)
C(18) C(9) C(10) C(11) 104.9(5)
S(7) C(9) C(10) C(11) -127.5(4)
C(18) C(9) C(10) C(15) -75.2(6)
S(7) C(9) C(10) C(15) 52.4(5)
C(15) C(10) C(11) C(12) 0.4(7)
C(9) C(10) C(11) C(12) -179.7(4)
C(10) C(11) C(12) C(13) -1.7(7)
C(11) C(12) C(13) O(16) -177.4(4)
C(11) C(12) C(13) C(14) 2.5(7)
O(16) C(13) C(14) C(15) 177.9(5)
C(12) C(13) C(14) C(15) -2.0(8)
C(13) C(14) C(15) C(10) 0.7(8)
C(11) C(10) C(15) C(14) 0.1(8)
C(9) C(10) C(15) C(14) -179.8(5)
C(10) C(9) C(18) O(19) -52.9(5)
S(7) C(9) C(18) O(19) -177.3(3)
C(10) C(9) C(18) C(20) 70.8(5)
S(7) C(9) C(18) C(20) -53.5(4)
O(19) C(18) C(20) O(21) 17.8(6)
C(9) C(18) C(20) O(21) -105.2(5)
O(19) C(18) C(20) N(22) -162.6(4)
C(9) C(18) C(20) N(22) 74.3(5)
O(21) C(20) N(22) C(3) -166.5(5)
C(18) C(20) N(22) C(3) 14.0(6)
C(4) C(3) N(22) C(20) 119.6(5)
C(2) C(3) N(22) C(20) -60.0(6)
C(14) C(13) O(16) C(17) 6.1(7)
C(12) C(13) O(16) C(17) -174.1(4)
C(1) C(2) S(7) O(8) -9.5(4)
C(3) C(2) S(7) O(8) 179.7(4)
C(1) C(2) S(7) C(9) -119.9(4)
C(3) C(2) S(7) C(9) 69.3(4)
C(10) C(9) S(7) O(8) 92.2(3)
C(18) C(9) S(7) O(8) -138.5(3)
C(10) C(9) S(7) C(2) -157.8(3)
C(18) C(9) S(7) C(2) -28.5(4)