#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/54/2005461.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_2005461
loop_
_publ_author_name
'Kumaradhas, P.'
'Nirmala, K. A.'
'Sridhar, M. A.'
_publ_section_title
cis-(+-)-5-[2-(Dimethylamino)ethyl]-3-hydroxy-2-(4-methoxyphenyl)-2,3,4,5-tetrahydro-1,5-benzothiazepin-4-one
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              2595
_journal_page_last               2597
_journal_paper_doi               10.1107/S0108270196005070
_journal_volume                  52
_journal_year                    1996
_chemical_formula_iupac          'C20 H24 N2 O3 S1'
_chemical_formula_moiety         'C20 H24 N2 O3 S1'
_chemical_formula_sum            'C20 H24 N2 O3 S'
_chemical_formula_weight         372.47
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c n'
_atom_type_scat_source           'SHELXL93 (Sheldrick, 1993)'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.447(1)
_cell_length_b                   12.989(1)
_cell_length_c                   24.881(1)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    294
_cell_measurement_theta_max      11
_cell_measurement_theta_min      5
_cell_volume                     3699.4(5)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction        'NRCVAX DATRD2 (Gabe et al., 1987)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976) in NRCVAX'
_computing_publication_material  SHELXL93
_computing_structure_refinement
'SHELXL93 (Sheldrick, 1993). Geometrical calculations: PARST (Nardelli, 1983)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.7093
_diffrn_reflns_av_R_equivalents  0
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3252
_diffrn_reflns_theta_max         24.9
_diffrn_standards_decay_%        <2
_diffrn_standards_interval_time  60
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.198
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_meas      1.337
_exptl_crystal_density_method    'flotation in a xylene/CCl~4~ mixture'
_exptl_crystal_description       'Rectangular block'
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.239
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   1.205
_refine_ls_hydrogen_treatment    'H atoms refined as riding'
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3252
_refine_ls_R_factor_obs          0.0486
_refine_ls_shift/esd_max         0.061
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
;
calc w = 1/[\s^2^(F~o~^2^) + (0.0691P)^2^]
where P = (F~o~^2^ + 2F~c~^2^)/3
;
_refine_ls_wR_factor_obs         0.1087
_reflns_number_observed          1847
_reflns_number_total             3252
_reflns_observed_criterion       I>2\s(I)
_cod_data_source_file            bk1153.cif
_cod_data_source_block           structure
_cod_original_cell_volume        3699.2(5)
_cod_original_formula_sum        'C20 H24 N2 O3 S1'
_cod_database_code               2005461
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_type_symbol
C(1) 0.0025(3) 0.5470(2) 0.4393(1) 0.054(8) C
C(2) 0.0425(2) 0.4615(2) 0.4116(1) 0.039(6) C
C(3) -0.0381(2) 0.3955(2) 0.3876(1) 0.036(6) C
C(4) -0.1568(2) 0.4162(2) 0.3917(1) 0.045(7) C
C(5) -0.1949(3) 0.5007(2) 0.4201(1) 0.056(8) C
C(6) -0.1154(3) 0.5653(2) 0.4443(1) 0.060(9) C
S(7) 0.1938(6) 0.4329(6) 0.4121(3) 0.050(2) S
C(8) 0.2337(2) 0.4452(2) 0.3410(1) 0.042(7) C
C(9) 0.3495(2) 0.3912(2) 0.3335(1) 0.039(7) C
C(10) 0.3641(2) 0.2861(2) 0.3410(1) 0.046(7) C
C(11) 0.4706(2) 0.2389(2) 0.3321(1) 0.046(7) C
C(12) 0.5657(2) 0.2972(2) 0.3167(1) 0.038(6) C
C(13) 0.5544(2) 0.4027(2) 0.3117(1) 0.045(7) C
C(14) 0.4470(2) 0.4481(2) 0.3193(1) 0.042(7) C
O(15) 0.6745(2) 0.2569(2) 0.3048(8) 0.052(5) O
C(16) 0.6815(3) 0.1495(2) 0.2929(1) 0.056(8) C
C(17) 0.1311(2) 0.4104(2) 0.3040(9) 0.039(6) C
O(18) 0.1693(2) 0.4078(2) 0.2498(7) 0.052(5) O
C(19) 0.0810(2) 0.3063(2) 0.3203(1) 0.039(6) C
O(20) 0.1123(2) 0.2274(2) 0.2975(7) 0.052(5) O
N(21) -0.0014(2) 0.3049(2) 0.3597(9) 0.036(5) N
C(22) -0.0502(2) 0.2050(2) 0.3754(1) 0.045(7) C
C(23) 0.0240(2) 0.1503(2) 0.4167(1) 0.049(7) C
N(24) 0.0276(2) 0.2004(2) 0.4692(1) 0.049(6) N
C(25) -0.0836(3) 0.1892(3) 0.4969(1) 0.080(1) C
C(26) 0.1206(4) 0.1558(3) 0.5008(2) 0.093(1) C
H(1) 0.0557(3) 0.5925(2) 0.4546(1) 0.065(2) H
H(4) -0.2107(2) 0.3729(2) 0.3752(1) 0.054(2) H
H(5) -0.2744(3) 0.5142(2) 0.4229(1) 0.067(2) H
H(6) -0.1415(3) 0.6215(2) 0.4641(1) 0.071(2) H
H(8) 0.2470(2) 0.5185(2) 0.3340(1) 0.050(2) H
H(10) 0.3009(2) 0.2466(2) 0.3523(1) 0.055(2) H
H(11) 0.4782(2) 0.1681(2) 0.3364(1) 0.056(2) H
H(13) 0.6191(2) 0.4428(2) 0.3033(1) 0.054(2) H
H(14) 0.4397(2) 0.5189(2) 0.3148(1) 0.050(2) H
H(16A) 0.6709(2) 0.1105(2) 0.3253(2) 0.085(4) H
H(16B) 0.7567(6) 0.1342(3) 0.2778(7) 0.085(4) H
H(16C) 0.6216(1) 0.1316(4) 0.2675(6) 0.085(4) H
H(17) 0.0687(2) 0.4617(2) 0.3069(9) 0.046(2) H
H(18) 0.199(3) 0.3520(11) 0.2433(4) 0.102(4) H
H(22A) -0.0573(2) 0.1619(2) 0.3438(1) 0.054(2) H
H(22B) -0.1279(2) 0.2154(2) 0.3900(1) 0.054(2) H
H(23A) -0.0058(2) 0.0809(2) 0.4212(1) 0.059(2) H
H(23B) 0.1031(2) 0.1450(2) 0.4030(1) 0.059(2) H
H(25A) -0.1436(5) 0.2240(2) 0.4770(5) 0.119(4) H
H(25B) -0.0778(8) 0.2188(2) 0.5322(4) 0.119(4) H
H(25C) -0.1027(1) 0.1175(3) 0.4999(9) 0.119(4) H
H(26A) 0.1222(2) 0.1875(2) 0.5356(4) 0.139(4) H
H(26B) 0.1940(4) 0.1672(2) 0.4830(6) 0.139(4) H
H(26C) 0.1075(1) 0.0832(5) 0.5046(1) 0.139(4) H
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C(6) C(1) C(2) 120.5(3) yes
C(6) C(1) H(1) 119.7(2) ?
C(2) C(1) H(1) 119.7(2) ?
C(1) C(2) C(3) 119.1(3) yes
C(10) C(2) S(7) 119.3(2) yes
C(3) C(2) S(7) 121.4(2) yes
C(4) C(3) C(2) 119.8(2) yes
C(4) C(3) N(21) 118.9(2) yes
C(2) C(3) N(21) 121.3(2) yes
C(5) C(4) C(3) 120.2(3) yes
C(5) C(4) H(4) 119.9(2) ?
C(3) C(4) H(4) 119.9(2) ?
C(4) C(5) C(6) 120.1(3) yes
C(4) C(5) H(5) 119.9(2) ?
C(6) C(5) H(5) 120.0(2) ?
C(5) C(6) C(1) 120.2(3) yes
C(5) C(6) H(6) 119.9(2) ?
C(1) C(6) H(6) 119.9(2) ?
C(2) S(7) C(8) 102.70(10) yes
C(9) C(8) C(17) 116.9(2) yes
C(9) C(8) S(7) 107.4(2) yes
C(17) C(8) S(7) 110.9(2) ?
C(9) C(8) H(8) 107.10(10) ?
C(17) C(8) H(8) 107.10(10) ?
S(7) C(8) H(8) 107.1(9) ?
C(14) C(9) C(10) 117.6(3) yes
C(14) C(9) C(8) 119.4(2) yes
C(10) C(9) C(8) 123.0(2) yes
C(11) C(10) C(9) 121.4(3) yes
C(11) C(10) H(10) 119.3(2) ?
C(9) C(10) H(10) 119.3(2) ?
C(12) C(11) C(10) 119.8(3) yes
C(12) C(11) H(11) 120.1(2) ?
C(10) C(11) H(11) 120.1(2) ?
C(11) C(12) C(13) 119.7(3) yes
C(11) C(12) O(15) 124.2(3) yes
C(13) C(12) O(15) 116.1(2) yes
C(14) C(13) C(12) 119.8(3) yes
C(14) C(13) H(13) 120.1(2) ?
C(12) C(13) H(13) 120.1(2) ?
C(13) C(14) C(9) 121.7(3) yes
C(13) C(14) H(14) 119.1(2) ?
C(9) C(14) H(14) 119.1(2) ?
C(12) O(15) C(16) 117.7(2) yes
O(15) C(16) H(16A) 109.5(2) ?
O(15) C(16) H(16B) 109.50(10) ?
H(16A) C(16) H(16B) 109.5(6) ?
O(15) C(16) H(16C) 109.5(2) ?
H(16A) C(16) H(16C) 109.5(6) ?
H(16B) C(16) H(16C) 109.5(8) ?
O(18) C(17) C(19) 110.4(2) yes
O(18) C(17) C(8) 109.7(2) yes
C(19) C(17) C(8) 112.5(2) yes
O(18) C(17) H(17) 108.00(10) ?
C(19) C(17) H(17) 108.00(10) ?
C(8) C(17) H(17) 108.00(10) ?
C(17) O(18) H(18) 109.60(10) ?
O(20) C(19) N(21) 121.7(3) yes
O(20) C(19) C(17) 120.5(2) yes
N(21) C(19) C(17) 117.7(2) yes
C(19) N(21) C(3) 122.9(2) yes
C(19) N(21) C(22) 118.0(2) yes
C(3) N(21) C(22) 119.1(2) yes
N(21) C(22) C(23) 112.6(2) yes
N(21) C(22) H(22A) 109.10(10) ?
C(23) C(22) H(22A) 109.1(2) ?
N(21) C(22) H(22B) 109.10(10) ?
C(23) C(22) H(22B) 109.1(2) ?
H(22A) C(22) H(22B) 107.8(4) ?
N(24) C(23) C(22) 114.5(2) yes
N(24) C(23) H(23A) 108.70(10) ?
C(22) C(23) H(23A) 108.7(2) ?
N(24) C(23) H(23B) 108.70(10) ?
C(22) C(23) H(23B) 108.6(2) ?
H(23A) C(23) H(23B) 107.6(4) ?
C(26) N(24) C(25) 110.3(3) yes
C(26) N(24) C(23) 109.2(3) yes
C(25) N(24) C(23) 110.8(2) yes
N(24) C(25) H(25A) 109.5(2) ?
N(24) C(25) H(25B) 109.5(2) ?
H(25A) C(25) H(25B) 109.5(2) ?
N(24) C(25) H(25C) 109.5(2) ?
H(25A) C(25) H(25C) 109.5(9) ?
H(25B) C(25) H(25C) 109.50(10) ?
N(24) C(26) H(26A) 109.5(2) ?
N(24) C(26) H(26B) 109.5(2) ?
H(26A) C(26) H(26B) 109.5(2) ?
N(24) C(26) H(26C) 109.5(2) ?
H(26A) C(26) H(26C) 109.5(3) ?
H(26B) C(26) H(26C) 109.5(4) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C(1) C(6) 1.376(4) yes
C(1) C(2) 1.385(4) yes
C(1) H(1) 0.930(4) ?
C(2) C(3) 1.394(4) yes
C(2) S(7) 1.771(3) yes
C(3) C(4) 1.390(3) yes
C(3) N(21) 1.430(3) yes
C(4) C(5) 1.375(4) yes
C(4) H(4) 0.930(4) ?
C(5) C(6) 1.376(4) yes
C(5) H(5) 0.930(5) ?
C(6) H(6) 0.930(4) ?
S(7) C(8) 1.833(3) yes
C(8) C(9) 1.511(4) yes
C(8) C(17) 1.559(4) yes
C(8) H(8) 0.980(4) ?
C(9) C(14) 1.384(4) yes
C(9) C(10) 1.388(4) yes
C(10) C(11) 1.383(4) yes
C(10) H(10) 0.930(4) ?
C(11) C(12) 1.380(4) yes
C(11) H(11) 0.930(4) ?
C(12) C(13) 1.382(4) yes
C(12) O(15) 1.382(3) yes
C(13) C(14) 1.377(4) yes
C(13) H(13) 0.930(4) ?
C(14) H(14) 0.930(4) ?
O(15) C(16) 1.429(3) yes
C(16) H(16A) 0.960(6) ?
C(16) H(16B) 0.960(1) ?
C(16) H(16C) 0.961(3) ?
C(17) O(18) 1.418(3) yes
C(17) C(19) 1.525(4) yes
C(17) H(17) 0.98O(4) ?
O(18) H(18) 0.820(3) ?
C(19) O(20) 1.226(3) yes
C(19) N(21) 1.359(3) yes
N(21) C(22) 1.465(3) yes
C(22) C(23) 1.509(4) yes
C(22) H(22A) 0.970(4) ?
C(22) H(22B) 0.970(4) ?
C(23) N(24) 1.461(4) yes
C(23) H(23A) 0.970(4) ?
C(23) H(23B) 0.970(4) ?
N(24) C(26) 1.445(4) yes
N(24) C(25) 1.455(4) yes
C(25) H(25A) 0.961(4) ?
C(25) H(25B) 0.961(3) ?
C(25) H(25C) 0.960(6) ?
C(26) H(26A) 0.961(3) ?
C(26) H(26B) 0.960(9) ?
C(26) H(26C) 0.960(8) ?
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) 1.6(4)
C(6) C(1) C(2) S(7) -173.3(2)
C(1) C(2) C(3) C(4) 0.1(4)
S(7) C(2) C(3) C(4) 174.9(2)
C(1) C(2) C(3) N(21) -178.6(2)
S(7) C(2) C(3) N(21) -3.8(3)
C(2) C(3) C(4) C(5) -1.1(4)
N(21) C(3) C(4) C(5) 177.6(2)
C(3) C(4) C(5) C(6) 0.4(4)
C(4) C(5) C(6) C(1) 1.4(4)
C(2) C(1) C(6) C(5) -2.4(4)
C(1) C(2) S(7) C(8) -116.9(2)
C(3) C(2) S(7) C(8) 68.3(2)
C(2) S(7) C(8) C(9) -162.6(2)
C(2) S(7) C(8) C(17) -33.8(2)
C(17) C(8) C(9) C(14) 120.1(3)
S(7) C(8) C(9) C(14) -114.6(2)
C(17) C(8) C(9) C(10) -61.1(3)
S(7) C(8) C(9) C(10) 64.2(3)
C(14) C(9) C(10) C(11) -3.2(4)
C(8) C(9) C(10) C(11) 177.9(2)
C(9) C(10) C(11) C(12) 1.7(4)
C(10) C(11) C(12) C(13) 1.7(4)
C(10) C(11) C(12) O(15) -177.4(2)
C(11) C(12) C(13) C(14) -3.5(4)
O(15) C(12) C(13) C(14) 175.7(2)
C(12) C(13) C(14) C(9) 2.0(4)
C(10) C(9) C(14) C(13) 1.4(4)
C(8) C(9) C(14) C(13) -179.7(2)
C(11) C(12) O(15) C(16) 18.5(4)
C(13) C(12) O(15) C(16) -160.7(2)
C(9) C(8) C(17) O(18) -48.9(8)
S(7) C(8) C(17) O(18) -172.4(2)
C(9) C(8) C(17) C(19) 74.4(3)
S(7) C(8) C(17) C(19) -49.1(3)
O(18) C(17) C(19) O(20) 25.6(3)
C(8) C(17) C(19) O(20) -97.3(3)
O(18) C(17) C(19) N(21) -152.5(2)
C(8) C(17) C(19) N(21) 84.6(3)
O(20) C(19) N(21) C(3) 178.9(2)
C(17) C(19) N(21) C(3) -3.1(3)
O(20) C(19) N(21) C(22) 1.8(4)
C(17) C(19) N(21) C(22) 179.8(2)
C(4) C(3) N(21) C(19) 129.4(3)
C(2) C(3) N(21) C(19) -51.9(3)
C(4) C(3) N(21) C(22) -53.5(3)
C(2) C(3) N(21) C(22) 125.1(3)
C(19) N(21) C(22) C(23) 84.7(3)
C(3) N(21) C(22) C(23) -92.5(3)
N(21) C(22) C(23) N(24) 67.3(3)
C(22) C(23) N(24) C(26) -166.8(3)
C(22) C(23) N(24) C(25) 71.5(3)
