#------------------------------------------------------------------------------
#$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $
#$Revision: 301803 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/01/2200137.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_2200137
loop_
_publ_author_name
'Zerzouf, A.'
'El Meslouhi, H.'
'Salem, M.'
'Essassi, E. M.'
'Pierrot, M.'
_publ_section_title
;
 Methyl (3-hydroxy-4-oxo-2-phenyl-1,5-benzothiazepin-5-yl)acetate
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o362
_journal_page_last               o363
_journal_paper_doi               10.1107/S1600536801004846
_journal_volume                  57
_journal_year                    2001
_chemical_formula_iupac          'C18 H17 N O4 S'
_chemical_formula_moiety         'C18 H17 N O4 S'
_chemical_formula_sum            'C18 H17 N O4 S'
_chemical_formula_weight         343.401
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_cell_angle_alpha                90.000(4)
_cell_angle_beta                 151.086(3)
_cell_angle_gamma                90.000(10)
_cell_formula_units_Z            4
_cell_length_a                   13.6308(8)
_cell_length_b                   15.1336(9)
_cell_length_c                   16.1540(10)
_cell_measurement_reflns_used    ' 10319'
_cell_measurement_temperature    298
_cell_measurement_theta_max      26.40
_cell_measurement_theta_min      1
_cell_volume                     1611.2(2)
_computing_data_collection       'KappaCCD Reference Manual (Nonius, 1998)'
_computing_data_reduction
'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  maXus
_computing_structure_refinement  'maXus (Mackay et al., 1999)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_measurement_device       KappaCCD
_diffrn_measurement_method       \f
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_reflns_av_R_equivalents  .046
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            3302
_diffrn_reflns_theta_max         26.38
_exptl_absorpt_coefficient_mu    .223
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Violet
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             720
_exptl_crystal_size_max          .40
_exptl_crystal_size_mid          .30
_exptl_crystal_size_min          .20
_refine_diff_density_max         .24
_refine_diff_density_min         -.30
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.510
_refine_ls_goodness_of_fit_ref   1.364
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2569
_refine_ls_R_factor_all          .065
_refine_ls_R_factor_gt           .045
_refine_ls_shift/su_max          .015
_refine_ls_shift/su_mean         .003
_refine_ls_structure_factor_coef F^2^
_refine_ls_weighting_details     'w = 1/[\s^2^(Fo^2^) + 0.03Fo^2^]'
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_all         .050
_refine_ls_wR_factor_ref         .048
_reflns_number_gt                2569
_reflns_number_total             3156
_reflns_threshold_expression     I>3\s(I)
_cod_data_source_file            cf6057.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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:

'_atom_site_adp_type' tag value 'Uij' was replaced with 'Uani' value
24 times.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2200137
_cod_database_fobs_code          2200137
loop_
_symmetry_equiv_pos_as_xyz
+X,+Y,+Z
-X,-Y,-Z
'-X,+Y+ 1/2,-Z+ 1/2'
'+X,-Y+ 1/2,+Z+ 1/2'
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_occupancy
S1 .043323(18) .376328(8) -.016113(15) .09284(7) Uani 1.00
O18 -.01596(4) .32975(2) -.30649(4) .08259(17) Uani 1.00
O19 .29436(5) .43419(2) -.05234(4) .09537(18) Uani 1.00
O22 .67789(5) .30762(2) .20966(4) .1256(2) Uani 1.00
O23 .84397(5) .43524(2) .34720(4) .1122(2) Uani 1.00
N5 .41618(5) .35605(2) .14507(4) .06322(19) Uani 1.00
C2 -.07943(6) .36288(3) -.20796(5) .0685(2) Uani 1.00
C3 .07045(6) .32628(3) -.16231(5) .0662(2) Uani 1.00
C4 .26885(6) .37712(3) -.01795(5) .0697(2) Uani 1.00
C6 .39450(6) .29014(3) .19221(5) .0694(2) Uani 1.00
C7 .54413(7) .22635(3) .31138(6) .0874(3) Uani 1.00
C8 .53301(8) .16520(3) .36676(6) .1089(3) Uani 1.00
C9 .37105(9) .16700(3) .30134(7) .1261(3) Uani 1.00
C10 .21874(7) .22834(3) .17918(6) .1045(3) Uani 1.00
C11 .22828(6) .29122(3) .12267(5) .0748(2) Uani 1.00
C12 -.17461(6) .44937(3) -.30402(5) .0689(2) Uani 1.00
C13 -.08121(7) .53048(3) -.22189(6) .0922(3) Uani 1.00
C14 -.17508(9) .60806(3) -.31654(8) .1468(3) Uani 1.00
C15 -.36056(9) .60541(4) -.49229(8) .1517(4) Uani 1.00
C16 -.45319(7) .52573(4) -.57519(6) .1052(3) Uani 1.00
C17 -.36203(6) .44790(3) -.48200(6) .0810(3) Uani 1.00
C20 .61013(6) .40095(3) .27691(5) .0745(2) Uani 1.00
C21 .71033(6) .37427(3) .27050(5) .0656(2) Uani 1.00
C24 .95452(8) .41952(3) .35279(7) .1240(3) Uani 1.00
H2 -.18663 .32026 -.28222 .05276 Uiso 1.00
H3 .09793 .26565 -.12860 .05190 Uiso 1.00
H7 .65520 .22464 .35500 .06208 Uiso 1.00
H8 .63868 .12210 .45140 .07114 Uiso 1.00
H9 .36277 .12497 .33961 .07850 Uiso 1.00
H10 .10540 .22851 .13281 .07015 Uiso 1.00
H13 .04919 .53296 -.09917 .06338 Uiso 1.00
H14 -.11036 .66396 -.25939 .08474 Uiso 1.00
H15 -.42640 .65904 -.55783 .09155 Uiso 1.00
H16 -.58180 .52358 -.69803 .07708 Uiso 1.00
H17 -.42749 .39217 -.53998 .06170 Uiso 1.00
H18 .04986 .38758 -.28624 .06267 Uiso 1.00
H20A .69835 .38557 .38711 .05748 Uiso 1.00
H20B .58802 .46365 .26043 .05748 Uiso 1.00
H24A 1.04642 .46750 .41072 .08136 Uiso 1.00
H24B .86042 .41502 .23810 .08136 Uiso 1.00
H24C 1.02972 .36540 .41302 .08136 Uiso 1.00
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
S1 .04872(7) .04516(7) .04300(7) .00509(6) .04246(7) .00202(6)
O18 .04275(18) .0538(2) .03141(17) .00596(15) .03293(16) -.00048(14)
O19 .04561(19) .04791(19) .04614(19) .00379(15) .04120(18) .00991(15)
O22 .0573(2) .0458(2) .0696(2) -.00760(17) .0565(2) -.01519(18)
O23 .0495(2) .0456(2) .0631(2) -.01029(16) .0509(2) -.01049(17)
N5 .02961(19) .0412(2) .02628(19) -.00350(15) .02420(18) -.00141(15)
C2 .0335(2) .0326(2) .0329(2) -.00331(18) .0297(2) -.00450(18)
C3 .0343(2) .0335(2) .0288(2) .00331(18) .0279(2) .00090(18)
C4 .0338(2) .0346(2) .0340(2) .00502(19) .0309(2) .00359(19)
C6 .0387(2) .0336(2) .0277(2) -.00261(19) .0292(2) -.00270(18)
C7 .0434(3) .0486(3) .0361(3) .0060(2) .0338(3) .0060(2)
C8 .0613(3) .0502(3) .0411(3) .0117(3) .0431(3) .0134(2)
C9 .0744(4) .0492(3) .0514(3) -.0061(3) .0558(3) .0029(3)
C10 .0580(3) .0466(3) .0460(3) -.0086(2) .0475(3) -.0050(2)
C11 .0404(3) .0353(2) .0324(2) -.0042(2) .0326(2) -.00441(19)
C12 .0322(2) .0336(2) .0354(2) .00140(19) .0310(2) -.00038(19)
C13 .0468(3) .0372(3) .0462(3) .0000(2) .0424(3) .0002(2)
C14 .0792(4) .0359(3) .0813(4) .0035(3) .0753(4) .0039(3)
C15 .0791(4) .0572(4) .0790(4) .0314(3) .0744(4) .0326(3)
C16 .0472(3) .0783(4) .0441(3) .0229(3) .0410(3) .0200(3)
C17 .0364(3) .0512(3) .0375(3) .0035(2) .0331(3) .0002(2)
C20 .0339(2) .0454(3) .0330(3) -.0064(2) .0288(2) -.0070(2)
C21 .0295(2) .0366(2) .0296(2) .0014(2) .0248(2) .0017(2)
C24 .0546(3) .0633(3) .0663(4) .0043(3) .0556(3) .0085(3)
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 'Waasmaier & Kirfel (1995)'
'H ' 'H ' .0000 .0000 'Waasmaier & Kirfel (1995)'
'N ' 'N ' .0061 .0033 'Waasmaier & Kirfel (1995)'
'O ' 'O ' .0106 .0060 'Waasmaier & Kirfel (1995)'
'S ' 'S ' .1246 .1234 'Waasmaier & Kirfel (1995)'
loop_
_diffrn_radiation_wavelength
.71073
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 S1 C11 103.89(2)
C21 O23 C24 116.62(4)
C4 N5 C6 123.77(4)
C4 N5 C20 116.07(3)
C6 N5 C20 120.07(3)
S1 C2 C3 111.33(3)
S1 C2 C12 109.42(3)
C3 C2 C12 112.89(3)
O18 C3 C2 110.64(3)
O18 C3 C4 107.82(3)
C2 C3 C4 112.63(3)
O19 C4 N5 121.50(4)
O19 C4 C3 119.33(4)
N5 C4 C3 119.11(3)
N5 C6 C7 119.01(4)
N5 C6 C11 120.63(4)
C7 C6 C11 120.34(4)
C6 C7 C8 120.15(4)
C7 C8 C9 119.88(5)
C8 C9 C10 120.35(4)
C9 C10 C11 120.56(4)
S1 C11 C6 122.47(3)
S1 C11 C10 118.47(3)
C6 C11 C10 118.67(4)
C2 C12 C13 122.66(4)
C2 C12 C17 118.80(4)
C13 C12 C17 118.53(4)
C12 C13 C14 120.30(4)
C13 C14 C15 120.39(5)
C14 C15 C16 119.95(5)
C15 C16 C17 120.17(5)
C12 C17 C16 120.64(5)
N5 C20 C21 111.51(3)
O22 C21 O23 125.12(4)
O22 C21 C20 125.28(4)
O23 C21 C20 109.57(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C2 . . 1.8350(4) ?
S1 C11 . . 1.7738(4) ?
O18 C3 . . 1.4184(4) ?
O19 C4 . . 1.2304(5) ?
O22 C21 . . 1.1908(5) ?
O23 C21 . . 1.3243(5) ?
O23 C24 . . 1.4482(5) ?
N5 C4 . . 1.3457(5) ?
N5 C6 . . 1.4339(5) ?
N5 C20 . . 1.4594(5) ?
C2 C3 . . 1.5450(5) ?
C2 C12 . . 1.5098(6) ?
C3 C4 . . 1.5176(6) ?
C6 C7 . . 1.3870(6) ?
C6 C11 . . 1.3929(5) ?
C7 C8 . . 1.3847(7) ?
C8 C9 . . 1.3809(7) ?
C9 C10 . . 1.3761(7) ?
C10 C11 . . 1.4013(6) ?
C12 C13 . . 1.3896(6) ?
C12 C17 . . 1.3908(6) ?
C13 C14 . . 1.3887(6) ?
C14 C15 . . 1.3739(7) ?
C15 C16 . . 1.3718(8) ?
C16 C17 . . 1.3867(7) ?
C20 C21 . . 1.5121(6) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139064730