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###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
#                                                                            #
##############################################################################
                                             
data_global
_audit_creation_method     'maXus'
_journal_date_recd_electronic     2001-03-02
_journal_date_accepted     2001-03-19
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2001
_journal_volume     57
_journal_issue      4
_journal_page_first     o362
_journal_page_last     o363
_journal_paper_category     EO
_publ_contact_author_name     'Marcel Pierrot'
_publ_contact_author_address
;
LBS-UMR 6517
Faculte des Sciences et Techniques de Saint Jerome
Avenue Escadrille Normandie Niemen
13397 Marseille Cedex 20
France
;
_publ_contact_author_email     marcel.pierrot@lbs.u-3mrs.fr
_publ_contact_author_fax     '(33) 4 91 98 32 08'
_publ_contact_author_phone     '(33) 4 91 28 84 24'
_publ_section_title
;
Methyl (3-hydroxy-4-oxo-2-phenyl-1,5-benzothiazepin-5-yl)acetate
;
loop_
    _publ_author_name
    _publ_author_address
    'Zerzouf, A.'
;
Laboratoire de Chimie Organique Hétérocyclique
Faculté des Sciences
Université Mohamed V
Rabat
Morocco
;
    'El Meslouhi, H.'
;
Laboratoire de Chimie Organique Hétérocyclique
Faculté des Sciences
Université Mohamed V
Rabat
Morocco
;
    'Salem, M.'
;
Laboratoire de Chimie Organique Hétérocyclique
Faculté des Sciences
Université Mohamed V
Rabat
Morocco
;
    'Essassi, E. M.'
;
Laboratoire de Chimie Organique Hétérocyclique
Faculté des Sciences
Université Mohamed V
Rabat
Morocco
;
    'Pierrot, M.'
;
LBS-UMR 6517
Centre Scientifique Saint-Jérôme
13397 Marseille
Cedex 20
France
;
data_I
_chemical_name_systematic
;
 ?
;
_chemical_formula_moiety     'C18 H17 N O4 S'
_chemical_formula_sum     'C18 H17 N O4 S'
_chemical_formula_iupac     'C18 H17 N O4 S'
_chemical_formula_weight     343.401
_symmetry_cell_setting     'Monoclinic'
_symmetry_space_group_name_H-M     'P 21/c'
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'
_cell_length_a     13.6308(8)
_cell_length_b     15.1336(9)
_cell_length_c     16.1540(10)
_cell_angle_alpha     90.000(4)
_cell_angle_beta     151.086(3)
_cell_angle_gamma     90.000(10)
_cell_volume     1611.2(2)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     ' 10319'
_cell_measurement_theta_min     1
_cell_measurement_theta_max     26.40
_cell_measurement_temperature     298
_exptl_crystal_description     'Prism'
_exptl_crystal_colour     'Violet'
_exptl_crystal_size_max      .40
_exptl_crystal_size_mid      .30
_exptl_crystal_size_min      .20
_exptl_crystal_density_diffrn     1.416
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     720
_exptl_absorpt_coefficient_mu      .223
_exptl_absorpt_correction_type     none
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
?
;
_diffrn_radiation_type     MoK\a
loop_
    _diffrn_radiation_wavelength
     .71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_measurement_device     'KappaCCD'
_diffrn_measurement_method     φ
_diffrn_reflns_number     3302
_diffrn_reflns_av_R_equivalents      .046
_diffrn_reflns_theta_max     26.38
_diffrn_reflns_limit_h_min     -16
_diffrn_reflns_limit_h_max     16
_diffrn_reflns_limit_k_min     -18
_diffrn_reflns_limit_k_max     0
_diffrn_reflns_limit_l_min     -20
_diffrn_reflns_limit_l_max     16
_refine_special_details
;
Refinement on F²
;
_reflns_number_total     3156
_reflns_number_gt     2569
_reflns_threshold_expression     I>3σ(I)
_refine_ls_structure_factor_coef     F^2^
_refine_ls_matrix_type     full
_refine_ls_R_factor_all      .065
_refine_ls_R_factor_gt      .045
_refine_ls_wR_factor_all      .050
_refine_ls_wR_factor_ref      .048
_refine_ls_goodness_of_fit_all     1.510
_refine_ls_goodness_of_fit_ref     1.364
_refine_ls_number_reflns     2569
_refine_ls_number_parameters     217
_refine_ls_hydrogen_treatment     'noref'
_refine_ls_weighting_scheme     sigma
_refine_ls_weighting_details     'w = 1/[σ²(Fo²) + 0.03Fo²]'
_refine_ls_shift/su_max      .015
_refine_ls_shift/su_mean      .003
_refine_diff_density_max      .24
_refine_diff_density_min      -.30
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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)'
_computing_data_collection     'KappaCCD Reference Manual (Nonius, 1998)'
_computing_data_reduction     'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_structure_solution     'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement     'maXus (Mackay et al., 1999)'
_computing_molecular_graphics     'ORTEPII (Johnson, 1976)'
_computing_publication_material     'maXus'
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) Uij 1.00
    O18  -.01596(4)  .32975(2)  -.30649(4)  .08259(17) Uij 1.00
    O19  .29436(5)  .43419(2)  -.05234(4)  .09537(18) Uij 1.00
    O22  .67789(5)  .30762(2)  .20966(4)  .1256(2) Uij 1.00
    O23  .84397(5)  .43524(2)  .34720(4)  .1122(2) Uij 1.00
    N5  .41618(5)  .35605(2)  .14507(4)  .06322(19) Uij 1.00
    C2  -.07943(6)  .36288(3)  -.20796(5)  .0685(2) Uij 1.00
    C3  .07045(6)  .32628(3)  -.16231(5)  .0662(2) Uij 1.00
    C4  .26885(6)  .37712(3)  -.01795(5)  .0697(2) Uij 1.00
    C6  .39450(6)  .29014(3)  .19221(5)  .0694(2) Uij 1.00
    C7  .54413(7)  .22635(3)  .31138(6)  .0874(3) Uij 1.00
    C8  .53301(8)  .16520(3)  .36676(6)  .1089(3) Uij 1.00
    C9  .37105(9)  .16700(3)  .30134(7)  .1261(3) Uij 1.00
    C10  .21874(7)  .22834(3)  .17918(6)  .1045(3) Uij 1.00
    C11  .22828(6)  .29122(3)  .12267(5)  .0748(2) Uij 1.00
    C12  -.17461(6)  .44937(3)  -.30402(5)  .0689(2) Uij 1.00
    C13  -.08121(7)  .53048(3)  -.22189(6)  .0922(3) Uij 1.00
    C14  -.17508(9)  .60806(3)  -.31654(8)  .1468(3) Uij 1.00
    C15  -.36056(9)  .60541(4)  -.49229(8)  .1517(4) Uij 1.00
    C16  -.45319(7)  .52573(4)  -.57519(6)  .1052(3) Uij 1.00
    C17  -.36203(6)  .44790(3)  -.48200(6)  .0810(3) Uij 1.00
    C20  .61013(6)  .40095(3)  .27691(5)  .0745(2) Uij 1.00
    C21  .71033(6)  .37427(3)  .27050(5)  .0656(2) Uij 1.00
    C24  .95452(8)  .41952(3)  .35279(7)  .1240(3) Uij 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
_geom_special_details
;
All standard uncertainties (except dihedral angles between
l.s. planes) are estimated using the full covariance matrix.
The standard uncertainties in cell dimensions are are used in
calculating the standard uncertainties of bond distances,
angles and torsion angles. Angles between l.s. planes have
standard uncertainties calculated from atomic positional
standard uncertainties; the errors in cell dimensions are
not used in this case.
;
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_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_2
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    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) ?
