##############################################################################
###                                                                        ###
###           Full Paper (Acta Crystallographica Section C)                ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section C. It conforms to the editorial and technical    #
# requirements of Notes for Authors for Section C, 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     'WinGX routine CIF_UPDATE'
_audit_conform_dict_name     cif_core.dic
_audit_conform_dict_version     2.1
_journal_date_recd_electronic     2001-03-16
_journal_date_accepted     2001-04-10
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2001
_journal_volume     57
_journal_issue      7
_journal_page_first     848
_journal_page_last     850
_journal_paper_category     FO
_publ_contact_author_name     'Vega, Daniel'
_publ_contact_author_address
;
 Departamento de Fisica,
 Comision Nacional de Energia Atomica.
 Av. del Libertador 8250,
 1429 Buenos Aires, Argentina
;
_publ_contact_author_email     vega@cnea.gov.ar
_publ_contact_author_fax     '54-11-4755_8710/4754_7121'
_publ_contact_author_phone     '54-11-4754_7107'
_publ_section_title
;
11-Chloro-8,12b-dihydro-2,8-dimethyl-12b-phenyl-4H-[1,3]oxazino
[3,2-d][1,4]benzodiazepine-4,7(6H)-dione (Ketazolam)
;
loop_
    _publ_author_name
    _publ_author_address
    'Vega, Daniel'
;
Departamento de  Física,
Comisión Nacional de Energía Atómica,
Buenos Aires, Argentina
;
    "Fernández, Daniel"
;
Escuela de Ciencia y Tecnología,
Universidad Nacional de General San Martín,
Buenos Aires, Argentina
;
    "Echeverría, Gustavo"
;
LANADI, Departamento de Física,
Universidad Nacional de La Plata,
La Plata, Argentina
;
data_I
_audit_creation_method     'WinGX routine CIF_UPDATE'
_chemical_formula_moiety     'C20 H17 Cl N2 O3'
_chemical_formula_sum     'C20 H17 Cl N2 O3'
_chemical_formula_weight     368.81
_chemical_melting_point     455
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     ' P 21 /n'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     8.6326(9)
_cell_length_b     13.1190(10)
_cell_length_c     15.505(4)
_cell_angle_alpha     90
_cell_angle_beta     96.190(10)
_cell_angle_gamma     90
_cell_volume     1745.7(5)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     25
_cell_measurement_theta_min     10
_cell_measurement_theta_max     20
_cell_measurement_temperature     293(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     colourless
_exptl_crystal_size_max      .36
_exptl_crystal_size_mid      .2
_exptl_crystal_size_min      .14
_exptl_crystal_density_diffrn     1.403
_exptl_crystal_density_meas     'not measured'
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     768
_exptl_absorpt_coefficient_mu      .242
_exptl_absorpt_correction_type     numerical
_exptl_absorpt_process_details     'integration (Sheldrick, 1976)'
_exptl_absorpt_correction_T_min      .91
_exptl_absorpt_correction_T_max      .94
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength      .71073
_diffrn_measurement_device_type     CAD4
_diffrn_measurement_method     ω--2θ
_diffrn_reflns_number     3493
_diffrn_reflns_av_R_equivalents      .031
_diffrn_reflns_theta_min     2.04
_diffrn_reflns_theta_max     25
_diffrn_reflns_theta_full     25
_diffrn_measured_fraction_theta_max     1
_diffrn_measured_fraction_theta_full     1
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -1
_diffrn_reflns_limit_k_max     15
_diffrn_reflns_limit_l_min     0
_diffrn_reflns_limit_l_max     18
_diffrn_standards_number     2
_diffrn_standards_interval_count     98
_diffrn_standards_decay_%     <2
_reflns_number_total     3071
_reflns_number_gt     1551
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_gt      .046
_refine_ls_wR_factor_ref      .1317
_refine_ls_goodness_of_fit_ref     1.071
_refine_ls_restrained_S_all     1.071
_refine_ls_number_reflns     3071
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0369P)²+0.9696P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max     <0.001
_refine_diff_density_max      .216
_refine_diff_density_min      -.241
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     none
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 0 0 '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'
    N N  .0061  .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    O O  .0106  .006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'CAD-4/PC (Enraf Nonius, 1993)'
_computing_cell_refinement     'CAD-4/PC'
_computing_data_reduction     'MolEN (Fair, 1990)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material
;
PARST (Nardelli, 1995), CSD (Allen et al., 1983) and
        WinGX (Farrugia, 1999)
;
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_disorder_assembly
    _atom_site_disorder_group
    _atom_site_type_symbol
    O1  .0413(2)  .31121(17)  -.17074(14)  .0406(6) Uani d . 1 . . O
    O4  -.0803(3)  .0213(2)  -.14088(19)  .0619(8) Uani d . 1 . . O
    O7  .3936(3)  -.0127(2)  -.09127(18)  .0631(8) Uani d . 1 . . O
    N5  .0977(3)  .1480(2)  -.11214(17)  .0392(7) Uani d . 1 . . N
    N8  .4486(3)  .1530(2)  -.06120(18)  .0443(7) Uani d . 1 . . N
    C2  -.0752(4)  .2699(3)  -.2273(2)  .0430(9) Uani d . 1 . . C
    C3  -.1081(4)  .1718(3)  -.2243(2)  .0461(9) Uani d . 1 . . C
    H3  -.1826  .1445  -.2657  .055 Uiso calc R 1 . . H
    C4  -.0314(4)  .1053(3)  -.1583(2)  .0458(9) Uani d . 1 . . C
    C6  .1877(4)  .0886(3)  -.0445(2)  .0457(9) Uani d . 1 . . C
    H6B  .1368  .0236  -.0378  .055 Uiso calc R 1 . . H
    H6A  .1917  .1248  .0103  .055 Uiso calc R 1 . . H
    C7  .3524(4)  .0705(3)  -.0671(2)  .0467(9) Uani d . 1 . . C
    C8  .6064(4)  .1430(4)  -.0865(3)  .0686(13) Uani d . 1 . . C
    H8C  .6224  .0744  -.1051  .103 Uiso calc R 1 . . H
    H8B  .6808  .1588  -.0378  .103 Uiso calc R 1 . . H
    H8A  .6194  .1892  -.1332  .103 Uiso calc R 1 . . H
    C9  .4007(4)  .2487(3)  -.0313(2)  .0403(8) Uani d . 1 . . C
    C10  .4911(4)  .3002(3)  .0345(2)  .0514(10) Uani d . 1 . . C
    H10  .5854  .2722  .0578  .062 Uiso calc R 1 . . H
    C11  .4437(4)  .3913(3)  .0655(2)  .0543(11) Uani d . 1 . . C
    H11  .5062  .4258  .1085  .065 Uiso calc R 1 . . H
    C12  .3031(4)  .4311(3)  .0324(2)  .0473(9) Uani d . 1 . . C
    C13  .2120(4)  .3836(3)  -.0330(2)  .0407(9) Uani d . 1 . . C
    H13  .1169  .4121  -.0544  .049 Uiso calc R 1 . . H
    C14  .2610(4)  .2926(2)  -.0677(2)  .0349(8) Uani d . 1 . . C
    C15  .1648(3)  .2412(3)  -.1429(2)  .0362(8) Uani d . 1 . . C
    C16  .2586(3)  .2249(3)  -.2203(2)  .0347(8) Uani d . 1 . . C
    C17  .2796(4)  .1313(3)  -.2568(2)  .0464(9) Uani d . 1 . . C
    H17  .2349  .0737  -.2346  .056 Uiso calc R 1 . . H
    C18  .3667(4)  .1218(3)  -.3261(3)  .0620(12) Uani d . 1 . . C
    H18  .3821  .0579  -.3497  .074 Uiso calc R 1 . . H
    C19  .4300(5)  .2061(4)  -.3601(3)  .0654(12) Uani d . 1 . . C
    H19  .488  .1996  -.407  .078 Uiso calc R 1 . . H
    C20  .4083(4)  .2997(3)  -.3255(3)  .0617(12) Uani d . 1 . . C
    H20  .4509  .3571  -.349  .074 Uiso calc R 1 . . H
    C21  .3234(4)  .3092(3)  -.2558(2)  .0507(10) Uani d . 1 . . C
    H21  .3093  .3734  -.2323  .061 Uiso calc R 1 . . H
    C22  -.1521(4)  .3485(3)  -.2865(2)  .0597(11) Uani d . 1 . . C
    H22C  -.2339  .3174  -.3244  .09 Uiso calc R 1 . . H
    H22B  -.0767  .378  -.3203  .09 Uiso calc R 1 . . H
    H22A  -.1951  .4008  -.2529  .09 Uiso calc R 1 . . H
    Cl1  .23773(14)  .54380(9)  .07470(7)  .0750(4) Uani d . 1 . . Cl
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
    O1 C2 . 1.372(4) ?
    O1 C15 . 1.438(4) Y
    O4 C4 . 1.221(4) Y
    O7 C7 . 1.219(4) Y
    N5 C4 . 1.377(4) Y
    N5 C15 . 1.455(4) Y
    N5 C6 . 1.462(4) Y
    N8 C7 . 1.361(4) Y
    N8 C9 . 1.416(4) Y
    N8 C8 . 1.463(4) ?
    C2 C3 . 1.320(5) ?
    C2 C22 . 1.488(5) ?
    C3 C4 . 1.449(5) ?
    C6 C7 . 1.519(5) Y
    C9 C10 . 1.390(5) ?
    C9 C14 . 1.399(4) ?
    C10 C11 . 1.367(5) ?
    C11 C12 . 1.369(5) ?
    C12 C13 . 1.364(5) ?
    C12 Cl1 . 1.736(4) Y
    C13 C14 . 1.395(4) ?
    C14 C15 . 1.515(4) Y
    C15 C16 . 1.534(4) Y
    C16 C17 . 1.372(5) ?
    C16 C21 . 1.381(5) ?
    C17 C18 . 1.382(5) ?
    C18 C19 . 1.365(6) ?
    C19 C20 . 1.360(5) ?
    C20 C21 . 1.375(5) ?
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_3
    _geom_angle
    _geom_angle_publ_flag
    C2 O1 C15 . . 114.1(3) ?
    C4 N5 C15 . . 120.0(3) Y
    C4 N5 C6 . . 119.7(3) Y
    C15 N5 C6 . . 118.9(3) Y
    C7 N8 C9 . . 122.0(3) Y
    C7 N8 C8 . . 119.4(3) Y
    C9 N8 C8 . . 118.7(3) Y
    C3 C2 O1 . . 120.5(3) ?
    C3 C2 C22 . . 127.9(3) ?
    O1 C2 C22 . . 111.6(3) ?
    C2 C3 C4 . . 121.9(3) ?
    O4 C4 N5 . . 122.1(4) ?
    O4 C4 C3 . . 123.8(3) ?
    N5 C4 C3 . . 113.9(3) ?
    N5 C6 C7 . . 110.9(3) Y
    O7 C7 N8 . . 122.4(3) ?
    O7 C7 C6 . . 121.5(4) ?
    N8 C7 C6 . . 116.1(3) ?
    C10 C9 C14 . . 119.2(3) ?
    C10 C9 N8 . . 120.7(3) ?
    C14 C9 N8 . . 120.1(3) ?
    C11 C10 C9 . . 121.1(4) ?
    C10 C11 C12 . . 119.3(4) ?
    C13 C12 C11 . . 121.4(3) ?
    C13 C12 Cl1 . . 119.0(3) ?
    C11 C12 Cl1 . . 119.7(3) ?
    C12 C13 C14 . . 120.2(3) ?
    C13 C14 C9 . . 118.7(3) ?
    C13 C14 C15 . . 121.0(3) ?
    C9 C14 C15 . . 120.3(3) ?
    O1 C15 N5 . . 109.1(2) Y
    O1 C15 C14 . . 105.9(3) Y
    N5 C15 C14 . . 109.0(3) Y
    O1 C15 C16 . . 107.0(2) Y
    N5 C15 C16 . . 113.7(3) Y
    C14 C15 C16 . . 111.8(2) Y
    C17 C16 C21 . . 118.4(3) ?
    C17 C16 C15 . . 123.5(3) ?
    C21 C16 C15 . . 118.1(3) ?
    C16 C17 C18 . . 120.5(4) ?
    C19 C18 C17 . . 120.1(4) ?
    C20 C19 C18 . . 120.1(4) ?
    C19 C20 C21 . . 120.0(4) ?
    C20 C21 C16 . . 120.9(4) ?
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C15 O1 C2 C3 . . . . 29.4(4) ?
    C15 O1 C2 C22 . . . . -151.3(3) ?
    O1 C2 C3 C4 . . . . 4.3(5) ?
    C22 C2 C3 C4 . . . . -174.9(3) ?
    C15 N5 C4 O4 . . . . 171.1(3) ?
    C6 N5 C4 O4 . . . . 5.0(5) ?
    C15 N5 C4 C3 . . . . -12.9(4) ?
    C6 N5 C4 C3 . . . . -179.0(3) ?
    C2 C3 C4 O4 . . . . 163.1(4) ?
    C2 C3 C4 N5 . . . . -12.8(5) ?
    C4 N5 C6 C7 . . . . 116.7(3) ?
    C15 N5 C6 C7 . . . . -49.4(4) ?
    C9 N8 C7 O7 . . . . -178.7(3) ?
    C8 N8 C7 O7 . . . . 1.4(5) ?
    C9 N8 C7 C6 . . . . 3.3(5) ?
    C8 N8 C7 C6 . . . . -176.7(3) ?
    N5 C6 C7 O7 . . . . -106.0(4) ?
    N5 C6 C7 N8 . . . . 72.0(4) ?
    C7 N8 C9 C10 . . . . 128.6(4) ?
    C8 N8 C9 C10 . . . . -51.5(5) ?
    C7 N8 C9 C14 . . . . -51.2(4) ?
    C8 N8 C9 C14 . . . . 128.7(3) ?
    C14 C9 C10 C11 . . . . 1.7(5) ?
    N8 C9 C10 C11 . . . . -178.1(3) ?
    C9 C10 C11 C12 . . . . 1.5(5) ?
    C10 C11 C12 C13 . . . . -2.4(5) ?
    C10 C11 C12 Cl1 . . . . 177.1(3) ?
    C11 C12 C13 C14 . . . .  .0(5) ?
    Cl1 C12 C13 C14 . . . . -179.5(2) ?
    C12 C13 C14 C9 . . . . 3.2(5) ?
    C12 C13 C14 C15 . . . . -177.3(3) ?
    C10 C9 C14 C13 . . . . -4.0(5) ?
    N8 C9 C14 C13 . . . . 175.8(3) ?
    C10 C9 C14 C15 . . . . 176.5(3) ?
    N8 C9 C14 C15 . . . . -3.7(4) ?
    C2 O1 C15 N5 . . . . -50.8(3) ?
    C2 O1 C15 C14 . . . . -168.0(2) ?
    C2 O1 C15 C16 . . . . 72.6(3) ?
    C4 N5 C15 O1 . . . . 43.7(4) ?
    C6 N5 C15 O1 . . . . -150.2(3) ?
    C4 N5 C15 C14 . . . . 158.9(3) ?
    C6 N5 C15 C14 . . . . -35.0(4) ?
    C4 N5 C15 C16 . . . . -75.6(3) ?
    C6 N5 C15 C16 . . . . 90.6(3) ?
    C13 C14 C15 O1 . . . . 7.2(4) ?
    C9 C14 C15 O1 . . . . -173.3(3) ?
    C13 C14 C15 N5 . . . . -110.0(3) ?
    C9 C14 C15 N5 . . . . 69.5(4) ?
    C13 C14 C15 C16 . . . . 123.4(3) ?
    C9 C14 C15 C16 . . . . -57.1(4) ?
    O1 C15 C16 C17 . . . . -121.2(3) ?
    N5 C15 C16 C17 . . . .  -.8(4) ?
    C14 C15 C16 C17 . . . . 123.2(3) ?
    O1 C15 C16 C21 . . . . 57.8(4) ?
    N5 C15 C16 C21 . . . . 178.2(3) ?
    C14 C15 C16 C21 . . . . -57.8(4) ?
    C21 C16 C17 C18 . . . . 1.5(5) ?
    C15 C16 C17 C18 . . . . -179.5(3) ?
    C16 C17 C18 C19 . . . . -1.3(6) ?
    C17 C18 C19 C20 . . . .  .4(6) ?
    C18 C19 C20 C21 . . . .  .4(6) ?
    C19 C20 C21 C16 . . . .  -.3(6) ?
    C17 C16 C21 C20 . . . .  -.7(5) ?
    C15 C16 C21 C20 . . . . -179.8(3) ?
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
    C6 H6B O4 .  .97 2.33 2.760(4) 106
    C8 H8C O7 .  .96 2.31 2.743(5) 106
    C13 H13 O1 .  .93 2.28 2.637(4) 102
    C17 H17 N5 .  .93 2.54 2.882(4) 102
    C20 H20 O4 2_554  .93 2.44 3.332(5) 161
    C22 H22A Cl1 3_565  .96 2.92 3.721(4) 142
    C22 H22B O7 2_554  .96 2.63 3.578(5) 171
