##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# 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     'from SHELXL-97 with Word-Perfect Macro PRPKAPPA'
_journal_date_recd_electronic     2004-05-17
_journal_date_accepted     2004-05-19
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2004
_journal_volume     60
_journal_issue      6
_journal_page_first     o1057
_journal_page_last     o1059
_journal_paper_category     EO
_publ_contact_author_name
;
Dr Christopher Glidewell
;
_publ_contact_author_address
;
University of St Andrews,
Fife KY16 9ST, UK
;
_publ_contact_author_email     cg@st-andrews.ac.uk
_publ_contact_author_fax     '+1334-463808'
_publ_contact_author_phone     '+1334-463839'
_publ_section_title
;
rac-5-Acetyl-6-(4-nitrophenyl)-6,7-dihydro-5H-1,3-dioxolo[4,5-g]quinoline-8-one:
chains of rings built from C---H...O and C---H...π(arene) hydrogen bonds
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Low, John N.' .
;
Department of Chemistry
University of Aberdeen
Meston Walk
Old Aberdeen AB24 3UE
Scotland
;
    'Cobo, Justo' .
;
Departamento de Química Inorgánica y Orgánica
Universidad de Jaén
23071 Jaén
Spain
;
    'Ortíz, Angy' .
;
Grupo de Investigación de Compuestos Heterociclícos
Departamento de Química
Universidad de Valle
AA 25360 Colombia
;
    'Cuervo, Paola' .
;
Grupo de Investigación de Compuestos Heterociclícos
Departamento de Química
Universidad de Valle
AA 25360 Colombia
;
    'Abonia, Rodrigo' .
;
Grupo de Investigación de Compuestos Heterociclícos
Departamento de Química
Universidad de Valle
AA 25360 Colombia
;
    'Glidewell, Christopher' .
;
School of Chemistry
University of St Andrews
Fife KY16 9ST
Scotland
;
data_I
_chemical_name_systematic
;
rac-5-Acetyl-6-(4-nitrophenyl)-6,7-dihydro-5H-1,3-dioxolo[4,5-g]quinoline-8-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C18 H14 N2 O6'
_chemical_formula_sum     'C18 H14 N2 O6'
_chemical_formula_iupac     'C18 H14 N2 O6'
_chemical_formula_weight     354.31
_chemical_melting_point     ?
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P n a 21'
_symmetry_space_group_name_Hall     'P 2c -2n'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, z+1/2'
    '-x+1/2, y+1/2, z+1/2'
    'x+1/2, -y+1/2, z'
_cell_length_a     6.5253(2)
_cell_length_b     21.4286(5)
_cell_length_c     10.8198(9)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     1512.91(14)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     1952
_cell_measurement_theta_min     3.26
_cell_measurement_theta_max     27.14
_cell_measurement_temperature     120(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.10
_exptl_crystal_size_min     0.09
_exptl_crystal_density_diffrn     1.556
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     736
_exptl_absorpt_coefficient_mu     0.119
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SORTAV; Blessing, 1995, 1997)'
_exptl_absorpt_correction_T_min     0.956
_exptl_absorpt_correction_T_max     0.989
_exptl_special_details
;
;
_diffrn_ambient_temperature     120(2)
_diffrn_radiation_type     'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'rotating anode'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Nonius KappaCCD'
_diffrn_measurement_method     'φ scans, and ω scans with κ offsets'
_diffrn_reflns_number     15335
_diffrn_reflns_av_R_equivalents     0.0818
_diffrn_reflns_av_sigmaI/netI     0.0712
_diffrn_reflns_theta_min     3.26
_diffrn_reflns_theta_max     27.14
_diffrn_reflns_theta_full     27.14
_diffrn_measured_fraction_theta_max     0.996
_diffrn_measured_fraction_theta_full     0.996
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_h_max     7
_diffrn_reflns_limit_k_min     -27
_diffrn_reflns_limit_k_max     27
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     13
_diffrn_standards_decay_%     negligible
_reflns_number_total     1762
_reflns_number_gt     1360
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0697
_refine_ls_R_factor_gt     0.0415
_refine_ls_wR_factor_gt     0.0783
_refine_ls_wR_factor_ref     0.0865
_refine_ls_goodness_of_fit_ref     1.058
_refine_ls_restrained_S_all     1.058
_refine_ls_number_reflns     1762
_refine_ls_number_parameters     237
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
          'w = 1/[σ²(Fo²)+(0.0457P)²+0.0405P] where P = (Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.207
_refine_diff_density_min     -0.218
_refine_ls_extinction_method     SHELXL97
_refine_ls_extinction_coef     0.0110(18)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'KappaCCD Server Software (Nonius, 1997)'
_computing_cell_refinement     'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction     'DENZO-SMN'
_computing_structure_solution
                         'OSCAIL (McArdle, 2003) and SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'OSCAIL and SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'PLATON (Spek, 2003)'
_computing_publication_material     'SHELXL97 and PRPKAPPA (Ferguson, 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 0.5209(4) 0.45991(10) 0.5921(2) 0.0450(6) Uani d . 1 . . O
    C2 0.6518(5) 0.49285(15) 0.5084(4) 0.0429(8) Uani d . 1 . . C
    O3 0.5919(3) 0.55753(10) 0.5100(2) 0.0383(6) Uani d . 1 . . O
    C3A 0.4110(4) 0.55944(14) 0.5736(3) 0.0278(7) Uani d . 1 . . C
    C4 0.2903(4) 0.61069(13) 0.5940(3) 0.0265(6) Uani d . 1 . . C
    C4A 0.1148(4) 0.60062(12) 0.6658(2) 0.0237(6) Uani d . 1 . . C
    N5 -0.0191(3) 0.65140(12) 0.6922(2) 0.0262(5) Uani d . 1 . . N
    C51 -0.1005(4) 0.69175(13) 0.6047(3) 0.0291(7) Uani d . 1 . . C
    O51 -0.2149(3) 0.73380(10) 0.63757(19) 0.0426(6) Uani d . 1 . . O
    C52 -0.0541(5) 0.68171(14) 0.4710(3) 0.0313(7) Uani d . 1 . . C
    C6 -0.1136(4) 0.65011(13) 0.8158(3) 0.0278(6) Uani d . 1 . . C
    C61 0.0432(4) 0.65684(13) 0.9186(3) 0.0249(6) Uani d . 1 . . C
    C62 0.2377(4) 0.68212(13) 0.8979(3) 0.0268(6) Uani d . 1 . . C
    C63 0.3740(4) 0.69024(13) 0.9951(3) 0.0273(6) Uani d . 1 . . C
    C64 0.3144(4) 0.67328(12) 1.1127(2) 0.0246(6) Uani d . 1 . . C
    N64 0.4578(4) 0.68102(11) 1.2154(2) 0.0298(6) Uani d . 1 . . N
    O41 0.3963(3) 0.67045(11) 1.3207(2) 0.0451(6) Uani d . 1 . . O
    O42 0.6331(3) 0.69795(11) 1.1920(2) 0.0410(6) Uani d . 1 . . O
    C65 0.1243(4) 0.64875(13) 1.1358(3) 0.0292(7) Uani d . 1 . . C
    C66 -0.0106(4) 0.64056(13) 1.0388(3) 0.0306(7) Uani d . 1 . . C
    C7 -0.2388(4) 0.59007(15) 0.8248(3) 0.0358(7) Uani d . 1 . . C
    C8 -0.1070(5) 0.53365(14) 0.8006(3) 0.0347(7) Uani d . 1 . . C
    O8 -0.1483(4) 0.48271(11) 0.8451(2) 0.0578(8) Uani d . 1 . . O
    C8A 0.0733(4) 0.54239(13) 0.7194(3) 0.0278(6) Uani d . 1 . . C
    C9 0.2061(5) 0.49165(13) 0.6998(3) 0.0327(7) Uani d . 1 . . C
    C9A 0.3695(4) 0.50171(13) 0.6255(3) 0.0307(7) Uani d . 1 . . C
    H2A 0.6375 0.4756 0.4239 0.051 Uiso calc R 1 . . H
    H2B 0.7966 0.4886 0.5344 0.051 Uiso calc R 1 . . H
    H4 0.3235 0.6506 0.5614 0.032 Uiso calc R 1 . . H
    H52A -0.1760 0.6913 0.4216 0.047 Uiso calc R 1 . . H
    H52B -0.0145 0.6381 0.4577 0.047 Uiso calc R 1 . . H
    H52C 0.0586 0.7092 0.4460 0.047 Uiso calc R 1 . . H
    H6 -0.2106 0.6861 0.8215 0.033 Uiso calc R 1 . . H
    H62 0.2769 0.6939 0.8166 0.032 Uiso calc R 1 . . H
    H63 0.5064 0.7072 0.9807 0.033 Uiso calc R 1 . . H
    H65 0.0859 0.6375 1.2175 0.035 Uiso calc R 1 . . H
    H66 -0.1425 0.6235 1.0544 0.037 Uiso calc R 1 . . H
    H7A -0.2999 0.5868 0.9083 0.043 Uiso calc R 1 . . H
    H7B -0.3519 0.5914 0.7639 0.043 Uiso calc R 1 . . H
    H9 0.1822 0.4522 0.7369 0.039 Uiso calc R 1 . . H
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 . 1.431(4) y
    C2 O3 . 1.440(4) y
    C2 H2A . 0.99 no
    C2 H2B . 0.99 no
    O3 C3A . 1.367(3) y
    C3A C4 . 1.369(4) y
    C4 C4A . 1.400(4) y
    C4 H4 . 0.95 no
    C4A N5 . 1.425(3) y
    N5 C6 . 1.472(4) y
    C51 C52 . 1.493(4) no
    C52 H52A . 0.98 no
    C52 H52B . 0.98 no
    C52 H52C . 0.98 no
    C6 C61 . 1.519(4) no
    C6 C7 . 1.527(4) y
    C6 H6 . 1.00 no
    C7 C8 . 1.506(4) y
    C7 H7A . 0.99 no
    C7 H7B . 0.99 no
    C8 C8A . 1.480(4) y
    C8A C9 . 1.407(4) y
    C9 C9A . 1.352(4) y
    C9 H9 . 0.95 no
    C9A O1 . 1.381(3) y
    C3A C9A . 1.385(4) y
    C4A C8A . 1.403(4) y
    N5 C51 . 1.388(4) y
    C51 O51 . 1.223(3) y
    C8 O8 . 1.223(4) y
    C61 C66 . 1.391(4) no
    C61 C62 . 1.398(4) no
    C62 C63 . 1.388(4) no
    C62 H62 . 0.95 no
    C63 C64 . 1.379(4) no
    C63 H63 . 0.95 no
    C64 C65 . 1.370(4) no
    C64 N64 . 1.463(4) no
    N64 O42 . 1.226(3) no
    N64 O41 . 1.229(3) no
    C65 C66 . 1.381(4) no
    C65 H65 . 0.95 no
    C66 H66 . 0.95 no
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
    C9A O1 C2 . . 105.8(2) no
    O1 C2 O3 . . 107.8(2) no
    O1 C2 H2A . . 110.2 no
    O3 C2 H2A . . 110.2 no
    O1 C2 H2B . . 110.2 no
    O3 C2 H2B . . 110.2 no
    H2A C2 H2B . . 108.5 no
    C3A O3 C2 . . 105.6(2) no
    O3 C3A C4 . . 127.0(3) no
    O3 C3A C9A . . 110.2(2) no
    C4 C3A C9A . . 122.6(3) no
    C3A C4 C4A . . 115.8(3) no
    C3A C4 H4 . . 122.1 no
    C4A C4 H4 . . 122.1 no
    C4 C4A C8A . . 121.6(2) no
    C4 C4A N5 . . 119.7(2) no
    C8A C4A N5 . . 118.5(2) no
    C51 N5 C4A . . 125.0(2) yes
    C51 N5 C6 . . 118.1(2) yes
    C4A N5 C6 . . 115.1(2) yes
    O51 C51 N5 . . 119.6(3) no
    O51 C51 C52 . . 120.8(3) no
    N5 C51 C52 . . 119.6(2) no
    C51 C52 H52A . . 109.5 no
    C51 C52 H52B . . 109.5 no
    H52A C52 H52B . . 109.5 no
    C51 C52 H52C . . 109.5 no
    H52A C52 H52C . . 109.5 no
    H52B C52 H52C . . 109.5 no
    N5 C6 C61 . . 112.4(2) no
    N5 C6 C7 . . 107.3(2) no
    C61 C6 C7 . . 113.2(2) no
    N5 C6 H6 . . 107.9 no
    C61 C6 H6 . . 107.9 no
    C7 C6 H6 . . 107.9 no
    C66 C61 C62 . . 118.4(3) no
    C66 C61 C6 . . 119.4(2) no
    C62 C61 C6 . . 122.1(2) no
    C63 C62 C61 . . 120.6(3) no
    C63 C62 H62 . . 119.7 no
    C61 C62 H62 . . 119.7 no
    C64 C63 C62 . . 119.0(3) no
    C64 C63 H63 . . 120.5 no
    C62 C63 H63 . . 120.5 no
    C65 C64 C63 . . 121.7(3) no
    C65 C64 N64 . . 118.9(2) no
    C63 C64 N64 . . 119.4(2) no
    O42 N64 O41 . . 123.4(3) no
    O42 N64 C64 . . 118.3(2) no
    O41 N64 C64 . . 118.3(2) no
    C64 C65 C66 . . 119.1(2) no
    C64 C65 H65 . . 120.4 no
    C66 C65 H65 . . 120.4 no
    C65 C66 C61 . . 121.2(3) no
    C65 C66 H66 . . 119.4 no
    C61 C66 H66 . . 119.4 no
    C8 C7 C6 . . 111.1(2) no
    C8 C7 H7A . . 109.4 no
    C6 C7 H7A . . 109.4 no
    C8 C7 H7B . . 109.4 no
    C6 C7 H7B . . 109.4 no
    H7A C7 H7B . . 108.0 no
    O8 C8 C8A . . 121.4(3) no
    O8 C8 C7 . . 121.5(3) no
    C8A C8 C7 . . 117.1(2) no
    C4A C8A C9 . . 120.4(3) no
    C4A C8A C8 . . 120.8(3) no
    C9 C8A C8 . . 118.8(3) no
    C9A C9 C8A . . 116.9(3) no
    C9A C9 H9 . . 121.6 no
    C8A C9 H9 . . 121.6 no
    C9 C9A O1 . . 128.0(3) no
    C9 C9A C3A . . 122.5(3) no
    O1 C9A C3A . . 109.5(3) no
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
    C9A O1 C2 O3 . . . . 9.3(3) no
    O1 C2 O3 C3A . . . . -10.7(3) no
    C2 O3 C3A C4 . . . . -176.6(3) no
    C2 O3 C3A C9A . . . . 8.0(3) no
    O3 C3A C4 C4A . . . . -178.0(3) no
    C9A C3A C4 C4A . . . . -3.1(4) no
    C3A C4 C4A C8A . . . . 3.8(4) no
    C3A C4 C4A N5 . . . . 179.6(2) no
    C4 C4A N5 C51 . . . . 51.2(4) no
    C8A C4A N5 C51 . . . . -132.8(3) no
    C4 C4A N5 C6 . . . . -144.3(3) no
    C8A C4A N5 C6 . . . . 31.7(3) no
    C4A N5 C51 O51 . . . . 179.7(3) no
    C6 N5 C51 O51 . . . . 15.7(4) no
    C4A N5 C51 C52 . . . . 2.2(4) no
    C6 N5 C51 C52 . . . . -161.9(3) no
    C51 N5 C6 C61 . . . . -129.5(3) no
    C4A N5 C6 C61 . . . . 64.8(3) no
    C51 N5 C6 C7 . . . . 105.4(3) no
    C4A N5 C6 C7 . . . . -60.2(3) no
    N5 C6 C61 C66 . . . . -163.4(2) no
    C7 C6 C61 C66 . . . . -41.6(4) no
    N5 C6 C61 C62 . . . . 20.1(4) no
    C7 C6 C61 C62 . . . . 141.9(3) no
    C66 C61 C62 C63 . . . . 0.5(4) no
    C6 C61 C62 C63 . . . . 177.0(3) no
    C61 C62 C63 C64 . . . . -0.3(4) no
    C62 C63 C64 C65 . . . . -0.1(4) no
    C62 C63 C64 N64 . . . . 179.3(2) no
    C65 C64 N64 O42 . . . . 173.8(2) no
    C63 C64 N64 O42 . . . . -5.6(4) no
    C65 C64 N64 O41 . . . . -6.4(4) no
    C63 C64 N64 O41 . . . . 174.2(3) no
    C63 C64 C65 C66 . . . . 0.3(4) no
    N64 C64 C65 C66 . . . . -179.1(2) no
    C64 C65 C66 C61 . . . . -0.1(4) no
    C62 C61 C66 C65 . . . . -0.3(4) no
    C6 C61 C66 C65 . . . . -176.9(3) no
    N5 C6 C7 C8 . . . . 56.7(3) no
    C61 C6 C7 C8 . . . . -67.9(3) no
    C6 C7 C8 O8 . . . . 152.7(3) no
    C6 C7 C8 C8A . . . . -28.0(4) no
    C4 C4A C8A C9 . . . . -1.5(4) no
    N5 C4A C8A C9 . . . . -177.4(3) no
    C4 C4A C8A C8 . . . . 176.6(3) no
    N5 C4A C8A C8 . . . . 0.7(4) no
    O8 C8 C8A C4A . . . . 177.9(3) no
    C7 C8 C8A C4A . . . . -1.5(4) no
    O8 C8 C8A C9 . . . . -3.9(4) no
    C7 C8 C8A C9 . . . . 176.7(3) no
    C4A C8A C9 C9A . . . . -1.5(4) no
    C8 C8A C9 C9A . . . . -179.7(3) no
    C8A C9 C9A O1 . . . . 179.9(3) no
    C8A C9 C9A C3A . . . . 2.2(4) no
    C2 O1 C9A C9 . . . . 177.5(3) no
    C2 O1 C9A C3A . . . . -4.5(3) no
    O3 C3A C9A C9 . . . . 175.8(3) no
    C4 C3A C9A C9 . . . . 0.2(4) no
    O3 C3A C9A O1 . . . . -2.3(3) no
    C4 C3A C9A O1 . . . . -177.9(3) no
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
    _geom_hbond_publ_flag
    C62 H62 O51 4_565 0.95 2.48 3.358(4) 153 y
    C63 H63 Cg1 4_565 0.95 2.98 3.693(3) 132 y
