##############################################################################
###                                                                        ###
###           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     'from SHELXL-97 with Word-Perfect Macro PRPKAPPA'
_journal_date_recd_electronic     2001-11-27
_journal_date_accepted     2001-12-17
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2002
_journal_volume     58
_journal_issue      2
_journal_page_first     o125
_journal_page_last     o128
_journal_paper_category     FO
_publ_contact_author_name     'Dr John Nicolson Low'
_publ_contact_author_address
;
Department of Electronic Engineering and Physics
University of Dundee
Dundee DD1 4HN
Scotland
;
_publ_contact_author_email     'jnlow111@hotmail.com'
_publ_contact_author_fax     '+44 (0)1382 345415'
_publ_contact_author_phone     '+44 (0)1382 344562'
_publ_section_title
;
2-(4-Bromophenyl)-1,2-dihydropyrimido[1,2-a]benzimidazol-4(3H)-one and
4-(4-methylphenyl)-3,4-dihydropyrimido[1,2-a]benzimidazol-2(1H)-one
form hydrogen-bonded base-paired dimers
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Low, John Nicolson'
;
Postal address: Department of Electronic Engineering and Physics
University of Dundee
Dundee DD1 4HN
Scotland
;
;
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
;
    'Insuasty, Braulio' .
;
Grupo de Investigación de Compuestos Heterocíclicos
Departamento de Química
Universidad del Valle
AA25360 - Cali
Colombia
;
    'Nogueras, Manuel' .
;
Departamento de Química Inorgánica y Orgánica
Universidad de Jaén
23071 - Jaén
Spain
;
    'Salcedo, Angela' .
;
Grupo de Investigación de Compuestos Heterocíclicos
Departamento de Química
Universidad del Valle
AA25360 - Cali
Colombia
;
    "Sánchez, Adolfo" .
;
Departamento de Química Inorgánica y Orgánica
Universidad de Jaén
23071 - Jaén
Spain
;
data_IVa
_chemical_name_systematic
;
2-(4-Bromophenyl)-1,2-dihydropyrimido[1,2-a]benzimidazol-4(3H)-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C16 H12 Br N3 O'
_chemical_formula_sum     'C16 H12 Br N3 O'
_chemical_formula_weight     342.20
_chemical_melting_point     577
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y+1/2, z+1/2'
_cell_length_a     6.8807(2)
_cell_length_b     16.2254(6)
_cell_length_c     13.3379(5)
_cell_angle_alpha     90
_cell_angle_beta     111.280(2)
_cell_angle_gamma     90
_cell_volume     1387.54(8)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     3046
_cell_measurement_theta_min     3.00
_cell_measurement_theta_max     27.44
_cell_measurement_temperature     120.0(10)
_exptl_crystal_description     lath
_exptl_crystal_colour     colourless
_exptl_crystal_size_max      .20
_exptl_crystal_size_mid      .06
_exptl_crystal_size_min      .02
_exptl_crystal_density_diffrn     1.638
_exptl_crystal_density_meas     'not measured'
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     688
_exptl_absorpt_coefficient_mu     2.964
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(DENZO-SMN; Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min      .589
_exptl_absorpt_correction_T_max      .943
_exptl_special_details
;
The program Denzo-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm
(Fox & Holmes, 1966) which effectively corrects for absorption effects.
High-redundancy data were used in the scaling program, hence the `multi-scan'
code-word was used. No transmission coefficients are available from the program
(only scale factors for each frame). The scale factors in the experimental
table are calculated from the SIZE command in the SHELXL97 input file.
;
_diffrn_ambient_temperature     120.0(10)
_diffrn_radiation_type     'Mo K\a'
_diffrn_radiation_wavelength      .71073
_diffrn_radiation_source     'fine-focus sealed X-ray tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Nonius KappaCCD area-detector'
_diffrn_measurement_method     'φ scans, and ω scans with κ offsets'
_diffrn_reflns_number     8697
_diffrn_reflns_av_R_equivalents      .078
_diffrn_reflns_av_sigmaI/netI      .066
_diffrn_reflns_theta_min     3.00
_diffrn_reflns_theta_max     27.44
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max      .963
_diffrn_measured_fraction_theta_full      .993
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     -21
_diffrn_reflns_limit_k_max     21
_diffrn_reflns_limit_l_min     -17
_diffrn_reflns_limit_l_max     13
_diffrn_standards_decay_%     negligible
_reflns_number_total     3046
_reflns_number_gt     2401
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all      .060
_refine_ls_R_factor_gt      .043
_refine_ls_wR_factor_gt      .104
_refine_ls_wR_factor_ref      .114
_refine_ls_goodness_of_fit_ref     1.010
_refine_ls_restrained_S_all     1.010
_refine_ls_number_reflns     3046
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                    'w = 1/[σ²(Fo²)+(0.0658P)²] 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      .001
_refine_ls_shift/su_mean      .000
_refine_diff_density_max      .71
_refine_diff_density_min     -1.55
_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
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H'  .0000  .0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'Br' 'Br'  -.2901 2.4595
                         '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  .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     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics
                               'ORTEPII (Johnson, 1976) and PLATON (Spek, 2001)'
_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
    N1  .8909(4)  .40997(15)  .06599(19)  .0202(5) Uani d . 1 . . N
    C2  .8971(5)  .36859(17)  .1653(2)  .0202(6) Uani d . 1 . . C
    C21  .7504(5)  .41219(17)  .2108(2)  .0203(6) Uani d . 1 . . C
    C22  .5453(5)  .43433(17)  .1448(3)  .0234(7) Uani d . 1 . . C
    C23  .4160(5)  .47768(19)  .1863(2)  .0227(6) Uani d . 1 . . C
    C24  .4927(4)  .49813(17)  .2952(2)  .0200(6) Uani d . 1 . . C
    Br24  .31283(5)  .557959(18)  .34998(2)  .02561(14) Uani d . 1 . . Br
    C25  .6932(5)  .47610(18)  .3619(2)  .0226(6) Uani d . 1 . . C
    C26  .8204(5)  .43347(17)  .3187(3)  .0232(7) Uani d . 1 . . C
    C3  .8401(5)  .27790(18)  .1389(2)  .0227(6) Uani d . 1 . . C
    C4  .9671(4)  .23567(17)  .0811(2)  .0206(6) Uani d . 1 . . C
    O4  .9921(4)  .16254(12)  .07701(17)  .0271(5) Uani d . 1 . . O
    N5 1.0538(4)  .29104(14)  .02729(18)  .0174(5) Uani d . 1 . . N
    C5A 1.1695(5)  .27315(18)  -.0394(2)  .0196(6) Uani d . 1 . . C
    C6 1.2800(5)  .20374(17)  -.0502(2)  .0224(6) Uani d . 1 . . C
    C7 1.3886(5)  .21007(19)  -.1201(3)  .0256(7) Uani d . 1 . . C
    C8 1.3865(5)  .2825(2)  -.1770(3)  .0276(7) Uani d . 1 . . C
    C9 1.2770(5)  .35229(19)  -.1643(2)  .0239(7) Uani d . 1 . . C
    C9A 1.1727(4)  .34733(17)  -.0929(2)  .0197(6) Uani d . 1 . . C
    N10 1.0655(4)  .40985(15)  -.05954(19)  .0190(5) Uani d . 1 . . N
    C10A  .9990(5)  .37510(17)  .0111(2)  .0181(6) Uani d . 1 . . C
    H1  .8194  .4557  .0435  .024 Uiso calc R 1 . . H
    H2 1.0425  .3718  .2195  .024 Uiso calc R 1 . . H
    H22  .4943  .4195  .0709  .028 Uiso calc R 1 . . H
    H23  .2787  .4929  .1413  .027 Uiso calc R 1 . . H
    H25  .7430  .4900  .4361  .027 Uiso calc R 1 . . H
    H26  .9578  .4187  .3641  .028 Uiso calc R 1 . . H
    H3A  .8608  .2479  .2067  .027 Uiso calc R 1 . . H
    H3B  .6904  .2742  .0933  .027 Uiso calc R 1 . . H
    H6 1.2812  .1544  -.0117  .027 Uiso calc R 1 . . H
    H7 1.4658  .1640  -.1293  .031 Uiso calc R 1 . . H
    H8 1.4601  .2845  -.2250  .033 Uiso calc R 1 . . H
    H9 1.2744  .4014  -.2035  .029 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
    N1 C10A . 1.343(4) no
    N1 C2 . 1.472(4) no
    N1 H1 .  .8800 no
    C2 C21 . 1.527(4) no
    C2 C3 . 1.531(4) no
    C2 H2 . 1.0000 no
    C21 C26 . 1.385(4) no
    C21 C22 . 1.412(4) no
    C22 C23 . 1.396(4) no
    C22 H22 .  .9500 no
    C23 C24 . 1.393(4) no
    C23 H23 .  .9500 no
    C24 C25 . 1.389(4) no
    C24 Br24 . 1.914(3) no
    C25 C26 . 1.394(4) no
    C25 H25 .  .9500 no
    C26 H26 .  .9500 no
    C3 C4 . 1.522(4) no
    C3 H3A .  .9900 no
    C3 H3B .  .9900 no
    C4 O4 . 1.203(3) no
    C4 N5 . 1.411(4) no
    N5 C10A . 1.411(3) no
    N5 C5A . 1.422(4) no
    C5A C6 . 1.395(4) no
    C5A C9A . 1.404(4) no
    C6 C7 . 1.394(4) no
    C6 H6 .  .9500 no
    C7 C8 . 1.395(5) no
    C7 H7 .  .9500 no
    C8 C9 . 1.404(4) no
    C8 H8 .  .9500 no
    C9 C9A . 1.388(4) no
    C9 H9 .  .9500 no
    C9A N10 . 1.417(4) no
    N10 C10A . 1.314(4) 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
    C10A N1 C2 . . 117.2(2) no
    C10A N1 H1 . . 121.4 no
    C2 N1 H1 . . 121.4 no
    N1 C2 C21 . . 109.8(2) no
    N1 C2 C3 . . 108.1(2) no
    C21 C2 C3 . . 112.7(2) no
    N1 C2 H2 . . 108.7 no
    C21 C2 H2 . . 108.7 no
    C3 C2 H2 . . 108.7 no
    C26 C21 C22 . . 118.4(3) no
    C26 C21 C2 . . 119.8(3) no
    C22 C21 C2 . . 121.7(3) no
    C23 C22 C21 . . 121.1(3) no
    C23 C22 H22 . . 119.4 no
    C21 C22 H22 . . 119.4 no
    C24 C23 C22 . . 118.6(3) no
    C24 C23 H23 . . 120.7 no
    C22 C23 H23 . . 120.7 no
    C25 C24 C23 . . 121.2(3) no
    C25 C24 Br24 . . 121.0(2) no
    C23 C24 Br24 . . 117.8(2) no
    C24 C25 C26 . . 119.3(3) no
    C24 C25 H25 . . 120.3 no
    C26 C25 H25 . . 120.3 no
    C21 C26 C25 . . 121.3(3) no
    C21 C26 H26 . . 119.4 no
    C25 C26 H26 . . 119.4 no
    C4 C3 C2 . . 113.8(2) no
    C4 C3 H3A . . 108.8 no
    C2 C3 H3A . . 108.8 no
    C4 C3 H3B . . 108.8 no
    C2 C3 H3B . . 108.8 no
    H3A C3 H3B . . 107.7 no
    O4 C4 N5 . . 120.7(3) no
    O4 C4 C3 . . 125.8(3) no
    N5 C4 C3 . . 113.4(2) no
    C4 N5 C10A . . 123.7(2) no
    C4 N5 C5A . . 128.6(2) no
    C10A N5 C5A . . 106.3(2) no
    C6 C5A C9A . . 122.0(3) no
    C6 C5A N5 . . 132.8(3) no
    C9A C5A N5 . . 105.0(2) no
    C7 C6 C5A . . 117.0(3) no
    C7 C6 H6 . . 121.5 no
    C5A C6 H6 . . 121.5 no
    C6 C7 C8 . . 121.5(3) no
    C6 C7 H7 . . 119.2 no
    C8 C7 H7 . . 119.2 no
    C7 C8 C9 . . 120.9(3) no
    C7 C8 H8 . . 119.5 no
    C9 C8 H8 . . 119.5 no
    C9A C9 C8 . . 118.0(3) no
    C9A C9 H9 . . 121.0 no
    C8 C9 H9 . . 121.0 no
    C9 C9A C5A . . 120.4(3) no
    C9 C9A N10 . . 129.2(3) no
    C5A C9A N10 . . 110.4(3) no
    C10A N10 C9A . . 105.9(2) no
    N10 C10A N1 . . 128.0(3) no
    N10 C10A N5 . . 112.4(2) no
    N1 C10A N5 . . 119.6(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
    C10A N1 C2 C21 . . . . -174.8(2) no
    C10A N1 C2 C3 . . . . -51.5(3) no
    N1 C2 C21 C26 . . . . -131.3(3) no
    C3 C2 C21 C26 . . . . 108.2(3) no
    N1 C2 C21 C22 . . . . 46.5(4) no
    C3 C2 C21 C22 . . . . -74.0(3) no
    C26 C21 C22 C23 . . . .  .9(4) no
    C2 C21 C22 C23 . . . . -176.9(3) no
    C21 C22 C23 C24 . . . .  -.7(4) no
    C22 C23 C24 C25 . . . .  -.1(4) no
    C22 C23 C24 Br24 . . . . 179.7(2) no
    C23 C24 C25 C26 . . . .  .6(4) no
    Br24 C24 C25 C26 . . . . -179.2(2) no
    C22 C21 C26 C25 . . . .  -.3(4) no
    C2 C21 C26 C25 . . . . 177.5(3) no
    C24 C25 C26 C21 . . . .  -.4(4) no
    N1 C2 C3 C4 . . . . 51.5(3) no
    C21 C2 C3 C4 . . . . 173.0(2) no
    C2 C3 C4 O4 . . . . 159.2(3) no
    C2 C3 C4 N5 . . . . -22.4(4) no
    O4 C4 N5 C10A . . . . 167.4(3) no
    C3 C4 N5 C10A . . . . -11.1(4) no
    O4 C4 N5 C5A . . . . 2.5(5) no
    C3 C4 N5 C5A . . . . -175.9(3) no
    C4 N5 C5A C6 . . . . -20.1(5) no
    C10A N5 C5A C6 . . . . 173.0(3) no
    C4 N5 C5A C9A . . . . 165.7(3) no
    C10A N5 C5A C9A . . . . -1.2(3) no
    C9A C5A C6 C7 . . . . -2.3(4) no
    N5 C5A C6 C7 . . . . -175.7(3) no
    C5A C6 C7 C8 . . . .  -.2(4) no
    C6 C7 C8 C9 . . . . 1.1(5) no
    C7 C8 C9 C9A . . . .  .6(5) no
    C8 C9 C9A C5A . . . . -3.0(4) no
    C8 C9 C9A N10 . . . . 174.7(3) no
    C6 C5A C9A C9 . . . . 4.0(4) no
    N5 C5A C9A C9 . . . . 179.0(3) no
    C6 C5A C9A N10 . . . . -174.1(3) no
    N5 C5A C9A N10 . . . .  .9(3) no
    C9 C9A N10 C10A . . . . -178.2(3) no
    C5A C9A N10 C10A . . . .  -.2(3) no
    C9A N10 C10A N1 . . . . 179.3(3) no
    C9A N10 C10A N5 . . . .  -.6(3) no
    C2 N1 C10A N10 . . . . -159.2(3) no
    C2 N1 C10A N5 . . . . 20.6(4) no
    C4 N5 C10A N10 . . . . -166.6(2) no
    C5A N5 C10A N10 . . . . 1.1(3) no
    C4 N5 C10A N1 . . . . 13.6(4) no
    C5A N5 C10A N1 . . . . -178.7(2) 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
    N1 H1 N10 3_765  .88 2.30 2.943(3) 129 y
    C9 H9 CgX 3_765  .95 2.59 3.501(3) 158 y
data_Vb
_chemical_name_systematic
;
4-(4-Methylphenyl)-3,4-dihydropyrimido[1,2-a]benzimidazol-2(1H)-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C17 H15 N3 O'
_chemical_formula_sum     'C17 H15 N3 O'
_chemical_formula_weight     277.32
_chemical_melting_point     506
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P-1'
_symmetry_space_group_name_Hall     'p-1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     8.1360(3)
_cell_length_b     9.8647(4)
_cell_length_c     10.0975(5)
_cell_angle_alpha     114.8796(13)
_cell_angle_beta     94.9156(15)
_cell_angle_gamma     100.966(3)
_cell_volume     709.18(5)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     3170
_cell_measurement_theta_min     3.03
_cell_measurement_theta_max     27.50
_cell_measurement_temperature     120.0(10)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max      .1
_exptl_crystal_size_mid      .1
_exptl_crystal_size_min      .1
_exptl_crystal_density_diffrn     1.299
_exptl_crystal_density_meas     'not measured'
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     292
_exptl_absorpt_coefficient_mu      .084
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(DENZO-SMN; Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min      .992
_exptl_absorpt_correction_T_max      .992
_exptl_special_details
;
The program Denzo-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm
(Fox & Holmes, 1966) which effectively corrects for absorption effects.
High-redundancy data were used in the scaling program, hence the `multi-scan'
code-word was used. No transmission coefficients are available from the program
(only scale factors for each frame). The scale factors in the experimental
table are calculated from the SIZE command in the SHELXL97 input file.
;
_diffrn_ambient_temperature     120.0(10)
_diffrn_radiation_type     'Mo K\a'
_diffrn_radiation_wavelength      .71073
_diffrn_radiation_source     'fine-focus sealed X-ray tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Nonius KappaCCD area-detector'
_diffrn_measurement_method     'φ scans, and ω scans with κ offsets'
_diffrn_reflns_number     10703
_diffrn_reflns_av_R_equivalents      .056
_diffrn_reflns_av_sigmaI/netI      .055
_diffrn_reflns_theta_min     3.03
_diffrn_reflns_theta_max     27.50
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max      .975
_diffrn_measured_fraction_theta_full      .989
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     13
_diffrn_standards_decay_%     negligible
_reflns_number_total     3170
_reflns_number_gt     2247
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all      .075
_refine_ls_R_factor_gt      .046
_refine_ls_wR_factor_gt      .107
_refine_ls_wR_factor_ref      .120
_refine_ls_goodness_of_fit_ref     1.054
_refine_ls_restrained_S_all     1.048
_refine_ls_number_reflns     3170
_refine_ls_number_parameters     264
_refine_ls_number_restraints     52
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
            'w = 1/[σ²(Fo²)+(0.0664P)²+0.0023P] 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     <0.001
_refine_ls_shift/su_mean      .000
_refine_diff_density_max      .21
_refine_diff_density_min      -.21
_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
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H'  .0000  .0000
                         '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  .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     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics
                               'ORTEPII (Johnson, 1976) and PLATON (Spek, 2001)'
_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
    N1  .91899(12)  .67969(12)  .51394(12)  .0258(3) Uani d . 1 . . N
    C2  .90560(16)  .82721(16)  .55341(15)  .0266(3) Uani d . 1 A . C
    O2 1.01688(11)  .93793(11)  .64295(11)  .0350(3) Uani d . 1 . . O
    C3  .75014(16)  .84074(15)  .47112(16)  .0292(3) Uani d D 1 . . C
    C4A  .58901(17)  .71272(16)  .43032(16)  .0217(4) Uani d PD  .907(4) A -1 C
    C41A  .4544(3)  .71274(19)  .3174(3)  .0205(4) Uani d P  .907(4) A -1 C
    C42A  .4750(2)  .6777(2)  .1723(3)  .0272(5) Uani d P  .907(4) A -1 C
    C43A  .3473(4)  .6760(2)  .0706(2)  .0293(6) Uani d P  .907(4) A -1 C
    C44A  .1950(4)  .7105(4)  .1112(3)  .0263(7) Uani d P  .907(4) A -1 C
    C45A  .1757(3)  .7467(3)  .2567(3)  .0273(6) Uani d P  .907(4) A -1 C
    C46A  .3029(3)  .7475(2)  .35847(19)  .0229(5) Uani d P  .907(4) A -1 C
    C47A  .0573(3)  .7103(2)  .0022(3)  .0411(5) Uani d P  .907(4) A -1 C
    N5  .63728(12)  .56436(12)  .37319(12)  .0222(3) Uani d D 1 . . N
    C5A  .53518(16)  .41306(15)  .29563(14)  .0229(3) Uani d . 1 A . C
    C6  .36396(16)  .35199(16)  .23039(15)  .0305(4) Uani d . 1 . . C
    C7  .30616(18)  .19275(16)  .16268(17)  .0339(4) Uani d . 1 A . C
    C8  .41401(17)  .09745(16)  .15937(15)  .0309(4) Uani d . 1 . . C
    C9  .58416(17)  .15874(16)  .22647(14)  .0263(3) Uani d . 1 A . C
    C9A  .64417(15)  .31836(15)  .29690(14)  .0217(3) Uani d . 1 . . C
    N10  .80576(13)  .40885(13)  .37738(12)  .0251(3) Uani d . 1 A . N
    C10A  .79250(15)  .55081(15)  .42150(14)  .0217(3) Uani d . 1 A . C
    C4B  .6609(15)  .7020(14)  .3331(15)  .025(4) Uani d PD  .093(4) A -2 C
    C41B  .492(2)  .710(2)  .259(3)  .019(4) Uani d PDU  .093(4) A -2 C
    C42B  .377(4)  .735(2)  .346(2)  .017(4) Uani d PU  .093(4) A -2 C
    C43B  .215(3)  .742(3)  .292(3)  .020(4) Uani d PU  .093(4) A -2 C
    C44B  .172(3)  .712(4)  .149(4)  .013(4) Uani d PU  .093(4) A -2 C
    C45B  .280(4)  .680(3)  .070(3)  .019(4) Uani d PU  .093(4) A -2 C
    C46B  .442(3)  .684(2)  .113(3)  .022(4) Uani d PU  .093(4) A -2 C
    C47B  -.001(3)  .714(3)  .066(3)  .058(7) Uani d P  .093(4) A -2 C
    H1 1.0140  .6666  .5498  .031 Uiso calc R 1 . . H
    H3A  .7780  .8435  .3786  .035 Uiso calc R 1 A . H
    H3B  .7254  .9406  .5331  .035 Uiso calc R 1 . . H
    H4A  .5416  .7282  .5223  .026 Uiso calc PR  .907(4) A -1 H
    H42A  .5779  .6547  .1422  .033 Uiso calc PR  .907(4) A -1 H
    H43A  .3638  .6509  -.0282  .035 Uiso calc PR  .907(4) A -1 H
    H45A  .0736  .7714  .2873  .033 Uiso calc PR  .907(4) A -1 H
    H46A  .2862  .7720  .4571  .028 Uiso calc PR  .907(4) A -1 H
    H47A  .1064  .7223  -.0787  .062 Uiso calc PR  .4535(18) A -1 H
    H47B  .0056  .7960  .0526  .062 Uiso calc PR  .4535(18) A -1 H
    H47C  -.0300  .6125  -.0384  .062 Uiso calc PR  .4535(18) A -1 H
    H47D  -.0517  .6982  .0357  .062 Uiso calc PR  .4535(18) A -1 H
    H47E  .0490  .6245  -.0956  .062 Uiso calc PR  .4535(18) A -1 H
    H47F  .0847  .8080  -.0046  .062 Uiso calc PR  .4535(18) A -1 H
    H6  .2901  .4163  .2321  .037 Uiso calc R 1 A . H
    H7  .1896  .1470  .1171  .041 Uiso calc R 1 . . H
    H8  .3699  -.0114  .1102  .037 Uiso calc R 1 A . H
    H9  .6574  .0938  .2244  .032 Uiso calc R 1 . . H
    H4B  .7392  .6852  .2597  .030 Uiso calc PR  .093(4) A -2 H
    H42B  .4037  .7477  .4448  .021 Uiso calc PR  .093(4) A -2 H
    H43B  .1355  .7676  .3571  .024 Uiso calc PR  .093(4) A -2 H
    H45B  .2448  .6496  -.0327  .023 Uiso calc PR  .093(4) A -2 H
    H46B  .5199  .6689  .0467  .026 Uiso calc PR  .093(4) A -2 H
    H47G  -.0869  .6187  .0421  .087 Uiso calc PR  .0465(18) A -2 H
    H47H  .0177  .7210  -.0255  .087 Uiso calc PR  .0465(18) A -2 H
    H47I  -.0397  .8030  .1309  .087 Uiso calc PR  .0465(18) A -2 H
    H47J  .0143  .8098  .0562  .087 Uiso calc PR  .0465(18) A -2 H
    H47K  -.0903  .7074  .1238  .087 Uiso calc PR  .0465(18) A -2 H
    H47L  -.0329  .6255  -.0326  .087 Uiso calc PR  .0465(18) A -2 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
    N1 C2 . 1.3668(17) no
    N1 C10A . 1.3732(16) no
    N1 H1 .  .8800 no
    C2 O2 . 1.2176(16) no
    C2 C3 . 1.5118(17) no
    C3 C4B . 1.478(13) no
    C3 C4A . 1.5242(18) no
    C3 H3A .  .9900 no
    C3 H3B .  .9900 no
    C4A N5 . 1.4752(17) no
    C4A C41A . 1.512(2) no
    C4A H4A . 1.0000 no
    C41A C42A . 1.390(3) no
    C41A C46A . 1.391(3) no
    C42A C43A . 1.389(3) no
    C42A H42A .  .9500 no
    C43A C44A . 1.396(3) no
    C43A H43A .  .9500 no
    C44A C45A . 1.389(3) no
    C44A C47A . 1.501(3) no
    C45A C46A . 1.391(2) no
    C45A H45A .  .9500 no
    C46A H46A .  .9500 no
    C47A H47A .  .9800 no
    C47A H47B .  .9800 no
    C47A H47C .  .9800 no
    C47A H47D .  .9800 no
    C47A H47E .  .9800 no
    C47A H47F .  .9800 no
    N5 C10A . 1.3653(15) no
    N5 C5A . 1.4016(17) no
    N5 C4B . 1.555(12) no
    C5A C6 . 1.3882(18) no
    C5A C9A . 1.4080(18) no
    C6 C7 . 1.384(2) no
    C6 H6 .  .9500 no
    C7 C8 . 1.395(2) no
    C7 H7 .  .9500 no
    C8 C9 . 1.3846(19) no
    C8 H8 .  .9500 no
    C9 C9A . 1.3889(19) no
    C9 H9 .  .9500 no
    C9A N10 . 1.3948(16) no
    N10 C10A . 1.3084(17) no
    C4B C41B . 1.541(18) no
    C4B H4B . 1.0000 no
    C41B C42B . 1.32(3) no
    C41B C46B . 1.39(3) no
    C42B C43B . 1.41(3) no
    C42B H42B .  .9500 no
    C43B C44B . 1.35(3) no
    C43B H43B .  .9500 no
    C44B C45B . 1.23(3) no
    C44B C47B . 1.58(4) no
    C45B C46B . 1.34(3) no
    C45B H45B .  .9500 no
    C46B H46B .  .9500 no
    C47B H47G .  .9800 no
    C47B H47H .  .9800 no
    C47B H47I .  .9800 no
    C47B H47J .  .9800 no
    C47B H47K .  .9800 no
    C47B H47L .  .9800 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
    C2 N1 C10A . . 123.66(11) no
    C2 N1 H1 . . 118.2 no
    C10A N1 H1 . . 118.2 no
    O2 C2 N1 . . 121.28(12) no
    O2 C2 C3 . . 123.55(12) no
    N1 C2 C3 . . 115.07(11) no
    C4B C3 C2 . . 116.0(5) no
    C4B C3 C4A . . 45.5(5) no
    C2 C3 C4A . . 115.86(11) no
    C4B C3 H3A . . 65.4 no
    C2 C3 H3A . . 108.3 no
    C4A C3 H3A . . 108.3 no
    C4B C3 H3B . . 135.2 no
    C2 C3 H3B . . 108.3 no
    C4A C3 H3B . . 108.3 no
    H3A C3 H3B . . 107.4 no
    N5 C4A C41A . . 110.90(12) no
    N5 C4A C3 . . 107.85(10) no
    C41A C4A C3 . . 112.18(13) no
    N5 C4A H4A . . 108.6 no
    C41A C4A H4A . . 108.6 no
    C3 C4A H4A . . 108.6 no
    C42A C41A C46A . . 118.19(15) no
    C42A C41A C4A . . 122.4(2) no
    C46A C41A C4A . . 119.4(2) no
    C43A C42A C41A . . 120.92(17) no
    C43A C42A H42A . . 119.5 no
    C41A C42A H42A . . 119.5 no
    C42A C43A C44A . . 121.10(19) no
    C42A C43A H43A . . 119.4 no
    C44A C43A H43A . . 119.4 no
    C45A C44A C43A . . 117.7(2) no
    C45A C44A C47A . . 121.0(3) no
    C43A C44A C47A . . 121.3(2) no
    C44A C45A C46A . . 121.3(2) no
    C44A C45A H45A . . 119.4 no
    C46A C45A H45A . . 119.4 no
    C45A C46A C41A . . 120.78(17) no
    C45A C46A H46A . . 119.6 no
    C41A C46A H46A . . 119.6 no
    C10A N5 C5A . . 105.53(10) no
    C10A N5 C4A . . 122.62(10) no
    C5A N5 C4A . . 130.07(10) no
    C10A N5 C4B . . 109.9(5) no
    C5A N5 C4B . . 130.7(5) no
    C4A N5 C4B . . 45.0(5) no
    C6 C5A N5 . . 133.08(12) no
    C6 C5A C9A . . 121.84(12) no
    N5 C5A C9A . . 105.05(10) no
    C7 C6 C5A . . 116.74(13) no
    C7 C6 H6 . . 121.6 no
    C5A C6 H6 . . 121.6 no
    C6 C7 C8 . . 121.96(13) no
    C6 C7 H7 . . 119.0 no
    C8 C7 H7 . . 119.0 no
    C9 C8 C7 . . 121.16(13) no
    C9 C8 H8 . . 119.4 no
    C7 C8 H8 . . 119.4 no
    C8 C9 C9A . . 117.79(13) no
    C8 C9 H9 . . 121.1 no
    C9A C9 H9 . . 121.1 no
    C9 C9A N10 . . 129.38(12) no
    C9 C9A C5A . . 120.45(12) no
    N10 C9A C5A . . 110.15(11) no
    C10A N10 C9A . . 104.27(10) no
    N10 C10A N5 . . 114.87(11) no
    N10 C10A N1 . . 124.52(11) no
    N5 C10A N1 . . 120.56(11) no
    C3 C4B C41B . . 115.7(12) no
    C3 C4B N5 . . 106.1(8) no
    C41B C4B N5 . . 112.0(11) no
    C3 C4B H4B . . 107.6 no
    C41B C4B H4B . . 107.6 no
    N5 C4B H4B . . 107.6 no
    C42B C41B C46B . . 117.3(16) no
    C42B C41B C4B . . 114(2) no
    C46B C41B C4B . . 129(2) no
    C41B C42B C43B . . 120.2(17) no
    C41B C42B H42B . . 119.9 no
    C43B C42B H42B . . 119.9 no
    C44B C43B C42B . . 120(2) no
    C44B C43B H43B . . 120.1 no
    C42B C43B H43B . . 120.1 no
    C45B C44B C43B . . 118(3) no
    C45B C44B C47B . . 114(3) no
    C43B C44B C47B . . 128(3) no
    C44B C45B C46B . . 127(2) no
    C44B C45B H45B . . 116.5 no
    C46B C45B H45B . . 116.5 no
    C45B C46B C41B . . 118(2) no
    C45B C46B H46B . . 121.2 no
    C41B C46B H46B . . 121.2 no
    C44B C47B H47G . . 109.5 no
    C44B C47B H47H . . 109.5 no
    H47G C47B H47H . . 109.5 no
    C44B C47B H47I . . 109.5 no
    H47G C47B H47I . . 109.5 no
    H47H C47B H47I . . 109.5 no
    C44B C47B H47J . . 109.5 no
    H47G C47B H47J . . 141.1 no
    H47H C47B H47J . . 56.3 no
    H47I C47B H47J . . 56.3 no
    C44B C47B H47K . . 109.5 no
    H47G C47B H47K . . 56.3 no
    H47H C47B H47K . . 141.1 no
    H47I C47B H47K . . 56.3 no
    H47J C47B H47K . . 109.5 no
    C44B C47B H47L . . 109.5 no
    H47G C47B H47L . . 56.3 no
    H47H C47B H47L . . 56.3 no
    H47I C47B H47L . . 141.1 no
    H47J C47B H47L . . 109.5 no
    H47K C47B H47L . . 109.5 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
    C10A N1 C2 O2 . . . . 175.39(12) no
    C10A N1 C2 C3 . . . . -8.25(19) no
    O2 C2 C3 C4B . . . . 159.6(6) no
    N1 C2 C3 C4B . . . . -16.6(6) no
    O2 C2 C3 C4A . . . . -149.42(14) no
    N1 C2 C3 C4A . . . . 34.31(17) no
    C4B C3 C4A N5 . . . . 58.4(7) no
    C2 C3 C4A N5 . . . . -43.44(16) no
    C4B C3 C4A C41A . . . . -64.0(7) no
    C2 C3 C4A C41A . . . . -165.86(15) no
    N5 C4A C41A C42A . . . . -53.9(2) no
    C3 C4A C41A C42A . . . . 66.80(19) no
    N5 C4A C41A C46A . . . . 125.51(16) no
    C3 C4A C41A C46A . . . . -113.82(17) no
    C46A C41A C42A C43A . . . .  -.6(3) no
    C4A C41A C42A C43A . . . . 178.77(16) no
    C41A C42A C43A C44A . . . .  .5(3) no
    C42A C43A C44A C45A . . . .  .1(4) no
    C42A C43A C44A C47A . . . . 179.4(2) no
    C43A C44A C45A C46A . . . .  -.5(4) no
    C47A C44A C45A C46A . . . . -179.8(2) no
    C44A C45A C46A C41A . . . .  .4(3) no
    C42A C41A C46A C45A . . . .  .2(3) no
    C4A C41A C46A C45A . . . . -179.24(16) no
    C41A C4A N5 C10A . . . . 154.46(15) no
    C3 C4A N5 C10A . . . . 31.26(17) no
    C41A C4A N5 C5A . . . . -43.0(2) no
    C3 C4A N5 C5A . . . . -166.21(12) no
    C41A C4A N5 C4B . . . . 68.4(7) no
    C3 C4A N5 C4B . . . . -54.8(7) no
    C10A N5 C5A C6 . . . . 174.71(15) no
    C4A N5 C5A C6 . . . . 9.9(2) no
    C4B N5 C5A C6 . . . . -50.4(7) no
    C10A N5 C5A C9A . . . . -3.35(13) no
    C4A N5 C5A C9A . . . . -168.14(12) no
    C4B N5 C5A C9A . . . . 131.5(6) no
    N5 C5A C6 C7 . . . . -179.56(14) no
    C9A C5A C6 C7 . . . . -1.8(2) no
    C5A C6 C7 C8 . . . .  -.2(2) no
    C6 C7 C8 C9 . . . . 1.1(2) no
    C7 C8 C9 C9A . . . .  -.2(2) no
    C8 C9 C9A N10 . . . . 176.98(12) no
    C8 C9 C9A C5A . . . . -1.7(2) no
    C6 C5A C9A C9 . . . . 2.8(2) no
    N5 C5A C9A C9 . . . . -178.90(11) no
    C6 C5A C9A N10 . . . . -176.15(12) no
    N5 C5A C9A N10 . . . . 2.18(14) no
    C9 C9A N10 C10A . . . . -178.84(14) no
    C5A C9A N10 C10A . . . .  -.05(14) no
    C9A N10 C10A N5 . . . . -2.30(15) no
    C9A N10 C10A N1 . . . . 175.22(12) no
    C5A N5 C10A N10 . . . . 3.71(15) no
    C4A N5 C10A N10 . . . . 169.91(12) no
    C4B N5 C10A N10 . . . . -141.5(5) no
    C5A N5 C10A N1 . . . . -173.92(11) no
    C4A N5 C10A N1 . . . . -7.72(19) no
    C4B N5 C10A N1 . . . . 40.9(6) no
    C2 N1 C10A N10 . . . . 176.90(13) no
    C2 N1 C10A N5 . . . . -5.7(2) no
    C2 C3 C4B C41B . . . . 173.3(12) no
    C4A C3 C4B C41B . . . . 71.7(13) no
    C2 C3 C4B N5 . . . . 48.4(8) no
    C4A C3 C4B N5 . . . . -53.2(5) no
    C10A N5 C4B C3 . . . . -60.1(8) no
    C5A N5 C4B C3 . . . . 166.5(3) no
    C4A N5 C4B C3 . . . . 56.6(6) no
    C10A N5 C4B C41B . . . . 172.7(12) no
    C5A N5 C4B C41B . . . . 39.3(15) no
    C4A N5 C4B C41B . . . . -70.6(13) no
    C3 C4B C41B C42B . . . . -59(2) no
    N5 C4B C41B C42B . . . . 63.2(19) no
    C3 C4B C41B C46B . . . . 126.4(19) no
    N5 C4B C41B C46B . . . . -112(2) no
    C46B C41B C42B C43B . . . . -3(3) no
    C4B C41B C42B C43B . . . . -178.8(18) no
    C41B C42B C43B C44B . . . . 5(4) no
    C42B C43B C44B C45B . . . . -1(4) no
    C42B C43B C44B C47B . . . . -180(2) no
    C43B C44B C45B C46B . . . . -6(5) no
    C47B C44B C45B C46B . . . . 173(2) no
    C44B C45B C46B C41B . . . . 7(4) no
    C42B C41B C46B C45B . . . . -2(3) no
    C4B C41B C46B C45B . . . . 172.5(19) 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
    N1 H1 N10 2_766  .88 1.98 2.8481(16) 167 y
    C3 H3A O2 2_776  .99 2.56 3.2561(19) 127 y
    C4A H4A CgY 2_666 1.00 2.43 3.419(16) 159 y
