##############################################################################
###                                                                        ###
###        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     'manuel editing of form.cif'
_journal_date_recd_electronic     2003-10-01
_journal_date_accepted     2003-11-17
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2003
_journal_volume     59
_journal_issue     12
_journal_page_first     o1990
_journal_page_last     o1991
_journal_paper_category     EO
_publ_contact_author_name     'Marie-Rose Spirlet'
_publ_contact_author_address
;
Département de Physique B5
Université de Liège
Sart Tilman
B-4000 Liège
Belgium
;
_publ_contact_author_email     mrspirlet@ulg.ac.be
_publ_contact_author_fax     '+32 04 3662813'
_publ_contact_author_phone     '+32 04 3663763'
_publ_section_title
;
8-Methyl-6-(4-methylpiperazin-1-yl)-11H-pyrido[2,3-b][1,4]benzodiazepine
;
loop_
    _publ_author_name
    _publ_author_address
    'Marie-Rose Spirlet'
;
Département de Physique, B5
Université de Liège
Sart Tilman
B-4000 Liège
Belgium
;
    'Amaury Graulich'
;
Natural and Synthetic Drugs Research Center
Laboratory of Medicinal Chemistry
1 avenue de l'Hopital (B36)
B-4000 Liège
Belgium
;
    'Jean-Francois Liégeois'
;
Natural and Synthetic Drugs Research Center
Laboratory of Medicinal Chemistry
1 avenue de l'Hopital (B36)
B-4000 Liège
Belgium
;
data_I
_chemical_name_systematic
;
8-methyl-6-(4-methylpiperazin-1-yl)-11H-pyrido[2,3-b][1,4]benzodiazepine
;
_chemical_name_common     ?
_chemical_formula_moiety     'C18 H21 N5'
_chemical_formula_sum     'C18 H21 N5'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac     'C18 H21 N5'
_chemical_formula_weight     307.40
_chemical_melting_point     ?
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P b c a'
_symmetry_space_group_name_Hall     '-P 2ac 2ab'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    '-x, y+1/2, -z+1/2'
    'x+1/2, -y+1/2, -z'
    '-x, -y, -z'
    'x-1/2, y, -z-1/2'
    'x, -y-1/2, z-1/2'
    '-x-1/2, y-1/2, z'
_cell_length_a     13.0331(19)
_cell_length_b     15.610(3)
_cell_length_c     16.514(3)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     3359.7(10)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     21
_cell_measurement_theta_min     15.22
_cell_measurement_theta_max     17.49
_cell_measurement_temperature     293(2)
_exptl_crystal_description     prismatic
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.35
_exptl_crystal_size_mid     0.30
_exptl_crystal_size_min     0.25
_exptl_crystal_density_diffrn     1.215
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1312
_exptl_absorpt_coefficient_mu     0.076
_exptl_absorpt_correction_type     psi-scan
_exptl_absorpt_process_details     'NORTH et al. (1968)'
_exptl_absorpt_correction_T_min     0.915
_exptl_absorpt_correction_T_max     0.964
_exptl_special_details
;
?
;
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker P4'
_diffrn_measurement_method     '2θ/ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     6621
_diffrn_reflns_av_R_equivalents     0.0309
_diffrn_reflns_av_sigmaI/netI     0.0510
_diffrn_reflns_theta_min     2.38
_diffrn_reflns_theta_max     25.00
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     1.0
_diffrn_measured_fraction_theta_full     1.0
_diffrn_reflns_limit_h_min     -1
_diffrn_reflns_limit_h_max     15
_diffrn_reflns_limit_k_min     -1
_diffrn_reflns_limit_k_max     18
_diffrn_reflns_limit_l_min     -1
_diffrn_reflns_limit_l_max     19
_diffrn_standards_number     3
_diffrn_standards_interval_count     97
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     0
_refine_special_details
;
?
;
_reflns_number_total     2952
_reflns_number_gt     1441
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1365
_refine_ls_R_factor_gt     0.0498
_refine_ls_wR_factor_gt     0.0839
_refine_ls_wR_factor_ref     0.1058
_refine_ls_goodness_of_fit_ref     0.919
_refine_ls_restrained_S_all     0.919
_refine_ls_number_reflns     2952
_refine_ls_number_parameters     214
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                  'calc w=1/[σ²(Fo²)+(0.034P)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     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.146
_refine_diff_density_min     -0.152
_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' 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'
_computing_data_collection     'XSCANS (Siemens, 1996)'
_computing_cell_refinement     'XSCANS'
_computing_data_reduction     'SHELXTL (Siemens, 1991)'
_computing_structure_solution     'SHELXTL'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material     'SHELXTL'
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
    C1 0.1385(2) -0.17988(17) 0.39975(17) 0.0422(7) Uani d . 1 . . C
    C2 0.2428(2) -0.19645(19) 0.40642(17) 0.0505(8) Uani d . 1 . . C
    H2 0.2665 -0.2522 0.3995 0.061 Uiso calc R 1 . . H
    C3 0.3117(2) -0.13219(19) 0.42307(16) 0.0485(8) Uani d . 1 . . C
    H3 0.3810 -0.1453 0.4283 0.058 Uiso calc R 1 . . H
    C4 0.27932(19) -0.04816(18) 0.43214(15) 0.0377(7) Uani d . 1 . . C
    N5 0.35215(17) 0.01730(15) 0.45089(14) 0.0435(6) Uani d D 1 . . N
    C6 0.33915(19) 0.05731(17) 0.52705(16) 0.0375(7) Uani d . 1 . . C
    N7 0.42085(16) 0.05835(15) 0.57517(14) 0.0462(6) Uani d . 1 . . N
    C8 0.4111(2) 0.09548(17) 0.64822(18) 0.0515(8) Uani d . 1 . . C
    H8 0.4684 0.0981 0.6817 0.062 Uiso calc R 1 . . H
    C9 0.3207(2) 0.12962(18) 0.67570(17) 0.0506(8) Uani d . 1 . . C
    H9 0.3153 0.1511 0.7280 0.061 Uiso calc R 1 . . H
    C10 0.2378(2) 0.13119(17) 0.62343(18) 0.0458(7) Uani d . 1 . . C
    H10 0.1766 0.1564 0.6400 0.055 Uiso calc R 1 . . H
    C11 0.24461(18) 0.09568(16) 0.54676(16) 0.0347(7) Uani d . 1 . . C
    N12 0.16467(15) 0.11225(13) 0.49219(13) 0.0377(6) Uani d . 1 . . N
    C13 0.13708(18) 0.06056(17) 0.43574(16) 0.0338(7) Uani d . 1 . . C
    C14 0.17614(18) -0.02847(16) 0.42345(15) 0.0333(6) Uani d . 1 . . C
    C15 0.10745(19) -0.09536(16) 0.40851(14) 0.0374(7) Uani d . 1 . . C
    H15 0.0379 -0.0827 0.4043 0.045 Uiso calc R 1 . . H
    N16 0.05588(15) 0.08543(13) 0.38767(12) 0.0391(6) Uani d . 1 . . N
    C17 0.04449(18) 0.06192(18) 0.30254(15) 0.0415(7) Uani d . 1 . . C
    H17A 0.0801 0.0085 0.2923 0.050 Uiso calc R 1 . . H
    H17B 0.0750 0.1058 0.2687 0.050 Uiso calc R 1 . . H
    C18 -0.06735(18) 0.05210(18) 0.28135(16) 0.0461(7) Uani d . 1 . . C
    H18A -0.0742 0.0379 0.2244 0.055 Uiso calc R 1 . . H
    H18B -0.0970 0.0058 0.3128 0.055 Uiso calc R 1 . . H
    N19 -0.12201(15) 0.13167(14) 0.29836(13) 0.0420(6) Uani d . 1 . . N
    C20 -0.11061(19) 0.15301(17) 0.38408(16) 0.0445(8) Uani d . 1 . . C
    H20A -0.1399 0.1076 0.4169 0.053 Uiso calc R 1 . . H
    H20B -0.1476 0.2055 0.3958 0.053 Uiso calc R 1 . . H
    C21 0.00017(19) 0.16419(16) 0.40524(17) 0.0436(7) Uani d . 1 . . C
    H21A 0.0290 0.2111 0.3741 0.052 Uiso calc R 1 . . H
    H21B 0.0067 0.1781 0.4623 0.052 Uiso calc R 1 . . H
    C22 -0.23000(19) 0.1241(2) 0.27616(19) 0.0639(9) Uani d . 1 . . C
    H22A -0.2354 0.1089 0.2200 0.096 Uiso calc R 1 . . H
    H22B -0.2639 0.1778 0.2853 0.096 Uiso calc R 1 . . H
    H22C -0.2618 0.0805 0.3086 0.096 Uiso calc R 1 . . H
    C23 0.0626(2) -0.25075(17) 0.38410(18) 0.0643(10) Uani d . 1 . . C
    H23A -0.0055 -0.2306 0.3953 0.096 Uiso calc R 1 . . H
    H23B 0.0780 -0.2986 0.4185 0.096 Uiso calc R 1 . . H
    H23C 0.0670 -0.2682 0.3285 0.096 Uiso calc R 1 . . H
    H5 0.4185(14) -0.0017(16) 0.4458(17) 0.066(10) Uiso d D 1 . . H
_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
    C1 C15 . 1.388(3) ?
    C1 C2 . 1.388(3) ?
    C1 C23 . 1.506(4) ?
    C2 C3 . 1.374(4) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.386(4) ?
    C3 H3 . 0.9300 ?
    C4 C14 . 1.387(3) ?
    C4 N5 . 1.429(3) ?
    N5 C6 . 1.415(3) ?
    N5 H5 . 0.917(16) ?
    C6 N7 . 1.329(3) ?
    C6 C11 . 1.408(3) ?
    N7 C8 . 1.344(3) ?
    C8 C9 . 1.370(4) ?
    C8 H8 . 0.9300 ?
    C9 C10 . 1.383(3) ?
    C9 H9 . 0.9300 ?
    C10 C11 . 1.385(3) ?
    C10 H10 . 0.9300 ?
    C11 N12 . 1.402(3) ?
    N12 C13 . 1.284(3) ?
    C13 N16 . 1.379(3) ?
    C13 C14 . 1.494(3) ?
    C14 C15 . 1.397(3) ?
    C15 H15 . 0.9300 ?
    N16 C21 . 1.457(3) ?
    N16 C17 . 1.461(3) ?
    C17 C18 . 1.507(3) ?
    C17 H17A . 0.9700 ?
    C17 H17B . 0.9700 ?
    C18 N19 . 1.459(3) ?
    C18 H18A . 0.9700 ?
    C18 H18B . 0.9700 ?
    N19 C22 . 1.459(3) ?
    N19 C20 . 1.462(3) ?
    C20 C21 . 1.496(3) ?
    C20 H20A . 0.9700 ?
    C20 H20B . 0.9700 ?
    C21 H21A . 0.9700 ?
    C21 H21B . 0.9700 ?
    C22 H22A . 0.9600 ?
    C22 H22B . 0.9600 ?
    C22 H22C . 0.9600 ?
    C23 H23A . 0.9600 ?
    C23 H23B . 0.9600 ?
    C23 H23C . 0.9600 ?
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
    C15 C1 C2 . . 117.0(3) ?
    C15 C1 C23 . . 121.7(2) ?
    C2 C1 C23 . . 121.3(3) ?
    C3 C2 C1 . . 121.3(3) ?
    C3 C2 H2 . . 119.3 ?
    C1 C2 H2 . . 119.3 ?
    C2 C3 C4 . . 120.9(3) ?
    C2 C3 H3 . . 119.6 ?
    C4 C3 H3 . . 119.6 ?
    C3 C4 C14 . . 119.6(2) ?
    C3 C4 N5 . . 119.9(2) ?
    C14 C4 N5 . . 120.5(3) ?
    C6 N5 C4 . . 115.4(2) ?
    C6 N5 H5 . . 109.7(18) ?
    C4 N5 H5 . . 112.0(17) ?
    N7 C6 C11 . . 123.9(2) ?
    N7 C6 N5 . . 116.2(2) ?
    C11 C6 N5 . . 119.9(2) ?
    C6 N7 C8 . . 117.8(2) ?
    N7 C8 C9 . . 123.1(3) ?
    N7 C8 H8 . . 118.4 ?
    C9 C8 H8 . . 118.4 ?
    C8 C9 C10 . . 118.2(3) ?
    C8 C9 H9 . . 120.9 ?
    C10 C9 H9 . . 120.9 ?
    C9 C10 C11 . . 120.9(3) ?
    C9 C10 H10 . . 119.6 ?
    C11 C10 H10 . . 119.6 ?
    C10 C11 N12 . . 117.8(2) ?
    C10 C11 C6 . . 116.0(2) ?
    N12 C11 C6 . . 125.5(2) ?
    C13 N12 C11 . . 124.0(2) ?
    N12 C13 N16 . . 117.1(2) ?
    N12 C13 C14 . . 126.0(2) ?
    N16 C13 C14 . . 116.4(2) ?
    C4 C14 C15 . . 118.3(2) ?
    C4 C14 C13 . . 121.5(2) ?
    C15 C14 C13 . . 120.1(2) ?
    C1 C15 C14 . . 122.8(2) ?
    C1 C15 H15 . . 118.6 ?
    C14 C15 H15 . . 118.6 ?
    C13 N16 C21 . . 120.4(2) ?
    C13 N16 C17 . . 124.2(2) ?
    C21 N16 C17 . . 110.7(2) ?
    N16 C17 C18 . . 110.3(2) ?
    N16 C17 H17A . . 109.6 ?
    C18 C17 H17A . . 109.6 ?
    N16 C17 H17B . . 109.6 ?
    C18 C17 H17B . . 109.6 ?
    H17A C17 H17B . . 108.1 ?
    N19 C18 C17 . . 109.9(2) ?
    N19 C18 H18A . . 109.7 ?
    C17 C18 H18A . . 109.7 ?
    N19 C18 H18B . . 109.7 ?
    C17 C18 H18B . . 109.7 ?
    H18A C18 H18B . . 108.2 ?
    C18 N19 C22 . . 110.7(2) ?
    C18 N19 C20 . . 109.3(2) ?
    C22 N19 C20 . . 111.1(2) ?
    N19 C20 C21 . . 110.5(2) ?
    N19 C20 H20A . . 109.5 ?
    C21 C20 H20A . . 109.5 ?
    N19 C20 H20B . . 109.5 ?
    C21 C20 H20B . . 109.5 ?
    H20A C20 H20B . . 108.1 ?
    N16 C21 C20 . . 109.6(2) ?
    N16 C21 H21A . . 109.7 ?
    C20 C21 H21A . . 109.7 ?
    N16 C21 H21B . . 109.7 ?
    C20 C21 H21B . . 109.7 ?
    H21A C21 H21B . . 108.2 ?
    N19 C22 H22A . . 109.5 ?
    N19 C22 H22B . . 109.5 ?
    H22A C22 H22B . . 109.5 ?
    N19 C22 H22C . . 109.5 ?
    H22A C22 H22C . . 109.5 ?
    H22B C22 H22C . . 109.5 ?
    C1 C23 H23A . . 109.5 ?
    C1 C23 H23B . . 109.5 ?
    H23A C23 H23B . . 109.5 ?
    C1 C23 H23C . . 109.5 ?
    H23A C23 H23C . . 109.5 ?
    H23B C23 H23C . . 109.5 ?
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
    N5 H5 N7 5_656 0.917(16) 2.300(17) 3.214(3) 175(2)
