data_2202618
_journal_name_full  'Acta Crystallographica, Section E'
_journal_year  2003
_journal_volume  59
_journal_page_first  o1990
_journal_page_last  o1991
_publ_section_title
;
8-Methyl-6-(4-methylpiperazin-1-yl)-11H-pyrido[2,3-b][1,4]benzodiazepine
;
loop_
_publ_author_name
  'Marie-Rose Spirlet'
  'Amaury Graulich'
  'Jean-Francois Li\'egeois'
_chemical_formula_moiety  'C18 H21 N5'
_chemical_formula_sum  'C18 H21 N5'
_chemical_formula_iupac  'C18 H21 N5'
_chemical_formula_weight  307.40
_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_temperature  293(2)
_exptl_crystal_density_diffrn  1.215
_diffrn_ambient_temperature  293(2)
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
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
  C1 0.0485(18) 0.0380(17) 0.0401(17) -0.0017(14) 0.0026(15) -0.0057(14)
  C2 0.0543(19) 0.0424(18) 0.055(2) 0.0123(16) 0.0030(18) -0.0049(16)
  C3 0.0400(16) 0.0509(19) 0.055(2) 0.0157(17) -0.0052(16) -0.0012(17)
  C4 0.0327(15) 0.0434(18) 0.0369(16) -0.0015(15) 0.0007(14) 0.0022(14)
  N5 0.0319(14) 0.0577(16) 0.0410(14) 0.0058(13) 0.0006(12) -0.0038(13)
  C6 0.0286(15) 0.0425(16) 0.0414(17) -0.0043(15) -0.0044(14) 0.0087(15)
  N7 0.0385(13) 0.0566(15) 0.0433(15) -0.0011(13) -0.0102(13) 0.0037(13)
  C8 0.0477(19) 0.0558(19) 0.051(2) -0.0035(17) -0.0164(17) 0.0060(18)
  C9 0.0576(19) 0.057(2) 0.0372(18) -0.0008(17) -0.0101(17) -0.0010(16)
  C10 0.0432(17) 0.0447(18) 0.0495(19) 0.0035(15) -0.0043(16) -0.0019(15)
  C11 0.0335(16) 0.0343(16) 0.0363(16) -0.0035(13) -0.0072(14) 0.0041(13)
  N12 0.0351(13) 0.0392(14) 0.0387(14) 0.0038(12) -0.0113(11) -0.0024(11)
  C13 0.0219(14) 0.0415(16) 0.0380(16) 0.0013(14) 0.0024(13) 0.0082(15)
  C14 0.0308(15) 0.0374(16) 0.0318(15) 0.0009(14) -0.0033(13) 0.0005(13)
  C15 0.0359(15) 0.0413(16) 0.0350(16) 0.0051(14) -0.0033(14) -0.0011(14)
  N16 0.0370(13) 0.0445(13) 0.0358(13) 0.0089(11) -0.0101(12) -0.0046(11)
  C17 0.0332(16) 0.0544(17) 0.0368(17) 0.0050(14) 0.0018(13) 0.0025(15)
  C18 0.0386(16) 0.0583(19) 0.0416(17) 0.0004(16) -0.0047(15) -0.0037(15)
  N19 0.0289(12) 0.0510(14) 0.0461(15) 0.0026(12) -0.0066(12) 0.0075(13)
  C20 0.0359(16) 0.0482(19) 0.0494(19) 0.0099(14) -0.0019(16) 0.0028(15)
  C21 0.0432(16) 0.0412(16) 0.0462(19) 0.0092(15) -0.0045(16) 0.0011(14)
  C22 0.0341(17) 0.081(2) 0.076(2) 0.0030(17) -0.0147(17) 0.009(2)
  C23 0.075(2) 0.0479(18) 0.069(2) -0.0007(18) 0.002(2) -0.0123(18)
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 ?