data_2011685
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2001
_journal_volume  57
_journal_page_first  104
_journal_page_last  105
_publ_section_title
;
Phenazine-2,3-diamine
;
loop_
_publ_author_name
  'Doyle, Robert P.'
  'Kruger, Paul E.'
  'Mackie, Philip R.'
  'Nieuwenhuyzen, Mark.'
_chemical_formula_moiety  'C12 H10 N4'
_chemical_formula_sum  'C12 H10 N4'
_chemical_formula_structural  'C12 H10 N4'
_chemical_formula_weight  210.24
_symmetry_cell_setting  Orthorhombic
_symmetry_space_group_name_H-M  'P 21 21 21'
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'
_cell_length_a  4.8355(8)
_cell_length_b  11.583(2)
_cell_length_c  17.304(3)
_cell_angle_alpha  90.00
_cell_angle_beta  90.00
_cell_angle_gamma  90.00
_cell_volume  969.2(3)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.442
_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
  N1  -.6437(5)  .40416(18)  .61117(11)  .0326(6) Uani d . 1 . . N
  H1A  -.6772  .3312  .6109  .039 Uiso calc R 1 . . H
  H1B  -.7240  .4481  .6444  .039 Uiso calc R 1 . . H
  C2  -.4623(5)  .45044(19)  .55864(13)  .0225(5) Uani d . 1 . . C
  C3  -.3303(5)  .38408(18)  .50493(12)  .0235(5) Uani d . 1 . . C
  H3  -.3727  .3059  .5020  .028 Uiso calc R 1 . . H
  C4  -.1325(5)  .42995(18)  .45394(12)  .0215(5) Uani d . 1 . . C
  N5  -.0064(4)  .36121(15)  .40245(11)  .0233(5) Uani d . 1 . . N
  C6  .1894(5)  .4090(2)  .35679(12)  .0227(5) Uani d . 1 . . C
  C7  .3380(5)  .3399(2)  .30386(13)  .0276(6) Uani d . 1 . . C
  H7  .2976  .2616  .3001  .033 Uiso calc R 1 . . H
  C8  .5403(5)  .3862(2)  .25808(14)  .0301(6) Uani d . 1 . . C
  H8  .6373  .3391  .2240  .036 Uiso calc R 1 . . H
  C9  .6025(5)  .5054(2)  .26237(13)  .0294(6) Uani d . 1 . . C
  H9  .7396  .5364  .2309  .035 Uiso calc R 1 . . H
  C10  .4629(5)  .5750(2)  .31218(13)  .0276(6) Uani d . 1 . . C
  H10  .5060  .6531  .3143  .033 Uiso calc R 1 . . H
  C11  .2523(5)  .53033(19)  .36109(13)  .0237(5) Uani d . 1 . . C
  N12  .1178(4)  .60103(16)  .41102(10)  .0243(5) Uani d . 1 . . N
  C13  -.0689(5)  .55304(18)  .45788(12)  .0213(5) Uani d . 1 . . C
  C14  -.2120(5)  .62085(18)  .51267(13)  .0240(5) Uani d . 1 . . C
  H14  -.1745  .6995  .5155  .029 Uiso calc R 1 . . H
  C15  -.4038(5)  .57448(18)  .56162(12)  .0226(5) Uani d . 1 . . C
  N16  -.5416(5)  .64086(16)  .61467(11)  .0295(5) Uani d . 1 . . N
  H16A  -.5082  .7136  .6177  .035 Uiso calc R 1 . . H
  H16B  -.6616  .6097  .6449  .035 Uiso calc R 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
  N1  .0369(13)  .0217(10)  .0391(11)  -.0029(11)  .0099(11)  -.0002(9)
  C2  .0197(12)  .0202(11)  .0276(11)  -.0006(11)  -.0048(10)  .0026(9)
  C3  .0239(12)  .0161(10)  .0304(11)  -.0015(11)  -.0023(11)  .0032(9)
  C4  .0214(12)  .0161(10)  .0268(11)  -.0003(11)  -.0064(11)  .0009(9)
  N5  .0236(11)  .0186(9)  .0277(9)  .0005(10)  -.0017(9)  .0009(8)
  C6  .0212(12)  .0227(11)  .0240(11)  -.0006(11)  -.0055(10)  .0028(9)
  C7  .0277(13)  .0218(11)  .0332(12)  -.0016(11)  -.0019(12)  -.0038(10)
  C8  .0271(13)  .0319(12)  .0313(12)  .0020(12)  .0019(11)  -.0040(11)
  C9  .0254(13)  .0322(13)  .0306(12)  -.0013(11)  .0015(12)  .0073(10)
  C10  .0287(13)  .0243(11)  .0299(12)  -.0029(12)  .0003(11)  .0041(10)
  C11  .0235(13)  .0193(11)  .0283(11)  .0027(11)  -.0053(11)  .0012(9)
  N12  .0250(11)  .0187(9)  .0290(10)  .0000(10)  -.0017(9)  .0010(8)
  C13  .0201(13)  .0163(10)  .0275(11)  .0001(10)  -.0022(10)  .0025(9)
  C14  .0241(12)  .0151(10)  .0328(11)  -.0001(11)  -.0047(11)  -.0006(9)
  C15  .0229(12)  .0192(11)  .0255(11)  .0027(11)  -.0037(11)  .0011(9)
  N16  .0343(12)  .0201(10)  .0342(11)  .0011(10)  .0059(10)  -.0012(8)
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 . 1.372(3) yes
  C2 C3 . 1.365(3) ?
  C2 C15 . 1.465(3) ?
  C3 C4 . 1.406(3) ?
  C4 N5 . 1.342(3) yes
  C4 C13 . 1.460(3) ?
  N5 C6 . 1.352(3) yes
  C6 C7 . 1.413(3) ?
  C6 C11 . 1.439(3) ?
  C7 C8 . 1.368(3) ?
  C8 C9 . 1.415(3) ?
  C9 C10 . 1.359(3) ?
  C10 C11 . 1.421(3) ?
  C11 N12 . 1.357(3) yes
  N12 C13 . 1.335(3) yes
  C13 C14 . 1.412(3) ?
  C14 C15 . 1.366(3) ?
  C15 N16 . 1.371(3) yes