data_2100009
_journal_name_full  'Acta Crystallographica, Section B'
_journal_year  2005
_journal_volume  61
_journal_page_first  164
_journal_page_last  173
_chemical_formula_moiety  'C16 H16 Cl2 Cu N4'
_chemical_formula_sum  'C16 H16 Cl2 Cu N4'
_chemical_formula_weight  398.77
_symmetry_cell_setting  orthorhombic
_symmetry_space_group_name_H-M  'P b c a'
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  11.6899(6)
_cell_length_b  14.9843(8)
_cell_length_c  19.2115(9)
_cell_angle_alpha  90.00
_cell_angle_beta  90.00
_cell_angle_gamma  90.00
_cell_volume  3365.2(3)
_cell_formula_units_Z  8
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.574
_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
  Cu1 0.751430(18) 0.839560(17) 0.548815(12) 0.03193(8) Uani d . 1 . . Cu
  Cl1 0.71694(4) 0.74685(4) 0.63721(3) 0.04276(13) Uani d . 1 . . Cl
  Cl2 0.93311(4) 0.86988(5) 0.56060(3) 0.05205(15) Uani d . 1 . . Cl
  C3 0.79496(17) 0.81698(14) 0.38867(10) 0.0364(4) Uani d . 1 . . C
  C4 0.72127(18) 0.80284(16) 0.33277(11) 0.0403(5) Uani d . 1 . . C
  H4A 0.7428 0.7869 0.2879 0.048 Uiso calc R 1 . . H
  C5 0.61204(17) 0.81652(13) 0.35544(10) 0.0337(4) Uani d . 1 . . C
  C6 0.54197(15) 0.86338(12) 0.47575(9) 0.0281(3) Uani d . 1 . . C
  C7 0.42510(15) 0.86907(13) 0.46564(10) 0.0323(4) Uani d . 1 . . C
  H7A 0.3915 0.8540 0.4233 0.039 Uiso calc R 1 . . H
  C8 0.36002(16) 0.89850(13) 0.52199(10) 0.0330(4) Uani d . 1 . . C
  C9 0.52140(15) 0.91422(12) 0.58829(9) 0.0297(4) Uani d . 1 . . C
  C10 0.57579(16) 0.94086(13) 0.65468(9) 0.0321(4) Uani d . 1 . . C
  C11 0.5195(2) 0.92555(15) 0.71717(11) 0.0450(5) Uani d . 1 . . C
  H11A 0.4460 0.9019 0.7172 0.054 Uiso calc R 1 . . H
  C12 0.5732(3) 0.94568(18) 0.77950(12) 0.0581(6) Uani d . 1 . . C
  H12A 0.5362 0.9342 0.8214 0.070 Uiso calc R 1 . . H
  C13 0.6811(2) 0.98264(18) 0.77971(12) 0.0563(6) Uani d . 1 . . C
  H13A 0.7169 0.9952 0.8218 0.068 Uiso calc R 1 . . H
  C14 0.7361(2) 1.00108(16) 0.71794(13) 0.0478(5) Uani d . 1 . . C
  H14A 0.8078 1.0280 0.7182 0.057 Uiso calc R 1 . . H
  C15 0.68394(17) 0.97928(14) 0.65567(10) 0.0368(4) Uani d . 1 . . C
  H15A 0.7217 0.9905 0.6139 0.044 Uiso calc R 1 . . H
  C31 0.92214(18) 0.81407(19) 0.38827(12) 0.0521(6) Uani d . 1 . . C
  H31A 0.9516 0.8724 0.3779 0.078 Uiso calc R 1 . . H
  H31B 0.9477 0.7726 0.3535 0.078 Uiso calc R 1 . . H
  H31C 0.9492 0.7954 0.4331 0.078 Uiso calc R 1 . . H
  C51 0.50499(19) 0.81183(17) 0.31405(10) 0.0452(5) Uani d . 1 . . C
  H51A 0.5229 0.7955 0.2670 0.068 Uiso calc R 1 . . H
  H51B 0.4680 0.8690 0.3145 0.068 Uiso calc R 1 . . H
  H51C 0.4549 0.7679 0.3339 0.068 Uiso calc R 1 . . H
  C81 0.23295(17) 0.90503(17) 0.51881(13) 0.0442(5) Uani d . 1 . . C
  H81A 0.2001 0.8721 0.5567 0.066 Uiso calc R 1 . . H
  H81B 0.2064 0.8807 0.4755 0.066 Uiso calc R 1 . . H
  H81C 0.2105 0.9665 0.5222 0.066 Uiso calc R 1 . . H
  N1 0.73495(12) 0.83749(11) 0.44553(8) 0.0316(3) Uani d . 1 . . N
  N2 0.62136(13) 0.83753(10) 0.42500(8) 0.0295(3) Uani d . 1 . . N
  N3 0.40850(13) 0.92337(11) 0.58266(9) 0.0348(4) Uani d . 1 . . N
  N4 0.58950(12) 0.88237(11) 0.53781(8) 0.0282(3) Uani d . 1 . . N
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
  Cu1 0.02606(11) 0.04428(15) 0.02545(13) 0.00235(9) -0.00037(8) 0.00186(9)
  Cl1 0.0403(2) 0.0539(3) 0.0341(3) 0.0093(2) 0.00545(19) 0.0107(2)
  Cl2 0.0298(2) 0.0792(4) 0.0471(3) -0.0078(3) -0.0035(2) -0.0021(3)
  C3 0.0355(9) 0.0458(11) 0.0278(9) 0.0054(8) 0.0088(8) 0.0050(8)
  C4 0.0449(11) 0.0511(12) 0.0248(9) 0.0053(9) 0.0065(8) 0.0002(9)
  C5 0.0386(10) 0.0389(10) 0.0236(9) -0.0004(8) -0.0004(7) 0.0000(7)
  C6 0.0290(8) 0.0304(8) 0.0247(8) 0.0004(7) 0.0013(7) 0.0022(7)
  C7 0.0286(8) 0.0389(10) 0.0294(9) -0.0002(7) -0.0020(7) -0.0002(8)
  C8 0.0284(8) 0.0382(10) 0.0323(10) 0.0006(7) 0.0004(7) 0.0015(8)
  C9 0.0305(8) 0.0324(9) 0.0260(8) 0.0020(7) 0.0029(7) -0.0017(7)
  C10 0.0358(9) 0.0360(9) 0.0244(9) 0.0053(7) 0.0011(7) -0.0023(7)
  C11 0.0493(12) 0.0528(13) 0.0330(11) -0.0025(10) 0.0087(9) -0.0046(9)
  C12 0.0818(18) 0.0668(16) 0.0257(10) -0.0018(14) 0.0073(11) -0.0009(11)
  C13 0.0766(17) 0.0598(15) 0.0325(11) 0.0008(13) -0.0136(11) -0.0066(10)
  C14 0.0492(13) 0.0523(13) 0.0419(12) -0.0002(10) -0.0119(10) -0.0059(10)
  C15 0.0368(9) 0.0426(10) 0.0311(10) 0.0035(8) -0.0003(8) -0.0032(8)
  C31 0.0365(11) 0.0822(17) 0.0378(12) 0.0125(11) 0.0109(9) 0.0074(12)
  C51 0.0436(11) 0.0653(14) 0.0269(10) -0.0024(10) -0.0045(8) -0.0068(10)
  C81 0.0298(10) 0.0566(14) 0.0461(13) 0.0012(9) 0.0020(8) -0.0020(10)
  N1 0.0261(7) 0.0437(9) 0.0250(8) 0.0029(6) 0.0019(5) 0.0011(6)
  N2 0.0257(7) 0.0402(8) 0.0225(7) 0.0021(6) 0.0012(6) -0.0015(6)
  N3 0.0302(8) 0.0418(9) 0.0325(8) 0.0028(6) 0.0025(6) -0.0025(7)
  N4 0.0268(7) 0.0344(8) 0.0233(7) 0.0016(6) -0.0003(5) -0.0011(6)
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
  Cu1 N1 . 1.9938(16) ?
  Cu1 N4 . 2.0098(15) ?
  Cu1 Cl2 . 2.1836(6) ?
  Cu1 Cl1 . 2.2307(6) ?
  C3 N1 . 1.334(2) ?
  C3 C4 . 1.393(3) ?
  C3 C31 . 1.487(3) ?
  C4 C5 . 1.365(3) ?
  C4 H4A . 0.9300 ?
  C5 N2 . 1.377(2) ?
  C5 C51 . 1.484(3) ?
  C6 N4 . 1.346(2) ?
  C6 C7 . 1.383(2) ?
  C6 N2 . 1.401(2) ?
  C7 C8 . 1.395(3) ?
  C7 H7A . 0.9300 ?
  C8 N3 . 1.349(3) ?
  C8 C81 . 1.490(3) ?
  C9 N3 . 1.331(2) ?
  C9 N4 . 1.342(2) ?
  C9 C10 . 1.480(3) ?
  C10 C15 . 1.389(3) ?
  C10 C11 . 1.388(3) ?
  C11 C12 . 1.385(3) ?
  C11 H11A . 0.9300 ?
  C12 C13 . 1.377(4) ?
  C12 H12A . 0.9300 ?
  C13 C14 . 1.378(3) ?
  C13 H13A . 0.9300 ?
  C14 C15 . 1.382(3) ?
  C14 H14A . 0.9300 ?
  C15 H15A . 0.9300 ?
  C31 H31A . 0.9600 ?
  C31 H31B . 0.9600 ?
  C31 H31C . 0.9600 ?
  C51 H51A . 0.9600 ?
  C51 H51B . 0.9600 ?
  C51 H51C . 0.9600 ?
  C81 H81A . 0.9600 ?
  C81 H81B . 0.9600 ?
  C81 H81C . 0.9600 ?
  N1 N2 . 1.385(2) ?