data_2006422
_journal_name_full  'Acta Crystallographica'
_journal_year  1997
_journal_volume  C53
_journal_page_first  1116
_journal_page_last  1117
_publ_section_title
;
4-Hydroxy-2,6-bis[(4-methylpiperazinyl)methyl]benzonitrile Monohydrate
;
loop_
_publ_author_name
 'Gunasekaran, K.'
 'Shanmuga Sundara Raj, S.'
 'Velmurugan, D.'
 'Rajendran, T. M.'
 'Kandaswamy, M.'
_chemical_formula_moiety  'C19 H29 N5 O.H2 O'
_chemical_formula_sum  'C19 H31 N5 O2'
_chemical_formula_weight  361.49
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
loop_
_symmetry_equiv_pos_as_xyz
 'x,y,z'
 'x,-y,1/2+z'
 '-x,-y,-z'
 '-x,y,1/2-z'
 '1/2+x,1/2+y,z'
 '1/2+x,1/2-y,1/2+z'
 '1/2-x,1/2-y,-z'
 '1/2-x,1/2+y,1/2-z'
_cell_length_a  34.250(3)
_cell_length_b  9.1340(10)
_cell_length_c  13.8190(10)
_cell_angle_alpha  90
_cell_angle_beta  112.70(10)
_cell_angle_gamma  90
_cell_volume  3988.3(7)
_cell_formula_units_Z  8
_cell_measurement_temperature  298
_exptl_crystal_density_diffrn  1.20
_exptl_crystal_density_meas  1.251
_refine_ls_R_factor_obs   .06
_refine_ls_wR_factor_obs   .082
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_u_iso_or_equiv
 C1 .12290(10)
 .1092(2) .9907(2) 3.41(6)
 C2 .15090(10)
 .1031(2) .9398(2) 3.35(6)
 C3 .13700(10)
 .1399(2) .8345(2) 3.49(5)
 C4 .09480(10)
 .1832(2) .7811(2) 3.68(5)
 C5 .06720(10)
 .1906(3) .8333(2) 3.92(6)
 C6 .08060(10)
 .1535(3) .9374(2) 3.72(6)
 C7 .04910(10)
 .1529(3) .9907(2) 4.50(7)
 N8 .06930(10)
 .1986(2) 1.10180(10)
  3.64(6)
 C9 .08010(10)
 .3560(3) 1.1118(2) 4.28(6)
 C10 .10260(10)
  .3943(3) 1.2269(2) 4.22(6)
 N11 .07560(10)
  .3628(2) 1.28440(10)
   4.16(5)
 C12 .06380(10)
  .2069(3) 1.2727(2) 4.36(8)
 C13 .04120(10)
  .1679(3) 1.1574(2) 4.18(7)
 C14 .09780(10)
  .4000(3) 1.3952(2) 5.55(9)
 C15 .19630(10)
  .0565(3) 1.0030(2) 3.79(6)
 N16 .22080(10)
  .0357(2) .93760(10)
  3.42(6)
 C17 .26640(10)
  .0432(3) 1.0014(2) 3.90(6)
 C18 .29120(10)
  .0231(3) .9322(2) 4.58(7)
 N19 .28180(10)
  -.1192(3) .8812(2) 4.95(7)
 C20 .23650(10)
  -.1276(3) .8165(2) 5.14(9)
 C21 .21080(10)
  -.1071(3) .8841(2) 4.32(5)
 C22 .30690(10)
  -.1452(5) .8173(3) 7.51(13)
 O23 .13790(10)
  .0751(2) 1.09470(10)
   4.38(5)
 C24 .07930(10)
  .2145(2) .6713(2) 4.19(6)
 N25 .06570(10)
  .2371(3) .5825(2) 6.34(9)
 OW .5000 .0432(3) .2500 9.92(14)
 H3 .1570(10)
   .144(4) .792(2) .055(9)
 H5 .0340(10)
   .232(4) .788(3) .071(9)
 H71 .0250(10)
 .224(4) .951(3) .065(9)
 H72 .0380(10)
 .039(4) .988(2) .079(9)
 H91 .1020(10)
 .381(4) 1.071(3) .065(9)
 H92 .0500(10)
 .428(4) 1.079(2) .080(9)
 H101 .1120(10)
  .501(4) 1.241(3) .063(9)
 H102 .1360(10)
  .340(4) 1.266(2) .078(9)
 H121 .0460(10)
  .181(4) 1.319(3) .056(9)
 H122 .0940(10)
  .140(4) 1.307(2) .067(9)
 H131 .0130(10)
  .227(4) 1.123(3) .063(9)
 H132 .0370(10)
  .052(4) 1.151(2) .078(9)
 H141 .1040(10)
  .512(4) 1.399(2) .084(9)
 H142 .0790(10)
  .375(4) 1.431(2) .062(9)
 H143 .1250(10)
  .321(4) 1.429(3) .076(9)
 H151 .1970(10)
  -.039(4) 1.050(3) .072(9)
 H152 .2120(10)
  .133(4) 1.061(3) .064(9)
 H171 .2780(10)
  -.038(4) 1.063(3) .077(9)
 H172 .2750(10)
  .138(4) 1.041(2) .054(9)
 H181 .3240(10)
  .032(4) .978(3) .075(9)
 H182 .2830(10)
  .111(4) .872(3) .056(9)
 H201 .2280(10)
  -.042(4) .760(2) .075(10)
 H202 .2280(10)
  -.230(4) .781(3) .076(9)
 H211 .1760(10)
  -.108(4) .832(3) .072(10)
 H212 .2170(10)
  -.200(4) .945(2) .072(10)
 H221 .3390(10)
  -.135(4) .868(2) .091(9)
 H222 .3000(10)
  -.256(4) .784(3) .093(9)
 H223 .3010(10)
  -.063(4) .755(3) .118(9)
 H23 .1180(10)
 .102(4) 1.135(2) .085(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
 C1 C2 . . 1.392(5) yes
 C1 C6 . . 1.408(4) yes
 C1 O23 . . 1.363(3) yes
 C2 C3 . . 1.387(4) yes
 C2 C15 . . 1.521(4) yes
 C3 C4 . . 1.402(4) yes
 C4 C5 . . 1.395(5) yes
 C4 C24 . . 1.430(4) yes
 C5 C6 . . 1.373(4) yes
 C6 C7 . . 1.523(5) yes
 C7 N8 . . 1.480(3) yes
 N8 C9 . . 1.478(3) yes
 N8 C13 . . 1.472(5) yes
 C9 C10 . . 1.517(4) yes
 C10 N11 . . 1.462(5) yes
 N11 C12 . . 1.472(3) yes
 N11 C14 . . 1.463(3) yes
 C12 C13 . . 1.521(4) yes
 C15 N16 . . 1.464(5) yes
 N16 C17 . . 1.469(4) yes
 N16 C21 . . 1.473(3) yes
 C17 C18 . . 1.515(5) yes
 C18 N19 . . 1.454(4) yes
 N19 C20 . . 1.464(4) yes
 N19 C22 . . 1.470(6) yes
 C20 C21 . . 1.522(5) yes
 C24 N25 . . 1.151(4) yes
 C3 H3 . . 1.06(4) no
 C5 H5 . . 1.13(3) no
 C7 H71 . . 1.03(3) no
 C7 H72 . . 1.10(4) no
 C9 H91 . . 1.12(4) no
 C9 H92 . . 1.16(3) no
 C10 H101 . . 1.02(4) no
 C10 H102 . . 1.17(3) no
 C12 H121 . . 1.07(4) no
 C12 H122 . . 1.14(3) no
 C13 H131 . . 1.05(3) no
 C13 H132 . . 1.07(4) no
 C14 H141 . . 1.04(4) no
 C14 H142 . . .98(4) no
 C14 H143 . . 1.13(3) no
 C15 H151 . . 1.08(4) no
 C15 H152 . . 1.04(3) no
 C17 H171 . . 1.08(4) no
 C17 H172 . . 1.01(3) no
 C18 H181 . . 1.06(3) no
 C18 H182 . . 1.11(4) no
 C20 H201 . . 1.06(3) no
 C20 H202 . . 1.04(4) no
 C21 H211 . . 1.13(3) no
 C21 H212 . . 1.16(3) no
 C22 H221 . . 1.06(3) no
 C22 H222 . . 1.10(4) no
 C22 H223 . . 1.10(4) no
 O23 H23 . . 1.06(4) no