data_2014663
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2005
_journal_volume  61
_journal_page_first  o177
_journal_page_last  o180
_publ_section_title
;\
C---Halogen...\p dimer and C---H...\p interactions in
1-(2-bromo-4,5-dimethoxybenzyl)-2-butyl-4-chloro-1<i>H</i>-imidazole-5-\
carboxaldehyde and
2-butyl-4-chloro-1-(6-methyl-1,3-benzodioxol-5-ylmethyl)-1<i>H</i>-imidazole-
5-carboxaldehyde
;
loop_
_publ_author_name
  'Nagaraj, B.'
  'Narasimhamurthy, T.'
  'Yathirajan, H. S.'
  'Nagaraja, P.'
  'Narasegowda, R. S.'
  'Rathore, Ravindranath S.'
_chemical_name_common
;
2-butyl-4-chloro-1-(6-methyl-1,3-benzodioxol-5-ylmethyl)-1H-imidazole-
5-carboxaldehyde
;
_chemical_formula_moiety  'C17 H19 Cl N2 O3'
_chemical_formula_sum  'C17 H19 Cl N2 O3'
_chemical_formula_iupac  'C17 H19 Cl N2 O3'
_chemical_formula_weight  334.79
_chemical_melting_point  385
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x+1/2, y+1/2, -z+1/2'
  '-x, -y, -z'
  'x-1/2, -y-1/2, z-1/2'
_cell_length_a  12.4899(5)
_cell_length_b  9.4887(3)
_cell_length_c  14.1018(5)
_cell_angle_alpha  90.00
_cell_angle_beta  94.3190(10)
_cell_angle_gamma  90.00
_cell_volume  1666.50(10)
_cell_formula_units_Z  4
_cell_measurement_temperature  130(2)
_exptl_crystal_density_diffrn  1.330
_diffrn_ambient_temperature  130(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
  Cl1 0.57999(5) 0.38185(7) 0.59703(4) 0.0745(3) Uani d . 1 . . Cl
  O1 0.82630(14) 0.50150(19) 0.39261(12) 0.0766(5) Uani d . 1 . . O
  O2 0.58305(17) 0.71783(18) -0.01039(12) 0.0800(5) Uani d . 1 . . O
  O3 0.47714(15) 0.68771(19) 0.11624(13) 0.0814(5) Uani d . 1 . . O
  N1 0.52146(14) 0.24137(19) 0.43849(12) 0.0552(5) Uani d . 1 . . N
  N2 0.64549(13) 0.29981(17) 0.34053(11) 0.0474(4) Uani d . 1 . . N
  C1 0.55578(16) 0.2244(2) 0.35181(14) 0.0496(5) Uani d . 1 . . C
  C2 0.67150(16) 0.3713(2) 0.42515(14) 0.0482(5) Uani d . 1 . . C
  C3 0.59277(17) 0.3303(2) 0.48201(14) 0.0509(5) Uani d . 1 . . C
  C4 0.49993(19) 0.1356(3) 0.27625(16) 0.0626(6) Uani d . 1 . . C
  H4A 0.5516 0.0665 0.2536 0.075 Uiso calc R 1 . . H
  H4B 0.4757 0.1965 0.2218 0.075 Uiso calc R 1 . . H
  C5 0.40416(18) 0.0573(2) 0.30956(16) 0.0604(6) Uani d . 1 . . C
  H5A 0.4294 -0.0106 0.3596 0.072 Uiso calc R 1 . . H
  H5B 0.3561 0.1255 0.3383 0.072 Uiso calc R 1 . . H
  C6 0.3411(2) -0.0211(3) 0.2308(2) 0.0849(8) Uani d . 1 . . C
  H6A 0.3881 -0.0933 0.2048 0.102 Uiso calc R 1 . . H
  H6B 0.3200 0.0459 0.1789 0.102 Uiso calc R 1 . . H
  C7 0.2414(3) -0.0924(3) 0.2619(2) 0.1031(11) Uani d . 1 . . C
  H7A 0.2044 -0.1408 0.2074 0.155 Uiso calc R 1 . . H
  H7B 0.1935 -0.0216 0.2864 0.155 Uiso calc R 1 . . H
  H7C 0.2616 -0.1612 0.3119 0.155 Uiso calc R 1 . . H
  C8 0.75959(19) 0.4656(2) 0.44581(17) 0.0605(6) Uani d . 1 . . C
  H8 0.7665 0.5042 0.5081 0.073 Uiso calc R 1 . . H
  C9 0.70788(17) 0.2990(2) 0.25658(14) 0.0538(5) Uani d . 1 . . C
  H9A 0.6983 0.2067 0.2244 0.065 Uiso calc R 1 . . H
  H9B 0.7849 0.3090 0.2776 0.065 Uiso calc R 1 . . H
  C10 0.67716(15) 0.4144(2) 0.18554(13) 0.0449(5) Uani d . 1 . . C
  C11 0.74152(17) 0.4317(2) 0.10945(14) 0.0514(5) Uani d . 1 . . C
  C12 0.7141(2) 0.5334(2) 0.04015(15) 0.0611(6) Uani d . 1 . . C
  H12 0.7574 0.5474 -0.0116 0.073 Uiso calc R 1 . . H
  C13 0.6244(2) 0.6119(2) 0.04838(14) 0.0569(6) Uani d . 1 . . C
  C14 0.56169(17) 0.5946(2) 0.12356(15) 0.0540(5) Uani d . 1 . . C
  C15 0.58636(17) 0.4971(2) 0.19294(14) 0.0511(5) Uani d . 1 . . C
  H15 0.5427 0.4860 0.2448 0.061 Uiso calc R 1 . . H
  C16 0.8396(2) 0.3412(3) 0.10041(19) 0.0737(7) Uani d . 1 . . C
  H16A 0.8766 0.3717 0.0451 0.111 Uiso calc R 1 . . H
  H16B 0.8178 0.2425 0.0923 0.111 Uiso calc R 1 . . H
  H16C 0.8882 0.3507 0.1580 0.111 Uiso calc R 1 . . H
  C17 0.4865(2) 0.7597(3) 0.0286(2) 0.0811(8) Uani d . 1 . . C
  H17A 0.4242 0.7369 -0.0164 0.097 Uiso calc R 1 . . H
  H17B 0.4872 0.8628 0.0395 0.097 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
  Cl1 0.0843(5) 0.0918(5) 0.0485(4) -0.0050(3) 0.0125(3) -0.0107(3)
  O1 0.0709(11) 0.0800(12) 0.0793(11) -0.0178(9) 0.0085(9) 0.0166(9)
  O2 0.1118(15) 0.0665(11) 0.0610(10) 0.0006(10) 0.0024(10) 0.0165(8)
  O3 0.0869(12) 0.0754(12) 0.0820(12) 0.0272(10) 0.0086(9) 0.0176(10)
  N1 0.0558(11) 0.0634(11) 0.0479(10) -0.0041(9) 0.0131(8) 0.0008(9)
  N2 0.0493(10) 0.0494(10) 0.0445(9) 0.0045(8) 0.0097(7) 0.0043(8)
  C1 0.0523(12) 0.0499(12) 0.0472(11) 0.0019(10) 0.0079(9) 0.0022(9)
  C2 0.0505(12) 0.0463(11) 0.0474(11) 0.0029(9) 0.0025(9) 0.0043(9)
  C3 0.0548(12) 0.0535(12) 0.0447(11) 0.0026(10) 0.0064(9) 0.0011(10)
  C4 0.0680(15) 0.0664(15) 0.0538(13) -0.0022(12) 0.0084(11) -0.0055(11)
  C5 0.0617(14) 0.0581(13) 0.0606(13) -0.0003(11) -0.0003(11) -0.0026(11)
  C6 0.093(2) 0.0785(18) 0.0804(17) -0.0088(16) -0.0093(15) -0.0160(15)
  C7 0.104(2) 0.088(2) 0.112(2) -0.0362(19) -0.0307(19) 0.0138(18)
  C8 0.0674(14) 0.0551(13) 0.0584(13) 0.0006(12) 0.0000(11) 0.0102(11)
  C9 0.0549(12) 0.0564(13) 0.0520(12) 0.0084(10) 0.0169(9) 0.0046(10)
  C10 0.0468(11) 0.0466(11) 0.0420(10) -0.0034(9) 0.0081(8) -0.0046(9)
  C11 0.0542(12) 0.0514(12) 0.0500(11) -0.0073(10) 0.0138(9) -0.0087(10)
  C12 0.0785(16) 0.0585(14) 0.0489(12) -0.0126(13) 0.0229(11) -0.0024(11)
  C13 0.0790(16) 0.0478(12) 0.0433(11) -0.0118(12) -0.0002(10) 0.0004(10)
  C14 0.0598(13) 0.0484(12) 0.0532(12) 0.0018(11) 0.0009(10) -0.0015(10)
  C15 0.0540(12) 0.0541(12) 0.0466(11) 0.0015(10) 0.0139(9) 0.0007(10)
  C16 0.0693(16) 0.0729(16) 0.0840(17) 0.0001(13) 0.0389(13) -0.0079(14)
  C17 0.0868(19) 0.0673(16) 0.0851(18) -0.0060(15) -0.0211(15) 0.0197(14)
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
  Cl1 C3 . 1.713(2) ?
  O1 C8 . 1.211(3) ?
  O2 C13 . 1.378(3) ?
  O2 C17 . 1.419(3) ?
  O3 C14 . 1.375(3) ?
  O3 C17 . 1.425(3) ?
  N1 C1 . 1.335(3) ?
  N1 C3 . 1.341(3) ?
  N2 C1 . 1.349(3) ?
  N2 C2 . 1.390(3) ?
  N2 C9 . 1.466(2) ?
  C1 C4 . 1.490(3) ?
  C2 C3 . 1.371(3) ?
  C2 C8 . 1.431(3) ?
  C4 C5 . 1.513(3) ?
  C4 H4A . 0.9900 ?
  C4 H4B . 0.9900 ?
  C5 C6 . 1.509(3) ?
  C5 H5A . 0.9900 ?
  C5 H5B . 0.9900 ?
  C6 C7 . 1.511(4) ?
  C6 H6A . 0.9900 ?
  C6 H6B . 0.9900 ?
  C7 H7A . 0.9800 ?
  C7 H7B . 0.9800 ?
  C7 H7C . 0.9800 ?
  C8 H8 . 0.9500 ?
  C9 C10 . 1.514(3) ?
  C9 H9A . 0.9900 ?
  C9 H9B . 0.9900 ?
  C10 C15 . 1.389(3) ?
  C10 C11 . 1.398(3) ?
  C11 C12 . 1.398(3) ?
  C11 C16 . 1.510(3) ?
  C12 C13 . 1.357(3) ?
  C12 H12 . 0.9500 ?
  C13 C14 . 1.375(3) ?
  C14 C15 . 1.365(3) ?
  C15 H15 . 0.9500 ?
  C16 H16A . 0.9800 ?
  C16 H16B . 0.9800 ?
  C16 H16C . 0.9800 ?
  C17 H17A . 0.9900 ?
  C17 H17B . 0.9900 ?