data_2200920
_journal_name_full  'Acta Crystallographica, Section E'
_journal_year  2002
_journal_volume  58
_journal_page_first  o55
_journal_page_last  o56
_publ_section_title
;
1-(2-Methyl-2,3-dihydroindol-1-ylmethyl)-1H-benzotriazole
;
loop_
_publ_author_name
  'Low, John Nicolson'
  'Cobo, Justo'
  'Nogueras, Manuel'
  "S\'anchez, Adolfo"
  'Abonia, Rodrigo'
  'Albornoz, Andrea'
_chemical_formula_moiety  'C16 H16 N4'
_chemical_formula_sum  'C16 H16 N4'
_chemical_formula_iupac  'C16 H16 N4'
_chemical_formula_weight  264.33
_chemical_melting_point  343K
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'P 21'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, y+1/2, -z'
_cell_length_a  7.5660(3)
_cell_length_b  17.7842(8)
_cell_length_c  10.2284(4)
_cell_angle_alpha  90.00
_cell_angle_beta  104.689(3)
_cell_angle_gamma  90.00
_cell_volume  1331.30(10)
_cell_formula_units_Z  4
_cell_measurement_temperature  120.0(10)
_exptl_crystal_density_diffrn  1.319
_diffrn_ambient_temperature  120.0(10)
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  .8200(5)  .40980(19)  .0108(3)  .0241(8) Uani d . 1 . . N
  N2  .7833(5)  .4746(2)  .0732(3)  .0296(8) Uani d . 1 . . N
  N3  .6998(5)  .5216(2)  -.0177(4)  .0304(9) Uani d . 1 . . N
  C3A  .6820(6)  .4893(2)  -.1430(4)  .0266(10) Uani d . 1 . . C
  C4  .6019(6)  .5174(3)  -.2746(4)  .0312(10) Uani d . 1 . . C
  C5  .6103(6)  .4736(3)  -.3808(4)  .0302(10) Uani d . 1 . . C
  C6  .6900(6)  .4007(3)  -.3617(4)  .0315(10) Uani d . 1 . . C
  C7  .7655(5)  .3720(3)  -.2356(4)  .0264(9) Uani d . 1 . . C
  C7A  .7580(5)  .4175(2)  -.1262(4)  .0246(9) Uani d . 1 . . C
  C11  .9185(5)  .3476(2)  .0945(4)  .0237(9) Uani d . 1 . . C
  N11  .8098(5)  .28369(19)  .1098(3)  .0231(8) Uani d . 1 . . N
  C12  .7561(6)  .2268(2)  -.0007(4)  .0249(10) Uani d . 1 . . C
  C121  .9153(6)  .1854(3)  -.0286(5)  .0315(11) Uani d . 1 . . C
  C13  .6222(6)  .1763(2)  .0528(4)  .0268(10) Uani d . 1 . . C
  C13A  .5441(6)  .2303(2)  .1367(4)  .0239(9) Uani d . 1 . . C
  C14  .3894(6)  .2250(2)  .1846(4)  .0258(9) Uani d . 1 . . C
  C15  .3530(6)  .2829(2)  .2661(4)  .0261(10) Uani d . 1 . . C
  C16  .4702(5)  .3442(2)  .2985(4)  .0244(9) Uani d . 1 . . C
  C17  .6269(5)  .3496(3)  .2504(4)  .0226(9) Uani d . 1 . . C
  C17A  .6615(5)  .2919(2)  .1692(4)  .0217(9) Uani d . 1 . . C
  N21  .9170(4)  -.04286(19)  .4760(3)  .0226(8) Uani d . 1 . . N
  N22  .8702(5)  -.10494(19)  .5390(3)  .0283(9) Uani d . 1 . . N
  N23  .7856(5)  -.1531(2)  .4460(3)  .0296(8) Uani d . 1 . . N
  C23A  .7793(6)  -.1225(2)  .3213(4)  .0260(10) Uani d . 1 . . C
  C24  .7049(6)  -.1514(3)  .1918(4)  .0306(10) Uani d . 1 . . C
  C25  .7165(6)  -.1081(3)  .0831(4)  .0315(11) Uani d . 1 . . C
  C26  .8042(6)  -.0367(3)  .1032(4)  .0285(10) Uani d . 1 . . C
  C27  .8779(6)  -.0076(2)  .2283(4)  .0259(9) Uani d . 1 . . C
  C27A  .8624(5)  -.0515(2)  .3382(4)  .0219(9) Uani d . 1 . . C
  C21 1.0189(5)  .0179(2)  .5600(4)  .0233(9) Uani d . 1 . . C
  N31  .9171(5)  .08521(19)  .5664(3)  .0230(8) Uani d . 1 . . N
  C32  .8749(6)  .1392(3)  .4541(4)  .0303(10) Uani d . 1 . . C
  C321 1.0373(6)  .1710(3)  .4146(5)  .0320(11) Uani d . 1 . . C
  C33  .7579(6)  .1978(2)  .5043(4)  .0277(10) Uani d . 1 . . C
  C33A  .6648(6)  .1512(2)  .5903(4)  .0243(9) Uani d . 1 . . C
  C34  .5104(6)  .1634(3)  .6343(4)  .0309(10) Uani d . 1 . . C
  C35  .4578(6)  .1099(3)  .7158(4)  .0323(11) Uani d . 1 . . C
  C36  .5607(6)  .0457(3)  .7542(4)  .0295(11) Uani d . 1 . . C
  C37  .7183(6)  .0318(2)  .7101(4)  .0263(10) Uani d . 1 . . C
  C37A  .7666(6)  .0847(2)  .6258(4)  .0237(10) Uani d . 1 . . C
  H4  .5446  .5654  -.2876  .037 Uiso calc R 1 . . H
  H5  .5618  .4918  -.4700  .036 Uiso calc R 1 . . H
  H6  .6910  .3711  -.4387  .038 Uiso calc R 1 . . H
  H7  .8201  .3236  -.2233  .032 Uiso calc R 1 . . H
  H11A 1.0175  .3304  .0543  .028 Uiso calc R 1 . . H
  H11B  .9768  .3677  .1855  .028 Uiso calc R 1 . . H
  H12  .6873  .2525  -.0853  .030 Uiso calc R 1 . . H
  H12A  .9966  .2211  -.0573  .047 Uiso calc R 1 . . H
  H12B  .8709  .1484  -.1004  .047 Uiso calc R 1 . . H
  H12C  .9825  .1595  .0536  .047 Uiso calc R 1 . . H
  H13A  .5254  .1555  -.0225  .032 Uiso calc R 1 . . H
  H13B  .6875  .1344  .1084  .032 Uiso calc R 1 . . H
  H14  .3098  .1830  .1626  .031 Uiso calc R 1 . . H
  H15  .2471  .2804  .2999  .031 Uiso calc R 1 . . H
  H16  .4433  .3831  .3542  .029 Uiso calc R 1 . . H
  H17  .7071  .3915  .2725  .027 Uiso calc R 1 . . H
  H24  .6482  -.1994  .1794  .037 Uiso calc R 1 . . H
  H25  .6657  -.1260  -.0060  .038 Uiso calc R 1 . . H
  H26  .8116  -.0082  .0262  .034 Uiso calc R 1 . . H
  H27  .9368  .0400  .2402  .031 Uiso calc R 1 . . H
  H21A 1.0667  -.0014  .6530  .028 Uiso calc R 1 . . H
  H21B 1.1253  .0311  .5248  .028 Uiso calc R 1 . . H
  H32  .7957  .1134  .3734  .036 Uiso calc R 1 . . H
  H32A 1.1096  .2015  .4889  .048 Uiso calc R 1 . . H
  H32B  .9959  .2025  .3340  .048 Uiso calc R 1 . . H
  H32C 1.1127  .1298  .3949  .048 Uiso calc R 1 . . H
  H33A  .8349  .2375  .5583  .033 Uiso calc R 1 . . H
  H33B  .6678  .2214  .4280  .033 Uiso calc R 1 . . H
  H34  .4404  .2079  .6093  .037 Uiso calc R 1 . . H
  H35  .3499  .1176  .7455  .039 Uiso calc R 1 . . H
  H36  .5238  .0102  .8116  .035 Uiso calc R 1 . . H
  H37  .7895  -.0122  .7369  .032 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  .0293(19)  .0195(19)  .0244(17)  -.0006(16)  .0086(15)  .0003(15)
  N2  .037(2)  .018(2)  .0342(19)  -.0003(17)  .0117(17)  -.0030(16)
  N3  .034(2)  .0215(19)  .0358(19)  .0033(17)  .0098(17)  .0030(17)
  C3A  .028(2)  .021(2)  .032(2)  -.004(2)  .0093(19)  -.0007(19)
  C4  .027(2)  .027(2)  .038(2)  .000(2)  .006(2)  .007(2)
  C5  .025(2)  .035(3)  .029(2)  -.001(2)  .0044(18)  .007(2)
  C6  .033(3)  .032(3)  .030(2)  .000(2)  .0078(19)  -.001(2)
  C7  .027(2)  .022(2)  .030(2)  .0006(19)  .0089(18)  -.0002(19)
  C7A  .025(2)  .019(2)  .030(2)  -.0011(18)  .0086(18)  .0027(19)
  C11  .025(2)  .019(2)  .026(2)  -.0013(19)  .0051(17)  .0003(18)
  N11  .031(2)  .0168(18)  .0226(17)  -.0044(16)  .0081(15)  .0001(14)
  C12  .032(2)  .018(2)  .024(2)  -.0028(19)  .0071(19)  -.0012(17)
  C121  .026(3)  .027(3)  .041(3)  .003(2)  .008(2)  -.007(2)
  C13  .032(3)  .018(2)  .031(2)  -.0037(19)  .0073(19)  -.0052(17)
  C13A  .024(2)  .018(2)  .027(2)  -.0014(18)  .0017(17)  -.0013(18)
  C14  .026(2)  .019(2)  .031(2)  -.0062(19)  .0049(18)  .0051(18)
  C15  .022(2)  .026(2)  .031(2)  .0000(19)  .0068(18)  .0074(19)
  C16  .028(2)  .020(2)  .026(2)  .008(2)  .0076(17)  .0047(17)
  C17  .025(2)  .017(2)  .023(2)  -.0019(19)  .0017(17)  .0022(17)
  C17A  .021(2)  .020(2)  .0211(19)  .0019(19)  .0000(16)  .0049(17)
  N21  .0282(19)  .0139(18)  .0260(17)  .0031(15)  .0077(15)  .0008(14)
  N22  .039(2)  .0160(19)  .0315(19)  .0008(17)  .0119(17)  .0037(16)
  N23  .036(2)  .0187(18)  .036(2)  -.0008(18)  .0125(16)  -.0008(17)
  C23A  .025(2)  .021(2)  .034(2)  -.0003(19)  .0113(18)  -.0035(19)
  C24  .027(2)  .024(2)  .043(3)  -.003(2)  .0117(19)  -.010(2)
  C25  .029(3)  .034(3)  .030(2)  .005(2)  .0047(19)  -.006(2)
  C26  .027(2)  .032(3)  .026(2)  .002(2)  .0066(18)  .000(2)
  C27  .027(2)  .018(2)  .033(2)  .0042(19)  .0080(19)  .0001(18)
  C27A  .024(2)  .017(2)  .026(2)  .0017(18)  .0095(18)  -.0027(17)
  C21  .022(2)  .020(2)  .027(2)  .0009(19)  .0063(18)  -.0019(18)
  N31  .027(2)  .0151(18)  .0285(18)  .0031(15)  .0107(16)  .0019(14)
  C32  .035(3)  .022(2)  .032(2)  .005(2)  .005(2)  .0054(19)
  C321  .032(3)  .024(2)  .040(2)  -.004(2)  .008(2)  .0054(19)
  C33  .033(3)  .017(2)  .032(2)  .0057(19)  .0062(19)  .0029(18)
  C33A  .022(2)  .025(2)  .0216(19)  .0027(19)  -.0015(17)  -.0040(18)
  C34  .033(3)  .026(2)  .029(2)  .008(2)  -.001(2)  -.0040(19)
  C35  .030(3)  .040(3)  .027(2)  -.003(2)  .009(2)  -.012(2)
  C36  .034(3)  .027(3)  .030(2)  -.006(2)  .011(2)  -.008(2)
  C37  .039(3)  .014(2)  .025(2)  -.0002(19)  .0071(19)  -.0031(17)
  C37A  .031(2)  .021(2)  .0180(19)  -.0012(19)  .0036(18)  -.0018(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
  N1 C7A . 1.367(5) ?
  N1 N2 . 1.380(5) ?
  N1 C11 . 1.479(5) ?
  N2 N3 . 1.290(5) ?
  N3 C3A . 1.380(5) ?
  C3A C7A . 1.393(6) ?
  C3A C4 . 1.420(6) ?
  C4 C5 . 1.352(6) ?
  C4 H4 .  .9500 ?
  C5 C6 . 1.421(6) ?
  C5 H5 .  .9500 ?
  C6 C7 . 1.370(6) ?
  C6 H6 .  .9500 ?
  C7 C7A . 1.393(6) ?
  C7 H7 .  .9500 ?
  C11 N11 . 1.435(5) ?
  C11 H11A .  .9900 ?
  C11 H11B .  .9900 ?
  N11 C17A . 1.413(5) ?
  N11 C12 . 1.494(5) ?
  C12 C121 . 1.500(6) ?
  C12 C13 . 1.553(6) ?
  C12 H12 . 1.0000 ?
  C121 H12A .  .9800 ?
  C121 H12B .  .9800 ?
  C121 H12C .  .9800 ?
  C13 C13A . 1.505(6) ?
  C13 H13A .  .9900 ?
  C13 H13B .  .9900 ?
  C13A C14 . 1.382(6) ?
  C13A C17A . 1.396(6) ?
  C14 C15 . 1.395(6) ?
  C14 H14 .  .9500 ?
  C15 C16 . 1.392(6) ?
  C15 H15 .  .9500 ?
  C16 C17 . 1.398(5) ?
  C16 H16 .  .9500 ?
  C17 C17A . 1.387(6) ?
  C17 H17 .  .9500 ?
  N21 N22 . 1.369(5) ?
  N21 C27A . 1.373(5) ?
  N21 C21 . 1.471(5) ?
  N22 N23 . 1.318(5) ?
  N23 C23A . 1.376(5) ?
  C23A C24 . 1.400(6) ?
  C23A C27A . 1.400(6) ?
  C24 C25 . 1.372(6) ?
  C24 H24 .  .9500 ?
  C25 C26 . 1.424(7) ?
  C25 H25 .  .9500 ?
  C26 C27 . 1.361(6) ?
  C26 H26 .  .9500 ?
  C27 C27A . 1.399(6) ?
  C27 H27 .  .9500 ?
  C21 N31 . 1.434(5) ?
  C21 H21A .  .9900 ?
  C21 H21B .  .9900 ?
  N31 C37A . 1.420(5) ?
  N31 C32 . 1.469(5) ?
  C32 C321 . 1.499(6) ?
  C32 C33 . 1.537(6) ?
  C32 H32 . 1.0000 ?
  C321 H32A .  .9800 ?
  C321 H32B .  .9800 ?
  C321 H32C .  .9800 ?
  C33 C33A . 1.506(6) ?
  C33 H33A .  .9900 ?
  C33 H33B .  .9900 ?
  C33A C34 . 1.372(6) ?
  C33A C37A . 1.408(6) ?
  C34 C35 . 1.388(6) ?
  C34 H34 .  .9500 ?
  C35 C36 . 1.383(7) ?
  C35 H35 .  .9500 ?
  C36 C37 . 1.400(6) ?
  C36 H36 .  .9500 ?
  C37 C37A . 1.386(6) ?
  C37 H37 .  .9500 ?