data_2013789
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2004
_journal_volume  60
_journal_page_first  o149
_journal_page_last  o151
_publ_section_title
;
tert-Butyl 5-methoxy-3-pentylindole-1-carboxylate
;
loop_
_publ_author_name
  'Gallagher, John F.'
  'Coleman, Claire M.'
  'O'Shea, Donal F.'
_chemical_formula_moiety  'C19 H27 N O3'
_chemical_formula_sum  'C19 H27 N O3'
_chemical_formula_iupac  'C19 H27 N O3'
_chemical_formula_weight  317.42
_chemical_melting_point  328
_symmetry_cell_setting  Triclinic
_symmetry_space_group_name_H-M  'P -1'
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, -y, -z'
_cell_length_a  8.9414(6)
_cell_length_b  8.9955(6)
_cell_length_c  11.7433(6)
_cell_angle_alpha  105.001(4)
_cell_angle_beta  93.265(6)
_cell_angle_gamma  98.902(6)
_cell_volume  896.69(10)
_cell_formula_units_Z  2
_cell_measurement_temperature  294.0(10)
_exptl_crystal_density_diffrn  1.176
_diffrn_ambient_temperature  294.0(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
  O1 0.18351(13) 0.57366(14) 0.70809(10) 0.0684(3) Uani d . 1 . . O
  O2 0.38764(12) 0.57975(12) 0.83449(9) 0.0532(3) Uani d . 1 . . O
  O3 0.25088(13) 0.14710(15) 0.16841(10) 0.0673(3) Uani d . 1 . . O
  N1 0.37007(13) 0.43482(13) 0.64714(10) 0.0455(3) Uani d . 1 . . N
  C1 0.67422(16) 0.20729(17) 0.54329(13) 0.0497(3) Uani d . 1 . . C
  C2 0.78016(17) 0.22680(18) 0.65333(13) 0.0518(4) Uani d . 1 . . C
  C3 0.91578(16) 0.14424(17) 0.62986(13) 0.0490(3) Uani d . 1 . . C
  C4 1.02222(19) 0.1643(2) 0.73931(14) 0.0601(4) Uani d . 1 . . C
  C5 1.1590(2) 0.0842(2) 0.71528(17) 0.0708(5) Uani d . 1 . . C
  C6 0.30237(17) 0.53506(16) 0.73022(13) 0.0487(3) Uani d . 1 . . C
  C7 0.33847(18) 0.68863(17) 0.93773(13) 0.0538(4) Uani d . 1 . . C
  C8 0.4711(2) 0.7175(2) 1.03145(15) 0.0727(5) Uani d . 1 . . C
  C9 0.3223(2) 0.8400(2) 0.90901(16) 0.0707(5) Uani d . 1 . . C
  C10 0.1937(2) 0.6085(2) 0.97243(18) 0.0834(6) Uani d . 1 . . C
  C11 0.31383(15) 0.37091(15) 0.52707(12) 0.0430(3) Uani d . 1 . . C
  C12 0.41810(15) 0.27905(15) 0.47337(12) 0.0422(3) Uani d . 1 . . C
  C13 0.39325(16) 0.20448(16) 0.35256(12) 0.0479(3) Uani d . 1 . . C
  C14 0.26678(16) 0.22288(17) 0.28829(13) 0.0498(3) Uani d . 1 . . C
  C15 0.16288(16) 0.31148(17) 0.34293(14) 0.0521(4) Uani d . 1 . . C
  C16 0.18555(16) 0.38630(17) 0.46320(13) 0.0496(3) Uani d . 1 . . C
  C1A 0.50678(15) 0.38203(16) 0.66506(12) 0.0461(3) Uani d . 1 . . C
  C2A 0.53905(15) 0.28740(16) 0.56361(12) 0.0442(3) Uani d . 1 . . C
  C31 0.1372(2) 0.1832(3) 0.09702(16) 0.0829(6) Uani d . 1 . . C
  H1A 0.7318 0.2473 0.4867 0.060 Uiso calc R 1 . . H
  H1B 0.6381 0.0965 0.5078 0.060 Uiso calc R 1 . . H
  H2A 0.7231 0.1866 0.7100 0.062 Uiso calc R 1 . . H
  H2B 0.8170 0.3374 0.6889 0.062 Uiso calc R 1 . . H
  H3A 0.8788 0.0336 0.5947 0.059 Uiso calc R 1 . . H
  H3B 0.9724 0.1840 0.5727 0.059 Uiso calc R 1 . . H
  H4A 0.9661 0.1227 0.7959 0.072 Uiso calc R 1 . . H
  H4B 1.0577 0.2750 0.7753 0.072 Uiso calc R 1 . . H
  H5A 1.1251 -0.0262 0.6825 0.106 Uiso calc R 1 . . H
  H5B 1.2224 0.1026 0.7881 0.106 Uiso calc R 1 . . H
  H5C 1.2160 0.1254 0.6601 0.106 Uiso calc R 1 . . H
  H8A 0.4819 0.6210 1.0491 0.109 Uiso calc R 1 . . H
  H8B 0.4529 0.7917 1.1020 0.109 Uiso calc R 1 . . H
  H8C 0.5628 0.7581 1.0027 0.109 Uiso calc R 1 . . H
  H9A 0.4152 0.8815 0.8823 0.106 Uiso calc R 1 . . H
  H9B 0.3011 0.9139 0.9787 0.106 Uiso calc R 1 . . H
  H9C 0.2403 0.8209 0.8478 0.106 Uiso calc R 1 . . H
  H10A 0.1134 0.5891 0.9098 0.125 Uiso calc R 1 . . H
  H10B 0.1661 0.6745 1.0435 0.125 Uiso calc R 1 . . H
  H10C 0.2095 0.5111 0.9860 0.125 Uiso calc R 1 . . H
  H13 0.4608 0.1432 0.3158 0.058 Uiso calc R 1 . . H
  H15 0.0773 0.3205 0.2981 0.063 Uiso calc R 1 . . H
  H16 0.1162 0.4452 0.4998 0.060 Uiso calc R 1 . . H
  H1A1 0.5669 0.4086 0.7371 0.055 Uiso calc R 1 . . H
  H31A 0.0389 0.1477 0.1188 0.124 Uiso calc R 1 . . H
  H31B 0.1436 0.1322 0.0153 0.124 Uiso calc R 1 . . H
  H31C 0.1517 0.2942 0.1083 0.124 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
  O1 0.0610(7) 0.0837(8) 0.0620(7) 0.0416(6) 0.0078(5) 0.0050(6)
  O2 0.0623(6) 0.0568(6) 0.0441(6) 0.0302(5) 0.0112(5) 0.0074(4)
  O3 0.0660(7) 0.0849(8) 0.0471(6) 0.0251(6) -0.0019(5) 0.0055(5)
  N1 0.0458(6) 0.0501(6) 0.0436(6) 0.0199(5) 0.0085(5) 0.0105(5)
  C1 0.0482(8) 0.0571(8) 0.0477(8) 0.0238(6) 0.0096(6) 0.0117(6)
  C2 0.0517(8) 0.0563(8) 0.0503(8) 0.0230(7) 0.0076(6) 0.0112(6)
  C3 0.0461(7) 0.0553(8) 0.0498(8) 0.0188(6) 0.0075(6) 0.0151(6)
  C4 0.0589(9) 0.0654(10) 0.0558(9) 0.0215(8) 0.0004(7) 0.0111(7)
  C5 0.0579(10) 0.0847(12) 0.0751(12) 0.0270(9) -0.0025(8) 0.0247(10)
  C6 0.0517(8) 0.0485(7) 0.0497(8) 0.0200(6) 0.0118(6) 0.0121(6)
  C7 0.0653(9) 0.0509(8) 0.0485(8) 0.0256(7) 0.0179(7) 0.0076(6)
  C8 0.0936(13) 0.0735(11) 0.0513(9) 0.0357(10) 0.0048(9) 0.0059(8)
  C9 0.0901(13) 0.0541(9) 0.0706(11) 0.0311(9) 0.0104(9) 0.0106(8)
  C10 0.0931(14) 0.0822(13) 0.0733(12) 0.0135(11) 0.0406(11) 0.0124(10)
  C11 0.0431(7) 0.0436(7) 0.0457(7) 0.0125(6) 0.0103(6) 0.0138(6)
  C12 0.0402(7) 0.0444(7) 0.0460(7) 0.0126(5) 0.0096(6) 0.0150(6)
  C13 0.0468(7) 0.0511(8) 0.0480(8) 0.0159(6) 0.0108(6) 0.0116(6)
  C14 0.0486(8) 0.0531(8) 0.0464(8) 0.0089(6) 0.0043(6) 0.0116(6)
  C15 0.0433(7) 0.0580(9) 0.0561(9) 0.0125(6) 0.0001(6) 0.0164(7)
  C16 0.0438(7) 0.0523(8) 0.0564(9) 0.0170(6) 0.0103(6) 0.0148(7)
  C1A 0.0462(7) 0.0516(8) 0.0450(7) 0.0194(6) 0.0078(6) 0.0143(6)
  C2A 0.0445(7) 0.0471(7) 0.0453(7) 0.0160(6) 0.0096(6) 0.0144(6)
  C31 0.0771(12) 0.1139(16) 0.0556(11) 0.0325(11) -0.0078(9) 0.0129(10)
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
  O1 C6 . 1.2029(17) yes
  O2 C6 . 1.3365(18) yes
  O2 C7 . 1.4838(16) yes
  O3 C14 . 1.3846(18) yes
  O3 C31 . 1.410(2) yes
  N1 C6 . 1.3829(17) yes
  N1 C11 . 1.4076(18) yes
  N1 C1A . 1.4022(16) yes
  C1 C2A . 1.5001(18) yes
  C1A C2A . 1.3481(19) yes
  C1 C2 . 1.513(2) no
  C2 C3 . 1.5195(19) no
  C3 C4 . 1.509(2) no
  C4 C5 . 1.517(2) no
  C7 C8 . 1.515(2) no
  C7 C9 . 1.511(2) no
  C7 C10 . 1.512(2) no
  C11 C12 . 1.4090(18) yes
  C11 C16 . 1.3792(19) no
  C12 C2A . 1.4496(19) yes
  C12 C13 . 1.392(2) no
  C13 C14 . 1.379(2) no
  C14 C15 . 1.394(2) no
  C15 C16 . 1.386(2) no
  C1 H1A . 0.9700 ?
  C1 H1B . 0.9700 ?
  C2 H2A . 0.9700 ?
  C2 H2B . 0.9700 ?
  C3 H3A . 0.9700 ?
  C3 H3B . 0.9700 ?
  C4 H4A . 0.9700 ?
  C4 H4B . 0.9700 ?
  C5 H5A . 0.9600 ?
  C5 H5B . 0.9600 ?
  C5 H5C . 0.9600 ?
  C8 H8A . 0.9600 ?
  C8 H8B . 0.9600 ?
  C8 H8C . 0.9600 ?
  C9 H9A . 0.9600 ?
  C9 H9B . 0.9600 ?
  C9 H9C . 0.9600 ?
  C10 H10A . 0.9600 ?
  C10 H10B . 0.9600 ?
  C10 H10C . 0.9600 ?
  C13 H13 . 0.9300 ?
  C15 H15 . 0.9300 ?
  C16 H16 . 0.9300 ?
  C1A H1A1 . 0.9300 ?
  C31 H31A . 0.9600 ?
  C31 H31B . 0.9600 ?
  C31 H31C . 0.9600 ?