#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/05/4020561.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4020561
loop_
_publ_author_name
'Jonathan P. May'
'Pierre Fournier'
'Jonathan Pellicelli'
'Brian O. Patrick'
'David M. Perrin'
_publ_section_title
;
 High Yielding Synthesis of 3a-Hydroxypyrrolo[2,3-b]indoline
 Dipeptide Methyl Esters: Synthons for Expedient
 Introduction of the Hydroxypyrroloindoline Moiety into Larger
 Peptide-Based Natural Products and
 for the Creation of Tryptathionine Bridges.
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8424
_journal_page_last               8430
_journal_paper_doi               10.1021/jo051105t
_journal_volume                  70
_journal_year                    2005
_chemical_formula_sum            'C36 H35 N3 O4'
_chemical_formula_weight         573.67
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.2750(6)
_cell_length_b                   16.3610(10)
_cell_length_c                   17.4740(10)
_cell_measurement_temperature    173(2)
_cell_volume                     2937.5(3)
_diffrn_ambient_temperature      173(2)
_exptl_crystal_density_diffrn    1.297
_cod_database_code               4020561
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C2 C 0.49247(14) 0.17597(9) 0.70009(8) 0.0187(3) Uani 1 1 d . . .
H2 H 0.4166 0.2123 0.7114 0.022 Uiso 1 1 calc R . .
C3 C 0.60942(14) 0.22630(9) 0.67267(8) 0.0221(3) Uani 1 1 d . . .
H3A H 0.6082 0.2818 0.6953 0.027 Uiso 1 1 calc R . .
H3B H 0.6098 0.2311 0.6162 0.027 Uiso 1 1 calc R . .
C3A C 0.72833(15) 0.17758(9) 0.70086(8) 0.0223(3) Uani 1 1 d . . .
C4 C 0.93650(15) 0.26814(9) 0.68320(10) 0.0292(4) Uani 1 1 d . . .
H4 H 0.9344 0.2665 0.6289 0.035 Uiso 1 1 calc R . .
C4A C 0.84207(14) 0.22883(9) 0.72553(9) 0.0233(3) Uani 1 1 d . . .
C5 C 1.03438(15) 0.31006(10) 0.72100(11) 0.0336(4) Uani 1 1 d . . .
H5 H 1.0994 0.3378 0.6923 0.040 Uiso 1 1 calc R . .
C6 C 1.03830(16) 0.31197(10) 0.80032(11) 0.0330(4) Uani 1 1 d . . .
H6 H 1.1079 0.3393 0.8253 0.040 Uiso 1 1 calc R . .
C7 C 0.94171(15) 0.27440(10) 0.84395(10) 0.0296(4) Uani 1 1 d . . .
H7 H 0.9435 0.2765 0.8983 0.035 Uiso 1 1 calc R . .
C7A C 0.84291(14) 0.23379(9) 0.80546(9) 0.0228(3) Uani 1 1 d . . .
C8A C 0.67933(14) 0.14029(9) 0.77695(8) 0.0202(3) Uani 1 1 d . . .
H8A H 0.7150 0.0839 0.7836 0.024 Uiso 1 1 calc R . .
C9 C 0.44816(14) 0.11151(8) 0.83022(8) 0.0180(3) Uani 1 1 d . . .
C10 C 0.32737(14) 0.07092(9) 0.79121(8) 0.0197(3) Uani 1 1 d . . .
C11 C 0.31935(16) -0.01232(10) 0.77566(10) 0.0300(4) Uani 1 1 d . . .
H11 H 0.3870 -0.0475 0.7926 0.036 Uiso 1 1 calc R . .
C12 C 0.21490(18) -0.04491(10) 0.73597(11) 0.0392(4) Uani 1 1 d . . .
H12 H 0.2119 -0.1020 0.7260 0.047 Uiso 1 1 calc R . .
C13 C 0.11537(17) 0.00453(10) 0.71083(10) 0.0351(4) Uani 1 1 d . . .
H13 H 0.0449 -0.0178 0.6825 0.042 Uiso 1 1 calc R . .
C14 C 0.11942(15) 0.08679(10) 0.72724(9) 0.0293(4) Uani 1 1 d . . .
H14 H 0.0503 0.1214 0.7113 0.035 Uiso 1 1 calc R . .
C15 C 0.22398(14) 0.11916(9) 0.76695(9) 0.0238(3) Uani 1 1 d . . .
H15 H 0.2251 0.1760 0.7779 0.029 Uiso 1 1 calc R . .
C16 C 0.39746(14) 0.18564(9) 0.87726(8) 0.0210(3) Uani 1 1 d . . .
C17 C 0.29274(15) 0.17494(10) 0.92763(9) 0.0270(3) Uani 1 1 d . . .
H17 H 0.2565 0.1220 0.9344 0.032 Uiso 1 1 calc R . .
C18 C 0.24165(17) 0.24034(11) 0.96747(9) 0.0340(4) Uani 1 1 d . . .
H18 H 0.1708 0.2322 1.0016 0.041 Uiso 1 1 calc R . .
C19 C 0.29324(17) 0.31757(11) 0.95785(10) 0.0365(4) Uani 1 1 d . . .
H19 H 0.2576 0.3625 0.9851 0.044 Uiso 1 1 calc R . .
C20 C 0.39659(18) 0.32957(10) 0.90862(10) 0.0334(4) Uani 1 1 d . . .
H20 H 0.4323 0.3827 0.9021 0.040 Uiso 1 1 calc R . .
C21 C 0.44840(16) 0.26329(9) 0.86840(9) 0.0249(3) Uani 1 1 d . . .
H21 H 0.5195 0.2717 0.8345 0.030 Uiso 1 1 calc R . .
C22 C 0.52022(14) 0.04938(9) 0.88162(8) 0.0196(3) Uani 1 1 d . . .
C23 C 0.52279(15) 0.05486(9) 0.96119(9) 0.0240(3) Uani 1 1 d . . .
H23 H 0.4814 0.0996 0.9859 0.029 Uiso 1 1 calc R . .
C24 C 0.58539(16) -0.00453(10) 1.00473(9) 0.0300(4) Uani 1 1 d . . .
H24 H 0.5858 0.0001 1.0589 0.036 Uiso 1 1 calc R . .
C25 C 0.64664(16) -0.06972(10) 0.97062(10) 0.0315(4) Uani 1 1 d . . .
H25 H 0.6879 -0.1105 1.0008 0.038 Uiso 1 1 calc R . .
C26 C 0.64719(16) -0.07504(10) 0.89154(10) 0.0292(4) Uani 1 1 d . . .
H26 H 0.6901 -0.1194 0.8672 0.035 Uiso 1 1 calc R . .
C27 C 0.58566(14) -0.01622(9) 0.84779(9) 0.0226(3) Uani 1 1 d . . .
H27 H 0.5879 -0.0205 0.7936 0.027 Uiso 1 1 calc R . .
C28 C 0.45674(15) 0.11240(8) 0.63841(8) 0.0210(3) Uani 1 1 d . . .
C30 C 0.33039(15) 0.07369(9) 0.52712(9) 0.0242(3) Uani 1 1 d . . .
H30 H 0.2961 0.0211 0.5481 0.029 Uiso 1 1 calc R . .
C31 C 0.22404(16) 0.11817(11) 0.48104(10) 0.0322(4) Uani 1 1 d . . .
H31A H 0.2625 0.1489 0.4378 0.039 Uiso 1 1 calc R . .
H31B H 0.1595 0.0788 0.4607 0.039 Uiso 1 1 calc R . .
C32 C 0.16156(17) 0.17572(11) 0.53812(10) 0.0374(4) Uani 1 1 d . . .
H32A H 0.0954 0.1471 0.5694 0.045 Uiso 1 1 calc R . .
H32B H 0.1202 0.2227 0.5120 0.045 Uiso 1 1 calc R . .
C33 C 0.27731(17) 0.20349(10) 0.58748(9) 0.0286(3) Uani 1 1 d . . .
H33A H 0.3231 0.2503 0.5637 0.034 Uiso 1 1 calc R . .
H33B H 0.2486 0.2191 0.6396 0.034 Uiso 1 1 calc R . .
C34 C 0.44891(15) 0.05828(9) 0.47787(8) 0.0238(3) Uani 1 1 d . . .
C35 C 0.54872(19) -0.03824(12) 0.39768(12) 0.0417(5) Uani 1 1 d . . .
H35A H 0.5449 -0.0016 0.3534 0.063 Uiso 1 1 calc R . .
H35B H 0.5382 -0.0949 0.3806 0.063 Uiso 1 1 calc R . .
H35C H 0.6330 -0.0321 0.4233 0.063 Uiso 1 1 calc R . .
N1 N 0.53946(11) 0.13731(7) 0.76958(7) 0.0189(2) Uani 1 1 d . . .
N8 N 0.73320(13) 0.19529(8) 0.83612(8) 0.0248(3) Uani 1 1 d . . .
N29 N 0.36071(13) 0.13041(7) 0.58945(7) 0.0231(3) Uani 1 1 d . . .
O3A O 0.76888(12) 0.11722(7) 0.64735(7) 0.0312(3) Uani 1 1 d . . .
O28 O 0.51990(11) 0.04855(6) 0.63171(6) 0.0274(3) Uani 1 1 d . . .
O34 O 0.52954(11) 0.10840(7) 0.46232(6) 0.0306(3) Uani 1 1 d . . .
O35 O 0.44542(11) -0.01774(7) 0.45052(7) 0.0322(3) Uani 1 1 d . . .
H8 H 0.7418(19) 0.1741(11) 0.8805(11) 0.035(5) Uiso 1 1 d . . .
H3O H 0.701(2) 0.0870(11) 0.6387(11) 0.034(5) Uiso 1 1 d . . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C2 N1 1.4518(18) . ?
C2 C3 1.5334(19) . ?
C2 C28 1.542(2) . ?
C2 H2 1.0000 . ?
C3 C3A 1.540(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3A O3A 1.4224(18) . ?
C3A C4A 1.502(2) . ?
C3A C8A 1.547(2) . ?
C4 C4A 1.379(2) . ?
C4 C5 1.385(2) . ?
C4 H4 0.9500 . ?
C4A C7A 1.399(2) . ?
C5 C6 1.387(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.394(2) . ?
C6 H6 0.9500 . ?
C7 C7A 1.387(2) . ?
C7 H7 0.9500 . ?
C7A N8 1.3981(19) . ?
C8A N1 1.4438(18) . ?
C8A N8 1.4781(19) . ?
C8A H8A 1.0000 . ?
C9 N1 1.4768(18) . ?
C9 C22 1.5455(19) . ?
C9 C16 1.5549(19) . ?
C9 C10 1.564(2) . ?
C10 C15 1.390(2) . ?
C10 C11 1.391(2) . ?
C11 C12 1.385(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.376(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.377(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.384(2) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C21 1.383(2) . ?
C16 C17 1.401(2) . ?
C17 C18 1.380(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.381(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.381(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.398(2) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 C23 1.393(2) . ?
C22 C27 1.398(2) . ?
C23 C24 1.392(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.374(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.385(2) . ?
C25 H25 0.9500 . ?
C26 C27 1.382(2) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 O28 1.2354(17) . ?
C28 N29 1.339(2) . ?
C30 N29 1.4644(18) . ?
C30 C34 1.512(2) . ?
C30 C31 1.540(2) . ?
C30 H30 1.0000 . ?
C31 C32 1.514(2) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 C33 1.538(2) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 N29 1.4715(19) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 O34 1.1969(18) . ?
C34 O35 1.3329(18) . ?
C35 O35 1.446(2) . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
N8 H8 0.854(19) . ?
O3A H3O 0.87(2) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9745285
