#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/07/4020700.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_4020700
loop_
_publ_author_name
'Birte Basler'
'Oliver Schuster'
'Thorsten Bach'
_publ_section_title
;
 Conformationally Constrained β-Amino Acid Derivatives
 by Intramolecular [2 + 2]-Photocycloaddition of a Tetronic
 Acid Amide and Subsequent Lactone Ring Opening
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9798
_journal_page_last               9808
_journal_paper_doi               10.1021/jo0515226
_journal_volume                  70
_journal_year                    2005
_chemical_formula_sum            'C22.5 H25 Cl N2 O3'
_chemical_formula_weight         406.90
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   32.3497(6)
_cell_length_b                   9.91170(10)
_cell_length_c                   12.2514(2)
_cell_measurement_temperature    143(2)
_cell_volume                     3928.30(10)
_diffrn_ambient_temperature      143(2)
_exptl_crystal_density_diffrn    1.376
_cod_original_formula_sum        'C22.50 H25 Cl N2 O3'
_cod_database_code               4020700
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'
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
C99 C 0.0000 0.1683(3) 0.2500 0.0374(6) Uani 1 2 d S . .
Cl99 Cl 0.018080(15) 0.06829(6) 0.14103(4) 0.04932(16) Uani 1 1 d . . .
O1 O -0.10046(3) 0.74832(11) 0.70271(9) 0.0277(3) Uani 1 1 d . . .
N2 N -0.15574(4) 0.65664(12) 0.61659(9) 0.0194(3) Uani 1 1 d . . .
C8 C -0.18376(4) 0.93852(14) 0.80931(12) 0.0201(3) Uani 1 1 d . . .
O2 O -0.20995(3) 1.01089(11) 0.85367(9) 0.0282(3) Uani 1 1 d . . .
N9 N -0.14527(4) 0.92326(13) 0.84765(10) 0.0225(3) Uani 1 1 d . . .
O3 O -0.21543(4) 0.65972(11) 0.87589(9) 0.0265(3) Uani 1 1 d . . .
C30 C -0.18343(5) 0.62590(15) 0.80235(12) 0.0209(3) Uani 1 1 d . . .
C10 C -0.12967(5) 0.99299(16) 0.94330(13) 0.0249(3) Uani 1 1 d . . .
C11 C -0.12466(5) 0.90268(15) 1.04235(12) 0.0229(3) Uani 1 1 d . . .
C12 C -0.08800(5) 0.90079(18) 1.10049(14) 0.0308(4) Uani 1 1 d . . .
C13 C -0.08360(6) 0.8218(2) 1.19296(14) 0.0363(4) Uani 1 1 d . . .
C14 C -0.11607(6) 0.74388(18) 1.22930(14) 0.0360(4) Uani 1 1 d . . .
C15 C -0.15300(6) 0.74547(18) 1.17205(15) 0.0359(4) Uani 1 1 d . . .
C16 C -0.15731(5) 0.82278(16) 1.07869(14) 0.0294(4) Uani 1 1 d . . .
C20 C -0.11491(4) 0.68052(15) 0.62622(12) 0.0210(3) Uani 1 1 d . . .
C21 C -0.08644(4) 0.62489(16) 0.54073(12) 0.0227(3) Uani 1 1 d . . .
C22 C -0.05521(5) 0.70848(18) 0.50194(14) 0.0297(4) Uani 1 1 d . . .
C23 C -0.02730(6) 0.6607(2) 0.42523(15) 0.0412(5) Uani 1 1 d . . .
C24 C -0.03026(6) 0.5296(2) 0.38807(15) 0.0484(5) Uani 1 1 d . . .
C25 C -0.06096(6) 0.4454(2) 0.42686(16) 0.0432(5) Uani 1 1 d . . .
C26 C -0.08896(5) 0.49235(18) 0.50341(14) 0.0308(4) Uani 1 1 d . . .
C1 C -0.18638(4) 0.70548(14) 0.69627(11) 0.0173(3) Uani 1 1 d . . .
C7 C -0.19232(5) 0.86317(14) 0.70439(12) 0.0199(3) Uani 1 1 d . . .
C6 C -0.23790(5) 0.84495(16) 0.67148(15) 0.0289(4) Uani 1 1 d . . .
C5 C -0.22861(4) 0.69840(15) 0.63685(12) 0.0212(3) Uani 1 1 d . . .
C4 C -0.21767(5) 0.67662(17) 0.51673(13) 0.0265(3) Uani 1 1 d . . .
C3 C -0.17716(5) 0.59897(17) 0.52016(13) 0.0258(3) Uani 1 1 d . . .
H99A H -0.0191(15) 0.227(5) 0.218(4) 0.031 Uiso 0.50 1 d P . .
H99B H 0.0281(15) 0.210(5) 0.268(4) 0.031 Uiso 0.50 1 d P . .
H00A H -0.1504(6) 1.0686(18) 0.9604(14) 0.031 Uiso 1 1 d . . .
H00B H -0.1029(6) 1.0360(18) 0.9239(15) 0.031 Uiso 1 1 d . . .
H006 H -0.0649(6) 0.9541(18) 1.0761(15) 0.031 Uiso 1 1 d . . .
H012 H -0.0588(6) 0.8218(18) 1.2284(15) 0.031 Uiso 1 1 d . . .
H021 H -0.1132(6) 0.6894(18) 1.2936(16) 0.031 Uiso 1 1 d . . .
H007 H -0.1768(6) 0.6916(18) 1.1945(15) 0.031 Uiso 1 1 d . . .
H016 H -0.1833(6) 0.8217(18) 1.0403(15) 0.031 Uiso 1 1 d . . .
H010 H -0.0531(6) 0.7998(19) 0.5284(15) 0.031 Uiso 1 1 d . . .
H022 H -0.0055(6) 0.7217(18) 0.4019(15) 0.031 Uiso 1 1 d . . .
H019 H -0.0095(6) 0.4926(19) 0.3364(15) 0.031 Uiso 1 1 d . . .
H020 H -0.0636(6) 0.3516(19) 0.4036(15) 0.031 Uiso 1 1 d . . .
H018 H -0.1103(6) 0.4309(18) 0.5334(15) 0.031 Uiso 1 1 d . . .
H1 H -0.1284(6) 0.875(2) 0.8100(16) 0.034(5) Uiso 1 1 d . . .
H14 H -0.2379(8) 0.613(3) 0.8577(19) 0.059(7) Uiso 1 1 d . . .
H10 H -0.1571(5) 0.6463(16) 0.8380(13) 0.021(4) Uiso 1 1 d . . .
H11 H -0.1862(5) 0.5260(17) 0.7852(13) 0.022(4) Uiso 1 1 d . . .
H2 H -0.1757(5) 0.9046(18) 0.6479(14) 0.024(4) Uiso 1 1 d . . .
H4 H -0.2559(6) 0.850(2) 0.7373(17) 0.042(5) Uiso 1 1 d . . .
H3 H -0.2486(6) 0.903(2) 0.6145(16) 0.038(5) Uiso 1 1 d . . .
H5 H -0.2480(5) 0.6310(17) 0.6633(13) 0.019(4) Uiso 1 1 d . . .
H6 H -0.2133(6) 0.759(2) 0.4821(16) 0.034(5) Uiso 1 1 d . . .
H7 H -0.2389(6) 0.6261(19) 0.4755(15) 0.033(5) Uiso 1 1 d . . .
H8 H -0.1824(5) 0.500(2) 0.5331(15) 0.030(4) Uiso 1 1 d . . .
H9 H -0.1598(6) 0.6114(18) 0.4515(15) 0.030(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
C99 Cl99 1.7627(17) . ?
C99 Cl99 1.7627(17) 3 ?
C99 H99A 0.93(6) . ?
C99 H99B 1.02(6) . ?
O1 C20 1.2444(18) . ?
N2 C20 1.3468(19) . ?
N2 C1 1.4730(18) . ?
N2 C3 1.4842(18) . ?
C8 O2 1.2361(18) . ?
C8 N9 1.3393(19) . ?
C8 C7 1.512(2) . ?
N9 C10 1.4509(19) . ?
N9 H1 0.86(2) . ?
O3 C30 1.4125(18) . ?
O3 H14 0.89(3) . ?
C30 C1 1.5232(19) . ?
C30 H10 0.978(18) . ?
C30 H11 1.016(17) . ?
C10 C11 1.517(2) . ?
C10 H00A 1.027(18) . ?
C10 H00B 0.994(19) . ?
C11 C12 1.383(2) . ?
C11 C16 1.393(2) . ?
C12 C13 1.385(3) . ?
C12 H006 0.963(19) . ?
C13 C14 1.378(3) . ?
C13 H012 0.912(19) . ?
C14 C15 1.386(3) . ?
C14 H021 0.959(19) . ?
C15 C16 1.384(3) . ?
C15 H007 0.977(19) . ?
C16 H016 0.963(19) . ?
C20 C21 1.500(2) . ?
C21 C22 1.390(2) . ?
C21 C26 1.393(2) . ?
C22 C23 1.387(2) . ?
C22 H010 0.964(19) . ?
C23 C24 1.380(3) . ?
C23 H022 0.971(19) . ?
C24 C25 1.381(3) . ?
C24 H019 0.992(19) . ?
C25 C26 1.384(2) . ?
C25 H020 0.977(19) . ?
C26 H018 0.991(19) . ?
C1 C5 1.5496(19) . ?
C1 C7 1.5779(19) . ?
C7 C6 1.539(2) . ?
C7 H2 0.968(18) . ?
C6 C5 1.543(2) . ?
C6 H4 0.99(2) . ?
C6 H3 0.97(2) . ?
C5 C4 1.529(2) . ?
C5 H5 0.971(17) . ?
C4 C3 1.520(2) . ?
C4 H6 0.93(2) . ?
C4 H7 0.990(19) . ?
C3 H8 1.007(19) . ?
C3 H9 1.019(18) . ?
