#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/12/4021258.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_4021258
loop_
_publ_author_name
'Masakazu Atobe'
'Naoki Yamazaki'
'Chihiro Kibayashi'
_publ_section_title
;
 Enantioselective Synthesis of Primary 1-(Aryl)alkylamines
 by Nucleophilic 1,2-Addition of Organolithium
 Reagents to Hydroxyoxime Ethers and Application to Asymmetric
 Synthesis of G-Protein-Coupled Receptor Ligands
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5595
_journal_page_last               5607
_journal_paper_doi               10.1021/jo049517+
_journal_volume                  69
_journal_year                    2004
_chemical_formula_moiety         'C16 H17 N O2'
_chemical_formula_sum            'C16 H17 N O2'
_chemical_formula_weight         255.31
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_cell_angle_alpha                90.00
_cell_angle_beta                 95.724(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.5250(2)
_cell_length_b                   30.9290(13)
_cell_length_c                   8.1140(4)
_cell_measurement_temperature    100(2)
_cell_volume                     1379.63(10)
_diffrn_ambient_temperature      100(2)
_exptl_crystal_density_diffrn    1.229
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4021258
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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
C1 C -0.0212(8) -0.36853(14) -0.0039(5) 0.0318(9) Uani 1 1 d . . .
H1 H -0.1587 -0.3540 0.0454 0.038 Uiso 1 1 calc R . .
C2 C -0.0314(9) -0.41696(14) 0.0285(6) 0.0364(11) Uani 1 1 d . . .
H2A H -0.1779 -0.4292 -0.0349 0.044 Uiso 1 1 calc R . .
H2B H 0.1131 -0.4310 -0.0112 0.044 Uiso 1 1 calc R . .
C3 C -0.0356(8) -0.35825(14) -0.1877(5) 0.0296(9) Uani 1 1 d . . .
C4 C 0.1469(8) -0.37234(14) -0.2826(5) 0.0300(9) Uani 1 1 d . . .
H4 H 0.2820 -0.3880 -0.2316 0.036 Uiso 1 1 calc R . .
C5 C 0.1312(8) -0.36346(14) -0.4508(5) 0.0316(9) Uani 1 1 d . . .
H5 H 0.2558 -0.3732 -0.5145 0.038 Uiso 1 1 calc R . .
C6 C -0.0630(8) -0.34068(14) -0.5266(6) 0.0325(9) Uani 1 1 d . . .
H6 H -0.0729 -0.3349 -0.6420 0.039 Uiso 1 1 calc R . .
C7 C -0.2447(8) -0.32622(15) -0.4330(5) 0.0340(10) Uani 1 1 d . . .
H7 H -0.3788 -0.3103 -0.4844 0.041 Uiso 1 1 calc R . .
C8 C -0.2298(8) -0.33503(14) -0.2639(6) 0.0329(10) Uani 1 1 d . . .
H8 H -0.3540 -0.3250 -0.2004 0.039 Uiso 1 1 calc R . .
C9 C 0.4148(8) -0.29545(14) 0.1496(5) 0.0313(9) Uani 1 1 d . . .
H9 H 0.5316 -0.3159 0.1945 0.038 Uiso 1 1 calc R . .
C10 C 0.4713(8) -0.24928(13) 0.1616(5) 0.0294(9) Uani 1 1 d . . .
C11 C 0.3099(9) -0.21789(15) 0.0964(6) 0.0378(10) Uani 1 1 d . . .
H11 H 0.1554 -0.2262 0.0441 0.045 Uiso 1 1 calc R . .
C12 C 0.3720(9) -0.17428(15) 0.1068(7) 0.0411(11) Uani 1 1 d . . .
H12 H 0.2590 -0.1533 0.0613 0.049 Uiso 1 1 calc R . .
C13 C 0.5958(8) -0.16101(13) 0.1823(6) 0.0323(10) Uani 1 1 d . . .
C14 C 0.7559(9) -0.19247(15) 0.2486(6) 0.0396(11) Uani 1 1 d . . .
H14 H 0.9091 -0.1840 0.3024 0.047 Uiso 1 1 calc R . .
C15 C 0.6971(9) -0.23606(15) 0.2380(6) 0.0401(11) Uani 1 1 d . . .
H15 H 0.8108 -0.2570 0.2830 0.048 Uiso 1 1 calc R . .
C16 C 0.6634(11) -0.11392(16) 0.1906(7) 0.0442(12) Uani 1 1 d . . .
H16A H 0.8327 -0.1109 0.2381 0.066 Uiso 1 1 calc R . .
H16B H 0.5565 -0.0986 0.2603 0.066 Uiso 1 1 calc R . .
H16C H 0.6451 -0.1016 0.0788 0.066 Uiso 1 1 calc R . .
C20 C 0.5562(9) 0.01397(13) 0.4717(5) 0.0310(9) Uani 1 1 d . . .
H20 H 0.7278 0.0243 0.4720 0.037 Uiso 1 1 calc R . .
C21 C 0.3994(9) 0.05053(14) 0.5262(6) 0.0341(10) Uani 1 1 d . . .
H21A H 0.3779 0.0726 0.4376 0.041 Uiso 1 1 calc R . .
H21B H 0.2367 0.0392 0.5446 0.041 Uiso 1 1 calc R . .
C22 C 0.4645(8) -0.00082(13) 0.2996(5) 0.0290(9) Uani 1 1 d . . .
C23 C 0.2413(8) -0.02177(15) 0.2655(6) 0.0336(9) Uani 1 1 d . . .
H23 H 0.1462 -0.0285 0.3534 0.040 Uiso 1 1 calc R . .
C24 C 0.1578(9) -0.03280(16) 0.1047(6) 0.0361(10) Uani 1 1 d . . .
H24 H 0.0055 -0.0471 0.0837 0.043 Uiso 1 1 calc R . .
C25 C 0.2929(8) -0.02338(15) -0.0274(6) 0.0347(10) Uani 1 1 d . . .
H25 H 0.2335 -0.0308 -0.1377 0.042 Uiso 1 1 calc R . .
C26 C 0.5138(8) -0.00309(14) 0.0055(6) 0.0318(9) Uani 1 1 d . . .
H26 H 0.6085 0.0035 -0.0828 0.038 Uiso 1 1 calc R . .
C27 C 0.5993(8) 0.00785(13) 0.1665(5) 0.0295(9) Uani 1 1 d . . .
H27 H 0.7533 0.0216 0.1869 0.035 Uiso 1 1 calc R . .
C28 C 0.7095(8) -0.08231(14) 0.6709(5) 0.0316(9) Uani 1 1 d . . .
H28 H 0.5877 -0.0817 0.7456 0.038 Uiso 1 1 calc R . .
C29 C 0.8717(8) -0.11993(14) 0.6695(6) 0.0312(9) Uani 1 1 d . . .
C30 C 0.8071(9) -0.15762(15) 0.7474(6) 0.0333(9) Uani 1 1 d . . .
H30 H 0.6699 -0.1576 0.8092 0.040 Uiso 1 1 calc R . .
C31 C 0.9407(8) -0.19542(15) 0.7362(6) 0.0373(10) Uani 1 1 d . . .
H31 H 0.8914 -0.2210 0.7887 0.045 Uiso 1 1 calc R . .
C32 C 1.1467(8) -0.19647(15) 0.6489(6) 0.0358(10) Uani 1 1 d . . .
C33 C 1.2148(9) -0.15805(15) 0.5747(6) 0.0365(10) Uani 1 1 d . . .
H33 H 1.3556 -0.1578 0.5164 0.044 Uiso 1 1 calc R . .
C34 C 1.0807(8) -0.12016(15) 0.5847(6) 0.0333(9) Uani 1 1 d . . .
H34 H 1.1310 -0.0944 0.5340 0.040 Uiso 1 1 calc R . .
C35 C 1.2893(10) -0.23752(17) 0.6346(8) 0.0496(13) Uani 1 1 d . . .
H35A H 1.3960 -0.2421 0.7370 0.074 Uiso 1 1 calc R . .
H35B H 1.3880 -0.2352 0.5411 0.074 Uiso 1 1 calc R . .
H35C H 1.1769 -0.2620 0.6165 0.074 Uiso 1 1 calc R . .
N17 N 0.2116(7) -0.30861(11) 0.0801(5) 0.0317(8) Uani 1 1 d . . .
N36 N 0.7301(7) -0.05020(12) 0.5724(4) 0.0319(8) Uani 1 1 d . . .
O18 O 0.2045(6) -0.35479(10) 0.0824(4) 0.0332(7) Uani 1 1 d . . .
O19 O -0.0383(7) -0.42636(11) 0.1994(4) 0.0415(8) Uani 1 1 d . . .
H19 H 0.1032 -0.4252 0.2478 0.062 Uiso 1 1 calc R . .
O37 O 0.5456(6) -0.01927(10) 0.5936(4) 0.0331(7) Uani 1 1 d . . .
O38 O 0.5074(7) 0.06988(11) 0.6741(4) 0.0407(8) Uani 1 1 d . . .
H38 H 0.4022 0.0727 0.7413 0.061 Uiso 1 1 calc R . .
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
C1 O18 1.432(5) . ?
C1 C3 1.520(6) . ?
C1 C2 1.523(6) . ?
C1 H1 1.0000 . ?
C2 O19 1.421(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C8 1.384(6) . ?
C3 C4 1.398(6) . ?
C4 C5 1.387(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.376(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.392(6) . ?
C6 H6 0.9500 . ?
C7 C8 1.393(6) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 N17 1.272(6) . ?
C9 C10 1.463(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.387(6) . ?
C10 C15 1.398(6) . ?
C11 C12 1.392(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.387(7) . ?
C12 H12 0.9500 . ?
C13 C14 1.387(6) . ?
C13 C16 1.503(6) . ?
C14 C15 1.387(7) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C20 O37 1.432(5) . ?
C20 C22 1.508(6) . ?
C20 C21 1.517(6) . ?
C20 H20 1.0000 . ?
C21 O38 1.419(6) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.396(6) . ?
C22 C27 1.398(6) . ?
C23 C24 1.382(7) . ?
C23 H23 0.9500 . ?
C24 C25 1.397(7) . ?
C24 H24 0.9500 . ?
C25 C26 1.374(7) . ?
C25 H25 0.9500 . ?
C26 C27 1.387(6) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 N36 1.287(6) . ?
C28 C29 1.469(6) . ?
C28 H28 0.9500 . ?
C29 C30 1.390(6) . ?
C29 C34 1.402(7) . ?
C30 C31 1.390(7) . ?
C30 H30 0.9500 . ?
C31 C32 1.400(7) . ?
C31 H31 0.9500 . ?
C32 C33 1.400(7) . ?
C32 C35 1.505(7) . ?
C33 C34 1.393(6) . ?
C33 H33 0.9500 . ?
C34 H34 0.9500 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
N17 O18 1.429(4) . ?
N36 O37 1.421(4) . ?
O19 H19 0.8400 . ?
O38 H38 0.8400 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658505
