#------------------------------------------------------------------------------
#$Date: 2018-07-19 04:00:47 +0300 (Thu, 19 Jul 2018) $
#$Revision: 209123 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/12/4021294.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_4021294
loop_
_publ_author_name
'Tomoo Hayamizu'
'Hajime Maeda'
'Kazuhiko Mizuno'
_publ_section_title
;
 Diastereoselective Protonation on Radical Anions of Electron-Deficient
 Alkenes via Photoinduced Electron Transfer
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4997
_journal_page_last               5004
_journal_paper_doi               10.1021/jo0496953
_journal_volume                  69
_journal_year                    2004
_chemical_formula_moiety         'C20 H24 N2'
_chemical_formula_sum            'C20 H24 N2'
_chemical_formula_weight         292.42
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'C 1'
_space_group_name_H-M_alt        'C 1'
_cell_angle_alpha                92.734(3)
_cell_angle_beta                 112.610(2)
_cell_angle_gamma                114.056(3)
_cell_formula_units_Z            4
_cell_length_a                   11.7618(7)
_cell_length_b                   13.1850(8)
_cell_length_c                   13.7331(8)
_cell_measurement_temperature    296.1
_cell_volume                     1741.7(2)
_exptl_crystal_density_diffrn    1.115
_cod_database_code               4021294
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
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
N(3) N 0.5260 0.1798 1.0270 0.067(3) Uani 1.00 1 d . . .
N(4) N 0.3400 -0.1733 0.9992 0.067(2) Uani 1.00 1 d . . .
N(1) N -0.1059 -0.1227 1.0410 0.075(3) Uani 1.00 1 d . . .
N(2) N 0.0613 0.2169 1.0246 0.074(3) Uani 1.00 1 d . . .
C(10) C 0.0636 0.1326 1.0072 0.050(2) Uani 1.00 1 d . . .
C(8) C 0.0706 0.0257 0.9843 0.041(2) Uani 1.00 1 d . . .
C(30) C 0.4429 -0.0958 1.0201 0.048(2) Uani 1.00 1 d . . .
C(29) C 0.5496 0.1052 1.0376 0.048(2) Uani 1.00 1 d . . .
C(28) C 0.5763 0.0045 1.0434 0.042(2) Uani 1.00 1 d . . .
C(11) C 0.0483 0.0020 0.8628 0.042(2) Uani 1.00 1 d . . .
C(37) C 0.6860 0.0241 1.2645 0.046(2) Uani 1.00 1 d . . .
C(7) C 0.2198 0.0452 1.0634 0.051(2) Uani 1.00 1 d . . .
C(26) C 0.5070 -0.0426 0.8351 0.057(3) Uani 1.00 1 d . . .
C(38) C 0.7964 0.1499 1.3293 0.049(2) Uani 1.00 1 d . . .
C(6) C 0.2645 0.0838 1.1831 0.051(2) Uani 1.00 1 d . . .
C(31) C 0.6934 0.0132 1.1521 0.041(2) Uani 1.00 1 d . . .
C(9) C -0.0313 -0.0613 1.0132 0.051(2) Uani 1.00 1 d . . .
C(12) C 0.1002 -0.0798 0.8327 0.055(2) Uani 1.00 1 d . . .
C(32) C 0.8414 0.1090 1.1806 0.053(2) Uani 1.00 1 d . . .
C(33) C 0.9103 0.1427 1.3053 0.055(2) Uani 1.00 1 d . . .
C(18) C -0.1427 -0.1701 0.7199 0.056(2) Uani 1.00 1 d . . .
C(17) C -0.0993 -0.0418 0.7648 0.049(2) Uani 1.00 1 d . . .
C(27) C 0.6185 -0.0114 0.9497 0.054(2) Uani 1.00 1 d . . .
C(13) C -0.0067 -0.1429 0.7151 0.059(2) Uani 1.00 1 d . . .
C(1) C 0.3465 0.1994 1.2365 0.071(3) Uani 1.00 1 d . . .
C(39) C 0.7582 0.2431 1.2906 0.062(3) Uani 1.00 1 d . . .
C(25) C 0.4108 -0.1552 0.7825 0.076(3) Uani 1.00 1 d . . .
C(35) C 0.7647 -0.0406 1.3246 0.067(3) Uani 1.00 1 d . . .
C(36) C 0.5455 -0.0156 1.2623 0.068(3) Uani 1.00 1 d . . .
C(14) C 0.0050 -0.0545 0.6458 0.072(3) Uani 1.00 1 d . . .
C(19) C -0.1749 -0.2493 0.7928 0.077(3) Uani 1.00 1 d . . .
C(5) C 0.2306 0.0047 1.2431 0.070(3) Uani 1.00 1 d . . .
C(16) C -0.2041 -0.0155 0.7824 0.071(3) Uani 1.00 1 d . . .
C(15) C -0.0653 0.0102 0.6748 0.065(3) Uani 1.00 1 d . . .
C(21) C 0.4987 0.0394 0.7796 0.075(3) Uani 1.00 1 d . . .
C(40) C 0.8336 0.1715 1.4506 0.077(3) Uani 1.00 1 d . . .
C(34) C 0.9160 0.0370 1.3449 0.075(3) Uani 1.00 1 d . . .
C(20) C -0.2702 -0.2248 0.6086 0.085(3) Uani 1.00 1 d . . .
C(4) C 0.2786 0.0425 1.3542 0.096(5) Uani 1.00 1 d . . .
C(23) C 0.3038 -0.1019 0.6245 0.103(5) Uani 1.00 1 d . . .
C(2) C 0.3907 0.2341 1.3464 0.098(4) Uani 1.00 1 d . . .
C(3) C 0.3570 0.1554 1.4039 0.098(5) Uani 1.00 1 d . . .
C(22) C 0.3965 0.0082 0.6731 0.103(5) Uani 1.00 1 d . . .
C(24) C 0.3089 -0.1828 0.6769 0.105(4) Uani 1.00 1 d . . .
H(1) H 0.3696 0.2533 1.1951 0.083(4) Uiso 1.00 1 c . . .
H(2) H 0.4477 0.3130 1.3824 0.111(6) Uiso 1.00 1 c . . .
H(3) H 0.3901 0.1791 1.4801 0.126(7) Uiso 1.00 1 c . . .
H(4) H 0.2496 -0.0112 1.3941 0.128(7) Uiso 1.00 1 c . . .
H(5) H 0.1796 -0.0745 1.2076 0.091(5) Uiso 1.00 1 c . . .
H(6) H 0.2227 -0.0252 1.0522 0.064(3) Uiso 1.00 1 c . . .
H(7) H 0.2847 0.1013 1.0447 0.064(3) Uiso 1.00 1 c . . .
H(8) H 0.1038 0.0741 0.8547 0.050(2) Uiso 1.00 1 c . . .
H(9) H 0.1901 -0.0385 0.8365 0.065(3) Uiso 1.00 1 c . . .
H(10) H 0.1020 -0.1306 0.8794 0.065(3) Uiso 1.00 1 c . . .
H(11) H -0.0020 -0.2082 0.6883 0.067(3) Uiso 1.00 1 c . . .
H(12) H 0.1000 -0.0047 0.6661 0.081(4) Uiso 1.00 1 c . . .
H(13) H -0.0411 -0.0897 0.5703 0.081(4) Uiso 1.00 1 c . . .
H(14) H -0.1466 -0.0011 0.6132 0.073(4) Uiso 1.00 1 c . . .
H(15) H -0.0034 0.0898 0.7027 0.073(4) Uiso 1.00 1 c . . .
H(16) H -0.1671 0.0650 0.8053 0.090(4) Uiso 1.00 1 c . . .
H(17) H -0.2878 -0.0445 0.7171 0.090(4) Uiso 1.00 1 c . . .
H(18) H -0.2225 -0.0504 0.8373 0.090(4) Uiso 1.00 1 c . . .
H(19) H -0.2563 -0.2568 0.7975 0.079(4) Uiso 1.00 1 c . . .
H(20) H -0.1884 -0.3224 0.7639 0.079(4) Uiso 1.00 1 c . . .
H(21) H -0.0987 -0.2177 0.8632 0.078(4) Uiso 1.00 1 c . . .
H(22) H -0.3504 -0.2322 0.6156 0.082(4) Uiso 1.00 1 c . . .
H(23) H -0.2554 -0.1783 0.5596 0.082(4) Uiso 1.00 1 c . . .
H(24) H -0.2834 -0.2984 0.5816 0.082(4) Uiso 1.00 1 c . . .
H(29) H 0.4169 -0.2136 0.8190 0.093(5) Uiso 1.00 1 c . . .
H(28) H 0.2425 -0.2600 0.6399 0.111(5) Uiso 1.00 1 c . . .
H(27) H 0.2305 -0.1199 0.5542 0.122(7) Uiso 1.00 1 c . . .
H(26) H 0.3958 0.0648 0.6329 0.137(8) Uiso 1.00 1 c . . .
H(25) H 0.5629 0.1175 0.8149 0.100(5) Uiso 1.00 1 c . . .
H(30) H 0.6956 0.0580 0.9588 0.073(3) Uiso 1.00 1 c . . .
H(31) H 0.6449 -0.0709 0.9573 0.073(3) Uiso 1.00 1 c . . .
H(32) H 0.6977 -0.0566 1.1409 0.051(2) Uiso 1.00 1 c . . .
H(33) H 0.8898 0.0814 1.1543 0.067(3) Uiso 1.00 1 c . . .
H(34) H 0.8361 0.1715 1.1510 0.067(3) Uiso 1.00 1 c . . .
H(35) H 0.9966 0.2106 1.3375 0.060(3) Uiso 1.00 1 c . . .
H(36) H 0.9427 0.0001 1.3030 0.087(4) Uiso 1.00 1 c . . .
H(37) H 0.9785 0.0563 1.4197 0.087(4) Uiso 1.00 1 c . . .
H(38) H 0.7592 -0.0483 1.3913 0.075(4) Uiso 1.00 1 c . . .
H(39) H 0.7281 -0.1143 1.2801 0.075(4) Uiso 1.00 1 c . . .
H(40) H 0.5547 -0.0058 1.3344 0.079(4) Uiso 1.00 1 c . . .
H(41) H 0.5032 0.0278 1.2248 0.079(4) Uiso 1.00 1 c . . .
H(42) H 0.4895 -0.0943 1.2255 0.079(4) Uiso 1.00 1 c . . .
H(43) H 0.8351 0.3164 1.3289 0.077(4) Uiso 1.00 1 c . . .
H(44) H 0.7334 0.2332 1.2150 0.077(4) Uiso 1.00 1 c . . .
H(45) H 0.6817 0.2371 1.3027 0.077(4) Uiso 1.00 1 c . . .
H(46) H 0.8584 0.1156 1.4797 0.084(4) Uiso 1.00 1 c . . .
H(47) H 0.9100 0.2456 1.4866 0.084(4) Uiso 1.00 1 c . . .
H(48) H 0.7565 0.1671 1.4610 0.084(4) Uiso 1.00 1 c . . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
N(3) C(29) 1.13(1) yes . .
N(4) C(30) 1.13(1) yes . .
N(1) C(9) 1.13(1) yes . .
N(2) C(10) 1.14(1) yes . .
C(10) C(8) 1.47(1) yes . .
C(8) C(11) 1.58(1) yes . .
C(8) C(7) 1.57(1) yes . .
C(8) C(9) 1.48(1) yes . .
C(30) C(28) 1.48(1) yes . .
C(29) C(28) 1.48(1) yes . .
C(28) C(31) 1.55(1) yes . .
C(28) C(27) 1.58(1) yes . .
C(11) C(12) 1.55(2) yes . .
C(11) C(17) 1.572(9) yes . .
C(11) H(8) 0.95(1) no . .
C(37) C(38) 1.563(9) yes . .
C(37) C(31) 1.58(1) yes . .
C(37) C(35) 1.55(1) yes . .
C(37) C(36) 1.50(1) yes . .
C(7) C(6) 1.51(1) yes . .
C(7) H(6) 0.95(2) no . .
C(7) H(7) 0.95(1) no . .
C(26) C(27) 1.51(1) yes . .
C(26) C(25) 1.38(1) yes . .
C(26) C(21) 1.37(2) yes . .
C(38) C(33) 1.53(2) yes . .
C(38) C(39) 1.52(1) yes . .
C(38) C(40) 1.53(1) yes . .
C(6) C(1) 1.39(1) yes . .
C(6) C(5) 1.39(1) yes . .
C(31) C(32) 1.55(1) yes . .
C(31) H(32) 0.95(1) no . .
C(12) C(13) 1.53(1) yes . .
C(12) H(9) 0.95(1) no . .
C(12) H(10) 0.95(1) no . .
C(32) C(33) 1.53(1) yes . .
C(32) H(33) 0.95(2) no . .
C(32) H(34) 0.95(1) no . .
C(33) C(34) 1.54(2) yes . .
C(33) H(35) 0.950(9) no . .
C(18) C(17) 1.57(1) yes . .
C(18) C(13) 1.52(2) yes . .
C(18) C(19) 1.52(1) yes . .
C(18) C(20) 1.54(1) yes . .
C(17) C(16) 1.51(2) yes . .
C(17) C(15) 1.55(1) yes . .
C(27) H(30) 0.95(1) no . .
C(27) H(31) 0.95(2) no . .
C(13) C(14) 1.54(1) yes . .
C(13) H(11) 0.95(2) no . .
C(1) C(2) 1.38(2) yes . .
C(1) H(1) 0.95(2) no . .
C(39) H(43) 0.95(1) no . .
C(39) H(44) 0.95(1) no . .
C(39) H(45) 0.95(2) no . .
C(25) C(24) 1.39(1) yes . .
C(25) H(29) 0.95(2) no . .
C(35) C(34) 1.55(1) yes . .
C(35) H(38) 0.95(2) no . .
C(35) H(39) 0.95(1) no . .
C(36) H(40) 0.95(2) no . .
C(36) H(41) 0.95(2) no . .
C(36) H(42) 0.95(1) no . .
C(14) C(15) 1.54(2) yes . .
C(14) H(12) 0.95(1) no . .
C(14) H(13) 0.95(1) no . .
C(19) H(19) 0.95(2) no . .
C(19) H(20) 0.95(2) no . .
C(19) H(21) 0.95(1) no . .
C(5) C(4) 1.39(2) yes . .
C(5) H(5) 0.95(1) no . .
C(16) H(16) 0.95(2) no . .
C(16) H(17) 0.95(1) no . .
C(16) H(18) 0.95(2) no . .
C(15) H(14) 0.95(1) no . .
C(15) H(15) 0.95(1) no . .
C(21) C(22) 1.39(1) yes . .
C(21) H(25) 0.95(1) no . .
C(40) H(46) 0.95(2) no . .
C(40) H(47) 0.95(1) no . .
C(40) H(48) 0.95(2) no . .
C(34) H(36) 0.95(2) no . .
C(34) H(37) 0.95(1) no . .
C(20) H(22) 0.95(2) no . .
C(20) H(23) 0.95(2) no . .
C(20) H(24) 0.95(2) no . .
C(4) C(3) 1.35(2) yes . .
C(4) H(4) 0.95(2) no . .
C(23) C(22) 1.34(2) yes . .
C(23) C(24) 1.32(2) yes . .
C(23) H(27) 0.95(2) no . .
C(2) C(3) 1.36(2) yes . .
C(2) H(2) 0.95(2) no . .
C(3) H(3) 0.95(2) no . .
C(22) H(26) 0.95(2) no . .
C(24) H(28) 0.95(2) no . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658509
