#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/12/4021295.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_4021295
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 H26 N2'
_chemical_formula_sum            'C20 H26 N2'
_chemical_formula_weight         294.44
_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
_cell_angle_beta                 110.457(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.7104(3)
_cell_length_b                   6.4424(1)
_cell_length_c                   17.8094(4)
_cell_measurement_temperature    296.1
_cell_volume                     1796.36(6)
_exptl_crystal_density_diffrn    1.089
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4021295
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
N(1) N 1.4016 -0.7492 0.2798 0.086(3) Uani 1.00 1 d . . .
N(2) N 1.5370 -0.1892 0.3052 0.077(2) Uani 1.00 1 d . . .
N(3) N 1.0348 -0.4397 0.2213 0.114(4) Uani 1.00 1 d . . .
N(4) N 1.1613 0.1164 0.2049 0.097(3) Uani 1.00 1 d . . .
C(5) C 1.3708 -0.2095 -0.0016 0.044(2) Uani 1.00 1 d . . .
C(7) C 1.4056 -0.4574 0.1147 0.052(2) Uani 1.00 1 d . . .
C(11) C 1.3850 -0.3541 0.2449 0.042(2) Uani 1.00 1 d . . .
C(14) C 1.3228 -0.2602 0.2834 0.050(2) Uani 1.00 1 d . . .
C(10) C 1.3511 -0.3315 0.1521 0.043(2) Uani 1.00 1 d . . .
C(13) C 1.4714 -0.2603 0.2799 0.051(2) Uani 1.00 1 d . . .
C(9) C 1.3466 -0.1066 0.1258 0.055(2) Uani 1.00 1 d . . .
C(8) C 1.3150 -0.0890 0.0346 0.059(2) Uani 1.00 1 d . . .
C(33) C 1.1089 0.0485 0.2237 0.066(3) Uani 1.00 1 d . . .
C(34) C 0.9529 0.0520 0.2001 0.056(2) Uani 1.00 1 d . . .
C(3) C 1.3566 0.0543 -0.1091 0.066(3) Uani 1.00 1 d . . .
C(15) C 1.3507 -0.2812 0.3732 0.050(2) Uani 1.00 1 d . . .
C(1) C 1.3479 -0.1759 -0.0923 0.052(2) Uani 1.00 1 d . . .
C(40) C 0.8848 -0.1479 0.0724 0.063(2) Uani 1.00 1 d . . .
C(31) C 1.0415 -0.0414 0.2496 0.055(2) Uani 1.00 1 d . . .
C(38) C 0.8804 -0.0152 -0.0524 0.071(3) Uani 1.00 1 d . . .
C(20) C 1.3965 -0.1278 0.4222 0.063(2) Uani 1.00 1 d . . .
C(35) C 0.9267 0.0252 0.1115 0.053(2) Uani 1.00 1 d . . .
C(12) C 1.3954 -0.5804 0.2653 0.058(2) Uani 1.00 1 d . . .
C(19) C 1.4228 -0.1495 0.5048 0.073(3) Uani 1.00 1 d . . .
C(16) C 1.3323 -0.4586 0.4079 0.064(3) Uani 1.00 1 d . . .
C(37) C 0.9210 0.1616 -0.0158 0.068(3) Uani 1.00 1 d . . .
C(36) C 0.9441 0.1811 0.0669 0.058(2) Uani 1.00 1 d . . .
C(39) C 0.8619 -0.1682 -0.0087 0.074(3) Uani 1.00 1 d . . .
C(4) C 1.2569 -0.2481 -0.1406 0.077(3) Uani 1.00 1 d . . .
C(6) C 1.3724 -0.4338 0.0237 0.054(2) Uani 1.00 1 d . . .
C(29) C 1.0703 0.1959 0.3704 0.088(3) Uani 1.00 1 d . . .
C(2) C 1.4080 -0.2986 -0.1225 0.069(3) Uani 1.00 1 d . . .
C(18) C 1.4047 -0.3206 0.5388 0.077(3) Uani 1.00 1 d . . .
C(21) C 1.1892 0.1091 0.6010 0.064(3) Uani 1.00 1 d . . .
C(25) C 1.1648 0.0842 0.5104 0.066(3) Uani 1.00 1 d . . .
C(26) C 1.1558 -0.1356 0.4830 0.088(3) Uani 1.00 1 d . . .
C(24) C 1.2748 -0.0026 0.6440 0.085(3) Uani 1.00 1 d . . .
C(22) C 1.1228 0.0182 0.6320 0.084(3) Uani 1.00 1 d . . .
C(27) C 1.1422 -0.1441 0.3906 0.095(3) Uani 1.00 1 d . . .
C(30) C 1.0627 -0.0211 0.3428 0.070(3) Uani 1.00 1 d . . .
C(17) C 1.3616 -0.4744 0.4921 0.079(3) Uani 1.00 1 d . . .
C(32) C 1.0409 -0.2670 0.2330 0.071(3) Uani 1.00 1 d . . .
C(28) C 1.0844 0.2018 0.4611 0.099(4) Uani 1.00 1 d . . .
C(23) C 1.2030 0.3379 0.6246 0.106(5) Uani 1.00 1 d . . .
H(1) H 1.4031 -0.4423 -0.1130 0.088(4) Uiso 1.00 1 c . . .
H(2) H 1.3949 -0.2759 -0.1782 0.088(4) Uiso 1.00 1 c . . .
H(3) H 1.4647 -0.2538 -0.0940 0.088(4) Uiso 1.00 1 c . . .
H(4) H 1.4131 0.0978 -0.0793 0.081(3) Uiso 1.00 1 c . . .
H(5) H 1.3455 0.0750 -0.1646 0.081(3) Uiso 1.00 1 c . . .
H(6) H 1.3172 0.1332 -0.0931 0.081(3) Uiso 1.00 1 c . . .
H(7) H 1.2177 -0.1694 -0.1244 0.089(4) Uiso 1.00 1 c . . .
H(8) H 1.2459 -0.2261 -0.1960 0.089(4) Uiso 1.00 1 c . . .
H(9) H 1.2505 -0.3913 -0.1313 0.089(4) Uiso 1.00 1 c . . .
H(10) H 1.4267 -0.1556 0.0235 0.053(2) Uiso 1.00 1 c . . .
H(11) H 1.3168 -0.4912 0.0013 0.066(3) Uiso 1.00 1 c . . .
H(12) H 1.4104 -0.5073 0.0042 0.066(3) Uiso 1.00 1 c . . .
H(13) H 1.4630 -0.4102 0.1364 0.063(3) Uiso 1.00 1 c . . .
H(14) H 1.4031 -0.5997 0.1277 0.063(3) Uiso 1.00 1 c . . .
H(15) H 1.3125 0.0528 0.0193 0.071(3) Uiso 1.00 1 c . . .
H(16) H 1.2594 -0.1475 0.0141 0.071(3) Uiso 1.00 1 c . . .
H(17) H 1.3094 -0.0316 0.1459 0.067(3) Uiso 1.00 1 c . . .
H(18) H 1.4023 -0.0485 0.1466 0.067(3) Uiso 1.00 1 c . . .
H(19) H 1.2946 -0.3852 0.1323 0.051(2) Uiso 1.00 1 c . . .
H(20) H 1.3162 -0.1166 0.2706 0.062(2) Uiso 1.00 1 c . . .
H(21) H 1.2692 -0.3280 0.2609 0.062(2) Uiso 1.00 1 c . . .
H(22) H 1.3012 -0.5687 0.3751 0.081(3) Uiso 1.00 1 c . . .
H(23) H 1.3490 -0.5958 0.5161 0.103(4) Uiso 1.00 1 c . . .
H(24) H 1.4226 -0.3332 0.5954 0.096(4) Uiso 1.00 1 c . . .
H(25) H 1.4553 -0.0429 0.5387 0.088(3) Uiso 1.00 1 c . . .
H(26) H 1.4104 -0.0063 0.3991 0.078(3) Uiso 1.00 1 c . . .
H(27) H 1.1384 0.0413 0.6880 0.104(4) Uiso 1.00 1 c . . .
H(28) H 1.0698 0.0841 0.6046 0.104(4) Uiso 1.00 1 c . . .
H(29) H 1.1177 -0.1267 0.6215 0.104(4) Uiso 1.00 1 c . . .
H(30) H 1.2246 0.3520 0.6812 0.130(6) Uiso 1.00 1 c . . .
H(31) H 1.2453 0.3810 0.6035 0.130(6) Uiso 1.00 1 c . . .
H(32) H 1.1535 0.4219 0.6028 0.130(6) Uiso 1.00 1 c . . .
H(33) H 1.2654 -0.1466 0.6328 0.098(4) Uiso 1.00 1 c . . .
H(34) H 1.3162 0.0465 0.6228 0.098(4) Uiso 1.00 1 c . . .
H(35) H 1.2949 0.0187 0.7003 0.098(4) Uiso 1.00 1 c . . .
H(36) H 1.2113 0.1407 0.4982 0.077(3) Uiso 1.00 1 c . . .
H(37) H 1.2072 -0.2064 0.5117 0.097(4) Uiso 1.00 1 c . . .
H(38) H 1.1094 -0.2005 0.4929 0.097(4) Uiso 1.00 1 c . . .
H(39) H 1.1905 -0.0891 0.3808 0.105(4) Uiso 1.00 1 c . . .
H(40) H 1.1347 -0.2854 0.3745 0.105(4) Uiso 1.00 1 c . . .
H(41) H 1.0941 0.3419 0.4786 0.116(5) Uiso 1.00 1 c . . .
H(42) H 1.0350 0.1509 0.4697 0.116(5) Uiso 1.00 1 c . . .
H(43) H 1.1176 0.2575 0.3610 0.099(4) Uiso 1.00 1 c . . .
H(44) H 1.0197 0.2700 0.3417 0.099(4) Uiso 1.00 1 c . . .
H(45) H 1.0157 -0.0791 0.3539 0.078(3) Uiso 1.00 1 c . . .
H(46) H 0.9110 -0.0173 0.2157 0.068(3) Uiso 1.00 1 c . . .
H(47) H 0.9531 0.1955 0.2124 0.068(3) Uiso 1.00 1 c . . .
H(48) H 0.9720 0.3041 0.0924 0.068(3) Uiso 1.00 1 c . . .
H(49) H 0.9334 0.2694 -0.0464 0.081(3) Uiso 1.00 1 c . . .
H(50) H 0.8660 -0.0292 -0.1087 0.083(3) Uiso 1.00 1 c . . .
H(51) H 0.8328 -0.2888 -0.0353 0.086(3) Uiso 1.00 1 c . . .
H(52) H 0.8714 -0.2550 0.1027 0.075(3) 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(1) C(12) 1.11(1) yes . .
N(2) C(13) 1.13(1) yes . .
N(3) C(32) 1.13(1) yes . .
N(4) C(33) 1.13(1) yes . .
C(5) C(8) 1.52(1) yes . .
C(5) C(1) 1.54(1) yes . .
C(5) C(6) 1.51(1) yes . .
C(5) H(10) 0.950(9) no . .
C(7) C(10) 1.54(1) yes . .
C(7) C(6) 1.53(1) yes . .
C(7) H(13) 0.95(1) no . .
C(7) H(14) 0.95(1) no . .
C(11) C(14) 1.55(1) yes . .
C(11) C(10) 1.555(9) yes . .
C(11) C(13) 1.49(1) yes . .
C(11) C(12) 1.50(1) yes . .
C(14) C(15) 1.51(1) yes . .
C(14) H(20) 0.95(1) no . .
C(14) H(21) 0.95(1) no . .
C(10) C(9) 1.52(1) yes . .
C(10) H(19) 0.95(1) no . .
C(9) C(8) 1.53(1) yes . .
C(9) H(17) 0.95(1) no . .
C(9) H(18) 0.95(1) no . .
C(8) H(15) 0.95(1) no . .
C(8) H(16) 0.95(1) no . .
C(33) C(31) 1.48(1) yes . .
C(34) C(31) 1.56(1) yes . .
C(34) C(35) 1.49(1) yes . .
C(34) H(46) 0.95(1) no . .
C(34) H(47) 0.95(1) no . .
C(3) C(1) 1.53(1) yes . .
C(3) H(4) 0.95(1) no . .
C(3) H(5) 0.95(1) no . .
C(3) H(6) 0.95(2) no . .
C(15) C(20) 1.36(1) yes . .
C(15) C(16) 1.38(1) yes . .
C(1) C(4) 1.53(1) yes . .
C(1) C(2) 1.52(1) yes . .
C(40) C(35) 1.37(1) yes . .
C(40) C(39) 1.36(1) yes . .
C(40) H(52) 0.95(1) no . .
C(31) C(30) 1.58(1) yes . .
C(31) C(32) 1.48(1) yes . .
C(38) C(37) 1.37(1) yes . .
C(38) C(39) 1.36(2) yes . .
C(38) H(50) 0.95(1) no . .
C(20) C(19) 1.39(1) yes . .
C(20) H(26) 0.95(1) no . .
C(35) C(36) 1.37(1) yes . .
C(19) C(18) 1.34(2) yes . .
C(19) H(25) 0.95(1) no . .
C(16) C(17) 1.41(1) yes . .
C(16) H(22) 0.95(1) no . .
C(37) C(36) 1.39(1) yes . .
C(37) H(49) 0.95(1) no . .
C(36) H(48) 0.95(1) no . .
C(39) H(51) 0.95(2) no . .
C(4) H(7) 0.95(1) no . .
C(4) H(8) 0.95(1) no . .
C(4) H(9) 0.95(2) no . .
C(6) H(11) 0.95(1) no . .
C(6) H(12) 0.95(1) no . .
C(29) C(30) 1.47(1) yes . .
C(29) C(28) 1.55(1) yes . .
C(29) H(43) 0.95(2) no . .
C(29) H(44) 0.95(2) no . .
C(2) H(1) 0.95(1) no . .
C(2) H(2) 0.95(1) no . .
C(2) H(3) 0.95(1) no . .
C(18) C(17) 1.33(2) yes . .
C(18) H(24) 0.95(1) no . .
C(21) C(25) 1.53(1) yes . .
C(21) C(24) 1.54(1) yes . .
C(21) C(22) 1.52(2) yes . .
C(21) C(23) 1.53(2) yes . .
C(25) C(26) 1.49(2) yes . .
C(25) C(28) 1.53(1) yes . .
C(25) H(36) 0.95(1) no . .
C(26) C(27) 1.58(1) yes . .
C(26) H(37) 0.95(2) no . .
C(26) H(38) 0.95(2) no . .
C(24) H(33) 0.95(2) no . .
C(24) H(34) 0.95(2) no . .
C(24) H(35) 0.95(1) no . .
C(22) H(27) 0.95(1) no . .
C(22) H(28) 0.95(1) no . .
C(22) H(29) 0.95(2) no . .
C(27) C(30) 1.53(1) yes . .
C(27) H(39) 0.95(2) no . .
C(27) H(40) 0.95(2) no . .
C(30) H(45) 0.95(1) no . .
C(17) H(23) 0.95(2) no . .
C(28) H(41) 0.95(2) no . .
C(28) H(42) 0.95(2) no . .
C(23) H(30) 0.95(2) no . .
C(23) H(31) 0.95(2) no . .
C(23) H(32) 0.95(2) no . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9612724
