#------------------------------------------------------------------------------
#$Date: 2022-09-14 21:32:59 +0300 (Wed, 14 Sep 2022) $
#$Revision: 277840 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/12/4021291.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_4021291
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         'C13 H20 N2 '
_chemical_formula_sum            'C13 H20 N2'
_chemical_formula_weight         204.31
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                103.712(6)
_cell_angle_beta                 99.04(1)
_cell_angle_gamma                104.228(5)
_cell_formula_units_Z            4
_cell_length_a                   8.3392(3)
_cell_length_b                   11.6677(4)
_cell_length_c                   15.175(2)
_cell_measurement_temperature    296.1
_cell_volume                     1353.5(2)
_exptl_crystal_density_diffrn    1.003
_cod_database_code               4021291
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-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 0.5616 0.3098 0.0153 0.111(3) Uani 1.00 1 d . . .
N(2) N 0.3237 0.0026 0.1103 0.121(3) Uani 1.00 1 d . . .
N(3) N 0.8173 1.0047 0.1119 0.121(3) Uani 1.00 1 d . . .
N(4) N 0.8335 0.7048 -0.1154 0.113(3) Uani 1.00 1 d . . .
C(23) C 0.8777 0.7175 0.1201 0.063(2) Uani 1.00 1 d . . .
C(5) C 0.9161 0.2992 0.3804 0.057(2) Uani 1.00 1 d . . .
C(8) C 0.7535 0.1883 0.3496 0.060(2) Uani 1.00 1 d . . .
C(26) C 0.8785 0.7540 -0.0372 0.077(3) Uani 1.00 1 d . . .
C(19) C 1.1147 0.8193 0.2710 0.059(2) Uani 1.00 1 d . . .
C(21) C 1.1518 0.6517 0.1445 0.070(2) Uani 1.00 1 d . . .
C(24) C 0.9337 0.8132 0.0662 0.060(2) Uani 1.00 1 d . . .
C(14) C 1.3785 0.7378 0.3026 0.062(2) Uani 1.00 1 d . . .
C(7) C 0.7606 0.3980 0.2721 0.078(2) Uani 1.00 1 d . . .
C(1) C 1.0796 0.2683 0.4178 0.066(2) Uani 1.00 1 d . . .
C(20) C 0.9218 0.7795 0.2267 0.071(2) Uani 1.00 1 d . . .
C(25) C 0.8671 0.9208 0.0899 0.078(2) Uani 1.00 1 d . . .
C(18) C 1.1894 0.7090 0.2509 0.058(2) Uani 1.00 1 d . . .
C(11) C 0.5832 0.1980 0.1485 0.061(2) Uani 1.00 1 d . . .
C(10) C 0.5982 0.2930 0.2452 0.066(2) Uani 1.00 1 d . . .
C(22) C 0.9613 0.6139 0.0997 0.073(2) Uani 1.00 1 d . . .
C(6) C 0.9207 0.3596 0.3002 0.072(2) Uani 1.00 1 d . . .
C(12) C 0.5702 0.2599 0.0708 0.075(2) Uani 1.00 1 d . . .
C(13) C 0.4352 0.0870 0.1251 0.080(3) Uani 1.00 1 d . . .
C(9) C 0.5933 0.2269 0.3237 0.073(2) Uani 1.00 1 d . . .
C(4) C 1.2366 0.3840 0.4451 0.096(3) Uani 1.00 1 d . . .
C(17) C 1.3916 0.7738 0.4088 0.111(3) Uani 1.00 1 d . . .
C(16) C 1.4948 0.8433 0.2765 0.097(3) Uani 1.00 1 d . . .
C(3) C 1.1143 0.1627 0.3454 0.094(3) Uani 1.00 1 d . . .
C(2) C 1.0668 0.2246 0.5073 0.109(4) Uani 1.00 1 d . . .
C(15) C 1.4437 0.6239 0.2782 0.098(3) Uani 1.00 1 d . . .
H(1) H 1.0500 0.2886 0.5535 0.136(5) Uiso 1.00 1 c . . .
H(2) H 0.9728 0.1525 0.4924 0.136(5) Uiso 1.00 1 c . . .
H(3) H 1.1680 0.2070 0.5304 0.136(5) Uiso 1.00 1 c . . .
H(4) H 1.0228 0.0893 0.3313 0.107(3) Uiso 1.00 1 c . . .
H(5) H 1.1241 0.1857 0.2900 0.107(3) Uiso 1.00 1 c . . .
H(6) H 1.2169 0.1487 0.3708 0.107(3) Uiso 1.00 1 c . . .
H(7) H 1.3363 0.3653 0.4690 0.104(3) Uiso 1.00 1 c . . .
H(8) H 1.2497 0.4114 0.3918 0.104(3) Uiso 1.00 1 c . . .
H(9) H 1.2183 0.4471 0.4914 0.104(3) Uiso 1.00 1 c . . .
H(10) H 0.8987 0.3573 0.4307 0.067(2) Uiso 1.00 1 c . . .
H(11) H 0.7638 0.1317 0.2959 0.074(3) Uiso 1.00 1 c . . .
H(12) H 0.7441 0.1497 0.3978 0.074(3) Uiso 1.00 1 c . . .
H(13) H 0.4977 0.1553 0.3023 0.089(3) Uiso 1.00 1 c . . .
H(14) H 0.5818 0.2806 0.3786 0.089(3) Uiso 1.00 1 c . . .
H(15) H 1.0188 0.4293 0.3180 0.079(3) Uiso 1.00 1 c . . .
H(16) H 0.9284 0.3004 0.2472 0.079(3) Uiso 1.00 1 c . . .
H(17) H 0.7707 0.4325 0.2218 0.089(3) Uiso 1.00 1 c . . .
H(18) H 0.7567 0.4592 0.3249 0.089(3) Uiso 1.00 1 c . . .
H(19) H 0.5043 0.3254 0.2388 0.080(3) Uiso 1.00 1 c . . .
H(20) H 0.6840 0.1735 0.1530 0.070(2) Uiso 1.00 1 c . . .
H(21) H 1.5060 0.7934 0.4419 0.133(4) Uiso 1.00 1 c . . .
H(22) H 1.3514 0.8435 0.4254 0.133(4) Uiso 1.00 1 c . . .
H(23) H 1.3231 0.7066 0.4240 0.133(4) Uiso 1.00 1 c . . .
H(24) H 1.3745 0.5582 0.2947 0.124(4) Uiso 1.00 1 c . . .
H(25) H 1.4389 0.5993 0.2133 0.124(4) Uiso 1.00 1 c . . .
H(26) H 1.5578 0.6442 0.3120 0.123(4) Uiso 1.00 1 c . . .
H(27) H 1.6079 0.8620 0.3112 0.114(4) Uiso 1.00 1 c . . .
H(28) H 1.4918 0.8192 0.2118 0.114(4) Uiso 1.00 1 c . . .
H(29) H 1.4563 0.9142 0.2911 0.114(4) Uiso 1.00 1 c . . .
H(30) H 1.1239 0.6483 0.2735 0.071(3) Uiso 1.00 1 c . . .
H(31) H 1.1731 0.8792 0.2450 0.070(2) Uiso 1.00 1 c . . .
H(32) H 1.1337 0.8538 0.3364 0.070(2) Uiso 1.00 1 c . . .
H(33) H 0.8845 0.8512 0.2362 0.088(3) Uiso 1.00 1 c . . .
H(34) H 0.8638 0.7249 0.2567 0.088(3) Uiso 1.00 1 c . . .
H(35) H 1.2102 0.7124 0.1193 0.087(3) Uiso 1.00 1 c . . .
H(36) H 1.1935 0.5821 0.1319 0.087(3) Uiso 1.00 1 c . . .
H(37) H 0.9068 0.5491 0.1225 0.082(3) Uiso 1.00 1 c . . .
H(38) H 0.9458 0.5843 0.0340 0.082(3) Uiso 1.00 1 c . . .
H(39) H 0.7581 0.6823 0.0992 0.073(3) Uiso 1.00 1 c . . .
H(40) H 1.0543 0.8431 0.0831 0.070(2) 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) 1.135612 yes . .
N(2) C(13) 1.124032 yes . .
N(3) C(25) 1.153742 yes . .
N(4) C(26) 1.145458 yes . .
C(23) C(24) 1.559565 yes . .
C(23) C(20) 1.549631 yes . .
C(23) C(22) 1.531615 yes . .
C(23) H(39) 0.949986 no . .
C(5) C(8) 1.543382 yes . .
C(5) C(1) 1.551496 yes . .
C(5) C(6) 1.544621 yes . .
C(5) H(10) 0.949955 no . .
C(8) C(9) 1.535208 yes . .
C(8) H(11) 0.950041 no . .
C(8) H(12) 0.949964 no . .
C(26) C(24) 1.499940 yes . .
C(19) C(20) 1.549188 yes . .
C(19) C(18) 1.551109 yes . .
C(19) H(31) 0.949994 no . .
C(19) H(32) 0.950029 no . .
C(21) C(18) 1.542192 yes . .
C(21) C(22) 1.534093 yes . .
C(21) H(35) 0.950001 no . .
C(21) H(36) 0.950016 no . .
C(24) C(25) 1.485354 yes . .
C(24) H(40) 0.949968 no . .
C(14) C(18) 1.562033 yes . .
C(14) C(17) 1.543313 yes . .
C(14) C(16) 1.542067 yes . .
C(14) C(15) 1.543671 yes . .
C(7) C(10) 1.508343 yes . .
C(7) C(6) 1.539687 yes . .
C(7) H(17) 0.950016 no . .
C(7) H(18) 0.950033 no . .
C(1) C(4) 1.550106 yes . .
C(1) C(3) 1.562668 yes . .
C(1) C(2) 1.569718 yes . .
C(20) H(33) 0.950023 no . .
C(20) H(34) 0.950025 no . .
C(18) H(30) 0.950031 no . .
C(11) C(10) 1.581781 yes . .
C(11) C(12) 1.524333 yes . .
C(11) C(13) 1.478797 yes . .
C(11) H(20) 0.949970 no . .
C(10) C(9) 1.564732 yes . .
C(10) H(19) 0.949968 no . .
C(22) H(37) 0.949939 no . .
C(22) H(38) 0.950010 no . .
C(6) H(15) 0.949975 no . .
C(6) H(16) 0.950101 no . .
C(9) H(13) 0.950040 no . .
C(9) H(14) 0.949989 no . .
C(4) H(7) 0.949951 no . .
C(4) H(8) 0.949950 no . .
C(4) H(9) 0.950048 no . .
C(17) H(21) 0.949982 no . .
C(17) H(22) 0.950032 no . .
C(17) H(23) 0.949985 no . .
C(16) H(27) 0.949967 no . .
C(16) H(28) 0.950045 no . .
C(16) H(29) 0.949960 no . .
C(3) H(4) 0.949953 no . .
C(3) H(5) 0.950089 no . .
C(3) H(6) 0.949978 no . .
C(2) H(1) 0.950106 no . .
C(2) H(2) 0.950012 no . .
C(2) H(3) 0.950034 no . .
C(15) H(24) 0.950060 no . .
C(15) H(25) 0.950099 no . .
C(15) H(26) 0.949922 no . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9346824
