#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/07/4020762.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_4020762
loop_
_publ_author_name
'Jan M. Pedersen'
'W. Russell Bowman'
'Mark R. J. Elsegood'
'Anthony J. Fletcher'
'Peter J. Lovell'
_publ_section_title
;
 Synthesis of Ellipticine: A Radical Cascade Protocol
 to Aryl- and Heteroaryl-Annulated[b]carbazoles
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              10615
_journal_page_last               10618
_journal_paper_doi               10.1021/jo0519920
_journal_volume                  70
_journal_year                    2005
_chemical_formula_sum            'C23 H20 N2 Se'
_chemical_formula_weight         403.37
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_cell_angle_alpha                90.00
_cell_angle_beta                 105.705(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   22.0841(7)
_cell_length_b                   10.4436(3)
_cell_length_c                   17.3447(5)
_cell_measurement_temperature    150(2)
_cell_volume                     3851.0(2)
_diffrn_ambient_temperature      150(2)
_exptl_crystal_density_diffrn    1.391
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4020762
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
N1 N 0.46367(5) -0.00738(11) 0.24855(7) 0.0228(2) Uani 1 1 d . . .
C1 C 0.50039(6) -0.00047(14) 0.32928(9) 0.0222(3) Uani 1 1 d . . .
C2 C 0.50219(6) -0.10584(13) 0.38006(8) 0.0221(3) Uani 1 1 d . . .
C3 C 0.54341(7) -0.10356(15) 0.45764(9) 0.0261(3) Uani 1 1 d . . .
H3 H 0.5448 -0.1745 0.4923 0.031 Uiso 1 1 calc R . .
C4 C 0.58202(7) 0.00122(16) 0.48401(9) 0.0295(3) Uani 1 1 d . . .
H4 H 0.6099 0.0018 0.5364 0.035 Uiso 1 1 calc R . .
C5 C 0.57967(7) 0.10558(15) 0.43335(9) 0.0296(3) Uani 1 1 d . . .
H5 H 0.6059 0.1777 0.4516 0.036 Uiso 1 1 calc R . .
C6 C 0.53940(7) 0.10532(14) 0.35650(9) 0.0266(3) Uani 1 1 d . . .
H6 H 0.5383 0.1769 0.3223 0.032 Uiso 1 1 calc R . .
C7 C 0.41763(6) 0.06584(13) 0.21905(8) 0.0207(3) Uani 1 1 d . . .
C8 C 0.38072(6) 0.05370(13) 0.13144(8) 0.0215(3) Uani 1 1 d . . .
H8 H 0.3679 0.1415 0.1103 0.026 Uiso 1 1 calc R . .
C9 C 0.42038(7) -0.00651(15) 0.08035(9) 0.0280(3) Uani 1 1 d . . .
H9A H 0.4567 0.0483 0.0820 0.042 Uiso 1 1 calc R . .
H9B H 0.3947 -0.0149 0.0249 0.042 Uiso 1 1 calc R . .
H9C H 0.4350 -0.0913 0.1016 0.042 Uiso 1 1 calc R . .
C10 C 0.32132(6) -0.02366(14) 0.12628(8) 0.0216(3) Uani 1 1 d . . .
C11 C 0.26195(7) 0.02538(15) 0.08938(8) 0.0255(3) Uani 1 1 d . . .
H11 H 0.2575 0.1090 0.0670 0.031 Uiso 1 1 calc R . .
C12 C 0.20928(7) -0.04954(17) 0.08578(9) 0.0311(3) Uani 1 1 d . . .
H12 H 0.1691 -0.0140 0.0609 0.037 Uiso 1 1 calc R . .
N2 N 0.21149(6) -0.16827(14) 0.11501(8) 0.0328(3) Uani 1 1 d . . .
C13 C 0.26879(7) -0.21482(16) 0.15005(10) 0.0317(3) Uani 1 1 d . . .
H13 H 0.2717 -0.2992 0.1712 0.038 Uiso 1 1 calc R . .
C14 C 0.32443(7) -0.14743(14) 0.15750(9) 0.0260(3) Uani 1 1 d . . .
H14 H 0.3639 -0.1850 0.1834 0.031 Uiso 1 1 calc R . .
Se1 Se 0.388348(7) 0.187921(16) 0.286448(9) 0.02878(5) Uani 1 1 d . . .
C15 C 0.32179(6) 0.27894(13) 0.21185(8) 0.0226(3) Uani 1 1 d . . .
C16 C 0.26029(7) 0.26405(14) 0.21712(9) 0.0263(3) Uani 1 1 d . . .
H16 H 0.2513 0.2042 0.2538 0.032 Uiso 1 1 calc R . .
C17 C 0.21219(7) 0.33699(16) 0.16864(9) 0.0306(3) Uani 1 1 d . . .
H17 H 0.1703 0.3269 0.1723 0.037 Uiso 1 1 calc R . .
C18 C 0.22510(8) 0.42442(15) 0.11504(10) 0.0321(3) Uani 1 1 d . . .
H18 H 0.1921 0.4740 0.0819 0.038 Uiso 1 1 calc R . .
C19 C 0.28628(8) 0.43926(15) 0.10993(9) 0.0298(3) Uani 1 1 d . . .
H19 H 0.2951 0.4991 0.0731 0.036 Uiso 1 1 calc R . .
C20 C 0.33480(7) 0.36726(14) 0.15820(9) 0.0262(3) Uani 1 1 d . . .
H20 H 0.3767 0.3781 0.1547 0.031 Uiso 1 1 calc R . .
C21 C 0.46269(6) -0.21626(14) 0.35445(9) 0.0238(3) Uani 1 1 d . . .
C22 C 0.43189(7) -0.31137(14) 0.33829(9) 0.0271(3) Uani 1 1 d . . .
C23 C 0.39549(9) -0.42915(17) 0.31746(12) 0.0397(4) Uani 1 1 d . . .
H23A H 0.3639 -0.4180 0.2660 0.060 Uiso 1 1 calc R . .
H23B H 0.3744 -0.4488 0.3590 0.060 Uiso 1 1 calc R . .
H23C H 0.4237 -0.4997 0.3134 0.060 Uiso 1 1 calc R . .
N3 N 0.04651(5) 0.22986(12) 0.25785(7) 0.0240(2) Uani 1 1 d . . .
C24 C 0.01317(6) 0.21754(14) 0.17589(9) 0.0242(3) Uani 1 1 d . . .
C25 C 0.01097(6) 0.32214(14) 0.12422(9) 0.0237(3) Uani 1 1 d . . .
C26 C -0.02531(7) 0.31219(15) 0.04418(9) 0.0290(3) Uani 1 1 d . . .
H26 H -0.0270 0.3823 0.0088 0.035 Uiso 1 1 calc R . .
C27 C -0.05854(8) 0.20188(17) 0.01628(10) 0.0374(4) Uani 1 1 d . . .
H27 H -0.0824 0.1956 -0.0381 0.045 Uiso 1 1 calc R . .
C28 C -0.05669(8) 0.10002(17) 0.06852(10) 0.0398(4) Uani 1 1 d . . .
H28 H -0.0798 0.0243 0.0496 0.048 Uiso 1 1 calc R . .
C29 C -0.02169(7) 0.10739(16) 0.14777(10) 0.0317(3) Uani 1 1 d . . .
H29 H -0.0214 0.0376 0.1830 0.038 Uiso 1 1 calc R . .
C30 C 0.09170(6) 0.15660(13) 0.29119(8) 0.0209(3) Uani 1 1 d . . .
C31 C 0.12579(7) 0.17429(14) 0.37941(8) 0.0229(3) Uani 1 1 d . . .
H31 H 0.1403 0.0882 0.4023 0.027 Uiso 1 1 calc R . .
C32 C 0.08171(8) 0.22920(17) 0.42593(10) 0.0330(3) Uani 1 1 d . . .
H32A H 0.1052 0.2425 0.4820 0.050 Uiso 1 1 calc R . .
H32B H 0.0472 0.1690 0.4233 0.050 Uiso 1 1 calc R . .
H32C H 0.0646 0.3111 0.4022 0.050 Uiso 1 1 calc R . .
C33 C 0.18366(6) 0.25761(14) 0.38683(8) 0.0226(3) Uani 1 1 d . . .
C34 C 0.24380(7) 0.21143(16) 0.42304(9) 0.0283(3) Uani 1 1 d . . .
H34 H 0.2496 0.1261 0.4426 0.034 Uiso 1 1 calc R . .
C35 C 0.29511(7) 0.29182(18) 0.43022(9) 0.0350(4) Uani 1 1 d . . .
H35 H 0.3357 0.2588 0.4553 0.042 Uiso 1 1 calc R . .
N4 N 0.29102(6) 0.41238(15) 0.40412(8) 0.0379(3) Uani 1 1 d . . .
C36 C 0.23301(8) 0.45477(16) 0.36817(10) 0.0346(4) Uani 1 1 d . . .
H36 H 0.2288 0.5398 0.3480 0.042 Uiso 1 1 calc R . .
C37 C 0.17868(7) 0.38295(15) 0.35843(9) 0.0277(3) Uani 1 1 d . . .
H37 H 0.1387 0.4186 0.3328 0.033 Uiso 1 1 calc R . .
Se2 Se 0.123527(7) 0.029394(15) 0.229677(8) 0.02689(5) Uani 1 1 d . . .
C38 C 0.18194(7) -0.06633(13) 0.31148(8) 0.0228(3) Uani 1 1 d . . .
C39 C 0.24447(7) -0.07311(15) 0.31022(10) 0.0291(3) Uani 1 1 d . . .
H39 H 0.2587 -0.0253 0.2719 0.035 Uiso 1 1 calc R . .
C40 C 0.28622(8) -0.15042(17) 0.36551(11) 0.0395(4) Uani 1 1 d . . .
H40 H 0.3288 -0.1572 0.3639 0.047 Uiso 1 1 calc R . .
C41 C 0.26604(9) -0.21715(17) 0.42255(11) 0.0455(5) Uani 1 1 d . . .
H41 H 0.2949 -0.2684 0.4607 0.055 Uiso 1 1 calc R . .
C42 C 0.20373(9) -0.20955(16) 0.42427(10) 0.0407(4) Uani 1 1 d . . .
H42 H 0.1901 -0.2545 0.4642 0.049 Uiso 1 1 calc R . .
C43 C 0.16112(7) -0.13636(15) 0.36777(9) 0.0295(3) Uani 1 1 d . . .
H43 H 0.1181 -0.1341 0.3675 0.035 Uiso 1 1 calc R . .
C44 C 0.04460(7) 0.43848(14) 0.15233(9) 0.0253(3) Uani 1 1 d . . .
C45 C 0.07187(7) 0.53673(14) 0.17323(9) 0.0279(3) Uani 1 1 d . . .
C46 C 0.10444(9) 0.65710(16) 0.20091(11) 0.0388(4) Uani 1 1 d . . .
H46A H 0.0735 0.7261 0.1957 0.058 Uiso 1 1 calc R . .
H46B H 0.1332 0.6772 0.1684 0.058 Uiso 1 1 calc R . .
H46C H 0.1284 0.6486 0.2572 0.058 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
N1 C7 1.2644(18) . ?
N1 C1 1.4173(18) . ?
C1 C6 1.402(2) . ?
C1 C2 1.403(2) . ?
C2 C3 1.4059(19) . ?
C2 C21 1.442(2) . ?
C3 C4 1.386(2) . ?
C4 C5 1.392(2) . ?
C5 C6 1.388(2) . ?
C7 C8 1.5229(19) . ?
C7 Se1 1.9544(14) . ?
C8 C10 1.5225(19) . ?
C8 C9 1.539(2) . ?
C10 C11 1.392(2) . ?
C10 C14 1.396(2) . ?
C11 C12 1.389(2) . ?
C12 N2 1.336(2) . ?
N2 C13 1.338(2) . ?
C13 C14 1.391(2) . ?
Se1 C15 1.9258(14) . ?
C15 C20 1.394(2) . ?
C15 C16 1.394(2) . ?
C16 C17 1.390(2) . ?
C17 C18 1.387(2) . ?
C18 C19 1.386(2) . ?
C19 C20 1.389(2) . ?
C21 C22 1.194(2) . ?
C22 C23 1.460(2) . ?
N3 C30 1.2662(18) . ?
N3 C24 1.4188(18) . ?
C24 C29 1.397(2) . ?
C24 C25 1.405(2) . ?
C25 C26 1.406(2) . ?
C25 C44 1.439(2) . ?
C26 C27 1.381(2) . ?
C27 C28 1.391(2) . ?
C28 C29 1.385(2) . ?
C30 C31 1.5226(19) . ?
C30 Se2 1.9502(14) . ?
C31 C33 1.5225(19) . ?
C31 C32 1.534(2) . ?
C33 C37 1.392(2) . ?
C33 C34 1.393(2) . ?
C34 C35 1.389(2) . ?
C35 N4 1.333(2) . ?
N4 C36 1.339(2) . ?
C36 C37 1.386(2) . ?
Se2 C38 1.9198(14) . ?
C38 C39 1.389(2) . ?
C38 C43 1.394(2) . ?
C39 C40 1.394(2) . ?
C40 C41 1.379(3) . ?
C41 C42 1.387(3) . ?
C42 C43 1.390(2) . ?
C44 C45 1.195(2) . ?
C45 C46 1.463(2) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9814743
