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#$Date: 2022-09-14 23:33:16 +0300 (Wed, 14 Sep 2022) $
#$Revision: 277842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/02/4020271.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_4020271
loop_
_publ_author_name
'Sukhdev Manku'
'Dennis P. Curran'
_publ_section_title
;
Fluorous Mixture Synthesis of Fused-Tricyclic Hydantoins. Use of a Redundant 
Tagging Strategy on Fluorinated Substrates
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4470
_journal_page_last               4473
_journal_paper_doi               10.1021/jo0502596
_journal_volume                  70
_journal_year                    2005
_chemical_formula_sum            'C33 H30 N2 O3'
_chemical_formula_weight         2010.36
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                101.088(2)
_cell_angle_beta                 90.658(2)
_cell_angle_gamma                104.314(2)
_cell_formula_units_Z            4
_cell_length_a                   10.6129(8)
_cell_length_b                   12.1178(9)
_cell_length_c                   22.3579(17)
_cell_measurement_temperature    293(2)
_cell_volume                     2728.8(4)
_diffrn_ambient_temperature      293(2)
_exptl_crystal_density_diffrn    1.223
_cod_database_code               4020271
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
O1 O 0.1975(5) 0.8665(4) 0.1946(2) 0.0600(14) Uani 1 1 d . . .
N1 N 0.2933(5) 0.7522(4) 0.2400(2) 0.0427(14) Uani 1 1 d . . .
C1 C 0.1982(7) 0.7746(6) 0.2071(3) 0.0493(19) Uani 1 1 d . . .
C2 C 0.0866(6) 0.6628(5) 0.1926(3) 0.0369(16) Uani 1 1 d . . .
N2 N 0.1394(5) 0.5869(4) 0.2254(2) 0.0359(13) Uani 1 1 d . . .
O2 O -0.2099(6) 0.4270(5) 0.0264(3) 0.0840(18) Uani 1 1 d . . .
O3 O 0.3374(4) 0.5916(4) 0.2688(2) 0.0550(14) Uani 1 1 d . . .
C3 C 0.0683(7) 0.5918(5) 0.1258(3) 0.0453(18) Uani 1 1 d . . .
H3A H 0.1522 0.6058 0.1070 0.054 Uiso 1 1 calc R . .
C4 C -0.0382(7) 0.5896(6) 0.0797(3) 0.0476(18) Uani 1 1 d . . .
C5 C -0.1176(8) 0.4674(7) 0.0625(3) 0.056(2) Uani 1 1 d . . .
C6 C -0.0676(7) 0.3977(6) 0.1000(3) 0.054(2) Uani 1 1 d . . .
C7 C 0.0330(7) 0.4709(6) 0.1371(3) 0.0501(19) Uani 1 1 d . . .
C8 C 0.0965(6) 0.4636(5) 0.1943(3) 0.0434(18) Uani 1 1 d . . .
H8A H 0.1700 0.4297 0.1866 0.052 Uiso 1 1 calc R . .
H8B H 0.0357 0.4184 0.2179 0.052 Uiso 1 1 calc R . .
C9 C 0.2644(7) 0.6374(6) 0.2467(3) 0.0421(18) Uani 1 1 d . . .
C10 C 0.4143(7) 0.8365(6) 0.2636(3) 0.058(2) Uani 1 1 d . . .
H10A H 0.4596 0.8044 0.2912 0.070 Uiso 1 1 calc R . .
H10B H 0.3944 0.9056 0.2870 0.070 Uiso 1 1 calc R . .
C11 C 0.5034(8) 0.8708(8) 0.2149(5) 0.091(3) Uani 1 1 d . . .
H11A H 0.4673 0.9200 0.1938 0.109 Uiso 1 1 calc R . .
H11B H 0.5870 0.9168 0.2344 0.109 Uiso 1 1 calc R . .
C12 C 0.5247(7) 0.7743(7) 0.1701(4) 0.056(2) Uani 1 1 d . . .
C13 C 0.4588(10) 0.7404(12) 0.1148(6) 0.118(4) Uani 1 1 d . . .
H13A H 0.4043 0.7841 0.1044 0.141 Uiso 1 1 calc R . .
C14 C 0.4690(11) 0.6448(14) 0.0737(6) 0.133(5) Uani 1 1 d . . .
H14A H 0.4211 0.6233 0.0364 0.160 Uiso 1 1 calc R . .
C15 C 0.5501(12) 0.5808(12) 0.0879(6) 0.132(5) Uani 1 1 d . . .
H15A H 0.5562 0.5149 0.0600 0.158 Uiso 1 1 calc R . .
C16 C 0.6230(10) 0.6120(10) 0.1426(6) 0.104(3) Uani 1 1 d . . .
H16A H 0.6799 0.5695 0.1518 0.125 Uiso 1 1 calc R . .
C17 C 0.6082(9) 0.7101(8) 0.1840(4) 0.082(3) Uani 1 1 d . . .
H17A H 0.6555 0.7325 0.2215 0.098 Uiso 1 1 calc R . .
C18 C -0.0394(6) 0.6864(6) 0.2175(3) 0.0469(19) Uani 1 1 d . . .
H18A H -0.0738 0.7288 0.1913 0.056 Uiso 1 1 calc R . .
H18B H -0.1028 0.6127 0.2157 0.056 Uiso 1 1 calc R . .
C19 C -0.0239(6) 0.7544(6) 0.2818(3) 0.0477(19) Uani 1 1 d . . .
C20 C -0.0146(6) 0.7001(7) 0.3305(4) 0.057(2) Uani 1 1 d . . .
H20A H -0.0208 0.6207 0.3230 0.068 Uiso 1 1 calc R . .
C21 C 0.0036(8) 0.7622(9) 0.3889(5) 0.084(3) Uani 1 1 d . . .
H21A H 0.0096 0.7238 0.4207 0.100 Uiso 1 1 calc R . .
C22 C 0.0134(10) 0.8794(11) 0.4025(5) 0.103(4) Uani 1 1 d . . .
H22A H 0.0252 0.9207 0.4426 0.124 Uiso 1 1 calc R . .
C23 C 0.0051(9) 0.9334(8) 0.3542(5) 0.094(3) Uani 1 1 d . . .
H23A H 0.0132 1.0131 0.3617 0.113 Uiso 1 1 calc R . .
C24 C -0.0148(8) 0.8716(7) 0.2950(4) 0.075(3) Uani 1 1 d . . .
H24A H -0.0222 0.9099 0.2634 0.090 Uiso 1 1 calc R . .
C25 C -0.0503(8) 0.6745(7) 0.0522(3) 0.059(2) Uani 1 1 d . . .
C26 C 0.0439(9) 0.7906(7) 0.0650(3) 0.081(3) Uani 1 1 d . . .
H26A H 0.1126 0.7904 0.0933 0.121 Uiso 1 1 calc R . .
H26B H 0.0000 0.8485 0.0824 0.121 Uiso 1 1 calc R . .
H26C H 0.0800 0.8079 0.0277 0.121 Uiso 1 1 calc R . .
C27 C -0.1616(9) 0.6657(8) 0.0071(4) 0.094(3) Uani 1 1 d . . .
H27A H -0.2192 0.5891 0.0007 0.141 Uiso 1 1 calc R . .
H27B H -0.1276 0.6803 -0.0311 0.141 Uiso 1 1 calc R . .
H27C H -0.2087 0.7220 0.0229 0.141 Uiso 1 1 calc R . .
C28 C -0.1239(9) 0.2706(7) 0.0982(3) 0.062(2) Uani 1 1 d . . .
C29 C -0.2536(9) 0.2168(9) 0.0833(4) 0.088(3) Uani 1 1 d . . .
H29A H -0.3106 0.2604 0.0756 0.106 Uiso 1 1 calc R . .
C30 C -0.3000(12) 0.0983(10) 0.0796(5) 0.116(4) Uani 1 1 d . . .
H30A H -0.3872 0.0616 0.0686 0.139 Uiso 1 1 calc R . .
C31 C -0.2149(13) 0.0358(9) 0.0925(5) 0.100(4) Uani 1 1 d . . .
H31A H -0.2458 -0.0438 0.0900 0.120 Uiso 1 1 calc R . .
C32 C -0.0871(12) 0.0868(7) 0.1087(4) 0.093(3) Uani 1 1 d . . .
H32A H -0.0318 0.0432 0.1184 0.111 Uiso 1 1 calc R . .
C33 C -0.0405(9) 0.2048(7) 0.1107(3) 0.070(2) Uani 1 1 d . . .
H33A H 0.0475 0.2403 0.1205 0.084 Uiso 1 1 calc R . .
N3 N 0.6618(5) 0.2529(4) 0.2641(2) 0.0390(14) Uani 1 1 d . . .
N4 N 0.5979(5) 0.4167(4) 0.2812(2) 0.0329(13) Uani 1 1 d . . .
O4 O 0.5028(4) 0.1311(4) 0.3047(2) 0.0511(13) Uani 1 1 d . . .
O5 O 0.3289(5) 0.5550(4) 0.4802(2) 0.0657(15) Uani 1 1 d . . .
O6 O 0.7975(4) 0.4197(4) 0.2417(2) 0.0518(13) Uani 1 1 d . . .
C34 C 0.5514(6) 0.2265(6) 0.2947(3) 0.0375(16) Uani 1 1 d . . .
C35 C 0.4994(6) 0.3338(5) 0.3096(3) 0.0326(16) Uani 1 1 d . . .
C36 C 0.5138(6) 0.3986(5) 0.3777(3) 0.0390(17) Uani 1 1 d . . .
H36A H 0.5874 0.3825 0.3982 0.047 Uiso 1 1 calc R . .
C37 C 0.4048(7) 0.3964(6) 0.4203(3) 0.0409(18) Uani 1 1 d . . .
C38 C 0.3977(7) 0.5206(6) 0.4432(3) 0.0465(18) Uani 1 1 d . . .
C39 C 0.4889(7) 0.5921(6) 0.4080(3) 0.0486(19) Uani 1 1 d . . .
C40 C 0.5511(7) 0.5238(6) 0.3700(3) 0.0441(18) Uani 1 1 d . . .
C41 C 0.6219(6) 0.5378(5) 0.3148(3) 0.0425(18) Uani 1 1 d . . .
H41A H 0.7142 0.5726 0.3248 0.051 Uiso 1 1 calc R . .
H41B H 0.5873 0.5848 0.2917 0.051 Uiso 1 1 calc R . .
C42 C 0.6957(7) 0.3701(7) 0.2607(3) 0.0443(18) Uani 1 1 d . . .
C43 C 0.7419(7) 0.1735(6) 0.2429(3) 0.052(2) Uani 1 1 d . . .
H43A H 0.8062 0.2089 0.2172 0.063 Uiso 1 1 calc R . .
H43B H 0.6871 0.1030 0.2181 0.063 Uiso 1 1 calc R . .
C44 C 0.8113(8) 0.1415(6) 0.2936(4) 0.064(2) Uani 1 1 d . . .
H44A H 0.7478 0.0968 0.3164 0.077 Uiso 1 1 calc R . .
H44B H 0.8677 0.0934 0.2763 0.077 Uiso 1 1 calc R . .
C45 C 0.8906(7) 0.2479(7) 0.3358(4) 0.051(2) Uani 1 1 d . . .
C46 C 0.8407(8) 0.2959(9) 0.3883(4) 0.074(3) Uani 1 1 d . . .
H46A H 0.7620 0.2563 0.4007 0.089 Uiso 1 1 calc R . .
C47 C 0.9068(9) 0.4018(10) 0.4222(4) 0.086(3) Uani 1 1 d . . .
H47A H 0.8697 0.4342 0.4565 0.104 Uiso 1 1 calc R . .
C48 C 1.0264(9) 0.4617(8) 0.4070(4) 0.073(3) Uani 1 1 d . . .
H48A H 1.0708 0.5334 0.4302 0.088 Uiso 1 1 calc R . .
C49 C 1.0765(7) 0.4103(8) 0.3562(4) 0.068(2) Uani 1 1 d . . .
H49A H 1.1581 0.4473 0.3454 0.082 Uiso 1 1 calc R . .
C50 C 1.0112(8) 0.3066(8) 0.3208(4) 0.063(2) Uani 1 1 d . . .
H50A H 1.0481 0.2752 0.2862 0.075 Uiso 1 1 calc R . .
C51 C 0.3619(6) 0.3110(5) 0.2798(3) 0.0423(18) Uani 1 1 d . . .
H51A H 0.3017 0.2577 0.2998 0.051 Uiso 1 1 calc R . .
H51B H 0.3360 0.3836 0.2865 0.051 Uiso 1 1 calc R . .
C52 C 0.3502(6) 0.2615(6) 0.2125(3) 0.0359(16) Uani 1 1 d . . .
C53 C 0.3879(6) 0.3303(6) 0.1699(3) 0.0472(19) Uani 1 1 d . . .
H53A H 0.4200 0.4101 0.1833 0.057 Uiso 1 1 calc R . .
C54 C 0.3795(8) 0.2848(9) 0.1092(4) 0.071(2) Uani 1 1 d . . .
H54A H 0.4054 0.3334 0.0817 0.085 Uiso 1 1 calc R . .
C55 C 0.3324(9) 0.1657(9) 0.0881(4) 0.084(3) Uani 1 1 d . . .
H55A H 0.3257 0.1338 0.0465 0.101 Uiso 1 1 calc R . .
C56 C 0.2957(9) 0.0957(8) 0.1304(4) 0.084(3) Uani 1 1 d . . .
H56A H 0.2641 0.0158 0.1171 0.100 Uiso 1 1 calc R . .
C57 C 0.3052(7) 0.1423(6) 0.1913(4) 0.058(2) Uani 1 1 d . . .
H57A H 0.2813 0.0937 0.2190 0.069 Uiso 1 1 calc R . .
C58 C 0.3327(7) 0.3045(7) 0.4409(3) 0.053(2) Uani 1 1 d . . .
C59 C 0.3564(8) 0.1856(6) 0.4238(4) 0.075(3) Uani 1 1 d . . .
H59A H 0.4292 0.1886 0.3986 0.113 Uiso 1 1 calc R . .
H59B H 0.2803 0.1323 0.4019 0.113 Uiso 1 1 calc R . .
H59C H 0.3749 0.1597 0.4602 0.113 Uiso 1 1 calc R . .
C60 C 0.2204(8) 0.3101(7) 0.4816(3) 0.077(3) Uani 1 1 d . . .
H60A H 0.2112 0.3883 0.4909 0.115 Uiso 1 1 calc R . .
H60B H 0.2374 0.2863 0.5188 0.115 Uiso 1 1 calc R . .
H60C H 0.1415 0.2591 0.4610 0.115 Uiso 1 1 calc R . .
C61 C 0.5049(8) 0.7185(6) 0.4108(3) 0.0509(19) Uani 1 1 d . . .
C62 C 0.4039(8) 0.7684(6) 0.4256(4) 0.072(2) Uani 1 1 d . . .
H62A H 0.3237 0.7232 0.4334 0.086 Uiso 1 1 calc R . .
C63 C 0.4221(10) 0.8867(8) 0.4289(4) 0.087(3) Uani 1 1 d . . .
H63A H 0.3530 0.9200 0.4387 0.104 Uiso 1 1 calc R . .
C64 C 0.5410(11) 0.9567(7) 0.4180(4) 0.079(3) Uani 1 1 d . . .
H64A H 0.5525 1.0362 0.4208 0.095 Uiso 1 1 calc R . .
C65 C 0.6402(10) 0.9059(7) 0.4030(3) 0.072(3) Uani 1 1 d . . .
H65A H 0.7204 0.9510 0.3951 0.087 Uiso 1 1 calc R . .
C66 C 0.6234(8) 0.7877(7) 0.3993(3) 0.060(2) Uani 1 1 d . . .
H66A H 0.6924 0.7545 0.3891 0.072 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
O1 C1 1.201(7) . ?
N1 C1 1.352(8) . ?
N1 C9 1.387(8) . ?
N1 C10 1.449(7) . ?
C1 C2 1.541(9) . ?
C2 N2 1.485(7) . ?
C2 C18 1.524(8) . ?
C2 C3 1.557(9) . ?
N2 C9 1.354(8) . ?
N2 C8 1.476(7) . ?
O2 C5 1.201(8) . ?
O3 C9 1.207(7) . ?
C3 C7 1.491(8) . ?
C3 C4 1.512(9) . ?
C3 H3A 0.9800 . ?
C4 C25 1.327(9) . ?
C4 C5 1.486(9) . ?
C5 C6 1.477(10) . ?
C6 C7 1.358(9) . ?
C6 C28 1.500(10) . ?
C7 C8 1.466(9) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C10 C11 1.502(10) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.452(11) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.351(12) . ?
C12 C17 1.385(11) . ?
C13 C14 1.361(15) . ?
C13 H13A 0.9300 . ?
C14 C15 1.363(16) . ?
C14 H14A 0.9300 . ?
C15 C16 1.376(14) . ?
C15 H15A 0.9300 . ?
C16 C17 1.402(12) . ?
C16 H16A 0.9300 . ?
C17 H17A 0.9300 . ?
C18 C19 1.498(9) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C24 1.373(9) . ?
C19 C20 1.390(9) . ?
C20 C21 1.362(10) . ?
C20 H20A 0.9300 . ?
C21 C22 1.371(12) . ?
C21 H21A 0.9300 . ?
C22 C23 1.378(12) . ?
C22 H22A 0.9300 . ?
C23 C24 1.374(11) . ?
C23 H23A 0.9300 . ?
C24 H24A 0.9300 . ?
C25 C26 1.485(10) . ?
C25 C27 1.514(9) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 C29 1.376(10) . ?
C28 C33 1.389(10) . ?
C29 C30 1.384(12) . ?
C29 H29A 0.9300 . ?
C30 C31 1.374(13) . ?
C30 H30A 0.9300 . ?
C31 C32 1.357(12) . ?
C31 H31A 0.9300 . ?
C32 C33 1.384(10) . ?
C32 H32A 0.9300 . ?
C33 H33A 0.9300 . ?
N3 C34 1.365(8) . ?
N3 C42 1.394(8) . ?
N3 C43 1.452(7) . ?
N4 C42 1.344(7) . ?
N4 C41 1.473(7) . ?
N4 C35 1.498(7) . ?
O4 C34 1.208(7) . ?
O5 C38 1.192(7) . ?
O6 C42 1.223(7) . ?
C34 C35 1.515(8) . ?
C35 C51 1.536(8) . ?
C35 C36 1.561(8) . ?
C36 C37 1.506(9) . ?
C36 C40 1.514(8) . ?
C36 H36A 0.9800 . ?
C37 C58 1.349(9) . ?
C37 C38 1.514(9) . ?
C38 C39 1.475(9) . ?
C39 C40 1.361(8) . ?
C39 C61 1.488(9) . ?
C40 C41 1.468(8) . ?
C41 H41A 0.9700 . ?
C41 H41B 0.9700 . ?
C43 C44 1.506(9) . ?
C43 H43A 0.9700 . ?
C43 H43B 0.9700 . ?
C44 C45 1.496(10) . ?
C44 H44A 0.9700 . ?
C44 H44B 0.9700 . ?
C45 C46 1.377(10) . ?
C45 C50 1.382(10) . ?
C46 C47 1.372(12) . ?
C46 H46A 0.9300 . ?
C47 C48 1.379(11) . ?
C47 H47A 0.9300 . ?
C48 C49 1.365(10) . ?
C48 H48A 0.9300 . ?
C49 C50 1.364(10) . ?
C49 H49A 0.9300 . ?
C50 H50A 0.9300 . ?
C51 C52 1.500(8) . ?
C51 H51A 0.9700 . ?
C51 H51B 0.9700 . ?
C52 C53 1.382(8) . ?
C52 C57 1.389(9) . ?
C53 C54 1.357(9) . ?
C53 H53A 0.9300 . ?
C54 C55 1.389(11) . ?
C54 H54A 0.9300 . ?
C55 C56 1.386(11) . ?
C55 H55A 0.9300 . ?
C56 C57 1.362(10) . ?
C56 H56A 0.9300 . ?
C57 H57A 0.9300 . ?
C58 C59 1.502(9) . ?
C58 C60 1.515(9) . ?
C59 H59A 0.9600 . ?
C59 H59B 0.9600 . ?
C59 H59C 0.9600 . ?
C60 H60A 0.9600 . ?
C60 H60B 0.9600 . ?
C60 H60C 0.9600 . ?
C61 C62 1.369(9) . ?
C61 C66 1.386(9) . ?
C62 C63 1.386(10) . ?
C62 H62A 0.9300 . ?
C63 C64 1.389(11) . ?
C63 H63A 0.9300 . ?
C64 C65 1.360(11) . ?
C64 H64A 0.9300 . ?
C65 C66 1.384(10) . ?
C65 H65A 0.9300 . ?
C66 H66A 0.9300 . ?
