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#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/59/7105982.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_7105982
loop_
_publ_author_name
'Lingling Rong'
'Qiancai Liu'
'Yingbo Shi'
'Jie Tang'
_publ_section_title
;
 Fluoradenes via palladium-catalyzed intramolecular arylation
;
_journal_name_full               Chem.Commun.
_journal_page_first              2155
_journal_paper_doi               10.1039/c0cc05004k
_journal_volume                  47
_journal_year                    2011
_chemical_formula_sum            'C54 H29 N O2'
_chemical_formula_weight         723.780
_space_group_IT_number           11
_symmetry_Int_Tables_number      11
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 1'
_audit_creation_date             2010-09-28
_audit_creation_method           SHELXL-97
_audit_update_record             2010-09-28
_cell_angle_alpha                90.000
_cell_angle_beta                 117.935(1)
_cell_angle_gamma                90.000
_cell_formula_units_Z            2
_cell_length_a                   8.3866(3)
_cell_length_b                   28.4107(9)
_cell_length_c                   8.9081(4)
_cell_volume                     1875.21(12)
_refine_ls_R_factor_all          0.049
_cod_data_source_file            C0CC05004K.TXT
_cod_data_source_block           z1
_cod_original_cell_volume        1875.2(1)
_cod_original_sg_symbol_Hall     -P_2yb
_cod_database_code               7105982
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,0.500+y,-z
3 -x,-y,-z
4 x,0.500-y,z
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_Wyckoff_symbol
_atom_site_attached_hydrogens
_atom_site_calc_flag
_atom_site_thermal_displace_type
_atom_site_U_iso_or_equiv
N1 N 0.0416(4) 0.2500 0.1027(3) 1.000 2 e ? d Uani 0.0498(6)
H1A H 0.072(4) 0.2500 0.203(4) 1.000 2 e ? d Uiso 0.059(9)
C1 C 0.2857(2) 0.0542(1) -0.2268(2) 1.000 4 f ? d Uani 0.0413(4)
C2 C 0.4639(2) 0.0413(1) -0.1703(2) 1.000 4 f ? d Uani 0.0503(5)
H2A H 0.5057 0.0125 -0.1159 1.000 4 f ? calc Uiso 0.06000
C3 C 0.5792(3) 0.0712(1) -0.1953(3) 1.000 4 f ? d Uani 0.0570(5)
H3A H 0.6992 0.0626 -0.1560 1.000 4 f ? calc Uiso 0.06800
C4 C 0.5193(3) 0.1134(1) -0.2770(3) 1.000 4 f ? d Uani 0.0594(5)
H4A H 0.5985 0.1329 -0.2939 1.000 4 f ? calc Uiso 0.07100
C5 C 0.3402(3) 0.1274(1) -0.3351(2) 1.000 4 f ? d Uani 0.0501(4)
H5A H 0.3000 0.1561 -0.3898 1.000 4 f ? calc Uiso 0.06000
C6 C 0.2244(2) 0.0980(1) -0.3102(2) 1.000 4 f ? d Uani 0.0397(4)
C7 C 0.0277(2) 0.1061(0) -0.3493(2) 1.000 4 f ? d Uani 0.0365(4)
C8 C -0.0168(2) 0.0576(0) -0.3148(2) 1.000 4 f ? d Uani 0.0378(4)
C9 C 0.1292(2) 0.0279(1) -0.2351(2) 1.000 4 f ? d Uani 0.0408(4)
C10 C 0.0910(3) -0.0193(1) -0.2227(2) 1.000 4 f ? d Uani 0.0488(4)
H10A H 0.1831 -0.0408 -0.1632 1.000 4 f ? calc Uiso 0.05900
C11 C -0.0891(3) -0.0334(1) -0.3019(2) 1.000 4 f ? d Uani 0.0509(5)
H11A H -0.1168 -0.0640 -0.2840 1.000 4 f ? calc Uiso 0.06100
C12 C -0.2293(3) -0.0038(1) -0.4066(2) 1.000 4 f ? d Uani 0.0485(4)
H12A H -0.3465 -0.0152 -0.4669 1.000 4 f ? calc Uiso 0.05800
C13 C -0.1908(2) 0.0433(1) -0.4193(2) 1.000 4 f ? d Uani 0.0409(4)
C14 C -0.2703(2) 0.0805(1) -0.5511(2) 1.000 4 f ? d Uani 0.0425(4)
C15 C -0.1339(2) 0.1140(1) -0.5251(2) 1.000 4 f ? d Uani 0.0395(4)
C16 C -0.1613(3) 0.1472(1) -0.6469(2) 1.000 4 f ? d Uani 0.0488(4)
H16A H -0.0714 0.1689 -0.6306 1.000 4 f ? calc Uiso 0.05900
C17 C -0.3257(3) 0.1480(1) -0.7950(2) 1.000 4 f ? d Uani 0.0611(5)
H17A H -0.3441 0.1695 -0.8802 1.000 4 f ? calc Uiso 0.07300
C18 C -0.4613(3) 0.1172(1) -0.8166(3) 1.000 4 f ? d Uani 0.0641(6)
H18A H -0.5721 0.1192 -0.9140 1.000 4 f ? calc Uiso 0.07700
C19 C -0.4357(3) 0.0831(1) -0.6957(2) 1.000 4 f ? d Uani 0.0543(5)
H19A H -0.5282 0.0625 -0.7115 1.000 4 f ? calc Uiso 0.06500
C20 C 0.0264(2) 0.1435(0) -0.2235(2) 1.000 4 f ? d Uani 0.0354(4)
C21 C 0.0393(2) 0.1303(1) -0.0668(2) 1.000 4 f ? d Uani 0.0407(4)
H21A H 0.0440 0.0984 -0.0410 1.000 4 f ? calc Uiso 0.04900
C22 C 0.0453(3) 0.1629(1) 0.0509(2) 1.000 4 f ? d Uani 0.0468(4)
H22A H 0.0535 0.1534 0.1541 1.000 4 f ? calc Uiso 0.05600
C23 C 0.0387(2) 0.2104(1) 0.0109(2) 1.000 4 f ? d Uani 0.0405(4)
C24 C 0.0264(2) 0.2245(0) -0.1449(2) 1.000 4 f ? d Uani 0.0366(4)
C25 C 0.0200(2) 0.1909(1) -0.2613(2) 1.000 4 f ? d Uani 0.0393(4)
H25A H 0.0115 0.2003 -0.3648 1.000 4 f ? calc Uiso 0.04700
O01 O 0.253(3) 0.2500 0.514(3) 0.500 2 e ? d Uani 0.094(5)
O02 O 0.546(5) 0.2305(10) 0.626(3) 0.250 4 f ? d Uani 0.076(5)
C01 C 0.478(4) 0.2500 0.820(4) 0.500 2 e ? d Uani 0.085(6)
C02 C 0.393(4) 0.2500 0.625(3) 0.500 2 e ? d Uani 0.062(3)
C03 C 0.477(3) 0.2141(10) 0.410(3) 0.250 4 f ? d Uani 0.086(6)
C04 C 0.559(3) 0.2500 0.375(2) 0.500 2 e ? d Uani 0.107(4)
O01' O 0.2491(17) 0.2500 0.514(2) 0.500 2 e ? d Uani 0.054(3)
C01' C 0.439(4) 0.2500 0.809(4) 0.500 2 e ? d Uani 0.075(6)
C02' C 0.414(5) 0.2500 0.636(4) 0.500 2 e ? d Uani 0.085(5)
O02' O 0.529(4) 0.2747(10) 0.598(3) 0.250 4 f ? d Uani 0.063(3)
C03' C 0.517(3) 0.2845(9) 0.449(3) 0.250 4 f ? d Uani 0.066(4)
C04' C 0.505(3) 0.2500 0.321(2) 0.500 2 e ? d Uani 0.115(5)
loop_
_atom_type_symbol
_atom_type_oxidation_number
_atom_type_radius_bond
N ? 1.200
H ? 1.200
C ? 1.200
O ? 1.200
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C23 N1 C23 . . 4 108.79(19) no
C23 N1 H1A . . . 124.3(4) no
C23 N1 H1A 4 . . 124.3(4) no
C2 C1 C6 . . . 119.30(16) no
C2 C1 C9 . . . 131.52(17) no
C6 C1 C9 . . . 108.80(14) no
C3 C2 C1 . . . 119.66(18) no
C3 C2 H2A . . . 120.20 no
C1 C2 H2A . . . 120.20 no
C4 C3 C2 . . . 120.96(18) no
C4 C3 H3A . . . 119.50 no
C2 C3 H3A . . . 119.50 no
C3 C4 C5 . . . 120.56(19) no
C3 C4 H4A . . . 119.70 no
C5 C4 H4A . . . 119.70 no
C6 C5 C4 . . . 119.07(18) no
C6 C5 H5A . . . 120.50 no
C4 C5 H5A . . . 120.50 no
C5 C6 C1 . . . 120.45(16) no
C5 C6 C7 . . . 129.70(16) no
C1 C6 C7 . . . 109.71(14) no
C8 C7 C15 . . . 99.14(13) no
C8 C7 C6 . . . 99.29(13) no
C15 C7 C6 . . . 126.53(13) no
C8 C7 C20 . . . 113.40(13) no
C15 C7 C20 . . . 109.57(12) no
C6 C7 C20 . . . 108.02(12) no
C13 C8 C9 . . . 124.90(15) no
C13 C8 C7 . . . 114.92(15) no
C9 C8 C7 . . . 115.05(14) no
C8 C9 C10 . . . 116.65(16) no
C8 C9 C1 . . . 105.50(14) no
C10 C9 C1 . . . 135.44(16) no
C11 C10 C9 . . . 118.11(17) no
C11 C10 H10A . . . 120.90 no
C9 C10 H10A . . . 120.90 no
C12 C11 C10 . . . 122.72(17) no
C12 C11 H11A . . . 118.60 no
C10 C11 H11A . . . 118.60 no
C11 C12 C13 . . . 118.75(17) no
C11 C12 H12A . . . 120.60 no
C13 C12 H12A . . . 120.60 no
C8 C13 C12 . . . 116.22(16) no
C8 C13 C14 . . . 105.45(14) no
C12 C13 C14 . . . 135.36(16) no
C19 C14 C15 . . . 119.60(17) no
C19 C14 C13 . . . 131.16(17) no
C15 C14 C13 . . . 108.58(14) no
C16 C15 C14 . . . 120.53(16) no
C16 C15 C7 . . . 130.41(16) no
C14 C15 C7 . . . 109.04(14) no
C15 C16 C17 . . . 118.93(19) no
C15 C16 H16A . . . 120.50 no
C17 C16 H16A . . . 120.50 no
C18 C17 C16 . . . 120.64(19) no
C18 C17 H17A . . . 119.70 no
C16 C17 H17A . . . 119.70 no
C17 C18 C19 . . . 121.22(18) no
C17 C18 H18A . . . 119.40 no
C19 C18 H18A . . . 119.40 no
C14 C19 C18 . . . 118.93(19) no
C14 C19 H19A . . . 120.50 no
C18 C19 H19A . . . 120.50 no
C25 C20 C21 . . . 118.78(14) no
C25 C20 C7 . . . 120.35(14) no
C21 C20 C7 . . . 120.81(14) no
C22 C21 C20 . . . 122.20(15) no
C22 C21 H21A . . . 118.90 no
C20 C21 H21A . . . 118.90 no
C21 C22 C23 . . . 118.31(15) no
C21 C22 H22A . . . 120.80 no
C23 C22 H22A . . . 120.80 no
N1 C23 C22 . . . 130.57(16) no
N1 C23 C24 . . . 108.91(15) no
C22 C23 C24 . . . 120.52(15) no
C25 C24 C23 . . . 120.04(14) no
C25 C24 C24 . . 4 133.29(9) no
C23 C24 C24 . . 4 106.66(9) no
C20 C25 C24 . . . 120.15(15) no
C20 C25 H25A . . . 119.90 no
C24 C25 H25A . . . 119.90 no
O02 O02 C02 4 . . 66.5(13) no
O02 O02 C03 4 . . 105.1(13) no
C02 O02 C03 . . . 105.(2) no
O01 C02 O02 . . 4 126.(2) no
O01 C02 O02 . . . 126.(2) no
O02 C02 O02 4 . . 47.(3) no
O01 C02 C01 . . . 137.(2) no
O02 C02 C01 4 . . 93.(3) no
O02 C02 C01 . . . 93.(3) no
C04 C03 O02 . . . 96.(2) no
C03 C04 C03 . . 4 99.(3) no
O01' C02' O02' . . 4 113.(2) no
O01' C02' O02' . . . 113.(2) no
O02' C02' O02' 4 . . 63.(3) no
O01' C02' C01' . . . 117.(3) no
O02' C02' C01' 4 . . 120.(3) no
O02' C02' C01' . . . 120.(3) no
C03' O02' C02' . . . 129.(3) no
C03' O02' O02' . . 4 102.2(17) no
C02' O02' O02' . . 4 58.7(15) no
O02' C03' C04' . . . 126.(2) no
O02' C03' C03' . . 4 77.8(17) no
C04' C03' C03' . . 4 48.3(13) no
C03' C04' C03' . . 4 83.(3) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C23 . . 1.386(2) no
N1 C23 . 4 1.386(2) no
N1 H1A . . 0.81(3) no
C1 C2 . . 1.385(2) no
C1 C6 . . 1.417(2) no
C1 C9 . . 1.482(2) no
C2 C3 . . 1.382(3) no
C2 H2A . . 0.9300 no
C3 C4 . . 1.369(3) no
C3 H3A . . 0.9300 no
C4 C5 . . 1.398(3) no
C4 H4A . . 0.9300 no
C5 C6 . . 1.374(2) no
C5 H5A . . 0.9300 no
C6 C7 . . 1.535(2) no
C7 C8 . . 1.495(2) no
C7 C15 . . 1.534(2) no
C7 C20 . . 1.550(2) no
C8 C13 . . 1.374(2) no
C8 C9 . . 1.380(2) no
C9 C10 . . 1.396(2) no
C10 C11 . . 1.393(3) no
C10 H10A . . 0.9300 no
C11 C12 . . 1.391(3) no
C11 H11A . . 0.9300 no
C12 C13 . . 1.394(2) no
C12 H12A . . 0.9300 no
C13 C14 . . 1.484(2) no
C14 C19 . . 1.384(2) no
C14 C15 . . 1.422(2) no
C15 C16 . . 1.373(2) no
C16 C17 . . 1.392(3) no
C16 H16A . . 0.9300 no
C17 C18 . . 1.375(3) no
C17 H17A . . 0.9300 no
C18 C19 . . 1.387(3) no
C18 H18A . . 0.9300 no
C19 H19A . . 0.9300 no
C20 C25 . . 1.382(2) no
C20 C21 . . 1.400(2) no
C21 C22 . . 1.384(2) no
C21 H21A . . 0.9300 no
C22 C23 . . 1.387(2) no
C22 H22A . . 0.9300 no
C23 C24 . . 1.402(2) no
C24 C25 . . 1.392(2) no
C24 C24 . 4 1.449(3) no
C25 H25A . . 0.9300 no
O01 C02 . . 1.12(4) no
O02 O02 . 4 1.11(6) no
O02 C02 . . 1.39(5) no
O02 C03 . . 1.79(4) no
C01 C02 . . 1.54(5) no
C02 O02 . 4 1.39(5) no
C03 C04 . . 1.35(3) no
C04 C03 . 4 1.35(3) no
O01' C02' . . 1.30(4) no
C01' C02' . . 1.46(5) no
C02' O02' . 4 1.35(5) no
C02' O02' . . 1.35(5) no
O02' C03' . . 1.31(4) no
O02' O02' . 4 1.41(5) no
C03' C04' . . 1.47(3) no
C03' C03' . 4 1.96(5) no
C04' C03' . 4 1.47(3) no
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . 0.3(2) no
C9 C1 C2 C3 . . . . 172.34(17) no
C1 C2 C3 C4 . . . . -0.8(3) no
C2 C3 C4 C5 . . . . 0.9(3) no
C3 C4 C5 C6 . . . . -0.5(3) no
C4 C5 C6 C1 . . . . 0.0(3) no
C4 C5 C6 C7 . . . . 175.21(17) no
C2 C1 C6 C5 . . . . 0.0(2) no
C9 C1 C6 C5 . . . . -173.63(15) no
C2 C1 C6 C7 . . . . -176.02(14) no
C9 C1 C6 C7 . . . . 10.30(17) no
C5 C6 C7 C8 . . . . 171.76(17) no
C1 C6 C7 C8 . . . . -12.65(16) no
C5 C6 C7 C15 . . . . 63.0(2) no
C1 C6 C7 C15 . . . . -121.40(16) no
C5 C6 C7 C20 . . . . -69.8(2) no
C1 C6 C7 C20 . . . . 105.80(15) no
C15 C7 C8 C13 . . . . -14.96(17) no
C6 C7 C8 C13 . . . . -144.55(14) no
C20 C7 C8 C13 . . . . 101.10(16) no
C15 C7 C8 C9 . . . . 141.01(14) no
C6 C7 C8 C9 . . . . 11.43(17) no
C20 C7 C8 C9 . . . . -102.93(16) no
C13 C8 C9 C10 . . . . -17.9(3) no
C7 C8 C9 C10 . . . . -171.10(14) no
C13 C8 C9 C1 . . . . 147.26(16) no
C7 C8 C9 C1 . . . . -5.98(18) no
C2 C1 C9 C8 . . . . -175.56(17) no
C6 C1 C9 C8 . . . . -2.93(17) no
C2 C1 C9 C10 . . . . -14.7(3) no
C6 C1 C9 C10 . . . . 157.98(19) no
C8 C9 C10 C11 . . . . 4.7(2) no
C1 C9 C10 C11 . . . . -154.63(18) no
C9 C10 C11 C12 . . . . 6.9(3) no
C10 C11 C12 C13 . . . . -6.8(3) no
C9 C8 C13 C12 . . . . 18.0(2) no
C7 C8 C13 C12 . . . . 171.27(14) no
C9 C8 C13 C14 . . . . -145.57(16) no
C7 C8 C13 C14 . . . . 7.70(18) no
C11 C12 C13 C8 . . . . -5.1(2) no
C11 C12 C13 C14 . . . . 152.06(19) no
C8 C13 C14 C19 . . . . 174.38(18) no
C12 C13 C14 C19 . . . . 15.6(3) no
C8 C13 C14 C15 . . . . 3.98(17) no
C12 C13 C14 C15 . . . . -154.84(19) no
C19 C14 C15 C16 . . . . -3.8(2) no
C13 C14 C15 C16 . . . . 167.84(15) no
C19 C14 C15 C7 . . . . 174.74(15) no
C13 C14 C15 C7 . . . . -13.57(17) no
C8 C7 C15 C16 . . . . -165.03(17) no
C6 C7 C15 C16 . . . . -56.2(3) no
C20 C7 C15 C16 . . . . 76.0(2) no
C8 C7 C15 C14 . . . . 16.57(16) no
C6 C7 C15 C14 . . . . 125.40(17) no
C20 C7 C15 C14 . . . . -102.38(15) no
C14 C15 C16 C17 . . . . 0.9(3) no
C7 C15 C16 C17 . . . . -177.30(16) no
C15 C16 C17 C18 . . . . 2.5(3) no
C16 C17 C18 C19 . . . . -3.0(3) no
C15 C14 C19 C18 . . . . 3.3(3) no
C13 C14 C19 C18 . . . . -166.21(18) no
C17 C18 C19 C14 . . . . 0.1(3) no
C8 C7 C20 C25 . . . . -163.87(15) no
C15 C7 C20 C25 . . . . -54.14(19) no
C6 C7 C20 C25 . . . . 87.12(18) no
C8 C7 C20 C21 . . . . 18.9(2) no
C15 C7 C20 C21 . . . . 128.58(16) no
C6 C7 C20 C21 . . . . -90.16(17) no
C25 C20 C21 C22 . . . . 0.2(3) no
C7 C20 C21 C22 . . . . 177.54(16) no
C20 C21 C22 C23 . . . . -0.2(3) no
C23 N1 C23 C22 4 . . . 177.83(13) no
C23 N1 C23 C24 4 . . . -2.4(3) no
C21 C22 C23 N1 . . . . 179.7(2) no
C21 C22 C23 C24 . . . . 0.0(3) no
N1 C23 C24 C25 . . . . -179.59(17) no
C22 C23 C24 C25 . . . . 0.2(3) no
N1 C23 C24 C24 . . . 4 1.46(17) no
C22 C23 C24 C24 . . . 4 -178.75(14) no
C21 C20 C25 C24 . . . . 0.0(2) no
C7 C20 C25 C24 . . . . -177.35(14) no
C23 C24 C25 C20 . . . . -0.2(2) no
C24 C24 C25 C20 4 . . . 178.43(10) no
O02 O02 C02 O01 4 . . . 108.3(17) no
C03 O02 C02 O01 . . . . 8.(3) no
C03 O02 C02 O02 . . . 4 -100.2(17) no
O02 O02 C02 C01 4 . . . -91.4(11) no
C03 O02 C02 C01 . . . . 168.4(18) no
O02 O02 C03 C04 4 . . . 35.0(18) no
C02 O02 C03 C04 . . . . 104.(2) no
O02 C03 C04 C03 . . . 4 -58.(3) no
O01' C02' O02' C03' . . . . -25.(4) no
O02' C02' O02' C03' 4 . . . 80.(4) no
C01' C02' O02' C03' . . . . -170.(3) no
O01' C02' O02' O02' . . . 4 -105.(2) no
C01' C02' O02' O02' . . . 4 110.(3) no
C02' O02' C03' C04' . . . . -59.(5) no
O02' O02' C03' C04' 4 . . . 1.(3) no
C02' O02' C03' C03' . . . 4 -59.(3) no
O02' O02' C03' C03' 4 . . 4 0.00(1) no
O02' C03' C04' C03' . . . 4 -1.(4) no
