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#                                CCDC 
# 
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#
#  This CIF contains data generated directly from one or more entries in
#  the Cambridge Structural Database and will include bibliographic, 
#  chemical, crystal, experimental, refinement, and atomic coordinate data,
#  as available.
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#  Copyright  2014  The Cambridge Crystallographic Data Centre
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#  research purposes only.  It may contain copyright material of the CCDC
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data_CSD_CIF_GIXVAL
_audit_creation_date 2008-06-26
_audit_creation_method CSD-ConQuest-V1
_database_code_CSD GIXVAL
_database_code_depnum_ccdc_archive 'CCDC 665054'
_chemical_formula_sum 'C72 H82 Cl2 F4 N8 O13'
_symmetry_cell_setting orthorhombic
_symmetry_space_group_name_H-M 'F d d 2'
_symmetry_Int_Tables_number 43
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/4-x,1/4+y,1/4+z
3 1/4+x,1/4-y,1/4+z
4 1/2-x,-y,1/2+z
5 x,1/2+y,1/2+z
6 1/4-x,3/4+y,3/4+z
7 1/4+x,3/4-y,3/4+z
8 1/2-x,1/2-y,z
9 1/2+x,y,1/2+z
10 3/4-x,1/4+y,3/4+z
11 3/4+x,1/4-y,3/4+z
12 -x,-y,z
13 1/2+x,1/2+y,z
14 3/4-x,3/4+y,1/4+z
15 3/4+x,3/4-y,1/4+z
16 -x,1/2-y,1/2+z
_cell_length_a 45.7987(6)
_cell_length_b 40.4084(5)
_cell_length_c 40.8397(8)
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 90
_cell_formula_units_Z 32
loop_
_atom_type_symbol
_atom_type_radius_bond
C 0.68
H 0.23
Cl 0.99
F 0.64
N 0.68
O 0.68
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
F1 F -0.64907(10) -0.33836(10) 0.95399(13)
F2 F -0.74163(10) -0.33886(10) 0.91432(13)
F3 F -0.64642(12) -0.33832(11) 0.87138(14)
F4 F -0.6209(1) -0.22875(10) 0.89170(13)
F5 F -0.7392(1) -0.32278(10) 0.99900(14)
N1 N -0.57675(14) -0.26742(18) 0.91229(18)
H1 H -0.59450 -0.27340 0.91590
F6 F -0.70374(10) -0.17511(12) 0.85243(14)
N2 N -0.72562(14) -0.40149(13) 0.90388(17)
H2 H -0.71490 -0.38430 0.90080
N3 N -0.72504(15) -0.38580(14) 0.98963(17)
N4 N -0.59450(16) -0.32861(15) 0.93050(19)
O1 O -0.69823(13) -0.04755(15) 0.74490(16)
N5 N -0.67195(16) -0.39798(14) 0.96741(16)
H3 H -0.68050 -0.37930 0.97080
N6 N -0.67196(16) -0.39894(16) 0.88162(17)
N7 N -0.79612(17) -0.31878(16) 0.9324(2)
C1 C -0.8119(2) -0.3767(2) 0.9337(2)
C2 C -0.75235(16) -0.37941(19) 1.00000(19)
C3 C -0.6914(2) -0.0787(3) 0.7516(2)
C4 C -0.7534(2) -0.39519(19) 0.9142(2)
C5 C -0.63337(17) -0.3639(2) 0.9495(2)
C6 C -0.64227(17) -0.3959(2) 0.9561(2)
C7 C -0.7736(2) -0.4034(2) 1.0064(2)
N8 N -0.66263(15) -0.12989(15) 0.85687(18)
H4 H -0.66080 -0.15060 0.86110
O2 O -0.72491(15) -0.45770(16) 0.90109(19)
C8 C -0.69033(19) -0.1204(2) 0.8463(2)
N9 N -0.61595(13) -0.16280(15) 0.87828(17)
C9 C -0.67767(19) -0.0209(2) 0.7499(3)
H5 H -0.66130 -0.02310 0.73500
H6 H -0.67020 -0.02140 0.77220
C10 C -0.7618(2) -0.3620(2) 0.9194(2)
O3 O -0.85882(15) -0.39189(18) 0.9514(2)
C11 C -0.5857(2) -0.3880(2) 0.9325(2)
C12 C -0.75930(17) -0.34558(17) 1.0049(2)
N10 N -0.7610(2) -0.1635(2) 0.8354(2)
N11 N -0.79127(15) -0.30231(17) 1.0191(2)
C13 C -0.5676(2) -0.3262(2) 0.9207(2)
F7 F -0.62969(14) -0.22559(13) 0.80761(16)
C14 C -0.7116(2) -0.14490(19) 0.8448(2)
C15 C -0.79006(18) -0.3521(2) 0.9293(2)
N12 N -0.6249(2) -0.16244(18) 0.7901(2)
H7 H -0.64040 -0.17420 0.78760
C16 C -0.71887(18) -0.4174(2) 0.9849(2)
C17 C -0.56396(18) -0.16575(18) 0.8928(2)
C18 C -0.8387(2) -0.3661(3) 0.9457(3)
C19 C -0.7384(2) -0.44389(19) 0.9895(3)
H8 H -0.73260 -0.46560 0.98550
C20 C -0.59464(17) -0.2142(2) 0.8955(2)
C21 C -0.8066(2) -0.3605(2) 1.0221(2)
H9 H -0.82500 -0.35410 1.02940
C22 C -0.6574(2) -0.1186(2) 0.7702(2)
C23 C -0.5555(2) -0.2912(2) 0.9141(2)
N13 N -0.6757(2) -0.1441(2) 0.7699(2)
O4 O -0.54183(14) -0.41045(16) 0.91522(18)
C24 C -0.59293(19) -0.18027(18) 0.8882(2)
C25 C -0.60396(19) -0.35940(17) 0.93692(19)
C26 C -0.7860(2) -0.33626(19) 1.0163(2)
C27 C -0.54748(17) -0.3522(2) 0.9155(2)
H10 H -0.52840 -0.34820 0.90890
C28 C -0.6978(2) -0.0874(2) 0.8381(2)
H11 H -0.68400 -0.07070 0.83950
O5 O -0.53437(13) -0.11947(16) 0.88775(19)
C29 C -0.7028(3) -0.1352(3) 0.7583(3)
C30 C -0.57157(17) -0.2334(2) 0.9048(2)
C31 C -0.7471(2) -0.1054(3) 0.8257(3)
C32 C -0.6636(3) -0.08734(18) 0.7623(2)
H12 H -0.64920 -0.07120 0.76390
C33 C -0.7651(2) -0.43729(17) 0.9995(2)
C34 C -0.6244(2) -0.42367(17) 0.9503(2)
H13 H -0.63160 -0.44480 0.95400
O6 O -0.78663(15) -0.45926(13) 1.00396(19)
O7 O -0.60819(19) -0.11036(18) 0.7826(2)
O8 O -0.62193(14) -0.48187(14) 0.86084(19)
N14 N -0.5941(2) -0.32933(18) 0.8421(2)
H14 H -0.60700 -0.31390 0.84240
C35 C -0.6819(2) -0.42851(18) 0.8865(2)
C36 C -0.7131(2) -0.4298(3) 0.8980(2)
C37 C -0.6261(2) -0.4254(2) 0.8619(3)
N15 N -0.58554(18) -0.2654(2) 0.82348(19)
O9 O -0.53027(16) -0.28612(16) 0.9101(2)
C38 C -0.8436(2) -0.3325(3) 0.9496(2)
H15 H -0.86110 -0.32490 0.95820
C39 C -0.6040(2) -0.3612(3) 0.8478(3)
C40 C -0.6452(2) -0.3968(2) 0.8688(2)
C41 C -0.7404(2) -0.1394(3) 0.8354(2)
C42 C -0.6387(2) -0.4560(2) 0.8678(2)
O10 O -0.63691(15) -0.08166(17) 0.85802(19)
C43 C -0.56136(19) -0.1315(2) 0.8849(2)
C44 C -0.8226(2) -0.3112(2) 0.9408(2)
C45 C -0.6302(2) -0.36507(19) 0.8628(2)
C46 C -0.5574(2) -0.3832(2) 0.9209(2)
C47 C -0.71167(18) -0.10316(19) 0.7498(2)
O11 O -0.80955(14) -0.25533(14) 1.03707(19)
C48 C -0.7241(2) -0.0809(2) 0.8286(2)
H16 H -0.72860 -0.05910 0.82340
C49 C -0.61234(19) -0.1321(2) 0.8724(2)
C50 C -0.77563(19) -0.4197(2) 0.9192(2)
H17 H -0.77150 -0.44200 0.91590
C51 C -0.6671(2) -0.45825(19) 0.8808(2)
H18 H -0.67560 -0.47860 0.88540
C52 C -0.8027(2) -0.4101(2) 0.9287(2)
H19 H -0.81650 -0.42670 0.93220
C53 C -0.5660(3) -0.3199(3) 0.8361(3)
O12 O -0.67940(13) -0.45246(14) 0.97035(19)
C54 C -0.6391(2) -0.11236(19) 0.8613(2)
C55 C -0.6278(3) -0.1308(2) 0.7828(3)
C56 C -0.5885(3) -0.3903(2) 0.8401(3)
H20 H -0.57030 -0.38870 0.83010
C57 C -0.5971(2) -0.4200(2) 0.9394(3)
H21 H -0.58540 -0.43850 0.93620
C58 C -0.7231(3) -0.1597(4) 0.7582(3)
O13 O -0.7808(2) -0.0677(3) 0.8054(2)
C59 C -0.5449(2) -0.2182(2) 0.9091(2)
H22 H -0.52920 -0.23050 0.91660
C60 C -0.7719(4) -0.0989(4) 0.8153(4)
C61 C -0.6931(2) 0.0104(2) 0.7439(3)
C62 C -0.6029(2) -0.2125(2) 0.8081(2)
C63 C -0.5784(3) -0.2335(2) 0.8182(2)
C64 C -0.80123(17) -0.3934(2) 1.0175(2)
H23 H -0.81570 -0.40900 1.02160
C65 C -0.8155(3) -0.2001(2) 1.0471(3)
H24 H -0.81650 -0.19640 1.02390
H25 H -0.79550 -0.19920 1.05400
H26 H -0.82650 -0.18330 1.05820
O14 O -0.5460(2) -0.33915(18) 0.8375(2)
C66 C -0.8276(2) -0.2324(3) 1.0548(3)
C67 C -0.6882(2) -0.42490(15) 0.9733(2)
C68 C -0.7393(3) -0.0982(3) 0.7385(3)
H27 H -0.74480 -0.07700 0.73190
C69 C -0.6004(3) -0.1798(2) 0.8013(2)
C70 C -0.58477(18) -0.1137(2) 0.8755(2)
H28 H -0.58360 -0.09110 0.87120
O15 O -0.81129(17) -0.2553(2) 0.9313(3)
C71 C -0.54127(18) -0.1863(3) 0.9027(2)
H29 H -0.52270 -0.17730 0.90480
C72 C -0.5624(3) -0.2835(3) 0.8298(3)
C73 C -0.5739(3) -0.1661(3) 0.8020(2)
H30 H -0.57150 -0.14410 0.79580
O16 O 0.25000 -0.25000 0.9978(3)
C74 C -0.5994(2) -0.4199(3) 0.8468(2)
H31 H -0.58830 -0.43830 0.84090
C75 C -0.7498(4) -0.1549(3) 0.7463(3)
C76 C -0.7944(3) -0.1223(4) 0.8138(2)
H32 H -0.81320 -0.11710 0.80670
O17 O 0.25000 -0.25000 0.7750(5)
C77 C -0.78659(14) -0.1543(4) 0.8238(3)
O18 O -0.5018(2) -0.2239(2) 0.8291(3)
C78 C -0.5338(3) -0.2732(3) 0.8315(2)
H33 H -0.51910 -0.28850 0.83580
C79 C -0.5505(3) -0.2190(3) 0.8187(3)
C80 C -0.8137(2) -0.2863(3) 1.0387(3)
C81 C -0.6103(3) -0.5400(3) 0.8567(5)
H34 H -0.59300 -0.53420 0.86970
O19 O -0.83299(16) -0.30314(18) 1.0516(2)
C82 C -0.5264(3) -0.2394(3) 0.8267(3)
C83 C -0.7797(3) -0.4942(3) 0.9940(5)
H35 H -0.76370 -0.50300 1.00680
H36 H -0.77460 -0.49520 0.97090
C84 C -0.5490(3) -0.1848(3) 0.8120(3)
H37 H -0.53120 -0.17400 0.81420
C85 C -0.8856(2) -0.3827(3) 0.9640(3)
H38 H -0.89520 -0.36680 0.94980
H39 H -0.88340 -0.37300 0.98560
C86 C -0.7592(2) -0.1231(3) 0.7365(2)
H40 H -0.77820 -0.11940 0.72900
O20 O -0.85070(18) -0.26611(18) 0.9597(2)
F8 F -0.7174(2) -0.19207(18) 0.7669(2)
C87 C -0.9038(3) -0.4156(6) 0.9660(6)
H41 H -0.90430 -0.42760 0.94510
C88 C -0.8299(3) -0.2745(3) 0.9447(3)
C89 C -0.4816(4) -0.1060(6) 0.8522(6)
H42 H -0.46080 -0.10340 0.85300
H43 H -0.48840 -0.10110 0.83060
H44 H -0.48660 -0.12830 0.85780
C90 C -0.6718(2) 0.0392(2) 0.7443(4)
H45 H -0.65730 0.03600 0.72760
H46 H -0.66240 0.04040 0.76530
H47 H -0.68220 0.05950 0.74020
C91 C -0.6333(3) -0.5154(2) 0.8663(4)
H48 H -0.65080 -0.51880 0.85330
H49 H -0.63840 -0.51820 0.88920
C92 C -0.8099(3) -0.0619(5) 0.7905(3)
H50 H -0.82520 -0.06460 0.80660
H51 H -0.81330 -0.07720 0.77260
C93 C -0.5130(2) -0.4073(3) 0.9015(3)
H52 H -0.50010 -0.39630 0.91680
H53 H -0.51360 -0.39440 0.88140
C94 C -0.4781(4) -0.2443(4) 0.8397(5)
H54 H -0.47460 -0.26260 0.82470
H55 H -0.48110 -0.25280 0.86160
C95 C -0.4515(4) -0.2168(8) 0.8384(6)
H56 H -0.44820 -0.20780 0.81640
C96 C -0.8267(3) -0.2399(3) 1.0913(3)
H57 H -0.83620 -0.26060 1.09550
H58 H -0.83660 -0.22260 1.10310
H59 H -0.80670 -0.24100 1.09840
C97 C -0.5025(3) -0.4403(4) 0.8947(5)
H60 H -0.50030 -0.45240 0.91540
C98 C -0.8594(2) -0.2357(3) 1.0419(3)
H61 H -0.85980 -0.23150 1.01880
H62 H -0.87170 -0.22000 1.05290
H63 H -0.86640 -0.25770 1.04610
C99 C -0.5293(2) -0.0863(2) 0.8776(4)
H64 H -0.53800 -0.07080 0.89290
H65 H -0.53760 -0.08240 0.85610
C100 C -0.4959(3) -0.0822(3) 0.8767(5)
H66 H -0.48740 -0.08470 0.89860
C101 C -0.4899(3) -0.0474(5) 0.8626(8)
H67 H -0.49890 -0.03100 0.87640
H68 H -0.49790 -0.04590 0.84090
H69 H -0.46920 -0.04360 0.86180
C102 C -0.7166(3) 0.0163(4) 0.7688(5)
H70 H -0.72990 -0.00200 0.76880
H71 H -0.72690 0.03630 0.76340
H72 H -0.70790 0.01850 0.79010
C103 C -0.4734(4) -0.4378(5) 0.8781(5)
H73 H -0.46600 -0.45960 0.87380
H74 H -0.46000 -0.42610 0.89200
H75 H -0.47550 -0.42600 0.85780
O21 O 0.2424(3) -0.2757(3) 0.8838(4)
O22 O -0.7998(2) -0.2098(3) 0.8453(3)
O23 O -0.8296(2) -0.1828(3) 0.8107(3)
C104 C -0.8207(3) -0.2359(4) 0.8440(5)
H76 H -0.81420 -0.25400 0.85740
H77 H -0.82270 -0.24330 0.82170
H78 H -0.83920 -0.22810 0.85180
O24? O 0.2426(3) -0.2698(4) 0.8325(4)
O25 O -0.6895(8) 0.0957(4) 0.8213(5)
O26 O -0.6292(11) -0.3934(12) 0.755(1)
C105 C -0.8078(2) -0.1867(6) 0.8269(4)
O27? O 0.2492(3) -0.2684(3) 0.9360(5)
C106 C -0.6646(5) 0.0131(9) 0.8548(4)
C107 C -0.4600(6) -0.1902(9) 0.8636(10)
H79 H -0.47580 -0.17720 0.85520
H80 H -0.44350 -0.17620 0.86770
H81 H -0.46590 -0.20070 0.88360
C108 C -0.9348(4) -0.4027(9) 0.9767(11)
H82 H -0.94420 -0.39230 0.95840
H83 H -0.93260 -0.38700 0.99420
H84 H -0.94640 -0.42100 0.98400
C109 C -0.6212(5) -0.5740(4) 0.8706(11)
H85 H -0.60640 -0.59060 0.86720
H86 H -0.63880 -0.58050 0.85960
H87 H -0.62490 -0.57190 0.89370
Cl1 Cl -0.7220(9) 0.0204(12) 0.8813(16)
O28 O -0.4854(16) -0.1431(12) 0.9648(12)
C110 C -0.8176(3) -0.2205(3) 0.9348(4)
H88 H -0.80320 -0.20780 0.92310
H89 H -0.81710 -0.21460 0.95760
H90 H -0.83660 -0.21590 0.92610
C111 C -0.6011(7) -0.5362(6) 0.8212(5)
H91 H -0.58480 -0.55040 0.81680
H92 H -0.59560 -0.51360 0.81720
H93 H -0.61710 -0.54210 0.80720
O29 O -0.6174(12) 0.144(3) 0.848(3)
C112 C -0.5224(6) -0.4598(6) 0.8721(7)
H94 H -0.51520 -0.48190 0.86980
H95 H -0.52290 -0.44930 0.85100
H96 H -0.54180 -0.46030 0.88110
C113 C -0.4274(5) -0.2420(6) 0.8496(9)
H97 H -0.40850 -0.23180 0.84780
H98 H -0.42800 -0.26130 0.83590
H99 H -0.43080 -0.24820 0.87190
C114 C -0.8416(5) -0.0172(7) 0.7696(8)
H100 H -0.84390 0.00590 0.76460
H101 H -0.85350 -0.02280 0.78810
H102 H -0.84760 -0.03020 0.75100
C115 C -0.7956(6) -0.0002(8) 0.8025(8)
H103 H -0.79660 0.02190 0.79380
H104 H -0.77560 -0.00590 0.80660
H105 H -0.80650 -0.00120 0.82250
C116 C -0.8087(6) -0.0246(7) 0.7776(8)
H106 H -0.79730 -0.02380 0.75730
Cl2 Cl -0.6380(11) 0.012(2) 0.8871(16)
C117 C -0.8875(5) -0.4343(6) 0.9924(8)
H107 H -0.89700 -0.45520 0.99620
H108 H -0.88750 -0.42160 1.01220
H109 H -0.86780 -0.43810 0.98540
C118 C -0.6892(7) -0.0020(5) 0.8728(5)
O30 O -0.6085(17) -0.643(2) 0.9621(14)
O31 O -0.8102(3) -0.2121(4) 0.7376(3)
C119 C -0.8591(3) -0.1970(5) 0.7243(12)
H110 H -0.86540 -0.19280 0.74630
H111 H -0.87560 -0.20310 0.71110
H112 H -0.85030 -0.17740 0.71540
C120 C -0.8440(7) -0.2557(9) 0.7443(8)
H113 H -0.83050 -0.27280 0.73800
H114 H -0.86360 -0.26300 0.74000
H115 H -0.84180 -0.25100 0.76720
C121 C -0.8376(6) -0.2241(9) 0.7243(5)
C122 C -0.8257(5) -0.2380(6) 0.6912(6)
H116 H -0.81400 -0.25730 0.69540
H117 H -0.81390 -0.22140 0.68070
H118 H -0.84170 -0.24380 0.67720
N16 N -0.7707(4) -0.1824(4) 0.7481(3)
O32 O -0.8073(4) -0.1614(5) 0.7165(5)
C123 C -0.7965(5) -0.1816(4) 0.7322(5)
O33 O 0.2042(12) -0.050(3) 0.6791(17)
O34? O 0.2148(6) -0.0814(7) 0.6218(12)
O35 O -0.50000 -0.50000 0.7835(12)
C124 C -0.8081(5) -0.5134(3) 1.0008(7)
H119 H -0.81520 -0.51160 1.02340
C125 C -0.8292(6) -0.5004(7) 0.9751(11)
H120 H -0.83660 -0.47920 0.98190
H121 H -0.84520 -0.51560 0.97260
H122 H -0.81920 -0.49810 0.95460
C126 C -0.8022(5) -0.5496(4) 0.9893(11)
H123 H -0.78970 -0.56050 1.00470
H124 H -0.79300 -0.54930 0.96820
H125 H -0.82040 -0.56140 0.98780
C127 C -0.7013(5) -0.5348(5) 0.9887(6)
H126 H -0.69610 -0.51760 1.00270
C128 C -0.6991(4) -0.5307(5) 0.9552(6)
H127 H -0.69360 -0.50960 0.94860
O36 O 0.2051(16) -0.1078(12) 0.5603(10)
C129 C -0.7039(7) -0.5532(5) 0.9296(5)
C130 C -0.7172(10) -0.5881(7) 0.9770(8)
H128 H -0.72730 -0.60710 0.98270
C131 C -0.7082(9) -0.5838(6) 0.9446(8)
H129 H -0.70490 -0.60270 0.93210
C132 C -0.7056(3) -0.5499(2) 0.8910(2)
H130 H -0.69770 -0.52890 0.88450
H131 H -0.72560 -0.55150 0.88410
H132 H -0.69440 -0.56740 0.88110
O37 O -0.6434(9) -0.6678(8) 0.944(2)
C133 C -0.6309(13) 0.1163(16) 0.8234(14)
C134 C 0.2079(15) -0.0953(9) 0.5915(12)
C135 C -0.7113(8) -0.5643(6) 1.0012(7)
H133 H -0.71380 -0.56820 1.02340
#END
