#------------------------------------------------------------------------------
#$Date: 2010-01-30 14:59:17 +0100 (Sat, 30 Jan 2010) $
#$Revision: 966 $
#$URL: svn://www.crystallography.net/cod/cif/2/2100877.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2100877
loop_
_publ_author_name
'Ebitani, M.'
'In, Y.'
'Ishida, T.'
'Sakaguchi, K.-i.'
'Flippen-Anderson, J. L.'
'Karle, I. L.'
_publ_section_title
;
 Structures of riboflavin tetraacetate and tetrabutyrate: molecular
 packing mode of riboflavin tetracarboxylate and its extensive stacking
 and hydrogen-bonding characteristics
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              136
_journal_page_last               144
_journal_volume                  49
_journal_year                    1993
_chemical_formula_moiety         '2(C25 H28 N4 O10),C3 H6 O1,H2 O1'
_chemical_formula_sum            'C53 H64 N8 O22'
_chemical_formula_weight         1165.12
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_cell_formula_units_Z            4
_cell_length_a                   61.896(8)
_cell_length_b                   11.4240(10)
_cell_length_c                   8.1340(10)
_cell_volume                     5751.5(12)
_diffrn_radiation_type           Cu
_diffrn_radiation_wavelength     1.5418
_exptl_absorpt_coefficient_mu    0.784
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_meas      1.320(3)
_exptl_crystal_F_000             2456
_[local]_cod_data_source_file    as0605.cif
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
N(1) .89573(4) -.1443(3) .5145(4)
C(2) .88541(6) -.2524(3) .5063(5)
O(2) .89360(4) -.3356(2) .4381(4)
N(3) .86534(5) -.2656(3) .5795(5)
C(4) .85361(5) -.1822(3) .6577(6)
O(4) .83582(4) -.1980(3) .7108(5)
C(4a) .86540(5) -.0672(3) .6719(5)
N(5) .85595(4) .0166(3) .7511(4)
C(5a) .86677(5) .1214(3) .7592(5)
C(6) .85663(6) .2145(4) .8393(6)
C(7) .86629(6) .3253(4) .8554(5)
C(7m) .85411(6) .4248(4) .9400(6)
C(8) .88740(6) .3385(4) .7872(6)
C(8m) .89836(7) .4544(4) .8026(7)
C(9) .89761(5) .2472(3) .7073(5)
C(9a) .88727(5) .1382(3) .6913(5)
N(10) .89652(4) .0457(3) .6024(4)
C(10a) .88627(5) -.0596(3) .5961(5)
C(11) .91677(5) .0621(3) .5137(5)
C(12) .93741(5) .0432(3) .6152(5)
O(12) .94248(3) -.0808(2) .6145(3)
C(12a) .93368(5) -.1453(3) .7364(6)
O(12a) .92331(4) -.1052(3) .8429(4)
C(12b) .93843(7) -.2735(4) .7097(8)
C(13) .95641(5) .1029(3) .5301(5)
O(13) .95206(3) .2267(2) .5609(3)
C(13a) .96032(6) .3042(4) .4488(6)
O(13a) .97172(6) .2735(3) .3381(4)
C(13b) .95435(8) .4295(4) .4908(8)
C(14) .97910(4) .0734(4) .5921(5)
O(14) .97857(3) .0806(2) .7715(3)
C(14a) .99446(6) .1433(4) .8474(5)
O(14a) 1.00908(4) .1835(4) .7709(5)
C(14b) .99095(7) .1481(4) 1.0266(6)
C(15) .98685(5) -.0468(4) .5415(7)
O(15) 1.00991(3) -.0600(3) .5749(4)
C(15a) 1.02340(6) -.0187(4) .4613(6)
O(15a) 1.01770(5) .0343(3) .3432(5)
C(15b) 1.04630(6) -.0470(5) .5057(7)
N(1)B .84670(4) .3186(3) .4367(5)
C(2)B .85791(5) .4218(4) .4489(5)
O(2)B .85071(5) .5053(2) .5244(5)
N(3)B .87790(4) .4328(3) .3756(5)
C(4)B .88831(6) .3458(3) .2948(5)
O(4)B .90671(4) .3585(3) .2353(5)
C(4a)B .87642(6) .2340(4) .2835(5)
N(5)B .88536(4) .1460(3) .2078(4)
C(5a)B .87408(5) .0425(3) .2015(5)
C(6)B .88296(6) -.0511(4) .1186(5)
C(7)B .87260(5) -.1574(3) .1105(5)
C(7m)B .88319(7) -.2602(4) .0207(7)
C(8)B .85250(5) -.1730(3) .1893(5)
C(8m)B .84047(6) -.2864(4) .1799(7)
C(9)B .84354(5) -.0799(4) .2699(5)
C(9a)B .85369(5) .0286(3) .2793(5)
N(10)B .84511(4) .1250(3) .3621(4)
C(10a)B .85580(5) .2309(3) .3627(5)
C(11)B .82466(5) .1166(3) .4569(5)
C(12)B .80527(5) .1503(4) .3559(5)
O(12)B .80263(4) .0656(3) .2283(4)
C(12a)B .80251(9) .0952(5) .0701(7)
O(12a)B .80630(10) .1892(6) .0320(7)
C(12b)B .80081(9) -.0034(6) -.0425(8)
C(13)B .78483(5) .1555(4) .4579(6)
O(13)B .78303(4) .0418(2) .5351(4)
C(13a)B .76711(6) -.0295(4) .4903(7)
O(13a)B .75320(6) -.0022(4) .3900(6)
C(13b)B .76832(9) -.1430(5) .5723(8)
C(14)B .78446(6) .2445(4) .5946(6)
O(14)B .78917(5) .3545(3) .5122(5)
C(14a)B .79841(7) .4374(5) .6066(8)
O(14a)B .80378(7) .4243(4) .7440(5)
C(14b)B .80020(9) .5510(4) .5149(9)
C(15)B .76357(7) .2535(5) .6851(8)
O(15)B .74720(5) .2897(4) .5534(6)
C(15a)B .72770(10) .3090(10) .5780(10)
O(15a)B .71986(9) .2620(7) .7059(9)
C(15b)B .71440(10) .3525(9) .4490(10)
C(1Ac) .97248(8) .8330(6) 1.0653(7)
C(2Ac) .95249(7) .8571(4) 1.1659(6)
C(3Ac) .94060(10) .7563(6) 1.2315(9)
O(1Ac) .94612(6) .9554(3) 1.1887(5)
O(1W) .93110(6) 1.1706(4) 1.0123(6)
H(3) .8595(7) -.353(5) .558(7)
H(6) .8405(8) .200(5) .886(8)
H(9) .9129(7) .259(4) .656(7)
H(7m)a .8373(7) .415(5) .923(8)
H(7m)b .8588(8) .507(5) .887(8)
H(7m)c .8578(8) .426(5) 1.068(8)
H(8m)a .8861(9) .522(5) .802(8)
H(8m)b .9086(8) .466(5) .700(7)
H(8m)c .9074(8) .457(5) .912(8)
H(11)a .9164(8) .157(5) .504(7)
H(11)b .9165(8) -.013(5) .438(7)
H(12) .9347(7) .076(5) .738(8)
H(12b)a .9398(8) -.291(5) .583(8)
H(12b)b .9257(8) -.323(5) .762(8)
H(12b)c .9534(7) -.296(5) .769(7)
H(13) .9567(8) .074(5) .405(7)
H(13b)a .9390(7) .432(5) .558(8)
H(13b)b .9533(8) .482(5) .378(7)
H(13b)c .9666(8) .469(5) .568(8)
H(14) .9904(7) .134(4) .539(7)
H(14b)a .9743(8) .142(5) 1.051(7)
H(14b)b .9977(8) .228(5) 1.074(8)
H(14b)c .9996(8) .076(5) 1.084(8)
H(15)a .9863(8) -.040(5) .410(8)
H(15)b .9802(8) -.104(5) .639(7)
H(15b)a 1.0480(7) -.049(5) .635(7)
H(15b)b 1.0568(8) .021(5) .457(8)
H(15b)c 1.0510(8) -.127(5) .455(8)
H(3)B .8832(8) .517(5) .398(7)
H(6)B .8985(7) -.035(5) .058(7)
H(9)B .8280(8) -.090(5) .328(7)
H(7m)aB .8933(7) -.228(5) -.072(7)
H(7m)bB .8707(7) -.316(5) -.032(7)
H(7m)cB .8926(7) -.310(5) .110(7)
H(8m)aB .8435(8) -.328(4) .062(8)
H(8m)bB .8237(8) -.272(5) .188(7)
H(8m)cB .8458(8) -.342(5) .281(8)
H(11)aB .8257(8) .190(5) .534(7)
H(11)bB .8225(7) .024(5) .468(7)
H(12)B .8074(8) .236(4) .303(7)
H(12b)aB .8085(8) -.077(5) .014(7)
H(12b)bB .8083(8) .018(5) -.155(7)
H(12b)cB .7838(8) -.020(5) -.065(8)
H(13)B .7722(7) .180(5) .375(7)
H(13b)aB .7852(8) -.162(5) .597(8)
H(13b)bB .7612(8) -.209(5) .497(7)
H(13b)cB .7594(8) -.139(5) .688(8)
H(14)B .7953(7) .219(5) .687(7)
H(14b)aB .8017(8) .533(5) .383(7)
H(14b)bB .8144(8) .598(5) .561(8)
H(14b)cB .7858(8) .600(5) .535(8)
H(15)aB .7658(7) .333(5) .754(7)
H(15)bB .7594(8) .165(5) .705(8)
H(15b)aB .7244(8) .403(5) .365(8)
H(15b)bB .7018(8) .406(5) .499(7)
H(15b)CB .7075(8) .279(5) .387(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N(1) C(2) 1.392(5)
N(1) C(10a) 1.311(5)
C(2) O(2) 1.212(5)
C(2) N(3) 1.386(5)
N(3) C(4) 1.357(5)
C(4) O(4) 1.196(5)
C(4) C(4a) 1.507(5)
C(4a) N(5) 1.294(5)
C(4a) C(10a) 1.434(5)
N(5) C(5a) 1.374(5)
C(5a) C(6) 1.399(6)
C(5a) C(9a) 1.397(5)
C(6) C(7) 1.409(6)
C(7) C(7m) 1.528(6)
C(7) C(8) 1.427(6)
C(8) C(8m) 1.493(6)
C(8) C(9) 1.382(6)
C(9) C(9a) 1.405(5)
C(9a) N(10) 1.402(5)
N(10) C(10a) 1.361(4)
N(10) C(11) 1.459(5)
C(11) C(12) 1.536(5)
C(12) O(12) 1.451(4)
C(12) C(13) 1.526(5)
O(12) C(12a) 1.350(5)
C(12a) O(12a) 1.171(5)
C(12a) C(12b) 1.509(6)
C(13) O(13) 1.461(4)
C(13) C(14) 1.530(5)
O(13) C(13a) 1.370(5)
C(13a) O(13a) 1.196(6)
C(13a) C(13b) 1.518(7)
C(14) O(14) 1.462(4)
C(14) C(15) 1.512(6)
O(14) C(14a) 1.364(5)
C(14a) O(14a) 1.191(5)
C(14a) C(14b) 1.475(6)
C(15) O(15) 1.461(5)
O(15) C(15a) 1.332(5)
C(15a) O(15a) 1.189(5)
C(15a) C(15b) 1.498(6)
N(1)B C(2)B 1.372(5)
N(1)B C(10a)B 1.297(5)
C(2)B O(2)B 1.219(5)
C(2)B N(3)B 1.379(5)
N(3)B C(4)B 1.355(5)
C(4)B O(4)B 1.246(5)
C(4)B C(4a)B 1.476(6)
C(4a)B N(5)B 1.302(5)
C(4a)B C(10a)B 1.430(5)
N(5)B C(5a)B 1.375(5)
C(5a)B C(6)B 1.379(5)
C(5a)B C(9a)B 1.421(5)
C(6)B C(7)B 1.374(5)
C(7)B C(7m)B 1.530(6)
C(7)B C(8)B 1.411(5)
C(8)B C(8m)B 1.496(6)
C(8)B C(9)B 1.367(5)
C(9)B C(9a)B 1.392(5)
C(9a)B N(10)B 1.396(5)
N(10)B C(10a)B 1.379(5)
N(10)B C(11)B 1.485(5)
C(11)B C(12)B 1.504(5)
C(12)B O(12)B 1.428(5)
C(12)B C(13)B 1.514(6)
O(12)B C(12a)B 1.331(6)
C(12a)B O(12a)B 1.142(9)
C(12a)B C(12b)B 1.455(9)
C(13)B O(13)B 1.447(5)
C(13)B C(14)B 1.507(6)
O(13)B C(13a)B 1.329(5)
C(13a)B O(13a)B 1.227(7)
C(13a)B C(13b)B 1.459(8)
C(14)B O(14)B 1.454(5)
C(14)B C(15)B 1.491(7)
O(14)B C(14a)B 1.347(6)
C(14a)B O(14a)B 1.176(7)
C(14a)B C(14b)B 1.501(8)
C(15)B O(15)B 1.532(7)
O(15)B C(15a)B 1.240(10)
C(15a)B O(15a)B 1.260(10)
C(15a)B C(15b)B 1.430(10)
C(1Ac) C(2Ac) 1.509(7)
C(2Ac) C(3Ac) 1.466(8)
C(2Ac) O(1Ac) 1.205(6)
_cod_database_code 2100877