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#$Date: 2022-09-27 03:27:33 +0300 (Tue, 27 Sep 2022) $
#$Revision: 278201 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/08/2100878.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_2100878
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_paper_doi               10.1107/S0108768192007195
_journal_volume                  49
_journal_year                    1993
_chemical_formula_sum            'C33 H44 N4 O10'
_chemical_formula_weight         656.73
_space_group_IT_number           1
_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                95.510(10)
_cell_angle_beta                 92.170(10)
_cell_angle_gamma                83.590(10)
_cell_formula_units_Z            4
_cell_length_a                   19.409(2)
_cell_length_b                   15.332(2)
_cell_length_c                   11.7840(10)
_cell_volume                     3467.3(7)
_diffrn_radiation_type           Cu
_diffrn_radiation_wavelength     1.5418
_exptl_absorpt_coefficient_mu    0.739
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_density_meas      1.250
_exptl_crystal_F_000             1400
_cod_data_source_file            as0605.cif
_cod_data_source_block           as0605b
_cod_original_cell_volume        3465.1(6)
_cod_database_code               2100878
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
N(1) .9309(5) 1.0384(7) .6230(9)
C(2) .9577(7) .9930(10) .5260(10)
O(2) .9630(6) 1.0314(7) .4392(8)
N(3) .9781(5) .9041(8) .5248(9)
C(4) .9794(7) .8530(10) .6130(10)
O(4) 1.0051(5) .7772(6) .6062(7)
C(4a) .9464(6) .9008(8) .7170(10)
N(5) .9409(5) .8581(6) .8040(10)
C(5a) .9139(6) .9054(8) .9040(10)
C(6) .9059(7) .8575(9) .9960(10)
C(7) .8809(7) .9010(10) 1.0940(10)
C(7m) .8744(8) .8480(10) 1.1950(10)
C(8) .8642(7) .9920(10) 1.1060(10)
C(8m) .8394(8) 1.0430(10) 1.2130(10)
C(9) .8734(6) 1.0384(9) 1.0110(10)
C(9a) .8972(6) .9955(7) .9060(10)
N(10) .9041(5) 1.0398(6) .8123(8)
C(10a) .9284(6) .9954(8) .7120(10)
C(11) .8856(6) 1.1377(7) .8190(9)
C(12) .8105(6) 1.1641(7) .8040(10)
O(12) .7840(4) 1.1365(6) .6920(8)
C(12a) .7625(8) 1.0580(10) .6660(10)
O(12a) .7583(6) 1.0099(6) .7390(10)
C(12b) .7425(9) 1.0440(10) .5400(10)
C(12c) .6740(10) 1.097(2) .516(2)
C(12d) .652(2) 1.081(3) .391(2)
C(13) .7932(7) 1.2664(8) .8250(10)
O(13) .7328(4) 1.2894(5) .8896(7)
C(13a) .7397(8) 1.2825(9) 1.0040(10)
O(13a) .7975(7) 1.2540(7) 1.0439(8)
C(13b) .6736(7) 1.3179(9) 1.0660(10)
C(13c) .6820(10) 1.3070(10) 1.1928(9)
C(13d) .653(2) 1.223(2) 1.219(2)
C(14) .7811(7) 1.3112(8) .7190(10)
O(14) .8431(5) 1.2909(6) .6570(10)
C(14a) .8380(10) 1.2820(10) .544(2)
O(14a) .7804(8) 1.2925(9) .4910(10)
C(14b) .9074(8) 1.2520(10) .4910(10)
C(14c) .9070(10) 1.2750(10) .3680(10)
C(14d) .918(2) 1.371(2) .366(3)
C(15) .7642(7) 1.4111(8) .7350(10)
O(15) .8235(5) 1.4465(6) .7905(9)
C(15a) .8270(8) 1.5350(10) .787(2)
O(15a) .7776(6) 1.5784(6) .7420(10)
C(15b) .8919(8) 1.5670(10) .8450(10)
C(15c) .9318(9) 1.6120(10) .762(2)
C(15d) .9530(10) 1.548(2) .659(2)
N(1)B .5336(7) .6079(9) 1.1100(10)
C(2)B .5080(10) .5740(10) 1.200(2)
O(2)B .4985(7) .6169(8) 1.2940(10)
N(3)B .4917(6) .4877(9) 1.1950(10)
C(4)B .4953(8) .4270(10) 1.098(2)
O(4)B .4794(6) .3548(8) 1.0930(10)
C(4a)B .5241(7) .4650(10) 1.000(2)
N(5)B .5326(6) .4134(8) .9070(10)
C(5a)B .5589(7) .4480(10) .817(2)
C(6)B .5684(8) .3900(10) .713(2)
C(7)B .5891(7) .4230(10) .615(2)
C(7m)B .5987(9) .3640(10) .505(2)
C(8)B .6055(8) .5120(10) .623(2)
C(8m)B .6310(8) .5510(10) .5220(10)
C(9)B .5954(7) .5700(10) .726(2)
C(9a)B .5740(7) .5360(10) .825(2)
N(10)B .5646(6) .5886(7) .9250(10)
C(10a)B .5400(7) .5540(10) 1.017(2)
C(11)B .5794(7) .6831(9) .9320(10)
C(12)B .6546(8) .6905(9) .936(2)
O(12)B .6835(6) .6727(6) 1.0480(10)
C(12a)B .7100(10) .5880(10) 1.064(2)
O(12a)B .7096(6) .5302(7) .9880(10)
C(12b)B .729(2) .587(2) 1.191(2)
C(12c)B .8060(10) .565(4) 1.208(3)
C(12d)B .821(3) .482(6) 1.270(10)
C(13)B .6670(8) .7904(9) .926(2)
O(13)B .7268(5) .7890(6) .8550(10)
C(13a)B .7142(7) .7747(9) .7380(10)
O(13a)B .6598(6) .7544(7) .6970(10)
C(13b)B .7771(6) .7870(9) .6700(10)
C(13c)B .7701(8) .7480(10) .5480(10)
C(13d)B .8304(8) .7660(10) .4790(10)
C(14)B .6844(9) .8422(9) 1.040(2)
O(14)B .6230(5) .8438(6) 1.1090(10)
C(14a)B .6350(10) .8340(10) 1.227(2)
O(14a)B .6901(7) .8370(10) 1.2590(10)
C(14b)B .5664(7) .8240(10) 1.2800(10)
C(14c)B .5770(10) .8050(10) 1.4040(10)
C(14d)B .582(2) .890(2) 1.481(2)
C(15)B .6975(8) .9370(10) 1.018(2)
O(15)B .6405(6) .9738(8) .953(2)
C(15a)B .656(2) 1.061(3) .938(4)
O(15a)B .685(2) 1.0980(10) .984(3)
C(15b)B .584(2) 1.109(2) .919(3)
C(15c)B .552(2) 1.074(3) .805(3)
C(15d)B .486(2) 1.131(3) .778(3)
N(1)C .4070(6) .4419(7) .5790(10)
C(2)C .4271(7) .4823(9) .490(2)
O(2)C .4347(6) .4436(6) .3980(10)
N(3)C .4432(6) .5680(8) .5060(10)
C(4)C .4382(6) .6230(10) .608(2)
O(4)C .4547(5) .6976(7) .6160(10)
C(4a)C .4127(7) .5800(10) .704(2)
N(5)C .4072(6) .6237(7) .7970(10)
C(5a)C .3815(7) .5876(9) .8850(10)
C(6)C .3671(8) .6330(10) .993(2)
C(7)C .3375(9) .6000(10) 1.081(2)
C(7m)C .3246(9) .6580(10) 1.1890(10)
C(8)C .3246(9) .514(2) 1.067(2)
C(8m)C .2920(10) .4690(10) 1.1580(10)
C(9)C .3390(8) .4620(10) .969(2)
C(9a)C .3678(7) .4950(8) .8760(10)
N(10)C .3829(5) .4474(7) .7710(10)
C(10a)C .3995(7) .4875(9) .683(2)
C(11)C .3812(6) .3512(7) .7610(10)
C(12)C .3106(7) .3199(8) .7270(10)
O(12)C .3057(5) .2396(5) .7802(8)
C(12a)C .2659(7) .2434(8) .8730(10)
O(12a)C .2382(7) .3074(8) .9190(10)
C(12b)C .2653(9) .1510(7) .9090(10)
C(12c)C .2326(9) .1544(9) 1.0250(10)
C(12d)C .2450(10) .0650(10) 1.073(2)
C(13)C .3019(7) .3014(8) .6050(10)
O(13)C .2302(5) .2926(6) .5711(8)
C(13a)C .1920(10) .3600(10) .543(2)
O(13a)C .2020(9) .4340(10) .590(2)
C(13b)C .1202(7) .3470(10) .490(2)
C(13c)C .1260(10) .302(2) .370(2)
C(13d)C .172(2) .349(2) .300(2)
C(14)C .3425(7) .2180(9) .5530(10)
O(14)C .3643(6) .2283(6) .4412(9)
C(14a)C .4320(10) .2270(10) .4280(10)
O(14a)C .4756(6) .2163(8) .4990(10)
C(14b)C .4530(10) .2360(10) .307(2)
C(14c)C .4240(10) .167(2) .223(2)
C(14d)C .472(2) .0820(10) .214(3)
C(15)C .3045(8) .1350(8) .549(2)
O(15)C .3530(6) .0596(7) .5160(10)
C(15a)C .3440(10) -.0140(10) .552(2)
O(15a)C .2990(8) -.0157(8) .6180(10)
C(15b)C .3900(10) -.0950(10) .504(2)
C(15c)C .3900(10) -.101(2) .374(2)
C(15d)C .318(2) -.105(3) .323(2)
N(1)D 1.0735(5) .8596(7) 1.1141(9)
C(2)D 1.0523(8) .8970(10) 1.2210(10)
O(2)D 1.0449(5) .8478(7) 1.2965(7)
N(3)D 1.0362(6) .9848(9) 1.2450(10)
C(4)D 1.0403(8) 1.0470(10) 1.1690(10)
O(4)D 1.0232(7) 1.1261(7) 1.1964(9)
C(4a)D 1.0621(6) 1.0125(8) 1.0560(10)
N(5)D 1.0642(6) 1.0657(6) .9790(10)
C(5a)D 1.0841(6) 1.0299(8) .8730(10)
C(6)D 1.0890(7) 1.0887(9) .7900(10)
C(7)D 1.1082(7) 1.0570(10) .6810(10)
C(7m)D 1.1082(8) 1.1270(10) .5880(10)
C(8)D 1.1235(6) .9665(9) .6510(10)
C(8m)D 1.1449(8) .9300(10) .5340(10)
C(9)D 1.1201(6) .9089(8) .7350(10)
C(9a)D 1.0996(6) .9397(8) .8450(10)
N(10)D 1.0925(4) .8841(5) .9306(8)
C(10a)D 1.0770(6) .9183(8) 1.0410(10)
C(11)D 1.0950(6) .7848(7) .8970(10)
C(12)D 1.1675(5) .7390(7) .9240(10)
O(12)D 1.2191(4) .7735(5) .8628(7)
C(12a)D 1.2638(6) .8206(9) .9250(10)
O(12a)D 1.2608(7) .8393(8) 1.0220(10)
C(12b)D 1.3157(6) .8503(9) .8477(9)
C(12c)D 1.3762(7) .8840(10) .9180(10)
C(12d)D 1.4374(9) .889(2) .842(2)
C(13)D 1.1715(6) .6423(7) .8710(10)
O(13)D 1.1542(4) .6408(5) .7546(7)
C(13a)D 1.2054(7) .6178(9) .6808(8)
O(13a)D 1.2598(6) .5870(10) .7089(8)
C(13b)D 1.1770(5) .6310(10) .5609(9)
C(13c)D 1.2358(8) .6254(9) .4780(10)
C(13d)D 1.2757(9) .7060(10) .500(2)
C(14)D 1.1184(7) .5904(8) .9230(10)
O(14)D 1.1247(5) .6031(5) 1.0481(8)
C(14a)D 1.0651(8) .6296(9) 1.1080(10)
O(14a)D 1.0088(6) .6424(7) 1.0570(10)
C(14b)D 1.0867(6) .6390(10) 1.2340(10)
C(14c)D 1.0239(8) .6510(10) 1.3090(10)
C(14d)D .9980(10) .5640(10) 1.324(2)
C(15)D 1.1345(9) .4917(8) .884(2)
O(15)D 1.0786(8) .4496(7) .9250(10)
C(15a)D 1.0620(10) .3750(10) .869(2)
O(15b)D 1.0937(9) .3397(9) .7900(10)
C(15b)D .9980(10) .3350(10) .901(2)
C(15c)D .9790(10) .365(2) 1.023(2)
C(15d)D 1.039(2) .340(3) 1.105(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N(1) C(2) 1.37(2)
N(1) C(10a) 1.30(2)
C(2) O(2) 1.24(2)
C(2) N(3) 1.38(2)
N(3) C(4) 1.36(2)
C(4) O(4) 1.21(2)
C(4) C(4a) 1.50(2)
C(4a) N(5) 1.28(2)
C(4a) C(10a) 1.46(2)
N(5) C(5a) 1.41(2)
C(5a) C(6) 1.39(2)
C(5a) C(9a) 1.38(2)
C(6) C(7) 1.35(2)
C(7) C(7m) 1.53(2)
C(7) C(8) 1.39(2)
C(8) C(8m) 1.49(2)
C(8) C(9) 1.41(2)
C(9) C(9a) 1.41(2)
C(9a) N(10) 1.37(2)
N(10) C(10a) 1.38(2)
N(10) C(11) 1.500(10)
C(11) C(12) 1.48(2)
C(12) O(12) 1.440(10)
C(12) C(13) 1.56(2)
O(12) C(12a) 1.32(2)
C(12a) O(12a) 1.20(2)
C(12a) C(12b) 1.52(2)
C(12b) C(12c) 1.52(3)
C(12c) C(12d) 1.52(4)
C(13) O(13) 1.42(2)
C(13) C(14) 1.48(2)
O(13) C(13a) 1.36(2)
C(13a) O(13a) 1.25(2)
C(13a) C(13b) 1.52(2)
C(13b) C(13c) 1.52(2)
C(13c) C(13d) 1.52(4)
C(14) O(14) 1.42(2)
C(14) C(15) 1.52(2)
O(14) C(14a) 1.32(2)
C(14a) O(14a) 1.26(2)
C(14a) C(14b) 1.52(3)
C(14b) C(14c) 1.52(3)
C(14c) C(14d) 1.52(4)
C(15) O(15) 1.43(2)
O(15) C(15a) 1.37(2)
C(15a) O(15a) 1.24(2)
C(15a) C(15b) 1.52(2)
C(15b) C(15c) 1.52(2)
C(15c) C(15d) 1.52(3)
N(1)B C(2)B 1.36(3)
N(1)B C(10a)B 1.31(2)
C(2)B O(2)B 1.24(3)
C(2)B N(3)B 1.39(3)
N(3)B C(4)B 1.40(2)
C(4)B O(4)B 1.18(2)
C(4)B C(4a)B 1.49(2)
C(4a)B N(5)B 1.29(2)
C(4a)B C(10a)B 1.42(2)
N(5)B C(5a)B 1.37(2)
C(5a)B C(6)B 1.44(2)
C(5a)B C(9a)B 1.41(2)
C(6)B C(7)B 1.39(2)
C(7)B C(7m)B 1.51(2)
C(7)B C(8)B 1.43(2)
C(8)B C(8m)B 1.51(2)
C(8)B C(9)B 1.45(2)
C(9)B C(9a)B 1.42(2)
C(9a)B N(10)B 1.37(2)
N(10)B C(10a)B 1.37(2)
N(10)B C(11)B 1.50(2)
C(11)B C(12)B 1.48(2)
C(12)B O(12)B 1.45(2)
C(12)B C(13)B 1.59(2)
O(12)B C(12a)B 1.36(2)
C(12a)B O(12a)B 1.21(2)
C(12a)B C(12b)B 1.52(3)
C(12b)B C(12c)B 1.52(5)
C(12c)B C(12d)B 1.50(10)
C(13)B O(13)B 1.45(2)
C(13)B C(14)B 1.55(2)
O(13)B C(13a)B 1.40(2)
C(13a)B O(13a)B 1.21(2)
C(13a)B C(13b)B 1.52(2)
C(13b)B C(13c)B 1.52(2)
C(13c)B C(13d)B 1.52(2)
C(14)B O(14)B 1.46(2)
C(14)B C(15)B 1.55(2)
O(14)B C(14a)B 1.42(2)
C(14a)B O(14a)B 1.13(2)
C(14a)B C(14b)B 1.52(2)
C(14b)B C(14c)B 1.52(2)
C(14c)B C(14d)B 1.52(3)
C(15)B O(15)B 1.42(2)
O(15)B C(15a)B 1.42(5)
C(15a)B C(15b)B 1.52(5)
C(15b)B C(15c)B 1.52(5)
C(15c)B C(15d)B 1.52(6)
N(1)C C(2)C 1.36(2)
N(1)C C(10a)C 1.35(2)
C(2)C O(2)C 1.19(2)
C(2)C N(3)C 1.38(2)
N(3)C C(4)C 1.40(2)
C(4)C O(4)C 1.21(2)
C(4)C C(4a)C 1.50(2)
C(4a)C N(5)C 1.23(2)
C(4a)C C(10a)C 1.46(2)
N(5)C C(5a)C 1.36(2)
C(5a)C C(6)C 1.41(2)
C(5a)C C(9a)C 1.47(2)
C(6)C C(7)C 1.37(3)
C(7)C C(7m)C 1.50(3)
C(7)C C(8)C 1.36(3)
C(8)C C(8m)C 1.53(3)
C(8)C C(9)C 1.36(3)
C(9)C C(9a)C 1.41(2)
C(9a)C N(10)C 1.39(2)
N(10)C C(10a)C 133(2)
N(10)C C(11)C 1.47(2)
C(11)C C(12)C 1.53(2)
C(12)C O(12)C 1.45(2)
C(12)C C(13)C 1.44(2)
O(12)C C(12a)C 1.35(2)
C(12a)C O(12a)C 1.16(2)
C(12a)C C(12b)C 1.52(2)
C(12b)C C(12c)C 1.52(2)
C(12c)C C(12d)C 1.52(2)
C(13)C O(13)C 1.45(2)
C(13)C C(14)C 1.51(2)
O(13)C C(13a)C 1.27(2)
C(13a)C O(13a)C 1.25(3)
C(13a)C C(13b)C 1.52(3)
C(13b)C C(13c)C 1.52(3)
C(13c)C C(13d)C 1.52(4)
C(14)C O(14)C 1.43(2)
C(14)C C(15)C 1.54(2)
O(14)C C(14a)C 1.32(2)
C(14a)C O(14a)C 1.18(2)
C(14a)C C(14b)C 1.52(3)
C(14b)C C(14c)C 1.52(3)
C(14c)C C(14d)C 1.52(4)
C(15)C O(15)C 1.44(2)
O(15)C C(15a)C 1.27(2)
C(15a)C O(15a)C 1.20(2)
C(15a)C C(15b)C 1.52(3)
C(15b)C C(15c)C 1.52(4)
C(15c)C C(15d)C 1.52(5)
N(1)D C(2)D 1.39(2)
N(1)D C(10a)D 1.32(2)
C(2)D O(2)D 1.25(2)
C(2)D N(3)D 1.34(2)
N(3)D C(4)D 1.38(2)
C(4)D O(4)D 1.23(2)
C(4)D C(4a)D 1.45(2)
C(4a)D N(5)D 1.28(2)
C(4a)D C(10a)D 1.44(2)
N(5)D C(5a)D 1.36(2)
C(5a)D C(6)D 1.41(2)
C(5a)D C(9a)D 1.39(2)
C(6)D C(7)D 1.37(2)
C(7)D C(7m)D 1.60(2)
C(7)D C(8)D 1.41(2)
C(8)D C(8m)D 1.49(2)
C(8)D C(9)D 1.40(2)
C(9)D C(9a)D 1.39(2)
C(9a)D N(10)D 1.410(10)
N(10)D C(10a)D 1.380(10)
N(10)D C(11)D 1.530(10)
C(11)D C(12)D 1.54(2)
C(12)D O(12)D 1.450(10)
C(12)D C(13)D 1.55(2)
O(12)D C(12a)D 1.33(2)
C(12a)D O(12a)D 1.15(2)
C(12a)D C(12b)D 1.52(2)
C(12b)D C(12c)D 1.52(2)
C(12c)D C(12d)D 1.52(3)
C(13)D O(13)D 1.400(10)
C(13)D C(14)D 1.54(2)
O(13)D C(13a)D 1.340(10)
C(13a)D O(13a)D 1.16(2)
C(13a)D C(13b)D 1.52(2)
C(13b)D C(13c)D 1.52(2)
C(13c)D C(13d)D 1.52(2)
C(14)D O(14)D 1.47(2)
C(14)D C(15)D 1.54(2)
O(14)D C(14a)D 1.38(2)
C(14a)D O(14a)D 1.23(2)
C(14a)D C(14b)D 1.52(2)
C(14b)D C(14c)D 1.52(2)
C(14c)D C(14d)D 1.52(3)
C(15)D O(15)D 1.44(2)
O(15)D C(15a)D 1.32(2)
C(15a)D O(15b)D 1.19(3)
C(15a)D C(15b)D 1.52(3)
C(15b)D C(15c)D 1.52(3)
C(15c)D C(15d)D 1.52(4)
