#------------------------------------------------------------------------------
#$Date: 2022-10-03 17:40:12 +0300 (Mon, 03 Oct 2022) $
#$Revision: 278324 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/19/2001963.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_2001963
loop_
_publ_author_name
'Shin, W.'
'Cho, S. W.'
'Chae, C. H.'
_publ_section_title
;
 Structure of benfotiamine hemihydrate
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              294
_journal_page_last               298
_journal_paper_doi               10.1107/S0108270192006905
_journal_volume                  49
_journal_year                    1993
_chemical_formula_moiety         'C19 H23 N4 O6 P1 S1,0.5(H2 O1)'
_chemical_formula_sum            'C19 H24 N4 O6.5 P S'
_chemical_formula_weight         475.5
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_cell_angle_alpha                90
_cell_angle_beta                 105.52(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.822(5)
_cell_length_b                   18.556(6)
_cell_length_c                   14.429(5)
_cell_volume                     4340(3)
_diffrn_radiation_type           Cu
_diffrn_radiation_wavelength     1.5418
_exptl_absorpt_coefficient_mu    2.41
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_F_000             1992
_cod_data_source_file            hh1007.cif
_cod_data_source_block           hh1007_structure_1_of_1
_cod_depositor_comments
;
 Marking attached hydrogen atoms.

 Antanas Vaitkus,
 2017-11-30
;
_cod_original_cell_volume        4340.0(10)
_cod_original_formula_sum        'C19 H24 N4 O6.5 P1 S1'
_cod_database_code               2001963
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x+1/2,-y+1/2,z+1/2
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_attached_hydrogens
N(1'A) .3629(2) .1473(2) .1877(3) .035 0
C(2'A) .4350(3) .1605(3) .1707(3) .037 0
N(3'A) .4461(2) .1717(2) .0854(3) .036 0
C(4'A) .3771(3) .1703(2) .0078(3) .029 0
C(5'A) .2983(2) .1570(2) .0216(3) .031 0
C(6'A) .2931(3) .1459(2) .1117(3) .035 0
C(2'aA) .5094(3) .1617(4) .2571(4) .048 0
N(4'aA) .3907(2) .1818(2) -.0762(3) .038 0
C(35'A) .2219(3) .1560(3) -.0628(4) .036 0
N(3A) .2022(2) .2287(2) -.1061(3) .032 0
C(2A) .2116(3) .2416(3) -.1946(3) .039 0
O(2aA) .2419(2) .2006(2) -.2412(2) .049 0
C(4A) .1795(3) .2841(3) -.0494(3) .035 0
C(4aA) .1090(3) .2646(3) -.0093(4) .051 0
C(5A) .2212(3) .3461(3) -.0336(3) .036 0
C(5aA) .2001(3) .4073(3) .0256(3) .043 0
C(5bA) .1620(3) .4711(3) -.0342(3) .042 0
O(5cA) .1736(2) .5358(2) .0247(2) .041 0
P(5dA) .10200(10) .56300(10) .06920(10) .032 0
O(5d1A) .1417(2) .6223(2) .1365(2) .040 0
O(5d2A) .0714(2) .5000(2) .1166(2) .046 0
O(5d3A) .0321(2) .5920(2) -.0148(2) .045 0
S(1A) .30520(10) .36500(10) -.08230(10) .040 0
C(6A) .3901(3) .3632(3) .0247(4) .044 0
O(6aA) .3807(2) .3415(2) .1001(3) .063 0
C(7A) .4691(3) .3872(3) .0095(4) .045 0
C(8A) .5405(3) .3748(3) .0835(4) .057 0
C(9A) .6158(4) .3972(3) .0721(6) .070 0
C(10A) .6214(4) .4308(3) -.0102(6) .070 0
C(11A) .5508(4) .4435(3) -.0841(5) .060 0
C(12A) .4752(3) .4227(3) -.0732(4) .048 0
N(1'B) .6161(2) .3052(2) -.1917(3) .034 0
C(2'B) .5474(3) .2808(2) -.1746(3) .033 0
N(3'B) .5459(2) .2457(2) -.0962(3) .032 0
C(4'B) .6189(3) .2345(2) -.0284(3) .032 0
C(5'B) .6945(2) .2585(2) -.0427(3) .030 0
C(6'B) .6899(3) .2947(2) -.1255(3) .033 0
C(2'aB) .4680(3) .2924(3) -.2514(4) .049 0
N(4'aB) .6140(3) .2002(2) .0504(3) .041 0
C(35'B) .7759(3) .2436(3) .0289(4) .039 0
N(3B) .8002(2) .1676(2) .0199(3) .035 0
C(2B) .7963(3) .1183(3) .0864(3) .040 0
O(2aB) .7693(2) .1298(2) .1556(2) .051 0
C(4B) .8179(3) .1485(3) -.0696(3) .040 0
C(4aB) .8940(3) .1836(4) -.0840(5) .063 0
C(5B) .7689(3) .1037(3) -.1320(3) .040 0
C(5aB) .7807(4) .0843(3) -.2286(4) .057 0
C(5bB) .8101(3) .0081(3) -.2347(4) .055 0
O(5cB) .8970(2) .0037(2) -.1857(2) .046 0
P(5dB) .92830(10) -.05950(10) -.10960(10) .032 0
O(5d1B) .8877(2) -.1288(2) -.1496(2) .041 0
O(5d2B) 1.0207(2) -.0567(2) -.0896(2) .042 0
O(5d3B) .8984(2) -.0406(2) -.0206(2) .045 0
S(1B) .68420(10) .06030(10) -.10340(10) .047 0
C(6B) .5982(3) .0972(3) -.1944(3) .044 0
O(6aB) .6081(2) .1446(2) -.2467(2) .050 0
C(7B) .5167(3) .0670(3) -.1929(4) .048 0
C(8B) .4475(3) .0930(3) -.2627(4) .053 0
C(9B) .3697(4) .0691(4) -.2650(5) .064 0
C(10B) .3588(4) .0181(4) -.2009(5) .072 0
C(11B) .4260(4) -.0085(4) -.1314(5) .075 0
C(12B) .5051(4) .0153(3) -.1280(4) .064 0
O(w1) .0368(9) .1080(10) .8067(10) .190 2
O(w2) .1132(14) .0138(12) .7794(13) .231 2
H(1'A) .359(3) .138(3) .254(4) ? 0
H(6'A) .237(2) .137(2) .130(3) ? 0
H(2'a1A) .494(4) .152(4) .311(5) ? 0
H(2'a2A) .551(4) .145(4) .239(5) ? 0
H(2'a3A) .530(5) .212(5) .270(6) ? 0
H(4'a1A) .443(3) .190(2) -.089(3) ? 0
H(4'a2A) .351(2) .183(2) -.121(4) ? 0
H(35'1A) .231(3) .128(2) -.113(3) ? 0
H(35'2A) .177(2) .142(2) -.036(3) ? 0
H(2A) .193(3) .289(3) -.220(3) ? 0
H(4a1A) .123(4) .238(4) .047(6) ? 0
H(4a2A) .081(3) .302(3) -.003(4) ? 0
H(4a3A) .077(6) .222(5) -.042(7) ? 0
H(5a1A) .159(2) .392(2) .063(3) ? 0
H(5a2A) .251(4) .420(3) .069(4) ? 0
H(5b1A) .198(3) .482(2) -.080(3) ? 0
H(5b2A) .097(4) .462(3) -.057(4) ? 0
H(5d3A) -.010(9) .557(8) -.058(11) ? 0
H(8A) .538(5) .352(4) .151(4) ? 0
H(9A) .658(4) .389(4) .120(5) ? 0
H(10A) .676(4) .445(4) -.020(4) ? 0
H(11A) .555(4) .469(4) -.147(5) ? 0
H(12A) .430(3) .430(3) -.118(4) ? 0
H(1'B) .616(3) .327(3) -.250(4) ? 0
H(6'B) .735(3) .314(2) -.141(3) ? 0
H(2'a1B) .477(4) .338(4) -.291(5) ? 0
H(2'a2B) .424(4) .286(3) -.222(4) ? 0
H(2'a3B) .466(4) .261(4) -.302(5) ? 0
H(4'a1B) .560(3) .189(2) .065(3) ? 0
H(4'a2B) .656(4) .188(4) .088(5) ? 0
H(35'1B) .767(2) .249(2) .092(3) ? 0
H(35'2B) .817(2) .270(2) .011(3) ? 0
H(2B) .821(3) .068(3) .071(4) ? 0
H(4a1B) .893(5) .229(6) -.084(7) ? 0
H(4a2B) .903(6) .167(6) -.146(8) ? 0
H(4a3B) .942(7) .167(7) -.030(9) ? 0
H(5a1B) .820(3) .120(2) -.243(3) ? 0
H(5a2B) .727(4) .088(3) -.269(4) ? 0
H(5b1B) .809(4) -.008(3) -.297(5) ? 0
H(5b2B) .778(4) -.027(4) -.199(5) ? 0
H(5d3B) .930(5) -.003(5) .029(6) ? 0
H(8B) .457(3) .126(3) -.309(4) ? 0
H(9B) .326(4) .090(4) -.305(5) ? 0
H(10B) .301(4) .004(3) -.197(4) ? 0
H(11B) .418(4) -.045(4) -.087(5) ? 0
H(12B) .556(3) -.0060(10) -.0770(10) ? 0
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C(4A) N(3A) C(35'A) 118.5(4)
C(4A) N(3A) C(2A) 122.1(4)
C(4aA) C(4A) N(3A) 114.1(4)
C(5A) C(4A) N(3A) 120.6(4)
C(5A) C(4A) C(4aA) 125.2(5)
C(5aA) C(5A) C(4A) 123.3(4)
C(5bA) C(5aA) C(5A) 113.2(4)
O(5cA) C(5bA) C(5aA) 110.2(3)
P(5dA) O(5dA) C(5bA) 120.0(3)
O(5d1A) P(5dA) O(5cA) 103.9(2)
O(5d2A) P(5dA) O(5cA) 108.9(2)
O(5d3A) P(5dA) O(5cA) 107.1(2)
O(5d2A) P(5dA) O(5d1A) 114.9(2)
O(5d3A) P(5dA) O(5d1A) 111.5(2)
O(5d3A) P(5dA) O(5d2A) 110.2(2)
S(1A) C(5A) C(4A) 122.7(4)
S(1A) C(5A) C(5aA) 114.0(4)
C(6A) S(1A) C(5A) 100.9(2)
O(6aA) C(6A) S(1A) 120.9(4)
C(7A) C(6A) S(1A) 114.0(4)
C(7A) C(6A) O(6aA) 125.1(5)
C(8A) C(7A) C(6A) 117.5(5)
C(12A) C(7A) C(6A) 123.2(5)
N(3'A) C(2'A) N(1'A) 124.9(4)
C(4'A) N(3'A) C(2'A) 117.3(4)
C(5'A) C(4'A) N(3'A) 120.4(4)
C(5'A) C(6'A) N(1'A) 120.4(4)
C(6'A) N(1'A) C(2'A) 119.0(4)
C(6'A) C(5'A) C(4'A) 118.0(4)
C(2'aA) C(2'A) N(1'A) 116.6(4)
C(2'aA) C(2'A) N(3'A) 118.5(4)
N(4'aA) C(4'A) N(3'A) 115.5(4)
N(4'aA) C(4'A) C(5'A) 124.1(4)
C(35'A) C(5'A) C(4'A) 120.9(4)
C(35'A) C(5'A) C(6'A) 121.0(4)
N(3A) C(35'A) C(5'A) 111.9(4)
C(2A) N(3A) C(35'A) 119.3(4)
O(2aA) C(2A) N(3A) 125.9(5)
C(4B) N(3B) C(35B) 116.0(4)
C(4B) N(3B) C(2B) 122.3(4)
C(4aB) C(4B) N(3B) 113.9(4)
C(5B) C(4B) N(3B) 121.2(4)
C(5B) C(4B) C(4aB) 124.9(5)
C(5aB) C(5B) C(4B) 124.3(5)
C(5bB) C(5aB) C(5B) 113.9(5)
O(5cB) C(5bB) C(5aB) 109.2(4)
P(5dB) O(5dB) C(5bB) 118.8(3)
O(5d1B) P(5dB) O(5cB) 109.5(2)
O(5d2B) P(5dB) O(5cB) 103.9(2)
O(5d3B) P(5dB) O(5cB) 106.6(2)
O(5d2B) P(5dB) O(5d1B) 116.4(2)
O(5d3B) P(5dB) O(5d1B) 107.5(2)
O(5d3B) P(5dB) O(5d2B) 112.6(2)
S(1B) C(5B) C(4B) 120.9(4)
S(1B) C(5B) C(5aB) 114.8(4)
C(6B) S(1B) C(5B) 101.2(2)
O(6aB) C(6B) S(1B) 121.1(4)
C(7B) C(6B) S(1B) 114.1(4)
C(7B) C(6B) O(6aB) 124.7(4)
C(8B) C(7B) C(6B) 116.8(5)
C(12B) C(7B) C(6B) 124.5(5)
N(3'B) C(2'B) N(1'B) 123.4(4)
C(4'B) N(3'B) C(2'B) 118.2(4)
C(5'B) C(4'B) N(3'B) 121.3(4)
C(5'B) C(6'B) N(1'B) 121.0(4)
C(6'B) N(1'B) C(2'B) 119.8(4)
C(6'B) C(5'B) C(4'B) 116.3(4)
C(2'aB) C(2'B) N(1'B) 117.4(4)
C(2'aB) C(2'B) N(3'B) 119.2(4)
N(4'aB) C(4'B) N(3'B) 115.9(4)
N(4'aB) C(4'B) C(5'B) 122.8(4)
C(35'B) C(5'B) C(4'B) 122.1(4)
C(35'B) C(5'B) C(6'B) 121.6(4)
N(3B) C(35'B) C(5'B) 109.6(4)
C(2B) N(3B) C(35'B) 121.2(4)
O(2aB) C(2B) N(3B) 124.5(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N(1'A) C(2'A) 1.323(6)
N(1'A) C(6'A) 1.376(6)
C(2'A) N(3'A) 1.310(6)
C(2'A) C(2'aA) 1.512(7)
N(3'A) C(4'A) 1.381(6)
C(4'A) C(5'A) 1.414(6)
C(4'A) N(4'aA) 1.310(6)
C(5'A) C(6'A) 1.342(6)
C(5'A) C(35'A) 1.516(6)
C(35'A) N(3A) 1.486(7)
N(3A) C(2A) 1.349(6)
N(3A) C(4A) 1.428(6)
C(2A) O(2aA) 1.214(6)
C(4A) C(4aA) 1.496(7)
C(4A) C(5A) 1.335(8)
C(5A) C(5aA) 1.519(7)
C(5A) S(1A) 1.773(5)
C(5aA) C(5bA) 1.504(7)
C(5bA) O(5cA) 1.454(6)
O(5cA) P(5dA) 1.591(4)
P(5dA) O(5d1A) 1.501(4)
P(5dA) O(5d2A) 1.513(4)
P(5dA) O(5d3A) 1.542(3)
S(1A) C(6A) 1.801(5)
C(6A) O(6aA) 1.209(7)
C(6A) C(7A) 1.473(7)
C(7A) C(8A) 1.396(7)
C(7A) C(12A) 1.391(8)
C(8A) C(9A) 1.384(8)
C(9A) C(10A) 1.367(11)
C(10A) C(11A) 1.388(10)
C(11A) C(12A) 1.378(8)
N(1'A) H(1'A) 0.99(5)
C(6'A) H(6'A) 1.06(3)
C(2'aA) H(2'a1A) 0.90(7)
C(2'aA) H(2'a2A) 0.87(7)
C(2'aA) H(2'a3A) 1.00(9)
N(4'aA) H(4'a1A) 0.96(5)
N(4'aA) H(4'a2A) 0.80(4)
C(35'A) H(35'1A) 0.94(4)
C(35'A) H(35'2A) 0.97(3)
C(2A) H(2A) 0.97(5)
C(4aA) H(4a1A) 0.93(8)
C(4aA) H(4a2A) 0.86(5)
C(4aA) H(4a3A) 1.00(9)
C(5aA) H(5a1A) 1.02(3)
C(5aA) H(5a2A) 0.94(6)
C(5bA) H(5b1A) 1.03(5)
C(5bA) H(5b2A) 1.07(6)
O(5d3A) H(5d3A) 1.04(15)
C(8A) H(8A) 1.07(6)
C(9A) H(9A) 0.86(7)
C(10A) H(10A) 1.00(7)
C(11A) H(11A) 1.04(7)
C(12A) H(12A) 0.87(5)
N(1'B) C(2'B) 1.324(6)
N(1'B) C(6'B) 1.363(6)
C(2'B) N(3'B) 1.311(6)
C(2'B) C(2'aB) 1.505(7)
N(3'B) C(4'B) 1.366(6)
C(4'B) C(5'B) 1.414(6)
C(4'B) N(4'aB) 1.325(6)
C(5'B) C(6'B) 1.355(6)
C(5'B) C(35'B) 1.504(6)
C(35'B) N(3B) 1.484(7)
N(3B) C(2B) 1.340(6)
N(3B) C(4B) 1.445(6)
C(2B) O(2aB) 1.221(5)
C(4B) C(4aB) 1.500(7)
C(4B) C(5B) 1.336(7)
C(5B) C(5aB) 1.503(7)
C(5B) S(1B) 1.779(5)
C(5aB) C(5bB) 1.508(8)
C(5bB) O(5cB) 1.446(6)
O(5cB) P(5dB) 1.596(4)
P(5dB) O(5d1B) 1.497(4)
P(5dB) O(5d2B) 1.504(4)
P(5dB) O(5d3B) 1.540(3)
S(1B) C(6B) 1.808(5)
C(6B) O(6aB) 1.199(6)
C(6B) C(7B) 1.487(7)
C(7B) C(8B) 1.405(7)
C(7B) C(12B) 1.390(8)
C(8B) C(9B) 1.374(8)
C(9B) C(10B) 1.369(10)
C(10B) C(11B) 1.386(10)
C(11B) C(12B) 1.390(9)
N(1'B) H(1'B) 0.93(5)
C(6'B) H(6'B) 0.92(5)
C(2'aB) H(2'a1B) 1.05(7)
C(2'aB) H(2'a2B) 0.95(6)
C(2'aB) H(2'a3B) 0.93(7)
N(4'aB) H(4'a1B) 1.01(5)
N(4'aB) H(4'a2B) 0.80(7)
C(35'B) H(35'1B) 0.97(4)
C(35'B) H(35'2B) 0.94(3)
C(2B) H(2B) 1.07(5)
C(4aB) H(4a1B) 0.84(11)
C(4aB) H(4a2B) 1.00(11)
C(4aB) H(4a3B) 1.01(12)
C(5aB) H(5a1B) 1.00(4)
C(5aB) H(5a2B) 0.94(6)
C(5bB) H(5b1B) 0.94(7)
C(5bB) H(5b2B) 1.06(7)
O(5d3B) H(5d3B) 1.04(9)
C(8B) H(8B) 0.95(5)
C(9B) H(9B) 0.89(7)
C(10B) H(10B) 1.02(6)
C(11B) H(11B) 0.97(7)
C(12B) H(12B) 1.05(4)
