#------------------------------------------------------------------------------
#$Date: 2015-06-16 13:11:33 +0300 (Tue, 16 Jun 2015) $
#$Revision: 275 $
#$URL: svn://localhost/tcod/cif/20/00/01/20000171.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_20000171
loop_
_publ_author_name
'van de Streek, Jacco'
'Rantanen, Jukka'
'Bond, Andrew D.'
_publ_section_title
;
 Structures of cefradine dihydrate and cefaclor dihydrate from DFT-D
 calculations
;
_journal_coeditor_code           FM3001
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1229
_journal_page_last               1233
_journal_paper_doi               10.1107/S0108270113026863
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C16 H19 N3 O4 S , 2H2 O'
_chemical_formula_moiety         'C16 H19 N3 O4 S, 2(H2 O)'
_chemical_formula_sum            'C16 H23 N3 O6 S'
_chemical_formula_weight         385.44
_chemical_name_common            'cefradine dihydrate'
_chemical_name_systematic        'Cefradine dihydrate'
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_cell_angle_alpha                90
_cell_angle_beta                 102
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.72
_cell_length_b                   7.31
_cell_length_c                   11.87
_cell_measurement_temperature    298
_cell_volume                     909.845
_computing_structure_solution    'energy-minimized DFT-D calculation'
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_F_000             408.0
_[local]_cod_data_source_file    fm3001.cif
_[local]_cod_data_source_block   I
_[local]_cod_cif_authors_sg_H-M  'P 21'
_cod_original_cell_volume        909.8
_tcod_database_code              20000171
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,y+1/2,-z
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_symmetry_multiplicity
S S1 0.65520 0.60896 0.88510 1.00 2
O O1 0.18867 0.34388 0.67668 1.00 2
O O2 0.17755 0.65406 0.66345 1.00 2
O O3 0.40448 0.64013 0.52164 1.00 2
O O4 0.84801 0.57203 0.55660 1.00 2
N N1 0.46268 0.50979 0.70975 1.00 2
N N2 0.69951 0.71373 0.63967 1.00 2
N N3 0.97769 0.86387 0.52822 1.00 2
C C1 0.39567 0.53033 0.88883 1.00 2
C C2 0.53050 0.53250 0.95841 1.00 2
C C3 0.59860 0.47629 0.75639 1.00 2
C C4 0.36613 0.51597 0.77302 1.00 2
C C5 0.23249 0.50477 0.69957 1.00 2
C C6 0.47952 0.57887 0.60643 1.00 2
C C7 0.62509 0.55000 0.63956 1.00 2
C C8 0.80483 0.71325 0.59400 1.00 2
C C9 0.86931 0.89919 0.58731 1.00 2
C C10 0.91259 0.99824 0.69963 1.00 2
C C11 0.88553 1.17661 0.70515 1.00 2
C C12 0.93129 1.29267 0.80901 1.00 2
C C13 1.02030 1.19352 0.90319 1.00 2
C C14 1.04580 1.01520 0.89885 1.00 2
C C15 0.98926 0.89413 0.79952 1.00 2
C C16 0.29440 0.54678 0.95838 1.00 2
H H2 0.66201 0.83531 0.66714 1.00 2
H H2A 0.53807 0.62555 1.03245 1.00 2
H H2B 0.55576 0.39666 0.99686 1.00 2
H H3 0.61798 0.32934 0.77090 1.00 2
H H3A 0.93434 0.82988 0.44142 1.00 2
H H3B 1.04004 0.76222 0.57051 1.00 2
H H3C 1.03226 0.98026 0.52147 1.00 2
H H7 0.66025 0.44347 0.58885 1.00 2
H H9 0.80130 0.98674 0.52894 1.00 2
H H11 0.82885 1.24441 0.62947 1.00 2
H H12A 0.97815 1.41572 0.78274 1.00 2
H H12B 0.84899 1.34785 0.84138 1.00 2
H H13 1.06653 1.27411 0.97762 1.00 2
H H14 1.11335 0.95240 0.96975 1.00 2
H H15A 1.06574 0.81548 0.77205 1.00 2
H H15B 0.92833 0.78783 0.82746 1.00 2
H H16A 0.28552 0.69062 0.98423 1.00 2
H H16B 0.31906 0.46642 1.03836 1.00 2
H H16C 0.20071 0.50157 0.91026 1.00 2
O O5 0.57022 0.02320 0.69579 1.00 2
H H5A 0.48075 0.00878 0.70770 1.00 2
H H5B 0.56336 0.08220 0.61975 1.00 2
O O6 0.32842 -0.00029 0.73674 1.00 2
H H6A 0.27575 0.11082 0.71600 1.00 2
H H6B 0.27579 -0.10778 0.70734 1.00 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C2 S1 C3 95.06 no
C3 N1 C4 126.13 no
C3 N1 C6 95.38 no
C4 N1 C6 135.78 no
C7 N2 C8 120.49 no
C7 N2 H2 117.03 no
C8 N2 H2 122.05 no
C9 N3 H3A 105.51 no
C9 N3 H3B 112.02 no
C9 N3 H3C 113.35 no
H3A N3 H3B 113.65 no
H3A N3 H3C 104.70 no
H3B N3 H3C 107.50 no
C2 C1 C4 123.64 no
C2 C1 C16 114.76 no
C4 C1 C16 121.60 no
C1 C2 S1 117.06 no
C1 C2 H2A 110.29 no
C1 C2 H2B 110.00 no
S1 C2 H2A 104.56 no
S1 C2 H2B 109.36 no
H2A C2 H2B 104.77 no
N1 C3 S1 111.24 no
N1 C3 C7 87.55 no
N1 C3 H3 111.23 no
S1 C3 C7 118.25 no
S1 C3 H3 111.88 no
C7 C3 H3 114.25 no
C1 C4 N1 120.40 no
C1 C4 C5 125.70 no
N1 C4 C5 113.90 no
C4 C5 O2 117.61 no
C4 C5 O1 115.76 no
O2 C5 O1 126.57 no
N1 C6 O3 132.65 no
N1 C6 C7 92.06 no
O3 C6 C7 135.29 no
C6 C7 C3 85.00 no
C6 C7 N2 114.71 no
C6 C7 H7 113.69 no
C3 C7 N2 119.19 no
C3 C7 H7 112.78 no
N2 C7 H7 109.71 no
N2 C8 O4 123.16 no
N2 C8 C9 116.22 no
O4 C8 C9 120.61 no
C8 C9 N3 105.84 no
C8 C9 C10 116.11 no
C8 C9 H9 107.53 no
N3 C9 C10 111.81 no
N3 C9 H9 106.38 no
C10 C9 H9 108.67 no
C9 C10 C11 118.81 no
C9 C10 C15 118.26 no
C11 C10 C15 122.88 no
C10 C11 C12 123.77 no
C10 C11 H11 119.33 no
C12 C11 H11 116.88 no
C11 C12 C13 112.98 no
C11 C12 H12A 108.65 no
C11 C12 H12B 110.14 no
C13 C12 H12A 110.35 no
C13 C12 H12B 110.29 no
H12A C12 H12B 104.04 no
C12 C13 C14 123.20 no
C12 C13 H13 117.05 no
C14 C13 H13 119.74 no
C13 C14 C15 123.69 no
C13 C14 H14 119.31 no
C15 C14 H14 116.98 no
C14 C15 C10 112.80 no
C14 C15 H15A 109.64 no
C14 C15 H15B 110.22 no
C10 C15 H15A 110.40 no
C10 C15 H15B 109.35 no
H15A C15 H15B 104.06 no
C1 C16 H16A 110.08 no
C1 C16 H16B 111.14 no
C1 C16 H16C 112.22 no
H16A C16 H16B 106.70 no
H16A C16 H16C 107.97 no
H16B C16 H16C 108.52 no
H5A O5 H5B 106.40 no
H6A O6 H6B 108.07 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C2 1.8277 no
S1 C3 1.8048 no
O1 C5 1.2746 no
O2 C5 1.2715 no
O3 C6 1.2345 no
O4 C8 1.2500 no
N1 C3 1.4677 no
N1 C4 1.4002 no
N1 C6 1.3725 no
N2 C7 1.4382 no
N2 C8 1.3502 no
N2 H2 1.0547 no
N3 C9 1.4991 no
N3 H3A 1.0678 no
N3 H3B 1.0542 no
N3 H3C 1.0450 no
C1 C2 1.5083 no
C1 C4 1.3491 no
C1 C16 1.4991 no
C2 H2A 1.1009 no
C2 H2B 1.1028 no
C3 C7 1.5678 no
C3 H3 1.1008 no
C4 C5 1.5165 no
C6 C7 1.5425 no
C7 H7 1.0978 no
C8 C9 1.5344 no
C9 C10 1.5033 no
C9 H9 1.1005 no
C10 C11 1.3403 no
C10 C15 1.5018 no
C11 C12 1.4929 no
C11 H11 1.0931 no
C12 C13 1.4973 no
C12 H12A 1.1063 no
C12 H12B 1.1089 no
C13 C14 1.3351 no
C13 H13 1.0914 no
C14 C15 1.4979 no
C14 H14 1.0909 no
C15 H15A 1.1046 no
C15 H15B 1.1093 no
C16 H16A 1.1050 no
C16 H16B 1.1009 no
C16 H16C 1.0980 no
O5 H5A 1.0037 no
O5 H5B 0.9892 no
O6 H6A 0.9906 no
O6 H6B 0.9877 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O5 H5A O6 . 1.00 1.74 2.740 175.0
O5 H5B O3 2_646 0.99 1.83 2.785 160.8
O6 H6A O1 . 0.99 1.95 2.939 174.0
O6 H6B O2 1_545 0.99 2.05 3.028 173.3
N2 H2 O5 1_565 1.05 1.76 2.805 168.5
N3 H3A O1 2_656 1.07 1.72 2.704 151.7
N3 H3B O2 1_655 1.05 1.83 2.844 160.8
N3 H3C O4 2_756 1.05 1.86 2.757 142.0