#------------------------------------------------------------------------------
#$Date: 2016-03-26 19:27:03 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180435 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/04/7210429.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_7210429
loop_
_publ_author_name
'Yan, Yan'
'Chen, Jia-Mei'
'Lu, Tong-Bu'
_publ_section_title
;
 Simultaneously enhancing the solubility and permeability of acyclovir by
 crystal engineering approach
;
_journal_issue                   33
_journal_name_full               CrystEngComm
_journal_page_first              6457
_journal_paper_doi               10.1039/c3ce41017j
_journal_volume                  15
_journal_year                    2013
_chemical_formula_sum            'C14 H21 N5 O11'
_chemical_formula_weight         435.36
_chemical_name_systematic
;
?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.906(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   21.3178(15)
_cell_length_b                   6.4895(5)
_cell_length_c                   29.435(2)
_cell_measurement_reflns_used    2001
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      65.4387
_cell_measurement_theta_min      3.0908
_cell_volume                     3952.7(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug 3 2011,13:03:54)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug 3 2011,13:03:54)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug 3 2011,13:03:54)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_sigmaI/netI    0.0392
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            6647
_diffrn_reflns_theta_full        65.54
_diffrn_reflns_theta_max         65.54
_diffrn_reflns_theta_min         3.09
_exptl_absorpt_coefficient_mu    1.109
_exptl_absorpt_correction_T_max  0.8086
_exptl_absorpt_correction_T_min  0.7110
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       bluk
_exptl_crystal_F_000             1824
_exptl_crystal_size_max          0.033
_exptl_crystal_size_mid          0.021
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.800
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     278
_refine_ls_number_reflns         3312
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.981
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0471
_refine_ls_shift/su_max          0.024
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0747P)²+5.1284P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1230
_refine_ls_wR_factor_ref         0.1408
_reflns_number_gt                2489
_reflns_number_total             3312
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ce41017j.txt
_cod_data_source_block           11110311
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      'C2/c '
_cod_database_code               7210429
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1W O 0.04652(13) 0.8359(4) 0.47378(9) 0.0660(8) Uani 1 1 d .
H1B H 0.0287 0.7915 0.4948 0.099 Uiso 1 1 d R
H1C H 0.0233 0.9289 0.4576 0.099 Uiso 1 1 d R
O2W O 0.05509(9) 0.5100(3) 0.41941(7) 0.0351(5) Uani 1 1 d .
H2C H 0.0945 0.4847 0.4322 0.053 Uiso 1 1 d R
H2D H 0.0426 0.6143 0.4323 0.053 Uiso 1 1 d R
C3 C 0.14983(11) 0.5562(4) 0.24519(8) 0.0185(5) Uani 1 1 d .
C4 C 0.09529(11) 0.5456(4) 0.30108(8) 0.0195(5) Uani 1 1 d .
C5 C 0.20944(11) 0.5297(4) 0.27548(8) 0.0191(5) Uani 1 1 d .
C6 C 0.22718(11) 0.5561(4) 0.20700(8) 0.0202(5) Uani 1 1 d .
H6 H 0.2482 0.5621 0.1820 0.024 Uiso 1 1 calc R
C7 C 0.24003(13) 0.4972(4) 0.46072(9) 0.0250(6) Uani 1 1 d .
C8 C 0.21366(11) 0.5099(4) 0.32377(8) 0.0189(5) Uani 1 1 d .
C9 C 0.25161(13) 0.4999(4) 0.51215(9) 0.0263(6) Uani 1 1 d .
H9 H 0.2150 0.5021 0.5253 0.032 Uiso 1 1 calc R
C10 C 0.30945(13) 0.4995(4) 0.54121(9) 0.0260(6) Uani 1 1 d .
C11 C 0.11452(12) 0.6205(4) 0.15753(8) 0.0240(6) Uani 1 1 d .
H11A H 0.0853 0.7309 0.1632 0.029 Uiso 1 1 calc R
H11B H 0.1374 0.6721 0.1343 0.029 Uiso 1 1 calc R
C12 C 0.31576(13) 0.4953(4) 0.59269(9) 0.0262(6) Uani 1 1 d .
C13 C 0.06761(14) 0.1300(5) 0.09897(10) 0.0350(7) Uani 1 1 d .
H13A H 0.0923 0.0168 0.0889 0.042 Uiso 1 1 calc R
H13B H 0.0477 0.0754 0.1236 0.042 Uiso 1 1 calc R
C14 C 0.11294(13) 0.3005(4) 0.11896(9) 0.0301(6) Uani 1 1 d .
H14A H 0.1498 0.2459 0.1432 0.036 Uiso 1 1 calc R
H14B H 0.1301 0.3658 0.0940 0.036 Uiso 1 1 calc R
N1 N 0.15342(9) 0.5230(3) 0.33373(7) 0.0195(5) Uani 1 1 d .
H1 H 0.1521 0.5163 0.3634 0.023 Uiso 1 1 calc R
N2 N 0.04188(10) 0.5481(3) 0.31701(7) 0.0245(5) Uani 1 1 d .
H2A H 0.0038 0.5613 0.2973 0.029 Uiso 1 1 calc R
H2B H 0.0446 0.5365 0.3472 0.029 Uiso 1 1 calc R
N3 N 0.09118(9) 0.5632(3) 0.25538(7) 0.0192(4) Uani 1 1 d .
N4 N 0.16188(9) 0.5747(3) 0.20139(7) 0.0194(5) Uani 1 1 d .
N5 N 0.25745(9) 0.5289(3) 0.25088(7) 0.0193(5) Uani 1 1 d .
O3 O 0.37657(9) 0.4750(4) 0.61652(6) 0.0365(5) Uani 1 1 d .
H3 H 0.3780 0.4675 0.6452 0.055 Uiso 1 1 calc R
O4 O 0.27050(9) 0.5069(4) 0.61036(7) 0.0424(6) Uani 1 1 d .
O5 O 0.18534(9) 0.4926(3) 0.43547(6) 0.0300(5) Uani 1 1 d .
O6 O 0.29173(9) 0.4984(3) 0.44439(6) 0.0347(5) Uani 1 1 d .
H6A H 0.2810 0.4968 0.4150 0.052 Uiso 1 1 calc R
O7 O 0.26389(8) 0.4808(3) 0.35487(6) 0.0247(4) Uani 1 1 d .
O8 O 0.07779(8) 0.4481(3) 0.13915(6) 0.0253(4) Uani 1 1 d .
O9 O 0.01795(9) 0.1951(3) 0.06020(6) 0.0341(5) Uani 1 1 d .
H9A H -0.0024 0.2938 0.0684 0.051 Uiso 1 1 calc R
C1 C 0.40932(12) 0.5524(4) 0.24853(8) 0.0196(5) Uani 1 1 d .
C2 C 0.48084(12) 0.5562(4) 0.26455(9) 0.0225(5) Uani 1 1 d .
H2 H 0.4998 0.5587 0.2972 0.027 Uiso 1 1 calc R
O1 O 0.38056(8) 0.5402(3) 0.28272(6) 0.0235(4) Uani 1 1 d .
H1A H 0.3403 0.5402 0.2719 0.035 Uiso 1 1 calc R
O2 O 0.38014(8) 0.5597(3) 0.20711(6) 0.0254(4) Uani 1 1 d .
H10 H 0.3481(16) 0.500(5) 0.5300(11) 0.039(9) Uiso 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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_site_symmetry_1
H1B O1W H1C 110.2 .
H2C O2W H2D 109.8 .
N3 C3 C5 128.2(2) .
N3 C3 N4 126.4(2) .
C5 C3 N4 105.4(2) .
N3 C4 N2 120.0(2) .
N3 C4 N1 122.8(2) .
N2 C4 N1 117.1(2) .
C3 C5 N5 110.1(2) .
C3 C5 C8 119.4(2) .
N5 C5 C8 130.5(2) .
N5 C6 N4 112.2(2) .
N5 C6 H6 123.9 .
N4 C6 H6 123.9 .
O5 C7 O6 122.9(2) .
O5 C7 C9 121.6(2) .
O6 C7 C9 115.5(2) .
O7 C8 N1 122.0(2) .
O7 C8 C5 126.2(2) .
N1 C8 C5 111.7(2) .
C10 C9 C7 124.4(2) .
C10 C9 H9 117.8 .
C7 C9 H9 117.8 .
C9 C10 C12 120.1(2) .
C9 C10 H10 121.5(19) .
C12 C10 H10 118.4(19) .
O8 C11 N4 112.5(2) .
O8 C11 H11A 109.1 .
N4 C11 H11A 109.1 .
O8 C11 H11B 109.1 .
N4 C11 H11B 109.1 .
H11A C11 H11B 107.8 .
O4 C12 O3 124.2(2) .
O4 C12 C10 123.6(3) .
O3 C12 C10 112.2(2) .
O9 C13 C14 112.5(2) .
O9 C13 H13A 109.1 .
C14 C13 H13A 109.1 .
O9 C13 H13B 109.1 .
C14 C13 H13B 109.1 .
H13A C13 H13B 107.8 .
O8 C14 C13 107.8(2) .
O8 C14 H14A 110.1 .
C13 C14 H14A 110.1 .
O8 C14 H14B 110.1 .
C13 C14 H14B 110.1 .
H14A C14 H14B 108.5 .
C4 N1 C8 125.5(2) .
C4 N1 H1 117.3 .
C8 N1 H1 117.3 .
C4 N2 H2A 120.0 .
C4 N2 H2B 120.0 .
H2A N2 H2B 120.0 .
C4 N3 C3 112.4(2) .
C6 N4 C3 106.99(19) .
C6 N4 C11 126.19(19) .
C3 N4 C11 126.69(19) .
C6 N5 C5 105.3(2) .
C12 O3 H3 109.5 .
C7 O6 H6A 109.5 .
C11 O8 C14 113.33(19) .
C13 O9 H9A 109.5 .
O2 C1 O1 123.3(2) .
O2 C1 C2 123.4(2) .
O1 C1 C2 113.2(2) .
C2 C2 C1 122.9(3) 2_655
C2 C2 H2 118.5 2_655
C1 C2 H2 118.5 .
C1 O1 H1A 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1W H1B 0.8502 .
O1W H1C 0.8502 .
O2W H2C 0.8499 .
O2W H2D 0.8503 .
C3 N3 1.355(3) .
C3 C5 1.376(3) .
C3 N4 1.379(3) .
C4 N3 1.332(3) .
C4 N2 1.332(3) .
C4 N1 1.382(3) .
C5 N5 1.389(3) .
C5 C8 1.408(3) .
C6 N5 1.310(3) .
C6 N4 1.367(3) .
C6 H6 0.9500 .
C7 O5 1.223(3) .
C7 O6 1.304(3) .
C7 C9 1.474(4) .
C8 O7 1.245(3) .
C8 N1 1.387(3) .
C9 C10 1.321(4) .
C9 H9 0.9500 .
C10 C12 1.489(4) .
C10 H10 0.96(3) .
C11 O8 1.397(3) .
C11 N4 1.465(3) .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C12 O4 1.203(3) .
C12 O3 1.324(3) .
C13 O9 1.421(3) .
C13 C14 1.494(4) .
C13 H13A 0.9900 .
C13 H13B 0.9900 .
C14 O8 1.431(3) .
C14 H14A 0.9900 .
C14 H14B 0.9900 .
N1 H1 0.8800 .
N2 H2A 0.8800 .
N2 H2B 0.8800 .
O3 H3 0.8400 .
O6 H6A 0.8400 .
O9 H9A 0.8400 .
C1 O2 1.229(3) .
C1 O1 1.300(3) .
C1 C2 1.484(3) .
C2 C2 1.318(5) 2_655
C2 H2 0.9500 .
O1 H1A 0.8400 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1W H1B O9 0.85 1.99 2.762(3) 149.6 6_566
O1W H1C O9 0.85 1.95 2.768(3) 160.6 2_565
O2W H2C O5 0.85 1.92 2.705(3) 153.6 .
O2W H2D O1W 0.85 1.87 2.685(3) 158.7 .
N1 H1 O5 0.88 2.08 2.914(3) 158.8 .
N2 H2A N3 0.88 2.24 3.113(3) 174.2 2
N2 H2B O2W 0.88 2.09 2.969(3) 177.7 .
O3 H3 O2 0.84 1.82 2.659(2) 177.7 6_566
O6 H6A O7 0.84 1.72 2.561(2) 175.5 .
O9 H9A O2W 0.84 1.89 2.722(3) 173.7 2
O1 H1A N5 0.84 1.73 2.567(3) 177.2 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_4
N3 C3 C5 N5 179.2(2) .
N4 C3 C5 N5 -0.8(3) .
N3 C3 C5 C8 -1.2(4) .
N4 C3 C5 C8 178.8(2) .
C3 C5 C8 O7 178.3(2) .
N5 C5 C8 O7 -2.2(4) .
C3 C5 C8 N1 -0.6(3) .
N5 C5 C8 N1 178.9(2) .
O5 C7 C9 C10 178.2(3) .
O6 C7 C9 C10 -1.3(4) .
C7 C9 C10 C12 -177.9(2) .
C9 C10 C12 O4 -5.5(4) .
C9 C10 C12 O3 173.8(3) .
O9 C13 C14 O8 66.8(3) .
N3 C4 N1 C8 -1.9(4) .
N2 C4 N1 C8 177.7(2) .
O7 C8 N1 C4 -176.9(2) .
C5 C8 N1 C4 2.1(3) .
N2 C4 N3 C3 -179.5(2) .
N1 C4 N3 C3 0.0(3) .
C5 C3 N3 C4 1.5(4) .
N4 C3 N3 C4 -178.5(2) .
N5 C6 N4 C3 -0.5(3) .
N5 C6 N4 C11 175.5(2) .
N3 C3 N4 C6 -179.2(2) .
C5 C3 N4 C6 0.8(3) .
N3 C3 N4 C11 4.8(4) .
C5 C3 N4 C11 -175.2(2) .
O8 C11 N4 C6 106.3(3) .
O8 C11 N4 C3 -78.4(3) .
N4 C6 N5 C5 0.0(3) .
C3 C5 N5 C6 0.5(3) .
C8 C5 N5 C6 -179.0(3) .
N4 C11 O8 C14 -73.6(2) .
C13 C14 O8 C11 -177.6(2) .
O2 C1 C2 C2 -3.9(3) 2_655
O1 C1 C2 C2 176.02(13) 2_655
