# Supplementary Material (ESI) for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2010

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

_publ_contact_author_name        'Frontera, Antonio'
_publ_contact_author_email       toni.frontera@uib.es

_publ_section_title              
;
Experimental and theoretical study of uracil derivatives:
the crucial role of weak \"I\^a\"I, lone pair\^a\"I and
fluorine\^afluorine noncovalent interactions
;
_publ_requested_category         FO
loop_
_publ_author_name
A.Frontera
M.Barcelo-Oliver
C.Estarellas
A.Garcia-Raso
;
A.Terron
;
D.QuiA+-onero
I.Mata
E.Molins
'P.M.Deya Serra'

# Attachment '- compound 3.cif'

data_mb010210
_database_code_depnum_ccdc_archive 'CCDC 771500'
#TrackingRef '- compound 3.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
5-fluoro-1-(3-hydroxypropyl)pyrimidine-2,4(1H,3H)-dione
;
_chemical_name_common            
5-fluoro-1-(3-hydroxypropyl)pyrimidine-2,4(1H,3H)-dione
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H9 F N2 O3'
_chemical_formula_sum            'C7 H9 F N2 O3'
_chemical_formula_weight         188.16

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.0210(5)
_cell_length_b                   13.1280(11)
_cell_length_c                   13.2385(12)
_cell_angle_alpha                105.164(7)
_cell_angle_beta                 98.715(8)
_cell_angle_gamma                100.835(8)
_cell_volume                     808.48(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    183(2)
_cell_measurement_reflns_used    3118
_cell_measurement_theta_min      2.6440
_cell_measurement_theta_max      32.6073

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             392
_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.89177
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan 5 2010,16:28:46)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      183(2)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur Ruby'
_diffrn_measurement_method       '/o oscillation scan'
_diffrn_detector_area_resol_mean 10.4498
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7496
_diffrn_reflns_av_R_equivalents  0.0497
_diffrn_reflns_av_sigmaI/netI    0.0751
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.65
_diffrn_reflns_theta_max         25.34
_reflns_number_total             2880
_reflns_number_gt                1871
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis RED (Oxford, 2007)'
_computing_cell_refinement       'CrysAlis RED (Oxford, 2007)'
_computing_data_reduction        'CrysAlis RED (Oxford, 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0696P)^2^+0.9620P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2880
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1160
_refine_ls_R_factor_gt           0.0637
_refine_ls_wR_factor_ref         0.1846
_refine_ls_wR_factor_gt          0.1697
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_restrained_S_all      1.135
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.6089(7) 0.1218(3) 0.1616(2) 0.0253(8) Uani 1 1 d . . .
C2 C 0.7612(8) 0.0732(3) 0.0948(3) 0.0236(9) Uani 1 1 d . . .
O2 O 0.7981(6) 0.0973(2) 0.0137(2) 0.0302(7) Uani 1 1 d . . .
N3 N 0.8730(7) -0.0054(3) 0.1245(2) 0.0269(8) Uani 1 1 d . . .
H3 H 0.9736 -0.0350 0.0841 0.032 Uiso 1 1 calc R . .
C4 C 0.8420(9) -0.0423(3) 0.2119(3) 0.0290(10) Uani 1 1 d . . .
O4 O 0.9537(7) -0.1127(3) 0.2300(2) 0.0449(9) Uani 1 1 d . . .
C5 C 0.6699(9) 0.0115(3) 0.2739(3) 0.0282(10) Uani 1 1 d . . .
F5 F 0.6224(5) -0.0204(2) 0.36013(18) 0.0421(7) Uani 1 1 d . . .
C6 C 0.5640(8) 0.0901(3) 0.2506(3) 0.0283(10) Uani 1 1 d . . .
H6 H 0.4586 0.1241 0.2946 0.034 Uiso 1 1 calc R . .
C7 C 0.4918(8) 0.2117(3) 0.1409(3) 0.0283(10) Uani 1 1 d . . .
H7A H 0.3125 0.2067 0.1606 0.034 Uiso 1 1 calc R . .
H7B H 0.4635 0.2043 0.0649 0.034 Uiso 1 1 calc R . .
C8 C 0.6789(8) 0.3217(3) 0.2027(3) 0.0314(10) Uani 1 1 d . . .
H8A H 0.8352 0.3354 0.1691 0.038 Uiso 1 1 calc R . .
H8B H 0.7508 0.3217 0.2750 0.038 Uiso 1 1 calc R . .
C9 C 0.5250(9) 0.4132(4) 0.2075(3) 0.0342(11) Uani 1 1 d . . .
H9A H 0.3669 0.4000 0.2403 0.041 Uiso 1 1 calc R . .
H9B H 0.6478 0.4825 0.2501 0.041 Uiso 1 1 calc R . .
O10 O 0.4341(7) 0.4152(3) 0.1005(2) 0.0424(8) Uani 1 1 d . . .
H10 H 0.3901 0.4726 0.1021 0.064 Uiso 1 1 calc R . .
N11 N 0.1403(7) 0.7123(3) 0.3958(2) 0.0256(8) Uani 1 1 d . . .
C12 C 0.0885(8) 0.6255(3) 0.4356(3) 0.0270(10) Uani 1 1 d . . .
O12 O 0.1708(6) 0.5431(2) 0.4045(2) 0.0352(7) Uani 1 1 d . . .
N13 N -0.0638(7) 0.6373(3) 0.5145(2) 0.0287(8) Uani 1 1 d . . .
H13 H -0.0962 0.5838 0.5407 0.034 Uiso 1 1 calc R . .
C14 C -0.1701(9) 0.7248(4) 0.5563(3) 0.0313(10) Uani 1 1 d . . .
O14 O -0.3009(7) 0.7272(3) 0.6272(2) 0.0448(9) Uani 1 1 d . . .
C15 C -0.1073(9) 0.8100(3) 0.5077(3) 0.0273(9) Uani 1 1 d . . .
F15 F -0.2070(6) 0.8981(2) 0.5433(2) 0.0439(7) Uani 1 1 d . . .
C16 C 0.0395(9) 0.8021(3) 0.4318(3) 0.0288(10) Uani 1 1 d . . .
H16 H 0.0747 0.8590 0.4023 0.035 Uiso 1 1 calc R . .
C17 C 0.2779(8) 0.7021(3) 0.3036(3) 0.0281(10) Uani 1 1 d . . .
H17A H 0.4080 0.6566 0.3082 0.034 Uiso 1 1 calc R . .
H17B H 0.3817 0.7734 0.3063 0.034 Uiso 1 1 calc R . .
C18 C 0.0687(9) 0.6531(4) 0.1978(3) 0.0332(10) Uani 1 1 d . . .
H18A H 0.0044 0.5757 0.1861 0.040 Uiso 1 1 calc R . .
H18B H -0.0901 0.6850 0.2020 0.040 Uiso 1 1 calc R . .
C19 C 0.1865(9) 0.6709(4) 0.1036(3) 0.0364(11) Uani 1 1 d . . .
H19A H 0.0408 0.6445 0.0394 0.044 Uiso 1 1 calc R . .
H19B H 0.2605 0.7480 0.1162 0.044 Uiso 1 1 calc R . .
O20 O 0.3977(7) 0.6155(3) 0.0895(2) 0.0439(9) Uani 1 1 d . . .
H20 H 0.4265 0.6086 0.0290 0.066 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0324(19) 0.024(2) 0.0251(17) 0.0101(15) 0.0102(14) 0.0125(15)
C2 0.027(2) 0.023(2) 0.024(2) 0.0069(18) 0.0060(17) 0.0119(18)
O2 0.0423(17) 0.0332(18) 0.0270(15) 0.0162(14) 0.0157(13) 0.0208(14)
N3 0.037(2) 0.024(2) 0.0278(18) 0.0097(15) 0.0163(15) 0.0187(15)
C4 0.044(3) 0.020(2) 0.028(2) 0.0100(19) 0.0109(19) 0.011(2)
O4 0.073(2) 0.040(2) 0.0430(19) 0.0253(17) 0.0252(16) 0.0360(18)
C5 0.042(2) 0.021(2) 0.027(2) 0.0118(19) 0.0146(18) 0.0095(19)
F5 0.0652(18) 0.0411(16) 0.0357(14) 0.0233(13) 0.0259(12) 0.0209(13)
C6 0.035(2) 0.026(2) 0.026(2) 0.0055(19) 0.0129(18) 0.0100(19)
C7 0.033(2) 0.025(2) 0.029(2) 0.0077(19) 0.0052(18) 0.0138(18)
C8 0.033(2) 0.030(3) 0.035(2) 0.016(2) 0.0058(18) 0.0088(19)
C9 0.042(3) 0.034(3) 0.030(2) 0.020(2) 0.0070(19) 0.003(2)
O10 0.070(2) 0.045(2) 0.0290(16) 0.0197(15) 0.0201(15) 0.0338(18)
N11 0.038(2) 0.022(2) 0.0219(17) 0.0106(15) 0.0105(14) 0.0101(15)
C12 0.036(2) 0.028(3) 0.021(2) 0.0117(19) 0.0076(17) 0.010(2)
O12 0.058(2) 0.0269(18) 0.0369(17) 0.0175(14) 0.0283(15) 0.0236(15)
N13 0.050(2) 0.0205(19) 0.0269(18) 0.0145(15) 0.0189(16) 0.0159(16)
C14 0.040(3) 0.034(3) 0.026(2) 0.013(2) 0.0099(19) 0.014(2)
O14 0.074(2) 0.042(2) 0.0417(18) 0.0238(16) 0.0399(17) 0.0321(17)
C15 0.043(3) 0.018(2) 0.025(2) 0.0063(18) 0.0113(18) 0.0160(19)
F15 0.0742(19) 0.0317(16) 0.0456(15) 0.0197(13) 0.0314(13) 0.0336(14)
C16 0.044(3) 0.022(2) 0.025(2) 0.0124(19) 0.0075(19) 0.0114(19)
C17 0.034(2) 0.029(2) 0.029(2) 0.0145(19) 0.0156(18) 0.0098(19)
C18 0.034(2) 0.039(3) 0.031(2) 0.013(2) 0.0105(19) 0.012(2)
C19 0.048(3) 0.041(3) 0.031(2) 0.017(2) 0.015(2) 0.024(2)
O20 0.061(2) 0.051(2) 0.0410(19) 0.0258(17) 0.0272(16) 0.0351(17)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.367(5) . ?
N1 C6 1.384(5) . ?
N1 C7 1.482(5) . ?
C2 O2 1.226(4) . ?
C2 N3 1.377(5) . ?
N3 C4 1.385(5) . ?
N3 H3 0.8600 . ?
C4 O4 1.223(5) . ?
C4 C5 1.435(6) . ?
C5 C6 1.328(6) . ?
C5 F5 1.353(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.509(6) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.539(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 O10 1.429(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
O10 H10 0.8200 . ?
N11 C16 1.370(5) . ?
N11 C12 1.374(5) . ?
N11 C17 1.481(5) . ?
C12 O12 1.223(5) . ?
C12 N13 1.379(5) . ?
N13 C14 1.378(5) . ?
N13 H13 0.8600 . ?
C14 O14 1.222(5) . ?
C14 C15 1.438(6) . ?
C15 C16 1.328(6) . ?
C15 F15 1.347(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.518(6) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.511(5) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 O20 1.402(5) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
O20 H20 0.8200 . ?

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
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C6 121.3(3) . . ?
C2 N1 C7 120.3(3) . . ?
C6 N1 C7 118.4(3) . . ?
O2 C2 N1 122.8(3) . . ?
O2 C2 N3 121.6(4) . . ?
N1 C2 N3 115.6(3) . . ?
C2 N3 C4 127.5(3) . . ?
C2 N3 H3 116.2 . . ?
C4 N3 H3 116.2 . . ?
O4 C4 N3 121.2(4) . . ?
O4 C4 C5 126.7(4) . . ?
N3 C4 C5 112.0(3) . . ?
C6 C5 F5 120.6(4) . . ?
C6 C5 C4 122.8(4) . . ?
F5 C5 C4 116.6(3) . . ?
C5 C6 N1 120.7(4) . . ?
C5 C6 H6 119.6 . . ?
N1 C6 H6 119.6 . . ?
N1 C7 C8 112.1(3) . . ?
N1 C7 H7A 109.2 . . ?
C8 C7 H7A 109.2 . . ?
N1 C7 H7B 109.2 . . ?
C8 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C7 C8 C9 111.8(3) . . ?
C7 C8 H8A 109.3 . . ?
C9 C8 H8A 109.3 . . ?
C7 C8 H8B 109.3 . . ?
C9 C8 H8B 109.3 . . ?
H8A C8 H8B 107.9 . . ?
O10 C9 C8 108.1(4) . . ?
O10 C9 H9A 110.1 . . ?
C8 C9 H9A 110.1 . . ?
O10 C9 H9B 110.1 . . ?
C8 C9 H9B 110.1 . . ?
H9A C9 H9B 108.4 . . ?
C9 O10 H10 109.5 . . ?
C16 N11 C12 121.2(3) . . ?
C16 N11 C17 119.7(3) . . ?
C12 N11 C17 118.7(3) . . ?
O12 C12 N11 123.2(4) . . ?
O12 C12 N13 121.5(3) . . ?
N11 C12 N13 115.3(4) . . ?
C14 N13 C12 127.5(3) . . ?
C14 N13 H13 116.3 . . ?
C12 N13 H13 116.3 . . ?
O14 C14 N13 122.1(4) . . ?
O14 C14 C15 125.4(4) . . ?
N13 C14 C15 112.5(4) . . ?
C16 C15 F15 121.8(4) . . ?
C16 C15 C14 122.0(4) . . ?
F15 C15 C14 116.2(3) . . ?
C15 C16 N11 121.6(4) . . ?
C15 C16 H16 119.2 . . ?
N11 C16 H16 119.2 . . ?
N11 C17 C18 111.5(3) . . ?
N11 C17 H17A 109.3 . . ?
C18 C17 H17A 109.3 . . ?
N11 C17 H17B 109.3 . . ?
C18 C17 H17B 109.3 . . ?
H17A C17 H17B 108.0 . . ?
C19 C18 C17 112.9(4) . . ?
C19 C18 H18A 109.0 . . ?
C17 C18 H18A 109.0 . . ?
C19 C18 H18B 109.0 . . ?
C17 C18 H18B 109.0 . . ?
H18A C18 H18B 107.8 . . ?
O20 C19 C18 109.7(3) . . ?
O20 C19 H19A 109.7 . . ?
C18 C19 H19A 109.7 . . ?
O20 C19 H19B 109.7 . . ?
C18 C19 H19B 109.7 . . ?
H19A C19 H19B 108.2 . . ?
C19 O20 H20 109.5 . . ?

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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N1 C2 O2 177.9(4) . . . . ?
C7 N1 C2 O2 -3.2(6) . . . . ?
C6 N1 C2 N3 -2.3(5) . . . . ?
C7 N1 C2 N3 176.6(3) . . . . ?
O2 C2 N3 C4 -178.2(4) . . . . ?
N1 C2 N3 C4 1.9(6) . . . . ?
C2 N3 C4 O4 -179.7(4) . . . . ?
C2 N3 C4 C5 0.3(6) . . . . ?
O4 C4 C5 C6 177.6(4) . . . . ?
N3 C4 C5 C6 -2.4(6) . . . . ?
O4 C4 C5 F5 -1.3(6) . . . . ?
N3 C4 C5 F5 178.8(3) . . . . ?
F5 C5 C6 N1 -179.1(3) . . . . ?
C4 C5 C6 N1 2.1(6) . . . . ?
C2 N1 C6 C5 0.4(6) . . . . ?
C7 N1 C6 C5 -178.5(4) . . . . ?
C2 N1 C7 C8 -94.5(4) . . . . ?
C6 N1 C7 C8 84.4(4) . . . . ?
N1 C7 C8 C9 -163.5(3) . . . . ?
C7 C8 C9 O10 -62.0(4) . . . . ?
C16 N11 C12 O12 178.8(4) . . . . ?
C17 N11 C12 O12 6.3(6) . . . . ?
C16 N11 C12 N13 -1.5(5) . . . . ?
C17 N11 C12 N13 -174.0(3) . . . . ?
O12 C12 N13 C14 -179.6(4) . . . . ?
N11 C12 N13 C14 0.7(6) . . . . ?
C12 N13 C14 O14 -179.3(4) . . . . ?
C12 N13 C14 C15 0.3(6) . . . . ?
O14 C14 C15 C16 179.1(4) . . . . ?
N13 C14 C15 C16 -0.5(6) . . . . ?
O14 C14 C15 F15 -1.2(6) . . . . ?
N13 C14 C15 F15 179.2(3) . . . . ?
F15 C15 C16 N11 -179.9(3) . . . . ?
C14 C15 C16 N11 -0.3(6) . . . . ?
C12 N11 C16 C15 1.3(6) . . . . ?
C17 N11 C16 C15 173.8(4) . . . . ?
C16 N11 C17 C18 -85.3(4) . . . . ?
C12 N11 C17 C18 87.3(4) . . . . ?
N11 C17 C18 C19 163.3(4) . . . . ?
C17 C18 C19 O20 64.9(5) . . . . ?

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
N3 H3 O2 0.86 1.98 2.836(4) 176.8 2_755
O10 H10 O20 0.82 1.92 2.710(4) 161.2 .
N13 H13 O12 0.86 1.98 2.841(4) 177.8 2_566
O20 H20 O10 0.82 1.92 2.729(4) 167.7 2_665

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        25.34
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.066

# Attachment '- compound 5.cif'

#\#CIF_1.1

# CIF produced by WinGX routine CIF_UPDATE
# Created on 2009-03-12 at 14:56:19
# Using CIFtbx version 2.6.2 16 Jun 1998

# Dictionary name : cif_core.dic
# Dictionary vers : 2.3
# Request file : c:\wingx\files\archive.dat
# CIF files read : pm135 struct difabs dreduc

data_pm135
_database_code_depnum_ccdc_archive 'CCDC 771501'
#TrackingRef '- compound 5.cif'

_audit_creation_date             2009-03-12T14:56:19-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
?
;
_chemical_formula_moiety         'C9 H11 F1 N2 O4, H2 O'
_chemical_formula_sum            'C9 H13 F N2 O5'
_chemical_formula_weight         248.21
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.440(5)
_cell_length_b                   5.117(2)
_cell_length_c                   26.516(11)
_cell_angle_alpha                90
_cell_angle_beta                 95.37(4)
_cell_angle_gamma                90
_cell_volume                     1140.1(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      1.54
_cell_measurement_theta_max      11.97
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.21
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             520
_exptl_special_details           
;
?
;

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details   
;
Walker, N. & Stuart, D (1983) Acta. Cryst. A39, 158-166
;
_exptl_absorpt_correction_T_min  0.964
_exptl_absorpt_correction_T_max  0.973

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#

_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_orient_matrix_type       
;
x-axis points to radiation source
the matrix is specified in reciprocal space
;
_diffrn_orient_matrix_ub_11      -0.040815
_diffrn_orient_matrix_ub_12      0.152889
_diffrn_orient_matrix_ub_13      0.018436
_diffrn_orient_matrix_ub_21      0.073456
_diffrn_orient_matrix_ub_22      0.118184
_diffrn_orient_matrix_ub_23      -0.01675
_diffrn_orient_matrix_ub_31      -0.084258
_diffrn_orient_matrix_ub_32      0.029204
_diffrn_orient_matrix_ub_33      -0.028537
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'non-profiled omega scans'
_diffrn_standards_number         2
_diffrn_standards_interval_time  60
_diffrn_standards_decay_%        -1
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
2 1 -2
1 1 -3

_diffrn_reflns_av_R_equivalents  0.0605
_diffrn_reflns_av_unetI/netI     0.0988
_diffrn_reflns_number            2040
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.54
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_full        24.97
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_reflns_number_total             1990
_reflns_number_gt                930
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#

_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1990
_refine_ls_number_parameters     166
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.1651
_refine_ls_R_factor_gt           0.0675
_refine_ls_wR_factor_ref         0.2683
_refine_ls_wR_factor_gt          0.2066
_refine_ls_goodness_of_fit_ref   0.791
_refine_ls_restrained_S_all      0.791
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.24
_refine_diff_density_rms         0.061

#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
_atom_site_disorder_assembly
_atom_site_disorder_group
C2 C 0.0882(7) -0.2803(11) 0.4455(2) 0.0495(14) Uani 1 1 d . . .
C4 C 0.2546(6) -0.0338(11) 0.51075(19) 0.0499(14) Uani 1 1 d . . .
C5 C 0.3022(6) 0.1133(11) 0.4695(2) 0.0528(15) Uani 1 1 d . . .
C6 C 0.2557(6) 0.0674(11) 0.4212(2) 0.0539(15) Uani 1 1 d . . .
H6 H 0.2953 0.1667 0.3958 0.065 Uiso 1 1 calc R . .
C7 C 0.0892(6) -0.1742(11) 0.35550(19) 0.0511(14) Uani 1 1 d . . .
H7A H 0.0699 -0.3593 0.3499 0.061 Uiso 1 1 calc R . .
H7B H 0.1708 -0.1204 0.3342 0.061 Uiso 1 1 calc R . .
C8 C -0.0634(6) -0.0231(11) 0.34012(18) 0.0487(14) Uani 1 1 d . . .
H8A H -0.141 -0.0584 0.364 0.058 Uiso 1 1 calc R . .
H8B H -0.0412 0.163 0.3408 0.058 Uiso 1 1 calc R . .
C9 C -0.1312(6) -0.1033(11) 0.28688(19) 0.0523(15) Uani 1 1 d . . .
H9A H -0.1589 -0.2873 0.2871 0.063 Uiso 1 1 calc R . .
H9B H -0.0497 -0.0806 0.2638 0.063 Uiso 1 1 calc R . .
C10 C -0.2766(6) 0.0523(11) 0.2676(2) 0.0512(14) Uani 1 1 d . . .
H10A H -0.3559 0.0367 0.2916 0.061 Uiso 1 1 calc R . .
H10B H -0.2475 0.2352 0.2659 0.061 Uiso 1 1 calc R . .
C11 C -0.3479(7) -0.0321(11) 0.2172(2) 0.0522(14) Uani 1 1 d . . .
F5 F 0.4068(5) 0.3093(7) 0.48235(14) 0.0819(13) Uani 1 1 d . . .
N1 N 0.1471(5) -0.1311(8) 0.40918(16) 0.0467(11) Uani 1 1 d . . .
N3 N 0.1452(5) -0.2284(9) 0.49460(17) 0.0511(12) Uani 1 1 d D . .
H3 H 0.098(6) -0.319(9) 0.5163(17) 0.061 Uiso 1 1 d D . .
O2 O -0.0089(5) -0.4571(8) 0.43542(14) 0.0648(12) Uani 1 1 d . . .
O4 O 0.2975(5) -0.0081(9) 0.55575(15) 0.0686(13) Uani 1 1 d . . .
O12 O -0.2981(5) -0.2004(9) 0.19169(16) 0.0738(14) Uani 1 1 d . . .
O13 O -0.4762(5) 0.1053(10) 0.20109(17) 0.0750(14) Uani 1 1 d D . .
H13 H -0.516(9) 0.071(16) 0.1720(14) 0.113 Uiso 1 1 d D . .
OW O -0.6046(8) 0.0162(11) 0.10901(19) 0.107(2) Uani 1 1 d D . .
HW1 H -0.626(12) -0.142(9) 0.091(3) 0.16 Uiso 1 1 d D . .
HW2 H -0.637(12) 0.162(11) 0.089(3) 0.16 Uiso 1 1 d D . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C2 0.050(3) 0.048(3) 0.051(3) 0.009(3) 0.004(3) -0.005(3)
C4 0.047(3) 0.058(4) 0.046(3) -0.005(3) 0.008(2) -0.001(3)
C5 0.050(3) 0.046(3) 0.063(4) -0.001(3) 0.005(3) -0.012(3)
C6 0.049(3) 0.049(3) 0.064(4) 0.007(3) 0.010(3) -0.011(3)
C7 0.054(3) 0.050(3) 0.051(3) -0.006(3) 0.012(3) -0.002(3)
C8 0.054(3) 0.050(3) 0.044(3) -0.002(2) 0.012(2) -0.003(3)
C9 0.055(3) 0.055(3) 0.047(3) -0.004(3) 0.009(3) 0.001(3)
C10 0.046(3) 0.053(3) 0.054(3) -0.004(3) 0.003(2) -0.001(3)
C11 0.058(4) 0.045(3) 0.055(3) -0.001(3) 0.009(3) -0.010(3)
F5 0.089(3) 0.078(3) 0.079(3) -0.010(2) 0.009(2) -0.036(2)
N1 0.046(3) 0.048(3) 0.046(2) 0.004(2) 0.005(2) -0.005(2)
N3 0.049(3) 0.061(3) 0.045(3) 0.010(2) 0.010(2) -0.003(2)
O2 0.073(3) 0.060(3) 0.060(2) 0.010(2) -0.001(2) -0.030(2)
O4 0.074(3) 0.082(3) 0.050(2) -0.008(2) 0.007(2) -0.019(2)
O12 0.073(3) 0.089(3) 0.058(2) -0.020(2) -0.003(2) 0.016(3)
O13 0.070(3) 0.078(3) 0.073(3) -0.015(2) -0.013(2) 0.020(3)
OW 0.140(5) 0.098(4) 0.074(3) -0.013(3) -0.036(3) 0.033(4)

#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C2 O2 1.233(6) . ?
C2 N1 1.358(7) . ?
C2 N3 1.372(7) . ?
C4 O4 1.221(6) . ?
C4 N3 1.398(7) . ?
C4 C5 1.417(8) . ?
C5 C6 1.324(7) . ?
C5 F5 1.358(6) . ?
C6 N1 1.386(6) . ?
C6 H6 0.93 . ?
C7 N1 1.478(6) . ?
C7 C8 1.525(7) . ?
C7 H7A 0.97 . ?
C7 H7B 0.97 . ?
C8 C9 1.529(7) . ?
C8 H8A 0.97 . ?
C8 H8B 0.97 . ?
C9 C10 1.511(7) . ?
C9 H9A 0.97 . ?
C9 H9B 0.97 . ?
C10 C11 1.477(7) . ?
C10 H10A 0.97 . ?
C10 H10B 0.97 . ?
C11 O12 1.196(6) . ?
C11 O13 1.328(7) . ?
N3 H3 0.87(5) . ?
O13 H13 0.83(2) . ?
OW HW1 0.95(5) . ?
OW HW2 0.94(6) . ?

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
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 C2 N1 122.6(5) . . ?
O2 C2 N3 120.9(5) . . ?
N1 C2 N3 116.4(5) . . ?
O4 C4 N3 120.2(5) . . ?
O4 C4 C5 128.2(5) . . ?
N3 C4 C5 111.6(5) . . ?
C6 C5 F5 120.0(5) . . ?
C6 C5 C4 124.9(5) . . ?
F5 C5 C4 115.0(5) . . ?
C5 C6 N1 118.9(5) . . ?
C5 C6 H6 120.6 . . ?
N1 C6 H6 120.6 . . ?
N1 C7 C8 112.1(4) . . ?
N1 C7 H7A 109.2 . . ?
C8 C7 H7A 109.2 . . ?
N1 C7 H7B 109.2 . . ?
C8 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C9 C8 C7 110.2(4) . . ?
C9 C8 H8A 109.6 . . ?
C7 C8 H8A 109.6 . . ?
C9 C8 H8B 109.6 . . ?
C7 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
C8 C9 C10 113.2(4) . . ?
C8 C9 H9A 108.9 . . ?
C10 C9 H9A 108.9 . . ?
C8 C9 H9B 108.9 . . ?
C10 C9 H9B 108.9 . . ?
H9A C9 H9B 107.8 . . ?
C11 C10 C9 113.7(5) . . ?
C11 C10 H10A 108.8 . . ?
C9 C10 H10A 108.8 . . ?
C11 C10 H10B 108.8 . . ?
C9 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
O12 C11 O13 121.2(5) . . ?
O12 C11 C10 126.0(6) . . ?
O13 C11 C10 112.8(5) . . ?
C2 N1 C6 121.8(5) . . ?
C2 N1 C7 119.2(4) . . ?
C6 N1 C7 118.9(4) . . ?
C4 N3 C2 126.3(5) . . ?
C4 N3 H3 121(4) . . ?
C2 N3 H3 113(4) . . ?
C11 O13 H13 116(6) . . ?
HW1 OW HW2 111(4) . . ?

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
N3 H3 O2 0.87(5) 1.92(5) 2.785(6) 175(5) 3_546
O13 H13 OW 0.83(2) 1.79(5) 2.617(6) 177(9) .
OW HW1 O4 0.95(5) 2.09(6) 3.036(7) 173(9) 4_455
OW HW2 O4 0.94(6) 2.03(7) 2.966(7) 171(8) 4_465