# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelxl
_database_code_depnum_ccdc_archive 'CCDC 947423'
_audit_update_record             
;
2013-06-26 deposited with the CCDC.
2015-07-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H14 F N3 O, 2(H2 O)'

_chemical_formula_sum            'C19 H18 F N3 O3'
_chemical_formula_weight         355.36

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

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

_cell_length_a                   8.6739(4)
_cell_length_b                   9.7386(4)
_cell_length_c                   11.1516(5)
_cell_angle_alpha                75.1390(10)
_cell_angle_beta                 74.865(2)
_cell_angle_gamma                88.181(2)
_cell_volume                     878.28(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7061
_cell_measurement_theta_min      2.16
_cell_measurement_theta_max      26.44

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             372
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9536
_exptl_absorpt_correction_T_max  0.9836
_exptl_absorpt_process_details   'SADABS (Bruker, 2004)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15680
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_sigmaI/netI    0.0168
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.17
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3108
_reflns_number_gt                2579
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'


_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement.  R-factors based on F² 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/[σ²(Fo²)+(0.0512P)²+0.2106P] where P=(Fo²+2Fc²)/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     SHELXL
_refine_ls_extinction_coef       0.021(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3108
_refine_ls_number_parameters     266
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0384
_refine_ls_wR_factor_ref         0.1124
_refine_ls_wR_factor_gt          0.1055
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.001
_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
C1' C -0.0304(2) 1.1647(2) 1.39740(16) 0.0610(5) Uani 0.369(3) 1 d P A 1
H1' H -0.0711 1.1713 1.4815 0.073 Uiso 0.369(3) 1 calc PR A 1
C1 C -0.0304(2) 1.1647(2) 1.39740(16) 0.0610(5) Uani 0.631(3) 1 d P A 2
F1 F -0.0877(2) 1.1774(2) 1.51718(16) 0.0889(8) Uani 0.631(3) 1 d P A 2
C2 C 0.1288(2) 1.1876(2) 1.34243(16) 0.0581(5) Uani 1 1 d . . .
H2 H 0.1959 1.2102 1.3880 0.070 Uiso 1 1 calc R A 1
C3 C 0.18982(19) 1.17683(17) 1.21805(14) 0.0478(4) Uani 1 1 d . A .
H3 H 0.2989 1.1920 1.1796 0.057 Uiso 1 1 calc R . .
C4 C 0.08997(18) 1.14364(15) 1.15010(13) 0.0405(3) Uani 1 1 d . . .
C5 C -0.0721(2) 1.1218(2) 1.20874(16) 0.0572(4) Uani 1 1 d . A .
H5 H -0.1405 1.1000 1.1639 0.069 Uiso 1 1 calc R . .
C6 C -0.1329(2) 1.1323(2) 1.33350(18) 0.0675(5) Uani 1 1 d . . .
H6 H -0.2417 1.1176 1.3732 0.081 Uiso 1 1 calc R A 1
C7 C 0.15635(17) 1.13244(15) 1.01533(13) 0.0402(3) Uani 1 1 d . A .
C8 C 0.11385(18) 1.23759(15) 0.90774(14) 0.0421(3) Uani 1 1 d . . .
C9 C 0.0123(2) 1.34654(18) 0.92949(16) 0.0546(4) Uani 1 1 d . A .
H9 H -0.0295 1.3548 1.0130 0.065 Uiso 1 1 calc R . .
C10 C -0.0278(2) 1.44295(19) 0.82883(18) 0.0643(5) Uani 1 1 d . . .
H10 H -0.0958 1.5158 0.8445 0.077 Uiso 1 1 calc R A 1
C11 C 0.0328(2) 1.43113(19) 0.70622(17) 0.0604(5) Uani 0.631(3) 1 d PD A 1
H11 H 0.0050 1.4958 0.6386 0.072 Uiso 0.631(3) 1 calc PRD A 1
C11' C 0.0328(2) 1.43113(19) 0.70622(17) 0.0604(5) Uani 0.369(3) 1 d P A 2
F1' F -0.0096(4) 1.5137(3) 0.6064(3) 0.0837(13) Uani 0.369(3) 1 d P A 2
C12 C 0.1339(2) 1.32523(19) 0.68171(16) 0.0617(5) Uani 1 1 d . . .
H12 H 0.1749 1.3181 0.5978 0.074 Uiso 1 1 calc R A 1
C13 C 0.1748(2) 1.22921(17) 0.78164(15) 0.0530(4) Uani 1 1 d . A .
H13 H 0.2442 1.1577 0.7646 0.064 Uiso 1 1 calc R . .
C14 C 0.37323(17) 0.82208(15) 1.04803(13) 0.0385(3) Uani 1 1 d . . .
C15 C 0.40894(17) 0.70817(14) 1.15559(13) 0.0393(3) Uani 1 1 d . . .
C16 C 0.3520(2) 0.70150(17) 1.28435(14) 0.0509(4) Uani 1 1 d . . .
H16 H 0.2910 0.7738 1.3109 0.061 Uiso 1 1 calc R . .
C17 C 0.3867(2) 0.58637(18) 1.37331(16) 0.0597(5) Uani 1 1 d . . .
H17 H 0.3470 0.5834 1.4599 0.072 Uiso 1 1 calc R . .
C18 C 0.5309(3) 0.4889(2) 1.21821(19) 0.0734(6) Uani 1 1 d . . .
H18 H 0.5937 0.4163 1.1942 0.088 Uiso 1 1 calc R . .
C19 C 0.5029(2) 0.59971(17) 1.12316(16) 0.0593(5) Uani 1 1 d . . .
H19 H 0.5470 0.6017 1.0372 0.071 Uiso 1 1 calc R . .
N1 N 0.4730(2) 0.47974(15) 1.34307(14) 0.0660(4) Uani 1 1 d . . .
N2 N 0.29029(16) 0.93221(13) 1.08016(12) 0.0451(3) Uani 1 1 d . A .
N3 N 0.25062(15) 1.03528(12) 0.98351(11) 0.0439(3) Uani 1 1 d . . .
O1 O 0.41632(14) 0.81169(12) 0.93774(9) 0.0542(3) Uani 1 1 d . . .
O2 O 0.50840(18) 1.00477(14) 0.68892(13) 0.0707(4) Uani 1 1 d D . .
O3 O 0.44742(18) 0.18414(14) 1.46933(13) 0.0705(4) Uani 1 1 d D . .
H2A H 0.516(3) 0.935(2) 0.648(2) 0.115(10) Uiso 1 1 d D . .
H2B H 0.462(3) 0.965(3) 0.7724(16) 0.106(8) Uiso 1 1 d D . .
H3A H 0.468(3) 0.2787(17) 1.448(2) 0.116(9) Uiso 1 1 d D . .
H3B H 0.460(3) 0.147(2) 1.5483(17) 0.108(8) Uiso 1 1 d D . .
H2C H 0.260(2) 0.937(2) 1.1575(19) 0.066(6) Uiso 1 1 d . . .


_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 areonly 
 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
C1' C2 1.357(3) . ?
C1' C6 1.364(3) . ?
C1' H1' 0.9300 . ?
C2 C3 1.379(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.384(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.385(2) . ?
C4 C7 1.4934(19) . ?
C5 C6 1.382(2) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N3 1.2891(18) . ?
C7 C8 1.4835(19) . ?
C8 C9 1.386(2) . ?
C8 C13 1.390(2) . ?
C9 C10 1.380(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.364(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.367(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.376(2) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 O1 1.2182(16) . ?
C14 N2 1.3453(18) . ?
C14 C15 1.5016(19) . ?
C15 C16 1.376(2) . ?
C15 C19 1.378(2) . ?
C16 C17 1.377(2) . ?
C16 H16 0.9300 . ?
C17 N1 1.323(2) . ?
C17 H17 0.9300 . ?
C18 N1 1.331(2) . ?
C18 C19 1.370(2) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
N2 N3 1.3800(16) . ?
N2 H2C 0.85(2) . ?
O2 H2A 0.904(16) . ?
O2 H2B 0.900(16) . ?
O3 H3A 0.902(16) . ?
O3 H3B 0.897(16) . ?

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 C1' C6 122.24(16) . . ?
C2 C1' H1' 118.9 . . ?
C6 C1' H1' 118.9 . . ?
C1' C2 C3 119.05(16) . . ?
C1' C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C2 C3 C4 120.50(15) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C5 118.98(14) . . ?
C3 C4 C7 120.35(13) . . ?
C5 C4 C7 120.66(13) . . ?
C6 C5 C4 120.43(16) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C1' C6 C5 118.80(17) . . ?
C1' C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
N3 C7 C8 115.76(12) . . ?
N3 C7 C4 124.40(12) . . ?
C8 C7 C4 119.84(12) . . ?
C9 C8 C13 117.99(14) . . ?
C9 C8 C7 121.32(13) . . ?
C13 C8 C7 120.69(13) . . ?
C10 C9 C8 120.85(15) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C11 C10 C9 119.79(16) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C10 C11 C12 120.68(15) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C11 C12 C13 119.77(16) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C12 C13 C8 120.91(15) . . ?
C12 C13 H13 119.5 . . ?
C8 C13 H13 119.5 . . ?
O1 C14 N2 122.67(13) . . ?
O1 C14 C15 120.38(12) . . ?
N2 C14 C15 116.94(12) . . ?
C16 C15 C19 117.28(14) . . ?
C16 C15 C14 125.21(13) . . ?
C19 C15 C14 117.49(13) . . ?
C15 C16 C17 119.10(15) . . ?
C15 C16 H16 120.5 . . ?
C17 C16 H16 120.5 . . ?
N1 C17 C16 123.99(16) . . ?
N1 C17 H17 118.0 . . ?
C16 C17 H17 118.0 . . ?
N1 C18 C19 123.48(17) . . ?
N1 C18 H18 118.3 . . ?
C19 C18 H18 118.3 . . ?
C18 C19 C15 119.64(16) . . ?
C18 C19 H19 120.2 . . ?
C15 C19 H19 120.2 . . ?
C17 N1 C18 116.46(14) . . ?
C14 N2 N3 117.92(12) . . ?
C14 N2 H2C 121.1(13) . . ?
N3 N2 H2C 120.9(13) . . ?
C7 N3 N2 118.19(12) . . ?
H2A O2 H2B 106.8(19) . . ?
H3A O3 H3B 108.5(19) . . ?

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 C1' C2 C3 -0.5(3) . . . . ?
C1' C2 C3 C4 0.2(3) . . . . ?
C2 C3 C4 C5 0.2(2) . . . . ?
C2 C3 C4 C7 179.85(14) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
C7 C4 C5 C6 180.00(16) . . . . ?
C2 C1' C6 C5 0.3(3) . . . . ?
C4 C5 C6 C1' 0.1(3) . . . . ?
C3 C4 C7 N3 67.1(2) . . . . ?
C5 C4 C7 N3 -113.21(18) . . . . ?
C3 C4 C7 C8 -113.05(16) . . . . ?
C5 C4 C7 C8 66.59(19) . . . . ?
N3 C7 C8 C9 179.42(15) . . . . ?
C4 C7 C8 C9 -0.4(2) . . . . ?
N3 C7 C8 C13 -0.4(2) . . . . ?
C4 C7 C8 C13 179.79(14) . . . . ?
C13 C8 C9 C10 0.5(3) . . . . ?
C7 C8 C9 C10 -179.35(16) . . . . ?
C8 C9 C10 C11 0.2(3) . . . . ?
C9 C10 C11 C12 -0.5(3) . . . . ?
C10 C11 C12 C13 0.2(3) . . . . ?
C11 C12 C13 C8 0.4(3) . . . . ?
C9 C8 C13 C12 -0.8(3) . . . . ?
C7 C8 C13 C12 179.05(16) . . . . ?
O1 C14 C15 C16 -172.85(15) . . . . ?
N2 C14 C15 C16 6.0(2) . . . . ?
O1 C14 C15 C19 5.4(2) . . . . ?
N2 C14 C15 C19 -175.76(15) . . . . ?
C19 C15 C16 C17 -2.1(2) . . . . ?
C14 C15 C16 C17 176.20(15) . . . . ?
C15 C16 C17 N1 0.2(3) . . . . ?
N1 C18 C19 C15 -0.7(3) . . . . ?
C16 C15 C19 C18 2.3(3) . . . . ?
C14 C15 C19 C18 -176.12(17) . . . . ?
C16 C17 N1 C18 1.4(3) . . . . ?
C19 C18 N1 C17 -1.2(3) . . . . ?
O1 C14 N2 N3 1.3(2) . . . . ?
C15 C14 N2 N3 -177.47(12) . . . . ?
C8 C7 N3 N2 -178.11(12) . . . . ?
C4 C7 N3 N2 1.7(2) . . . . ?
C14 N2 N3 C7 172.42(13) . . . . ?

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
C2 H2 O3 0.93 2.55 3.413(2) 153.7 1_565
C16 H16 F1 0.93 2.38 3.173(2) 143.1 2_578
O2 H2A O3 0.904(16) 1.921(16) 2.813(2) 169(2) 2_667
O2 H2B O1 0.900(16) 2.005(19) 2.8521(17) 156(2) .
O3 H3A N1 0.902(16) 2.003(17) 2.8491(19) 156(2) .
O3 H3B O2 0.897(16) 1.933(17) 2.7841(18) 158(2) 1_546

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.131
_refine_diff_density_rms         0.030
