# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_rp10141
_database_code_depnum_ccdc_archive 'CCDC 1881809'
_audit_update_record             
;
2018-11-28 deposited with the CCDC.
2019-02-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C14 H10 N2 O'
_chemical_formula_sum            'C14 H10 N2 O'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            yellow

_diffrn_ambient_temperature      297(2)
_chemical_formula_weight         222.24

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_int_tables_number      14
_chemical_absolute_configuration ?

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                   12.1056(8)
_cell_length_b                   7.8020(5)
_cell_length_c                   11.6256(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.574(5)
_cell_angle_gamma                90.00
_cell_volume                     1088.43(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    1097
_cell_measurement_theta_min      3.4570
_cell_measurement_theta_max      28.5050
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             464
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.93253
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) 
(compiled Dec  3 2012,18:21:49) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_exptl_special_details           
; 
 ? 
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5091
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_sigmaI/netI    0.0433
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.11
_diffrn_reflns_theta_max         29.18
_reflns_number_total             2537
_reflns_number_gt                1574
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
; 
CrysAlis CCD, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_cell_refinement       
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_data_reduction        
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0616P)²+0.0405P] where P=(Fo²+2Fc²)/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         2537
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0957
_refine_ls_R_factor_gt           0.0537
_refine_ls_wR_factor_ref         0.1399
_refine_ls_wR_factor_gt          0.1163
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_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
O O 0.91648(10) 0.23085(16) 0.06346(9) 0.0573(4) Uani 1 1 d . . .
N1 N 0.92007(11) 0.08995(17) 0.23654(10) 0.0415(4) Uani 1 1 d . . .
N2 N 0.75556(13) 0.00379(19) 0.31192(12) 0.0524(4) Uani 1 1 d . . .
C1 C 0.86473(14) 0.1653(2) 0.13564(13) 0.0424(4) Uani 1 1 d . . .
C2 C 0.74360(15) 0.1596(2) 0.12790(13) 0.0440(4) Uani 1 1 d . . .
C3 C 0.67746(17) 0.2387(2) 0.03569(16) 0.0593(5) Uani 1 1 d . . .
H3A H 0.7107 0.2911 -0.0229 0.071 Uiso 1 1 calc R . .
C4 C 0.56413(19) 0.2395(3) 0.03109(18) 0.0758(7) Uani 1 1 d . . .
H4A H 0.5205 0.2927 -0.0305 0.091 Uiso 1 1 calc R . .
C5 C 0.51390(18) 0.1614(3) 0.1180(2) 0.0795(7) Uani 1 1 d . . .
H5A H 0.4367 0.1629 0.1144 0.095 Uiso 1 1 calc R . .
C6 C 0.57720(17) 0.0820(3) 0.20908(18) 0.0672(6) Uani 1 1 d . . .
H6A H 0.5427 0.0284 0.2663 0.081 Uiso 1 1 calc R . .
C7 C 0.69339(15) 0.0815(2) 0.21624(14) 0.0473(5) Uani 1 1 d . . .
C8 C 0.86157(16) 0.0127(2) 0.31720(14) 0.0491(5) Uani 1 1 d . . .
H8A H 0.9034 -0.0375 0.3813 0.059 Uiso 1 1 calc R . .
C9 C 1.04010(14) 0.0974(2) 0.26107(13) 0.0423(4) Uani 1 1 d . . .
C10 C 1.10578(15) 0.0337(2) 0.18199(14) 0.0497(5) Uani 1 1 d . . .
H10A H 1.0732 -0.0126 0.1119 0.060 Uiso 1 1 calc R . .
C11 C 1.21983(17) 0.0395(2) 0.20839(17) 0.0607(5) Uani 1 1 d . . .
H11A H 1.2645 -0.0023 0.1555 0.073 Uiso 1 1 calc R . .
C12 C 1.26850(17) 0.1067(3) 0.31233(18) 0.0655(6) Uani 1 1 d . . .
H12A H 1.3457 0.1105 0.3293 0.079 Uiso 1 1 calc R . .
C13 C 1.20267(17) 0.1684(3) 0.39140(17) 0.0608(5) Uani 1 1 d . . .
H13A H 1.2355 0.2124 0.4621 0.073 Uiso 1 1 calc R . .
C14 C 1.08835(16) 0.1647(2) 0.36564(14) 0.0494(5) Uani 1 1 d . . .
H14A H 1.0438 0.2074 0.4184 0.059 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
O 0.0603(9) 0.0700(9) 0.0445(7) 0.0132(6) 0.0180(6) -0.0065(6)
N1 0.0465(9) 0.0428(8) 0.0373(7) 0.0026(6) 0.0130(6) -0.0012(6)
N2 0.0553(10) 0.0591(10) 0.0461(8) 0.0041(7) 0.0184(7) -0.0055(8)
C1 0.0526(11) 0.0391(9) 0.0373(9) -0.0028(7) 0.0124(7) -0.0034(8)
C2 0.0515(11) 0.0414(9) 0.0399(9) -0.0070(7) 0.0097(8) -0.0057(8)
C3 0.0630(14) 0.0656(13) 0.0482(11) 0.0024(9) 0.0030(9) -0.0094(10)
C4 0.0596(15) 0.0938(18) 0.0694(14) 0.0105(12) -0.0089(11) -0.0067(12)
C5 0.0469(13) 0.1031(18) 0.0870(16) 0.0010(14) 0.0036(11) -0.0109(13)
C6 0.0552(13) 0.0839(15) 0.0646(13) -0.0017(11) 0.0160(10) -0.0149(11)
C7 0.0497(11) 0.0490(11) 0.0451(10) -0.0070(8) 0.0138(8) -0.0072(8)
C8 0.0584(12) 0.0513(11) 0.0404(9) 0.0066(7) 0.0173(8) -0.0004(9)
C9 0.0479(10) 0.0375(9) 0.0435(9) 0.0063(7) 0.0134(7) 0.0022(8)
C10 0.0553(12) 0.0468(10) 0.0502(10) -0.0041(8) 0.0189(8) -0.0027(9)
C11 0.0593(13) 0.0567(12) 0.0715(13) 0.0028(10) 0.0287(10) 0.0053(10)
C12 0.0461(12) 0.0730(14) 0.0779(15) 0.0122(11) 0.0097(10) 0.0048(10)
C13 0.0589(13) 0.0681(13) 0.0533(11) 0.0060(9) -0.0010(9) 0.0012(11)
C14 0.0583(12) 0.0513(11) 0.0398(10) 0.0038(8) 0.0112(8) 0.0067(9)

_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
O C1 1.2237(17) . ?
N1 C1 1.401(2) . ?
N1 C8 1.3854(19) . ?
N1 C9 1.445(2) . ?
N2 C8 1.279(2) . ?
N2 C7 1.397(2) . ?
C1 C2 1.458(2) . ?
C2 C7 1.400(2) . ?
C2 C3 1.395(3) . ?
C3 C4 1.366(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.387(3) . ?
C4 H4A 0.9300 . ?
C5 C6 1.371(3) . ?
C5 H5A 0.9300 . ?
C6 C7 1.398(2) . ?
C6 H6A 0.9300 . ?
C8 H8A 0.9300 . ?
C9 C10 1.385(2) . ?
C9 C14 1.381(2) . ?
C10 C11 1.375(2) . ?
C10 H10A 0.9300 . ?
C11 C12 1.376(3) . ?
C11 H11A 0.9300 . ?
C12 C13 1.380(3) . ?
C12 H12A 0.9300 . ?
C13 C14 1.377(3) . ?
C13 H13A 0.9300 . ?
C14 H14A 0.9300 . ?

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
C1 N1 C8 121.23(14) . . ?
C1 N1 C9 120.39(12) . . ?
C8 N1 C9 118.33(14) . . ?
C8 N2 C7 116.55(14) . . ?
O C1 N1 121.20(16) . . ?
O C1 C2 124.89(16) . . ?
N1 C1 C2 113.90(13) . . ?
C7 C2 C3 119.72(17) . . ?
C7 C2 C1 119.88(16) . . ?
C3 C2 C1 120.33(15) . . ?
C4 C3 C2 120.28(18) . . ?
C4 C3 H3A 119.9 . . ?
C2 C3 H3A 119.9 . . ?
C3 C4 C5 120.3(2) . . ?
C3 C4 H4A 119.9 . . ?
C5 C4 H4A 119.9 . . ?
C6 C5 C4 120.5(2) . . ?
C6 C5 H5A 119.8 . . ?
C4 C5 H5A 119.8 . . ?
C5 C6 C7 120.20(18) . . ?
C5 C6 H6A 119.9 . . ?
C7 C6 H6A 119.9 . . ?
C2 C7 C6 119.05(18) . . ?
C2 C7 N2 122.18(16) . . ?
C6 C7 N2 118.76(15) . . ?
N2 C8 N1 126.19(16) . . ?
N2 C8 H8A 116.9 . . ?
N1 C8 H8A 116.9 . . ?
C10 C9 C14 120.52(17) . . ?
C10 C9 N1 120.33(15) . . ?
C14 C9 N1 119.13(14) . . ?
C9 C10 C11 119.17(17) . . ?
C9 C10 H10A 120.4 . . ?
C11 C10 H10A 120.4 . . ?
C12 C11 C10 120.64(17) . . ?
C12 C11 H11A 119.7 . . ?
C10 C11 H11A 119.7 . . ?
C11 C12 C13 119.98(19) . . ?
C11 C12 H12A 120.0 . . ?
C13 C12 H12A 120.0 . . ?
C14 C13 C12 120.00(19) . . ?
C14 C13 H13A 120.0 . . ?
C12 C13 H13A 120.0 . . ?
C13 C14 C9 119.70(16) . . ?
C13 C14 H14A 120.2 . . ?
C9 C14 H14A 120.2 . . ?

_diffrn_measured_fraction_theta_max 0.860
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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_rp10145
_database_code_depnum_ccdc_archive 'CCDC 1881810'
_audit_update_record             
;
2018-11-28 deposited with the CCDC.
2019-02-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C14 H9 F N2 O'
_chemical_formula_sum            'C14 H9 F N2 O'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            brown

_diffrn_ambient_temperature      297(2)
_chemical_formula_weight         240.23

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           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_int_tables_number      14
_chemical_absolute_configuration ?

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                   12.4895(9)
_cell_length_b                   7.7667(5)
_cell_length_c                   11.5802(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.718(6)
_cell_angle_gamma                90.00
_cell_volume                     1115.59(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    1186
_cell_measurement_theta_min      3.1900
_cell_measurement_theta_max      27.1130
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.37
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             496
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.77825
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) 
(compiled Dec  3 2012,18:21:49) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_exptl_special_details           
; 
 ? 
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5038
_diffrn_reflns_av_R_equivalents  0.0629
_diffrn_reflns_av_sigmaI/netI    0.0736
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.09
_diffrn_reflns_theta_max         29.12
_reflns_number_total             2592
_reflns_number_gt                1565
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
; 
CrysAlis CCD, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_cell_refinement       
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_data_reduction        
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0789P)²+0.0000P] where P=(Fo²+2Fc²)/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         2592
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0998
_refine_ls_R_factor_gt           0.0659
_refine_ls_wR_factor_ref         0.1854
_refine_ls_wR_factor_gt          0.1548
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001

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
F F -0.37691(11) 0.1203(2) 0.65911(13) 0.0835(5) Uani 1 1 d . . .
O O 0.06765(12) 0.22387(19) 0.93510(11) 0.0533(5) Uani 1 1 d . . .
N1 N 0.06557(13) 0.0863(2) 0.76072(13) 0.0386(4) Uani 1 1 d . . .
N2 N 0.22554(14) -0.0016(2) 0.68397(14) 0.0492(5) Uani 1 1 d . . .
C1 C 0.11847(16) 0.1592(2) 0.86191(15) 0.0392(5) Uani 1 1 d . . .
C2 C 0.23534(16) 0.1519(2) 0.86897(16) 0.0405(5) Uani 1 1 d . . .
C3 C 0.29845(19) 0.2288(3) 0.9627(2) 0.0554(6) Uani 1 1 d . . .
H3A H 0.2659 0.2817 1.0217 0.066 Uiso 1 1 calc R . .
C4 C 0.4087(2) 0.2255(3) 0.9670(2) 0.0706(8) Uani 1 1 d . . .
H4A H 0.4507 0.2765 1.0294 0.085 Uiso 1 1 calc R . .
C5 C 0.4578(2) 0.1480(4) 0.8806(2) 0.0720(8) Uani 1 1 d . . .
H5A H 0.5326 0.1469 0.8850 0.086 Uiso 1 1 calc R . .
C6 C 0.39702(18) 0.0715(3) 0.7871(2) 0.0596(7) Uani 1 1 d . . .
H6A H 0.4307 0.0189 0.7288 0.072 Uiso 1 1 calc R . .
C7 C 0.28455(16) 0.0738(3) 0.78067(17) 0.0436(5) Uani 1 1 d . . .
C8 C 0.12300(17) 0.0092(3) 0.67953(17) 0.0454(5) Uani 1 1 d . . .
H8A H 0.0829 -0.0397 0.6151 0.054 Uiso 1 1 calc R . .
C9 C -0.05061(15) 0.0953(2) 0.73639(16) 0.0386(5) Uani 1 1 d . . .
C10 C -0.11609(17) 0.0310(3) 0.81415(18) 0.0468(5) Uani 1 1 d . . .
H10A H -0.0860 -0.0175 0.8839 0.056 Uiso 1 1 calc R . .
C11 C -0.22643(18) 0.0392(3) 0.7877(2) 0.0538(6) Uani 1 1 d . . .
H11A H -0.2718 -0.0031 0.8393 0.065 Uiso 1 1 calc R . .
C12 C -0.26799(17) 0.1110(3) 0.6840(2) 0.0542(6) Uani 1 1 d . . .
C13 C -0.20531(19) 0.1735(3) 0.60486(19) 0.0520(6) Uani 1 1 d . . .
H13A H -0.2362 0.2193 0.5345 0.062 Uiso 1 1 calc R . .
C14 C -0.09435(16) 0.1670(3) 0.63200(16) 0.0439(5) Uani 1 1 d . . .
H14A H -0.0495 0.2106 0.5803 0.053 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
F 0.0413(8) 0.1058(12) 0.1020(12) -0.0063(10) 0.0026(7) 0.0011(8)
O 0.0540(10) 0.0695(10) 0.0375(8) -0.0122(7) 0.0107(6) 0.0097(7)
N1 0.0418(10) 0.0418(9) 0.0336(9) -0.0023(7) 0.0099(7) 0.0000(7)
N2 0.0478(11) 0.0560(11) 0.0460(10) -0.0040(9) 0.0154(8) 0.0039(9)
C1 0.0465(12) 0.0393(11) 0.0326(10) 0.0035(8) 0.0085(8) 0.0048(9)
C2 0.0452(12) 0.0384(10) 0.0378(10) 0.0086(9) 0.0049(8) 0.0052(9)
C3 0.0566(14) 0.0616(14) 0.0463(12) -0.0026(11) -0.0008(10) 0.0075(11)
C4 0.0575(16) 0.0806(18) 0.0688(17) -0.0075(14) -0.0135(12) 0.0040(14)
C5 0.0437(14) 0.093(2) 0.0783(17) 0.0039(17) 0.0011(12) 0.0052(13)
C6 0.0482(14) 0.0697(16) 0.0633(14) 0.0009(12) 0.0165(11) 0.0098(12)
C7 0.0444(12) 0.0435(11) 0.0436(12) 0.0075(9) 0.0083(9) 0.0044(9)
C8 0.0502(13) 0.0484(12) 0.0388(11) -0.0068(9) 0.0109(9) -0.0011(10)
C9 0.0391(11) 0.0391(11) 0.0389(11) -0.0048(9) 0.0093(8) 0.0003(8)
C10 0.0519(13) 0.0466(12) 0.0436(11) 0.0019(10) 0.0131(9) 0.0018(10)
C11 0.0490(14) 0.0549(13) 0.0611(14) -0.0006(11) 0.0218(11) -0.0036(10)
C12 0.0400(12) 0.0548(13) 0.0678(15) -0.0109(12) 0.0063(10) 0.0003(10)
C13 0.0529(14) 0.0572(13) 0.0441(12) -0.0036(11) -0.0015(9) 0.0012(11)
C14 0.0478(12) 0.0484(12) 0.0368(10) -0.0031(9) 0.0100(8) -0.0047(9)

_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
F C12 1.359(2) . ?
O C1 1.225(2) . ?
N1 C8 1.384(2) . ?
N1 C1 1.396(2) . ?
N1 C9 1.447(2) . ?
N2 C8 1.278(2) . ?
N2 C7 1.395(2) . ?
C1 C2 1.453(3) . ?
C2 C7 1.392(3) . ?
C2 C3 1.399(3) . ?
C3 C4 1.372(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.373(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.382(3) . ?
C5 H5A 0.9300 . ?
C6 C7 1.398(3) . ?
C6 H6A 0.9300 . ?
C8 H8A 0.9300 . ?
C9 C14 1.384(3) . ?
C9 C10 1.379(3) . ?
C10 C11 1.378(3) . ?
C10 H10A 0.9300 . ?
C11 C12 1.370(3) . ?
C11 H11A 0.9300 . ?
C12 C13 1.363(3) . ?
C13 C14 1.386(3) . ?
C13 H13A 0.9300 . ?
C14 H14A 0.9300 . ?

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
C8 N1 C1 120.91(16) . . ?
C8 N1 C9 118.45(15) . . ?
C1 N1 C9 120.61(15) . . ?
C8 N2 C7 115.94(17) . . ?
O C1 N1 120.97(18) . . ?
O C1 C2 125.13(18) . . ?
N1 C1 C2 113.89(16) . . ?
C7 C2 C3 119.9(2) . . ?
C7 C2 C1 120.15(17) . . ?
C3 C2 C1 119.86(19) . . ?
C4 C3 C2 119.5(2) . . ?
C4 C3 H3A 120.3 . . ?
C2 C3 H3A 120.3 . . ?
C3 C4 C5 120.9(2) . . ?
C3 C4 H4A 119.5 . . ?
C5 C4 H4A 119.5 . . ?
C4 C5 C6 120.6(2) . . ?
C4 C5 H5A 119.7 . . ?
C6 C5 H5A 119.7 . . ?
C7 C6 C5 119.5(2) . . ?
C7 C6 H6A 120.2 . . ?
C5 C6 H6A 120.2 . . ?
C2 C7 C6 119.59(19) . . ?
C2 C7 N2 122.35(18) . . ?
C6 C7 N2 118.06(19) . . ?
N2 C8 N1 126.70(18) . . ?
N2 C8 H8A 116.7 . . ?
N1 C8 H8A 116.7 . . ?
C14 C9 C10 120.83(19) . . ?
C14 C9 N1 118.29(17) . . ?
C10 C9 N1 120.87(17) . . ?
C11 C10 C9 119.50(19) . . ?
C11 C10 H10A 120.3 . . ?
C9 C10 H10A 120.3 . . ?
C10 C11 C12 118.7(2) . . ?
C10 C11 H11A 120.6 . . ?
C12 C11 H11A 120.6 . . ?
F C12 C13 118.5(2) . . ?
F C12 C11 118.4(2) . . ?
C13 C12 C11 123.1(2) . . ?
C12 C13 C14 118.2(2) . . ?
C12 C13 H13A 120.9 . . ?
C14 C13 H13A 120.9 . . ?
C13 C14 C9 119.7(2) . . ?
C13 C14 H14A 120.2 . . ?
C9 C14 H14A 120.2 . . ?

_diffrn_measured_fraction_theta_max 0.864
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.064

