# Electronic Supplementary Material (ESI) for ChemComm.
# 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_ja
_audit_block_doi                 10.5517/ccdc.csd.cc210vpm
_database_code_depnum_ccdc_archive 'CCDC 1877660'
_audit_update_record             
;
2018-11-08 deposited with the CCDC.
2019-02-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H15 F2 N3 O4'
_chemical_formula_weight         339.30

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   P2(1)/n

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.3068(4)
_cell_length_b                   14.1708(8)
_cell_length_c                   13.3787(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.617(3)
_cell_angle_gamma                90.00
_cell_volume                     1557.08(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3584
_cell_measurement_theta_min      2.11
_cell_measurement_theta_max      27.66

_exptl_crystal_description       bar
_exptl_crystal_colour            COLORLESS
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10735
_diffrn_reflns_av_R_equivalents  0.0127
_diffrn_reflns_av_sigmaI/netI    0.0143
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.11
_diffrn_reflns_theta_max         27.66
_reflns_number_total             3584
_reflns_number_gt                3027
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0545P)²+0.5000P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3584
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0403
_refine_ls_wR_factor_ref         0.1113
_refine_ls_wR_factor_gt          0.1050
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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
F1 F 0.22336(12) 0.57188(6) 0.80875(7) 0.0529(3) Uani 1 1 d . . .
O4 O 0.49861(15) 0.37640(7) 1.04387(7) 0.0491(3) Uani 1 1 d . . .
O3 O 0.21826(14) 0.36322(9) 0.57543(7) 0.0480(3) Uani 1 1 d . . .
N3 N 0.06668(15) 0.28165(8) 0.67619(8) 0.0370(3) Uani 1 1 d . . .
H3 H 0.0335 0.2363 0.6355 0.044 Uiso 1 1 calc R . .
F2 F 0.22822(12) 0.55065(7) 0.64979(8) 0.0566(3) Uani 1 1 d . . .
N1 N 0.38819(13) 0.40601(8) 0.78224(8) 0.0315(2) Uani 1 1 d . . .
O1 O -0.09640(13) 0.47618(8) 0.64370(8) 0.0472(3) Uani 1 1 d . . .
N2 N 0.43256(14) 0.43504(8) 0.88480(8) 0.0353(3) Uani 1 1 d . . .
H2 H 0.4402 0.4935 0.9021 0.042 Uiso 1 1 calc R . .
C8 C 0.20700(14) 0.41362(9) 0.75121(8) 0.0256(2) Uani 1 1 d . . .
C10 C 0.44432(18) 0.27319(10) 0.89510(11) 0.0388(3) Uani 1 1 d . . .
H10A H 0.3418 0.2424 0.9009 0.047 Uiso 1 1 calc R . .
H10B H 0.5335 0.2306 0.9185 0.047 Uiso 1 1 calc R . .
C13 C 0.16190(16) 0.51733(9) 0.72898(10) 0.0332(3) Uani 1 1 d . . .
C6 C 0.10145(15) 0.36968(9) 0.82092(9) 0.0280(3) Uani 1 1 d . . .
C11 C 0.46135(17) 0.36522(9) 0.95182(10) 0.0356(3) Uani 1 1 d . . .
C7 C 0.16503(16) 0.35203(9) 0.65369(9) 0.0314(3) Uani 1 1 d . . .
C5 C 0.02513(16) 0.29101(9) 0.77298(10) 0.0332(3) Uani 1 1 d . . .
C12 C -0.02224(18) 0.53671(10) 0.70895(11) 0.0380(3) Uani 1 1 d . . .
O2 O -0.08369(16) 0.59867(9) 0.74989(12) 0.0687(4) Uani 1 1 d . . .
C9 C 0.45014(18) 0.30651(11) 0.78756(11) 0.0408(3) Uani 1 1 d . . .
H9A H 0.5608 0.3042 0.7726 0.049 Uiso 1 1 calc R . .
H9B H 0.3820 0.2669 0.7394 0.049 Uiso 1 1 calc R . .
C1 C 0.07432(19) 0.39446(12) 0.91690(10) 0.0423(3) Uani 1 1 d . . .
H1 H 0.1229 0.4478 0.9489 0.051 Uiso 1 1 calc R . .
C2 C -0.0278(2) 0.33740(16) 0.96439(13) 0.0593(5) Uani 1 1 d . . .
H2A H -0.0468 0.3521 1.0294 0.071 Uiso 1 1 calc R . .
C4 C -0.0775(2) 0.23489(12) 0.81909(14) 0.0518(4) Uani 1 1 d . . .
H4 H -0.1290 0.1827 0.7864 0.062 Uiso 1 1 calc R . .
C3 C -0.1008(2) 0.25932(16) 0.91581(15) 0.0630(5) Uani 1 1 d . . .
H3A H -0.1679 0.2219 0.9492 0.076 Uiso 1 1 calc R . .
C23 C -0.2746(2) 0.48086(15) 0.62331(18) 0.0676(5) Uani 1 1 d . . .
H23A H -0.3179 0.4900 0.6861 0.081 Uiso 1 1 calc R . .
H23B H -0.3083 0.5338 0.5791 0.081 Uiso 1 1 calc R . .
C24 C -0.3373(3) 0.39335(18) 0.57550(16) 0.0733(6) Uani 1 1 d . . .
H24A H -0.2973 0.3858 0.5123 0.110 Uiso 1 1 calc R . .
H24B H -0.4541 0.3954 0.5637 0.110 Uiso 1 1 calc R . .
H24C H -0.3019 0.3411 0.6190 0.110 Uiso 1 1 calc R . .


_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
F1 C13 1.3542(15) . ?
O4 C11 1.2343(16) . ?
O3 C7 1.2065(16) . ?
N3 C7 1.3515(18) . ?
N3 C5 1.3954(17) . ?
N3 H3 0.8600 . ?
F2 C13 1.3504(16) . ?
N1 N2 1.4270(15) . ?
N1 C9 1.4990(18) . ?
N1 C8 1.5040(15) . ?
O1 C12 1.3101(18) . ?
O1 C23 1.466(2) . ?
N2 C11 1.3326(17) . ?
N2 H2 0.8600 . ?
C8 C6 1.5070(16) . ?
C8 C13 1.5347(17) . ?
C8 C7 1.5651(16) . ?
C10 C11 1.5047(19) . ?
C10 C9 1.522(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C13 C12 1.5376(19) . ?
C6 C1 1.3819(17) . ?
C6 C5 1.3907(18) . ?
C5 C4 1.378(2) . ?
C12 O2 1.1896(19) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C1 C2 1.392(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.377(3) . ?
C2 H2A 0.9300 . ?
C4 C3 1.381(3) . ?
C4 H4 0.9300 . ?
C3 H3A 0.9300 . ?
C23 C24 1.455(3) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?

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
C7 N3 C5 112.23(10) . . ?
C7 N3 H3 123.9 . . ?
C5 N3 H3 123.9 . . ?
N2 N1 C9 100.84(10) . . ?
N2 N1 C8 110.39(9) . . ?
C9 N1 C8 113.75(10) . . ?
C12 O1 C23 117.08(13) . . ?
C11 N2 N1 115.30(11) . . ?
C11 N2 H2 122.3 . . ?
N1 N2 H2 122.3 . . ?
N1 C8 C6 116.78(10) . . ?
N1 C8 C13 109.10(10) . . ?
C6 C8 C13 111.59(10) . . ?
N1 C8 C7 106.19(9) . . ?
C6 C8 C7 102.00(10) . . ?
C13 C8 C7 110.80(10) . . ?
C11 C10 C9 101.18(11) . . ?
C11 C10 H10A 111.5 . . ?
C9 C10 H10A 111.5 . . ?
C11 C10 H10B 111.5 . . ?
C9 C10 H10B 111.5 . . ?
H10A C10 H10B 109.4 . . ?
F2 C13 F1 105.59(11) . . ?
F2 C13 C8 111.74(11) . . ?
F1 C13 C8 109.98(10) . . ?
F2 C13 C12 108.24(11) . . ?
F1 C13 C12 106.45(11) . . ?
C8 C13 C12 114.35(11) . . ?
C1 C6 C5 120.38(12) . . ?
C1 C6 C8 131.38(12) . . ?
C5 C6 C8 108.25(10) . . ?
O4 C11 N2 124.68(13) . . ?
O4 C11 C10 127.23(12) . . ?
N2 C11 C10 108.08(11) . . ?
O3 C7 N3 127.06(12) . . ?
O3 C7 C8 125.83(12) . . ?
N3 C7 C8 107.00(10) . . ?
C4 C5 C6 121.75(14) . . ?
C4 C5 N3 128.05(14) . . ?
C6 C5 N3 110.19(11) . . ?
O2 C12 O1 126.78(14) . . ?
O2 C12 C13 122.40(14) . . ?
O1 C12 C13 110.82(12) . . ?
N1 C9 C10 106.11(11) . . ?
N1 C9 H9A 110.5 . . ?
C10 C9 H9A 110.5 . . ?
N1 C9 H9B 110.5 . . ?
C10 C9 H9B 110.5 . . ?
H9A C9 H9B 108.7 . . ?
C6 C1 C2 118.15(16) . . ?
C6 C1 H1 120.9 . . ?
C2 C1 H1 120.9 . . ?
C3 C2 C1 120.44(15) . . ?
C3 C2 H2A 119.8 . . ?
C1 C2 H2A 119.8 . . ?
C5 C4 C3 117.26(16) . . ?
C5 C4 H4 121.4 . . ?
C3 C4 H4 121.4 . . ?
C2 C3 C4 122.00(15) . . ?
C2 C3 H3A 119.0 . . ?
C4 C3 H3A 119.0 . . ?
C24 C23 O1 109.15(17) . . ?
C24 C23 H23A 109.9 . . ?
O1 C23 H23A 109.9 . . ?
C24 C23 H23B 109.9 . . ?
O1 C23 H23B 109.9 . . ?
H23A C23 H23B 108.3 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
C9 N1 N2 C11 -19.60(15) . . . . ?
C8 N1 N2 C11 100.98(13) . . . . ?
N2 N1 C8 C6 -49.59(13) . . . . ?
C9 N1 C8 C6 62.91(14) . . . . ?
N2 N1 C8 C13 78.06(12) . . . . ?
C9 N1 C8 C13 -169.44(10) . . . . ?
N2 N1 C8 C7 -162.48(10) . . . . ?
C9 N1 C8 C7 -49.98(13) . . . . ?
N1 C8 C13 F2 63.72(13) . . . . ?
C6 C8 C13 F2 -165.76(10) . . . . ?
C7 C8 C13 F2 -52.84(14) . . . . ?
N1 C8 C13 F1 -53.21(13) . . . . ?
C6 C8 C13 F1 77.31(13) . . . . ?
C7 C8 C13 F1 -169.77(10) . . . . ?
N1 C8 C13 C12 -172.89(10) . . . . ?
C6 C8 C13 C12 -42.37(14) . . . . ?
C7 C8 C13 C12 70.55(14) . . . . ?
N1 C8 C6 C1 68.98(18) . . . . ?
C13 C8 C6 C1 -57.45(18) . . . . ?
C7 C8 C6 C1 -175.77(14) . . . . ?
N1 C8 C6 C5 -110.50(12) . . . . ?
C13 C8 C6 C5 123.07(11) . . . . ?
C7 C8 C6 C5 4.75(13) . . . . ?
N1 N2 C11 O4 -178.82(13) . . . . ?
N1 N2 C11 C10 2.54(16) . . . . ?
C9 C10 C11 O4 -163.11(15) . . . . ?
C9 C10 C11 N2 15.49(15) . . . . ?
C5 N3 C7 O3 -178.77(13) . . . . ?
C5 N3 C7 C8 4.82(14) . . . . ?
N1 C8 C7 O3 -59.43(16) . . . . ?
C6 C8 C7 O3 177.80(13) . . . . ?
C13 C8 C7 O3 58.91(17) . . . . ?
N1 C8 C7 N3 117.04(11) . . . . ?
C6 C8 C7 N3 -5.74(13) . . . . ?
C13 C8 C7 N3 -124.62(11) . . . . ?
C1 C6 C5 C4 -0.8(2) . . . . ?
C8 C6 C5 C4 178.78(13) . . . . ?
C1 C6 C5 N3 178.17(12) . . . . ?
C8 C6 C5 N3 -2.28(15) . . . . ?
C7 N3 C5 C4 177.09(14) . . . . ?
C7 N3 C5 C6 -1.76(16) . . . . ?
C23 O1 C12 O2 -4.2(3) . . . . ?
C23 O1 C12 C13 175.07(14) . . . . ?
F2 C13 C12 O2 -103.64(17) . . . . ?
F1 C13 C12 O2 9.5(2) . . . . ?
C8 C13 C12 O2 131.10(16) . . . . ?
F2 C13 C12 O1 77.06(15) . . . . ?
F1 C13 C12 O1 -169.84(12) . . . . ?
C8 C13 C12 O1 -48.20(16) . . . . ?
N2 N1 C9 C10 28.20(13) . . . . ?
C8 N1 C9 C10 -89.95(13) . . . . ?
C11 C10 C9 N1 -27.05(14) . . . . ?
C5 C6 C1 C2 1.5(2) . . . . ?
C8 C6 C1 C2 -177.95(14) . . . . ?
C6 C1 C2 C3 -0.9(2) . . . . ?
C6 C5 C4 C3 -0.6(2) . . . . ?
N3 C5 C4 C3 -179.33(15) . . . . ?
C1 C2 C3 C4 -0.5(3) . . . . ?
C5 C4 C3 C2 1.2(3) . . . . ?
C12 O1 C23 C24 -162.68(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        27.66
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.040
####################################################################### 
# 
# 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_ja_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1858543'
_audit_update_record             
;
2018-07-26 deposited with the CCDC.
2019-02-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13.50 H16 F2 N2 O3'
_chemical_formula_weight         292.28

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   P2(1)/c

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                   13.8602(6)
_cell_length_b                   11.4447(6)
_cell_length_c                   9.3074(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.8850(10)
_cell_angle_gamma                90.00
_cell_volume                     1444.74(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3312
_cell_measurement_theta_min      3.01
_cell_measurement_theta_max      27.54

_exptl_crystal_description       BAR
_exptl_crystal_colour            COLORLESS
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             612
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18748
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_sigmaI/netI    0.0302
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.01
_diffrn_reflns_theta_max         27.54
_reflns_number_total             3312
_reflns_number_gt                2295
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0949P)²+0.5812P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3312
_refine_ls_number_parameters     190
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0918
_refine_ls_R_factor_gt           0.0618
_refine_ls_wR_factor_ref         0.1823
_refine_ls_wR_factor_gt          0.1634
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.005
_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
F2 F 0.26384(10) 0.02393(12) 0.10270(15) 0.0561(4) Uani 1 1 d . . .
F1 F 0.39160(10) 0.02742(12) 0.00158(16) 0.0599(4) Uani 1 1 d . . .
N2 N 0.18008(12) -0.16673(15) -0.06273(18) 0.0377(4) Uani 1 1 d . . .
N1 N 0.09757(12) -0.09396(16) -0.05372(18) 0.0406(4) Uani 1 1 d . . .
H1A H 0.0976 -0.0471 0.0186 0.049 Uiso 1 1 calc R . .
C14 C 0.26221(14) -0.10008(18) -0.1042(2) 0.0355(5) Uani 1 1 d . . .
H14A H 0.3059 -0.1590 -0.1330 0.043 Uiso 1 1 calc R . .
O3 O 0.43643(13) -0.19320(19) 0.09272(19) 0.0691(6) Uani 1 1 d . . .
O2 O -0.05774(12) -0.05138(19) -0.17711(19) 0.0670(6) Uani 1 1 d . . .
C13 C 0.23785(15) -0.01676(18) -0.2325(2) 0.0386(5) Uani 1 1 d . . .
C12 C 0.32117(14) -0.04441(19) 0.0356(2) 0.0412(5) Uani 1 1 d . . .
O1 O 0.36159(15) -0.1385(2) 0.2718(2) 0.0713(6) Uani 1 1 d . . .
C11 C 0.02046(15) -0.1041(2) -0.1658(2) 0.0482(6) Uani 1 1 d . . .
C10 C 0.37483(15) -0.1312(2) 0.1502(2) 0.0454(5) Uani 1 1 d . . .
C9 C 0.13546(17) -0.2532(2) -0.1772(3) 0.0515(6) Uani 1 1 d . . .
H9A H 0.1149 -0.3227 -0.1320 0.062 Uiso 1 1 calc R . .
H9B H 0.1826 -0.2756 -0.2360 0.062 Uiso 1 1 calc R . .
C8 C 0.25834(19) -0.0508(2) -0.3659(3) 0.0516(6) Uani 1 1 d . . .
H8A H 0.2868 -0.1235 -0.3738 0.062 Uiso 1 1 calc R . .
C7 C 0.1968(2) 0.0926(2) -0.2244(3) 0.0579(7) Uani 1 1 d . . .
H7A H 0.1822 0.1178 -0.1362 0.070 Uiso 1 1 calc R . .
C6 C 0.2375(2) 0.0208(2) -0.4868(3) 0.0640(7) Uani 1 1 d . . .
H6A H 0.2509 -0.0041 -0.5758 0.077 Uiso 1 1 calc R . .
C5 C 0.04741(17) -0.1929(2) -0.2713(3) 0.0570(7) Uani 1 1 d . . .
H5A H 0.0649 -0.1553 -0.3558 0.068 Uiso 1 1 calc R . .
H5B H -0.0061 -0.2474 -0.3046 0.068 Uiso 1 1 calc R . .
C4 C 0.1773(2) 0.1645(3) -0.3453(3) 0.0743(9) Uani 1 1 d . . .
H4A H 0.1504 0.2382 -0.3379 0.089 Uiso 1 1 calc R . .
C3 C 0.1972(2) 0.1283(3) -0.4767(3) 0.0716(8) Uani 1 1 d . . .
H3A H 0.1833 0.1769 -0.5584 0.086 Uiso 1 1 calc R . .
C2 C 0.5040(3) -0.2697(4) 0.1936(4) 0.1025(14) Uani 1 1 d D . .
H2A H 0.5415 -0.2239 0.2737 0.123 Uiso 1 1 calc R . .
H2B H 0.4666 -0.3279 0.2348 0.123 Uiso 1 1 calc R . .
C1 C 0.5663(4) -0.3234(6) 0.1195(6) 0.181(3) Uani 1 1 d D . .
H1B H 0.6098 -0.3742 0.1850 0.272 Uiso 1 1 calc R . .
H1C H 0.6043 -0.2656 0.0809 0.272 Uiso 1 1 calc R . .
H1D H 0.5288 -0.3683 0.0402 0.272 Uiso 1 1 calc R . .


_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
F2 C12 1.356(2) . ?
F1 C12 1.362(2) . ?
N2 N1 1.431(2) . ?
N2 C14 1.486(2) . ?
N2 C9 1.491(3) . ?
N1 C11 1.336(3) . ?
N1 H1A 0.8600 . ?
C14 C13 1.511(3) . ?
C14 C12 1.526(3) . ?
C14 H14A 0.9800 . ?
O3 C10 1.306(3) . ?
O3 C2 1.471(3) . ?
O2 C11 1.226(3) . ?
C13 C7 1.384(3) . ?
C13 C8 1.385(3) . ?
C12 C10 1.533(3) . ?
O1 C10 1.187(3) . ?
C11 C5 1.513(3) . ?
C9 C5 1.514(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C8 C6 1.374(4) . ?
C8 H8A 0.9300 . ?
C7 C4 1.375(4) . ?
C7 H7A 0.9300 . ?
C6 C3 1.362(4) . ?
C6 H6A 0.9300 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C4 C3 1.372(4) . ?
C4 H4A 0.9300 . ?
C3 H3A 0.9300 . ?
C2 C1 1.357(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 H1D 0.9600 . ?

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
N1 N2 C14 112.38(15) . . ?
N1 N2 C9 102.06(15) . . ?
C14 N2 C9 112.47(16) . . ?
C11 N1 N2 115.12(16) . . ?
C11 N1 H1A 122.4 . . ?
N2 N1 H1A 122.4 . . ?
N2 C14 C13 118.09(16) . . ?
N2 C14 C12 107.30(16) . . ?
C13 C14 C12 113.81(18) . . ?
N2 C14 H14A 105.5 . . ?
C13 C14 H14A 105.5 . . ?
C12 C14 H14A 105.5 . . ?
C10 O3 C2 116.5(2) . . ?
C7 C13 C8 117.8(2) . . ?
C7 C13 C14 123.71(19) . . ?
C8 C13 C14 118.51(19) . . ?
F2 C12 F1 105.95(17) . . ?
F2 C12 C14 111.84(16) . . ?
F1 C12 C14 109.73(17) . . ?
F2 C12 C10 107.44(17) . . ?
F1 C12 C10 106.53(16) . . ?
C14 C12 C10 114.86(18) . . ?
O2 C11 N1 125.2(2) . . ?
O2 C11 C5 127.4(2) . . ?
N1 C11 C5 107.48(18) . . ?
O1 C10 O3 126.5(2) . . ?
O1 C10 C12 124.1(2) . . ?
O3 C10 C12 109.36(18) . . ?
N2 C9 C5 106.11(18) . . ?
N2 C9 H9A 110.5 . . ?
C5 C9 H9A 110.5 . . ?
N2 C9 H9B 110.5 . . ?
C5 C9 H9B 110.5 . . ?
H9A C9 H9B 108.7 . . ?
C6 C8 C13 121.3(2) . . ?
C6 C8 H8A 119.4 . . ?
C13 C8 H8A 119.4 . . ?
C4 C7 C13 120.7(2) . . ?
C4 C7 H7A 119.7 . . ?
C13 C7 H7A 119.7 . . ?
C3 C6 C8 120.1(2) . . ?
C3 C6 H6A 119.9 . . ?
C8 C6 H6A 119.9 . . ?
C11 C5 C9 101.99(18) . . ?
C11 C5 H5A 111.4 . . ?
C9 C5 H5A 111.4 . . ?
C11 C5 H5B 111.4 . . ?
C9 C5 H5B 111.4 . . ?
H5A C5 H5B 109.2 . . ?
C3 C4 C7 120.5(3) . . ?
C3 C4 H4A 119.8 . . ?
C7 C4 H4A 119.8 . . ?
C6 C3 C4 119.7(3) . . ?
C6 C3 H3A 120.2 . . ?
C4 C3 H3A 120.2 . . ?
C1 C2 O3 109.4(3) . . ?
C1 C2 H2A 109.8 . . ?
O3 C2 H2A 109.8 . . ?
C1 C2 H2B 109.8 . . ?
O3 C2 H2B 109.8 . . ?
H2A C2 H2B 108.2 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1D 109.5 . . ?
H1B C1 H1D 109.5 . . ?
H1C C1 H1D 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
C14 N2 N1 C11 104.7(2) . . . . ?
C9 N2 N1 C11 -16.0(2) . . . . ?
N1 N2 C14 C13 -47.5(2) . . . . ?
C9 N2 C14 C13 67.0(2) . . . . ?
N1 N2 C14 C12 82.71(19) . . . . ?
C9 N2 C14 C12 -162.78(17) . . . . ?
N2 C14 C13 C7 77.6(3) . . . . ?
C12 C14 C13 C7 -49.5(3) . . . . ?
N2 C14 C13 C8 -102.9(2) . . . . ?
C12 C14 C13 C8 129.9(2) . . . . ?
N2 C14 C12 F2 -56.7(2) . . . . ?
C13 C14 C12 F2 75.9(2) . . . . ?
N2 C14 C12 F1 -173.92(15) . . . . ?
C13 C14 C12 F1 -41.4(2) . . . . ?
N2 C14 C12 C10 66.1(2) . . . . ?
C13 C14 C12 C10 -161.31(17) . . . . ?
N2 N1 C11 O2 178.4(2) . . . . ?
N2 N1 C11 C5 -0.5(3) . . . . ?
C2 O3 C10 O1 -7.6(4) . . . . ?
C2 O3 C10 C12 171.8(3) . . . . ?
F2 C12 C10 O1 4.1(3) . . . . ?
F1 C12 C10 O1 117.3(3) . . . . ?
C14 C12 C10 O1 -121.0(3) . . . . ?
F2 C12 C10 O3 -175.40(19) . . . . ?
F1 C12 C10 O3 -62.2(2) . . . . ?
C14 C12 C10 O3 59.5(2) . . . . ?
N1 N2 C9 C5 25.5(2) . . . . ?
C14 N2 C9 C5 -95.1(2) . . . . ?
C7 C13 C8 C6 -0.8(4) . . . . ?
C14 C13 C8 C6 179.7(2) . . . . ?
C8 C13 C7 C4 -0.1(4) . . . . ?
C14 C13 C7 C4 179.4(3) . . . . ?
C13 C8 C6 C3 1.0(4) . . . . ?
O2 C11 C5 C9 -162.4(3) . . . . ?
N1 C11 C5 C9 16.5(3) . . . . ?
N2 C9 C5 C11 -25.9(2) . . . . ?
C13 C7 C4 C3 0.8(5) . . . . ?
C8 C6 C3 C4 -0.2(5) . . . . ?
C7 C4 C3 C6 -0.6(5) . . . . ?
C10 O3 C2 C1 -176.9(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.54
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.613
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.052
####################################################################### 
# 
# 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_ja_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1858544'
_audit_update_record             
;
2018-07-26 deposited with the CCDC.
2019-02-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H20 F2 N2 O3'
_chemical_formula_weight         374.38

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   P2(1)/c

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                   11.6732(7)
_cell_length_b                   16.7833(11)
_cell_length_c                   10.3207(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 115.021(2)
_cell_angle_gamma                90.00
_cell_volume                     1832.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4220
_cell_measurement_theta_min      3.10
_cell_measurement_theta_max      27.54

_exptl_crystal_description       BAR
_exptl_crystal_colour            COLORLESS
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            28655
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_sigmaI/netI    0.0226
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.10
_diffrn_reflns_theta_max         27.54
_reflns_number_total             4220
_reflns_number_gt                3156
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0921P)²+0.9712P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4220
_refine_ls_number_parameters     242
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0871
_refine_ls_R_factor_gt           0.0656
_refine_ls_wR_factor_ref         0.1894
_refine_ls_wR_factor_gt          0.1733
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.007
_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
F2 F 0.72636(17) 0.02157(8) 0.81778(15) 0.0663(5) Uani 1 1 d . A .
O3 O 0.49188(17) -0.09814(10) 1.06957(17) 0.0530(4) Uani 1 1 d . . .
N2 N 0.56375(15) -0.10712(9) 0.77210(17) 0.0332(4) Uani 1 1 d . . .
C20 C 0.69937(18) -0.11894(12) 0.8063(2) 0.0349(4) Uani 1 1 d . A .
H20A H 0.7297 -0.1661 0.8674 0.042 Uiso 1 1 calc R . .
F1 F 0.89422(15) -0.05281(12) 0.88572(18) 0.0791(6) Uani 1 1 d . A .
N1 N 0.54732(17) -0.06956(10) 0.88745(18) 0.0386(4) Uani 1 1 d . . .
H1A H 0.5586 -0.0193 0.9043 0.046 Uiso 1 1 calc R . .
C19 C 0.3690(2) -0.18788(12) 0.6370(2) 0.0385(5) Uani 1 1 d . . .
C18 C 0.50032(19) -0.18646(11) 0.7585(2) 0.0340(4) Uani 1 1 d . . .
H18A H 0.5518 -0.2272 0.7404 0.041 Uiso 1 1 calc R . .
C17 C 0.71354(19) -0.13343(11) 0.6687(2) 0.0348(4) Uani 1 1 d . . .
C16 C 0.5036(2) -0.20130(12) 0.9072(2) 0.0406(5) Uani 1 1 d . . .
H16A H 0.4273 -0.2280 0.8996 0.049 Uiso 1 1 calc R . .
H16B H 0.5763 -0.2333 0.9660 0.049 Uiso 1 1 calc R . .
C15 C 0.6418(2) -0.09180(13) 0.5455(2) 0.0456(5) Uani 1 1 d . . .
H15A H 0.5808 -0.0560 0.5449 0.055 Uiso 1 1 calc R . .
O2 O 0.7966(2) 0.02873(12) 1.08530(19) 0.0666(5) Uani 1 1 d . . .
C14 C 0.51277(19) -0.11884(12) 0.9677(2) 0.0382(5) Uani 1 1 d . . .
C13 C 0.8035(2) -0.18683(14) 0.6669(2) 0.0445(5) Uani 1 1 d . . .
H13A H 0.8513 -0.2163 0.7483 0.053 Uiso 1 1 calc R . .
O1 O 0.8270(2) -0.10257(13) 1.1163(2) 0.0838(7) Uani 1 1 d . . .
C12 C 0.8030(2) -0.04367(16) 1.0446(2) 0.0527(6) Uani 1 1 d . A .
C11 C 0.3225(2) -0.12647(15) 0.5396(2) 0.0514(6) Uani 1 1 d . . .
H11A H 0.3707 -0.0807 0.5511 0.062 Uiso 1 1 calc R . .
C10 C 0.8226(2) -0.19647(15) 0.5436(3) 0.0554(6) Uani 1 1 d . . .
H10A H 0.8843 -0.2315 0.5436 0.067 Uiso 1 1 calc R . .
C9 C 0.7509(3) -0.15466(15) 0.4224(3) 0.0586(7) Uani 1 1 d . . .
H9A H 0.7638 -0.1613 0.3400 0.070 Uiso 1 1 calc R . .
C8 C 0.6602(3) -0.10309(15) 0.4227(2) 0.0572(6) Uani 1 1 d . . .
H8A H 0.6105 -0.0754 0.3398 0.069 Uiso 1 1 calc R . .
C7 C 0.7776(2) -0.04712(14) 0.8859(2) 0.0477(5) Uani 1 1 d . . .
C6 C 0.2954(3) -0.25556(16) 0.6164(3) 0.0610(7) Uani 1 1 d . . .
H6A H 0.3250 -0.2980 0.6800 0.073 Uiso 1 1 calc R . .
C4 C 0.2049(3) -0.1323(2) 0.4248(3) 0.0729(8) Uani 1 1 d . . .
H4A H 0.1753 -0.0907 0.3596 0.088 Uiso 1 1 calc R . .
C3 C 0.1323(3) -0.1987(2) 0.4067(3) 0.0833(10) Uani 1 1 d . . .
H3A H 0.0527 -0.2019 0.3308 0.100 Uiso 1 1 calc R . .
C2 C 0.1777(3) -0.2604(2) 0.5013(4) 0.0840(10) Uani 1 1 d . . .
H2A H 0.1291 -0.3061 0.4884 0.101 Uiso 1 1 calc R . .
C5 C 0.7970(9) 0.0515(5) 1.2177(9) 0.0770(17) Uiso 0.470(4) 1 d P A 1
H5A H 0.7770 0.0059 1.2621 0.092 Uiso 0.470(4) 1 calc PR A 1
H5B H 0.7336 0.0922 1.2022 0.092 Uiso 0.470(4) 1 calc PR A 1
C1 C 0.9191(7) 0.0815(5) 1.3088(8) 0.0770(17) Uiso 0.470(4) 1 d P A 1
H1B H 0.9194 0.0983 1.3979 0.116 Uiso 0.470(4) 1 calc PR A 1
H1C H 0.9389 0.1260 1.2636 0.116 Uiso 0.470(4) 1 calc PR A 1
H1D H 0.9811 0.0404 1.3263 0.116 Uiso 0.470(4) 1 calc PR A 1
C5' C 0.8266(5) 0.0334(3) 1.2436(6) 0.0456(14) Uiso 0.470(4) 1 d P A 2
H5'A H 0.7893 0.0819 1.2596 0.055 Uiso 0.470(4) 1 calc PR A 2
H5'B H 0.7854 -0.0110 1.2666 0.055 Uiso 0.470(4) 1 calc PR A 2
C1' C 0.9444(7) 0.0326(5) 1.3317(8) 0.0744(18) Uiso 0.470(4) 1 d P A 2
H1'A H 0.9520 0.0355 1.4279 0.112 Uiso 0.470(4) 1 calc PR A 2
H1'B H 0.9864 0.0776 1.3134 0.112 Uiso 0.470(4) 1 calc PR A 2
H1'C H 0.9827 -0.0157 1.3195 0.112 Uiso 0.470(4) 1 calc PR A 2


_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
F2 C7 1.351(3) . ?
O3 C14 1.226(2) . ?
N2 N1 1.430(2) . ?
N2 C20 1.483(3) . ?
N2 C18 1.501(2) . ?
C20 C17 1.517(2) . ?
C20 C7 1.525(3) . ?
C20 H20A 0.9800 . ?
F1 C7 1.366(3) . ?
N1 C14 1.347(3) . ?
N1 H1A 0.8600 . ?
C19 C11 1.381(3) . ?
C19 C6 1.385(3) . ?
C19 C18 1.515(3) . ?
C18 C16 1.539(3) . ?
C18 H18A 0.9800 . ?
C17 C15 1.381(3) . ?
C17 C13 1.387(3) . ?
C16 C14 1.504(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C15 C8 1.385(3) . ?
C15 H15A 0.9300 . ?
O2 C12 1.298(3) . ?
O2 C5 1.417(9) . ?
O2 C5' 1.521(6) . ?
C13 C10 1.390(3) . ?
C13 H13A 0.9300 . ?
O1 C12 1.195(3) . ?
C12 C7 1.537(3) . ?
C11 C4 1.387(4) . ?
C11 H11A 0.9300 . ?
C10 C9 1.368(4) . ?
C10 H10A 0.9300 . ?
C9 C8 1.369(4) . ?
C9 H9A 0.9300 . ?
C8 H8A 0.9300 . ?
C6 C2 1.387(4) . ?
C6 H6A 0.9300 . ?
C4 C3 1.364(5) . ?
C4 H4A 0.9300 . ?
C3 C2 1.366(5) . ?
C3 H3A 0.9300 . ?
C2 H2A 0.9300 . ?
C5 C1 1.427(11) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 H1D 0.9600 . ?
C5' C1' 1.289(9) . ?
C5' H5'A 0.9700 . ?
C5' H5'B 0.9700 . ?
C1' H1'A 0.9600 . ?
C1' H1'B 0.9600 . ?
C1' H1'C 0.9600 . ?

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
N1 N2 C20 111.52(14) . . ?
N1 N2 C18 103.56(13) . . ?
C20 N2 C18 109.78(14) . . ?
N2 C20 C17 109.09(15) . . ?
N2 C20 C7 110.97(17) . . ?
C17 C20 C7 110.70(16) . . ?
N2 C20 H20A 108.7 . . ?
C17 C20 H20A 108.7 . . ?
C7 C20 H20A 108.7 . . ?
C14 N1 N2 114.93(16) . . ?
C14 N1 H1A 122.5 . . ?
N2 N1 H1A 122.5 . . ?
C11 C19 C6 118.3(2) . . ?
C11 C19 C18 122.60(19) . . ?
C6 C19 C18 119.0(2) . . ?
N2 C18 C19 112.20(15) . . ?
N2 C18 C16 104.30(15) . . ?
C19 C18 C16 114.33(16) . . ?
N2 C18 H18A 108.6 . . ?
C19 C18 H18A 108.6 . . ?
C16 C18 H18A 108.6 . . ?
C15 C17 C13 118.82(19) . . ?
C15 C17 C20 121.16(18) . . ?
C13 C17 C20 119.96(18) . . ?
C14 C16 C18 103.44(15) . . ?
C14 C16 H16A 111.1 . . ?
C18 C16 H16A 111.1 . . ?
C14 C16 H16B 111.1 . . ?
C18 C16 H16B 111.1 . . ?
H16A C16 H16B 109.0 . . ?
C17 C15 C8 120.3(2) . . ?
C17 C15 H15A 119.8 . . ?
C8 C15 H15A 119.8 . . ?
C12 O2 C5 126.0(4) . . ?
C12 O2 C5' 112.2(3) . . ?
C5 O2 C5' 17.2(4) . . ?
O3 C14 N1 124.97(19) . . ?
O3 C14 C16 127.74(19) . . ?
N1 C14 C16 107.29(16) . . ?
C17 C13 C10 120.2(2) . . ?
C17 C13 H13A 119.9 . . ?
C10 C13 H13A 119.9 . . ?
O1 C12 O2 127.2(2) . . ?
O1 C12 C7 121.2(2) . . ?
O2 C12 C7 111.6(2) . . ?
C19 C11 C4 120.7(2) . . ?
C19 C11 H11A 119.6 . . ?
C4 C11 H11A 119.6 . . ?
C9 C10 C13 120.3(2) . . ?
C9 C10 H10A 119.8 . . ?
C13 C10 H10A 119.8 . . ?
C10 C9 C8 119.7(2) . . ?
C10 C9 H9A 120.1 . . ?
C8 C9 H9A 120.1 . . ?
C9 C8 C15 120.6(2) . . ?
C9 C8 H8A 119.7 . . ?
C15 C8 H8A 119.7 . . ?
F2 C7 F1 106.32(19) . . ?
F2 C7 C20 111.23(19) . . ?
F1 C7 C20 108.30(18) . . ?
F2 C7 C12 111.45(19) . . ?
F1 C7 C12 105.08(19) . . ?
C20 C7 C12 113.93(18) . . ?
C19 C6 C2 120.3(3) . . ?
C19 C6 H6A 119.9 . . ?
C2 C6 H6A 119.9 . . ?
C3 C4 C11 120.6(3) . . ?
C3 C4 H4A 119.7 . . ?
C11 C4 H4A 119.7 . . ?
C4 C3 C2 119.3(3) . . ?
C4 C3 H3A 120.3 . . ?
C2 C3 H3A 120.3 . . ?
C3 C2 C6 120.8(3) . . ?
C3 C2 H2A 119.6 . . ?
C6 C2 H2A 119.6 . . ?
O2 C5 C1 109.0(7) . . ?
O2 C5 H5A 109.9 . . ?
C1 C5 H5A 109.9 . . ?
O2 C5 H5B 109.9 . . ?
C1 C5 H5B 109.9 . . ?
H5A C5 H5B 108.3 . . ?
C5 C1 H1B 109.5 . . ?
C5 C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C5 C1 H1D 109.5 . . ?
H1B C1 H1D 109.5 . . ?
H1C C1 H1D 109.5 . . ?
C1' C5' O2 116.7(5) . . ?
C1' C5' H5'A 108.1 . . ?
O2 C5' H5'A 108.1 . . ?
C1' C5' H5'B 108.1 . . ?
O2 C5' H5'B 108.1 . . ?
H5'A C5' H5'B 107.3 . . ?
C5' C1' H1'A 109.5 . . ?
C5' C1' H1'B 109.5 . . ?
H1'A C1' H1'B 109.5 . . ?
C5' C1' H1'C 109.5 . . ?
H1'A C1' H1'C 109.5 . . ?
H1'B C1' H1'C 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
N1 N2 C20 C17 -162.00(15) . . . . ?
C18 N2 C20 C17 83.82(18) . . . . ?
N1 N2 C20 C7 -39.8(2) . . . . ?
C18 N2 C20 C7 -153.96(16) . . . . ?
C20 N2 N1 C14 -102.62(19) . . . . ?
C18 N2 N1 C14 15.4(2) . . . . ?
N1 N2 C18 C19 100.36(17) . . . . ?
C20 N2 C18 C19 -140.45(15) . . . . ?
N1 N2 C18 C16 -23.91(19) . . . . ?
C20 N2 C18 C16 95.28(17) . . . . ?
C11 C19 C18 N2 8.5(3) . . . . ?
C6 C19 C18 N2 -176.11(19) . . . . ?
C11 C19 C18 C16 127.0(2) . . . . ?
C6 C19 C18 C16 -57.6(3) . . . . ?
N2 C20 C17 C15 39.2(2) . . . . ?
C7 C20 C17 C15 -83.2(2) . . . . ?
N2 C20 C17 C13 -143.56(18) . . . . ?
C7 C20 C17 C13 94.1(2) . . . . ?
N2 C18 C16 C14 24.4(2) . . . . ?
C19 C18 C16 C14 -98.54(19) . . . . ?
C13 C17 C15 C8 -0.3(3) . . . . ?
C20 C17 C15 C8 176.9(2) . . . . ?
N2 N1 C14 O3 -178.7(2) . . . . ?
N2 N1 C14 C16 0.5(2) . . . . ?
C18 C16 C14 O3 163.4(2) . . . . ?
C18 C16 C14 N1 -15.8(2) . . . . ?
C15 C17 C13 C10 1.5(3) . . . . ?
C20 C17 C13 C10 -175.80(19) . . . . ?
C5 O2 C12 O1 -10.7(6) . . . . ?
C5' O2 C12 O1 1.2(4) . . . . ?
C5 O2 C12 C7 170.3(5) . . . . ?
C5' O2 C12 C7 -177.8(3) . . . . ?
C6 C19 C11 C4 0.4(4) . . . . ?
C18 C19 C11 C4 175.9(2) . . . . ?
C17 C13 C10 C9 -1.4(3) . . . . ?
C13 C10 C9 C8 0.1(4) . . . . ?
C10 C9 C8 C15 1.1(4) . . . . ?
C17 C15 C8 C9 -1.0(4) . . . . ?
N2 C20 C7 F2 -49.9(2) . . . . ?
C17 C20 C7 F2 71.4(2) . . . . ?
N2 C20 C7 F1 -166.41(17) . . . . ?
C17 C20 C7 F1 -45.1(2) . . . . ?
N2 C20 C7 C12 77.1(2) . . . . ?
C17 C20 C7 C12 -161.65(19) . . . . ?
O1 C12 C7 F2 166.7(3) . . . . ?
O2 C12 C7 F2 -14.2(3) . . . . ?
O1 C12 C7 F1 -78.5(3) . . . . ?
O2 C12 C7 F1 100.5(2) . . . . ?
O1 C12 C7 C20 39.9(3) . . . . ?
O2 C12 C7 C20 -141.1(2) . . . . ?
C11 C19 C6 C2 -0.7(4) . . . . ?
C18 C19 C6 C2 -176.3(3) . . . . ?
C19 C11 C4 C3 0.6(5) . . . . ?
C11 C4 C3 C2 -1.4(5) . . . . ?
C4 C3 C2 C6 1.1(6) . . . . ?
C19 C6 C2 C3 -0.1(5) . . . . ?
C12 O2 C5 C1 103.2(7) . . . . ?
C5' O2 C5 C1 63.0(16) . . . . ?
C12 O2 C5' C1' 80.1(6) . . . . ?
C5 O2 C5' C1' -134(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.54
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.641
_refine_diff_density_min         -0.442
_refine_diff_density_rms         0.081
