# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_tolm202
_audit_block_doi                 10.5517/cc13s5nq
_database_code_depnum_ccdc_archive 'CCDC 1036133'
_audit_update_record             
;
2014-11-26 deposited with the CCDC.
2015-01-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C4 H4 N2 O3'
_chemical_formula_weight         128.09

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           ?
_symmetry_space_group_name_H-M   ?

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

_cell_length_a                   5.561
_cell_length_b                   6.229
_cell_length_c                   16.499
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     571.5
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             264
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9808
_exptl_absorpt_correction_T_max  0.9935
_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3113
_diffrn_reflns_av_R_equivalents  0.1507
_diffrn_reflns_av_sigmaI/netI    0.0818
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.50
_diffrn_reflns_theta_max         24.97
_reflns_number_total             542
_reflns_number_gt                315
_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)+(0.0669P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         542
_refine_ls_number_parameters     55
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0948
_refine_ls_R_factor_gt           0.0553
_refine_ls_wR_factor_ref         0.1425
_refine_ls_wR_factor_gt          0.1257
_refine_ls_goodness_of_fit_ref   0.907
_refine_ls_restrained_S_all      0.907
_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
O1 O -0.0050(4) 0.2500 0.42793(15) 0.0725(11) Uani 1 2 d S . .
O2 O -0.3000(4) 0.2500 0.61435(15) 0.0826(11) Uani 1 2 d S . .
O3 O 0.0927(4) 0.2500 0.58521(15) 0.0643(10) Uani 1 2 d S . .
N1 N -0.5133(7) 0.2500 0.3085(3) 0.1027(18) Uani 1 2 d S . .
N2 N -0.4732(5) 0.2500 0.3749(3) 0.0728(12) Uani 1 2 d S . .
C1 C -0.4219(6) 0.2500 0.4535(2) 0.0620(12) Uani 1 2 d S . .
H1 H -0.5423 0.2500 0.4926 0.074 Uiso 1 2 calc SR . .
C2 C -0.1763(5) 0.2500 0.4749(2) 0.0589(11) Uani 1 2 d S . .
C3 C -0.1375(5) 0.2500 0.5660(2) 0.0556(11) Uani 1 2 d S . .
C4 C 0.1427(6) 0.2500 0.6716(2) 0.0844(17) Uani 1 2 d S . .
H4A H 0.3134 0.2500 0.6802 0.127 Uiso 1 2 calc SR . .
H4B H 0.0738 0.1242 0.6959 0.127 Uiso 0.50 1 calc PR . .
H4C H 0.0738 0.3758 0.6959 0.127 Uiso 0.50 1 calc PR . .

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
O1 0.0472(14) 0.105(3) 0.0652(17) 0.000 0.0139(11) 0.000
O2 0.0459(13) 0.134(3) 0.0682(17) 0.000 0.0141(12) 0.000
O3 0.0391(13) 0.093(3) 0.0607(16) 0.000 0.0052(10) 0.000
N1 0.089(3) 0.140(5) 0.079(3) 0.000 -0.011(2) 0.000
N2 0.0531(18) 0.086(3) 0.079(3) 0.000 0.0004(16) 0.000
C1 0.0484(18) 0.076(4) 0.061(3) 0.000 0.0000(16) 0.000
C2 0.0418(16) 0.066(3) 0.069(2) 0.000 0.0085(17) 0.000
C3 0.0385(16) 0.061(3) 0.067(2) 0.000 0.0078(14) 0.000
C4 0.053(2) 0.135(5) 0.065(3) 0.000 -0.0010(18) 0.000

_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
O1 C2 1.229(3) . ?
O2 C3 1.205(4) . ?
O3 C3 1.319(4) . ?
O3 C4 1.453(5) . ?
N1 N2 1.119(5) . ?
N2 C1 1.327(5) . ?
C1 C2 1.411(4) . ?
C2 C3 1.518(5) . ?

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
C3 O3 C4 114.9(3) . . ?
N1 N2 C1 179.1(4) . . ?
N2 C1 C2 117.0(3) . . ?
O1 C2 C1 126.3(3) . . ?
O1 C2 C3 121.0(3) . . ?
C1 C2 C3 112.7(3) . . ?
O2 C3 O3 124.7(3) . . ?
O2 C3 C2 123.3(3) . . ?
O3 C3 C2 112.1(3) . . ?

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 C1 C2 0.00(6) . . . . ?
N2 C1 C2 O1 0.000(1) . . . . ?
N2 C1 C2 C3 180.000(1) . . . . ?
C4 O3 C3 O2 0.000(1) . . . . ?
C4 O3 C3 C2 180.0 . . . . ?
O1 C2 C3 O2 180.000(1) . . . . ?
C1 C2 C3 O2 0.000(1) . . . . ?
O1 C2 C3 O3 0.000(1) . . . . ?
C1 C2 C3 O3 180.0 . . . . ?

_diffrn_measured_fraction_theta_max 0.977
_diffrn_reflns_theta_full        24.97
_diffrn_measured_fraction_theta_full 0.977
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.055
####################################################################### 
# 
# 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_t220
_audit_block_doi                 10.5517/cc13s5pr
_database_code_depnum_ccdc_archive 'CCDC 1036134'
_audit_update_record             
;
2014-11-26 deposited with the CCDC.
2015-01-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H13 F4 N2 O P'
_chemical_formula_weight         368.26

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

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

_cell_length_a                   14.054(1)
_cell_length_b                   11.4353(6)
_cell_length_c                   21.489(1)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3453.4
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1504
_exptl_absorpt_coefficient_mu    0.206
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9599
_exptl_absorpt_correction_T_max  0.9979
_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19094
_diffrn_reflns_av_R_equivalents  0.0726
_diffrn_reflns_av_sigmaI/netI    0.0409
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.40
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2886
_reflns_number_gt                1779
_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)+(0.1062P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2886
_refine_ls_number_parameters     266
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0992
_refine_ls_R_factor_gt           0.0612
_refine_ls_wR_factor_ref         0.1785
_refine_ls_wR_factor_gt          0.1561
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_restrained_S_all      0.987
_refine_ls_shift/su_max          0.004
_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
P1 P 0.75535(3) 0.01533(5) 0.48102(3) 0.04330(14) Uani 1 1 d . . .
O1 O 0.75937(9) -0.11304(13) 0.48985(7) 0.0550(4) Uani 1 1 d . . .
N1 N 0.75145(10) 0.20189(14) 0.56665(9) 0.0474(5) Uani 1 1 d . . .
H1N H 0.7486 0.2539 0.5378 0.057 Uiso 1 1 calc R . .
N2 N 0.75287(12) 0.22727(16) 0.62801(9) 0.0558(5) Uani 1 1 d . . .
C1 C 0.75701(15) 0.1231(2) 0.65509(11) 0.0565(6) Uani 1 1 d . A .
C2 C 0.75960(14) 0.03170(19) 0.61296(11) 0.0507(6) Uani 1 1 d . . .
H2 H 0.7635 -0.0479 0.6213 0.061 Uiso 1 1 calc R . .
C3 C 0.75501(12) 0.08571(17) 0.55573(10) 0.0439(5) Uani 1 1 d . . .
C4 C 0.75514(3) 0.11610(5) 0.72458(4) 0.0860(9) Uani 1 1 d D . .
C6 C 0.65010(14) 0.05767(17) 0.43914(10) 0.0501(6) Uani 1 1 d . . .
C7 C 0.58243(17) -0.0266(2) 0.42844(14) 0.0739(8) Uani 1 1 d . . .
H7 H 0.5916 -0.1021 0.4433 0.089 Uiso 1 1 calc R . .
C8 C 0.5009(2) 0.0003(3) 0.39566(17) 0.0998(11) Uani 1 1 d . . .
H8 H 0.4567 -0.0581 0.3871 0.120 Uiso 1 1 calc R . .
C9 C 0.4847(2) 0.1097(3) 0.37597(15) 0.1012(11) Uani 1 1 d . . .
H9 H 0.4284 0.1278 0.3554 0.121 Uiso 1 1 calc R . .
C10 C 0.5520(2) 0.1951(3) 0.38639(16) 0.0968(10) Uani 1 1 d . . .
H10 H 0.5413 0.2708 0.3722 0.116 Uiso 1 1 calc R . .
C11 C 0.6358(2) 0.1692(2) 0.41781(14) 0.0767(8) Uani 1 1 d . . .
H11 H 0.6815 0.2267 0.4243 0.092 Uiso 1 1 calc R . .
C12 C 0.85621(14) 0.07283(17) 0.43988(10) 0.0492(6) Uani 1 1 d . . .
C13 C 0.8627(2) 0.0586(3) 0.37764(14) 0.0977(10) Uani 1 1 d . . .
H13 H 0.8116 0.0251 0.3567 0.117 Uiso 1 1 calc R . .
C14 C 0.9417(2) 0.0915(4) 0.34371(16) 0.1223(13) Uani 1 1 d . . .
H14 H 0.9448 0.0785 0.3010 0.147 Uiso 1 1 calc R . .
C15 C 1.01507(19) 0.1436(3) 0.37462(15) 0.0891(9) Uani 1 1 d . . .
H15 H 1.0685 0.1679 0.3526 0.107 Uiso 1 1 calc R . .
C16 C 1.01093(17) 0.1606(2) 0.43737(15) 0.0841(9) Uani 1 1 d . . .
H16 H 1.0616 0.1961 0.4578 0.101 Uiso 1 1 calc R . .
C17 C 0.93185(15) 0.1254(2) 0.47081(12) 0.0676(7) Uani 1 1 d . . .
H17 H 0.9293 0.1367 0.5136 0.081 Uiso 1 1 calc R . .
C5A C 0.85877(6) 0.11236(9) 0.74780(5) 0.160(3) Uani 0.50 1 d PD A 1
H5A H 0.8928 0.1686 0.7215 0.192 Uiso 0.50 1 calc PR A 1
F1A F 0.7581(7) 0.00101(8) 0.73839(17) 0.330(6) Uani 0.50 1 d PD A 1
F2A F 0.70594(14) 0.20100(16) 0.75406(13) 0.303(3) Uani 0.50 1 d PD A 1
F3A F 0.89644(7) 0.00740(11) 0.7330(2) 0.83(3) Uani 0.50 1 d PD A 1
F4A F 0.86207(11) 0.1587(3) 0.80555(6) 1.98(3) Uani 0.50 1 d PD A 1
C5B C 0.82032(6) 0.20004(11) 0.76091(4) 0.160(3) Uani 0.50 1 d PD A 2
H5B H 0.8056 0.2811 0.7496 0.192 Uiso 0.50 1 calc PR A 2
F1B F 0.7744(3) 0.00724(11) 0.74531(15) 0.149(2) Uani 0.50 1 d PD A 2
F2B F 0.66481(7) 0.1095(5) 0.74580(12) 0.1712(19) Uani 0.50 1 d PD A 2
F3B F 0.90568(9) 0.1695(3) 0.73713(14) 0.1208(15) Uani 0.50 1 d PD A 2
F4B F 0.7922(3) 0.1791(3) 0.81997(6) 0.174(2) Uani 0.50 1 d PD A 2

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
P1 0.0567(3) 0.0326(3) 0.0407(3) 0.0029(2) -0.0030(2) -0.0004(2)
O1 0.0772(9) 0.0342(8) 0.0537(9) 0.0032(7) -0.0021(7) -0.0013(6)
N1 0.0665(10) 0.0338(9) 0.0419(10) 0.0026(7) 0.0014(7) 0.0023(7)
N2 0.0795(11) 0.0407(9) 0.0470(11) -0.0004(8) 0.0003(8) 0.0042(8)
C1 0.0790(13) 0.0492(12) 0.0412(12) 0.0016(11) -0.0017(10) 0.0001(10)
C2 0.0703(12) 0.0349(10) 0.0469(13) 0.0038(9) -0.0039(9) 0.0006(9)
C3 0.0504(10) 0.0348(11) 0.0466(12) 0.0024(9) -0.0008(8) 0.0013(8)
C4 0.140(2) 0.0725(17) 0.0453(15) 0.0011(14) -0.0089(14) -0.0051(16)
C6 0.0575(11) 0.0464(11) 0.0464(13) -0.0010(10) -0.0007(9) 0.0007(9)
C7 0.0657(14) 0.0696(15) 0.0863(19) 0.0144(13) -0.0138(12) -0.0144(11)
C8 0.0625(15) 0.108(2) 0.129(3) 0.0178(18) -0.0283(15) -0.0138(14)
C9 0.0671(15) 0.124(2) 0.113(2) 0.013(2) -0.0272(15) 0.0108(17)
C10 0.116(2) 0.0764(18) 0.098(2) 0.0046(16) -0.0396(17) 0.0267(16)
C11 0.0982(17) 0.0508(14) 0.0812(19) 0.0068(13) -0.0293(14) 0.0040(12)
C12 0.0544(11) 0.0414(11) 0.0519(13) 0.0025(10) 0.0006(9) 0.0027(9)
C13 0.0938(17) 0.148(3) 0.0508(17) -0.0025(16) 0.0051(13) -0.0523(17)
C14 0.112(2) 0.191(3) 0.064(2) -0.002(2) 0.0208(17) -0.048(2)
C15 0.0663(14) 0.098(2) 0.103(2) 0.0243(17) 0.0168(14) -0.0118(14)
C16 0.0532(13) 0.095(2) 0.104(2) -0.0061(17) 0.0010(14) -0.0078(12)
C17 0.0533(12) 0.0841(16) 0.0653(16) -0.0049(13) -0.0034(11) -0.0018(11)
C5A 0.298(8) 0.129(5) 0.053(3) -0.020(3) -0.035(4) 0.006(6)
F1A 0.856(16) 0.086(3) 0.049(3) 0.022(2) -0.010(5) -0.182(5)
F2A 0.546(7) 0.326(5) 0.036(2) -0.043(3) -0.008(4) 0.310(5)
F3A 0.314(12) 2.00(10) 0.166(9) -0.07(2) -0.104(9) 0.34(2)
F4A 2.00(6) 2.00(6) 1.94(6) 1.14(5) -0.91(6) 0.68(7)
C5B 0.298(8) 0.129(5) 0.053(3) -0.020(3) -0.035(4) 0.006(6)
F1B 0.310(6) 0.083(3) 0.054(3) 0.002(2) -0.020(3) 0.050(3)
F2B 0.138(2) 0.318(5) 0.057(2) -0.023(3) 0.0429(18) -0.126(3)
F3B 0.094(2) 0.191(4) 0.078(3) 0.008(2) -0.0102(18) -0.049(2)
F4B 0.369(7) 0.123(3) 0.030(2) -0.008(2) -0.020(3) -0.054(4)

_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
P1 O1 1.4812(16) . ?
P1 C12 1.795(2) . ?
P1 C3 1.796(2) . ?
P1 C6 1.798(2) . ?
N1 C3 1.350(2) . ?
N1 N2 1.350(3) . ?
N2 C1 1.327(3) . ?
C1 C2 1.384(3) . ?
C1 C4 1.496(2) . ?
C2 C3 1.378(3) . ?
C4 F1B 1.3495(9) . ?
C4 F2A 1.3497(10) . ?
C4 F1A 1.3497(9) . ?
C4 F2B 1.3510(9) . ?
C4 C5B 1.5395(8) . ?
C4 C5A 1.5401(8) . ?
C6 C11 1.370(3) . ?
C6 C7 1.373(3) . ?
C7 C8 1.380(4) . ?
C8 C9 1.339(4) . ?
C9 C10 1.378(4) . ?
C10 C11 1.389(4) . ?
C12 C13 1.350(4) . ?
C12 C17 1.390(3) . ?
C13 C14 1.380(4) . ?
C14 C15 1.364(4) . ?
C15 C16 1.364(4) . ?
C16 C17 1.383(4) . ?
C5A F4A 1.3500(9) . ?
C5A F3A 1.3501(9) . ?
C5B F3B 1.3500(10) . ?
C5B F4B 1.3504(10) . ?

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
O1 P1 C12 113.32(9) . . ?
O1 P1 C3 109.25(9) . . ?
C12 P1 C3 106.15(9) . . ?
O1 P1 C6 111.25(9) . . ?
C12 P1 C6 107.73(10) . . ?
C3 P1 C6 108.95(9) . . ?
C3 N1 N2 112.37(17) . . ?
C1 N2 N1 103.65(18) . . ?
N2 C1 C2 113.1(2) . . ?
N2 C1 C4 119.04(19) . . ?
C2 C1 C4 127.8(2) . . ?
C3 C2 C1 104.12(19) . . ?
N1 C3 C2 106.73(19) . . ?
N1 C3 P1 126.61(16) . . ?
C2 C3 P1 126.65(16) . . ?
F1B C4 F2A 127.7(2) . . ?
F1B C4 F1A 12.0(4) . . ?
F2A C4 F1A 127.9(3) . . ?
F1B C4 F2B 91.4(3) . . ?
F2A C4 F2B 53.2(3) . . ?
F1A C4 F2B 84.3(5) . . ?
F1B C4 C1 112.07(18) . . ?
F2A C4 C1 116.03(16) . . ?
F1A C4 C1 105.75(19) . . ?
F2B C4 C1 110.88(14) . . ?
F1B C4 C5B 106.77(16) . . ?
F2A C4 C5B 67.57(11) . . ?
F1A C4 C5B 118.6(3) . . ?
F2B C4 C5B 115.0(2) . . ?
C1 C4 C5B 117.54(10) . . ?
F1B C4 C5A 71.22(18) . . ?
F2A C4 C5A 110.64(12) . . ?
F1A C4 C5A 82.7(4) . . ?
F2B C4 C5A 141.06(13) . . ?
C1 C4 C5A 107.96(10) . . ?
C5B C4 C5A 44.79(6) . . ?
C11 C6 C7 119.7(2) . . ?
C11 C6 P1 122.62(17) . . ?
C7 C6 P1 117.70(17) . . ?
C6 C7 C8 120.3(2) . . ?
C9 C8 C7 120.7(3) . . ?
C8 C9 C10 119.6(3) . . ?
C9 C10 C11 120.6(3) . . ?
C6 C11 C10 119.1(2) . . ?
C13 C12 C17 118.3(2) . . ?
C13 C12 P1 119.80(18) . . ?
C17 C12 P1 121.77(18) . . ?
C12 C13 C14 123.0(3) . . ?
C15 C14 C13 118.0(3) . . ?
C16 C15 C14 120.8(3) . . ?
C15 C16 C17 120.4(3) . . ?
C16 C17 C12 119.5(2) . . ?
F4A C5A F3A 123.5(2) . . ?
F4A C5A C4 108.62(8) . . ?
F3A C5A C4 108.60(8) . . ?
F3B C5B F4B 124.7(2) . . ?
F3B C5B C4 100.10(13) . . ?
F4B C5B C4 101.08(15) . . ?

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
C3 N1 N2 C1 -0.3(2) . . . . ?
N1 N2 C1 C2 0.8(2) . . . . ?
N1 N2 C1 C4 -177.19(15) . . . . ?
N2 C1 C2 C3 -1.1(2) . . . . ?
C4 C1 C2 C3 176.75(17) . . . . ?
N2 N1 C3 C2 -0.4(2) . . . . ?
N2 N1 C3 P1 -179.60(13) . . . . ?
C1 C2 C3 N1 0.8(2) . . . . ?
C1 C2 C3 P1 -179.95(14) . . . . ?
O1 P1 C3 N1 -179.73(14) . . . . ?
C12 P1 C3 N1 57.74(17) . . . . ?
C6 P1 C3 N1 -58.01(17) . . . . ?
O1 P1 C3 C2 1.19(19) . . . . ?
C12 P1 C3 C2 -121.33(17) . . . . ?
C6 P1 C3 C2 122.91(17) . . . . ?
N2 C1 C4 F1B -170.5(2) . . . . ?
C2 C1 C4 F1B 11.8(3) . . . . ?
N2 C1 C4 F2A 30.7(2) . . . . ?
C2 C1 C4 F2A -147.0(2) . . . . ?
N2 C1 C4 F1A 178.7(5) . . . . ?
C2 C1 C4 F1A 1.0(5) . . . . ?
N2 C1 C4 F2B 88.9(3) . . . . ?
C2 C1 C4 F2B -88.8(3) . . . . ?
N2 C1 C4 C5B -46.3(2) . . . . ?
C2 C1 C4 C5B 136.00(19) . . . . ?
N2 C1 C4 C5A -94.05(17) . . . . ?
C2 C1 C4 C5A 88.2(2) . . . . ?
O1 P1 C6 C11 -171.1(2) . . . . ?
C12 P1 C6 C11 -46.4(2) . . . . ?
C3 P1 C6 C11 68.4(2) . . . . ?
O1 P1 C6 C7 8.7(2) . . . . ?
C12 P1 C6 C7 133.43(19) . . . . ?
C3 P1 C6 C7 -111.8(2) . . . . ?
C11 C6 C7 C8 0.9(4) . . . . ?
P1 C6 C7 C8 -178.9(2) . . . . ?
C6 C7 C8 C9 -2.7(5) . . . . ?
C7 C8 C9 C10 2.6(5) . . . . ?
C8 C9 C10 C11 -0.9(5) . . . . ?
C7 C6 C11 C10 0.9(4) . . . . ?
P1 C6 C11 C10 -179.3(2) . . . . ?
C9 C10 C11 C6 -0.9(5) . . . . ?
O1 P1 C12 C13 76.1(2) . . . . ?
C3 P1 C12 C13 -164.0(2) . . . . ?
C6 P1 C12 C13 -47.4(2) . . . . ?
O1 P1 C12 C17 -99.54(19) . . . . ?
C3 P1 C12 C17 20.4(2) . . . . ?
C6 P1 C12 C17 136.95(18) . . . . ?
C17 C12 C13 C14 1.5(5) . . . . ?
P1 C12 C13 C14 -174.3(3) . . . . ?
C12 C13 C14 C15 -1.9(6) . . . . ?
C13 C14 C15 C16 1.2(5) . . . . ?
C14 C15 C16 C17 -0.2(5) . . . . ?
C15 C16 C17 C12 -0.3(4) . . . . ?
C13 C12 C17 C16 -0.4(4) . . . . ?
P1 C12 C17 C16 175.33(18) . . . . ?
F1B C4 C5A F4A -99.9(2) . . . . ?
F2A C4 C5A F4A 24.3(2) . . . . ?
F1A C4 C5A F4A -103.5(3) . . . . ?
F2B C4 C5A F4A -32.1(4) . . . . ?
C1 C4 C5A F4A 152.23(18) . . . . ?
C5B C4 C5A F4A 40.92(15) . . . . ?
F1B C4 C5A F3A 36.9(3) . . . . ?
F2A C4 C5A F3A 161.0(2) . . . . ?
F1A C4 C5A F3A 33.2(3) . . . . ?
F2B C4 C5A F3A 104.6(4) . . . . ?
C1 C4 C5A F3A -71.0(2) . . . . ?
C5B C4 C5A F3A 177.7(2) . . . . ?
F1B C4 C5B F3B 68.7(3) . . . . ?
F2A C4 C5B F3B -166.8(2) . . . . ?
F1A C4 C5B F3B 71.1(4) . . . . ?
F2B C4 C5B F3B 168.5(3) . . . . ?
C1 C4 C5B F3B -58.1(2) . . . . ?
C5A C4 C5B F3B 30.03(17) . . . . ?
F1B C4 C5B F4B -59.9(3) . . . . ?
F2A C4 C5B F4B 64.5(2) . . . . ?
F1A C4 C5B F4B -57.6(4) . . . . ?
F2B C4 C5B F4B 39.8(3) . . . . ?
C1 C4 C5B F4B 173.2(2) . . . . ?
C5A C4 C5B F4B -98.6(2) . . . . ?

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
N1 H1N O1 0.86 1.84 2.688(2) 167.8 7_765

_diffrn_measured_fraction_theta_max 0.949
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.949
_refine_diff_density_max         0.410
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.064
####################################################################### 
# 
# 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_tolm221
_audit_block_doi                 10.5517/cc13s5qs
_database_code_depnum_ccdc_archive 'CCDC 1036135'
_audit_update_record             
;
2014-11-26 deposited with the CCDC.
2015-01-23 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 H9 F4 N3 O2'
_chemical_formula_weight         315.23

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           ?
_symmetry_space_group_name_H-M   ?

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

_cell_length_a                   23.325(4)
_cell_length_b                   6.6111(11)
_cell_length_c                   17.954(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.023(15)
_cell_angle_gamma                90.00
_cell_volume                     2741.5(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.527
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1280
_exptl_absorpt_coefficient_mu    0.142
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9723
_exptl_absorpt_correction_T_max  0.9930
_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13070
_diffrn_reflns_av_R_equivalents  0.0863
_diffrn_reflns_av_sigmaI/netI    0.0979
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.08
_diffrn_reflns_theta_max         30.00
_reflns_number_total             3963
_reflns_number_gt                1338
_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)+(0.0667P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3963
_refine_ls_number_parameters     203
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1829
_refine_ls_R_factor_gt           0.0614
_refine_ls_wR_factor_ref         0.1769
_refine_ls_wR_factor_gt          0.1365
_refine_ls_goodness_of_fit_ref   0.825
_refine_ls_restrained_S_all      0.825
_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
F1 F 0.35854(9) 1.0233(2) 0.11846(10) 0.0911(6) Uani 1 1 d . . .
F2 F 0.42111(8) 0.8292(3) 0.18390(9) 0.0902(6) Uani 1 1 d . . .
F3 F 0.45867(11) 1.0441(4) 0.07079(14) 0.1414(10) Uani 1 1 d . . .
F4 F 0.46555(9) 0.7203(4) 0.06076(12) 0.1245(8) Uani 1 1 d . . .
O1 O 0.27336(8) 0.8601(3) 0.22850(11) 0.0788(7) Uani 1 1 d . . .
O2 O 0.17662(9) 0.4111(3) 0.06521(10) 0.0675(6) Uani 1 1 d . . .
N1 N 0.30004(12) 0.4361(5) 0.03936(14) 0.0726(8) Uani 1 1 d . . .
H1N H 0.3069(11) 0.333(4) 0.0233(15) 0.058(9) Uiso 1 1 d . . .
N2 N 0.34178(10) 0.5828(3) 0.04050(12) 0.0639(6) Uani 1 1 d . . .
N3 N 0.21324(9) 0.6633(3) 0.14643(10) 0.0466(5) Uani 1 1 d . . .
C1 C 0.34805(11) 0.6759(4) 0.10370(14) 0.0536(6) Uani 1 1 d . . .
C2 C 0.31278(11) 0.5852(4) 0.16075(14) 0.0550(7) Uani 1 1 d . . .
H2 H 0.3374 0.5274 0.2042 0.066 Uiso 1 1 calc R . .
C3 C 0.27891(12) 0.4227(4) 0.11253(14) 0.0574(7) Uani 1 1 d . . .
H3 H 0.2843 0.2877 0.1349 0.069 Uiso 1 1 calc R . .
C4 C 0.38817(12) 0.8474(4) 0.11532(15) 0.0617(7) Uani 1 1 d . . .
C5 C 0.42829(14) 0.8752(6) 0.05587(18) 0.0802(9) Uani 1 1 d . . .
H5 H 0.4059 0.8814 0.0055 0.096 Uiso 1 1 calc R . .
C6 C 0.26633(12) 0.7227(4) 0.18405(14) 0.0560(7) Uani 1 1 d . . .
C7 C 0.21683(13) 0.4904(4) 0.10371(14) 0.0520(7) Uani 1 1 d . . .
C8 C 0.15959(11) 0.7583(4) 0.15639(12) 0.0495(6) Uani 1 1 d . . .
C9 C 0.14894(13) 0.9549(4) 0.13433(14) 0.0588(7) Uani 1 1 d . . .
H9 H 0.1768 1.0281 0.1135 0.071 Uiso 1 1 calc R . .
C10 C 0.09694(14) 1.0437(5) 0.14316(16) 0.0739(9) Uani 1 1 d . . .
H10 H 0.0897 1.1776 0.1290 0.089 Uiso 1 1 calc R . .
C11 C 0.05586(15) 0.9332(6) 0.17306(19) 0.0871(10) Uani 1 1 d . . .
H11 H 0.0201 0.9906 0.1774 0.105 Uiso 1 1 calc R . .
C12 C 0.06742(14) 0.7390(5) 0.1964(2) 0.0927(11) Uani 1 1 d . . .
H12 H 0.0399 0.6668 0.2183 0.111 Uiso 1 1 calc R . .
C13 C 0.11900(13) 0.6492(4) 0.18793(16) 0.0712(9) Uani 1 1 d . . .
H13 H 0.1265 0.5163 0.2033 0.085 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
F1 0.0947(14) 0.0659(12) 0.1163(15) -0.0081(9) 0.0272(12) 0.0074(10)
F2 0.0846(14) 0.1211(16) 0.0624(11) -0.0065(9) 0.0009(9) -0.0158(11)
F3 0.130(2) 0.169(2) 0.134(2) -0.0211(16) 0.0501(16) -0.0762(19)
F4 0.0754(14) 0.183(2) 0.1211(17) 0.0178(15) 0.0365(13) 0.0398(15)
O1 0.0592(13) 0.0986(16) 0.0804(14) -0.0475(11) 0.0159(10) -0.0135(11)
O2 0.0726(14) 0.0613(12) 0.0670(12) -0.0152(9) 0.0044(10) -0.0076(10)
N1 0.088(2) 0.069(2) 0.0673(17) -0.0207(13) 0.0314(14) -0.0062(15)
N2 0.0641(16) 0.0731(16) 0.0575(14) -0.0112(11) 0.0185(12) -0.0053(13)
N3 0.0495(13) 0.0480(12) 0.0428(11) -0.0039(8) 0.0081(9) -0.0004(10)
C1 0.0484(16) 0.0600(17) 0.0535(15) -0.0047(12) 0.0104(12) 0.0031(13)
C2 0.0510(17) 0.0652(17) 0.0500(14) -0.0016(11) 0.0119(12) 0.0070(13)
C3 0.0667(19) 0.0511(16) 0.0578(16) -0.0042(11) 0.0205(14) 0.0051(13)
C4 0.0537(18) 0.074(2) 0.0579(17) -0.0045(13) 0.0079(14) 0.0040(15)
C5 0.060(2) 0.102(3) 0.079(2) 0.0066(17) 0.0140(17) -0.010(2)
C6 0.0574(18) 0.0648(17) 0.0484(14) -0.0097(12) 0.0168(13) -0.0058(14)
C7 0.0641(19) 0.0438(16) 0.0489(14) 0.0006(11) 0.0111(13) 0.0004(13)
C8 0.0498(15) 0.0581(17) 0.0418(13) 0.0007(10) 0.0109(11) 0.0058(12)
C9 0.0642(19) 0.0537(18) 0.0589(16) 0.0002(12) 0.0096(13) 0.0040(13)
C10 0.083(2) 0.066(2) 0.072(2) 0.0088(14) 0.0081(17) 0.0229(17)
C11 0.065(2) 0.106(3) 0.093(2) 0.013(2) 0.0179(19) 0.026(2)
C12 0.059(2) 0.109(3) 0.116(3) 0.028(2) 0.033(2) 0.010(2)
C13 0.064(2) 0.0647(19) 0.090(2) 0.0190(15) 0.0281(17) 0.0093(15)

_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 C4 1.358(3) . ?
F2 C4 1.363(3) . ?
F3 C5 1.330(4) . ?
F4 C5 1.338(4) . ?
O1 C6 1.205(3) . ?
O2 C7 1.205(3) . ?
N1 N2 1.373(3) . ?
N1 C3 1.469(3) . ?
N2 C1 1.281(3) . ?
N3 C6 1.382(3) . ?
N3 C7 1.386(3) . ?
N3 C8 1.433(3) . ?
C1 C4 1.466(4) . ?
C1 C2 1.523(3) . ?
C2 C6 1.517(3) . ?
C2 C3 1.528(3) . ?
C3 C7 1.503(4) . ?
C4 C5 1.526(4) . ?
C8 C9 1.371(3) . ?
C8 C13 1.374(3) . ?
C9 C10 1.376(4) . ?
C10 C11 1.372(4) . ?
C11 C12 1.366(4) . ?
C12 C13 1.369(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C3 110.8(2) . . ?
C1 N2 N1 110.2(2) . . ?
C6 N3 C7 112.7(2) . . ?
C6 N3 C8 123.56(19) . . ?
C7 N3 C8 123.5(2) . . ?
N2 C1 C4 119.3(2) . . ?
N2 C1 C2 113.6(2) . . ?
C4 C1 C2 127.1(2) . . ?
C6 C2 C1 115.0(2) . . ?
C6 C2 C3 104.2(2) . . ?
C1 C2 C3 100.41(19) . . ?
N1 C3 C7 109.1(2) . . ?
N1 C3 C2 104.7(2) . . ?
C7 C3 C2 105.4(2) . . ?
F1 C4 F2 105.3(2) . . ?
F1 C4 C1 110.5(2) . . ?
F2 C4 C1 109.2(2) . . ?
F1 C4 C5 106.9(2) . . ?
F2 C4 C5 108.6(2) . . ?
C1 C4 C5 115.8(2) . . ?
F3 C5 F4 107.8(3) . . ?
F3 C5 C4 108.8(3) . . ?
F4 C5 C4 108.6(3) . . ?
O1 C6 N3 124.6(2) . . ?
O1 C6 C2 126.7(3) . . ?
N3 C6 C2 108.7(2) . . ?
O2 C7 N3 125.0(3) . . ?
O2 C7 C3 126.4(2) . . ?
N3 C7 C3 108.6(2) . . ?
C9 C8 C13 120.6(2) . . ?
C9 C8 N3 120.3(2) . . ?
C13 C8 N3 119.0(2) . . ?
C8 C9 C10 119.9(3) . . ?
C11 C10 C9 119.5(3) . . ?
C12 C11 C10 120.1(3) . . ?
C11 C12 C13 120.8(3) . . ?
C12 C13 C8 119.0(3) . . ?

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
C3 N1 N2 C1 -4.1(3) . . . . ?
N1 N2 C1 C4 -176.4(2) . . . . ?
N1 N2 C1 C2 5.8(3) . . . . ?
N2 C1 C2 C6 -116.1(3) . . . . ?
C4 C1 C2 C6 66.3(4) . . . . ?
N2 C1 C2 C3 -5.0(3) . . . . ?
C4 C1 C2 C3 177.4(3) . . . . ?
N2 N1 C3 C7 113.1(3) . . . . ?
N2 N1 C3 C2 0.7(3) . . . . ?
C6 C2 C3 N1 121.5(2) . . . . ?
C1 C2 C3 N1 2.2(3) . . . . ?
C6 C2 C3 C7 6.6(3) . . . . ?
C1 C2 C3 C7 -112.8(2) . . . . ?
N2 C1 C4 F1 110.1(3) . . . . ?
C2 C1 C4 F1 -72.3(3) . . . . ?
N2 C1 C4 F2 -134.5(3) . . . . ?
C2 C1 C4 F2 43.0(3) . . . . ?
N2 C1 C4 C5 -11.6(4) . . . . ?
C2 C1 C4 C5 165.9(3) . . . . ?
F1 C4 C5 F3 51.7(3) . . . . ?
F2 C4 C5 F3 -61.5(3) . . . . ?
C1 C4 C5 F3 175.3(3) . . . . ?
F1 C4 C5 F4 168.8(3) . . . . ?
F2 C4 C5 F4 55.6(3) . . . . ?
C1 C4 C5 F4 -67.6(4) . . . . ?
C7 N3 C6 O1 -174.7(2) . . . . ?
C8 N3 C6 O1 -0.5(4) . . . . ?
C7 N3 C6 C2 4.5(3) . . . . ?
C8 N3 C6 C2 178.7(2) . . . . ?
C1 C2 C6 O1 -78.8(3) . . . . ?
C3 C2 C6 O1 172.3(3) . . . . ?
C1 C2 C6 N3 102.0(3) . . . . ?
C3 C2 C6 N3 -6.8(3) . . . . ?
C6 N3 C7 O2 -179.0(2) . . . . ?
C8 N3 C7 O2 6.9(4) . . . . ?
C6 N3 C7 C3 -0.1(3) . . . . ?
C8 N3 C7 C3 -174.2(2) . . . . ?
N1 C3 C7 O2 62.7(3) . . . . ?
C2 C3 C7 O2 174.6(2) . . . . ?
N1 C3 C7 N3 -116.2(2) . . . . ?
C2 C3 C7 N3 -4.3(3) . . . . ?
C6 N3 C8 C9 65.9(3) . . . . ?
C7 N3 C8 C9 -120.6(3) . . . . ?
C6 N3 C8 C13 -114.4(3) . . . . ?
C7 N3 C8 C13 59.1(3) . . . . ?
C13 C8 C9 C10 -0.6(4) . . . . ?
N3 C8 C9 C10 179.1(2) . . . . ?
C8 C9 C10 C11 -0.9(4) . . . . ?
C9 C10 C11 C12 2.4(5) . . . . ?
C10 C11 C12 C13 -2.4(6) . . . . ?
C11 C12 C13 C8 0.8(5) . . . . ?
C9 C8 C13 C12 0.6(4) . . . . ?
N3 C8 C13 C12 -179.0(3) . . . . ?

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
N1 H1N O2 0.77(3) 2.33(3) 3.062(3) 159(3) 7

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.048
####################################################################### 
# 
# 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_t222
_audit_block_doi                 10.5517/cc13s5rt
_database_code_depnum_ccdc_archive 'CCDC 1036136'
_audit_update_record             
;
2014-11-26 deposited with the CCDC.
2015-01-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H10 F4 N2 O2'
_chemical_formula_weight         254.19

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           ?
_symmetry_space_group_name_H-M   ?

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                   9.0310(9)
_cell_length_b                   22.7184(15)
_cell_length_c                   5.5619(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.420(7)
_cell_angle_gamma                90.00
_cell_volume                     1125.75(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             520
_exptl_absorpt_coefficient_mu    0.149
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9708
_exptl_absorpt_correction_T_max  0.9970
_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10246
_diffrn_reflns_av_R_equivalents  0.0613
_diffrn_reflns_av_sigmaI/netI    0.0718
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.91
_diffrn_reflns_theta_max         29.99
_reflns_number_total             3202
_reflns_number_gt                1215
_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)+(0.0822P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3202
_refine_ls_number_parameters     160
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1632
_refine_ls_R_factor_gt           0.0545
_refine_ls_wR_factor_ref         0.1713
_refine_ls_wR_factor_gt          0.1339
_refine_ls_goodness_of_fit_ref   0.825
_refine_ls_restrained_S_all      0.833
_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
F1 F -0.1233(2) 0.61579(8) 0.5609(4) 0.1066(7) Uani 1 1 d . . .
F2 F -0.0065(2) 0.64553(8) 0.9120(3) 0.0954(7) Uani 1 1 d . . .
F3 F 0.2043(3) 0.69709(8) 0.6886(4) 0.1215(8) Uani 1 1 d . . .
F4 F -0.0267(3) 0.72465(8) 0.5583(3) 0.1201(8) Uani 1 1 d . . .
O1 O 0.3670(2) 0.45099(8) 1.1947(3) 0.0724(6) Uani 1 1 d . . .
O2 O 0.3933(2) 0.41546(7) 0.8267(3) 0.0602(5) Uani 1 1 d . . .
N1 N 0.2468(3) 0.50859(9) 0.5960(3) 0.0606(6) Uani 1 1 d . . .
H1N H 0.275(3) 0.4845(10) 0.492(4) 0.054(7) Uiso 1 1 d . . .
N2 N 0.1622(3) 0.55447(9) 0.5142(3) 0.0623(6) Uani 1 1 d . . .
C1 C 0.1143(3) 0.57597(10) 0.7115(4) 0.0534(6) Uani 1 1 d . . .
C2 C 0.1700(3) 0.54349(10) 0.9186(4) 0.0547(6) Uani 1 1 d . . .
H2 H 0.1534 0.5499 1.0772 0.066 Uiso 1 1 calc R . .
C3 C 0.2542(3) 0.50034(9) 0.8377(4) 0.0510(6) Uani 1 1 d . . .
C4 C 0.0158(3) 0.62819(10) 0.6882(4) 0.0629(7) Uani 1 1 d . . .
C5 C 0.0714(4) 0.68045(14) 0.5591(5) 0.0821(9) Uani 1 1 d . . .
H5 H 0.0828 0.6699 0.3922 0.099 Uiso 1 1 calc R . .
C6 C 0.3436(3) 0.45337(10) 0.9761(4) 0.0540(6) Uani 1 1 d . . .
C7 C 0.4813(3) 0.36492(11) 0.9339(4) 0.0619(7) Uani 1 1 d D . .
H7 H 0.5500 0.3773 1.0802 0.074 Uiso 1 1 calc R . .
C8 C 0.3758(4) 0.31824(13) 0.9994(6) 0.0896(10) Uani 1 1 d D . .
H8C H 0.4323 0.2840 1.0595 0.134 Uiso 1 1 calc R . .
H8B H 0.3051 0.3080 0.8574 0.134 Uiso 1 1 calc R . .
H8A H 0.3230 0.3331 1.1231 0.134 Uiso 1 1 calc R . .
C9 C 0.5700(4) 0.34501(14) 0.7400(5) 0.0854(9) Uani 1 1 d D . .
H9C H 0.5022 0.3350 0.5942 0.128 Uiso 1 1 calc R . .
H9B H 0.6290 0.3111 0.7971 0.128 Uiso 1 1 calc R . .
H9A H 0.6351 0.3762 0.7057 0.128 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
F1 0.0660(14) 0.0947(13) 0.1526(17) -0.0124(11) -0.0012(12) 0.0116(10)
F2 0.1393(18) 0.0909(12) 0.0678(10) 0.0064(8) 0.0521(10) 0.0457(12)
F3 0.116(2) 0.0847(14) 0.1613(19) -0.0002(12) 0.0151(15) -0.0181(13)
F4 0.173(2) 0.0838(13) 0.1117(13) 0.0257(10) 0.0470(13) 0.0540(14)
O1 0.1000(16) 0.0771(12) 0.0429(9) 0.0008(8) 0.0204(8) 0.0277(11)
O2 0.0745(13) 0.0579(9) 0.0518(9) -0.0038(7) 0.0217(8) 0.0144(9)
N1 0.0894(18) 0.0556(12) 0.0418(11) -0.0025(9) 0.0260(10) 0.0153(11)
N2 0.0863(17) 0.0623(12) 0.0417(10) 0.0026(8) 0.0209(9) 0.0183(12)
C1 0.0636(17) 0.0536(12) 0.0466(12) -0.0025(9) 0.0196(10) 0.0065(12)
C2 0.0684(18) 0.0580(13) 0.0417(11) -0.0013(9) 0.0208(10) 0.0055(12)
C3 0.0622(17) 0.0533(13) 0.0414(11) -0.0007(9) 0.0201(10) 0.0011(11)
C4 0.073(2) 0.0660(15) 0.0525(13) -0.0018(11) 0.0179(12) 0.0123(14)
C5 0.109(3) 0.0656(17) 0.0751(18) 0.0041(14) 0.0248(17) 0.0239(19)
C6 0.0589(17) 0.0548(13) 0.0514(13) -0.0028(10) 0.0182(10) 0.0047(12)
C7 0.0650(19) 0.0588(14) 0.0646(14) -0.0003(11) 0.0184(12) 0.0126(13)
C8 0.099(3) 0.0702(18) 0.110(2) 0.0156(16) 0.0476(19) 0.0159(18)
C9 0.090(3) 0.086(2) 0.089(2) -0.0073(16) 0.0424(17) 0.0174(19)

_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 C4 1.366(3) . ?
F2 C4 1.351(3) . ?
F3 C5 1.349(4) . ?
F4 C5 1.339(4) . ?
O1 C6 1.201(2) . ?
O2 C6 1.325(3) . ?
O2 C7 1.466(3) . ?
N1 N2 1.328(3) . ?
N1 C3 1.348(3) . ?
N2 C1 1.336(3) . ?
C1 C2 1.391(3) . ?
C1 C4 1.476(3) . ?
C2 C3 1.361(3) . ?
C3 C6 1.476(3) . ?
C4 C5 1.515(4) . ?
C7 C8 1.510(3) . ?
C7 C9 1.514(3) . ?

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
C6 O2 C7 118.06(17) . . ?
N2 N1 C3 112.5(2) . . ?
N1 N2 C1 104.55(17) . . ?
N2 C1 C2 111.4(2) . . ?
N2 C1 C4 119.56(19) . . ?
C2 C1 C4 129.1(2) . . ?
C3 C2 C1 104.74(19) . . ?
N1 C3 C2 106.9(2) . . ?
N1 C3 C6 123.6(2) . . ?
C2 C3 C6 129.5(2) . . ?
F2 C4 F1 105.9(2) . . ?
F2 C4 C1 109.38(18) . . ?
F1 C4 C1 111.7(2) . . ?
F2 C4 C5 108.6(2) . . ?
F1 C4 C5 105.3(2) . . ?
C1 C4 C5 115.4(3) . . ?
F4 C5 F3 108.8(3) . . ?
F4 C5 C4 108.6(3) . . ?
F3 C5 C4 107.6(2) . . ?
O1 C6 O2 125.8(2) . . ?
O1 C6 C3 123.4(2) . . ?
O2 C6 C3 110.83(19) . . ?
O2 C7 C8 109.1(2) . . ?
O2 C7 C9 105.0(2) . . ?
C8 C7 C9 113.0(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N1 N2 C1 0.0(3) . . . . ?
N1 N2 C1 C2 0.3(3) . . . . ?
N1 N2 C1 C4 179.9(2) . . . . ?
N2 C1 C2 C3 -0.5(3) . . . . ?
C4 C1 C2 C3 179.9(3) . . . . ?
N2 N1 C3 C2 -0.3(3) . . . . ?
N2 N1 C3 C6 -178.4(2) . . . . ?
C1 C2 C3 N1 0.4(3) . . . . ?
C1 C2 C3 C6 178.5(2) . . . . ?
N2 C1 C4 F2 -174.0(2) . . . . ?
C2 C1 C4 F2 5.5(4) . . . . ?
N2 C1 C4 F1 69.0(3) . . . . ?
C2 C1 C4 F1 -111.5(3) . . . . ?
N2 C1 C4 C5 -51.2(3) . . . . ?
C2 C1 C4 C5 128.3(3) . . . . ?
F2 C4 C5 F4 -55.0(3) . . . . ?
F1 C4 C5 F4 58.1(3) . . . . ?
C1 C4 C5 F4 -178.2(2) . . . . ?
F2 C4 C5 F3 62.6(3) . . . . ?
F1 C4 C5 F3 175.7(2) . . . . ?
C1 C4 C5 F3 -60.6(3) . . . . ?
C7 O2 C6 O1 1.8(4) . . . . ?
C7 O2 C6 C3 -178.4(2) . . . . ?
N1 C3 C6 O1 169.2(2) . . . . ?
C2 C3 C6 O1 -8.5(4) . . . . ?
N1 C3 C6 O2 -10.5(3) . . . . ?
C2 C3 C6 O2 171.8(2) . . . . ?
C6 O2 C7 C8 80.3(3) . . . . ?
C6 O2 C7 C9 -158.4(2) . . . . ?

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
N1 H1N O1 0.87(2) 2.11(3) 2.944(3) 162(2) 1_554

_diffrn_measured_fraction_theta_max 0.977
_diffrn_reflns_theta_full        29.99
_diffrn_measured_fraction_theta_full 0.977
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.043
####################################################################### 
# 
# 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_tolm226
_audit_block_doi                 10.5517/cc13s5sv
_database_code_depnum_ccdc_archive 'CCDC 1036137'
_audit_update_record             
;
2014-11-26 deposited with the CCDC.
2015-01-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C4 H5 F2 N O2'
_chemical_formula_weight         137.09

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           ?
_symmetry_space_group_name_H-M   ?

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                   9.2697(8)
_cell_length_b                   5.3382(5)
_cell_length_c                   10.8156(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.537(7)
_cell_angle_gamma                90.00
_cell_volume                     531.71(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.713
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             280
_exptl_absorpt_coefficient_mu    0.178
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9653
_exptl_absorpt_correction_T_max  0.9912
_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4460
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_av_sigmaI/netI    0.0390
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.79
_diffrn_reflns_theta_max         29.99
_reflns_number_total             1538
_reflns_number_gt                1080
_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)+(0.0871P)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    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.018(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1538
_refine_ls_number_parameters     103
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0496
_refine_ls_wR_factor_ref         0.1524
_refine_ls_wR_factor_gt          0.1336
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_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
F1 F 0.60317(14) 0.7725(2) 0.88335(9) 0.0656(4) Uani 1 1 d . . .
F2 F 0.54581(10) 0.3770(2) 0.88021(10) 0.0652(4) Uani 1 1 d . . .
O1 O 0.78748(12) 0.26062(19) 0.75560(9) 0.0451(3) Uani 1 1 d . . .
O2 O 0.94401(14) -0.0125(2) 0.84498(11) 0.0538(4) Uani 1 1 d . . .
N1 N 0.86002(16) 0.2865(2) 0.96633(11) 0.0447(4) Uani 1 1 d . . .
H1N H 0.912(2) 0.216(4) 1.0238(19) 0.067(6) Uiso 1 1 d . . .
C1 C 0.86923(16) 0.1707(3) 0.85768(13) 0.0393(3) Uani 1 1 d . . .
C2 C 0.72514(19) 0.5045(3) 0.75899(13) 0.0444(4) Uani 1 1 d . . .
H2B H 0.803(2) 0.629(3) 0.7545(17) 0.057(5) Uiso 1 1 d . . .
H2A H 0.655(2) 0.501(3) 0.6861(18) 0.051(4) Uiso 1 1 d . . .
C3 C 0.65896(16) 0.5385(3) 0.87798(13) 0.0424(4) Uani 1 1 d . . .
C4 C 0.76819(18) 0.4963(3) 0.98938(13) 0.0441(4) Uani 1 1 d . . .
H4B H 0.717(2) 0.461(3) 1.0608(18) 0.057(5) Uiso 1 1 d . . .
H4A H 0.822(2) 0.658(4) 1.0044(17) 0.056(5) Uiso 1 1 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
F1 0.0743(8) 0.0605(7) 0.0614(7) 0.0016(4) 0.0056(5) 0.0308(6)
F2 0.0441(6) 0.0859(9) 0.0673(7) -0.0096(5) 0.0139(4) -0.0137(5)
O1 0.0508(7) 0.0467(6) 0.0374(5) -0.0048(4) 0.0042(4) 0.0043(5)
O2 0.0549(7) 0.0458(6) 0.0609(8) -0.0059(5) 0.0071(5) 0.0120(5)
N1 0.0471(8) 0.0465(7) 0.0387(7) -0.0015(5) -0.0030(5) 0.0094(6)
C1 0.0382(7) 0.0369(7) 0.0429(7) -0.0008(5) 0.0047(5) -0.0002(5)
C2 0.0495(9) 0.0463(8) 0.0371(7) 0.0034(5) 0.0034(6) 0.0062(7)
C3 0.0402(8) 0.0438(8) 0.0433(8) 0.0000(5) 0.0052(5) 0.0059(6)
C4 0.0495(9) 0.0455(8) 0.0371(7) -0.0034(5) 0.0038(6) 0.0085(6)

_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 C3 1.3558(17) . ?
F2 C3 1.3600(18) . ?
O1 C1 1.3539(18) . ?
O1 C2 1.4264(18) . ?
O2 C1 1.2155(17) . ?
N1 C1 1.3391(18) . ?
N1 C4 1.446(2) . ?
C2 C3 1.498(2) . ?
C3 C4 1.500(2) . ?

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 O1 C2 119.56(10) . . ?
C1 N1 C4 127.34(12) . . ?
O2 C1 N1 124.38(14) . . ?
O2 C1 O1 117.81(12) . . ?
N1 C1 O1 117.80(12) . . ?
O1 C2 C3 109.84(12) . . ?
F1 C3 F2 106.54(12) . . ?
F1 C3 C2 110.12(12) . . ?
F2 C3 C2 109.29(13) . . ?
F1 C3 C4 109.25(12) . . ?
F2 C3 C4 110.01(13) . . ?
C2 C3 C4 111.51(13) . . ?
N1 C4 C3 109.55(12) . . ?

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
C4 N1 C1 O2 -176.58(16) . . . . ?
C4 N1 C1 O1 2.0(2) . . . . ?
C2 O1 C1 O2 -165.52(14) . . . . ?
C2 O1 C1 N1 15.8(2) . . . . ?
C1 O1 C2 C3 -44.96(19) . . . . ?
O1 C2 C3 F1 178.26(12) . . . . ?
O1 C2 C3 F2 -65.04(16) . . . . ?
O1 C2 C3 C4 56.80(18) . . . . ?
C1 N1 C4 C3 11.5(2) . . . . ?
F1 C3 C4 N1 -161.97(13) . . . . ?
F2 C3 C4 N1 81.41(16) . . . . ?
C2 C3 C4 N1 -40.02(19) . . . . ?

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
N1 H1N O2 0.83(2) 2.13(2) 2.9598(18) 173.2(19) 3_757

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        29.99
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.056
####################################################################### 
# 
# 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_tolm228
_audit_block_doi                 10.5517/cc13s5tw
_database_code_depnum_ccdc_archive 'CCDC 1036138'
_audit_update_record             
;
2014-11-26 deposited with the CCDC.
2015-01-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H9 N O4'
_chemical_formula_weight         231.20

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           ?
_symmetry_space_group_name_H-M   ?

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                   5.7282(6)
_cell_length_b                   7.9911(8)
_cell_length_c                   23.674(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.336(10)
_cell_angle_gamma                90.00
_cell_volume                     1082.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             480
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9682
_exptl_absorpt_correction_T_max  0.9957
_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            1809
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0534
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.08
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1809
_reflns_number_gt                1292
_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)+(0.1441P)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    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.006(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1809
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1110
_refine_ls_R_factor_gt           0.0829
_refine_ls_wR_factor_ref         0.2286
_refine_ls_wR_factor_gt          0.2092
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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
O1 O 0.5786(5) 0.1505(3) 0.45019(11) 0.0611(9) Uani 1 1 d . . .
O2 O 0.6108(5) 0.2945(4) 0.59185(12) 0.0666(9) Uani 1 1 d . . .
O3 O 0.8495(5) 0.1310(3) 0.54315(12) 0.0607(9) Uani 1 1 d . . .
O4 O -0.0732(5) 0.4413(4) 0.42269(12) 0.0715(10) Uani 1 1 d . . .
N1 N 0.4207(6) 0.1908(4) 0.40569(14) 0.0598(10) Uani 1 1 d . . .
C1 C 0.2731(7) 0.2971(4) 0.42667(15) 0.0431(9) Uani 1 1 d . . .
C2 C 0.3255(7) 0.3299(4) 0.48401(15) 0.0468(10) Uani 1 1 d . . .
H2 H 0.2452 0.3994 0.5080 0.056 Uiso 1 1 calc R . .
C3 C 0.5169(7) 0.2385(4) 0.49648(15) 0.0459(9) Uani 1 1 d . . .
C4 C 0.6617(7) 0.2255(4) 0.54883(17) 0.0494(10) Uani 1 1 d . . .
C5 C 1.0027(8) 0.1145(6) 0.5929(2) 0.0684(13) Uani 1 1 d . . .
H5A H 1.1272 0.0385 0.5852 0.103 Uiso 1 1 calc R . .
H5B H 0.9158 0.0720 0.6236 0.103 Uiso 1 1 calc R . .
H5C H 1.0668 0.2219 0.6029 0.103 Uiso 1 1 calc R . .
C6 C 0.0699(7) 0.3732(4) 0.39423(16) 0.0483(10) Uani 1 1 d . . .
C7 C 0.0406(7) 0.3690(4) 0.33153(15) 0.0461(10) Uani 1 1 d . . .
C8 C 0.1970(8) 0.2943(5) 0.29621(18) 0.0605(11) Uani 1 1 d . . .
H8 H 0.3287 0.2406 0.3116 0.073 Uiso 1 1 calc R . .
C9 C 0.1589(8) 0.2989(6) 0.23852(17) 0.0686(13) Uani 1 1 d . . .
H9 H 0.2642 0.2472 0.2153 0.082 Uiso 1 1 calc R . .
C10 C -0.0323(9) 0.3788(6) 0.2150(2) 0.0697(13) Uani 1 1 d . . .
H10 H -0.0571 0.3814 0.1759 0.084 Uiso 1 1 calc R . .
C11 C -0.1873(9) 0.4551(7) 0.24933(19) 0.0760(14) Uani 1 1 d . . .
H11 H -0.3157 0.5116 0.2334 0.091 Uiso 1 1 calc R . .
C12 C -0.1548(7) 0.4489(5) 0.30699(18) 0.0617(12) Uani 1 1 d . . .
H12 H -0.2636 0.4983 0.3299 0.074 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
O1 0.0670(19) 0.0661(17) 0.0499(17) -0.0091(13) 0.0003(15) 0.0242(16)
O2 0.071(2) 0.0773(19) 0.0513(18) -0.0097(14) 0.0015(15) 0.0194(17)
O3 0.0567(18) 0.0719(18) 0.0536(18) -0.0025(13) 0.0016(15) 0.0168(15)
O4 0.0697(19) 0.091(2) 0.0541(18) -0.0169(16) 0.0070(16) 0.0278(18)
N1 0.068(2) 0.063(2) 0.048(2) -0.0095(15) -0.0016(18) 0.0193(19)
C1 0.049(2) 0.0391(17) 0.042(2) -0.0047(14) 0.0066(16) 0.0055(17)
C2 0.055(2) 0.0402(18) 0.045(2) -0.0020(15) 0.0067(19) 0.0011(18)
C3 0.055(2) 0.0420(18) 0.041(2) -0.0024(15) 0.0056(18) 0.0019(19)
C4 0.050(2) 0.048(2) 0.050(2) 0.0032(16) 0.0083(18) 0.0027(19)
C5 0.058(3) 0.071(3) 0.075(3) 0.006(2) -0.006(2) 0.017(2)
C6 0.052(2) 0.0452(19) 0.048(2) -0.0057(16) 0.003(2) 0.0014(18)
C7 0.050(2) 0.0434(18) 0.045(2) -0.0037(15) 0.0019(18) -0.0019(18)
C8 0.063(3) 0.072(3) 0.046(2) -0.0032(19) 0.004(2) 0.009(2)
C9 0.074(3) 0.088(3) 0.045(3) -0.003(2) 0.007(2) 0.007(3)
C10 0.079(3) 0.082(3) 0.048(2) -0.002(2) 0.000(2) -0.006(3)
C11 0.073(3) 0.097(4) 0.057(3) 0.002(2) -0.013(3) 0.012(3)
C12 0.054(2) 0.077(3) 0.053(3) -0.009(2) -0.005(2) 0.013(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
O1 C3 1.361(4) . ?
O1 N1 1.397(4) . ?
O2 C4 1.204(5) . ?
O3 C4 1.326(5) . ?
O3 C5 1.446(5) . ?
O4 C6 1.211(5) . ?
N1 C1 1.311(5) . ?
C1 C2 1.403(5) . ?
C1 C6 1.497(5) . ?
C2 C3 1.340(5) . ?
C3 C4 1.467(6) . ?
C6 C7 1.487(5) . ?
C7 C8 1.385(5) . ?
C7 C12 1.395(5) . ?
C8 C9 1.375(6) . ?
C9 C10 1.366(6) . ?
C10 C11 1.371(6) . ?
C11 C12 1.371(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
C3 O1 N1 107.9(3) . . ?
C4 O3 C5 115.9(3) . . ?
C1 N1 O1 105.7(3) . . ?
N1 C1 C2 111.8(4) . . ?
N1 C1 C6 124.7(3) . . ?
C2 C1 C6 123.5(3) . . ?
C3 C2 C1 104.6(3) . . ?
C2 C3 O1 109.9(3) . . ?
C2 C3 C4 130.9(3) . . ?
O1 C3 C4 119.2(3) . . ?
O2 C4 O3 124.9(4) . . ?
O2 C4 C3 122.3(4) . . ?
O3 C4 C3 112.8(3) . . ?
O4 C6 C7 120.9(4) . . ?
O4 C6 C1 115.3(3) . . ?
C7 C6 C1 123.8(3) . . ?
C8 C7 C12 118.3(4) . . ?
C8 C7 C6 124.2(4) . . ?
C12 C7 C6 117.5(3) . . ?
C9 C8 C7 120.5(4) . . ?
C10 C9 C8 120.6(4) . . ?
C9 C10 C11 119.6(4) . . ?
C10 C11 C12 120.6(5) . . ?
C11 C12 C7 120.4(4) . . ?

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
C3 O1 N1 C1 -0.6(4) . . . . ?
O1 N1 C1 C2 -0.2(4) . . . . ?
O1 N1 C1 C6 -179.1(3) . . . . ?
N1 C1 C2 C3 0.9(4) . . . . ?
C6 C1 C2 C3 179.9(3) . . . . ?
C1 C2 C3 O1 -1.3(4) . . . . ?
C1 C2 C3 C4 176.8(4) . . . . ?
N1 O1 C3 C2 1.2(4) . . . . ?
N1 O1 C3 C4 -177.1(3) . . . . ?
C5 O3 C4 O2 -1.1(6) . . . . ?
C5 O3 C4 C3 179.1(3) . . . . ?
C2 C3 C4 O2 5.3(7) . . . . ?
O1 C3 C4 O2 -176.7(4) . . . . ?
C2 C3 C4 O3 -174.8(4) . . . . ?
O1 C3 C4 O3 3.1(5) . . . . ?
N1 C1 C6 O4 165.8(4) . . . . ?
C2 C1 C6 O4 -13.1(5) . . . . ?
N1 C1 C6 C7 -14.7(6) . . . . ?
C2 C1 C6 C7 166.5(3) . . . . ?
O4 C6 C7 C8 179.7(4) . . . . ?
C1 C6 C7 C8 0.2(6) . . . . ?
O4 C6 C7 C12 1.2(5) . . . . ?
C1 C6 C7 C12 -178.4(3) . . . . ?
C12 C7 C8 C9 -0.2(6) . . . . ?
C6 C7 C8 C9 -178.7(4) . . . . ?
C7 C8 C9 C10 0.7(7) . . . . ?
C8 C9 C10 C11 0.1(7) . . . . ?
C9 C10 C11 C12 -1.4(7) . . . . ?
C10 C11 C12 C7 1.9(7) . . . . ?
C8 C7 C12 C11 -1.1(6) . . . . ?
C6 C7 C12 C11 177.5(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.947
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.947
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.078
####################################################################### 
# 
# 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_t231
_audit_block_doi                 10.5517/cc13s5vx
_database_code_depnum_ccdc_archive 'CCDC 1036139'
_audit_update_record             
;
2014-11-26 deposited with the CCDC.
2015-01-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H7 N O5'
_chemical_formula_weight         185.14

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           ?
_symmetry_space_group_name_H-M   ?

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                   6.4640(4)
_cell_length_b                   20.721(3)
_cell_length_c                   5.7018(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.017(7)
_cell_angle_gamma                90.00
_cell_volume                     757.99(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.622
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.141
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9590
_exptl_absorpt_correction_T_max  0.9972
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6345
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_sigmaI/netI    0.0327
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         3.18
_diffrn_reflns_theta_max         29.99
_reflns_number_total             2139
_reflns_number_gt                1700
_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)+(0.0486P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2139
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0353
_refine_ls_wR_factor_ref         0.0897
_refine_ls_wR_factor_gt          0.0838
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_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
O1 O 0.22480(12) 0.47073(4) 0.02087(13) 0.02147(18) Uani 1 1 d . . .
O2 O 0.14753(12) 0.34609(4) 0.13555(14) 0.02522(19) Uani 1 1 d . . .
O3 O 0.14379(11) 0.37579(4) 0.51436(12) 0.02053(18) Uani 1 1 d . . .
O4 O 0.37299(12) 0.63937(4) 0.50095(13) 0.02313(19) Uani 1 1 d . . .
O5 O 0.39599(12) 0.73213(4) 0.19324(15) 0.0245(2) Uani 1 1 d . . .
H5O H 0.398(2) 0.7576(8) 0.076(3) 0.047(5) Uiso 1 1 d . . .
N1 N 0.27498(14) 0.53571(4) 0.01279(16) 0.0217(2) Uani 1 1 d . . .
C1 C 0.29179(14) 0.55569(5) 0.23253(18) 0.0174(2) Uani 1 1 d . . .
C2 C 0.25249(14) 0.50595(5) 0.39132(19) 0.0169(2) Uani 1 1 d . . .
H2 H 0.2589(19) 0.5092(6) 0.559(3) 0.027(3) Uiso 1 1 d . . .
C3 C 0.21258(15) 0.45437(5) 0.24902(18) 0.0176(2) Uani 1 1 d . . .
C4 C 0.16413(15) 0.38604(5) 0.28960(18) 0.0179(2) Uani 1 1 d . . .
C5 C 0.11004(18) 0.30868(5) 0.5727(2) 0.0226(2) Uani 1 1 d . . .
H5C H -0.009(2) 0.2926(7) 0.475(2) 0.021(3) Uiso 1 1 d . . .
H5B H 0.231(2) 0.2830(7) 0.546(2) 0.026(3) Uiso 1 1 d . . .
H5A H 0.091(2) 0.3097(7) 0.736(3) 0.031(4) Uiso 1 1 d . . .
C6 C 0.34791(15) 0.62381(5) 0.29439(18) 0.0179(2) Uani 1 1 d . . .
C7 C 0.37002(17) 0.66988(5) 0.0976(2) 0.0214(2) Uani 1 1 d . . .
H7B H 0.488(2) 0.6556(7) 0.019(3) 0.031(4) Uiso 1 1 d . . .
H7A H 0.250(2) 0.6671(7) -0.020(3) 0.037(4) Uiso 1 1 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
O1 0.0323(4) 0.0178(4) 0.0146(4) -0.0010(3) 0.0039(3) -0.0034(3)
O2 0.0369(4) 0.0201(4) 0.0186(4) -0.0045(3) 0.0029(3) -0.0027(3)
O3 0.0292(4) 0.0166(4) 0.0162(4) -0.0008(3) 0.0040(3) -0.0017(3)
O4 0.0323(4) 0.0194(4) 0.0175(4) -0.0013(3) 0.0021(3) -0.0003(3)
O5 0.0355(4) 0.0149(4) 0.0229(4) 0.0025(3) 0.0032(3) -0.0015(3)
N1 0.0295(5) 0.0172(5) 0.0184(5) -0.0002(3) 0.0029(3) -0.0032(3)
C1 0.0178(4) 0.0181(5) 0.0162(5) -0.0003(4) 0.0017(4) 0.0012(4)
C2 0.0188(4) 0.0182(5) 0.0137(5) -0.0001(4) 0.0018(4) 0.0014(3)
C3 0.0191(4) 0.0197(5) 0.0138(5) 0.0002(4) 0.0019(4) 0.0003(4)
C4 0.0183(4) 0.0187(5) 0.0164(5) -0.0013(4) 0.0015(4) -0.0002(4)
C5 0.0307(6) 0.0170(5) 0.0202(6) 0.0012(4) 0.0030(4) -0.0022(4)
C6 0.0177(4) 0.0178(5) 0.0181(5) 0.0001(4) 0.0019(4) 0.0012(3)
C7 0.0280(5) 0.0186(5) 0.0174(5) 0.0006(4) 0.0025(4) -0.0024(4)

_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
O1 C3 1.3560(13) . ?
O1 N1 1.3871(12) . ?
O2 C4 1.2022(13) . ?
O3 C4 1.3213(12) . ?
O3 C5 1.4526(13) . ?
O4 C6 1.2127(12) . ?
O5 C7 1.4025(13) . ?
N1 C1 1.3114(14) . ?
C1 C2 1.4152(15) . ?
C1 C6 1.4890(15) . ?
C2 C3 1.3478(15) . ?
C3 C4 1.4744(15) . ?
C6 C7 1.4934(15) . ?

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
C3 O1 N1 108.42(8) . . ?
C4 O3 C5 114.30(9) . . ?
C1 N1 O1 105.49(8) . . ?
N1 C1 C2 112.39(10) . . ?
N1 C1 C6 121.00(10) . . ?
C2 C1 C6 126.61(10) . . ?
C3 C2 C1 103.22(10) . . ?
C2 C3 O1 110.48(9) . . ?
C2 C3 C4 134.10(10) . . ?
O1 C3 C4 115.41(9) . . ?
O2 C4 O3 125.98(10) . . ?
O2 C4 C3 123.25(10) . . ?
O3 C4 C3 110.77(9) . . ?
O4 C6 C1 118.81(10) . . ?
O4 C6 C7 123.09(10) . . ?
C1 C6 C7 118.09(9) . . ?
O5 C7 C6 108.28(9) . . ?

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
C3 O1 N1 C1 0.28(10) . . . . ?
O1 N1 C1 C2 -0.51(11) . . . . ?
O1 N1 C1 C6 179.14(9) . . . . ?
N1 C1 C2 C3 0.53(11) . . . . ?
C6 C1 C2 C3 -179.08(10) . . . . ?
C1 C2 C3 O1 -0.34(10) . . . . ?
C1 C2 C3 C4 178.30(11) . . . . ?
N1 O1 C3 C2 0.05(10) . . . . ?
N1 O1 C3 C4 -178.86(8) . . . . ?
C5 O3 C4 O2 3.62(14) . . . . ?
C5 O3 C4 C3 -175.98(8) . . . . ?
C2 C3 C4 O2 -174.57(11) . . . . ?
O1 C3 C4 O2 4.01(14) . . . . ?
C2 C3 C4 O3 5.04(16) . . . . ?
O1 C3 C4 O3 -176.38(7) . . . . ?
N1 C1 C6 O4 -176.00(9) . . . . ?
C2 C1 C6 O4 3.59(16) . . . . ?
N1 C1 C6 C7 4.17(14) . . . . ?
C2 C1 C6 C7 -176.24(9) . . . . ?
O4 C6 C7 O5 -7.39(14) . . . . ?
C1 C6 C7 O5 172.43(8) . . . . ?

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
O5 H5O O4 0.854(19) 2.179(18) 2.8764(12) 138.8(16) 4_575
O5 H5O O5 0.854(19) 2.191(19) 2.9455(5) 147.3(16) 4_575

_diffrn_measured_fraction_theta_max 0.971
_diffrn_reflns_theta_full        29.99
_diffrn_measured_fraction_theta_full 0.971
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.047
