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

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 1859581'
_audit_update_record             
;
2018-07-31 deposited with the CCDC.
2019-02-04 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 N O3'
_chemical_formula_weight         227.21

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           Triclinic
_symmetry_space_group_name_H-M   'P-1   '

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

_cell_length_a                   6.5610(3)
_cell_length_b                   7.0809(4)
_cell_length_c                   12.0629(6)
_cell_angle_alpha                89.067(4)
_cell_angle_beta                 87.281(3)
_cell_angle_gamma                78.757(3)
_cell_volume                     549.03(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1934
_cell_measurement_theta_min      2.9331
_cell_measurement_theta_max      25.0653

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             242
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   'multi scan'
_exptl_absorpt_correction_T_min  0.6463
_exptl_absorpt_correction_T_max  0.7456
_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            6429
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_av_sigmaI/netI    0.0214
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.93
_diffrn_reflns_theta_max         27.51
_reflns_number_total             2521
_reflns_number_gt                1848
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1086P)²+0.1706P] 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         2521
_refine_ls_number_parameters     158
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0861
_refine_ls_R_factor_gt           0.0683
_refine_ls_wR_factor_ref         0.2180
_refine_ls_wR_factor_gt          0.2015
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.089
_refine_ls_shift/su_max          0.039
_refine_ls_shift/su_mean         0.005

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
O3 O 0.4384(3) 0.7255(2) 0.67424(14) 0.0638(5) Uani 1 1 d . . .
N N 0.6915(3) 0.6204(3) 0.79027(16) 0.0591(5) Uani 1 1 d . . .
C8 C 0.6245(4) 0.6834(3) 0.6114(2) 0.0578(6) Uani 1 1 d U . .
C7 C 0.6381(4) 0.6987(3) 0.5013(2) 0.0565(5) Uani 1 1 d U . .
H7A H 0.7720 0.6606 0.4703 0.068 Uiso 1 1 calc R . .
O2 O 0.9779(3) 0.5656(3) 0.66810(17) 0.0787(6) Uani 1 1 d . . .
C6 C 0.4795(4) 0.7650(3) 0.4203(2) 0.0568(6) Uani 1 1 d U . .
C10 C 0.7943(4) 0.6152(3) 0.6867(2) 0.0579(6) Uani 1 1 d . . .
C1 C 0.2695(4) 0.8115(3) 0.4494(2) 0.0648(7) Uani 1 1 d . . .
H1A H 0.2240 0.7979 0.5228 0.078 Uiso 1 1 calc R . .
C9 C 0.4817(4) 0.6852(3) 0.7824(2) 0.0620(6) Uani 1 1 d . . .
C3 C 0.1930(4) 0.8982(4) 0.2634(2) 0.0705(7) Uani 1 1 d . . .
H3A H 0.0955 0.9468 0.2115 0.085 Uiso 1 1 calc R . .
C5 C 0.5439(4) 0.7813(4) 0.3079(2) 0.0649(7) Uani 1 1 d . . .
H5A H 0.6839 0.7468 0.2859 0.078 Uiso 1 1 calc R . .
O1 O 0.3496(3) 0.7075(3) 0.85538(16) 0.0867(7) Uani 1 1 d . . .
C12 C 0.7946(4) 0.7353(4) 0.9630(2) 0.0653(7) Uani 1 1 d . . .
C4 C 0.3961(5) 0.8497(4) 0.2301(2) 0.0721(7) Uani 1 1 d . . .
H4A H 0.4369 0.8618 0.1558 0.086 Uiso 1 1 calc R . .
C2 C 0.1278(4) 0.8777(4) 0.3708(3) 0.0714(7) Uani 1 1 d . . .
H2A H -0.0132 0.9085 0.3910 0.086 Uiso 1 1 calc R . .
C13 C 0.7943(5) 0.8717(5) 1.0169(2) 0.0754(8) Uani 1 1 d . . .
C11 C 0.7918(5) 0.5679(4) 0.8945(2) 0.0781(8) Uani 1 1 d . . .
H11A H 0.9336 0.5007 0.8788 0.094 Uiso 1 1 calc R . .
H11B H 0.7188 0.4804 0.9355 0.094 Uiso 1 1 calc R . .
H13 H 0.805(6) 0.982(5) 1.059(3) 0.111(12) 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
O3 0.0628(10) 0.0635(10) 0.0635(10) -0.0033(8) -0.0021(8) -0.0080(8)
N 0.0666(12) 0.0530(10) 0.0541(11) -0.0007(8) -0.0054(9) -0.0023(9)
C8 0.0800(16) 0.0373(10) 0.0574(10) -0.0019(9) -0.0019(11) -0.0147(10)
C7 0.0560(12) 0.0507(11) 0.0615(11) 0.0019(10) 0.0024(9) -0.0091(9)
O2 0.0633(12) 0.0795(13) 0.0883(14) -0.0075(10) 0.0037(10) -0.0026(9)
C6 0.0742(15) 0.0376(10) 0.0620(14) 0.0029(9) -0.0109(10) -0.0178(9)
C10 0.0620(14) 0.0421(11) 0.0677(15) -0.0073(10) 0.0085(11) -0.0079(9)
C1 0.0761(17) 0.0559(13) 0.0620(14) -0.0054(11) 0.0125(12) -0.0154(11)
C9 0.0692(15) 0.0566(13) 0.0589(14) -0.0039(10) -0.0025(12) -0.0089(11)
C3 0.0716(16) 0.0675(16) 0.0755(18) 0.0052(13) -0.0185(13) -0.0178(12)
C5 0.0605(14) 0.0661(14) 0.0694(16) 0.0032(12) 0.0043(11) -0.0174(11)
O1 0.0795(13) 0.1066(16) 0.0694(12) -0.0092(11) 0.0162(10) -0.0106(11)
C12 0.0634(15) 0.0796(17) 0.0488(13) 0.0063(12) -0.0062(11) -0.0030(12)
C4 0.0850(19) 0.0800(17) 0.0541(14) 0.0075(12) -0.0038(13) -0.0235(14)
C2 0.0612(15) 0.0640(15) 0.088(2) -0.0023(14) -0.0007(13) -0.0106(12)
C13 0.0777(18) 0.092(2) 0.0547(15) -0.0044(15) -0.0053(13) -0.0126(15)
C11 0.099(2) 0.0670(16) 0.0602(15) 0.0047(12) -0.0184(14) 0.0072(14)

_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
O3 C9 1.363(3) . ?
O3 C8 1.390(3) . ?
N C9 1.371(3) . ?
N C10 1.389(3) . ?
N C11 1.456(3) . ?
C8 C7 1.330(3) . ?
C8 C10 1.474(4) . ?
C7 C6 1.467(3) . ?
O2 C10 1.199(3) . ?
C6 C1 1.382(4) . ?
C6 C5 1.410(4) . ?
C1 C2 1.372(4) . ?
C9 O1 1.196(3) . ?
C3 C4 1.353(4) . ?
C3 C2 1.359(4) . ?
C5 C4 1.395(4) . ?
C12 C13 1.173(4) . ?
C12 C11 1.459(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
C9 O3 C8 107.84(19) . . ?
C9 N C10 111.2(2) . . ?
C9 N C11 123.9(2) . . ?
C10 N C11 125.0(2) . . ?
C7 C8 O3 123.8(2) . . ?
C7 C8 C10 127.7(2) . . ?
O3 C8 C10 108.5(2) . . ?
C8 C7 C6 131.5(2) . . ?
C1 C6 C5 118.7(2) . . ?
C1 C6 C7 122.7(2) . . ?
C5 C6 C7 118.6(2) . . ?
O2 C10 N 126.1(3) . . ?
O2 C10 C8 130.8(2) . . ?
N C10 C8 103.2(2) . . ?
C2 C1 C6 120.4(3) . . ?
O1 C9 O3 122.3(2) . . ?
O1 C9 N 128.3(3) . . ?
O3 C9 N 109.4(2) . . ?
C4 C3 C2 121.7(3) . . ?
C4 C5 C6 119.5(2) . . ?
C13 C12 C11 178.8(3) . . ?
C3 C4 C5 119.5(3) . . ?
C3 C2 C1 120.2(3) . . ?
N C11 C12 112.3(2) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.51
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.709
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.045
####################################################################### 
# 
# 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_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1859582'
_audit_update_record             
;
2018-07-31 deposited with the CCDC.
2019-02-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H12 F3 N O3'
_chemical_formula_weight         347.29

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P-1   '

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

_cell_length_a                   6.7109(7)
_cell_length_b                   9.8190(13)
_cell_length_c                   12.7318(14)
_cell_angle_alpha                75.919(8)
_cell_angle_beta                 82.430(9)
_cell_angle_gamma                80.639(9)
_cell_volume                     799.18(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1285
_cell_measurement_theta_min      3.0050
_cell_measurement_theta_max      22.2173

_exptl_crystal_description       clock
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             356
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_type   'multi scan'
_exptl_absorpt_correction_T_min  0.6124
_exptl_absorpt_correction_T_max  0.7456
_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            6248
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_sigmaI/netI    0.0438
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.16
_diffrn_reflns_theta_max         27.53
_reflns_number_total             3601
_reflns_number_gt                1946
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0950P)²+0.2066P] 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         3601
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1175
_refine_ls_R_factor_gt           0.0621
_refine_ls_wR_factor_ref         0.2018
_refine_ls_wR_factor_gt          0.1651
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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
O3 O 0.0138(3) 0.17420(17) 0.36299(15) 0.0495(5) Uani 1 1 d . . .
O1 O -0.2272(3) 0.4625(2) 0.46723(19) 0.0686(6) Uani 1 1 d . . .
O2 O -0.1973(3) 0.0101(2) 0.42738(17) 0.0627(6) Uani 1 1 d . . .
N N -0.2675(3) 0.2339(2) 0.46527(18) 0.0471(6) Uani 1 1 d . . .
C12 C 0.3551(4) 0.3551(3) 0.2652(2) 0.0442(6) Uani 1 1 d . . .
C8 C 0.0189(4) 0.3119(3) 0.3729(2) 0.0446(6) Uani 1 1 d . . .
C13 C 0.4230(4) 0.2212(3) 0.2462(2) 0.0544(7) Uani 1 1 d . . .
H13A H 0.3472 0.1476 0.2772 0.065 Uiso 1 1 calc R . .
C10 C -0.1685(4) 0.3527(3) 0.4391(2) 0.0486(7) Uani 1 1 d . . .
C15 C 0.7143(4) 0.3037(3) 0.1351(2) 0.0519(7) Uani 1 1 d . . .
C6 C -0.4597(4) 0.1987(3) 0.6488(2) 0.0494(7) Uani 1 1 d . . .
C11 C 0.1658(4) 0.3893(3) 0.3300(2) 0.0488(7) Uani 1 1 d . . .
H11A H 0.1452 0.4799 0.3433 0.059 Uiso 1 1 calc R . .
C14 C 0.6013(4) 0.1955(3) 0.1820(2) 0.0560(7) Uani 1 1 d . . .
H14A H 0.6451 0.1049 0.1705 0.067 Uiso 1 1 calc R . .
C9 C -0.1579(4) 0.1268(3) 0.4209(2) 0.0468(6) Uani 1 1 d . . .
C1 C -0.6427(5) 0.2170(3) 0.7118(3) 0.0668(9) Uani 1 1 d . . .
H1A H -0.7626 0.2463 0.6786 0.080 Uiso 1 1 calc R . .
C17 C 0.4737(5) 0.4613(3) 0.2192(3) 0.0653(9) Uani 1 1 d . . .
H17A H 0.4325 0.5515 0.2319 0.078 Uiso 1 1 calc R . .
F3 F 0.8863(4) 0.3486(3) -0.04014(18) 0.1117(9) Uani 1 1 d . . .
C16 C 0.6523(5) 0.4363(3) 0.1547(3) 0.0714(10) Uani 1 1 d . . .
H16A H 0.7302 0.5090 0.1248 0.086 Uiso 1 1 calc R . .
F2 F 0.9504(4) 0.1452(2) 0.0529(2) 0.1336(11) Uani 1 1 d . . .
C7 C -0.4650(4) 0.2255(3) 0.5279(2) 0.0528(7) Uani 1 1 d . . .
H7A H -0.5249 0.1501 0.5121 0.063 Uiso 1 1 calc R . .
H7B H -0.5526 0.3136 0.5040 0.063 Uiso 1 1 calc R . .
C5 C -0.2835(5) 0.1548(3) 0.7002(3) 0.0639(8) Uani 1 1 d . . .
H5A H -0.1595 0.1414 0.6592 0.077 Uiso 1 1 calc R . .
C18 C 0.9022(5) 0.2777(4) 0.0626(3) 0.0664(9) Uani 1 1 d . . .
F1 F 1.0600(3) 0.3205(4) 0.0873(2) 0.1282(11) Uani 1 1 d . . .
C2 C -0.6479(8) 0.1919(4) 0.8237(3) 0.0912(14) Uani 1 1 d . . .
H2A H -0.7714 0.2029 0.8655 0.109 Uiso 1 1 calc R . .
C3 C -0.4717(11) 0.1509(4) 0.8733(3) 0.1000(16) Uani 1 1 d . . .
H3A H -0.4753 0.1368 0.9484 0.120 Uiso 1 1 calc R . .
C4 C -0.2908(8) 0.1307(4) 0.8123(3) 0.0877(12) Uani 1 1 d . . .
H4A H -0.1717 0.1005 0.8463 0.105 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
O3 0.0466(11) 0.0435(10) 0.0593(12) -0.0190(8) 0.0091(9) -0.0087(8)
O1 0.0576(13) 0.0579(13) 0.0957(17) -0.0399(12) 0.0090(12) -0.0029(10)
O2 0.0613(13) 0.0483(11) 0.0821(15) -0.0241(10) 0.0094(11) -0.0173(9)
N 0.0412(12) 0.0504(13) 0.0510(13) -0.0187(10) 0.0046(10) -0.0065(10)
C12 0.0403(14) 0.0427(14) 0.0520(16) -0.0167(11) 0.0005(12) -0.0074(11)
C8 0.0439(15) 0.0406(14) 0.0513(16) -0.0176(11) -0.0009(12) -0.0038(11)
C13 0.0516(17) 0.0381(14) 0.074(2) -0.0187(13) 0.0085(15) -0.0120(12)
C10 0.0454(15) 0.0468(15) 0.0561(17) -0.0193(13) -0.0012(13) -0.0048(12)
C15 0.0472(16) 0.0529(16) 0.0557(17) -0.0142(13) 0.0016(13) -0.0092(12)
C6 0.0577(17) 0.0361(13) 0.0552(17) -0.0163(12) 0.0081(14) -0.0103(12)
C11 0.0480(16) 0.0429(14) 0.0581(17) -0.0192(12) -0.0005(13) -0.0058(12)
C14 0.0513(17) 0.0458(15) 0.071(2) -0.0226(14) 0.0073(15) -0.0046(12)
C9 0.0420(15) 0.0493(15) 0.0503(16) -0.0154(12) 0.0019(12) -0.0083(12)
C1 0.067(2) 0.0605(19) 0.074(2) -0.0256(16) 0.0218(17) -0.0213(15)
C17 0.0624(19) 0.0405(15) 0.093(2) -0.0244(15) 0.0165(17) -0.0131(13)
F3 0.0989(18) 0.150(2) 0.0697(15) -0.0194(14) 0.0184(13) 0.0019(15)
C16 0.062(2) 0.0520(18) 0.098(3) -0.0205(16) 0.0235(18) -0.0215(15)
F2 0.114(2) 0.0812(16) 0.179(3) -0.0370(16) 0.0760(19) 0.0024(13)
C7 0.0363(15) 0.0644(17) 0.0584(18) -0.0197(14) 0.0020(13) -0.0050(12)
C5 0.076(2) 0.0559(18) 0.061(2) -0.0193(14) -0.0134(17) 0.0021(15)
C18 0.0547(19) 0.067(2) 0.075(2) -0.0204(17) 0.0084(17) -0.0068(15)
F1 0.0519(13) 0.231(3) 0.127(2) -0.090(2) 0.0158(13) -0.0388(16)
C2 0.132(4) 0.074(2) 0.074(3) -0.033(2) 0.042(3) -0.049(3)
C3 0.192(6) 0.061(2) 0.051(2) -0.0124(18) 0.005(3) -0.044(3)
C4 0.139(4) 0.059(2) 0.069(3) -0.0136(17) -0.033(3) -0.006(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
O3 C9 1.369(3) . ?
O3 C8 1.395(3) . ?
O1 C10 1.208(3) . ?
O2 C9 1.199(3) . ?
N C9 1.376(3) . ?
N C10 1.384(3) . ?
N C7 1.458(3) . ?
C12 C17 1.383(4) . ?
C12 C13 1.388(4) . ?
C12 C11 1.459(4) . ?
C8 C11 1.321(4) . ?
C8 C10 1.475(4) . ?
C13 C14 1.381(4) . ?
C15 C16 1.373(4) . ?
C15 C14 1.376(4) . ?
C15 C18 1.487(4) . ?
C6 C5 1.384(4) . ?
C6 C1 1.386(4) . ?
C6 C7 1.501(4) . ?
C1 C2 1.382(5) . ?
C17 C16 1.384(4) . ?
F3 C18 1.333(4) . ?
F2 C18 1.320(4) . ?
C5 C4 1.384(5) . ?
C18 F1 1.301(4) . ?
C2 C3 1.370(6) . ?
C3 C4 1.366(7) . ?

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
C9 O3 C8 108.93(19) . . ?
C9 N C10 110.9(2) . . ?
C9 N C7 124.6(2) . . ?
C10 N C7 124.5(2) . . ?
C17 C12 C13 117.8(3) . . ?
C17 C12 C11 118.7(2) . . ?
C13 C12 C11 123.5(2) . . ?
C11 C8 O3 125.5(2) . . ?
C11 C8 C10 127.4(2) . . ?
O3 C8 C10 107.0(2) . . ?
C14 C13 C12 121.1(2) . . ?
O1 C10 N 125.9(3) . . ?
O1 C10 C8 129.6(2) . . ?
N C10 C8 104.5(2) . . ?
C16 C15 C14 119.9(3) . . ?
C16 C15 C18 119.9(3) . . ?
C14 C15 C18 120.2(3) . . ?
C5 C6 C1 118.7(3) . . ?
C5 C6 C7 123.6(3) . . ?
C1 C6 C7 117.7(3) . . ?
C8 C11 C12 130.2(2) . . ?
C15 C14 C13 120.0(3) . . ?
O2 C9 O3 122.4(2) . . ?
O2 C9 N 128.9(2) . . ?
O3 C9 N 108.6(2) . . ?
C2 C1 C6 120.4(4) . . ?
C12 C17 C16 121.4(3) . . ?
C15 C16 C17 119.8(3) . . ?
N C7 C6 114.6(2) . . ?
C6 C5 C4 120.3(4) . . ?
F1 C18 F2 109.0(3) . . ?
F1 C18 F3 102.9(3) . . ?
F2 C18 F3 102.5(3) . . ?
F1 C18 C15 114.1(3) . . ?
F2 C18 C15 114.5(3) . . ?
F3 C18 C15 112.7(3) . . ?
C3 C2 C1 120.2(4) . . ?
C4 C3 C2 119.9(4) . . ?
C3 C4 C5 120.4(4) . . ?

_diffrn_measured_fraction_theta_max 0.975
_diffrn_reflns_theta_full        27.53
_diffrn_measured_fraction_theta_full 0.975
_refine_diff_density_max         0.578
_refine_diff_density_min         -0.442
_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_1_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1859583'
_audit_update_record             
;
2018-07-31 deposited with the CCDC.
2019-02-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H15 N O4'
_chemical_formula_weight         309.31

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           Orthorhombic
_symmetry_space_group_name_H-M   'Pbca '

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

_cell_length_a                   6.040(2)
_cell_length_b                   19.120(7)
_cell_length_c                   26.355(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3043.5(18)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1710
_cell_measurement_theta_min      2.2662
_cell_measurement_theta_max      23.2948

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1296
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   'multi scan'
_exptl_absorpt_correction_T_min  0.5466
_exptl_absorpt_correction_T_max  0.7456
_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            15282
_diffrn_reflns_av_R_equivalents  0.0684
_diffrn_reflns_av_sigmaI/netI    0.0622
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         2.13
_diffrn_reflns_theta_max         27.99
_reflns_number_total             3560
_reflns_number_gt                2071
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0679P)²+0.1356P] 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         3560
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1022
_refine_ls_R_factor_gt           0.0548
_refine_ls_wR_factor_ref         0.1544
_refine_ls_wR_factor_gt          0.1320
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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
O2 O 0.0225(2) 0.02216(7) 0.38092(5) 0.0504(4) Uani 1 1 d . . .
N N 0.2857(3) -0.05029(8) 0.35339(5) 0.0427(4) Uani 1 1 d . . .
O3 O 0.5345(3) -0.04413(8) 0.42019(6) 0.0631(5) Uani 1 1 d . . .
C12 C 0.3275(4) -0.17210(10) 0.32089(6) 0.0414(5) Uani 1 1 d . . .
O4 O 0.1194(3) -0.37973(8) 0.32649(6) 0.0640(5) Uani 1 1 d . . .
C17 C 0.4479(4) -0.22377(11) 0.34558(7) 0.0475(5) Uani 1 1 d . . .
H17A H 0.5807 -0.2122 0.3613 0.057 Uiso 1 1 calc R . .
C6 C 0.0063(4) 0.10139(10) 0.48207(7) 0.0454(5) Uani 1 1 d . . .
C10 C 0.3619(4) -0.02776(10) 0.40056(7) 0.0440(5) Uani 1 1 d . . .
O1 O -0.0205(3) -0.02576(9) 0.30364(6) 0.0692(5) Uani 1 1 d . . .
C5 C 0.0461(4) 0.13380(11) 0.52926(7) 0.0517(6) Uani 1 1 d . . .
H5A H 0.1765 0.1246 0.5468 0.062 Uiso 1 1 calc R . .
C9 C 0.0868(4) -0.01935(11) 0.34156(8) 0.0493(6) Uani 1 1 d . . .
C8 C 0.1851(4) 0.01905(9) 0.41866(7) 0.0444(5) Uani 1 1 d . . .
C15 C 0.1777(4) -0.31055(10) 0.32356(7) 0.0446(5) Uani 1 1 d . . .
C7 C 0.1755(4) 0.05366(11) 0.46268(7) 0.0477(5) Uani 1 1 d . . .
H7A H 0.2949 0.0462 0.4843 0.057 Uiso 1 1 calc R . .
C16 C 0.3737(4) -0.29210(11) 0.34717(8) 0.0506(6) Uani 1 1 d . . .
H16A H 0.4560 -0.3259 0.3642 0.061 Uiso 1 1 calc R . .
C1 C -0.1920(4) 0.11572(12) 0.45712(8) 0.0551(6) Uani 1 1 d . . .
H1A H -0.2233 0.0939 0.4264 0.066 Uiso 1 1 calc R . .
C11 C 0.4077(4) -0.09670(10) 0.31865(7) 0.0482(5) Uani 1 1 d . . .
H11A H 0.5639 -0.0953 0.3272 0.058 Uiso 1 1 calc R . .
H11B H 0.3916 -0.0795 0.2842 0.058 Uiso 1 1 calc R . .
C14 C 0.0551(4) -0.26001(11) 0.29888(7) 0.0515(6) Uani 1 1 d . . .
H14A H -0.0775 -0.2717 0.2831 0.062 Uiso 1 1 calc R . .
C13 C 0.1317(4) -0.19165(10) 0.29791(7) 0.0499(6) Uani 1 1 d . . .
H13A H 0.0484 -0.1578 0.2812 0.060 Uiso 1 1 calc R . .
C4 C -0.1085(5) 0.17932(12) 0.54954(8) 0.0572(6) Uani 1 1 d . . .
H4A H -0.0827 0.2002 0.5809 0.069 Uiso 1 1 calc R . .
C18 C -0.0759(5) -0.40165(13) 0.30032(11) 0.0735(8) Uani 1 1 d . . .
H18A H -0.0973 -0.4509 0.3053 0.110 Uiso 1 1 calc R . .
H18B H -0.0602 -0.3921 0.2647 0.110 Uiso 1 1 calc R . .
H18C H -0.2015 -0.3767 0.3134 0.110 Uiso 1 1 calc R . .
C2 C -0.3418(4) 0.16204(12) 0.47771(9) 0.0623(7) Uani 1 1 d . . .
H2A H -0.4725 0.1720 0.4605 0.075 Uiso 1 1 calc R . .
C3 C -0.2996(5) 0.19367(13) 0.52345(8) 0.0611(7) Uani 1 1 d . . .
H3A H -0.4015 0.2251 0.5369 0.073 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
O2 0.0516(10) 0.0459(9) 0.0538(8) -0.0088(6) -0.0015(7) 0.0046(7)
N 0.0527(12) 0.0331(8) 0.0423(8) -0.0029(6) 0.0002(8) 0.0029(8)
O3 0.0623(12) 0.0603(11) 0.0667(9) -0.0070(7) -0.0149(9) 0.0104(8)
C12 0.0527(15) 0.0351(10) 0.0362(8) -0.0034(8) 0.0048(9) 0.0061(9)
O4 0.0699(12) 0.0364(8) 0.0858(11) 0.0066(7) -0.0152(9) -0.0023(8)
C17 0.0447(14) 0.0470(13) 0.0507(11) -0.0053(9) -0.0052(10) 0.0072(10)
C6 0.0573(15) 0.0319(10) 0.0470(10) 0.0007(8) 0.0113(10) -0.0033(10)
C10 0.0503(15) 0.0346(11) 0.0470(10) 0.0040(8) -0.0037(10) -0.0050(10)
O1 0.0745(13) 0.0719(12) 0.0610(10) -0.0166(8) -0.0206(9) 0.0166(9)
C5 0.0596(16) 0.0451(12) 0.0504(11) 0.0001(9) 0.0043(11) -0.0011(11)
C9 0.0610(16) 0.0404(12) 0.0465(11) -0.0043(8) -0.0003(11) 0.0067(11)
C8 0.0597(15) 0.0308(10) 0.0427(10) 0.0000(8) 0.0034(10) -0.0027(9)
C15 0.0533(15) 0.0327(10) 0.0478(10) 0.0004(8) 0.0009(10) 0.0049(9)
C7 0.0553(15) 0.0391(11) 0.0487(10) -0.0002(8) 0.0003(10) -0.0022(10)
C16 0.0561(15) 0.0392(12) 0.0565(11) 0.0026(9) -0.0085(11) 0.0121(11)
C1 0.0633(17) 0.0482(13) 0.0537(11) -0.0041(10) 0.0036(12) -0.0072(11)
C11 0.0568(15) 0.0414(12) 0.0463(10) -0.0034(8) 0.0114(10) 0.0012(10)
C14 0.0556(15) 0.0446(13) 0.0544(11) -0.0005(9) -0.0142(10) 0.0038(10)
C13 0.0620(16) 0.0364(11) 0.0513(11) 0.0020(8) -0.0133(11) 0.0085(10)
C4 0.0755(19) 0.0497(13) 0.0463(11) -0.0055(9) 0.0117(12) 0.0005(12)
C18 0.0692(19) 0.0432(14) 0.108(2) -0.0004(13) -0.0122(16) -0.0078(12)
C2 0.0609(18) 0.0564(15) 0.0697(14) -0.0020(11) 0.0046(12) -0.0010(12)
C3 0.0700(19) 0.0495(14) 0.0638(13) -0.0030(11) 0.0159(13) 0.0054(12)

_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
O2 C9 1.362(2) . ?
O2 C8 1.399(2) . ?
N C9 1.375(3) . ?
N C10 1.394(2) . ?
N C11 1.473(2) . ?
O3 C10 1.205(2) . ?
C12 C13 1.380(3) . ?
C12 C17 1.388(3) . ?
C12 C11 1.522(3) . ?
O4 C15 1.371(2) . ?
O4 C18 1.429(3) . ?
C17 C16 1.382(3) . ?
C6 C1 1.393(3) . ?
C6 C5 1.410(3) . ?
C6 C7 1.463(3) . ?
C10 C8 1.473(3) . ?
O1 C9 1.197(2) . ?
C5 C4 1.384(3) . ?
C8 C7 1.337(3) . ?
C15 C14 1.380(3) . ?
C15 C16 1.383(3) . ?
C1 C2 1.378(3) . ?
C14 C13 1.387(3) . ?
C4 C3 1.371(4) . ?
C2 C3 1.373(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
C9 O2 C8 108.44(16) . . ?
C9 N C10 110.98(17) . . ?
C9 N C11 123.76(16) . . ?
C10 N C11 125.10(18) . . ?
C13 C12 C17 117.48(19) . . ?
C13 C12 C11 120.81(18) . . ?
C17 C12 C11 121.7(2) . . ?
C15 O4 C18 117.88(17) . . ?
C16 C17 C12 121.2(2) . . ?
C1 C6 C5 118.4(2) . . ?
C1 C6 C7 123.96(19) . . ?
C5 C6 C7 117.6(2) . . ?
O3 C10 N 126.1(2) . . ?
O3 C10 C8 130.24(19) . . ?
N C10 C8 103.71(18) . . ?
C4 C5 C6 120.1(2) . . ?
O1 C9 O2 122.7(2) . . ?
O1 C9 N 128.17(19) . . ?
O2 C9 N 109.10(17) . . ?
C7 C8 O2 124.44(19) . . ?
C7 C8 C10 127.8(2) . . ?
O2 C8 C10 107.72(15) . . ?
O4 C15 C14 124.4(2) . . ?
O4 C15 C16 116.13(18) . . ?
C14 C15 C16 119.5(2) . . ?
C8 C7 C6 130.0(2) . . ?
C17 C16 C15 120.32(19) . . ?
C2 C1 C6 120.3(2) . . ?
N C11 C12 112.78(16) . . ?
C15 C14 C13 119.3(2) . . ?
C12 C13 C14 122.21(19) . . ?
C3 C4 C5 120.0(2) . . ?
C3 C2 C1 120.5(3) . . ?
C4 C3 C2 120.6(2) . . ?

_diffrn_measured_fraction_theta_max 0.974
_diffrn_reflns_theta_full        28.00
_diffrn_measured_fraction_theta_full 0.974
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.049
