# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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 2045907'
loop_
_audit_author_name
_audit_author_address
'Lidija Radovanovic'
;University of Belgrade, Innovation Centre of Faculty of Technology and Metallurgy
Serbia
;
_audit_update_record             
;
2020-11-23 deposited with the CCDC.	2021-02-19 downloaded from the CCDC.
;
_publcif_datablock.id            {1a8eca6a-c032-4efc-aa7b-493123b38e16}

_audit_creation_method           'WinGX routine CIF_UPDATE'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H16 N2 O3'
_chemical_formula_sum            'C15 H16 N2 O3'
_chemical_formula_weight         272.3

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'
_symmetry_space_group_name_hall  '-P 1'

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


_cell_length_a                   6.3079(13)
_cell_length_b                   10.573(2)
_cell_length_c                   11.415(2)
_cell_angle_alpha                67.21(3)
_cell_angle_beta                 78.84(3)
_cell_angle_gamma                76.16(3)
_cell_volume                     677.1(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1638
_cell_measurement_theta_min      3.5060
_cell_measurement_theta_max      29.0260

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.75
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             288
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.93541
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.3280
_diffrn_standards_number         .
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        0
_diffrn_reflns_number            5159
_diffrn_reflns_av_R_equivalents  0.0194
_diffrn_reflns_av_sigmaI/netI    0.0325
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.348
_diffrn_reflns_theta_max         25.34
_reflns_number_total             2484
_reflns_number_gt                1919
_reflns_threshold_expression     'I > 2σ(I)'

_computing_data_collection       CrysAlisPro
_computing_cell_refinement       CrysAlisPro
_computing_data_reduction        CrysAlisPro
_computing_structure_solution    'SIR-2014 (Burla et al., 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

_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)+(0.1081P)²+0.0399P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2484
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0772
_refine_ls_R_factor_gt           0.0606
_refine_ls_wR_factor_ref         0.1746
_refine_ls_wR_factor_gt          0.162
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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
C2 C -0.1892(3) 0.9199(2) 0.95562(19) 0.0409(5) Uani 1 1 d . . .
C4 C 0.0220(3) 0.9239(2) 0.76514(19) 0.0368(5) Uani 1 1 d . . .
C5 C -0.1814(3) 1.0355(2) 0.73441(17) 0.0348(5) Uani 1 1 d . . .
C6 C -0.3152(4) 1.0091(2) 0.6501(2) 0.0446(6) Uani 1 1 d . . .
H6A H -0.221547 1.001559 0.574077 0.054 Uiso 1 1 calc R U .
H6B H -0.365925 0.921244 0.696503 0.054 Uiso 1 1 calc R U .
C7 C -0.5113(4) 1.1251(3) 0.6110(2) 0.0538(6) Uani 1 1 d . . .
H7A H -0.585476 1.108131 0.553016 0.065 Uiso 1 1 calc R U .
H7B H -0.614156 1.124858 0.686179 0.065 Uiso 1 1 calc R U .
C8 C -0.4443(4) 1.2665(3) 0.5464(2) 0.0628(7) Uani 1 1 d . . .
H8A H -0.574353 1.338303 0.527043 0.075 Uiso 1 1 calc R U .
H8B H -0.353745 1.270379 0.466447 0.075 Uiso 1 1 calc R U .
C9 C -0.3174(4) 1.2940(3) 0.6313(3) 0.0631(7) Uani 1 1 d . . .
H9A H -0.412212 1.298314 0.707974 0.076 Uiso 1 1 calc R U .
H9B H -0.271001 1.383445 0.586548 0.076 Uiso 1 1 calc R U .
C10 C -0.1174(4) 1.1805(2) 0.6683(2) 0.0465(6) Uani 1 1 d . . .
H10A H -0.043009 1.198522 0.72557 0.056 Uiso 1 1 calc R U .
H10B H -0.016027 1.182153 0.592301 0.056 Uiso 1 1 calc R U .
C11 C 0.1847(3) 0.7597(2) 0.9629(2) 0.0407(5) Uani 1 1 d . . .
C12 C 0.1335(3) 0.6316(2) 1.07059(18) 0.0381(5) Uani 1 1 d . . .
C13 C -0.0689(4) 0.5912(3) 1.0996(2) 0.0573(7) Uani 1 1 d . . .
H13 H -0.184183 0.646351 1.052332 0.069 Uiso 1 1 calc R U .
C14 C -0.0988(5) 0.4680(3) 1.1997(3) 0.0691(8) Uani 1 1 d . . .
H14 H -0.235202 0.441016 1.220237 0.083 Uiso 1 1 calc R U .
C15 C 0.0704(5) 0.3862(3) 1.2682(2) 0.0626(7) Uani 1 1 d . . .
H15 H 0.047591 0.305232 1.337026 0.075 Uiso 1 1 calc R U .
C16 C 0.2719(5) 0.4223(3) 1.2364(3) 0.0698(8) Uani 1 1 d . . .
H16 H 0.388824 0.363766 1.280589 0.084 Uiso 1 1 calc R U .
C17 C 0.3033(4) 0.5461(3) 1.1384(2) 0.0585(7) Uani 1 1 d . . .
H17 H 0.440799 0.571598 1.118279 0.07 Uiso 1 1 calc R U .
N1 N -0.2949(3) 1.01909(19) 0.86149(15) 0.0431(5) Uani 1 1 d . . .
H1 H -0.419638 1.069212 0.874742 0.052 Uiso 1 1 calc R U .
N3 N 0.0073(3) 0.85879(17) 0.89818(15) 0.0382(5) Uani 1 1 d . . .
O1 O -0.2417(3) 0.88502(18) 1.07007(13) 0.0597(5) Uani 1 1 d . . .
O2 O 0.1661(2) 0.89278(17) 0.69011(14) 0.0513(5) Uani 1 1 d . . .
O3 O 0.3691(3) 0.78057(19) 0.92455(18) 0.0651(6) Uani 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
C2 0.0389(12) 0.0424(12) 0.0314(11) -0.0101(10) -0.0007(9) 0.0030(9)
C4 0.0351(11) 0.0371(11) 0.0353(11) -0.0117(9) 0.0036(9) -0.0098(9)
C5 0.0331(10) 0.0384(11) 0.0276(10) -0.0088(9) 0.0016(8) -0.0058(9)
C6 0.0451(13) 0.0514(13) 0.0396(11) -0.0173(10) -0.0001(10) -0.0147(10)
C7 0.0404(13) 0.0776(18) 0.0461(13) -0.0252(13) -0.0087(10) -0.0076(12)
C8 0.0566(16) 0.0624(17) 0.0507(14) -0.0051(13) -0.0189(12) 0.0075(13)
C9 0.0667(17) 0.0407(14) 0.0711(17) -0.0085(13) -0.0157(14) -0.0035(12)
C10 0.0478(13) 0.0409(12) 0.0465(12) -0.0085(10) -0.0087(10) -0.0097(10)
C11 0.0356(12) 0.0387(12) 0.0432(12) -0.0141(10) -0.0024(9) -0.0008(9)
C12 0.0398(11) 0.0371(11) 0.0357(11) -0.0139(9) -0.0035(9) -0.0030(9)
C13 0.0441(13) 0.0513(14) 0.0600(15) -0.0016(12) -0.0103(11) -0.0060(11)
C14 0.0549(16) 0.0594(16) 0.0702(18) 0.0034(14) -0.0046(14) -0.0163(13)
C15 0.0787(19) 0.0472(14) 0.0470(14) 0.0002(12) -0.0065(13) -0.0139(14)
C16 0.0695(18) 0.0588(17) 0.0633(16) 0.0057(14) -0.0314(14) -0.0072(14)
C17 0.0520(15) 0.0581(15) 0.0583(15) -0.0053(13) -0.0198(12) -0.0128(12)
N1 0.0358(10) 0.0493(11) 0.0289(9) -0.0092(8) 0.0004(7) 0.0090(8)
N3 0.0352(9) 0.0362(9) 0.0308(9) -0.0061(8) 0.0009(7) 0.0023(7)
O1 0.0575(11) 0.0686(11) 0.0261(8) -0.0087(8) 0.0015(7) 0.0188(8)
O2 0.0448(9) 0.0569(10) 0.0411(8) -0.0174(8) 0.0114(7) -0.0022(7)
O3 0.0359(9) 0.0602(11) 0.0759(12) -0.0030(9) -0.0009(8) -0.0071(8)

_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
C2 O1 1.213(2) . ?
C2 N1 1.330(3) . ?
C2 N3 1.419(3) . ?
C4 O2 1.201(2) . ?
C4 N3 1.398(3) . ?
C4 C5 1.514(3) . ?
C5 N1 1.452(2) . ?
C5 C6 1.533(3) . ?
C5 C10 1.538(3) . ?
C6 C7 1.516(3) . ?
C6 H6A 0.97 . ?
C6 H6B 0.97 . ?
C7 C8 1.511(4) . ?
C7 H7A 0.97 . ?
C7 H7B 0.97 . ?
C8 C9 1.515(4) . ?
C8 H8A 0.97 . ?
C8 H8B 0.97 . ?
C9 C10 1.516(3) . ?
C9 H9A 0.97 . ?
C9 H9B 0.97 . ?
C10 H10A 0.97 . ?
C10 H10B 0.97 . ?
C11 O3 1.201(3) . ?
C11 N3 1.434(3) . ?
C11 C12 1.489(3) . ?
C12 C17 1.371(3) . ?
C12 C13 1.382(3) . ?
C13 C14 1.385(3) . ?
C13 H13 0.93 . ?
C14 C15 1.362(4) . ?
C14 H14 0.93 . ?
C15 C16 1.356(4) . ?
C15 H15 0.93 . ?
C16 C17 1.381(3) . ?
C16 H16 0.93 . ?
C17 H17 0.93 . ?
N1 H1 0.86 . ?

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 C2 N1 128.74(19) . . ?
O1 C2 N3 124.12(18) . . ?
N1 C2 N3 107.13(17) . . ?
O2 C4 N3 125.87(19) . . ?
O2 C4 C5 126.94(18) . . ?
N3 C4 C5 107.14(16) . . ?
N1 C5 C4 101.30(15) . . ?
N1 C5 C6 112.62(17) . . ?
C4 C5 C6 111.01(17) . . ?
N1 C5 C10 110.96(18) . . ?
C4 C5 C10 110.24(16) . . ?
C6 C5 C10 110.41(17) . . ?
C7 C6 C5 111.71(19) . . ?
C7 C6 H6A 109.3 . . ?
C5 C6 H6A 109.3 . . ?
C7 C6 H6B 109.3 . . ?
C5 C6 H6B 109.3 . . ?
H6A C6 H6B 107.9 . . ?
C8 C7 C6 111.83(19) . . ?
C8 C7 H7A 109.3 . . ?
C6 C7 H7A 109.3 . . ?
C8 C7 H7B 109.3 . . ?
C6 C7 H7B 109.3 . . ?
H7A C7 H7B 107.9 . . ?
C7 C8 C9 110.93(19) . . ?
C7 C8 H8A 109.5 . . ?
C9 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C9 C8 H8B 109.5 . . ?
H8A C8 H8B 108 . . ?
C8 C9 C10 111.1(2) . . ?
C8 C9 H9A 109.4 . . ?
C10 C9 H9A 109.4 . . ?
C8 C9 H9B 109.4 . . ?
C10 C9 H9B 109.4 . . ?
H9A C9 H9B 108 . . ?
C9 C10 C5 111.41(19) . . ?
C9 C10 H10A 109.3 . . ?
C5 C10 H10A 109.3 . . ?
C9 C10 H10B 109.3 . . ?
C5 C10 H10B 109.3 . . ?
H10A C10 H10B 108 . . ?
O3 C11 N3 118.68(19) . . ?
O3 C11 C12 122.77(19) . . ?
N3 C11 C12 118.46(18) . . ?
C17 C12 C13 119.2(2) . . ?
C17 C12 C11 116.9(2) . . ?
C13 C12 C11 123.77(19) . . ?
C12 C13 C14 119.5(2) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
C15 C14 C13 120.4(2) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C16 C15 C14 120.3(2) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C17 119.9(2) . . ?
C15 C16 H16 120 . . ?
C17 C16 H16 120 . . ?
C12 C17 C16 120.6(2) . . ?
C12 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C2 N1 C5 114.22(17) . . ?
C2 N1 H1 122.9 . . ?
C5 N1 H1 122.9 . . ?
C4 N3 C2 110.20(16) . . ?
C4 N3 C11 122.63(17) . . ?
C2 N3 C11 126.56(16) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.061
####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 2045908'
loop_
_audit_author_name
_audit_author_address
'Lidija Radovanovic'
;University of Belgrade, Innovation Centre of Faculty of Technology and Metallurgy
Serbia
;
_audit_update_record             
;
2020-11-23 deposited with the CCDC.	2021-02-19 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT230_2                   
;
PROBLEM: Hirshfeld Test Diff for    C11      --C12      .        5.4 s.u.
RESPONSE: This value for s.u. is usual for light atom structures such as this one.
;
# Added during the CSD deposition process: Monday 23 November 2020 11:38 AM
# end Validation Reply Form

_publcif_datablock.id            {9b1b73a6-1653-4fba-bb7e-d76a9cdd82ad}

_audit_creation_method           'WinGX routine CIF_UPDATE'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H15 F N2 O3'
_chemical_formula_sum            'C15 H15 F N2 O3'
_chemical_formula_weight         290.29

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'
_symmetry_space_group_name_hall  '-P 1'

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


_cell_length_a                   5.9981(12)
_cell_length_b                   11.148(2)
_cell_length_c                   12.073(2)
_cell_angle_alpha                108.98(3)
_cell_angle_beta                 101.57(3)
_cell_angle_gamma                105.27(3)
_cell_volume                     699.3(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1265
_cell_measurement_theta_min      3.7870
_cell_measurement_theta_max      27.4770

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.72
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             304
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.98839
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.3280
_diffrn_standards_number         .
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        0
_diffrn_reflns_number            4747
_diffrn_reflns_av_R_equivalents  0.0189
_diffrn_reflns_av_sigmaI/netI    0.0371
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.303
_diffrn_reflns_theta_max         25.348
_reflns_number_total             2559
_reflns_number_gt                1812
_reflns_threshold_expression     'I > 2σ(I)'

_computing_data_collection       CrysAlisPro
_computing_cell_refinement       CrysAlisPro
_computing_data_reduction        CrysAlisPro
_computing_structure_solution    'SIR-2014 (Burla et al., 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

_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)+(0.0549P)²+0.0354P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2559
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0733
_refine_ls_R_factor_gt           0.0482
_refine_ls_wR_factor_ref         0.1198
_refine_ls_wR_factor_gt          0.1073
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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
C2 C 0.0035(3) 0.18460(17) 0.59301(15) 0.0409(4) Uani 1 1 d . . .
C4 C -0.1836(4) 0.32441(19) 0.54737(17) 0.0481(5) Uani 1 1 d . . .
C5 C -0.2543(3) 0.19916(17) 0.42938(15) 0.0391(4) Uani 1 1 d . . .
C6 C -0.1692(4) 0.2363(2) 0.33005(17) 0.0577(6) Uani 1 1 d . . .
H6A H 0.006833 0.278256 0.358781 0.069 Uiso 1 1 calc R U .
H6B H -0.236893 0.301479 0.314631 0.069 Uiso 1 1 calc R U .
C7 C -0.2484(4) 0.1107(2) 0.21047(18) 0.0673(6) Uani 1 1 d . . .
H7A H -0.201073 0.137799 0.147467 0.081 Uiso 1 1 calc R U .
H7B H -0.165415 0.050392 0.223862 0.081 Uiso 1 1 calc R U .
C8 C -0.5205(4) 0.0357(2) 0.16567(18) 0.0694(7) Uani 1 1 d . . .
H8A H -0.603633 0.092176 0.143153 0.083 Uiso 1 1 calc R U .
H8B H -0.562641 -0.046352 0.092765 0.083 Uiso 1 1 calc R U .
C9 C -0.6043(4) -0.0008(2) 0.26438(19) 0.0639(6) Uani 1 1 d . . .
H9A H -0.535868 -0.065693 0.279939 0.077 Uiso 1 1 calc R U .
H9B H -0.780227 -0.043284 0.235511 0.077 Uiso 1 1 calc R U .
C10 C -0.5272(4) 0.1236(2) 0.38341(18) 0.0576(6) Uani 1 1 d . . .
H10A H -0.610032 0.18395 0.369852 0.069 Uiso 1 1 calc R U .
H10B H -0.575649 0.096134 0.445974 0.069 Uiso 1 1 calc R U .
C11 C 0.0388(4) 0.39243(19) 0.76958(17) 0.0486(5) Uani 1 1 d . . .
C12 C 0.2756(3) 0.50085(17) 0.82594(15) 0.0395(4) Uani 1 1 d . . .
C13 C 0.4443(4) 0.51574(19) 0.76408(17) 0.0489(5) Uani 1 1 d . . .
H13 H 0.405533 0.456924 0.682324 0.059 Uiso 1 1 calc R U .
C14 C 0.6688(4) 0.6167(2) 0.82231(19) 0.0623(6) Uani 1 1 d . . .
H14 H 0.783736 0.626298 0.781258 0.075 Uiso 1 1 calc R U .
C15 C 0.7198(4) 0.7024(2) 0.9414(2) 0.0649(6) Uani 1 1 d . . .
C16 C 0.5592(4) 0.6917(2) 1.00653(18) 0.0605(6) Uani 1 1 d . . .
H16 H 0.600443 0.751662 1.088108 0.073 Uiso 1 1 calc R U .
C17 C 0.3360(4) 0.59052(19) 0.94855(16) 0.0515(5) Uani 1 1 d . . .
H17 H 0.223587 0.581284 0.991015 0.062 Uiso 1 1 calc R U .
N1 N -0.1216(3) 0.12334(14) 0.47342(12) 0.0437(4) Uani 1 1 d . . .
H1 H -0.123677 0.045926 0.426472 0.052 Uiso 1 1 calc R U .
N3 N -0.0290(3) 0.30886(14) 0.63828(12) 0.0430(4) Uani 1 1 d . . .
O1 O 0.1274(3) 0.14520(13) 0.65628(11) 0.0598(4) Uani 1 1 d . . .
O2 O -0.2514(3) 0.41930(15) 0.56093(13) 0.0797(5) Uani 1 1 d . . .
O3 O -0.1069(3) 0.36695(16) 0.82089(14) 0.0905(6) Uani 1 1 d . . .
F1 F 0.9400(3) 0.80232(16) 0.99879(13) 0.1084(6) Uani 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
C2 0.0483(11) 0.0375(10) 0.0320(10) 0.0073(8) 0.0100(8) 0.0176(9)
C4 0.0630(13) 0.0377(11) 0.0468(11) 0.0146(9) 0.0199(10) 0.0235(10)
C5 0.0445(11) 0.0374(10) 0.0374(10) 0.0141(8) 0.0114(8) 0.0198(9)
C6 0.0717(15) 0.0507(13) 0.0465(12) 0.0217(10) 0.0179(11) 0.0125(11)
C7 0.0839(18) 0.0725(15) 0.0414(12) 0.0223(11) 0.0253(11) 0.0176(13)
C8 0.0794(18) 0.0664(15) 0.0446(12) 0.0149(11) -0.0010(11) 0.0231(13)
C9 0.0443(13) 0.0665(15) 0.0581(13) 0.0170(11) -0.0001(10) 0.0066(11)
C10 0.0478(13) 0.0712(15) 0.0548(12) 0.0240(11) 0.0156(10) 0.0244(11)
C11 0.0638(14) 0.0420(11) 0.0376(10) 0.0077(9) 0.0217(10) 0.0210(10)
C12 0.0542(12) 0.0318(10) 0.0317(9) 0.0094(7) 0.0120(8) 0.0192(9)
C13 0.0586(14) 0.0474(12) 0.0372(10) 0.0103(9) 0.0164(10) 0.0207(10)
C14 0.0583(15) 0.0608(14) 0.0585(14) 0.0181(11) 0.0194(11) 0.0130(12)
C15 0.0616(15) 0.0536(14) 0.0564(14) 0.0137(11) 0.0033(12) 0.0067(12)
C16 0.0803(17) 0.0444(12) 0.0350(11) 0.0029(9) 0.0035(11) 0.0162(12)
C17 0.0718(15) 0.0433(12) 0.0362(10) 0.0093(9) 0.0191(10) 0.0222(11)
N1 0.0564(10) 0.0351(8) 0.0322(8) 0.0043(6) 0.0056(7) 0.0224(8)
N3 0.0551(10) 0.0341(8) 0.0331(8) 0.0047(6) 0.0109(7) 0.0186(8)
O1 0.0786(11) 0.0548(9) 0.0371(7) 0.0065(6) 0.0008(7) 0.0379(8)
O2 0.1245(15) 0.0602(10) 0.0665(10) 0.0189(8) 0.0262(10) 0.0622(11)
O3 0.0897(13) 0.0830(12) 0.0619(10) -0.0005(9) 0.0452(10) -0.0052(10)
F1 0.0780(11) 0.0923(11) 0.0881(10) 0.0095(8) -0.0012(8) -0.0187(9)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C2 O1 1.2211(19) . ?
C2 N1 1.330(2) . ?
C2 N3 1.396(2) . ?
C4 O2 1.205(2) . ?
C4 N3 1.376(2) . ?
C4 C5 1.520(2) . ?
C5 N1 1.452(2) . ?
C5 C10 1.517(3) . ?
C5 C6 1.526(2) . ?
C6 C7 1.526(3) . ?
C6 H6A 0.97 . ?
C6 H6B 0.97 . ?
C7 C8 1.513(3) . ?
C7 H7A 0.97 . ?
C7 H7B 0.97 . ?
C8 C9 1.512(3) . ?
C8 H8A 0.97 . ?
C8 H8B 0.97 . ?
C9 C10 1.517(3) . ?
C9 H9A 0.97 . ?
C9 H9B 0.97 . ?
C10 H10A 0.97 . ?
C10 H10B 0.97 . ?
C11 O3 1.195(2) . ?
C11 C12 1.454(3) . ?
C11 N3 1.459(2) . ?
C12 C13 1.380(2) . ?
C12 C17 1.398(2) . ?
C13 C14 1.372(3) . ?
C13 H13 0.93 . ?
C14 C15 1.360(3) . ?
C14 H14 0.93 . ?
C15 F1 1.350(3) . ?
C15 C16 1.365(3) . ?
C16 C17 1.367(3) . ?
C16 H16 0.93 . ?
C17 H17 0.93 . ?
N1 H1 0.86 . ?

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 C2 N1 128.91(15) . . ?
O1 C2 N3 123.76(15) . . ?
N1 C2 N3 107.33(15) . . ?
O2 C4 N3 125.66(18) . . ?
O2 C4 C5 127.20(19) . . ?
N3 C4 C5 107.13(14) . . ?
N1 C5 C10 111.80(15) . . ?
N1 C5 C4 100.61(14) . . ?
C10 C5 C4 110.49(15) . . ?
N1 C5 C6 111.68(14) . . ?
C10 C5 C6 110.69(16) . . ?
C4 C5 C6 111.20(15) . . ?
C5 C6 C7 110.91(16) . . ?
C5 C6 H6A 109.5 . . ?
C7 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C7 C6 H6B 109.5 . . ?
H6A C6 H6B 108 . . ?
C8 C7 C6 111.80(18) . . ?
C8 C7 H7A 109.3 . . ?
C6 C7 H7A 109.3 . . ?
C8 C7 H7B 109.3 . . ?
C6 C7 H7B 109.3 . . ?
H7A C7 H7B 107.9 . . ?
C9 C8 C7 110.97(16) . . ?
C9 C8 H8A 109.4 . . ?
C7 C8 H8A 109.4 . . ?
C9 C8 H8B 109.4 . . ?
C7 C8 H8B 109.4 . . ?
H8A C8 H8B 108 . . ?
C8 C9 C10 111.35(18) . . ?
C8 C9 H9A 109.4 . . ?
C10 C9 H9A 109.4 . . ?
C8 C9 H9B 109.4 . . ?
C10 C9 H9B 109.4 . . ?
H9A C9 H9B 108 . . ?
C5 C10 C9 111.82(16) . . ?
C5 C10 H10A 109.3 . . ?
C9 C10 H10A 109.3 . . ?
C5 C10 H10B 109.3 . . ?
C9 C10 H10B 109.3 . . ?
H10A C10 H10B 107.9 . . ?
O3 C11 C12 125.79(17) . . ?
O3 C11 N3 117.04(19) . . ?
C12 C11 N3 117.16(16) . . ?
C13 C12 C17 119.11(19) . . ?
C13 C12 C11 122.46(16) . . ?
C17 C12 C11 118.40(17) . . ?
C14 C13 C12 120.47(17) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C15 C14 C13 118.6(2) . . ?
C15 C14 H14 120.7 . . ?
C13 C14 H14 120.7 . . ?
F1 C15 C14 118.7(2) . . ?
F1 C15 C16 118.1(2) . . ?
C14 C15 C16 123.1(2) . . ?
C15 C16 C17 118.19(18) . . ?
C15 C16 H16 120.9 . . ?
C17 C16 H16 120.9 . . ?
C16 C17 C12 120.51(19) . . ?
C16 C17 H17 119.7 . . ?
C12 C17 H17 119.7 . . ?
C2 N1 C5 113.82(14) . . ?
C2 N1 H1 123.1 . . ?
C5 N1 H1 123.1 . . ?
C4 N3 C2 111.07(14) . . ?
C4 N3 C11 123.88(14) . . ?
C2 N3 C11 123.20(14) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.039

# END of CIF
