# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_cis3i
_database_code_depnum_ccdc_archive 'CCDC 2057602'
loop_
_audit_author_name
_audit_author_address
'Sergey Belyakov'
;Latvian Institute of Organic Synthesis
Latvia
;
_audit_update_record             
;
2021-01-20 deposited with the CCDC.	2021-02-26 downloaded from the CCDC.
;
_audit_creation_date             2020-04-08

_chemical_formula_moiety         'C13 H14 F N O5'
_chemical_formula_sum            'C13 H14 F N O5'
_chemical_formula_weight         283.258
_chemical_absolute_configuration ad
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.07537 0.05506 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           ' P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y,z+1/2

_symmetry_Int_Tables_number      19
_cell_length_a                   7.40072(18)
_cell_length_b                   9.1371(3)
_cell_length_c                   18.7024(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1264.67(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    150.0(2)
_cell_measurement_reflns_used    2203
_cell_measurement_theta_min      0.9
_cell_measurement_theta_max      75.0

_exptl_absorpt_coefficient_mu    1.065
_exptl_absorpt_correction_T_max  0.92362
_exptl_absorpt_correction_T_min  0.88016
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_crystal_density_diffrn    1.488
_exptl_crystal_F_000             592
_exptl_crystal_description       'Block '
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_Laue_measured_fraction_full 0.9985
_diffrn_reflns_Laue_measured_fraction_max 0.9793
_diffrn_reflns_point_group_measured_fraction_full 0.9956
_diffrn_reflns_point_group_measured_fraction_max 0.9642
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_ambient_temperature      150.0(2)
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.943
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10385
_diffrn_reflns_av_R_equivalents  0.0687
_diffrn_reflns_av_sigmaI/netI    0.0347
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         4.73
_diffrn_reflns_theta_max         79.0
_reflns_number_total             2629
_reflns_number_gt                2536
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2008)'
_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)+(0.0076P)²+0.6861P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0032(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(19)
_refine_ls_number_reflns         2629
_refine_ls_number_parameters     207
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0371
_refine_ls_wR_factor_ref         0.0825
_refine_ls_wR_factor_gt          0.0779
_refine_ls_goodness_of_fit_ref   1.202
_refine_ls_restrained_S_all      1.202
_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 0.5386(2) 0.43951(18) 0.26268(7) 0.0343(4) Uani 1 1 d . . .
N2 N 0.5500(2) 0.5573(2) 0.20821(8) 0.0280(4) Uani 1 1 d . . .
C3 C 0.7117(3) 0.6147(2) 0.20860(10) 0.0246(4) Uani 1 1 d . . .
C4 C 0.8296(2) 0.5470(2) 0.26477(9) 0.0250(4) Uani 1 1 d . . .
H4 H 0.9158 0.4784 0.2409 0.030 Uiso 1 1 calc R . .
C5 C 0.6905(3) 0.4559(3) 0.30701(10) 0.0302(4) Uani 1 1 d . . .
H5 H 0.729(3) 0.354(3) 0.3232(13) 0.035(6) Uiso 1 1 d . . .
O6 O 0.41205(19) 0.5721(2) 0.17313(8) 0.0387(4) Uani 1 1 d . . .
C7 C 0.7774(3) 0.7185(2) 0.15409(10) 0.0262(4) Uani 1 1 d . . .
O8 O 0.93552(19) 0.74981(18) 0.15155(7) 0.0350(4) Uani 1 1 d . . .
O9 O 0.64893(17) 0.76811(16) 0.11059(6) 0.0276(3) Uani 1 1 d . . .
C10 C 0.7095(3) 0.8622(2) 0.05200(11) 0.0298(4) Uani 1 1 d . . .
H10A H 0.815(3) 0.914(3) 0.0670(12) 0.029(6) Uiso 1 1 d . . .
H10B H 0.606(3) 0.932(3) 0.0445(13) 0.040(7) Uiso 1 1 d . . .
C11 C 0.7488(3) 0.7723(3) -0.01352(10) 0.0332(5) Uani 1 1 d . . .
H11A H 0.8037 0.8347 -0.0502 0.050 Uiso 1 1 calc R . .
H11B H 0.6360 0.7307 -0.0319 0.050 Uiso 1 1 calc R . .
H11C H 0.8324 0.6931 -0.0011 0.050 Uiso 1 1 calc R . .
C12 C 0.9369(3) 0.6541(2) 0.30921(9) 0.0243(4) Uani 1 1 d . . .
C13 C 0.8590(3) 0.7792(2) 0.33800(9) 0.0263(4) Uani 1 1 d . . .
H13 H 0.7365 0.8014 0.3274 0.032 Uiso 1 1 calc R . .
C14 C 0.9561(3) 0.8717(2) 0.38173(10) 0.0291(4) Uani 1 1 d . . .
H14 H 0.9009 0.9572 0.4007 0.035 Uiso 1 1 calc R . .
C15 C 1.1355(3) 0.8394(2) 0.39811(10) 0.0304(4) Uani 1 1 d . . .
C16 C 1.2183(3) 0.7192(2) 0.36717(11) 0.0322(5) Uani 1 1 d . . .
H16 H 1.3423 0.6994 0.3761 0.039 Uiso 1 1 calc R . .
C17 C 1.1180(3) 0.6277(2) 0.32281(11) 0.0289(4) Uani 1 1 d . . .
H17 H 1.1749 0.5454 0.3014 0.035 Uiso 1 1 calc R . .
O18 O 1.2190(2) 0.93469(19) 0.44396(9) 0.0445(4) Uani 1 1 d . . .
C19 C 1.3896(4) 0.8910(4) 0.47240(15) 0.0513(7) Uani 1 1 d . . .
H19A H 1.490(5) 0.900(4) 0.4335(18) 0.077(11) Uiso 1 1 d . . .
H19B H 1.386(4) 0.790(4) 0.4917(16) 0.063(9) Uiso 1 1 d . . .
H19C H 1.410(5) 0.958(4) 0.5131(17) 0.073(10) Uiso 1 1 d . . .
F20 F 0.63374(17) 0.53068(15) 0.36744(6) 0.0392(3) Uani 1 1 d . . .


_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 C5 1.405(2) . ?
O1 N2 1.484(2) . ?
N2 O6 1.221(2) . ?
N2 C3 1.306(2) . ?
C3 C7 1.475(3) . ?
C3 C4 1.499(3) . ?
C4 C12 1.510(3) . ?
C4 C5 1.541(3) . ?
C4 H4 1.0000 . ?
C5 F20 1.386(2) . ?
C5 H5 1.02(2) . ?
C7 O8 1.205(2) . ?
C7 O9 1.331(2) . ?
O9 C10 1.463(2) . ?
C10 C11 1.504(3) . ?
C10 H10A 0.95(2) . ?
C10 H10B 1.00(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C17 1.386(3) . ?
C12 C13 1.388(3) . ?
C13 C14 1.378(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.394(3) . ?
C14 H14 0.9500 . ?
C15 O18 1.369(2) . ?
C15 C16 1.385(3) . ?
C16 C17 1.392(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
O18 C19 1.427(3) . ?
C19 H19A 1.04(3) . ?
C19 H19B 0.99(3) . ?
C19 H19C 0.99(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
C5 O1 N2 106.40(14) . . ?
O6 N2 C3 136.43(18) . . ?
O6 N2 O1 113.68(15) . . ?
C3 N2 O1 109.80(15) . . ?
N2 C3 C7 123.80(17) . . ?
N2 C3 C4 111.81(17) . . ?
C7 C3 C4 123.89(16) . . ?
C3 C4 C12 115.12(17) . . ?
C3 C4 C5 101.15(15) . . ?
C12 C4 C5 114.77(15) . . ?
C3 C4 H4 108.5 . . ?
C12 C4 H4 108.5 . . ?
C5 C4 H4 108.5 . . ?
F20 C5 O1 106.93(16) . . ?
F20 C5 C4 110.76(17) . . ?
O1 C5 C4 106.82(15) . . ?
F20 C5 H5 106.9(14) . . ?
O1 C5 H5 107.5(14) . . ?
C4 C5 H5 117.4(14) . . ?
O8 C7 O9 126.07(19) . . ?
O8 C7 C3 119.99(18) . . ?
O9 C7 C3 113.93(16) . . ?
C7 O9 C10 116.03(15) . . ?
O9 C10 C11 110.40(17) . . ?
O9 C10 H10A 108.7(14) . . ?
C11 C10 H10A 110.4(14) . . ?
O9 C10 H10B 104.0(14) . . ?
C11 C10 H10B 112.3(14) . . ?
H10A C10 H10B 111(2) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C17 C12 C13 118.29(19) . . ?
C17 C12 C4 119.80(18) . . ?
C13 C12 C4 121.91(17) . . ?
C14 C13 C12 121.22(18) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C13 C14 C15 119.8(2) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
O18 C15 C16 124.48(19) . . ?
O18 C15 C14 115.7(2) . . ?
C16 C15 C14 119.84(19) . . ?
C15 C16 C17 119.30(19) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 H16 120.4 . . ?
C12 C17 C16 121.4(2) . . ?
C12 C17 H17 119.3 . . ?
C16 C17 H17 119.3 . . ?
C15 O18 C19 117.1(2) . . ?
O18 C19 H19A 110.5(18) . . ?
O18 C19 H19B 111.8(19) . . ?
H19A C19 H19B 110(3) . . ?
O18 C19 H19C 104(2) . . ?
H19A C19 H19C 112(3) . . ?
H19B C19 H19C 108(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
C5 O1 N2 O6 -168.54(18) . . . . ?
C5 O1 N2 C3 14.3(2) . . . . ?
O6 N2 C3 C7 -5.9(4) . . . . ?
O1 N2 C3 C7 170.37(17) . . . . ?
O6 N2 C3 C4 -178.1(2) . . . . ?
O1 N2 C3 C4 -1.8(2) . . . . ?
N2 C3 C4 C12 -134.31(17) . . . . ?
C7 C3 C4 C12 53.5(2) . . . . ?
N2 C3 C4 C5 -10.0(2) . . . . ?
C7 C3 C4 C5 177.86(19) . . . . ?
N2 O1 C5 F20 98.60(17) . . . . ?
N2 O1 C5 C4 -20.0(2) . . . . ?
C3 C4 C5 F20 -97.71(17) . . . . ?
C12 C4 C5 F20 26.9(2) . . . . ?
C3 C4 C5 O1 18.4(2) . . . . ?
C12 C4 C5 O1 142.96(17) . . . . ?
N2 C3 C7 O8 -168.8(2) . . . . ?
C4 C3 C7 O8 2.5(3) . . . . ?
N2 C3 C7 O9 10.4(3) . . . . ?
C4 C3 C7 O9 -178.34(17) . . . . ?
O8 C7 O9 C10 3.9(3) . . . . ?
C3 C7 O9 C10 -175.25(16) . . . . ?
C7 O9 C10 C11 91.4(2) . . . . ?
C3 C4 C12 C17 -134.70(18) . . . . ?
C5 C4 C12 C17 108.5(2) . . . . ?
C3 C4 C12 C13 46.0(2) . . . . ?
C5 C4 C12 C13 -70.8(2) . . . . ?
C17 C12 C13 C14 -2.9(3) . . . . ?
C4 C12 C13 C14 176.35(17) . . . . ?
C12 C13 C14 C15 -0.5(3) . . . . ?
C13 C14 C15 O18 -177.74(18) . . . . ?
C13 C14 C15 C16 3.7(3) . . . . ?
O18 C15 C16 C17 178.25(19) . . . . ?
C14 C15 C16 C17 -3.3(3) . . . . ?
C13 C12 C17 C16 3.3(3) . . . . ?
C4 C12 C17 C16 -175.99(18) . . . . ?
C15 C16 C17 C12 -0.2(3) . . . . ?
C16 C15 O18 C19 -12.9(3) . . . . ?
C14 C15 O18 C19 168.5(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.98
_diffrn_reflns_theta_full        79.0
_diffrn_measured_fraction_theta_full 0.98
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.045

# 
# h,k,l, Fc-squared, Fo-squared, sigma(Fo-squared) and status flag 
# 
_shelx_title                     ' AS639II in P212121 #19'
_shelx_refln_list_code           4
_shelx_F_calc_maximum            96.77
_reflns_d_resolution_high        0.7853

_shelx_F_squared_multiplier      1.000
####################################################################### 
# 
# 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_as649if
_database_code_depnum_ccdc_archive 'CCDC 2057603'
loop_
_audit_author_name
_audit_author_address
'Sergey Belyakov'
;Latvian Institute of Organic Synthesis
Latvia
;
_audit_update_record             
;
2021-01-20 deposited with the CCDC.	2021-02-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H11 F N2 O6'
_chemical_formula_sum            'C12 H11 F N2 O6'
_chemical_formula_weight         298.23

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

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                   6.781(3)
_cell_length_b                   22.970(9)
_cell_length_c                   8.2131(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.101(19)
_cell_angle_gamma                90.00
_cell_volume                     1279.0(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    170.0(2)
_cell_measurement_reflns_used    1204
_cell_measurement_theta_min      0.9
_cell_measurement_theta_max      75.0

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616
_exptl_absorpt_coefficient_mu    1.174
_exptl_absorpt_correction_T_max  0.97802
_exptl_absorpt_correction_T_min  0.81069
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      170.0(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6623
_diffrn_reflns_av_R_equivalents  0.0634
_diffrn_reflns_av_sigmaI/netI    0.0568
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_theta_min         6.63
_diffrn_reflns_theta_max         77.56
_reflns_number_total             2223
_reflns_number_gt                1869
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_refinement  'SHELXL (Sheldrick, 2008)'
_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. 
;

# start Validation Reply Form
_vrf_PLAT911_as649if             
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        411 Report 
RESPONSE: Number of observed reflections is enough for refinement 
(N ~ 10*Npar, where Npar is number of refined parameters). 
;
# end Validation Reply Form


_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)+(0.1038P)²+0.9850P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2223
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0883
_refine_ls_R_factor_gt           0.0746
_refine_ls_wR_factor_ref         0.2043
_refine_ls_wR_factor_gt          0.1915
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.002

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
F21 F 0.5785(4) 0.52349(9) 0.6698(2) 0.0494(6) Uani 1 1 d . . .
O9 O 1.0375(3) 0.57316(9) 0.1902(2) 0.0311(5) Uani 1 1 d . . .
O8 O 0.7256(3) 0.60199(10) 0.1341(2) 0.0359(5) Uani 1 1 d . . .
O6 O 1.1218(4) 0.56100(12) 0.5219(3) 0.0443(6) Uani 1 1 d . . .
O1 O 0.8555(4) 0.57777(11) 0.6784(2) 0.0432(6) Uani 1 1 d . . .
N18 N 0.1529(5) 0.75070(13) 0.2738(4) 0.0441(7) Uani 1 1 d . . .
N2 N 0.9458(4) 0.57325(11) 0.5175(3) 0.0343(6) Uani 1 1 d . . .
O19 O 0.1166(6) 0.80218(13) 0.2546(4) 0.0657(9) Uani 1 1 d . . .
O20 O 0.0480(5) 0.71183(14) 0.2199(4) 0.0667(8) Uani 1 1 d . . .
C7 C 0.8539(4) 0.58774(12) 0.2286(3) 0.0281(6) Uani 1 1 d . . .
C13 C 0.3846(4) 0.67693(13) 0.3773(3) 0.0320(6) Uani 1 1 d . . .
H13 H 0.3015 0.6484 0.3344 0.038 Uiso 1 1 calc R . .
C14 C 0.3359(5) 0.73498(13) 0.3638(3) 0.0342(7) Uani 1 1 d . . .
C3 C 0.8157(4) 0.58533(12) 0.4044(3) 0.0293(6) Uani 1 1 d . . .
C12 C 0.5596(4) 0.66193(13) 0.4561(3) 0.0305(6) Uani 1 1 d . . .
C10 C 1.0765(5) 0.57696(14) 0.0164(3) 0.0353(7) Uani 1 1 d . . .
H10A H 1.0646 0.6170 -0.0201 0.042 Uiso 1 1 calc R . .
H10B H 0.9821 0.5535 -0.0448 0.042 Uiso 1 1 calc R . .
C15 C 0.4525(5) 0.77892(13) 0.4281(4) 0.0371(7) Uani 1 1 d . . .
H15 H 0.4150 0.8177 0.4184 0.045 Uiso 1 1 calc R . .
C4 C 0.6171(4) 0.59857(13) 0.4731(3) 0.0319(6) Uani 1 1 d . . .
H4 H 0.5167 0.5740 0.4202 0.038 Uiso 1 1 calc R . .
C17 C 0.6818(5) 0.70582(14) 0.5202(4) 0.0371(7) Uani 1 1 d . . .
H17 H 0.8006 0.6960 0.5717 0.045 Uiso 1 1 calc R . .
C16 C 0.6272(5) 0.76350(14) 0.5075(4) 0.0414(7) Uani 1 1 d . . .
H16 H 0.7080 0.7922 0.5525 0.050 Uiso 1 1 calc R . .
C11 C 1.2814(5) 0.55515(17) -0.0102(4) 0.0448(8) Uani 1 1 d . . .
H11A H 1.3088 0.5560 -0.1244 0.067 Uiso 1 1 calc R . .
H11B H 1.2928 0.5159 0.0294 0.067 Uiso 1 1 calc R . .
H11C H 1.3741 0.5796 0.0475 0.067 Uiso 1 1 calc R . .
C5 C 0.6511(5) 0.57866(14) 0.6496(4) 0.0387(7) Uani 1 1 d . . .
H5 H 0.5878 0.6057 0.7248 0.046 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F21 C5 1.371(4) . ?
O9 C7 1.333(4) . ?
O9 C10 1.459(3) . ?
O8 C7 1.200(4) . ?
O6 N2 1.226(4) . ?
O1 C5 1.402(5) . ?
O1 N2 1.471(3) . ?
N18 O19 1.217(4) . ?
N18 O20 1.219(5) . ?
N18 C14 1.477(5) . ?
N2 C3 1.298(4) . ?
C7 C3 1.473(3) . ?
C13 C14 1.378(4) . ?
C13 C12 1.384(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.380(5) . ?
C3 C4 1.501(4) . ?
C12 C17 1.401(4) . ?
C12 C4 1.512(4) . ?
C10 C11 1.498(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C15 C16 1.387(5) . ?
C15 H15 0.9300 . ?
C4 C5 1.534(4) . ?
C4 H4 0.9800 . ?
C17 C16 1.379(5) . ?
C17 H17 0.9300 . ?
C16 H16 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C5 H5 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O9 C10 113.8(2) . . ?
C5 O1 N2 106.1(2) . . ?
O19 N18 O20 123.3(3) . . ?
O19 N18 C14 117.9(3) . . ?
O20 N18 C14 118.8(3) . . ?
O6 N2 C3 135.9(2) . . ?
O6 N2 O1 114.3(2) . . ?
C3 N2 O1 109.8(2) . . ?
O8 C7 O9 125.8(2) . . ?
O8 C7 C3 120.3(3) . . ?
O9 C7 C3 113.9(2) . . ?
C14 C13 C12 118.7(3) . . ?
C14 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?
C13 C14 C15 122.8(3) . . ?
C13 C14 N18 118.3(3) . . ?
C15 C14 N18 118.8(3) . . ?
N2 C3 C7 125.4(3) . . ?
N2 C3 C4 112.1(2) . . ?
C7 C3 C4 122.5(3) . . ?
C13 C12 C17 119.5(3) . . ?
C13 C12 C4 120.0(3) . . ?
C17 C12 C4 120.5(3) . . ?
O9 C10 C11 108.0(2) . . ?
O9 C10 H10A 110.1 . . ?
C11 C10 H10A 110.1 . . ?
O9 C10 H10B 110.1 . . ?
C11 C10 H10B 110.1 . . ?
H10A C10 H10B 108.4 . . ?
C14 C15 C16 118.1(3) . . ?
C14 C15 H15 121.0 . . ?
C16 C15 H15 121.0 . . ?
C3 C4 C12 113.1(2) . . ?
C3 C4 C5 100.1(2) . . ?
C12 C4 C5 114.1(2) . . ?
C3 C4 H4 109.7 . . ?
C12 C4 H4 109.7 . . ?
C5 C4 H4 109.7 . . ?
C16 C17 C12 120.5(3) . . ?
C16 C17 H17 119.8 . . ?
C12 C17 H17 119.8 . . ?
C17 C16 C15 120.4(3) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
F21 C5 O1 108.8(3) . . ?
F21 C5 C4 110.0(3) . . ?
O1 C5 C4 107.1(2) . . ?
F21 C5 H5 110.3 . . ?
O1 C5 H5 110.3 . . ?
C4 C5 H5 110.3 . . ?

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
C5 O1 N2 O6 -167.0(3) . . . . ?
C5 O1 N2 C3 15.0(3) . . . . ?
C10 O9 C7 O8 1.3(4) . . . . ?
C10 O9 C7 C3 -178.6(2) . . . . ?
C12 C13 C14 C15 -1.2(4) . . . . ?
C12 C13 C14 N18 177.6(3) . . . . ?
O19 N18 C14 C13 -176.0(3) . . . . ?
O20 N18 C14 C13 2.6(5) . . . . ?
O19 N18 C14 C15 2.8(4) . . . . ?
O20 N18 C14 C15 -178.5(3) . . . . ?
O6 N2 C3 C7 -0.2(6) . . . . ?
O1 N2 C3 C7 177.3(2) . . . . ?
O6 N2 C3 C4 -178.7(3) . . . . ?
O1 N2 C3 C4 -1.2(3) . . . . ?
O8 C7 C3 N2 -176.5(3) . . . . ?
O9 C7 C3 N2 3.3(4) . . . . ?
O8 C7 C3 C4 1.8(4) . . . . ?
O9 C7 C3 C4 -178.4(2) . . . . ?
C14 C13 C12 C17 0.2(4) . . . . ?
C14 C13 C12 C4 179.9(2) . . . . ?
C7 O9 C10 C11 -175.7(3) . . . . ?
C13 C14 C15 C16 0.9(4) . . . . ?
N18 C14 C15 C16 -177.9(3) . . . . ?
N2 C3 C4 C12 110.2(3) . . . . ?
C7 C3 C4 C12 -68.3(3) . . . . ?
N2 C3 C4 C5 -11.5(3) . . . . ?
C7 C3 C4 C5 170.0(3) . . . . ?
C13 C12 C4 C3 124.0(3) . . . . ?
C17 C12 C4 C3 -56.2(3) . . . . ?
C13 C12 C4 C5 -122.4(3) . . . . ?
C17 C12 C4 C5 57.3(4) . . . . ?
C13 C12 C17 C16 1.1(4) . . . . ?
C4 C12 C17 C16 -178.7(3) . . . . ?
C12 C17 C16 C15 -1.4(5) . . . . ?
C14 C15 C16 C17 0.4(5) . . . . ?
N2 O1 C5 F21 97.0(2) . . . . ?
N2 O1 C5 C4 -21.9(3) . . . . ?
C3 C4 C5 F21 -97.8(3) . . . . ?
C12 C4 C5 F21 141.2(3) . . . . ?
C3 C4 C5 O1 20.3(3) . . . . ?
C12 C4 C5 O1 -100.7(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.82
_diffrn_reflns_theta_full        75.0
_diffrn_measured_fraction_theta_full 0.97
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.057

# 
# h,k,l, Fc-squared, Fo-squared, sigma(Fo-squared) and status flag 
# 
_shelx_title                     ' as649if_a.res in P2(1)/c'
_shelx_refln_list_code           4
_shelx_F_calc_maximum            104.72
_reflns_d_resolution_high        0.7894

_shelx_F_squared_multiplier      1.000
