# 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_exp_767
_database_code_depnum_ccdc_archive 'CCDC 2107621'
loop_
_audit_author_name
_audit_author_address
'Pavel A. Slepukhin'
;Postovsky Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2021-09-04 deposited with the CCDC.	2021-10-28 downloaded from the CCDC.
;
_audit_creation_date             2020-06-04
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_chemical_formula_moiety         'C12 H17 F3 N2 O2'
_chemical_formula_sum            'C12 H17 F3 N2 O2'
_chemical_formula_weight         278.276
_chemical_absolute_configuration unk
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 . . 0.49300 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)' .
C . . 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)' .
F . . 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)' .
O . . 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)' .
N . . 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)' .

_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                   5.5102(5)
_cell_length_b                   9.0870(9)
_cell_length_c                   25.588(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1281.2(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1442
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      28.9280
_cell_measurement_theta_min      3.9070
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.24158
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.38a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_description       block
_exptl_crystal_F_000             584.427
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.19
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_unetI/netI     0.0434
_diffrn_reflns_Laue_measured_fraction_full 0.9860
_diffrn_reflns_Laue_measured_fraction_max 0.8789
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            5041
_diffrn_reflns_point_group_measured_fraction_full 0.9860
_diffrn_reflns_point_group_measured_fraction_max 0.8789
_diffrn_reflns_theta_full        26.0000
_diffrn_reflns_theta_max         30.73
_diffrn_reflns_theta_min         3.78
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.5253
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.9860
_diffrn_measured_fraction_theta_max 0.8789
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     23.00  76.10   0.30   10.00    --   22.36-133.00  29.00  177
  2  ω    -45.00  25.20   0.30   10.00    --  -24.08  19.00-120.00  234
  3  ω     37.00  87.10   0.30   10.00    --   22.36  57.00-120.00  167
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0288543000
_diffrn_orient_matrix_UB_12      -0.0673595000
_diffrn_orient_matrix_UB_13      -0.0125646000
_diffrn_orient_matrix_UB_21      -0.0133080000
_diffrn_orient_matrix_UB_22      0.0345168000
_diffrn_orient_matrix_UB_23      -0.0247235000
_diffrn_orient_matrix_UB_31      0.1246161000
_diffrn_orient_matrix_UB_32      0.0192237000
_diffrn_orient_matrix_UB_33      0.0002686000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              7
_reflns_limit_h_min              0
_reflns_limit_k_max              12
_reflns_limit_k_min              0
_reflns_limit_l_max              34
_reflns_limit_l_min              0
_reflns_number_gt                1458
_reflns_number_total             2039
_reflns_odcompleteness_completeness 98.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.2770
_refine_diff_density_min         -0.3309
_refine_diff_density_rms         0.0691
_refine_ls_d_res_high            0.6955
_refine_ls_d_res_low             5.3867
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0116
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    21
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2039
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0772
_refine_ls_R_factor_gt           0.0570
_refine_ls_restrained_S_all      1.0116
_refine_ls_shift/su_max          0.0003
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1P)²+0.0410P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1429
_refine_ls_wR_factor_ref         0.1783
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9a,H9b), C8(H8a,H8b), C7(H7a,H7b), C6(H6a,H6b), C11(H11a,H11b), C12(H12a,
 H12b), C3(H3a,H3b)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
F1 F -0.9160(5) 0.0055(2) -0.58639(10) 0.0740(7) Uani 1.000000 .
O2 O -0.5610(4) -0.2320(2) -0.58447(9) 0.0456(5) Uani 1.000000 .
O1 O -0.9841(5) -0.4617(3) -0.49172(10) 0.0623(7) Uani 1.000000 .
N1 N -0.8443(5) -0.5385(3) -0.56937(10) 0.0418(6) Uani 1.000000 .
F3 F -0.7120(6) -0.0304(3) -0.65586(12) 0.0832(8) Uani 1.000000 .
N2 N -0.4873(5) -0.5387(3) -0.61573(12) 0.0486(7) Uani 1.000000 .
F2 F -1.0819(5) -0.0992(3) -0.65199(10) 0.0797(8) Uani 1.000000 .
C8 C -0.7260(10) -0.6134(5) -0.71406(15) 0.0706(12) Uani 1.000000 .
C6 C -0.6761(9) -0.3393(4) -0.69661(13) 0.0590(9) Uani 1.000000 .
C2 C -0.9370(6) -0.4346(3) -0.53812(12) 0.0425(6) Uani 1.000000 .
C5 C -0.8138(6) -0.3628(3) -0.64478(12) 0.0423(7) Uani 1.000000 .
C12 C -0.7073(7) -0.6615(4) -0.54634(14) 0.0532(8) Uani 1.000000 .
C9 C -0.8468(8) -0.6299(4) -0.66040(14) 0.0553(9) Uani 1.000000 .
C11 C -0.4727(8) -0.6631(4) -0.57897(17) 0.0607(10) Uani 1.000000 .
C1 C -0.8750(8) -0.0912(4) -0.62483(15) 0.0554(9) Uani 1.000000 .
C4 C -0.8005(5) -0.2426(3) -0.60334(11) 0.0396(6) Uani 1.000000 .
C10 C -0.7471(5) -0.5137(3) -0.62265(11) 0.0396(6) Uani 1.000000 .
C3 C -0.9769(6) -0.2822(3) -0.55990(12) 0.0433(7) Uani 1.000000 .
C7 C -0.7547(11) -0.4583(5) -0.73547(15) 0.0780(14) Uani 1.000000 .
H5 H -0.979(10) -0.373(5) -0.6519(19) 0.080(14) Uiso 1.000000 .
H2 H -0.546(7) -0.158(4) -0.5603(17) 0.052(10) Uiso 1.000000 .
H2a H -0.436(8) -0.455(5) -0.5985(19) 0.072(13) Uiso 1.000000 .
H9a H -1.0210(8) -0.6180(4) -0.66388(14) 0.0664(10) Uiso 1.000000 R
H9b H -0.8153(8) -0.7275(4) -0.64664(14) 0.0664(10) Uiso 1.000000 R
H8a H -0.5547(10) -0.6365(5) -0.71107(15) 0.0847(15) Uiso 1.000000 R
H8b H -0.7982(10) -0.6829(5) -0.73828(15) 0.0847(15) Uiso 1.000000 R
H7a H -0.6588(11) -0.4489(5) -0.76709(15) 0.0936(16) Uiso 1.000000 R
H7b H -0.9234(11) -0.4425(5) -0.74474(15) 0.0936(16) Uiso 1.000000 R
H6a H -0.7125(9) -0.2426(4) -0.71061(13) 0.0708(11) Uiso 1.000000 R
H6b H -0.5025(9) -0.3455(4) -0.69061(13) 0.0708(11) Uiso 1.000000 R
H11a H -0.4586(8) -0.7552(4) -0.59792(17) 0.0728(12) Uiso 1.000000 R
H11b H -0.3322(8) -0.6526(4) -0.55645(17) 0.0728(12) Uiso 1.000000 R
H12a H -0.6728(7) -0.6438(4) -0.50970(14) 0.0638(10) Uiso 1.000000 R
H12b H -0.7952(7) -0.7535(4) -0.54978(14) 0.0638(10) Uiso 1.000000 R
H3a H -1.1413(6) -0.2754(3) -0.57324(12) 0.0520(8) Uiso 1.000000 R
H3b H -0.9605(6) -0.2112(3) -0.53184(12) 0.0520(8) Uiso 1.000000 R


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C1 1.338(4) . ?
O2 C4 1.409(3) . ?
O2 H2 0.92(4) . ?
O1 C2 1.240(4) . ?
N1 C2 1.339(4) . ?
N1 C12 1.471(4) . ?
N1 C10 1.482(4) . ?
F3 C1 1.320(5) . ?
N2 C11 1.473(5) . ?
N2 C10 1.460(4) . ?
N2 H2a 0.92(5) . ?
F2 C1 1.337(5) . ?
C8 C9 1.533(5) . ?
C8 C7 1.520(6) . ?
C8 H8a 0.9700 . ?
C8 H8b 0.9700 . ?
C6 C5 1.543(5) . ?
C6 C7 1.532(6) . ?
C6 H6a 0.9700 . ?
C6 H6b 0.9700 . ?
C2 C3 1.509(4) . ?
C5 C4 1.524(4) . ?
C5 C10 1.529(4) . ?
C5 H5 0.94(5) . ?
C12 C11 1.539(5) . ?
C12 H12a 0.9700 . ?
C12 H12b 0.9700 . ?
C9 C10 1.533(4) . ?
C9 H9a 0.9700 . ?
C9 H9b 0.9700 . ?
C11 H11a 0.9700 . ?
C11 H11b 0.9700 . ?
C1 C4 1.538(5) . ?
C4 C3 1.520(4) . ?
C3 H3a 0.9700 . ?
C3 H3b 0.9700 . ?
C7 H7a 0.9700 . ?
C7 H7b 0.9700 . ?

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
H2 O2 C4 111(2) . . ?
C12 N1 C2 119.5(3) . . ?
C10 N1 C2 125.4(2) . . ?
C10 N1 C12 107.4(3) . . ?
C10 N2 C11 104.5(3) . . ?
H2a N2 C11 108(3) . . ?
H2a N2 C10 103(3) . . ?
C7 C8 C9 111.6(3) . . ?
H8a C8 C9 109.3(3) . . ?
H8a C8 C7 109.3(3) . . ?
H8b C8 C9 109.3(2) . . ?
H8b C8 C7 109.3(2) . . ?
H8b C8 H8a 108.0 . . ?
C7 C6 C5 108.7(3) . . ?
H6a C6 C5 109.9(2) . . ?
H6a C6 C7 109.9(2) . . ?
H6b C6 C5 109.9(2) . . ?
H6b C6 C7 109.9(3) . . ?
H6b C6 H6a 108.3 . . ?
N1 C2 O1 120.8(3) . . ?
C3 C2 O1 120.3(3) . . ?
C3 C2 N1 118.8(3) . . ?
C4 C5 C6 118.4(3) . . ?
C10 C5 C6 108.9(3) . . ?
C10 C5 C4 111.9(2) . . ?
H5 C5 C6 109(3) . . ?
H5 C5 C4 105(3) . . ?
H5 C5 C10 102(3) . . ?
C11 C12 N1 102.8(3) . . ?
H12a C12 N1 111.21(17) . . ?
H12a C12 C11 111.2(2) . . ?
H12b C12 N1 111.21(18) . . ?
H12b C12 C11 111.2(2) . . ?
H12b C12 H12a 109.1 . . ?
C10 C9 C8 110.0(3) . . ?
H9a C9 C8 109.7(3) . . ?
H9a C9 C10 109.67(19) . . ?
H9b C9 C8 109.7(2) . . ?
H9b C9 C10 109.67(19) . . ?
H9b C9 H9a 108.2 . . ?
C12 C11 N2 107.0(3) . . ?
H11a C11 N2 110.3(2) . . ?
H11a C11 C12 110.3(2) . . ?
H11b C11 N2 110.3(2) . . ?
H11b C11 C12 110.3(2) . . ?
H11b C11 H11a 108.6 . . ?
F3 C1 F1 106.4(3) . . ?
F2 C1 F1 105.9(3) . . ?
F2 C1 F3 106.9(3) . . ?
C4 C1 F1 111.7(3) . . ?
C4 C1 F3 114.1(3) . . ?
C4 C1 F2 111.4(3) . . ?
C5 C4 O2 109.4(2) . . ?
C1 C4 O2 108.1(3) . . ?
C1 C4 C5 112.3(2) . . ?
C3 C4 O2 111.4(2) . . ?
C3 C4 C5 108.0(2) . . ?
C3 C4 C1 107.6(3) . . ?
N2 C10 N1 102.6(3) . . ?
C5 C10 N1 113.0(2) . . ?
C5 C10 N2 114.9(3) . . ?
C9 C10 N1 110.2(2) . . ?
C9 C10 N2 108.7(3) . . ?
C9 C10 C5 107.3(3) . . ?
C4 C3 C2 113.2(2) . . ?
H3a C3 C2 108.93(16) . . ?
H3a C3 C4 108.93(16) . . ?
H3b C3 C2 108.93(15) . . ?
H3b C3 C4 108.93(16) . . ?
H3b C3 H3a 107.7 . . ?
C6 C7 C8 113.0(3) . . ?
H7a C7 C8 109.0(2) . . ?
H7a C7 C6 109.0(2) . . ?
H7b C7 C8 109.0(3) . . ?
H7b C7 C6 109.0(3) . . ?
H7b C7 H7a 107.8 . . ?

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
F1 C1 C4 O2 -73.3(3) . . . . ?
F1 C1 C4 C5 165.9(3) . . . . ?
F1 C1 C4 C3 47.2(3) . . . . ?
O2 C4 C5 C6 -66.3(3) . . . . ?
O2 C4 C5 C10 61.7(3) . . . . ?
O2 C4 C1 F3 47.4(3) . . . . ?
O2 C4 C1 F2 168.5(3) . . . . ?
O2 C4 C3 C2 -66.3(3) . . . . ?
O1 C2 N1 C12 -24.8(4) . . . . ?
O1 C2 N1 C10 -170.3(3) . . . . ?
O1 C2 C3 C4 149.3(3) . . . . ?
N1 C2 C3 C4 -29.0(3) . . . . ?
N1 C12 C11 N2 2.8(3) . . . . ?
N1 C10 N2 C11 38.5(3) . . . . ?
N1 C10 C5 C6 172.3(3) . . . . ?
N1 C10 C5 C4 39.5(3) . . . . ?
N1 C10 C9 C8 -174.3(3) . . . . ?
F3 C1 C4 C5 -73.4(3) . . . . ?
F3 C1 C4 C3 167.9(3) . . . . ?
N2 C10 C5 C6 55.0(3) . . . . ?
N2 C10 C5 C4 -77.8(3) . . . . ?
N2 C10 C9 C8 -62.5(3) . . . . ?
F2 C1 C4 C5 47.7(3) . . . . ?
F2 C1 C4 C3 -71.1(3) . . . . ?
C8 C9 C10 C5 62.3(4) . . . . ?
C8 C7 C6 C5 -54.0(5) . . . . ?
C6 C5 C4 C1 53.9(4) . . . . ?
C6 C5 C4 C3 172.4(3) . . . . ?
C6 C5 C10 C9 -66.1(3) . . . . ?
C2 C3 C4 C5 53.9(3) . . . . ?
C2 C3 C4 C1 175.3(3) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.338
_oxdiff_exptl_absorpt_empirical_full_min 0.542
####################################################################### 
# 
# 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_exp_1145
_database_code_depnum_ccdc_archive 'CCDC 2107628'
loop_
_audit_author_name
_audit_author_address
'Pavel A. Slepukhin'
;Postovsky Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2021-09-04 deposited with the CCDC.	2021-10-28 downloaded from the CCDC.
;
_audit_creation_date             2021-03-09
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C12 H16 F3 N O3'
_chemical_formula_sum            'C12 H16 F3 N O3'
_chemical_formula_weight         279.26
_chemical_melting_point          ?
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'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   5.6852(3)
_cell_length_b                   9.4367(4)
_cell_length_c                   12.6134(6)
_cell_angle_alpha                77.963(4)
_cell_angle_beta                 77.679(4)
_cell_angle_gamma                76.073(4)
_cell_volume                     632.80(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1919
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.0210
_cell_measurement_theta_min      3.0360
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86156
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.98a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.22
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_unetI/netI     0.0447
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5210
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         29.10
_diffrn_reflns_theta_min         1.68
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9555
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9996
_diffrn_measured_fraction_theta_max 0.8641
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -49.00  34.00   1.00    7.50    --   17.59 -57.00 -60.00   83
  2  ω    -41.00  34.00   1.00    7.50    --   17.59 -57.00-180.00   75
  3  ω     -9.00  32.00   1.00    7.50    --   17.59  77.00  60.00   41
  4  ω     -9.00  36.00   1.00    7.50    --   17.59  77.00 -60.00   45
  5  ω      5.00  38.00   1.00    7.50    --   17.59  77.00 150.00   33
  6  ω    -16.00  10.00   1.00    7.50    --   17.59 -99.00 -90.00   26
  7  ω     14.00  85.00   1.00    7.50    --   17.59  57.00  90.00   71
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0539702000
_diffrn_orient_matrix_UB_12      -0.0538551000
_diffrn_orient_matrix_UB_13      0.0392856000
_diffrn_orient_matrix_UB_21      0.1057235000
_diffrn_orient_matrix_UB_22      -0.0199426000
_diffrn_orient_matrix_UB_23      0.0255149000
_diffrn_orient_matrix_UB_31      -0.0541849000
_diffrn_orient_matrix_UB_32      0.0535577000
_diffrn_orient_matrix_UB_33      0.0348190000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1854
_reflns_number_total             2929
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.41.98a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.98a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.98a (Rigaku OD, 2021)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'J. Appl. Cryst. (2007) 40, 786-790'
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         2929
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0884
_refine_ls_R_factor_gt           0.0501
_refine_ls_restrained_S_all      1.001
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0650P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1116
_refine_ls_wR_factor_ref         0.1374
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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 0.1943(2) 0.08533(12) 0.82293(10) 0.0416(3) Uani 1 1 d . . .
F2 F -0.0874(3) 0.72733(12) 0.71355(12) 0.0797(5) Uani 1 1 d . . .
F3 F -0.2686(3) 0.62979(14) 0.86793(13) 0.0864(5) Uani 1 1 d . . .
O2 O -0.2901(2) 0.49064(15) 0.69690(12) 0.0488(4) Uani 1 1 d . . .
F1 F 0.1249(3) 0.58910(14) 0.83242(13) 0.0841(5) Uani 1 1 d . . .
O3 O 0.2961(3) 0.31853(15) 0.49597(12) 0.0654(5) Uani 1 1 d . . .
N1 N 0.0919(3) 0.20452(16) 0.65153(12) 0.0436(4) Uani 1 1 d . . .
C2 C 0.0047(3) 0.18547(17) 0.76990(14) 0.0367(4) Uani 1 1 d . . .
C9 C 0.1876(4) 0.3196(2) 0.59197(16) 0.0452(5) Uani 1 1 d . . .
C7 C -0.0679(3) 0.46802(18) 0.73694(15) 0.0397(4) Uani 1 1 d . . .
C6 C -0.0465(4) 0.32668(18) 0.82304(15) 0.0381(4) Uani 1 1 d . . .
C1 C -0.0758(4) 0.6032(2) 0.7884(2) 0.0566(6) Uani 1 1 d . . .
C8 C 0.1561(4) 0.4527(2) 0.64555(18) 0.0453(5) Uani 1 1 d . . .
C4 C -0.3272(5) 0.1624(2) 0.91998(19) 0.0557(6) Uani 1 1 d . . .
C10 C 0.3468(5) -0.0423(3) 0.6648(2) 0.0625(7) Uani 1 1 d . . .
C11 C 0.1513(5) 0.0638(2) 0.6071(2) 0.0573(6) Uani 1 1 d . . .
C12 C 0.2690(5) -0.0578(2) 0.78795(19) 0.0548(6) Uani 1 1 d . . .
C3 C -0.2380(4) 0.1317(3) 0.80367(18) 0.0494(5) Uani 1 1 d . . .
C5 C -0.2766(5) 0.3155(2) 0.91270(19) 0.0555(6) Uani 1 1 d . . .
H6 H 0.091(3) 0.3203(17) 0.8587(14) 0.035(5) Uiso 1 1 d . . .
H3A H -0.346(4) 0.191(2) 0.7543(17) 0.061(6) Uiso 1 1 d . . .
H12A H 0.119(4) -0.110(2) 0.8172(16) 0.053(6) Uiso 1 1 d . . .
H4A H -0.227(4) 0.093(2) 0.9742(18) 0.068(7) Uiso 1 1 d . . .
H11A H 0.192(4) 0.091(2) 0.5294(18) 0.056(6) Uiso 1 1 d . . .
H5A H -0.260(4) 0.334(2) 0.983(2) 0.065(7) Uiso 1 1 d . . .
H10A H 0.498(5) 0.000(2) 0.6432(19) 0.070(7) Uiso 1 1 d . . .
H11B H -0.013(5) 0.030(2) 0.6248(19) 0.073(7) Uiso 1 1 d . . .
H10B H 0.373(4) -0.137(3) 0.6428(17) 0.072(7) Uiso 1 1 d . . .
H8A H 0.299(4) 0.443(2) 0.6766(16) 0.054(6) Uiso 1 1 d . . .
H12B H 0.411(4) -0.110(2) 0.8311(17) 0.063(6) Uiso 1 1 d . . .
H2 H -0.291(5) 0.553(3) 0.637(2) 0.074(8) Uiso 1 1 d . . .
H3B H -0.222(4) 0.023(2) 0.7961(17) 0.071(7) Uiso 1 1 d . . .
H4B H -0.500(5) 0.161(2) 0.9461(19) 0.070(7) Uiso 1 1 d . . .
H5B H -0.414(5) 0.386(3) 0.887(2) 0.084(8) Uiso 1 1 d . . .
H8B H 0.147(4) 0.537(2) 0.5869(17) 0.057(6) Uiso 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 C2 1.434(2) . ?
O1 C12 1.446(2) . ?
F2 C1 1.341(2) . ?
F3 C1 1.332(3) . ?
O2 C7 1.412(2) . ?
O2 H2 0.85(2) . ?
F1 C1 1.339(3) . ?
O3 C9 1.237(2) . ?
N1 C2 1.457(2) . ?
N1 C9 1.345(2) . ?
N1 C11 1.485(2) . ?
C2 C6 1.553(2) . ?
C2 C3 1.529(3) . ?
C9 C8 1.504(3) . ?
C7 C6 1.532(2) . ?
C7 C1 1.535(3) . ?
C7 C8 1.525(3) . ?
C6 C5 1.545(3) . ?
C6 H6 0.964(18) . ?
C8 H8A 0.96(2) . ?
C8 H8B 0.96(2) . ?
C4 C3 1.511(3) . ?
C4 C5 1.520(3) . ?
C4 H4A 1.01(2) . ?
C4 H4B 0.97(3) . ?
C10 C11 1.508(3) . ?
C10 C12 1.507(3) . ?
C10 H10A 1.00(3) . ?
C10 H10B 0.96(2) . ?
C11 H11A 0.95(2) . ?
C11 H11B 1.02(3) . ?
C12 H12A 1.04(2) . ?
C12 H12B 1.04(2) . ?
C3 H3A 0.96(2) . ?
C3 H3B 1.03(2) . ?
C5 H5A 0.96(2) . ?
C5 H5B 0.97(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
C2 O1 C12 114.19(14) . . ?
C7 O2 H2 111.6(17) . . ?
C2 N1 C11 113.07(15) . . ?
C9 N1 C2 124.87(14) . . ?
C9 N1 C11 118.76(17) . . ?
O1 C2 N1 108.22(14) . . ?
O1 C2 C6 104.19(13) . . ?
O1 C2 C3 111.24(15) . . ?
N1 C2 C6 115.81(14) . . ?
N1 C2 C3 113.07(15) . . ?
C3 C2 C6 103.96(16) . . ?
O3 C9 N1 121.99(17) . . ?
O3 C9 C8 120.30(18) . . ?
N1 C9 C8 117.71(17) . . ?
O2 C7 C6 108.67(15) . . ?
O2 C7 C1 107.86(14) . . ?
O2 C7 C8 112.11(16) . . ?
C6 C7 C1 110.78(16) . . ?
C8 C7 C6 109.10(14) . . ?
C8 C7 C1 108.33(16) . . ?
C2 C6 H6 107.4(10) . . ?
C7 C6 C2 111.88(14) . . ?
C7 C6 C5 115.37(15) . . ?
C7 C6 H6 108.4(10) . . ?
C5 C6 C2 105.17(15) . . ?
C5 C6 H6 108.3(11) . . ?
F2 C1 C7 111.62(18) . . ?
F3 C1 F2 105.98(16) . . ?
F3 C1 F1 106.55(19) . . ?
F3 C1 C7 113.68(18) . . ?
F1 C1 F2 106.39(18) . . ?
F1 C1 C7 112.11(16) . . ?
C9 C8 C7 112.88(16) . . ?
C9 C8 H8A 108.3(12) . . ?
C9 C8 H8B 105.8(12) . . ?
C7 C8 H8A 108.4(13) . . ?
C7 C8 H8B 112.4(13) . . ?
H8A C8 H8B 109.0(18) . . ?
C3 C4 C5 103.06(18) . . ?
C3 C4 H4A 112.7(12) . . ?
C3 C4 H4B 113.5(14) . . ?
C5 C4 H4A 106.9(12) . . ?
C5 C4 H4B 111.4(13) . . ?
H4A C4 H4B 109.1(18) . . ?
C11 C10 H10A 107.2(13) . . ?
C11 C10 H10B 108.7(14) . . ?
C12 C10 C11 110.8(2) . . ?
C12 C10 H10A 108.9(14) . . ?
C12 C10 H10B 109.5(13) . . ?
H10A C10 H10B 111.7(19) . . ?
N1 C11 C10 108.05(18) . . ?
N1 C11 H11A 105.2(12) . . ?
N1 C11 H11B 103.6(13) . . ?
C10 C11 H11A 117.3(13) . . ?
C10 C11 H11B 113.1(13) . . ?
H11A C11 H11B 108.5(19) . . ?
O1 C12 C10 111.20(17) . . ?
O1 C12 H12A 106.1(11) . . ?
O1 C12 H12B 102.2(11) . . ?
C10 C12 H12A 113.0(11) . . ?
C10 C12 H12B 113.5(12) . . ?
H12A C12 H12B 110.0(17) . . ?
C2 C3 H3A 106.9(13) . . ?
C2 C3 H3B 113.8(13) . . ?
C4 C3 C2 103.38(17) . . ?
C4 C3 H3A 112.0(12) . . ?
C4 C3 H3B 114.0(12) . . ?
H3A C3 H3B 106.7(17) . . ?
C6 C5 H5A 113.6(14) . . ?
C6 C5 H5B 107.8(15) . . ?
C4 C5 C6 106.25(17) . . ?
C4 C5 H5A 112.4(13) . . ?
C4 C5 H5B 106.9(15) . . ?
H5A C5 H5B 109.5(19) . . ?

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
O1 C2 C6 C7 135.54(15) . . . . ?
O1 C2 C6 C5 -98.49(17) . . . . ?
O1 C2 C3 C4 73.8(2) . . . . ?
O2 C7 C6 C2 70.98(19) . . . . ?
O2 C7 C6 C5 -49.2(2) . . . . ?
O2 C7 C1 F2 -63.0(2) . . . . ?
O2 C7 C1 F3 56.8(2) . . . . ?
O2 C7 C1 F1 177.75(18) . . . . ?
O2 C7 C8 C9 -63.3(2) . . . . ?
O3 C9 C8 C7 153.79(19) . . . . ?
N1 C2 C6 C7 16.8(2) . . . . ?
N1 C2 C6 C5 142.78(17) . . . . ?
N1 C2 C3 C4 -164.22(15) . . . . ?
N1 C9 C8 C7 -25.5(2) . . . . ?
C2 O1 C12 C10 55.1(2) . . . . ?
C2 N1 C9 O3 167.58(18) . . . . ?
C2 N1 C9 C8 -13.1(3) . . . . ?
C2 N1 C11 C10 -58.9(3) . . . . ?
C2 C6 C5 C4 8.0(2) . . . . ?
C9 N1 C2 O1 -99.00(19) . . . . ?
C9 N1 C2 C6 17.5(3) . . . . ?
C9 N1 C2 C3 137.3(2) . . . . ?
C9 N1 C11 C10 101.6(2) . . . . ?
C7 C6 C5 C4 131.73(19) . . . . ?
C6 C2 C3 C4 -37.8(2) . . . . ?
C6 C7 C1 F2 178.19(17) . . . . ?
C6 C7 C1 F3 -62.0(2) . . . . ?
C6 C7 C1 F1 58.9(2) . . . . ?
C6 C7 C8 C9 57.1(2) . . . . ?
C1 C7 C6 C2 -170.69(16) . . . . ?
C1 C7 C6 C5 69.1(2) . . . . ?
C1 C7 C8 C9 177.78(16) . . . . ?
C8 C7 C6 C2 -51.5(2) . . . . ?
C8 C7 C6 C5 -171.70(17) . . . . ?
C8 C7 C1 F2 58.6(2) . . . . ?
C8 C7 C1 F3 178.38(17) . . . . ?
C8 C7 C1 F1 -60.7(2) . . . . ?
C11 N1 C2 O1 60.1(2) . . . . ?
C11 N1 C2 C6 176.58(17) . . . . ?
C11 N1 C2 C3 -63.6(2) . . . . ?
C11 N1 C9 O3 9.6(3) . . . . ?
C11 N1 C9 C8 -171.14(18) . . . . ?
C11 C10 C12 O1 -52.1(3) . . . . ?
C12 O1 C2 N1 -57.69(19) . . . . ?
C12 O1 C2 C6 178.53(16) . . . . ?
C12 O1 C2 C3 67.1(2) . . . . ?
C12 C10 C11 N1 53.2(3) . . . . ?
C3 C2 C6 C7 -107.84(18) . . . . ?
C3 C2 C6 C5 18.12(19) . . . . ?
C3 C4 C5 C6 -31.3(2) . . . . ?
C5 C4 C3 C2 42.9(2) . . . . ?

_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.077
_oxdiff_exptl_absorpt_empirical_full_min 0.900
####################################################################### 
# 
# 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_exp_764
_database_code_depnum_ccdc_archive 'CCDC 2107623'
loop_
_audit_author_name
_audit_author_address
'Pavel A. Slepukhin'
;Postovsky Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2021-09-04 deposited with the CCDC.	2021-10-28 downloaded from the CCDC.
;
_audit_creation_date             2020-06-03
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C13 H19 F3 N2 O2'
_chemical_formula_sum            'C13 H19 F3 N2 O2'
_chemical_formula_weight         292.30
_chemical_melting_point          ?
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'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   6.6874(6)
_cell_length_b                   17.3402(14)
_cell_length_c                   11.9242(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.885(8)
_cell_angle_gamma                90.00
_cell_volume                     1372.8(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1851
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      26.9120
_cell_measurement_theta_min      3.8470
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73415
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.38a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.25
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_av_unetI/netI     0.0506
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9635
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         30.81
_diffrn_reflns_theta_min         3.53
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.5253
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.9920
_diffrn_measured_fraction_theta_max 0.8571
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      1.00  90.00   1.00   20.00    --   22.36  61.00 157.00   89
  2  ω    -42.00  42.00   1.00   20.00    --   22.36 -61.00  18.00   84
  3  ω     19.00  44.00   1.00   20.00    --  -23.92  61.00 157.00   25
  4  ω    -71.00 -46.00   1.00   20.00    --  -23.92 -61.00  18.00   25
  5  ω     -8.00  92.00   1.00   20.00    --   22.36  77.00-120.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0492907000
_diffrn_orient_matrix_UB_12      -0.0009105000
_diffrn_orient_matrix_UB_13      -0.0560847000
_diffrn_orient_matrix_UB_21      -0.0656729000
_diffrn_orient_matrix_UB_22      -0.0291691000
_diffrn_orient_matrix_UB_23      0.0156764000
_diffrn_orient_matrix_UB_31      -0.0683636000
_diffrn_orient_matrix_UB_32      0.0286462000
_diffrn_orient_matrix_UB_33      0.0141439000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2056
_reflns_number_total             3688
_reflns_odcompleteness_completeness 99.20
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'J. Appl. Cryst. (2007) 40, 786-790'
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.025(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3688
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1202
_refine_ls_R_factor_gt           0.0645
_refine_ls_restrained_S_all      1.006
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1100P)²+0.4000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1707
_refine_ls_wR_factor_ref         0.2292
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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 0.5612(3) 0.44575(10) 0.22541(16) 0.0493(5) Uani 1 1 d . . .
F2 F 0.9443(3) 0.57773(12) 0.3311(2) 0.0944(8) Uani 1 1 d . . .
F3 F 0.6316(4) 0.60319(11) 0.2812(2) 0.0970(8) Uani 1 1 d . . .
F1 F 0.7163(4) 0.52128(12) 0.41291(17) 0.0887(7) Uani 1 1 d . . .
O2 O 0.7289(3) 0.48452(13) -0.08344(16) 0.0664(6) Uani 1 1 d . . .
N1 N 0.8341(3) 0.38995(12) 0.03951(17) 0.0460(5) Uani 1 1 d . . .
N2 N 0.7469(4) 0.30254(12) 0.18458(19) 0.0493(6) Uani 1 1 d . . .
C10 C 0.8951(4) 0.35836(13) 0.15580(19) 0.0407(5) Uani 1 1 d . . .
C2 C 0.7765(4) 0.46279(16) 0.0160(2) 0.0477(6) Uani 1 1 d . . .
C5 C 0.9224(3) 0.42416(14) 0.2431(2) 0.0408(5) Uani 1 1 d . . .
C4 C 0.7496(4) 0.48267(13) 0.2237(2) 0.0440(6) Uani 1 1 d . . .
C3 C 0.7684(4) 0.51984(14) 0.1099(2) 0.0508(7) Uani 1 1 d . . .
H3A H 0.6544 0.5539 0.0906 0.061 Uiso 1 1 calc R . .
H3B H 0.8895 0.5511 0.1163 0.061 Uiso 1 1 calc R . .
C9 C 1.1022(4) 0.31880(17) 0.1586(2) 0.0508(6) Uani 1 1 d . . .
C6 C 0.9760(5) 0.39037(18) 0.3615(2) 0.0530(7) Uani 1 1 d . . .
C8 C 1.1725(5) 0.28599(19) 0.2748(3) 0.0610(8) Uani 1 1 d . . .
C12 C 0.6375(5) 0.27610(19) -0.0183(3) 0.0697(9) Uani 1 1 d . . .
H12A H 0.6215 0.2345 -0.0729 0.084 Uiso 1 1 calc R . .
H12B H 0.5097 0.3028 -0.0207 0.084 Uiso 1 1 calc R . .
C1 C 0.7607(5) 0.54557(18) 0.3130(3) 0.0676(9) Uani 1 1 d . . .
C7 C 1.1746(5) 0.34562(19) 0.3667(3) 0.0609(8) Uani 1 1 d . . .
C13 C 0.7960(5) 0.33123(19) -0.0491(2) 0.0631(8) Uani 1 1 d . . .
H13A H 0.9193 0.3034 -0.0570 0.076 Uiso 1 1 calc R . .
H13B H 0.7506 0.3558 -0.1208 0.076 Uiso 1 1 calc R . .
C11 C 0.6950(5) 0.24310(17) 0.0987(3) 0.0637(8) Uani 1 1 d . . .
H11A H 0.5834 0.2128 0.1198 0.076 Uiso 1 1 calc R . .
H11B H 0.8091 0.2088 0.0970 0.076 Uiso 1 1 calc R . .
H6A H 0.998(5) 0.4292(18) 0.416(3) 0.063(9) Uiso 1 1 d . . .
H5 H 1.043(4) 0.4518(13) 0.2253(19) 0.037(6) Uiso 1 1 d . . .
H8A H 1.081(5) 0.2421(19) 0.287(3) 0.068(9) Uiso 1 1 d . . .
H7A H 1.283(5) 0.3838(17) 0.363(3) 0.060(8) Uiso 1 1 d . . .
H9A H 1.199(4) 0.3588(14) 0.132(2) 0.046(7) Uiso 1 1 d . . .
H7B H 1.207(5) 0.3196(17) 0.440(3) 0.065(8) Uiso 1 1 d . . .
H2 H 0.637(5) 0.3270(18) 0.193(3) 0.060(9) Uiso 1 1 d . . .
H8B H 1.305(6) 0.264(2) 0.271(3) 0.078(10) Uiso 1 1 d . . .
H1 H 0.474(6) 0.4712(19) 0.183(3) 0.075(11) Uiso 1 1 d . . .
H6B H 0.865(4) 0.3571(15) 0.382(2) 0.051(7) Uiso 1 1 d . . .
H9B H 1.096(5) 0.2752(18) 0.105(3) 0.066(9) Uiso 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 C4 1.416(3) . ?
O1 H1 0.85(4) . ?
F2 C1 1.342(4) . ?
F3 C1 1.345(4) . ?
F1 C1 1.331(4) . ?
O2 C2 1.249(3) . ?
N1 C10 1.501(3) . ?
N1 C2 1.340(3) . ?
N1 C13 1.468(3) . ?
N2 C10 1.455(3) . ?
N2 C11 1.465(4) . ?
N2 H2 0.86(3) . ?
C10 C5 1.541(3) . ?
C10 C9 1.542(3) . ?
C2 C3 1.499(4) . ?
C5 C4 1.534(3) . ?
C5 C6 1.531(3) . ?
C5 H5 0.98(2) . ?
C4 C3 1.521(4) . ?
C4 C1 1.520(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C9 C8 1.519(4) . ?
C9 H9A 1.02(3) . ?
C9 H9B 0.99(3) . ?
C6 C7 1.533(4) . ?
C6 H6A 0.93(3) . ?
C6 H6B 1.00(3) . ?
C8 C7 1.506(5) . ?
C8 H8A 1.00(3) . ?
C8 H8B 0.97(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.505(5) . ?
C12 C11 1.514(5) . ?
C7 H7A 0.98(3) . ?
C7 H7B 0.98(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?

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
C4 O1 H1 108(2) . . ?
C2 N1 C10 125.2(2) . . ?
C2 N1 C13 118.8(2) . . ?
C13 N1 C10 114.6(2) . . ?
C10 N2 C11 114.5(2) . . ?
C10 N2 H2 108(2) . . ?
C11 N2 H2 107(2) . . ?
N1 C10 C5 110.54(18) . . ?
N1 C10 C9 109.0(2) . . ?
N2 C10 N1 110.06(18) . . ?
N2 C10 C5 111.2(2) . . ?
N2 C10 C9 109.5(2) . . ?
C5 C10 C9 106.36(19) . . ?
O2 C2 N1 121.1(3) . . ?
O2 C2 C3 118.8(2) . . ?
N1 C2 C3 120.1(2) . . ?
C10 C5 H5 104.4(14) . . ?
C4 C5 C10 111.21(18) . . ?
C4 C5 H5 105.5(14) . . ?
C6 C5 C10 109.6(2) . . ?
C6 C5 C4 118.8(2) . . ?
C6 C5 H5 106.1(13) . . ?
O1 C4 C5 110.74(19) . . ?
O1 C4 C3 111.93(19) . . ?
O1 C4 C1 106.4(2) . . ?
C3 C4 C5 105.9(2) . . ?
C1 C4 C5 113.3(2) . . ?
C1 C4 C3 108.6(2) . . ?
C2 C3 C4 113.6(2) . . ?
C2 C3 H3A 108.8 . . ?
C2 C3 H3B 108.8 . . ?
C4 C3 H3A 108.8 . . ?
C4 C3 H3B 108.8 . . ?
H3A C3 H3B 107.7 . . ?
C10 C9 H9A 106.9(15) . . ?
C10 C9 H9B 111.1(18) . . ?
C8 C9 C10 111.4(2) . . ?
C8 C9 H9A 113.5(15) . . ?
C8 C9 H9B 106.5(17) . . ?
H9A C9 H9B 107(2) . . ?
C5 C6 C7 109.7(2) . . ?
C5 C6 H6A 111.3(19) . . ?
C5 C6 H6B 110.3(15) . . ?
C7 C6 H6A 105.7(19) . . ?
C7 C6 H6B 111.5(16) . . ?
H6A C6 H6B 108(3) . . ?
C9 C8 H8A 106.7(18) . . ?
C9 C8 H8B 107(2) . . ?
C7 C8 C9 112.4(2) . . ?
C7 C8 H8A 111.8(19) . . ?
C7 C8 H8B 112(2) . . ?
H8A C8 H8B 107(3) . . ?
H12A C12 H12B 108.0 . . ?
C13 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
C13 C12 C11 110.9(2) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
F2 C1 F3 106.3(3) . . ?
F2 C1 C4 112.2(3) . . ?
F3 C1 C4 111.1(3) . . ?
F1 C1 F2 106.6(3) . . ?
F1 C1 F3 106.4(3) . . ?
F1 C1 C4 113.8(3) . . ?
C6 C7 H7A 107.1(18) . . ?
C6 C7 H7B 111.5(19) . . ?
C8 C7 C6 112.7(2) . . ?
C8 C7 H7A 112.0(19) . . ?
C8 C7 H7B 108.2(17) . . ?
H7A C7 H7B 105(2) . . ?
N1 C13 C12 109.3(2) . . ?
N1 C13 H13A 109.8 . . ?
N1 C13 H13B 109.8 . . ?
C12 C13 H13A 109.8 . . ?
C12 C13 H13B 109.8 . . ?
H13A C13 H13B 108.3 . . ?
N2 C11 C12 113.0(2) . . ?
N2 C11 H11A 109.0 . . ?
N2 C11 H11B 109.0 . . ?
C12 C11 H11A 109.0 . . ?
C12 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?

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
O1 C4 C3 C2 -67.5(3) . . . . ?
O1 C4 C1 F2 171.0(2) . . . . ?
O1 C4 C1 F3 -70.1(3) . . . . ?
O1 C4 C1 F1 49.9(3) . . . . ?
O2 C2 C3 C4 157.8(2) . . . . ?
N1 C10 C5 C4 44.3(3) . . . . ?
N1 C10 C5 C6 177.7(2) . . . . ?
N1 C10 C9 C8 179.7(2) . . . . ?
N1 C2 C3 C4 -22.2(3) . . . . ?
N2 C10 C5 C4 -78.2(2) . . . . ?
N2 C10 C5 C6 55.1(3) . . . . ?
N2 C10 C9 C8 -59.8(3) . . . . ?
C10 N1 C2 O2 179.6(2) . . . . ?
C10 N1 C2 C3 -0.3(4) . . . . ?
C10 N1 C13 C12 56.5(3) . . . . ?
C10 N2 C11 C12 -51.1(3) . . . . ?
C10 C5 C4 O1 56.1(3) . . . . ?
C10 C5 C4 C3 -65.5(2) . . . . ?
C10 C5 C4 C1 175.6(2) . . . . ?
C10 C5 C6 C7 61.1(3) . . . . ?
C10 C9 C8 C7 -54.5(3) . . . . ?
C2 N1 C10 N2 112.3(3) . . . . ?
C2 N1 C10 C5 -10.9(3) . . . . ?
C2 N1 C10 C9 -127.5(3) . . . . ?
C2 N1 C13 C12 -111.0(3) . . . . ?
C5 C10 C9 C8 60.5(3) . . . . ?
C5 C4 C3 C2 53.3(2) . . . . ?
C5 C4 C1 F2 49.1(3) . . . . ?
C5 C4 C1 F3 167.9(3) . . . . ?
C5 C4 C1 F1 -72.0(3) . . . . ?
C5 C6 C7 C8 -53.3(3) . . . . ?
C4 C5 C6 C7 -169.6(2) . . . . ?
C3 C4 C1 F2 -68.3(3) . . . . ?
C3 C4 C1 F3 50.6(3) . . . . ?
C3 C4 C1 F1 170.6(2) . . . . ?
C9 C10 C5 C4 162.6(2) . . . . ?
C9 C10 C5 C6 -64.1(3) . . . . ?
C9 C8 C7 C6 50.2(4) . . . . ?
C6 C5 C4 O1 -72.5(3) . . . . ?
C6 C5 C4 C3 166.0(2) . . . . ?
C6 C5 C4 C1 47.0(3) . . . . ?
C1 C4 C3 C2 175.3(2) . . . . ?
C13 N1 C10 N2 -54.3(3) . . . . ?
C13 N1 C10 C5 -177.5(2) . . . . ?
C13 N1 C10 C9 65.9(3) . . . . ?
C13 N1 C2 O2 -14.3(4) . . . . ?
C13 N1 C2 C3 165.7(2) . . . . ?
C13 C12 C11 N2 51.9(4) . . . . ?
C11 N2 C10 N1 50.3(3) . . . . ?
C11 N2 C10 C5 173.1(2) . . . . ?
C11 N2 C10 C9 -69.6(3) . . . . ?
C11 C12 C13 N1 -53.6(3) . . . . ?

_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.113
_oxdiff_exptl_absorpt_empirical_full_min 0.861
####################################################################### 
# 
# 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_exp_586
_database_code_depnum_ccdc_archive 'CCDC 2107629'
loop_
_audit_author_name
_audit_author_address
'Pavel A. Slepukhin'
;Postovsky Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2021-09-04 deposited with the CCDC.	2021-10-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H20 F3 N O4'
_chemical_formula_sum            'C13 H20 F3 N O4'
_chemical_formula_weight         311.30

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   13.671(2)
_cell_length_b                   5.8015(8)
_cell_length_c                   18.074(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.430(14)
_cell_angle_gamma                90.00
_cell_volume                     1430.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    1220
_cell_measurement_theta_min      3.8590
_cell_measurement_theta_max      28.7260

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_T_min  0.15591
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.38a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(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  'Xcalibur 3'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9774
_diffrn_reflns_av_R_equivalents  0.0643
_diffrn_reflns_av_sigmaI/netI    0.0983
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.69
_diffrn_reflns_theta_max         30.93
_reflns_number_total             3846
_reflns_number_gt                1635
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0900P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.014(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3846
_refine_ls_number_parameters     207
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1629
_refine_ls_R_factor_gt           0.0703
_refine_ls_wR_factor_ref         0.2356
_refine_ls_wR_factor_gt          0.1661
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_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
N1 N 0.32627(17) 0.9125(4) 0.18374(13) 0.0380(6) Uani 1 1 d . . .
O1 O 0.29997(18) 0.6182(4) 0.02750(13) 0.0530(7) Uani 1 1 d . . .
F1 F 0.25125(19) 0.9590(4) -0.09003(11) 0.0820(8) Uani 1 1 d . . .
C1 C 0.1939(3) 0.8829(7) -0.0381(2) 0.0648(10) Uani 1 1 d . . .
O2 O 0.44156(17) 1.1453(4) 0.14172(13) 0.0617(7) Uani 1 1 d . . .
C2 C 0.3663(2) 1.0305(5) 0.12958(17) 0.0424(7) Uani 1 1 d . . .
F2 F 0.1464(2) 0.7025(5) -0.06875(12) 0.1039(10) Uani 1 1 d . . .
O3 O 0.42375(18) 0.9048(4) 0.42043(12) 0.0588(7) Uani 1 1 d . . .
C3 C 0.3199(2) 1.0263(5) 0.05194(16) 0.0463(8) Uani 1 1 d . . .
H3A H 0.3716 1.0197 0.0175 0.056 Uiso 1 1 calc R . .
H3B H 0.2849 1.1701 0.0431 0.056 Uiso 1 1 calc R . .
F3 F 0.1264(2) 1.0477(6) -0.03067(13) 0.1053(10) Uani 1 1 d . . .
O4 O 0.27829(17) 0.5236(4) 0.17456(14) 0.0532(6) Uani 1 1 d . . .
C4 C 0.2495(2) 0.8287(5) 0.03459(16) 0.0423(7) Uani 1 1 d . . .
C5 C 0.1822(2) 0.8058(6) 0.09904(16) 0.0427(7) Uani 1 1 d . . .
C6 C 0.0977(3) 0.6323(7) 0.0883(2) 0.0614(10) Uani 1 1 d . . .
H6A H 0.0594 0.6675 0.0428 0.074 Uiso 1 1 calc R . .
H6B H 0.1243 0.4782 0.0839 0.074 Uiso 1 1 calc R . .
C7 C 0.0324(3) 0.6401(8) 0.1528(2) 0.0765(13) Uani 1 1 d . . .
H7A H -0.0175 0.5216 0.1463 0.092 Uiso 1 1 calc R . .
H7B H -0.0005 0.7883 0.1533 0.092 Uiso 1 1 calc R . .
C8 C 0.0892(3) 0.6041(7) 0.2265(2) 0.0700(11) Uani 1 1 d . . .
H8A H 0.1138 0.4473 0.2293 0.084 Uiso 1 1 calc R . .
H8B H 0.0458 0.6259 0.2665 0.084 Uiso 1 1 calc R . .
C9 C 0.1745(2) 0.7716(6) 0.23591(18) 0.0511(8) Uani 1 1 d . . .
H9A H 0.1494 0.9276 0.2381 0.061 Uiso 1 1 calc R . .
H9B H 0.2113 0.7398 0.2823 0.061 Uiso 1 1 calc R . .
C10 C 0.2423(2) 0.7530(5) 0.17245(15) 0.0384(7) Uani 1 1 d . . .
C11 C 0.3835(2) 0.9041(5) 0.25633(16) 0.0449(8) Uani 1 1 d . . .
H11A H 0.4528 0.9076 0.2476 0.054 Uiso 1 1 calc R . .
H11B H 0.3701 0.7592 0.2806 0.054 Uiso 1 1 calc R . .
C12 C 0.3606(2) 1.1007(6) 0.30781(17) 0.0479(8) Uani 1 1 d . . .
H12A H 0.2942 1.0833 0.3232 0.057 Uiso 1 1 calc R . .
H12B H 0.3641 1.2454 0.2812 0.057 Uiso 1 1 calc R . .
C13 C 0.4310(3) 1.1080(6) 0.37586(18) 0.0527(9) Uani 1 1 d . . .
H13A H 0.4975 1.1225 0.3604 0.063 Uiso 1 1 calc R . .
H13B H 0.4169 1.2424 0.4053 0.063 Uiso 1 1 calc R . .
H5 H 0.151(2) 0.967(5) 0.1035(15) 0.042(8) Uiso 1 1 d . . .
H4 H 0.310(3) 0.516(6) 0.132(2) 0.063(11) Uiso 1 1 d . . .
H1 H 0.343(4) 0.618(8) -0.013(3) 0.116(17) Uiso 1 1 d . . .
H3 H 0.475(3) 0.780(8) 0.406(2) 0.101(15) Uiso 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
N1 C2 1.338(4) . ?
N1 C10 1.479(4) . ?
N1 C11 1.487(4) . ?
O1 C4 1.412(4) . ?
O1 H1 0.96(5) . ?
F1 C1 1.334(4) . ?
C1 F2 1.334(4) . ?
C1 F3 1.341(5) . ?
C1 C4 1.510(5) . ?
O2 C2 1.234(3) . ?
C2 C3 1.505(4) . ?
O3 C13 1.435(4) . ?
O3 H3 1.05(5) . ?
C3 C4 1.518(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
O4 C10 1.419(4) . ?
O4 H4 0.91(4) . ?
C4 C5 1.533(4) . ?
C5 C6 1.535(4) . ?
C5 C10 1.549(4) . ?
C5 H5 1.04(3) . ?
C6 C7 1.511(5) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.516(6) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.520(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.521(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C11 C12 1.516(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.517(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?

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
C2 N1 C10 124.6(2) . . ?
C2 N1 C11 116.4(2) . . ?
C10 N1 C11 117.6(2) . . ?
C4 O1 H1 113(3) . . ?
F1 C1 F2 105.0(3) . . ?
F1 C1 F3 105.7(3) . . ?
F2 C1 F3 106.3(3) . . ?
F1 C1 C4 113.3(3) . . ?
F2 C1 C4 113.9(3) . . ?
F3 C1 C4 112.0(3) . . ?
O2 C2 N1 121.3(3) . . ?
O2 C2 C3 118.4(3) . . ?
N1 C2 C3 120.3(3) . . ?
C13 O3 H3 111(2) . . ?
C2 C3 C4 115.6(2) . . ?
C2 C3 H3A 108.4 . . ?
C4 C3 H3A 108.4 . . ?
C2 C3 H3B 108.4 . . ?
C4 C3 H3B 108.4 . . ?
H3A C3 H3B 107.4 . . ?
C10 O4 H4 102(2) . . ?
O1 C4 C1 108.9(3) . . ?
O1 C4 C3 111.4(3) . . ?
C1 C4 C3 107.6(3) . . ?
O1 C4 C5 108.2(2) . . ?
C1 C4 C5 112.7(3) . . ?
C3 C4 C5 108.1(2) . . ?
C6 C5 C4 116.2(3) . . ?
C6 C5 C10 109.6(3) . . ?
C4 C5 C10 110.9(2) . . ?
C6 C5 H5 106.8(16) . . ?
C4 C5 H5 104.6(15) . . ?
C10 C5 H5 108.3(16) . . ?
C7 C6 C5 111.0(3) . . ?
C7 C6 H6A 109.4 . . ?
C5 C6 H6A 109.4 . . ?
C7 C6 H6B 109.4 . . ?
C5 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C6 C7 C8 112.2(3) . . ?
C6 C7 H7A 109.2 . . ?
C8 C7 H7A 109.2 . . ?
C6 C7 H7B 109.2 . . ?
C8 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C7 C8 C9 111.1(3) . . ?
C7 C8 H8A 109.4 . . ?
C9 C8 H8A 109.4 . . ?
C7 C8 H8B 109.4 . . ?
C9 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
C10 C9 C8 111.6(3) . . ?
C10 C9 H9A 109.3 . . ?
C8 C9 H9A 109.3 . . ?
C10 C9 H9B 109.3 . . ?
C8 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
O4 C10 N1 108.5(2) . . ?
O4 C10 C9 105.8(2) . . ?
N1 C10 C9 110.8(2) . . ?
O4 C10 C5 111.9(2) . . ?
N1 C10 C5 111.3(2) . . ?
C9 C10 C5 108.4(2) . . ?
N1 C11 C12 113.6(2) . . ?
N1 C11 H11A 108.9 . . ?
C12 C11 H11A 108.9 . . ?
N1 C11 H11B 108.9 . . ?
C12 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
C11 C12 C13 112.0(3) . . ?
C11 C12 H12A 109.2 . . ?
C13 C12 H12A 109.2 . . ?
C11 C12 H12B 109.2 . . ?
C13 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
O3 C13 C12 111.8(3) . . ?
O3 C13 H13A 109.3 . . ?
C12 C13 H13A 109.3 . . ?
O3 C13 H13B 109.3 . . ?
C12 C13 H13B 109.3 . . ?
H13A C13 H13B 107.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 N1 C2 O2 -173.7(3) . . . . ?
C11 N1 C2 O2 -7.2(4) . . . . ?
C10 N1 C2 C3 6.5(4) . . . . ?
C11 N1 C2 C3 173.0(2) . . . . ?
O2 C2 C3 C4 161.2(3) . . . . ?
N1 C2 C3 C4 -19.0(4) . . . . ?
F1 C1 C4 O1 -75.5(4) . . . . ?
F2 C1 C4 O1 44.3(4) . . . . ?
F3 C1 C4 O1 165.0(3) . . . . ?
F1 C1 C4 C3 45.3(4) . . . . ?
F2 C1 C4 C3 165.2(3) . . . . ?
F3 C1 C4 C3 -74.2(4) . . . . ?
F1 C1 C4 C5 164.4(3) . . . . ?
F2 C1 C4 C5 -75.8(4) . . . . ?
F3 C1 C4 C5 44.9(4) . . . . ?
C2 C3 C4 O1 -73.4(3) . . . . ?
C2 C3 C4 C1 167.3(3) . . . . ?
C2 C3 C4 C5 45.4(4) . . . . ?
O1 C4 C5 C6 -65.9(3) . . . . ?
C1 C4 C5 C6 54.6(4) . . . . ?
C3 C4 C5 C6 173.4(3) . . . . ?
O1 C4 C5 C10 60.1(3) . . . . ?
C1 C4 C5 C10 -179.3(3) . . . . ?
C3 C4 C5 C10 -60.6(3) . . . . ?
C4 C5 C6 C7 -175.4(3) . . . . ?
C10 C5 C6 C7 58.0(4) . . . . ?
C5 C6 C7 C8 -54.8(4) . . . . ?
C6 C7 C8 C9 53.3(4) . . . . ?
C7 C8 C9 C10 -56.2(4) . . . . ?
C2 N1 C10 O4 102.0(3) . . . . ?
C11 N1 C10 O4 -64.2(3) . . . . ?
C2 N1 C10 C9 -142.2(3) . . . . ?
C11 N1 C10 C9 51.5(3) . . . . ?
C2 N1 C10 C5 -21.6(4) . . . . ?
C11 N1 C10 C5 172.2(2) . . . . ?
C8 C9 C10 O4 -60.9(3) . . . . ?
C8 C9 C10 N1 -178.4(3) . . . . ?
C8 C9 C10 C5 59.3(4) . . . . ?
C6 C5 C10 O4 56.7(3) . . . . ?
C4 C5 C10 O4 -72.9(3) . . . . ?
C6 C5 C10 N1 178.3(2) . . . . ?
C4 C5 C10 N1 48.7(3) . . . . ?
C6 C5 C10 C9 -59.6(3) . . . . ?
C4 C5 C10 C9 170.7(2) . . . . ?
C2 N1 C11 C12 89.6(3) . . . . ?
C10 N1 C11 C12 -103.0(3) . . . . ?
N1 C11 C12 C13 -171.0(3) . . . . ?
C11 C12 C13 O3 -63.2(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.847
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.058


####################################################################### 
# 
# 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_exp_936
_database_code_depnum_ccdc_archive 'CCDC 2107626'
loop_
_audit_author_name
_audit_author_address
'Pavel A. Slepukhin'
;Postovsky Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2021-09-04 deposited with the CCDC.	2021-10-28 downloaded from the CCDC.
;
_audit_creation_date             2021-03-17
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H14 F3 N O3'
_chemical_formula_sum            'C11 H14 F3 N O3'
_chemical_formula_weight         265.23
_chemical_melting_point          ?
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'
F F 0.0171 0.0103 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.4368(6)
_cell_length_b                   8.6060(7)
_cell_length_c                   12.6785(11)
_cell_angle_alpha                93.198(7)
_cell_angle_beta                 100.084(8)
_cell_angle_gamma                92.872(8)
_cell_volume                     582.06(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1085
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      28.4020
_cell_measurement_theta_min      4.1820
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.942
_exptl_absorpt_coefficient_mu    0.140
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82866
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.38a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_unetI/netI     0.0719
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.857
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5258
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.857
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.865
_diffrn_reflns_theta_min         3.814
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.5253
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.857
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -18.00  23.00   1.00   12.00    --  -24.08 101.00-113.00   41
  2  ω    -65.00 -38.00   1.00   12.00    --  -24.08 101.00-113.00   27
  3  ω    -23.00  65.00   1.00   12.00    --   22.52-101.00 142.00   88
  4  ω     35.00  81.00   1.00   12.00    --   22.52 178.00 -90.00   46
  5  ω    -93.00  -7.00   1.00   12.00    --  -24.08 -57.00-120.00   86
  6  ω    -90.00   2.00   1.00   12.00    --  -24.08 -77.00   0.00   92
  7  ω      9.00  33.00   1.00   12.00    --  -24.08  57.00  30.00   24
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0466616000
_diffrn_orient_matrix_UB_12      -0.0211029000
_diffrn_orient_matrix_UB_13      0.0527331000
_diffrn_orient_matrix_UB_21      0.0552466000
_diffrn_orient_matrix_UB_22      0.0765442000
_diffrn_orient_matrix_UB_23      0.0135303000
_diffrn_orient_matrix_UB_31      -0.1113319000
_diffrn_orient_matrix_UB_32      0.0231331000
_diffrn_orient_matrix_UB_33      0.0167021000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1715
_reflns_number_total             3141
_reflns_odcompleteness_completeness 98.30
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       0.032(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         3141
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1090
_refine_ls_R_factor_gt           0.0564
_refine_ls_restrained_S_all      1.011
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0548P)²+0.1499P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1207
_refine_ls_wR_factor_ref         0.1697
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C6(H6A,H6B), C8(H8A,H8B), C7(H7A,H7B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O15 O 0.8285(3) 0.47213(19) 0.66283(14) 0.0415(4) Uani 1 1 d . . . . .
F1 F 0.5247(3) 0.23944(17) 0.70977(13) 0.0636(5) Uani 1 1 d . . . . .
F2 F 0.3979(3) 0.3721(2) 0.83514(13) 0.0711(5) Uani 1 1 d . . . . .
F3 F 0.7835(3) 0.31696(19) 0.85252(14) 0.0749(6) Uani 1 1 d . . . . .
O4 O 1.0486(3) 0.8423(2) 0.75911(15) 0.0499(5) Uani 1 1 d . . . . .
O14 O 0.3951(4) 0.7199(2) 0.50992(14) 0.0554(5) Uani 1 1 d . . . . .
N1 N 0.6630(4) 0.8088(2) 0.65828(15) 0.0384(5) Uani 1 1 d . . . . .
C10 C 0.6544(4) 0.5089(3) 0.73023(17) 0.0360(5) Uani 1 1 d . . . . .
C12 C 0.4890(4) 0.7044(3) 0.60440(18) 0.0382(5) Uani 1 1 d . . . . .
C5 C 0.7968(4) 0.7989(3) 0.76830(18) 0.0367(5) Uani 1 1 d . . . . .
C9 C 0.7857(5) 0.6349(3) 0.81421(18) 0.0386(5) Uani 1 1 d . . . . .
C11 C 0.4179(4) 0.5686(3) 0.66523(19) 0.0404(6) Uani 1 1 d . . . . .
H11A H 0.331198 0.485896 0.615341 0.048 Uiso 1 1 calc R U . . .
H11B H 0.306279 0.601144 0.713031 0.048 Uiso 1 1 calc R U . . .
C13 C 0.5902(5) 0.3597(3) 0.7823(2) 0.0477(6) Uani 1 1 d . . . . .
C6 C 0.7031(5) 0.9083(3) 0.84983(19) 0.0482(6) Uani 1 1 d . . . . .
H6A H 0.789637 1.010568 0.855450 0.058 Uiso 1 1 calc R U . . .
H6B H 0.524612 0.919326 0.829734 0.058 Uiso 1 1 calc R U . . .
C2 C 0.7985(6) 0.9203(3) 0.6031(2) 0.0536(7) Uani 1 1 d . . . . .
C8 C 0.6797(6) 0.6605(3) 0.9181(2) 0.0578(8) Uani 1 1 d . . . . .
H8A H 0.498676 0.644832 0.904318 0.069 Uiso 1 1 calc R U . . .
H8B H 0.748930 0.590457 0.971384 0.069 Uiso 1 1 calc R U . . .
C7 C 0.7621(6) 0.8295(3) 0.9546(2) 0.0600(8) Uani 1 1 d . . . . .
H7A H 0.667247 0.870116 1.006997 0.072 Uiso 1 1 calc R U . . .
H7B H 0.939274 0.841302 0.984666 0.072 Uiso 1 1 calc R U . . .
C3 C 1.0343(6) 0.9634(3) 0.6853(3) 0.0565(8) Uani 1 1 d . . . . .
H9 H 0.960(4) 0.606(3) 0.8321(18) 0.036(6) Uiso 1 1 d . . . . .
H2A H 0.833(5) 0.867(3) 0.540(2) 0.059(8) Uiso 1 1 d . . . . .
H3A H 1.022(6) 1.069(4) 0.719(2) 0.076(10) Uiso 1 1 d . . . . .
H3B H 1.187(6) 0.963(4) 0.652(2) 0.079(10) Uiso 1 1 d . . . . .
H2B H 0.698(5) 1.009(4) 0.586(2) 0.068(9) Uiso 1 1 d . . . . .
H15 H 0.750(7) 0.413(4) 0.605(3) 0.100(13) Uiso 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
O15 C10 1.418(3) . ?
O15 H15 0.89(4) . ?
F1 C13 1.337(3) . ?
F2 C13 1.342(3) . ?
F3 C13 1.334(3) . ?
O4 C5 1.427(3) . ?
O4 C3 1.435(3) . ?
O14 C12 1.235(3) . ?
N1 C12 1.338(3) . ?
N1 C5 1.465(3) . ?
N1 C2 1.462(3) . ?
C10 C9 1.532(3) . ?
C10 C11 1.529(3) . ?
C10 C13 1.529(3) . ?
C12 C11 1.506(3) . ?
C5 C9 1.558(3) . ?
C5 C6 1.529(3) . ?
C9 C8 1.537(3) . ?
C9 H9 0.98(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.517(4) . ?
C2 C3 1.519(4) . ?
C2 H2A 0.95(3) . ?
C2 H2B 0.97(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C7 1.523(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C3 H3A 0.99(3) . ?
C3 H3B 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
C10 O15 H15 109(2) . . ?
C5 O4 C3 106.19(18) . . ?
C12 N1 C5 125.99(19) . . ?
C12 N1 C2 121.7(2) . . ?
C2 N1 C5 109.71(19) . . ?
O15 C10 C9 106.51(18) . . ?
O15 C10 C11 110.70(18) . . ?
O15 C10 C13 107.31(19) . . ?
C11 C10 C9 110.60(18) . . ?
C13 C10 C9 111.40(18) . . ?
C13 C10 C11 110.22(19) . . ?
O14 C12 N1 121.0(2) . . ?
O14 C12 C11 122.8(2) . . ?
N1 C12 C11 116.26(19) . . ?
O4 C5 N1 102.28(18) . . ?
O4 C5 C9 109.50(18) . . ?
O4 C5 C6 111.35(19) . . ?
N1 C5 C9 115.76(18) . . ?
N1 C5 C6 113.10(18) . . ?
C6 C5 C9 104.97(19) . . ?
C10 C9 C5 112.48(18) . . ?
C10 C9 C8 117.9(2) . . ?
C10 C9 H9 105.6(13) . . ?
C5 C9 H9 105.9(14) . . ?
C8 C9 C5 105.0(2) . . ?
C8 C9 H9 109.3(13) . . ?
C10 C11 H11A 109.8 . . ?
C10 C11 H11B 109.8 . . ?
C12 C11 C10 109.32(18) . . ?
C12 C11 H11A 109.8 . . ?
C12 C11 H11B 109.8 . . ?
H11A C11 H11B 108.3 . . ?
F1 C13 F2 105.8(2) . . ?
F1 C13 C10 111.9(2) . . ?
F2 C13 C10 113.3(2) . . ?
F3 C13 F1 106.5(2) . . ?
F3 C13 F2 106.8(2) . . ?
F3 C13 C10 112.0(2) . . ?
C5 C6 H6A 110.9 . . ?
C5 C6 H6B 110.9 . . ?
H6A C6 H6B 108.9 . . ?
C7 C6 C5 104.20(19) . . ?
C7 C6 H6A 110.9 . . ?
C7 C6 H6B 110.9 . . ?
N1 C2 C3 102.4(2) . . ?
N1 C2 H2A 107.7(18) . . ?
N1 C2 H2B 109.7(18) . . ?
C3 C2 H2A 112.4(17) . . ?
C3 C2 H2B 112.9(18) . . ?
H2A C2 H2B 111(2) . . ?
C9 C8 H8A 111.1 . . ?
C9 C8 H8B 111.1 . . ?
H8A C8 H8B 109.1 . . ?
C7 C8 C9 103.3(2) . . ?
C7 C8 H8A 111.1 . . ?
C7 C8 H8B 111.1 . . ?
C6 C7 C8 101.4(2) . . ?
C6 C7 H7A 111.5 . . ?
C6 C7 H7B 111.5 . . ?
C8 C7 H7A 111.5 . . ?
C8 C7 H7B 111.5 . . ?
H7A C7 H7B 109.3 . . ?
O4 C3 C2 105.2(2) . . ?
O4 C3 H3A 113.7(18) . . ?
O4 C3 H3B 107.9(19) . . ?
C2 C3 H3A 109.2(17) . . ?
C2 C3 H3B 111.7(18) . . ?
H3A C3 H3B 109(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
O15 C10 C9 C5 76.9(2) . . . . ?
O15 C10 C9 C8 -160.7(2) . . . . ?
O15 C10 C11 C12 -54.9(2) . . . . ?
O15 C10 C13 F1 -50.7(3) . . . . ?
O15 C10 C13 F2 -170.17(18) . . . . ?
O15 C10 C13 F3 68.9(3) . . . . ?
O4 C5 C9 C10 -109.5(2) . . . . ?
O4 C5 C9 C8 121.0(2) . . . . ?
O4 C5 C6 C7 -92.3(2) . . . . ?
O14 C12 C11 C10 136.8(2) . . . . ?
N1 C12 C11 C10 -42.7(3) . . . . ?
N1 C5 C9 C10 5.4(3) . . . . ?
N1 C5 C9 C8 -124.1(2) . . . . ?
N1 C5 C6 C7 153.2(2) . . . . ?
N1 C2 C3 O4 17.8(3) . . . . ?
C10 C9 C8 C7 -154.3(2) . . . . ?
C12 N1 C5 O4 135.7(2) . . . . ?
C12 N1 C5 C9 16.8(3) . . . . ?
C12 N1 C5 C6 -104.4(3) . . . . ?
C12 N1 C2 C3 -157.6(2) . . . . ?
C5 O4 C3 C2 -35.4(3) . . . . ?
C5 N1 C12 O14 -176.6(2) . . . . ?
C5 N1 C12 C11 2.9(3) . . . . ?
C5 N1 C2 C3 5.2(3) . . . . ?
C5 C9 C8 C7 -28.1(3) . . . . ?
C5 C6 C7 C8 -43.7(3) . . . . ?
C9 C10 C11 C12 62.9(2) . . . . ?
C9 C10 C13 F1 -166.9(2) . . . . ?
C9 C10 C13 F2 73.6(3) . . . . ?
C9 C10 C13 F3 -47.4(3) . . . . ?
C9 C5 C6 C7 26.1(2) . . . . ?
C9 C8 C7 C6 44.3(3) . . . . ?
C11 C10 C9 C5 -43.5(3) . . . . ?
C11 C10 C9 C8 79.0(3) . . . . ?
C11 C10 C13 F1 70.0(3) . . . . ?
C11 C10 C13 F2 -49.6(3) . . . . ?
C11 C10 C13 F3 -170.5(2) . . . . ?
C13 C10 C9 C5 -166.4(2) . . . . ?
C13 C10 C9 C8 -44.0(3) . . . . ?
C13 C10 C11 C12 -173.49(19) . . . . ?
C6 C5 C9 C10 130.9(2) . . . . ?
C6 C5 C9 C8 1.4(2) . . . . ?
C2 N1 C12 O14 -16.7(4) . . . . ?
C2 N1 C12 C11 162.9(2) . . . . ?
C2 N1 C5 O4 -26.2(3) . . . . ?
C2 N1 C5 C9 -145.2(2) . . . . ?
C2 N1 C5 C6 93.7(3) . . . . ?
C3 O4 C5 N1 37.7(2) . . . . ?
C3 O4 C5 C9 161.0(2) . . . . ?
C3 O4 C5 C6 -83.4(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.134
_oxdiff_exptl_absorpt_empirical_full_min 0.857
####################################################################### 
# 
# 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_exp_792
_database_code_depnum_ccdc_archive 'CCDC 2107624'
loop_
_audit_author_name
_audit_author_address
'Pavel A. Slepukhin'
;Postovsky Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2021-09-04 deposited with the CCDC.	2021-10-28 downloaded from the CCDC.
;
_audit_creation_date             2020-06-19
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H19 F3 N2 O2'
_chemical_formula_sum            'C17 H19 F3 N2 O2'
_chemical_formula_weight         340.34
_chemical_melting_point          ?
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'
F F 0.0171 0.0103 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.7168(10)
_cell_length_b                   11.9298(13)
_cell_length_c                   12.1371(12)
_cell_angle_alpha                70.519(9)
_cell_angle_beta                 89.748(7)
_cell_angle_gamma                79.574(8)
_cell_volume                     1570.1(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1523
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25.3070
_cell_measurement_theta_min      3.7500
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.949
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69472
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.38a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0657
_diffrn_reflns_av_unetI/netI     0.1339
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12701
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.282
_diffrn_reflns_theta_min         3.543
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.5253
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -2.00  24.00   1.00   60.00    --   22.21  69.00 -42.00   26
  2  ω     19.00  47.00   1.00   60.00    --   22.21 -69.00-175.00   28
  3  ω    -46.00  45.00   1.00   60.00    --  -23.92  69.00 -42.00   91
  4  ω    -90.00   0.00   1.00   60.00    --  -23.92 -69.00-175.00   90
  5  ω    -25.00  64.00   1.00   60.00    --   22.21 -99.00  60.00   89
  6  ω    -48.00  23.00   1.00   60.00    --   22.21 -77.00  90.00   71
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0154011000
_diffrn_orient_matrix_UB_12      -0.0469028000
_diffrn_orient_matrix_UB_13      -0.0240776000
_diffrn_orient_matrix_UB_21      0.0454931000
_diffrn_orient_matrix_UB_22      0.0280249000
_diffrn_orient_matrix_UB_23      -0.0288192000
_diffrn_orient_matrix_UB_31      0.0386764000
_diffrn_orient_matrix_UB_32      -0.0337894000
_diffrn_orient_matrix_UB_33      0.0494616000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2835
_reflns_number_total             7528
_reflns_odcompleteness_completeness 96.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       0.0031(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   0.984
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     454
_refine_ls_number_reflns         7528
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1978
_refine_ls_R_factor_gt           0.0742
_refine_ls_restrained_S_all      0.984
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0740P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1604
_refine_ls_wR_factor_ref         0.2399
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Riding coordinates:
 N1(H1A)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C2A(H2AA,H2AB), C17A(H17C,H17D), C8(H8A,H8B), C2(H2A,H2B),
 C5A(H5AA,H5AB), C8A(H8AA,H8AB), C5(H5A,H5B), C7A(H7AA,H7AB), C7(H7A,H7B),
 C6A(H6AA,H6AB), C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C12A(H12A), C12(H12), C15(H15), C13A(H13A), C15A(H15A), C13(H13), C14(H14),
 C14A(H14A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.6408(3) 0.1522(3) 0.3521(3) 0.0535(8) Uani 1 1 d . . . . .
O3 O 1.1386(2) -0.0855(3) 0.4500(3) 0.0566(8) Uani 1 1 d . . . . .
N1A N 1.3483(3) -0.0176(3) 0.1572(3) 0.0430(8) Uani 1 1 d . . . . .
O4 O 1.1962(2) -0.1573(3) 0.1524(3) 0.0537(8) Uani 1 1 d . . . . .
F1 F 1.5061(2) 0.3572(2) 0.3048(3) 0.0717(8) Uani 1 1 d . . . . .
F2A F 1.1369(2) -0.3642(2) 0.1999(3) 0.0751(9) Uani 1 1 d . . . . .
F2 F 1.5994(2) 0.4552(2) 0.1665(3) 0.0738(9) Uani 1 1 d . . . . .
N2 N 1.7829(2) 0.0733(3) 0.1448(3) 0.0443(8) Uani 1 1 d . . . . .
N1 N 1.8444(3) 0.0081(3) 0.3437(3) 0.0480(9) Uani 1 1 d . . . . .
H1A H 1.885349 0.017213 0.397642 0.058 Uiso 1 1 d R U . . .
O2 O 1.6123(2) 0.0784(3) 0.0546(3) 0.0591(8) Uani 1 1 d . . . . .
N2A N 1.3062(2) -0.0778(3) 0.3557(3) 0.0421(8) Uani 1 1 d . . . . .
F3A F 1.2679(2) -0.4628(2) 0.3353(3) 0.0726(8) Uani 1 1 d . . . . .
F3 F 1.6749(2) 0.3859(2) 0.3419(3) 0.0815(9) Uani 1 1 d . . . . .
C9 C 1.8515(3) 0.1033(3) 0.2285(3) 0.0403(9) Uani 1 1 d . . . . .
F1A F 1.3157(2) -0.3894(2) 0.1587(3) 0.0760(8) Uani 1 1 d . . . . .
C16A C 1.3042(3) 0.1372(4) 0.2497(4) 0.0475(10) Uani 1 1 d . . . . .
C9A C 1.3875(3) -0.1096(3) 0.2728(3) 0.0410(9) Uani 1 1 d . . . . .
C4A C 1.3822(3) -0.2357(3) 0.2681(4) 0.0426(10) Uani 1 1 d . . . . .
C3A C 1.2553(3) -0.2474(3) 0.2554(4) 0.0407(9) Uani 1 1 d . . . . .
C1A C 1.2100(3) -0.1257(4) 0.3912(4) 0.0430(10) Uani 1 1 d . . . . .
C3 C 1.6680(3) 0.2403(3) 0.2491(4) 0.0422(9) Uani 1 1 d . . . . .
C1 C 1.6681(3) 0.1202(4) 0.1122(4) 0.0435(10) Uani 1 1 d . . . . .
C12A C 1.3250(3) 0.1953(4) 0.0420(4) 0.0501(11) Uani 1 1 d . . . . .
H12A H 1.342901 0.173943 -0.024011 0.060 Uiso 1 1 calc R U . . .
C4 C 1.7998(3) 0.2279(3) 0.2352(4) 0.0434(10) Uani 1 1 d . . . . .
C11 C 1.8664(3) -0.1131(3) 0.3482(4) 0.0456(10) Uani 1 1 d . . . . .
C16 C 1.8562(3) -0.1416(4) 0.2465(4) 0.0526(11) Uani 1 1 d . . . . .
C10A C 1.2438(4) -0.3655(4) 0.2382(4) 0.0542(11) Uani 1 1 d . . . . .
C10 C 1.6123(3) 0.3591(4) 0.2646(4) 0.0534(11) Uani 1 1 d . . . . .
C11A C 1.3274(3) 0.1051(3) 0.1502(4) 0.0436(10) Uani 1 1 d . . . . .
C17 C 1.8320(3) -0.0424(4) 0.1296(4) 0.0540(11) Uani 1 1 d . . . . .
H17A H 1.903496 -0.035683 0.089450 0.065 Uiso 1 1 calc R U . . .
H17B H 1.777673 -0.061939 0.081914 0.065 Uiso 1 1 calc R U . . .
C2A C 1.1929(3) -0.2346(4) 0.3622(4) 0.0464(10) Uani 1 1 d . . . . .
H2AA H 1.110379 -0.229762 0.348378 0.056 Uiso 1 1 calc R U . . .
H2AB H 1.220592 -0.306778 0.429112 0.056 Uiso 1 1 calc R U . . .
C17A C 1.3105(4) 0.0398(4) 0.3677(4) 0.0551(11) Uani 1 1 d . . . . .
H17C H 1.382140 0.033890 0.410827 0.066 Uiso 1 1 calc R U . . .
H17D H 1.246034 0.061365 0.411808 0.066 Uiso 1 1 calc R U . . .
C8 C 1.9788(3) 0.0968(4) 0.1979(4) 0.0527(11) Uani 1 1 d . . . . .
H8A H 2.023823 0.101896 0.262369 0.063 Uiso 1 1 calc R U . . .
H8B H 2.007856 0.018842 0.189467 0.063 Uiso 1 1 calc R U . . .
C2 C 1.6103(3) 0.2276(4) 0.1431(4) 0.0464(10) Uani 1 1 d . . . . .
H2A H 1.529964 0.221294 0.158178 0.056 Uiso 1 1 calc R U . . .
H2B H 1.610381 0.300380 0.076366 0.056 Uiso 1 1 calc R U . . .
C5A C 1.4502(3) -0.3391(4) 0.3738(4) 0.0540(12) Uani 1 1 d . . . . .
H5AA H 1.406718 -0.344792 0.443040 0.065 Uiso 1 1 calc R U . . .
H5AB H 1.455829 -0.415103 0.359390 0.065 Uiso 1 1 calc R U . . .
C12 C 1.8922(3) -0.2057(4) 0.4564(4) 0.0586(13) Uani 1 1 d . . . . .
H12 H 1.901096 -0.187193 0.524052 0.070 Uiso 1 1 calc R U . . .
C15 C 1.8703(3) -0.2619(4) 0.2555(5) 0.0666(14) Uani 1 1 d . . . . .
H15 H 1.864324 -0.281386 0.188003 0.080 Uiso 1 1 calc R U . . .
C8A C 1.5123(3) -0.1033(4) 0.3041(4) 0.0529(12) Uani 1 1 d . . . . .
H8AA H 1.559752 -0.107133 0.239307 0.063 Uiso 1 1 calc R U . . .
H8AB H 1.512121 -0.025706 0.313583 0.063 Uiso 1 1 calc R U . . .
C5 C 1.8298(3) 0.3317(4) 0.1302(4) 0.0575(12) Uani 1 1 d . . . . .
H5A H 1.783494 0.338265 0.061468 0.069 Uiso 1 1 calc R U . . .
H5B H 1.807559 0.407069 0.145845 0.069 Uiso 1 1 calc R U . . .
C7A C 1.5673(3) -0.2025(4) 0.4138(4) 0.0627(14) Uani 1 1 d . . . . .
H7AA H 1.645305 -0.192357 0.429107 0.075 Uiso 1 1 calc R U . . .
H7AB H 1.522109 -0.198753 0.480136 0.075 Uiso 1 1 calc R U . . .
C13A C 1.2963(4) 0.3162(4) 0.0310(5) 0.0661(14) Uani 1 1 d . . . . .
H13A H 1.293653 0.376051 -0.041967 0.079 Uiso 1 1 calc R U . . .
C15A C 1.2770(3) 0.2580(4) 0.2379(5) 0.0610(13) Uani 1 1 d . . . . .
H15A H 1.261875 0.280301 0.303744 0.073 Uiso 1 1 calc R U . . .
C7 C 1.9977(3) 0.1952(4) 0.0875(4) 0.0640(14) Uani 1 1 d . . . . .
H7A H 1.954339 0.190570 0.021688 0.077 Uiso 1 1 calc R U . . .
H7B H 2.079495 0.185176 0.071900 0.077 Uiso 1 1 calc R U . . .
C13 C 1.9044(4) -0.3255(4) 0.4623(6) 0.0744(18) Uani 1 1 d . . . . .
H13 H 1.920430 -0.387250 0.534418 0.089 Uiso 1 1 calc R U . . .
C14 C 1.8930(4) -0.3538(5) 0.3624(7) 0.0794(18) Uani 1 1 d . . . . .
H14 H 1.900588 -0.434133 0.366791 0.095 Uiso 1 1 calc R U . . .
C14A C 1.2719(4) 0.3468(4) 0.1288(6) 0.0730(16) Uani 1 1 d . . . . .
H14A H 1.251735 0.428017 0.122040 0.088 Uiso 1 1 calc R U . . .
C6A C 1.5715(3) -0.3220(4) 0.3978(5) 0.0695(16) Uani 1 1 d . . . . .
H6AA H 1.607264 -0.386553 0.467816 0.083 Uiso 1 1 calc R U . . .
H6AB H 1.618688 -0.326048 0.332866 0.083 Uiso 1 1 calc R U . . .
C6 C 1.9569(3) 0.3170(4) 0.1026(5) 0.0728(16) Uani 1 1 d . . . . .
H6A H 2.003288 0.322908 0.165703 0.087 Uiso 1 1 calc R U . . .
H6B H 1.967014 0.381355 0.031305 0.087 Uiso 1 1 calc R U . . .
H4 H 1.835(3) 0.224(3) 0.311(4) 0.045(11) Uiso 1 1 d . . . . .
H1AA H 1.391(3) -0.033(4) 0.104(4) 0.070(15) Uiso 1 1 d . . . . .
H1 H 1.691(4) 0.101(4) 0.369(4) 0.069(17) Uiso 1 1 d . . . . .
H4AA H 1.424(3) -0.238(3) 0.198(4) 0.058(12) Uiso 1 1 d . . . . .
H4A H 1.223(4) -0.081(5) 0.126(5) 0.11(2) Uiso 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 C3 1.418(4) . ?
O1 H1 0.74(4) . ?
O3 C1A 1.231(4) . ?
N1A C9A 1.477(5) . ?
N1A C11A 1.412(5) . ?
N1A H1AA 0.86(5) . ?
O4 C3A 1.429(4) . ?
O4 H4A 0.97(5) . ?
F1 C10 1.336(4) . ?
F2A C10A 1.334(5) . ?
F2 C10 1.336(5) . ?
N2 C9 1.469(5) . ?
N2 C1 1.366(4) . ?
N2 C17 1.467(5) . ?
N1 H1A 0.8600 . ?
N1 C9 1.492(5) . ?
N1 C11 1.405(5) . ?
O2 C1 1.234(5) . ?
N2A C9A 1.477(5) . ?
N2A C1A 1.360(4) . ?
N2A C17A 1.467(5) . ?
F3A C10A 1.337(5) . ?
F3 C10 1.346(5) . ?
C9 C4 1.529(5) . ?
C9 C8 1.530(5) . ?
F1A C10A 1.346(5) . ?
C16A C11A 1.396(6) . ?
C16A C17A 1.505(6) . ?
C16A C15A 1.377(6) . ?
C9A C4A 1.537(6) . ?
C9A C8A 1.533(5) . ?
C4A C3A 1.532(5) . ?
C4A C5A 1.549(5) . ?
C4A H4AA 0.99(4) . ?
C3A C10A 1.520(6) . ?
C3A C2A 1.523(6) . ?
C1A C2A 1.501(6) . ?
C3 C4 1.538(5) . ?
C3 C10 1.520(6) . ?
C3 C2 1.520(6) . ?
C1 C2 1.498(6) . ?
C12A H12A 0.9300 . ?
C12A C11A 1.390(5) . ?
C12A C13A 1.382(6) . ?
C4 C5 1.543(5) . ?
C4 H4 1.00(4) . ?
C11 C16 1.396(6) . ?
C11 C12 1.397(6) . ?
C16 C17 1.502(6) . ?
C16 C15 1.381(6) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C2A H2AA 0.9700 . ?
C2A H2AB 0.9700 . ?
C17A H17C 0.9700 . ?
C17A H17D 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C7 1.505(6) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C5A H5AA 0.9700 . ?
C5A H5AB 0.9700 . ?
C5A C6A 1.515(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.388(7) . ?
C15 H15 0.9300 . ?
C15 C14 1.380(7) . ?
C8A H8AA 0.9700 . ?
C8A H8AB 0.9700 . ?
C8A C7A 1.507(5) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.517(5) . ?
C7A H7AA 0.9700 . ?
C7A H7AB 0.9700 . ?
C7A C6A 1.494(7) . ?
C13A H13A 0.9300 . ?
C13A C14A 1.369(8) . ?
C15A H15A 0.9300 . ?
C15A C14A 1.386(7) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C6 1.517(7) . ?
C13 H13 0.9300 . ?
C13 C14 1.376(8) . ?
C14 H14 0.9300 . ?
C14A H14A 0.9300 . ?
C6A H6AA 0.9700 . ?
C6A H6AB 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 H1 107(4) . . ?
C9A N1A H1AA 110(3) . . ?
C11A N1A C9A 117.2(4) . . ?
C11A N1A H1AA 115(3) . . ?
C3A O4 H4A 116(3) . . ?
C1 N2 C9 125.1(3) . . ?
C1 N2 C17 117.7(3) . . ?
C17 N2 C9 113.8(3) . . ?
C9 N1 H1A 110.9 . . ?
C11 N1 H1A 110.9 . . ?
C11 N1 C9 117.6(3) . . ?
C1A N2A C9A 125.5(3) . . ?
C1A N2A C17A 117.3(3) . . ?
C17A N2A C9A 114.0(3) . . ?
N2 C9 N1 104.9(3) . . ?
N2 C9 C4 111.3(3) . . ?
N2 C9 C8 111.3(3) . . ?
N1 C9 C4 109.5(3) . . ?
N1 C9 C8 109.1(3) . . ?
C4 C9 C8 110.6(3) . . ?
C11A C16A C17A 119.7(4) . . ?
C15A C16A C11A 119.0(4) . . ?
C15A C16A C17A 121.3(4) . . ?
N1A C9A N2A 105.5(3) . . ?
N1A C9A C4A 109.2(3) . . ?
N1A C9A C8A 109.2(3) . . ?
N2A C9A C4A 111.3(3) . . ?
N2A C9A C8A 111.1(4) . . ?
C8A C9A C4A 110.3(3) . . ?
C9A C4A C5A 112.5(4) . . ?
C9A C4A H4AA 103(2) . . ?
C3A C4A C9A 109.9(3) . . ?
C3A C4A C5A 112.4(3) . . ?
C3A C4A H4AA 112(2) . . ?
C5A C4A H4AA 107(2) . . ?
O4 C3A C4A 111.8(3) . . ?
O4 C3A C10A 103.2(3) . . ?
O4 C3A C2A 109.0(3) . . ?
C10A C3A C4A 112.6(3) . . ?
C10A C3A C2A 110.8(3) . . ?
C2A C3A C4A 109.2(4) . . ?
O3 C1A N2A 122.2(4) . . ?
O3 C1A C2A 118.9(3) . . ?
N2A C1A C2A 118.8(3) . . ?
O1 C3 C4 112.3(3) . . ?
O1 C3 C10 103.0(3) . . ?
O1 C3 C2 109.2(3) . . ?
C10 C3 C4 113.3(3) . . ?
C10 C3 C2 109.9(3) . . ?
C2 C3 C4 109.0(3) . . ?
N2 C1 C2 119.3(4) . . ?
O2 C1 N2 121.2(4) . . ?
O2 C1 C2 119.5(3) . . ?
C11A C12A H12A 119.5 . . ?
C13A C12A H12A 119.5 . . ?
C13A C12A C11A 120.9(5) . . ?
C9 C4 C3 110.5(3) . . ?
C9 C4 C5 112.1(4) . . ?
C9 C4 H4 102(2) . . ?
C3 C4 C5 112.2(3) . . ?
C3 C4 H4 107(2) . . ?
C5 C4 H4 113(2) . . ?
C16 C11 N1 120.5(4) . . ?
C16 C11 C12 119.9(4) . . ?
C12 C11 N1 119.4(4) . . ?
C11 C16 C17 120.1(4) . . ?
C15 C16 C11 118.9(5) . . ?
C15 C16 C17 121.1(5) . . ?
F2A C10A F3A 105.5(3) . . ?
F2A C10A F1A 106.2(4) . . ?
F2A C10A C3A 112.7(3) . . ?
F3A C10A F1A 106.0(3) . . ?
F3A C10A C3A 114.2(4) . . ?
F1A C10A C3A 111.7(3) . . ?
F1 C10 F3 106.0(4) . . ?
F1 C10 C3 112.7(3) . . ?
F2 C10 F1 105.4(3) . . ?
F2 C10 F3 105.8(4) . . ?
F2 C10 C3 114.4(4) . . ?
F3 C10 C3 111.9(3) . . ?
C16A C11A N1A 120.9(4) . . ?
C12A C11A N1A 119.6(4) . . ?
C12A C11A C16A 119.5(4) . . ?
N2 C17 C16 110.3(4) . . ?
N2 C17 H17A 109.6 . . ?
N2 C17 H17B 109.6 . . ?
C16 C17 H17A 109.6 . . ?
C16 C17 H17B 109.6 . . ?
H17A C17 H17B 108.1 . . ?
C3A C2A H2AA 108.8 . . ?
C3A C2A H2AB 108.8 . . ?
C1A C2A C3A 113.8(3) . . ?
C1A C2A H2AA 108.8 . . ?
C1A C2A H2AB 108.8 . . ?
H2AA C2A H2AB 107.7 . . ?
N2A C17A C16A 111.1(4) . . ?
N2A C17A H17C 109.4 . . ?
N2A C17A H17D 109.4 . . ?
C16A C17A H17C 109.4 . . ?
C16A C17A H17D 109.4 . . ?
H17C C17A H17D 108.0 . . ?
C9 C8 H8A 108.8 . . ?
C9 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
C7 C8 C9 113.9(3) . . ?
C7 C8 H8A 108.8 . . ?
C7 C8 H8B 108.8 . . ?
C3 C2 H2A 108.8 . . ?
C3 C2 H2B 108.8 . . ?
C1 C2 C3 113.9(3) . . ?
C1 C2 H2A 108.8 . . ?
C1 C2 H2B 108.8 . . ?
H2A C2 H2B 107.7 . . ?
C4A C5A H5AA 108.8 . . ?
C4A C5A H5AB 108.8 . . ?
H5AA C5A H5AB 107.7 . . ?
C6A C5A C4A 113.7(3) . . ?
C6A C5A H5AA 108.8 . . ?
C6A C5A H5AB 108.8 . . ?
C11 C12 H12 120.2 . . ?
C13 C12 C11 119.6(5) . . ?
C13 C12 H12 120.2 . . ?
C16 C15 H15 119.2 . . ?
C14 C15 C16 121.6(6) . . ?
C14 C15 H15 119.2 . . ?
C9A C8A H8AA 108.7 . . ?
C9A C8A H8AB 108.7 . . ?
H8AA C8A H8AB 107.6 . . ?
C7A C8A C9A 114.3(3) . . ?
C7A C8A H8AA 108.7 . . ?
C7A C8A H8AB 108.7 . . ?
C4 C5 H5A 108.6 . . ?
C4 C5 H5B 108.6 . . ?
H5A C5 H5B 107.5 . . ?
C6 C5 C4 114.8(3) . . ?
C6 C5 H5A 108.6 . . ?
C6 C5 H5B 108.6 . . ?
C8A C7A H7AA 109.9 . . ?
C8A C7A H7AB 109.9 . . ?
H7AA C7A H7AB 108.3 . . ?
C6A C7A C8A 108.8(4) . . ?
C6A C7A H7AA 109.9 . . ?
C6A C7A H7AB 109.9 . . ?
C12A C13A H13A 120.4 . . ?
C14A C13A C12A 119.2(5) . . ?
C14A C13A H13A 120.4 . . ?
C16A C15A H15A 119.6 . . ?
C16A C15A C14A 120.7(5) . . ?
C14A C15A H15A 119.6 . . ?
C8 C7 H7A 109.9 . . ?
C8 C7 H7B 109.9 . . ?
C8 C7 C6 108.8(4) . . ?
H7A C7 H7B 108.3 . . ?
C6 C7 H7A 109.9 . . ?
C6 C7 H7B 109.9 . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.5(5) . . ?
C14 C13 H13 119.7 . . ?
C15 C14 H14 120.3 . . ?
C13 C14 C15 119.4(5) . . ?
C13 C14 H14 120.3 . . ?
C13A C14A C15A 120.6(5) . . ?
C13A C14A H14A 119.7 . . ?
C15A C14A H14A 119.7 . . ?
C5A C6A H6AA 109.5 . . ?
C5A C6A H6AB 109.5 . . ?
C7A C6A C5A 110.6(3) . . ?
C7A C6A H6AA 109.5 . . ?
C7A C6A H6AB 109.5 . . ?
H6AA C6A H6AB 108.1 . . ?
C5 C6 C7 110.1(4) . . ?
C5 C6 H6A 109.6 . . ?
C5 C6 H6B 109.6 . . ?
C7 C6 H6A 109.6 . . ?
C7 C6 H6B 109.6 . . ?
H6A C6 H6B 108.1 . . ?

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
O1 C3 C4 C9 60.0(5) . . . . ?
O1 C3 C4 C5 -174.1(4) . . . . ?
O1 C3 C10 F1 -43.1(5) . . . . ?
O1 C3 C10 F2 -163.4(3) . . . . ?
O1 C3 C10 F3 76.3(4) . . . . ?
O1 C3 C2 C1 -74.4(4) . . . . ?
O3 C1A C2A C3A 158.0(3) . . . . ?
N1A C9A C4A C3A -68.6(4) . . . . ?
N1A C9A C4A C5A 165.5(3) . . . . ?
N1A C9A C8A C7A -173.3(4) . . . . ?
O4 C3A C10A F2A -44.4(4) . . . . ?
O4 C3A C10A F3A -164.7(3) . . . . ?
O4 C3A C10A F1A 75.0(4) . . . . ?
O4 C3A C2A C1A -72.5(4) . . . . ?
N2 C9 C4 C3 48.1(4) . . . . ?
N2 C9 C4 C5 -77.9(4) . . . . ?
N2 C9 C8 C7 69.2(5) . . . . ?
N2 C1 C2 C3 -24.9(5) . . . . ?
N1 C9 C4 C3 -67.5(4) . . . . ?
N1 C9 C4 C5 166.6(3) . . . . ?
N1 C9 C8 C7 -175.5(4) . . . . ?
N1 C11 C16 C17 5.4(5) . . . . ?
N1 C11 C16 C15 -175.4(3) . . . . ?
N1 C11 C12 C13 174.6(3) . . . . ?
O2 C1 C2 C3 157.5(3) . . . . ?
N2A C9A C4A C3A 47.6(4) . . . . ?
N2A C9A C4A C5A -78.4(4) . . . . ?
N2A C9A C8A C7A 70.7(4) . . . . ?
N2A C1A C2A C3A -24.6(5) . . . . ?
C9 N2 C1 O2 -169.7(3) . . . . ?
C9 N2 C1 C2 12.8(6) . . . . ?
C9 N2 C17 C16 51.6(4) . . . . ?
C9 N1 C11 C16 -21.1(5) . . . . ?
C9 N1 C11 C12 162.6(3) . . . . ?
C9 C4 C5 C6 -47.9(5) . . . . ?
C9 C8 C7 C6 60.9(5) . . . . ?
C16A C15A C14A C13A -1.4(7) . . . . ?
C9A N1A C11A C16A -22.1(5) . . . . ?
C9A N1A C11A C12A 160.7(3) . . . . ?
C9A N2A C1A O3 -171.5(3) . . . . ?
C9A N2A C1A C2A 11.2(5) . . . . ?
C9A N2A C17A C16A 48.8(4) . . . . ?
C9A C4A C3A O4 58.7(4) . . . . ?
C9A C4A C3A C10A 174.3(4) . . . . ?
C9A C4A C3A C2A -62.1(4) . . . . ?
C9A C4A C5A C6A -48.3(5) . . . . ?
C9A C8A C7A C6A 60.5(5) . . . . ?
C4A C9A C8A C7A -53.2(5) . . . . ?
C4A C3A C10A F2A -165.1(3) . . . . ?
C4A C3A C10A F3A 74.6(4) . . . . ?
C4A C3A C10A F1A -45.7(5) . . . . ?
C4A C3A C2A C1A 49.9(4) . . . . ?
C4A C5A C6A C7A 55.4(6) . . . . ?
C3A C4A C5A C6A -172.9(4) . . . . ?
C1A N2A C9A N1A 95.3(4) . . . . ?
C1A N2A C9A C4A -23.1(5) . . . . ?
C1A N2A C9A C8A -146.4(3) . . . . ?
C1A N2A C17A C16A -112.2(4) . . . . ?
C3 C4 C5 C6 -173.0(4) . . . . ?
C1 N2 C9 N1 93.8(4) . . . . ?
C1 N2 C9 C4 -24.6(5) . . . . ?
C1 N2 C9 C8 -148.4(3) . . . . ?
C1 N2 C17 C16 -108.7(4) . . . . ?
C12A C13A C14A C15A 0.7(7) . . . . ?
C4 C9 C8 C7 -55.0(5) . . . . ?
C4 C3 C10 F1 -164.6(4) . . . . ?
C4 C3 C10 F2 75.1(5) . . . . ?
C4 C3 C10 F3 -45.3(5) . . . . ?
C4 C3 C2 C1 48.7(4) . . . . ?
C4 C5 C6 C7 53.6(6) . . . . ?
C11 N1 C9 N2 48.2(4) . . . . ?
C11 N1 C9 C4 167.8(3) . . . . ?
C11 N1 C9 C8 -71.0(4) . . . . ?
C11 C16 C17 N2 -19.7(5) . . . . ?
C11 C16 C15 C14 0.6(6) . . . . ?
C11 C12 C13 C14 0.9(6) . . . . ?
C16 C11 C12 C13 -1.7(5) . . . . ?
C16 C15 C14 C13 -1.4(7) . . . . ?
C10A C3A C2A C1A 174.6(3) . . . . ?
C10 C3 C4 C9 176.1(3) . . . . ?
C10 C3 C4 C5 -58.0(5) . . . . ?
C10 C3 C2 C1 173.4(3) . . . . ?
C11A N1A C9A N2A 49.2(4) . . . . ?
C11A N1A C9A C4A 169.0(3) . . . . ?
C11A N1A C9A C8A -70.3(4) . . . . ?
C11A C16A C17A N2A -17.5(5) . . . . ?
C11A C16A C15A C14A 0.4(6) . . . . ?
C11A C12A C13A C14A 1.1(6) . . . . ?
C17 N2 C9 N1 -64.9(4) . . . . ?
C17 N2 C9 C4 176.8(3) . . . . ?
C17 N2 C9 C8 52.9(4) . . . . ?
C17 N2 C1 O2 -11.7(6) . . . . ?
C17 N2 C1 C2 170.7(3) . . . . ?
C17 C16 C15 C14 179.8(4) . . . . ?
C2A C3A C10A F2A 72.2(5) . . . . ?
C2A C3A C10A F3A -48.1(4) . . . . ?
C2A C3A C10A F1A -168.4(3) . . . . ?
C17A N2A C9A N1A -63.9(4) . . . . ?
C17A N2A C9A C4A 177.7(3) . . . . ?
C17A N2A C9A C8A 54.3(4) . . . . ?
C17A N2A C1A O3 -12.8(6) . . . . ?
C17A N2A C1A C2A 169.8(3) . . . . ?
C17A C16A C11A N1A 4.8(5) . . . . ?
C17A C16A C11A C12A -178.0(3) . . . . ?
C17A C16A C15A C14A 179.7(4) . . . . ?
C8 C9 C4 C3 172.3(3) . . . . ?
C8 C9 C4 C5 46.3(5) . . . . ?
C8 C7 C6 C5 -58.1(5) . . . . ?
C2 C3 C4 C9 -61.2(4) . . . . ?
C2 C3 C4 C5 64.7(4) . . . . ?
C2 C3 C10 F1 73.2(5) . . . . ?
C2 C3 C10 F2 -47.2(5) . . . . ?
C2 C3 C10 F3 -167.5(3) . . . . ?
C5A C4A C3A O4 -175.3(3) . . . . ?
C5A C4A C3A C10A -59.6(5) . . . . ?
C5A C4A C3A C2A 64.0(4) . . . . ?
C12 C11 C16 C17 -178.2(3) . . . . ?
C12 C11 C16 C15 1.0(5) . . . . ?
C12 C13 C14 C15 0.6(7) . . . . ?
C15 C16 C17 N2 161.1(3) . . . . ?
C8A C9A C4A C3A 171.4(3) . . . . ?
C8A C9A C4A C5A 45.4(4) . . . . ?
C8A C7A C6A C5A -59.6(5) . . . . ?
C13A C12A C11A N1A 175.2(3) . . . . ?
C13A C12A C11A C16A -2.1(6) . . . . ?
C15A C16A C11A N1A -175.9(3) . . . . ?
C15A C16A C11A C12A 1.3(5) . . . . ?
C15A C16A C17A N2A 163.2(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.372
_oxdiff_exptl_absorpt_empirical_full_min 0.826
####################################################################### 
# 
# 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_exp_815
_database_code_depnum_ccdc_archive 'CCDC 2107627'
loop_
_audit_author_name
_audit_author_address
'Pavel A. Slepukhin'
;Postovsky Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2021-09-04 deposited with the CCDC.	2021-10-28 downloaded from the CCDC.
;
_audit_creation_date             2020-08-04
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.16 svn.r6f6c53a7 for OlexSys, GUI svn.r6139)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H16 F3 N O3'
_chemical_formula_sum            'C12 H16 F3 N O3'
_chemical_formula_weight         279.26
_chemical_melting_point          ?
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'
F F 0.0171 0.0103 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   17.7173(16)
_cell_length_b                   5.9455(8)
_cell_length_c                   24.594(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.644(10)
_cell_angle_gamma                90
_cell_volume                     2537.3(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1476
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      26.0000
_cell_measurement_theta_min      4.1260
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.939
_exptl_absorpt_coefficient_mu    0.132
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50678
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.38a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plank
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0708
_diffrn_reflns_av_unetI/netI     0.0655
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            7899
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.354
_diffrn_reflns_theta_min         3.622
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.5253
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -8.00  92.00   1.00   60.00    --   22.21  77.00 150.00  100
  2  ω     -8.00  92.00   1.00   60.00    --   22.21  77.00 -90.00  100
  3  ω     17.00  46.00   1.00   60.00    --  -23.92  77.00  30.00   29
  4  ω    -39.00  16.00   1.00   60.00    --  -23.92  77.00  30.00   55
  5  ω      9.00  45.00   1.00   60.00    --  -23.92  77.00   0.00   36
  6  ω    -47.00   8.00   1.00   60.00    --  -23.92  77.00   0.00   55
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0032960000
_diffrn_orient_matrix_UB_12      0.0236950000
_diffrn_orient_matrix_UB_13      -0.0286523000
_diffrn_orient_matrix_UB_21      -0.0382206000
_diffrn_orient_matrix_UB_22      -0.0421175000
_diffrn_orient_matrix_UB_23      -0.0054059000
_diffrn_orient_matrix_UB_31      -0.0140476000
_diffrn_orient_matrix_UB_32      0.1090749000
_diffrn_orient_matrix_UB_33      0.0041968000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1586
_reflns_number_total             2593
_reflns_odcompleteness_completeness 82.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2593
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1039
_refine_ls_R_factor_gt           0.0642
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0840P)²+0.1538P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1575
_refine_ls_wR_factor_ref         0.1922
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B),
 C12(H12A,H12B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.66295(12) 0.0642(4) 0.41394(10) 0.0889(7) Uani 1 1 d . . . . .
F2 F 0.69563(11) 0.3891(4) 0.39033(10) 0.0855(7) Uani 1 1 d . . . . .
F3 F 0.62624(10) 0.1732(4) 0.33079(9) 0.0838(7) Uani 1 1 d . . . . .
O1 O 0.74660(12) -0.1525(4) 0.34864(9) 0.0573(6) Uani 1 1 d . . . . .
O2 O 0.85669(12) 0.2375(4) 0.24362(9) 0.0728(8) Uani 1 1 d . . . . .
O4 O 0.96586(11) 0.1581(4) 0.41527(8) 0.0553(6) Uani 1 1 d . . . . .
N1 N 0.90460(12) 0.0974(5) 0.32742(9) 0.0538(7) Uani 1 1 d . . . . .
C2 C 0.98508(17) 0.1292(8) 0.32327(14) 0.0813(12) Uani 1 1 d . . . . .
H2A H 0.991021 0.259250 0.300689 0.098 Uiso 1 1 calc R U . . .
H2B H 1.005170 -0.002652 0.307781 0.098 Uiso 1 1 calc R U . . .
C3 C 1.02445(18) 0.1651(8) 0.38319(15) 0.0841(12) Uani 1 1 d . . . . .
H3A H 1.062285 0.048022 0.395112 0.101 Uiso 1 1 calc R U . . .
H3B H 1.050429 0.309576 0.387538 0.101 Uiso 1 1 calc R U . . .
C5 C 0.90242(14) 0.0356(5) 0.38477(10) 0.0441(7) Uani 1 1 d . . . . .
C6 C 0.91587(19) -0.2153(5) 0.39379(13) 0.0595(8) Uani 1 1 d . . . . .
H6A H 0.964890 -0.256030 0.384722 0.071 Uiso 1 1 calc R U . . .
H6B H 0.875644 -0.298001 0.369230 0.071 Uiso 1 1 calc R U . . .
C7 C 0.9160(2) -0.2803(6) 0.45420(13) 0.0718(11) Uani 1 1 d . . . . .
H7A H 0.921835 -0.442007 0.458442 0.086 Uiso 1 1 calc R U . . .
H7B H 0.959482 -0.209568 0.478498 0.086 Uiso 1 1 calc R U . . .
C8 C 0.8425(2) -0.2080(6) 0.47059(14) 0.0733(11) Uani 1 1 d . . . . .
H8A H 0.844628 -0.245198 0.509263 0.088 Uiso 1 1 calc R U . . .
H8B H 0.799445 -0.288198 0.448351 0.088 Uiso 1 1 calc R U . . .
C9 C 0.83061(18) 0.0419(6) 0.46223(12) 0.0614(9) Uani 1 1 d . . . . .
H9A H 0.871203 0.120258 0.487546 0.074 Uiso 1 1 calc R U . . .
H9B H 0.781985 0.082772 0.471921 0.074 Uiso 1 1 calc R U . . .
C10 C 0.83014(15) 0.1233(5) 0.40278(10) 0.0435(6) Uani 1 1 d . . . . .
H10 H 0.835786 0.287205 0.405158 0.052 Uiso 1 1 calc R U . . .
C11 C 0.75839(15) 0.0786(5) 0.35745(11) 0.0443(7) Uani 1 1 d . . . . .
C12 C 0.76877(15) 0.1984(5) 0.30429(12) 0.0495(7) Uani 1 1 d . . . . .
H12A H 0.730521 0.140528 0.273598 0.059 Uiso 1 1 calc R U . . .
H12B H 0.758120 0.357094 0.307961 0.059 Uiso 1 1 calc R U . . .
C13 C 0.84688(16) 0.1761(5) 0.28959(11) 0.0496(7) Uani 1 1 d . . . . .
C16 C 0.68632(18) 0.1757(6) 0.37343(14) 0.0602(8) Uani 1 1 d . . . . .
H1 H 0.710(3) -0.203(7) 0.3146(19) 0.108(14) Uiso 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
F1 C16 1.331(4) . ?
F2 C16 1.335(4) . ?
F3 C16 1.335(4) . ?
O1 C11 1.400(3) . ?
O1 H1 0.99(5) . ?
O2 C13 1.234(3) . ?
O4 C3 1.426(4) . ?
O4 C5 1.420(3) . ?
N1 C2 1.462(4) . ?
N1 C5 1.465(3) . ?
N1 C13 1.322(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.513(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C5 C6 1.520(4) . ?
C5 C10 1.529(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.534(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.502(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.509(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.539(4) . ?
C10 H10 0.9800 . ?
C10 C11 1.536(4) . ?
C11 C12 1.532(4) . ?
C11 C16 1.523(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.505(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
C11 O1 H1 118(2) . . ?
C5 O4 C3 108.1(2) . . ?
C2 N1 C5 108.4(2) . . ?
C13 N1 C2 122.1(3) . . ?
C13 N1 C5 126.8(2) . . ?
N1 C2 H2A 111.3 . . ?
N1 C2 H2B 111.3 . . ?
N1 C2 C3 102.4(2) . . ?
H2A C2 H2B 109.2 . . ?
C3 C2 H2A 111.3 . . ?
C3 C2 H2B 111.3 . . ?
O4 C3 C2 106.9(3) . . ?
O4 C3 H3A 110.3 . . ?
O4 C3 H3B 110.3 . . ?
C2 C3 H3A 110.3 . . ?
C2 C3 H3B 110.3 . . ?
H3A C3 H3B 108.6 . . ?
O4 C5 N1 102.0(2) . . ?
O4 C5 C6 110.0(2) . . ?
O4 C5 C10 107.0(2) . . ?
N1 C5 C6 110.6(2) . . ?
N1 C5 C10 112.3(2) . . ?
C6 C5 C10 114.1(2) . . ?
C5 C6 H6A 109.4 . . ?
C5 C6 H6B 109.4 . . ?
C5 C6 C7 111.0(3) . . ?
H6A C6 H6B 108.0 . . ?
C7 C6 H6A 109.4 . . ?
C7 C6 H6B 109.4 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
C8 C7 C6 110.8(3) . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 C9 110.5(3) . . ?
H8A C8 H8B 108.1 . . ?
C9 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
C8 C9 H9A 108.7 . . ?
C8 C9 H9B 108.7 . . ?
C8 C9 C10 114.4(3) . . ?
H9A C9 H9B 107.6 . . ?
C10 C9 H9A 108.7 . . ?
C10 C9 H9B 108.7 . . ?
C5 C10 C9 108.9(2) . . ?
C5 C10 H10 106.0 . . ?
C5 C10 C11 110.5(2) . . ?
C9 C10 H10 106.0 . . ?
C11 C10 C9 118.7(2) . . ?
C11 C10 H10 106.0 . . ?
O1 C11 C10 111.0(2) . . ?
O1 C11 C12 111.4(2) . . ?
O1 C11 C16 107.8(2) . . ?
C12 C11 C10 108.3(2) . . ?
C16 C11 C10 111.2(2) . . ?
C16 C11 C12 107.2(2) . . ?
C11 C12 H12A 108.3 . . ?
C11 C12 H12B 108.3 . . ?
H12A C12 H12B 107.4 . . ?
C13 C12 C11 116.0(2) . . ?
C13 C12 H12A 108.3 . . ?
C13 C12 H12B 108.3 . . ?
O2 C13 N1 121.2(3) . . ?
O2 C13 C12 120.0(2) . . ?
N1 C13 C12 118.7(2) . . ?
F1 C16 F2 106.2(3) . . ?
F1 C16 F3 105.3(2) . . ?
F1 C16 C11 114.1(3) . . ?
F2 C16 F3 106.5(3) . . ?
F2 C16 C11 112.5(2) . . ?
F3 C16 C11 111.7(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
O1 C11 C12 C13 -78.4(3) . . . . ?
O1 C11 C16 F1 50.1(3) . . . . ?
O1 C11 C16 F2 171.2(3) . . . . ?
O1 C11 C16 F3 -69.1(3) . . . . ?
O4 C5 C6 C7 66.4(3) . . . . ?
O4 C5 C10 C9 -71.5(3) . . . . ?
O4 C5 C10 C11 156.5(2) . . . . ?
N1 C2 C3 O4 -1.6(5) . . . . ?
N1 C5 C6 C7 178.3(2) . . . . ?
N1 C5 C10 C9 177.4(2) . . . . ?
N1 C5 C10 C11 45.3(3) . . . . ?
C2 N1 C5 O4 33.5(3) . . . . ?
C2 N1 C5 C6 -83.5(3) . . . . ?
C2 N1 C5 C10 147.7(3) . . . . ?
C2 N1 C13 O2 15.5(5) . . . . ?
C2 N1 C13 C12 -162.1(3) . . . . ?
C3 O4 C5 N1 -34.3(3) . . . . ?
C3 O4 C5 C6 83.2(3) . . . . ?
C3 O4 C5 C10 -152.4(3) . . . . ?
C5 O4 C3 C2 23.0(4) . . . . ?
C5 N1 C2 C3 -19.6(4) . . . . ?
C5 N1 C13 O2 174.8(3) . . . . ?
C5 N1 C13 C12 -2.8(5) . . . . ?
C5 C6 C7 C8 56.0(4) . . . . ?
C5 C10 C11 O1 63.0(3) . . . . ?
C5 C10 C11 C12 -59.6(3) . . . . ?
C5 C10 C11 C16 -177.1(2) . . . . ?
C6 C5 C10 C9 50.4(3) . . . . ?
C6 C5 C10 C11 -81.6(3) . . . . ?
C6 C7 C8 C9 -56.9(4) . . . . ?
C7 C8 C9 C10 56.5(4) . . . . ?
C8 C9 C10 C5 -51.8(3) . . . . ?
C8 C9 C10 C11 75.7(4) . . . . ?
C9 C10 C11 O1 -63.8(3) . . . . ?
C9 C10 C11 C12 173.7(3) . . . . ?
C9 C10 C11 C16 56.2(4) . . . . ?
C10 C5 C6 C7 -53.8(3) . . . . ?
C10 C11 C12 C13 43.9(3) . . . . ?
C10 C11 C16 F1 -71.7(3) . . . . ?
C10 C11 C16 F2 49.3(4) . . . . ?
C10 C11 C16 F3 169.1(2) . . . . ?
C11 C12 C13 O2 169.0(3) . . . . ?
C11 C12 C13 N1 -13.3(4) . . . . ?
C12 C11 C16 F1 170.1(3) . . . . ?
C12 C11 C16 F2 -68.9(3) . . . . ?
C12 C11 C16 F3 50.9(3) . . . . ?
C13 N1 C2 C3 143.0(3) . . . . ?
C13 N1 C5 O4 -128.1(3) . . . . ?
C13 N1 C5 C6 114.9(3) . . . . ?
C13 N1 C5 C10 -13.9(4) . . . . ?
C16 C11 C12 C13 163.9(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.401
_oxdiff_exptl_absorpt_empirical_full_min 0.733
####################################################################### 
# 
# 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_exp_816
_database_code_depnum_ccdc_archive 'CCDC 2107622'
loop_
_audit_author_name
_audit_author_address
'Pavel A. Slepukhin'
;Postovsky Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2021-09-04 deposited with the CCDC.	2021-10-28 downloaded from the CCDC.
;
_audit_creation_date             2020-08-04
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H17 F3 N2 O2'
_chemical_formula_sum            'C12 H17 F3 N2 O2'
_chemical_formula_weight         278.27
_chemical_melting_point          ?
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'
F F 0.0171 0.0103 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.8729(14)
_cell_length_b                   12.6636(14)
_cell_length_c                   15.6817(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2556.4(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1358
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.0710
_cell_measurement_theta_min      4.4360
_shelx_estimated_absorpt_T_max   0.965
_shelx_estimated_absorpt_T_min   0.940
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74621
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.38a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.28
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0454
_diffrn_reflns_av_unetI/netI     0.0553
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.851
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            8484
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.851
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.999
_diffrn_reflns_theta_min         3.470
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.5253
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.851
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -90.00 -59.00   1.00   30.00    --  -24.08 -73.00  84.00   31
  2  ω    -35.00  17.00   1.00   30.00    --  -24.08  49.00  28.00   52
  3  ω     36.00  61.00   1.00   30.00    --   22.36 178.00   0.00   25
  4  ω     35.00  93.00   1.00   30.00    --   22.36 178.00 -90.00   58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0319862000
_diffrn_orient_matrix_UB_12      0.0389387000
_diffrn_orient_matrix_UB_13      0.0191236000
_diffrn_orient_matrix_UB_21      0.0443752000
_diffrn_orient_matrix_UB_22      -0.0229554000
_diffrn_orient_matrix_UB_23      -0.0193801000
_diffrn_orient_matrix_UB_31      -0.0068150000
_diffrn_orient_matrix_UB_32      0.0330089000
_diffrn_orient_matrix_UB_33      -0.0361338000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1684
_reflns_number_total             3475
_reflns_odcompleteness_completeness 98.99
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.0023(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         3475
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1237
_refine_ls_R_factor_gt           0.0584
_refine_ls_restrained_S_all      1.008
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1554
_refine_ls_wR_factor_ref         0.2194
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All C(H,H,H,H) groups
2. Others
 Fixed Sof: H6AA(0.6) H6AB(0.6) H6BC(0.4) H6BD(0.4) H8AA(0.6) H8AB(0.6)
 H8BC(0.4) H8BD(0.4) C7(0.6) H7A(0.6) H7B(0.6) C7A(0.4) H7AA(0.4) H7AB(0.4)
3.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C2(H2A,H2B), C6(H6AA,H6AB), C6(H6BC,H6BD), C4(H4A,H4B),
 C8(H8AA,H8AB), C8(H8BC,H8BD), C3(H3A,H3B), C7(H7A,H7B), C7A(H7AA,H7AB)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.11154(13) 0.35365(13) 0.07462(10) 0.0602(5) Uani 1 1 d . . . . .
N2 N 0.14842(14) 0.38387(14) -0.12535(11) 0.0533(5) Uani 1 1 d . . . . .
O2 O 0.05196(14) 0.53208(12) -0.12715(11) 0.0677(5) Uani 1 1 d . . . . .
C12 C 0.11600(17) 0.47442(16) -0.09087(15) 0.0503(5) Uani 1 1 d . . . . .
N1 N 0.16201(17) 0.20664(15) -0.06879(15) 0.0591(6) Uani 1 1 d . . . . .
C5 C 0.21913(18) 0.30396(17) -0.08474(14) 0.0525(6) Uani 1 1 d . . . . .
F1 F 0.18015(17) 0.50848(16) 0.17981(11) 0.1035(7) Uani 1 1 d . . . . .
F3 F 0.32442(17) 0.52916(18) 0.11301(12) 0.1108(7) Uani 1 1 d . . . . .
C10 C 0.19655(17) 0.41744(18) 0.04848(14) 0.0557(6) Uani 1 1 d . . . . .
F2 F 0.29061(16) 0.38225(19) 0.17607(10) 0.1119(7) Uani 1 1 d . . . . .
C9 C 0.26895(18) 0.3464(2) -0.00166(15) 0.0564(6) Uani 1 1 d . . . . .
C11 C 0.16052(18) 0.50922(16) -0.00653(15) 0.0546(6) Uani 1 1 d . . . . .
H11A H 0.108203 0.548954 0.024320 0.066 Uiso 1 1 calc R U . . .
H11B H 0.218887 0.555926 -0.016931 0.066 Uiso 1 1 calc R U . . .
C2 C 0.0966(2) 0.34599(19) -0.20335(16) 0.0684(7) Uani 1 1 d . . . . .
H2A H 0.148224 0.330448 -0.246649 0.082 Uiso 1 1 calc R U . . .
H2B H 0.050855 0.400454 -0.225252 0.082 Uiso 1 1 calc R U . . .
C6 C 0.3135(2) 0.2845(2) -0.14415(19) 0.0709(7) Uani 1 1 d . . . . .
H6AA H 0.316373 0.211063 -0.161640 0.085 Uiso 0.6 1 calc R U P A 1
H6AB H 0.308990 0.328463 -0.194655 0.085 Uiso 0.6 1 calc R U P A 1
H6BC H 0.342546 0.215013 -0.133680 0.085 Uiso 0.4 1 calc R U P B 2
H6BD H 0.292061 0.288295 -0.203378 0.085 Uiso 0.4 1 calc R U P B 2
C1 C 0.2486(3) 0.4592(3) 0.12922(18) 0.0783(8) Uani 1 1 d . . . . .
C4 C 0.1038(2) 0.16657(18) -0.14248(18) 0.0718(8) Uani 1 1 d . . . . .
H4A H 0.061505 0.107356 -0.124281 0.086 Uiso 1 1 calc R U . . .
H4B H 0.152757 0.140663 -0.184623 0.086 Uiso 1 1 calc R U . . .
C8 C 0.37398(18) 0.3914(3) -0.02872(18) 0.0749(8) Uani 1 1 d . . . . .
H8AA H 0.366489 0.460739 -0.054246 0.090 Uiso 0.6 1 calc R U P C 1
H8AB H 0.421477 0.395824 0.019163 0.090 Uiso 0.6 1 calc R U P C 1
H8BC H 0.429568 0.360415 0.004720 0.090 Uiso 0.4 1 calc R U P D 2
H8BD H 0.375333 0.467385 -0.021103 0.090 Uiso 0.4 1 calc R U P D 2
C3 C 0.0347(2) 0.24780(19) -0.18368(18) 0.0749(8) Uani 1 1 d . . . . .
H3A H -0.022160 0.265197 -0.145624 0.090 Uiso 1 1 calc R U . . .
H3B H 0.005609 0.219378 -0.235917 0.090 Uiso 1 1 calc R U . . .
C7 C 0.4090(4) 0.3135(5) -0.0913(4) 0.0807(16) Uani 0.6 1 d . . P E 1
H7A H 0.436596 0.251512 -0.062881 0.097 Uiso 0.6 1 calc R U P E 1
H7B H 0.462694 0.343140 -0.127444 0.097 Uiso 0.6 1 calc R U P E 1
C7A C 0.3865(7) 0.3616(7) -0.1269(5) 0.076(2) Uani 0.4 1 d . . P E 2
H7AA H 0.374667 0.423164 -0.162429 0.092 Uiso 0.4 1 calc R U P E 2
H7AB H 0.455973 0.335216 -0.138033 0.092 Uiso 0.4 1 calc R U P E 2
H1 H 0.052(2) 0.400(2) 0.0895(16) 0.080(8) Uiso 1 1 d . . . . .
H9 H 0.2776(19) 0.2848(19) 0.0286(16) 0.067(7) Uiso 1 1 d . . . . .
H1A H 0.123(2) 0.2234(19) -0.0336(18) 0.063(8) Uiso 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 C10 1.421(3) . ?
O1 H1 0.99(3) . ?
N2 C12 1.335(3) . ?
N2 C5 1.503(3) . ?
N2 C2 1.473(3) . ?
O2 C12 1.240(3) . ?
C12 C11 1.507(3) . ?
N1 C5 1.457(3) . ?
N1 C4 1.467(3) . ?
N1 H1A 0.78(3) . ?
C5 C9 1.548(3) . ?
C5 C6 1.550(3) . ?
F1 C1 1.340(3) . ?
F3 C1 1.343(3) . ?
C10 C9 1.516(3) . ?
C10 C11 1.520(3) . ?
C10 C1 1.527(4) . ?
F2 C1 1.335(3) . ?
C9 C8 1.527(3) . ?
C9 H9 0.92(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.509(4) . ?
C6 H6AA 0.9700 . ?
C6 H6AB 0.9700 . ?
C6 H6BC 0.9700 . ?
C6 H6BD 0.9700 . ?
C6 C7 1.527(7) . ?
C6 C7A 1.383(9) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C3 1.506(4) . ?
C8 H8AA 0.9700 . ?
C8 H8AB 0.9700 . ?
C8 H8BC 0.9700 . ?
C8 H8BD 0.9700 . ?
C8 C7 1.463(7) . ?
C8 C7A 1.594(9) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7A H7AA 0.9700 . ?
C7A H7AB 0.9700 . ?

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
C10 O1 H1 108.8(15) . . ?
C12 N2 C5 126.61(18) . . ?
C12 N2 C2 118.33(19) . . ?
C2 N2 C5 113.99(18) . . ?
N2 C12 C11 119.19(19) . . ?
O2 C12 N2 121.9(2) . . ?
O2 C12 C11 118.9(2) . . ?
C5 N1 C4 114.51(19) . . ?
C5 N1 H1A 102.7(18) . . ?
C4 N1 H1A 109(2) . . ?
N2 C5 C9 111.95(18) . . ?
N2 C5 C6 109.09(18) . . ?
N1 C5 N2 109.68(17) . . ?
N1 C5 C9 110.98(18) . . ?
N1 C5 C6 111.3(2) . . ?
C9 C5 C6 103.68(19) . . ?
O1 C10 C9 106.61(18) . . ?
O1 C10 C11 111.32(18) . . ?
O1 C10 C1 107.18(19) . . ?
C9 C10 C11 110.31(19) . . ?
C9 C10 C1 111.5(2) . . ?
C11 C10 C1 109.9(2) . . ?
C5 C9 H9 101.0(15) . . ?
C10 C9 C5 112.82(18) . . ?
C10 C9 C8 117.8(2) . . ?
C10 C9 H9 108.1(16) . . ?
C8 C9 C5 105.2(2) . . ?
C8 C9 H9 110.6(16) . . ?
C12 C11 C10 112.98(17) . . ?
C12 C11 H11A 109.0 . . ?
C12 C11 H11B 109.0 . . ?
C10 C11 H11A 109.0 . . ?
C10 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
N2 C2 H2A 109.7 . . ?
N2 C2 H2B 109.7 . . ?
N2 C2 C3 109.7(2) . . ?
H2A C2 H2B 108.2 . . ?
C3 C2 H2A 109.7 . . ?
C3 C2 H2B 109.7 . . ?
C5 C6 H6AA 110.7 . . ?
C5 C6 H6AB 110.7 . . ?
C5 C6 H6BC 110.2 . . ?
C5 C6 H6BD 110.2 . . ?
H6AA C6 H6AB 108.8 . . ?
H6BC C6 H6BD 108.5 . . ?
C7 C6 C5 105.4(3) . . ?
C7 C6 H6AA 110.7 . . ?
C7 C6 H6AB 110.7 . . ?
C7A C6 C5 107.6(4) . . ?
C7A C6 H6BC 110.2 . . ?
C7A C6 H6BD 110.2 . . ?
F1 C1 F3 106.4(3) . . ?
F1 C1 C10 111.4(2) . . ?
F3 C1 C10 113.0(2) . . ?
F2 C1 F1 106.3(2) . . ?
F2 C1 F3 106.9(3) . . ?
F2 C1 C10 112.4(3) . . ?
N1 C4 H4A 108.8 . . ?
N1 C4 H4B 108.8 . . ?
N1 C4 C3 113.8(2) . . ?
H4A C4 H4B 107.7 . . ?
C3 C4 H4A 108.8 . . ?
C3 C4 H4B 108.8 . . ?
C9 C8 H8AA 111.4 . . ?
C9 C8 H8AB 111.4 . . ?
C9 C8 H8BC 110.6 . . ?
C9 C8 H8BD 110.6 . . ?
C9 C8 C7A 105.7(4) . . ?
H8AA C8 H8AB 109.2 . . ?
H8BC C8 H8BD 108.7 . . ?
C7 C8 C9 102.0(3) . . ?
C7 C8 H8AA 111.4 . . ?
C7 C8 H8AB 111.4 . . ?
C7A C8 H8BC 110.6 . . ?
C7A C8 H8BD 110.6 . . ?
C2 C3 H3A 109.7 . . ?
C2 C3 H3B 109.7 . . ?
C4 C3 C2 109.8(2) . . ?
C4 C3 H3A 109.7 . . ?
C4 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
C6 C7 H7A 110.5 . . ?
C6 C7 H7B 110.5 . . ?
C8 C7 C6 106.2(3) . . ?
C8 C7 H7A 110.5 . . ?
C8 C7 H7B 110.5 . . ?
H7A C7 H7B 108.7 . . ?
C6 C7A C8 106.7(5) . . ?
C6 C7A H7AA 110.4 . . ?
C6 C7A H7AB 110.4 . . ?
C8 C7A H7AA 110.4 . . ?
C8 C7A H7AB 110.4 . . ?
H7AA C7A H7AB 108.6 . . ?

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
O1 C10 C9 C5 64.2(2) . . . . ?
O1 C10 C9 C8 -172.83(19) . . . . ?
O1 C10 C11 C12 -66.1(2) . . . . ?
O1 C10 C1 F1 -54.3(3) . . . . ?
O1 C10 C1 F3 -173.9(2) . . . . ?
O1 C10 C1 F2 64.9(3) . . . . ?
N2 C12 C11 C10 -27.5(3) . . . . ?
N2 C5 C9 C10 35.3(3) . . . . ?
N2 C5 C9 C8 -94.4(2) . . . . ?
N2 C5 C6 C7 121.0(3) . . . . ?
N2 C5 C6 C7A 84.9(5) . . . . ?
N2 C2 C3 C4 -54.4(3) . . . . ?
O2 C12 C11 C10 154.1(2) . . . . ?
C12 N2 C5 N1 113.3(2) . . . . ?
C12 N2 C5 C9 -10.4(3) . . . . ?
C12 N2 C5 C6 -124.5(2) . . . . ?
C12 N2 C2 C3 -111.2(2) . . . . ?
N1 C5 C9 C10 -87.6(2) . . . . ?
N1 C5 C9 C8 142.7(2) . . . . ?
N1 C5 C6 C7 -117.9(3) . . . . ?
N1 C5 C6 C7A -153.9(5) . . . . ?
N1 C4 C3 C2 52.0(3) . . . . ?
C5 N2 C12 O2 -175.06(19) . . . . ?
C5 N2 C12 C11 6.6(3) . . . . ?
C5 N2 C2 C3 57.7(3) . . . . ?
C5 N1 C4 C3 -51.3(3) . . . . ?
C5 C9 C8 C7 -39.8(3) . . . . ?
C5 C9 C8 C7A -6.0(4) . . . . ?
C5 C6 C7 C8 -26.9(5) . . . . ?
C5 C6 C7A C8 30.7(6) . . . . ?
C10 C9 C8 C7 -166.5(3) . . . . ?
C10 C9 C8 C7A -132.8(4) . . . . ?
C9 C5 C6 C7 1.5(3) . . . . ?
C9 C5 C6 C7A -34.5(5) . . . . ?
C9 C10 C11 C12 52.1(2) . . . . ?
C9 C10 C1 F1 -170.6(2) . . . . ?
C9 C10 C1 F3 69.8(3) . . . . ?
C9 C10 C1 F2 -51.4(3) . . . . ?
C9 C8 C7 C6 41.0(4) . . . . ?
C9 C8 C7A C6 -15.5(7) . . . . ?
C11 C10 C9 C5 -56.8(2) . . . . ?
C11 C10 C9 C8 66.2(3) . . . . ?
C11 C10 C1 F1 66.8(3) . . . . ?
C11 C10 C1 F3 -52.8(3) . . . . ?
C11 C10 C1 F2 -174.0(2) . . . . ?
C2 N2 C12 O2 -7.7(3) . . . . ?
C2 N2 C12 C11 174.0(2) . . . . ?
C2 N2 C5 N1 -54.6(2) . . . . ?
C2 N2 C5 C9 -178.26(19) . . . . ?
C2 N2 C5 C6 67.6(2) . . . . ?
C6 C5 C9 C10 152.8(2) . . . . ?
C6 C5 C9 C8 23.0(2) . . . . ?
C1 C10 C9 C5 -179.14(19) . . . . ?
C1 C10 C9 C8 -56.2(3) . . . . ?
C1 C10 C11 C12 175.4(2) . . . . ?
C4 N1 C5 N2 50.1(3) . . . . ?
C4 N1 C5 C9 174.3(2) . . . . ?
C4 N1 C5 C6 -70.7(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.202
_oxdiff_exptl_absorpt_empirical_full_min 0.881
####################################################################### 
# 
# 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_exp_769
_database_code_depnum_ccdc_archive 'CCDC 2107625'
loop_
_audit_author_name
_audit_author_address
'Pavel A. Slepukhin'
;Postovsky Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2021-09-04 deposited with the CCDC.	2021-10-28 downloaded from the CCDC.
;
_audit_creation_date             2020-06-04
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_chemical_formula_moiety         'C17 H19 F3 N2 O2, C2 H3 N'
_chemical_formula_sum            'C19 H22 F3 N3 O2'
_chemical_formula_weight         381.401
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 0.00347 0.00161 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 0.01794 0.01033 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 0.01158 0.00611 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 0.00653 0.00323 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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   10.2653(9)
_cell_length_b                   9.7195(12)
_cell_length_c                   19.2671(17)
_cell_angle_alpha                90
_cell_angle_beta                 104.837(9)
_cell_angle_gamma                90
_cell_volume                     1858.3(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1472
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      23.8050
_cell_measurement_theta_min      3.9520
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82513
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.38a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_description       block
_exptl_crystal_F_000             800.505
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.21
_diffrn_reflns_av_R_equivalents  0.0537
_diffrn_reflns_av_unetI/netI     0.0843
_diffrn_reflns_Laue_measured_fraction_full 0.9813
_diffrn_reflns_Laue_measured_fraction_max 0.8399
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11434
_diffrn_reflns_point_group_measured_fraction_full 0.9813
_diffrn_reflns_point_group_measured_fraction_max 0.8399
_diffrn_reflns_theta_full        26.0000
_diffrn_reflns_theta_max         31.04
_diffrn_reflns_theta_min         3.89
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.5253
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.9813
_diffrn_measured_fraction_theta_max 0.8399
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -91.00   1.00   1.00   15.00    --  -24.08 -77.00 150.00   92
  2  ω    -54.00  38.00   1.00   15.00    --  -24.08  77.00 -90.00   92
  3  ω    -93.00  -3.00   1.00   15.00    --  -24.08 -57.00  30.00   90
  4  ω    -50.00 -41.00   1.00   15.00    --  -24.08  77.00   0.00    9
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0443416000
_diffrn_orient_matrix_UB_12      0.0469593000
_diffrn_orient_matrix_UB_13      0.0104572000
_diffrn_orient_matrix_UB_21      -0.0554809000
_diffrn_orient_matrix_UB_22      -0.0310337000
_diffrn_orient_matrix_UB_23      -0.0247439000
_diffrn_orient_matrix_UB_31      -0.0078195000
_diffrn_orient_matrix_UB_32      -0.0465594000
_diffrn_orient_matrix_UB_33      0.0269731000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              13
_reflns_limit_h_min              -13
_reflns_limit_k_max              13
_reflns_limit_k_min              0
_reflns_limit_l_max              27
_reflns_limit_l_min              0
_reflns_number_gt                2208
_reflns_number_total             4978
_reflns_odcompleteness_completeness 96.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.3708
_refine_diff_density_min         -0.4323
_refine_diff_density_rms         0.0984
_refine_ls_d_res_high            0.6892
_refine_ls_d_res_low             5.2320
_refine_ls_goodness_of_fit_ref   1.0099
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    27
_refine_ls_number_parameters     265
_refine_ls_number_reflns         4978
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1534
_refine_ls_R_factor_gt           0.0635
_refine_ls_restrained_S_all      1.0099
_refine_ls_shift/su_max          0.0005
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0850P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1454
_refine_ls_wR_factor_ref         0.2223
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9a,H9b), C10(H10a,H10b), C11(H11a,H11b), C12(H12a,H12b), C15(H15a,H15b)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C5(H5), C4(H4), C3(H3)
2.c Idealised Me refined as rotating group:
 C3s(H3sa,H3sb,H3sc)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
O1 O 0.77388(19) 0.4301(2) 0.41728(10) 0.0551(5) Uani 1.000000 .
N1 N 0.98073(19) 0.5458(2) 0.33577(11) 0.0464(6) Uani 1.000000 .
N2 N 0.8477(2) 0.6006(2) 0.22168(11) 0.0478(6) Uani 1.000000 .
O2 O 1.12362(19) 0.6045(3) 0.43985(10) 0.0715(7) Uani 1.000000 .
F1 F 0.6188(2) 0.7595(2) 0.40451(11) 0.0911(7) Uani 1.000000 .
F2 F 0.53971(19) 0.5600(3) 0.41457(11) 0.0936(7) Uani 1.000000 .
F3 F 0.6924(2) 0.6417(3) 0.49990(10) 0.0970(7) Uani 1.000000 .
C8 C 0.8452(2) 0.5240(3) 0.28688(13) 0.0430(6) Uani 1.000000 .
C9 C 0.8256(2) 0.3700(3) 0.27289(14) 0.0452(6) Uani 1.000000 .
C2 C 1.0729(3) 0.5222(3) 0.23116(14) 0.0508(7) Uani 1.000000 .
C12 C 0.5944(2) 0.5420(3) 0.27173(15) 0.0538(7) Uani 1.000000 .
C14 C 1.0072(3) 0.5964(3) 0.40208(14) 0.0525(7) Uani 1.000000 .
C7 C 0.9522(3) 0.5731(3) 0.18993(14) 0.0482(6) Uani 1.000000 .
C13 C 0.7330(3) 0.5883(3) 0.31659(14) 0.0469(6) Uani 1.000000 .
C15 C 0.8933(3) 0.6453(3) 0.43070(14) 0.0575(7) Uani 1.000000 .
C10 C 0.6858(3) 0.3345(3) 0.22767(15) 0.0555(7) Uani 1.000000 .
C6 C 0.9393(3) 0.6035(3) 0.11793(15) 0.0619(8) Uani 1.000000 .
C11 C 0.5793(3) 0.3875(3) 0.26208(16) 0.0594(8) Uani 1.000000 .
C1 C 1.0930(3) 0.4946(4) 0.30930(16) 0.0589(8) Uani 1.000000 .
C3 C 1.1776(3) 0.4991(3) 0.19896(18) 0.0635(8) Uani 1.000000 .
C16 C 0.7628(3) 0.5710(3) 0.39823(14) 0.0512(7) Uani 1.000000 .
C4 C 1.1647(4) 0.5293(4) 0.1285(2) 0.0767(10) Uani 1.000000 .
C5 C 1.0457(4) 0.5829(4) 0.08848(18) 0.0746(10) Uani 1.000000 .
C2s C 0.4832(4) 0.6513(4) 0.05018(19) 0.0793(10) Uani 1.000000 .
N1s N 0.5768(4) 0.6222(5) 0.0912(2) 0.1249(15) Uani 1.000000 .
C3s C 0.3640(4) 0.6888(5) -0.0033(2) 0.1002(14) Uani 1.000000 .
C17 C 0.6536(3) 0.6320(4) 0.42866(17) 0.0692(9) Uani 1.000000 .
H2 H 0.771(3) 0.606(3) 0.1928(16) 0.065(9) Uiso 1.000000 .
H1 H 0.810(3) 0.425(4) 0.4682(19) 0.086(11) Uiso 1.000000 .
H13 H 0.736(2) 0.687(3) 0.3096(14) 0.057(8) Uiso 1.000000 .
H1a H 1.172(3) 0.539(3) 0.3380(16) 0.073(10) Uiso 1.000000 .
H9a H 0.8918(2) 0.3377(3) 0.24862(14) 0.0543(7) Uiso 1.000000 R
H9b H 0.8415(2) 0.3222(3) 0.31848(14) 0.0543(7) Uiso 1.000000 R
H10a H 0.6725(3) 0.3748(3) 0.18030(15) 0.0666(9) Uiso 1.000000 R
H10b H 0.6774(3) 0.2355(3) 0.22215(15) 0.0666(9) Uiso 1.000000 R
H11a H 0.5890(3) 0.3437(3) 0.30835(16) 0.0713(9) Uiso 1.000000 R
H11b H 0.4905(3) 0.3659(3) 0.23198(16) 0.0713(9) Uiso 1.000000 R
H12a H 0.5263(2) 0.5751(3) 0.29449(15) 0.0645(9) Uiso 1.000000 R
H12b H 0.5774(2) 0.5847(3) 0.22474(15) 0.0645(9) Uiso 1.000000 R
H15a H 0.9168(3) 0.6325(3) 0.48235(14) 0.0690(9) Uiso 1.000000 R
H15b H 0.8802(3) 0.7430(3) 0.42119(14) 0.0690(9) Uiso 1.000000 R
H6 H 0.8584(3) 0.6380(3) 0.08980(15) 0.0743(10) Uiso 1.000000 R
H5 H 1.0371(4) 0.6055(4) 0.04061(18) 0.0895(11) Uiso 1.000000 R
H4 H 1.2359(4) 0.5137(4) 0.1079(2) 0.0920(12) Uiso 1.000000 R
H3 H 1.2582(3) 0.4623(3) 0.22613(18) 0.0762(10) Uiso 1.000000 R
H3sa H 0.3508(18) 0.6263(19) -0.0431(8) 0.150(2) Uiso 1.000000 GR
H3sb H 0.2877(6) 0.685(3) 0.0168(5) 0.150(2) Uiso 1.000000 GR
H3sc H 0.3734(13) 0.7807(12) -0.0196(12) 0.150(2) Uiso 1.000000 GR
H1b H 1.108(3) 0.389(3) 0.3201(15) 0.064(8) Uiso 1.000000 .


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 C16 1.414(3) . ?
O1 H1 0.96(3) . ?
N1 C8 1.483(3) . ?
N1 C14 1.331(3) . ?
N1 C1 1.462(4) . ?
N2 C8 1.466(3) . ?
N2 C7 1.390(3) . ?
N2 H2 0.84(3) . ?
O2 C14 1.233(3) . ?
F1 C17 1.340(4) . ?
F2 C17 1.329(4) . ?
F3 C17 1.331(3) . ?
C8 C9 1.525(4) . ?
C8 C13 1.543(4) . ?
C9 C10 1.516(3) . ?
C9 H9a 0.9700 . ?
C9 H9b 0.9700 . ?
C2 C7 1.381(4) . ?
C2 C1 1.491(4) . ?
C2 C3 1.390(4) . ?
C12 C13 1.531(4) . ?
C12 C11 1.516(4) . ?
C12 H12a 0.9700 . ?
C12 H12b 0.9700 . ?
C14 C15 1.492(4) . ?
C7 C6 1.391(4) . ?
C13 C16 1.533(4) . ?
C13 H13 0.97(3) . ?
C15 C16 1.509(4) . ?
C15 H15a 0.9700 . ?
C15 H15b 0.9700 . ?
C10 C11 1.507(4) . ?
C10 H10a 0.9700 . ?
C10 H10b 0.9700 . ?
C6 C5 1.368(4) . ?
C6 H6 0.9300 . ?
C11 H11a 0.9700 . ?
C11 H11b 0.9700 . ?
C1 H1a 0.96(3) . ?
C1 H1b 1.05(3) . ?
C3 C4 1.361(4) . ?
C3 H3 0.9300 . ?
C16 C17 1.513(4) . ?
C4 C5 1.370(5) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C2s N1s 1.113(4) . ?
C2s C3s 1.431(5) . ?
C3s H3sa 0.9600 . ?
C3s H3sb 0.9600 . ?
C3s H3sc 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H1 O1 C16 107(2) . . ?
C14 N1 C8 126.2(2) . . ?
C1 N1 C8 115.2(2) . . ?
C1 N1 C14 118.4(2) . . ?
C7 N2 C8 117.7(2) . . ?
H2 N2 C8 112(2) . . ?
H2 N2 C7 115(2) . . ?
N2 C8 N1 104.6(2) . . ?
C9 C8 N1 108.2(2) . . ?
C9 C8 N2 112.2(2) . . ?
C13 C8 N1 112.0(2) . . ?
C13 C8 N2 106.9(2) . . ?
C13 C8 C9 112.7(2) . . ?
C10 C9 C8 112.8(2) . . ?
H9a C9 C8 109.04(13) . . ?
H9a C9 C10 109.04(14) . . ?
H9b C9 C8 109.04(13) . . ?
H9b C9 C10 109.04(15) . . ?
H9b C9 H9a 107.8 . . ?
C1 C2 C7 121.1(3) . . ?
C3 C2 C7 118.9(3) . . ?
C3 C2 C1 119.9(3) . . ?
C11 C12 C13 114.3(2) . . ?
H12a C12 C13 108.69(14) . . ?
H12a C12 C11 108.69(15) . . ?
H12b C12 C13 108.69(16) . . ?
H12b C12 C11 108.69(16) . . ?
H12b C12 H12a 107.6 . . ?
O2 C14 N1 121.3(3) . . ?
C15 C14 N1 119.1(2) . . ?
C15 C14 O2 119.6(3) . . ?
C2 C7 N2 119.7(2) . . ?
C6 C7 N2 120.8(3) . . ?
C6 C7 C2 119.4(3) . . ?
C12 C13 C8 110.2(2) . . ?
C16 C13 C8 111.3(2) . . ?
C16 C13 C12 117.4(2) . . ?
H13 C13 C8 106.9(15) . . ?
H13 C13 C12 105.9(15) . . ?
H13 C13 C16 104.2(16) . . ?
C16 C15 C14 113.0(2) . . ?
H15a C15 C14 108.99(14) . . ?
H15a C15 C16 108.99(15) . . ?
H15b C15 C14 108.99(16) . . ?
H15b C15 C16 108.99(16) . . ?
H15b C15 H15a 107.8 . . ?
C11 C10 C9 110.9(2) . . ?
H10a C10 C9 109.47(15) . . ?
H10a C10 C11 109.47(16) . . ?
H10b C10 C9 109.47(15) . . ?
H10b C10 C11 109.47(16) . . ?
H10b C10 H10a 108.1 . . ?
C5 C6 C7 120.0(3) . . ?
H6 C6 C7 119.98(18) . . ?
H6 C6 C5 120.0(2) . . ?
C10 C11 C12 109.3(2) . . ?
H11a C11 C12 109.83(16) . . ?
H11a C11 C10 109.83(17) . . ?
H11b C11 C12 109.83(14) . . ?
H11b C11 C10 109.83(14) . . ?
H11b C11 H11a 108.3 . . ?
C2 C1 N1 111.9(2) . . ?
H1a C1 N1 105.5(18) . . ?
H1a C1 C2 112.4(18) . . ?
H1b C1 N1 110.5(15) . . ?
H1b C1 C2 110.5(16) . . ?
H1b C1 H1a 106(2) . . ?
C4 C3 C2 121.4(3) . . ?
H3 C3 C2 119.28(18) . . ?
H3 C3 C4 119.3(2) . . ?
C13 C16 O1 110.8(2) . . ?
C15 C16 O1 110.6(2) . . ?
C15 C16 C13 107.2(2) . . ?
C17 C16 O1 107.3(2) . . ?
C17 C16 C13 112.4(2) . . ?
C17 C16 C15 108.6(3) . . ?
C5 C4 C3 119.2(3) . . ?
H4 C4 C3 120.4(2) . . ?
H4 C4 C5 120.4(2) . . ?
C4 C5 C6 120.9(3) . . ?
H5 C5 C6 119.5(2) . . ?
H5 C5 C4 119.5(2) . . ?
C3s C2s N1s 179.2(4) . . ?
H3sa C3s C2s 109.5 . . ?
H3sb C3s C2s 109.5 . . ?
H3sb C3s H3sa 109.5 . . ?
H3sc C3s C2s 109.5 . . ?
H3sc C3s H3sa 109.5 . . ?
H3sc C3s H3sb 109.5 . . ?
F2 C17 F1 105.9(3) . . ?
F3 C17 F1 106.0(3) . . ?
F3 C17 F2 105.2(3) . . ?
C16 C17 F1 112.7(3) . . ?
C16 C17 F2 114.5(3) . . ?
C16 C17 F3 111.8(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
O1 C16 C13 C8 -59.4(2) . . . . ?
O1 C16 C13 C12 68.9(2) . . . . ?
O1 C16 C15 C14 64.7(2) . . . . ?
O1 C16 C17 F1 -170.0(2) . . . . ?
O1 C16 C17 F2 -48.9(2) . . . . ?
O1 C16 C17 F3 70.7(2) . . . . ?
N1 C8 N2 C7 53.1(2) . . . . ?
N1 C8 C9 C10 175.8(2) . . . . ?
N1 C8 C13 C12 -170.0(2) . . . . ?
N1 C8 C13 C16 -37.9(2) . . . . ?
N1 C14 C15 C16 28.7(3) . . . . ?
N1 C1 C2 C7 -8.1(3) . . . . ?
N1 C1 C2 C3 170.6(2) . . . . ?
N2 C8 C9 C10 -69.4(2) . . . . ?
N2 C8 C13 C12 76.0(2) . . . . ?
N2 C8 C13 C16 -151.9(2) . . . . ?
N2 C7 C2 C1 0.6(3) . . . . ?
N2 C7 C2 C3 -178.1(3) . . . . ?
N2 C7 C6 C5 176.4(3) . . . . ?
O2 C14 C15 C16 -151.9(3) . . . . ?
F1 C17 C16 C13 -48.0(3) . . . . ?
F1 C17 C16 C15 70.5(3) . . . . ?
F2 C17 C16 C13 73.1(3) . . . . ?
F2 C17 C16 C15 -168.4(3) . . . . ?
F3 C17 C16 C13 -167.3(3) . . . . ?
F3 C17 C16 C15 -48.8(3) . . . . ?
C8 C9 C10 C11 -56.6(2) . . . . ?
C8 C13 C12 C11 52.0(2) . . . . ?
C8 C13 C16 C15 61.3(2) . . . . ?
C8 C13 C16 C17 -179.4(3) . . . . ?
C9 C10 C11 C12 58.2(3) . . . . ?
C2 C7 C6 C5 0.1(3) . . . . ?
C2 C3 C4 C5 -0.4(4) . . . . ?
C12 C13 C16 C15 -170.4(3) . . . . ?
C12 C13 C16 C17 -51.1(3) . . . . ?
C14 C15 C16 C13 -56.1(3) . . . . ?
C14 C15 C16 C17 -177.8(3) . . . . ?
C7 C6 C5 C4 1.5(4) . . . . ?
C6 C5 C4 C3 -1.4(4) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.105
_oxdiff_exptl_absorpt_empirical_full_min 0.861
