# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_16854_abb899
_database_code_depnum_ccdc_archive 'CCDC 2056273'
loop_
_audit_author_name
_audit_author_address
'Olga Bakulina'
;Saint Petersburg State University
Russia
;
_audit_update_record             
;
2021-01-14 deposited with the CCDC.	2022-10-14 downloaded from the CCDC.
;
_audit_creation_date             2021-01-14
_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         'C16 H19 N O4'
_chemical_formula_sum            'C16 H19 N O4'
_chemical_formula_weight         289.32
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C16 H19 O4 N1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.8108(2)
_cell_length_b                   6.5963(2)
_cell_length_c                   13.6805(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.914(2)
_cell_angle_gamma                90
_cell_volume                     699.73(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7777
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.9500
_cell_measurement_theta_min      3.2460
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.812
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83858
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.71a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9975
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.217
_diffrn_reflns_theta_min         3.254
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -26.00  25.00   0.50    0.15    --   47.20 -19.00 -60.00  102
  2  ω     13.00  76.00   0.50    0.15    --   47.20-100.00-151.00  126
  3  ω     58.00 100.00   0.50    0.60    --  107.75-100.00-151.00   84
  4  ω     81.00 106.00   0.50    0.60    --  107.75 -77.00-180.00   50
  5  ω     71.00  99.00   0.50    0.60    --  107.75 -94.00-120.00   56
  6  ω     61.00 104.00   0.50    0.60    --  107.75 -77.00-120.00   86
  7  ω     35.00  73.00   0.50    0.60    --  107.75 -77.00-150.00   76
  8  ω     37.00  71.00   0.50    0.60    --  107.75 -61.00 -90.00   68
  9  ω     40.00  70.00   0.50    0.60    --  107.75 -61.00 -60.00   60
 10  ω     36.00  70.00   0.50    0.60    --  107.75 -61.00   0.00   68
 11  ω     55.00 103.00   0.50    0.60    --  107.75 -77.00  60.00   96
 12  ω     38.00  71.00   0.50    0.60    --  107.75 -61.00  30.00   66
 13  ω    106.00 178.00   0.50    0.60    --  107.75  45.00  90.00  144
 14  ω    147.00 175.00   0.50    0.60    --  107.75  45.00  30.00   56
 15  ω    113.00 139.00   0.50    0.60    --  107.75 100.00 -46.00   52
 16  ω     95.00 143.00   0.50    0.60    --  107.75  45.00  30.00   96
 17  ω     74.00  99.00   0.50    0.15    --   47.20 125.00 -90.00   50
 18  ω     79.00 119.00   0.50    0.15    --   47.20 125.00-120.00   80
 19  ω    104.00 178.00   0.50    0.60    --  107.75  15.00-180.00  148
 20  ω     35.00  61.00   0.50    0.60    --  107.75 -77.00-180.00   52
 21  ω    -71.00 -23.00   0.50    0.15    --  -47.20 100.00 -46.00   96
 22  ω    -12.00  22.00   0.50    0.15    --  -47.20 100.00 -46.00   68
 23  ω    -63.00 -38.00   0.50    0.60    -- -106.00  61.00 -60.00   50
 24  ω    -61.00 -33.00   0.50    0.60    -- -106.00  61.00 -90.00   56
 25  ω    -98.00 -65.00   0.50    0.60    -- -106.00 100.00 -46.00   66
 26  ω    -59.00 -34.00   0.50    0.60    -- -106.00  61.00  90.00   50
 27  ω    -62.00 -37.00   0.50    0.60    -- -106.00  61.00 150.00   50
 28  ω   -165.00-104.00   0.50    0.60    -- -106.00-100.00-151.00  122
 29  ω    101.00 127.00   0.50    0.60    --  107.75 100.00 -46.00   52
 30  ω     88.00 113.00   0.50    0.15    --   47.20 125.00 -90.00   50
 31  ω    -10.00  26.00   0.50    0.15    --   47.20 -19.00-120.00   72
 32  ω    -22.00   4.00   0.50    0.15    --   47.20 -19.00  30.00   52
 33  ω     46.00  95.00   0.50    0.15    --   47.20  57.00  60.00   98
 34  ω   -119.00 -88.00   0.50    0.60    -- -106.00 -68.00 -93.15   62
 35  ω   -121.00 -96.00   0.50    0.60    -- -106.00 138.00-138.62   50
 36  ω   -108.00 -82.00   0.50    0.60    -- -106.00 109.00-174.39   52
 37  ω   -112.00 -87.00   0.50    0.60    -- -106.00 125.00 -60.00   50
 38  ω   -114.00 -88.00   0.50    0.60    -- -106.00-125.00  30.00   52
 39  ω   -159.00-127.00   0.50    0.60    -- -106.00 -83.00 -98.08   64
 40  ω   -158.00-132.00   0.50    0.60    -- -106.00 -68.00 -93.15   52
 41  ω   -121.00 -95.00   0.50    0.60    -- -106.00 -30.00  90.00   52
 42  ω   -117.00 -83.00   0.50    0.60    -- -106.00 -77.00 -60.00   68
 43  ω   -173.00-128.00   0.50    0.60    -- -106.00 -77.00 -60.00   90
 44  ω   -105.00 -80.00   0.50    0.60    -- -106.00 -83.00 -98.08   50
 45  ω   -105.00 -80.00   0.50    0.60    -- -106.00 125.00 -30.00   50
 46  ω   -170.00-144.00   0.50    0.60    -- -106.00 -30.00  90.00   52
 47  ω   -112.00 -75.00   0.50    0.60    -- -106.00 125.00  90.00   74
 48  ω    -67.00 -35.00   0.50    0.60    -- -106.00 125.00 -30.00   64
 49  ω   -171.00-146.00   0.50    0.60    -- -106.00-125.00  30.00   50
 50  ω     74.00  99.00   0.50    0.60    --  107.75 -94.00 -30.00   50
 51  ω     67.00 104.00   0.50    0.60    --  107.75-125.00-150.00   74
 52  ω     36.00  62.00   0.50    0.60    --  107.75-125.00-150.00   52
 53  ω    128.00 174.00   0.50    0.60    --  107.75  45.00  60.00   92
 54  ω     91.00 124.00   0.50    0.60    --  107.75  61.00 -90.00   66
 55  ω     39.00  69.00   0.50    0.60    --  107.75 -61.00-120.00   60
 56  ω     87.00 112.00   0.50    0.60    --  107.75-125.00-120.00   50
 57  ω    144.00 172.00   0.50    0.60    --  107.75  61.00   0.00   56
 58  ω     42.00  67.00   0.50    0.60    --  107.75-125.00-120.00   50
 59  ω     64.00  90.00   0.50    0.60    --  107.75-125.00  30.00   52
 60  ω    100.00 126.00   0.50    0.60    --  107.75  61.00   0.00   52
 61  ω     85.00 125.00   0.50    0.60    --  107.75  77.00 -90.00   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1290677000
_diffrn_orient_matrix_UB_12      0.0335436000
_diffrn_orient_matrix_UB_13      -0.0929568000
_diffrn_orient_matrix_UB_21      -0.0297498000
_diffrn_orient_matrix_UB_22      0.2191448000
_diffrn_orient_matrix_UB_23      0.0329136000
_diffrn_orient_matrix_UB_31      0.1480684000
_diffrn_orient_matrix_UB_32      0.0734947000
_diffrn_orient_matrix_UB_33      -0.0560717000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.816
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.965
_reflns_number_gt                2840
_reflns_number_total             2903
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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 1.171.40.71a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.71a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.71a (Rigaku OD, 2020)'
_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         0.182
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 
;
 Flack x determined using 1254 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2903
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0322
_refine_ls_restrained_S_all      1.064
_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)+(0.0481P)²+0.0851P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0834
_refine_ls_wR_factor_ref         0.0840
_refine_special_details          ?
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00B(H00A,H00B), C00E(H00E,H00F), C00F(H00G,H00H), C00G(H00I,H00J), C00J(H00L,
 H00M)
2.b Aromatic/amide H refined with riding coordinates:
 C008(H008), C00C(H00C), C00D(H00D), C00H(H00K), C00K(H00N)
2.c Idealised Me refined as rotating group:
 C00L(H00O,H00P,H00Q)
2.d Idealised tetrahedral OH refined as rotating group:
 O003(H003)
;
_atom_sites_solution_hydrogens   geom
_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
O001 O 0.37458(16) 0.4478(2) 0.43499(9) 0.0189(3) Uani 1 1 d . . . . .
O002 O -0.03381(17) 1.0064(2) 0.71341(9) 0.0190(3) Uani 1 1 d . . . . .
O003 O 0.13473(17) 0.7139(2) 0.45659(9) 0.0205(3) Uani 1 1 d . . . . .
H003 H 0.136050 0.636990 0.409612 0.031 Uiso 1 1 calc R U . . .
O004 O 0.80916(18) 0.1530(2) 1.04923(10) 0.0205(3) Uani 1 1 d . . . . .
N005 N 0.2383(2) 0.6340(2) 0.53860(11) 0.0177(3) Uani 1 1 d . . . . .
C006 C 0.3620(2) 0.5053(3) 0.52031(13) 0.0161(3) Uani 1 1 d . . . . .
C007 C 0.5426(2) 0.4031(3) 0.79406(12) 0.0164(3) Uani 1 1 d . . . . .
C008 C 0.3071(2) 0.6173(3) 0.71519(13) 0.0169(4) Uani 1 1 d . . . . .
H008 H 0.282550 0.644913 0.778687 0.020 Uiso 1 1 calc R U . . .
C009 C 0.4392(2) 0.4929(3) 0.70617(13) 0.0160(3) Uani 1 1 d . . . . .
C00A C 0.1948(2) 0.7166(3) 0.63194(12) 0.0158(3) Uani 1 1 d . . . . .
C00B C 0.4854(2) 0.4346(3) 0.60640(13) 0.0187(4) Uani 1 1 d . . . . .
H00A H 0.598709 0.488905 0.599483 0.022 Uiso 1 1 calc R U . . .
H00B H 0.493405 0.288019 0.603514 0.022 Uiso 1 1 calc R U . . .
C00C C 0.5623(2) 0.5055(3) 0.88467(13) 0.0191(4) Uani 1 1 d . . . . .
H00C H 0.515982 0.634627 0.888676 0.023 Uiso 1 1 calc R U . . .
C00D C 0.6186(2) 0.2124(3) 0.79025(13) 0.0188(4) Uani 1 1 d . . . . .
H00D H 0.610317 0.143275 0.730608 0.023 Uiso 1 1 calc R U . . .
C00E C 0.0021(2) 0.6748(3) 0.63955(14) 0.0183(4) Uani 1 1 d . . . . .
H00E H -0.065410 0.711065 0.577826 0.022 Uiso 1 1 calc R U . . .
H00F H -0.013924 0.531012 0.650322 0.022 Uiso 1 1 calc R U . . .
C00F C 0.1471(2) 1.0482(3) 0.71806(14) 0.0194(4) Uani 1 1 d . . . . .
H00G H 0.205677 0.998221 0.779922 0.023 Uiso 1 1 calc R U . . .
H00H H 0.164784 1.193597 0.715859 0.023 Uiso 1 1 calc R U . . .
C00G C 0.2241(2) 0.9487(3) 0.63309(13) 0.0175(3) Uani 1 1 d . . . . .
H00I H 0.346880 0.976594 0.639070 0.021 Uiso 1 1 calc R U . . .
H00J H 0.171667 1.006291 0.571401 0.021 Uiso 1 1 calc R U . . .
C00H C 0.6494(2) 0.4179(3) 0.96809(13) 0.0189(4) Uani 1 1 d . . . . .
H00K H 0.659809 0.487636 1.027591 0.023 Uiso 1 1 calc R U . . .
C00I C 0.7218(2) 0.2250(3) 0.96328(13) 0.0167(3) Uani 1 1 d . . . . .
C00J C -0.0635(2) 0.7936(3) 0.72292(14) 0.0191(4) Uani 1 1 d . . . . .
H00L H -0.186027 0.769431 0.722521 0.023 Uiso 1 1 calc R U . . .
H00M H -0.005354 0.746438 0.785438 0.023 Uiso 1 1 calc R U . . .
C00K C 0.7068(2) 0.1231(3) 0.87415(14) 0.0193(4) Uani 1 1 d . . . . .
H00N H 0.755542 -0.004839 0.870191 0.023 Uiso 1 1 calc R U . . .
C00L C 0.8735(3) -0.0490(3) 1.04816(15) 0.0281(4) Uani 1 1 d . . . . .
H00O H 0.956474 -0.058315 1.001952 0.042 Uiso 1 1 calc R U . . .
H00P H 0.779937 -0.140632 1.029111 0.042 Uiso 1 1 calc R U . . .
H00Q H 0.927549 -0.084233 1.112686 0.042 Uiso 1 1 calc R U . . .


_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
O001 C006 1.242(2) . ?
O002 C00F 1.434(2) . ?
O002 C00J 1.431(2) . ?
O003 H003 0.8200 . ?
O003 N005 1.4045(19) . ?
O004 C00I 1.371(2) . ?
O004 C00L 1.425(2) . ?
N005 C006 1.332(2) . ?
N005 C00A 1.465(2) . ?
C006 C00B 1.503(2) . ?
C007 C009 1.488(2) . ?
C007 C00C 1.403(2) . ?
C007 C00D 1.395(3) . ?
C008 H008 0.9300 . ?
C008 C009 1.335(3) . ?
C008 C00A 1.502(2) . ?
C009 C00B 1.503(2) . ?
C00A C00E 1.546(2) . ?
C00A C00G 1.548(3) . ?
C00B H00A 0.9700 . ?
C00B H00B 0.9700 . ?
C00C H00C 0.9300 . ?
C00C C00H 1.383(2) . ?
C00D H00D 0.9300 . ?
C00D C00K 1.396(3) . ?
C00E H00E 0.9700 . ?
C00E H00F 0.9700 . ?
C00E C00J 1.523(3) . ?
C00F H00G 0.9700 . ?
C00F H00H 0.9700 . ?
C00F C00G 1.520(3) . ?
C00G H00I 0.9700 . ?
C00G H00J 0.9700 . ?
C00H H00K 0.9300 . ?
C00H C00I 1.397(3) . ?
C00I C00K 1.385(3) . ?
C00J H00L 0.9700 . ?
C00J H00M 0.9700 . ?
C00K H00N 0.9300 . ?
C00L H00O 0.9600 . ?
C00L H00P 0.9600 . ?
C00L H00Q 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
C00J O002 C00F 110.74(14) . . ?
N005 O003 H003 109.5 . . ?
C00I O004 C00L 117.06(14) . . ?
O003 N005 C00A 112.63(14) . . ?
C006 N005 O003 116.75(14) . . ?
C006 N005 C00A 130.55(15) . . ?
O001 C006 N005 120.81(16) . . ?
O001 C006 C00B 121.70(16) . . ?
N005 C006 C00B 117.49(15) . . ?
C00C C007 C009 120.90(16) . . ?
C00D C007 C009 121.38(15) . . ?
C00D C007 C00C 117.69(16) . . ?
C009 C008 H008 117.1 . . ?
C009 C008 C00A 125.82(16) . . ?
C00A C008 H008 117.1 . . ?
C007 C009 C00B 117.73(15) . . ?
C008 C009 C007 121.33(16) . . ?
C008 C009 C00B 120.91(16) . . ?
N005 C00A C008 108.85(15) . . ?
N005 C00A C00E 108.79(14) . . ?
N005 C00A C00G 109.09(14) . . ?
C008 C00A C00E 110.85(14) . . ?
C008 C00A C00G 110.57(14) . . ?
C00E C00A C00G 108.65(14) . . ?
C006 C00B C009 115.49(15) . . ?
C006 C00B H00A 108.4 . . ?
C006 C00B H00B 108.4 . . ?
C009 C00B H00A 108.4 . . ?
C009 C00B H00B 108.4 . . ?
H00A C00B H00B 107.5 . . ?
C007 C00C H00C 119.4 . . ?
C00H C00C C007 121.27(17) . . ?
C00H C00C H00C 119.4 . . ?
C007 C00D H00D 119.3 . . ?
C007 C00D C00K 121.33(17) . . ?
C00K C00D H00D 119.3 . . ?
C00A C00E H00E 109.2 . . ?
C00A C00E H00F 109.2 . . ?
H00E C00E H00F 107.9 . . ?
C00J C00E C00A 112.11(15) . . ?
C00J C00E H00E 109.2 . . ?
C00J C00E H00F 109.2 . . ?
O002 C00F H00G 109.4 . . ?
O002 C00F H00H 109.4 . . ?
O002 C00F C00G 111.19(15) . . ?
H00G C00F H00H 108.0 . . ?
C00G C00F H00G 109.4 . . ?
C00G C00F H00H 109.4 . . ?
C00A C00G H00I 109.4 . . ?
C00A C00G H00J 109.4 . . ?
C00F C00G C00A 111.28(14) . . ?
C00F C00G H00I 109.4 . . ?
C00F C00G H00J 109.4 . . ?
H00I C00G H00J 108.0 . . ?
C00C C00H H00K 119.9 . . ?
C00C C00H C00I 120.22(16) . . ?
C00I C00H H00K 119.9 . . ?
O004 C00I C00H 115.95(15) . . ?
O004 C00I C00K 124.57(17) . . ?
C00K C00I C00H 119.45(16) . . ?
O002 C00J C00E 111.36(15) . . ?
O002 C00J H00L 109.4 . . ?
O002 C00J H00M 109.4 . . ?
C00E C00J H00L 109.4 . . ?
C00E C00J H00M 109.4 . . ?
H00L C00J H00M 108.0 . . ?
C00D C00K H00N 120.0 . . ?
C00I C00K C00D 120.02(17) . . ?
C00I C00K H00N 120.0 . . ?
O004 C00L H00O 109.5 . . ?
O004 C00L H00P 109.5 . . ?
O004 C00L H00Q 109.5 . . ?
H00O C00L H00P 109.5 . . ?
H00O C00L H00Q 109.5 . . ?
H00P C00L H00Q 109.5 . . ?

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
O001 C006 C00B C009 -171.64(15) . . . . ?
O002 C00F C00G C00A -57.57(19) . . . . ?
O003 N005 C006 O001 -5.5(2) . . . . ?
O003 N005 C006 C00B 173.93(16) . . . . ?
O003 N005 C00A C008 177.97(14) . . . . ?
O003 N005 C00A C00E 57.08(19) . . . . ?
O003 N005 C00A C00G -61.30(18) . . . . ?
O004 C00I C00K C00D -178.35(17) . . . . ?
N005 C006 C00B C009 8.9(2) . . . . ?
N005 C00A C00E C00J -167.76(15) . . . . ?
N005 C00A C00G C00F 168.38(14) . . . . ?
C006 N005 C00A C008 -5.2(3) . . . . ?
C006 N005 C00A C00E -126.1(2) . . . . ?
C006 N005 C00A C00G 115.6(2) . . . . ?
C007 C009 C00B C006 171.62(15) . . . . ?
C007 C00C C00H C00I 0.8(3) . . . . ?
C007 C00D C00K C00I -0.7(3) . . . . ?
C008 C009 C00B C006 -6.8(3) . . . . ?
C008 C00A C00E C00J 72.58(19) . . . . ?
C008 C00A C00G C00F -71.95(18) . . . . ?
C009 C007 C00C C00H 176.06(16) . . . . ?
C009 C007 C00D C00K -176.11(17) . . . . ?
C009 C008 C00A N005 7.5(3) . . . . ?
C009 C008 C00A C00E 127.14(19) . . . . ?
C009 C008 C00A C00G -112.3(2) . . . . ?
C00A N005 C006 O001 177.70(18) . . . . ?
C00A N005 C006 C00B -2.8(3) . . . . ?
C00A C008 C009 C007 179.82(16) . . . . ?
C00A C008 C009 C00B -1.8(3) . . . . ?
C00A C00E C00J O002 55.6(2) . . . . ?
C00C C007 C009 C008 -29.2(3) . . . . ?
C00C C007 C009 C00B 152.40(17) . . . . ?
C00C C007 C00D C00K 1.9(3) . . . . ?
C00C C00H C00I O004 178.48(16) . . . . ?
C00C C00H C00I C00K 0.5(3) . . . . ?
C00D C007 C009 C008 148.83(18) . . . . ?
C00D C007 C009 C00B -29.6(2) . . . . ?
C00D C007 C00C C00H -2.0(3) . . . . ?
C00E C00A C00G C00F 49.91(18) . . . . ?
C00F O002 C00J C00E -61.54(19) . . . . ?
C00G C00A C00E C00J -49.10(19) . . . . ?
C00H C00I C00K C00D -0.6(3) . . . . ?
C00J O002 C00F C00G 62.81(19) . . . . ?
C00L O004 C00I C00H 175.59(17) . . . . ?
C00L O004 C00I C00K -6.6(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 1.592
_oxdiff_exptl_absorpt_empirical_full_min 0.717
####################################################################### 
# 
# 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_1ver1-20724_abb-761
_database_code_depnum_ccdc_archive 'CCDC 2165922'
loop_
_audit_author_name
_audit_author_address
'Olga Bakulina'
;Saint Petersburg State University
Russia
;
_audit_update_record             
;
2022-04-11 deposited with the CCDC.	2022-10-14 downloaded from the CCDC.
;
_audit_creation_date             2022-04-11
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H18 F N O2'
_chemical_formula_sum            'C16 H18 F N O2'
_chemical_formula_weight         275.31
_chemical_absolute_configuration unk
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      trigonal
_space_group_IT_number           144
_space_group_name_H-M_alt        'P 31'
_space_group_name_Hall           'P 31'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'

_cell_length_a                   9.9484(3)
_cell_length_b                   9.9484(3)
_cell_length_c                   11.8653(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1016.99(7)
_cell_formula_units_Z            3
_cell_measurement_reflns_used    6085
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      1.00000
_cell_measurement_theta_min      0.79156
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.805
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear orangish'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             438
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10563
_diffrn_reflns_point_group_measured_fraction_full 0.952
_diffrn_reflns_point_group_measured_fraction_max 0.908
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.827
_diffrn_reflns_theta_min         5.134
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.871
_reflns_Friedel_fraction_full    0.905
_reflns_Friedel_fraction_max     0.846
_reflns_number_gt                2536
_reflns_number_total             2685
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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         0.184
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 
;
 Flack x determined using 1110 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.17(12)
_refine_ls_extinction_coef       0.0031(9)
_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   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2685
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0324
_refine_ls_restrained_S_all      1.084
_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)+(0.0380P)²+0.1469P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0817
_refine_ls_wR_factor_ref         0.0827
_refine_special_details          ?
_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 O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C12(H12), C13(H13), C15(H15), C16(H16)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_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
F001 F 0.52779(19) 0.76565(19) 0.11468(13) 0.0362(4) Uani 1 1 d . . . . .
O1 O 0.82472(19) 0.57237(19) 0.86010(13) 0.0244(4) Uani 1 1 d . . . . .
H1 H 0.749600 0.512931 0.901331 0.037 Uiso 1 1 calc R U . . .
O2 O 0.79213(19) 0.39200(19) 0.68599(14) 0.0258(4) Uani 1 1 d . . . . .
N1 N 0.7689(2) 0.5914(2) 0.75650(16) 0.0229(4) Uani 1 1 d . . . . .
C1 C 0.7642(3) 0.4994(3) 0.6722(2) 0.0220(5) Uani 1 1 d . . . . .
C2 C 0.7231(3) 0.5292(3) 0.5565(2) 0.0247(5) Uani 1 1 d . . . . .
H2A H 0.811770 0.554727 0.505802 0.030 Uiso 1 1 calc R U . . .
H2B H 0.633737 0.431460 0.528670 0.030 Uiso 1 1 calc R U . . .
C3 C 0.6831(2) 0.6551(3) 0.54599(19) 0.0217(5) Uani 1 1 d . . . . .
C4 C 0.6951(3) 0.7410(3) 0.6353(2) 0.0243(5) Uani 1 1 d . . . . .
H4 H 0.669070 0.819817 0.624158 0.029 Uiso 1 1 calc R U . . .
C5 C 0.7452(3) 0.7270(3) 0.7517(2) 0.0220(5) Uani 1 1 d . . . . .
C6 C 0.6173(3) 0.6992(3) 0.8368(2) 0.0264(5) Uani 1 1 d . . . . .
H6A H 0.518036 0.609425 0.811619 0.032 Uiso 1 1 calc R U . . .
H6B H 0.643614 0.672814 0.910968 0.032 Uiso 1 1 calc R U . . .
C7 C 0.5962(3) 0.8402(3) 0.8503(2) 0.0315(5) Uani 1 1 d . . . . .
H7A H 0.559058 0.860374 0.778283 0.038 Uiso 1 1 calc R U . . .
H7B H 0.516590 0.818257 0.908573 0.038 Uiso 1 1 calc R U . . .
C8 C 0.7476(4) 0.9830(3) 0.8839(3) 0.0367(6) Uani 1 1 d . . . . .
H8A H 0.779373 0.966624 0.959335 0.044 Uiso 1 1 calc R U . . .
H8B H 0.732020 1.073660 0.888362 0.044 Uiso 1 1 calc R U . . .
C9 C 0.8757(3) 1.0163(3) 0.7989(3) 0.0344(6) Uani 1 1 d . . . . .
H9A H 0.974367 1.105559 0.825594 0.041 Uiso 1 1 calc R U . . .
H9B H 0.849442 1.045064 0.725709 0.041 Uiso 1 1 calc R U . . .
C10 C 0.8977(3) 0.8763(3) 0.7823(2) 0.0270(5) Uani 1 1 d . . . . .
H10A H 0.940169 0.858162 0.852512 0.032 Uiso 1 1 calc R U . . .
H10B H 0.974556 0.899596 0.721577 0.032 Uiso 1 1 calc R U . . .
C11 C 0.6363(2) 0.6809(3) 0.4331(2) 0.0212(5) Uani 1 1 d . . . . .
C12 C 0.5993(3) 0.7977(3) 0.4145(2) 0.0256(5) Uani 1 1 d . . . . .
H12 H 0.600393 0.859043 0.476274 0.031 Uiso 1 1 calc R U . . .
C13 C 0.5611(3) 0.8257(3) 0.3087(2) 0.0282(5) Uani 1 1 d . . . . .
H13 H 0.536114 0.905148 0.297124 0.034 Uiso 1 1 calc R U . . .
C14 C 0.5603(3) 0.7351(3) 0.2195(2) 0.0252(5) Uani 1 1 d . . . . .
C15 C 0.5911(3) 0.6169(3) 0.2333(2) 0.0260(5) Uani 1 1 d . . . . .
H15 H 0.586833 0.554491 0.171262 0.031 Uiso 1 1 calc R U . . .
C16 C 0.6288(3) 0.5903(3) 0.3406(2) 0.0232(5) Uani 1 1 d . . . . .
H16 H 0.650079 0.508181 0.351457 0.028 Uiso 1 1 calc R U . . .


_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
F001 C14 1.357(3) . ?
O1 H1 0.8400 . ?
O1 N1 1.400(2) . ?
O2 C1 1.242(3) . ?
N1 C1 1.341(3) . ?
N1 C5 1.482(3) . ?
C1 C2 1.504(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.497(3) . ?
C3 C4 1.329(3) . ?
C3 C11 1.483(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.498(3) . ?
C5 C6 1.537(3) . ?
C5 C10 1.545(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.527(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.519(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.526(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.527(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.401(3) . ?
C11 C16 1.398(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.380(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.386(3) . ?
C14 C15 1.366(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.389(4) . ?
C16 H16 0.9500 . ?

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
N1 O1 H1 109.5 . . ?
O1 N1 C5 114.27(17) . . ?
C1 N1 O1 116.35(17) . . ?
C1 N1 C5 128.7(2) . . ?
O2 C1 N1 122.8(2) . . ?
O2 C1 C2 119.3(2) . . ?
N1 C1 C2 117.84(19) . . ?
C1 C2 H2A 108.1 . . ?
C1 C2 H2B 108.1 . . ?
H2A C2 H2B 107.3 . . ?
C3 C2 C1 116.93(19) . . ?
C3 C2 H2A 108.1 . . ?
C3 C2 H2B 108.1 . . ?
C4 C3 C2 119.7(2) . . ?
C4 C3 C11 122.95(19) . . ?
C11 C3 C2 117.28(19) . . ?
C3 C4 H4 116.5 . . ?
C3 C4 C5 127.0(2) . . ?
C5 C4 H4 116.5 . . ?
N1 C5 C4 109.37(19) . . ?
N1 C5 C6 107.76(18) . . ?
N1 C5 C10 109.82(18) . . ?
C4 C5 C6 109.77(19) . . ?
C4 C5 C10 109.88(19) . . ?
C6 C5 C10 110.21(19) . . ?
C5 C6 H6A 109.1 . . ?
C5 C6 H6B 109.1 . . ?
H6A C6 H6B 107.8 . . ?
C7 C6 C5 112.64(19) . . ?
C7 C6 H6A 109.1 . . ?
C7 C6 H6B 109.1 . . ?
C6 C7 H7A 109.4 . . ?
C6 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
C8 C7 C6 111.0(2) . . ?
C8 C7 H7A 109.4 . . ?
C8 C7 H7B 109.4 . . ?
C7 C8 H8A 109.4 . . ?
C7 C8 H8B 109.4 . . ?
C7 C8 C9 111.1(2) . . ?
H8A C8 H8B 108.0 . . ?
C9 C8 H8A 109.4 . . ?
C9 C8 H8B 109.4 . . ?
C8 C9 H9A 109.2 . . ?
C8 C9 H9B 109.2 . . ?
C8 C9 C10 111.9(2) . . ?
H9A C9 H9B 107.9 . . ?
C10 C9 H9A 109.2 . . ?
C10 C9 H9B 109.2 . . ?
C5 C10 H10A 109.0 . . ?
C5 C10 H10B 109.0 . . ?
C9 C10 C5 112.8(2) . . ?
C9 C10 H10A 109.0 . . ?
C9 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
C12 C11 C3 121.4(2) . . ?
C16 C11 C3 121.2(2) . . ?
C16 C11 C12 117.4(2) . . ?
C11 C12 H12 119.2 . . ?
C13 C12 C11 121.5(2) . . ?
C13 C12 H12 119.2 . . ?
C12 C13 H13 120.8 . . ?
C12 C13 C14 118.4(2) . . ?
C14 C13 H13 120.8 . . ?
F001 C14 C13 118.6(2) . . ?
F001 C14 C15 118.9(2) . . ?
C15 C14 C13 122.5(2) . . ?
C14 C15 H15 120.9 . . ?
C14 C15 C16 118.1(2) . . ?
C16 C15 H15 120.9 . . ?
C11 C16 H16 119.0 . . ?
C15 C16 C11 121.9(2) . . ?
C15 C16 H16 119.0 . . ?

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
F001 C14 C15 C16 178.0(2) . . . . ?
O1 N1 C1 O2 7.1(3) . . . . ?
O1 N1 C1 C2 -172.90(18) . . . . ?
O1 N1 C5 C4 176.54(17) . . . . ?
O1 N1 C5 C6 -64.2(2) . . . . ?
O1 N1 C5 C10 55.9(2) . . . . ?
O2 C1 C2 C3 177.1(2) . . . . ?
N1 C1 C2 C3 -2.9(3) . . . . ?
N1 C5 C6 C7 172.9(2) . . . . ?
N1 C5 C10 C9 -170.2(2) . . . . ?
C1 N1 C5 C4 6.4(3) . . . . ?
C1 N1 C5 C6 125.6(2) . . . . ?
C1 N1 C5 C10 -114.3(2) . . . . ?
C1 C2 C3 C4 4.4(3) . . . . ?
C1 C2 C3 C11 -177.59(19) . . . . ?
C2 C3 C4 C5 -0.4(3) . . . . ?
C2 C3 C11 C12 -178.9(2) . . . . ?
C2 C3 C11 C16 0.5(3) . . . . ?
C3 C4 C5 N1 -4.5(3) . . . . ?
C3 C4 C5 C6 -122.6(2) . . . . ?
C3 C4 C5 C10 116.1(2) . . . . ?
C3 C11 C12 C13 177.6(2) . . . . ?
C3 C11 C16 C15 -177.4(2) . . . . ?
C4 C3 C11 C12 -1.0(3) . . . . ?
C4 C3 C11 C16 178.4(2) . . . . ?
C4 C5 C6 C7 -68.1(3) . . . . ?
C4 C5 C10 C9 69.5(3) . . . . ?
C5 N1 C1 O2 177.1(2) . . . . ?
C5 N1 C1 C2 -2.9(3) . . . . ?
C5 C6 C7 C8 -56.2(3) . . . . ?
C6 C5 C10 C9 -51.6(3) . . . . ?
C6 C7 C8 C9 56.3(3) . . . . ?
C7 C8 C9 C10 -55.2(3) . . . . ?
C8 C9 C10 C5 53.4(3) . . . . ?
C10 C5 C6 C7 53.1(3) . . . . ?
C11 C3 C4 C5 -178.3(2) . . . . ?
C11 C12 C13 C14 -0.1(4) . . . . ?
C12 C11 C16 C15 2.0(3) . . . . ?
C12 C13 C14 F001 -177.9(2) . . . . ?
C12 C13 C14 C15 2.0(4) . . . . ?
C13 C14 C15 C16 -1.8(4) . . . . ?
C14 C15 C16 C11 -0.2(3) . . . . ?
C16 C11 C12 C13 -1.8(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
