# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2019

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

data_a20180355_fr1909
_database_code_depnum_ccdc_archive 'CCDC 1899383'
loop_
_audit_author_name
_audit_author_address
'Leire Sanfelices Mateos'
;Universidad del Pais Vasco
Spain
;
_audit_update_record             
;
2019-02-25 deposited with the CCDC.	2019-07-02 downloaded from the CCDC.
;

_audit_creation_date             2019-01-11T15:08:15-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C22 H18 F3 N O3'
_chemical_formula_sum            'C22 H18 F3 N O3'
_chemical_formula_weight         401.37
_chemical_absolute_configuration ad

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.69927(9)
_cell_length_b                   10.83500(9)
_cell_length_c                   16.94975(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1781.28(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150.00(10)
_cell_measurement_reflns_used    8562
_cell_measurement_theta_min      4.077
_cell_measurement_theta_max      74.122

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_size_max          0.384
_exptl_crystal_size_mid          0.287
_exptl_crystal_size_min          0.155
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_F_000             832
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 7 1 0.1431
4 1 -9 0.1138
3 -6 -5 0.2151
0 -7 1 0.212
-4 0 9 0.1092
2 6 -1 0.1627
-4 1 -9 0.0561
4 0 9 0.0712
1 -6 7 0.1879
-3 -6 -1 0.1878
4 5 4 0.1406


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.028
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Analytical numeric absorption correction using a multifaceted crystal
                        model based on expressions derived by R.C. Clark & J.S.
        (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.757
_exptl_absorpt_correction_T_max  0.88

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_ambient_temperature      150.00(10)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  'Multilayer optics'
_diffrn_source_voltage           50
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_radiation_probe          x-ray
_diffrn_detector_area_resol_mean 5.2012
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      0.089612
_diffrn_orient_matrix_ub_12      -0.0546233
_diffrn_orient_matrix_ub_13      -0.0664491
_diffrn_orient_matrix_ub_21      -0.1277491
_diffrn_orient_matrix_ub_22      -0.0074476
_diffrn_orient_matrix_ub_23      -0.0538384
_diffrn_orient_matrix_ub_31      0.0299496
_diffrn_orient_matrix_ub_32      0.1310046
_diffrn_orient_matrix_ub_33      -0.0307687
_diffrn_measurement_device       'four-circleκ-geometry diffractometer'
_diffrn_measurement_device_type  'Agilent SuperNova'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0164
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_number            9754
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         4.844
_diffrn_reflns_theta_max         68.989
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.992
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.991
_reflns_Friedel_coverage         0.737
_reflns_number_total             3288
_reflns_number_gt                3230
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00 -29.00   0.50    1.00    --  -42.38 -38.00  90.00  172
  2  ω    -94.00  -2.00   0.50    1.00    --  -42.38 125.00  30.00  184
  3  ω     40.00  66.00   0.50    1.00    --  107.93-125.00  90.00   52
  4  ω     34.00  68.00   0.50    1.00    --  107.93 -30.00 -60.00   68
  5  ω     40.00  71.00   0.50    1.00    --  107.93 -45.00-120.00   62
  6  ω     35.00  60.00   0.50    1.00    --  107.93 -45.00 120.00   50
  7  ω     46.00 106.00   0.50    1.00    --  107.93-125.00-180.00  120
  8  ω     82.00 118.00   0.50    1.00    --  107.93-125.00  90.00   72
  9  ω     37.00  63.00   0.50    1.00    --  107.93 -45.00 -30.00   52
 10  ω     40.00  66.00   0.50    1.00    --  107.93 -30.00 -90.00   52
 11  ω     93.00 158.00   0.50    1.00    --  107.93 125.00 -60.00  130
 12  ω     48.00 131.00   0.50    1.00    --  107.93 -61.00   0.00  166
 13  ω     35.00  60.00   0.50    1.00    --  107.93 -45.00 -90.00   50
 14  ω   -119.00 -10.00   0.50    1.00    --  -42.38 -77.00   0.00  218
 15  ω   -116.00 -14.00   0.50    1.00    --  -42.38 -57.00-150.00  204
 16  ω    -30.00  71.00   0.50    1.00    --   42.38 -57.00-150.00  202
 17  ω     82.00 122.00   0.50    1.00    --  107.93  45.00  60.00   80
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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 > 2σ(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.
 shelx_SHELXL_version_number            2018/3

 The Friedel pair coverage of the experiment is almost complete (94%).
 Analysis of the absolute structure using likelihood methods
 (Hooft, Straver & Spek, 2008) was performed using PLATON (Spek, 2009).
 The results indicated that the absolute structure had been correctly
 assigned. The method calculated that the probability that the structure 
 is inverted is smaller than 10-99. The absolute structure parameter y 
 (Hooft, Straver & Spek, 2008) was calculated using PLATON (Spek,
 2010). The resulting value was y=0.01(3), which together with Flack
 parameter value, indicate that the absolute structure has sureley been
 determined correctly.

 Flack, H. D. (1983), Acta Cryst. A39, 876-881
 Flack & G. Bernardinelli, Acta Cryst. 1999, A55, 908-915;  
 H. D. Flack & G. Bernardinelli, J. Appl. Cryst. 2000, 33, 1143-1148.

 R. W. W. Hooft, L. H. Straver & A. L. Spek, J. Appl. Cryst. 2008, 41, 
 96-103
 Dolomanov, O.V. (2009) OLEX2, J. Appl. Cryst., 42, 339-341. 
 Spek, A.L. (2003). J. Appl. Cryst. 36, 7-13.
 Spek, A.L. (2009). Acta Cryst. D65, 148-155.
 A. L. Spek (2010) PLATON, Utrecht, The Netherlands; 
 A. L. Spek, J. Appl. Cryst. 2003, 36, 7-13
 A. L. Thompson & D. J. Watkin, Tetrahedron: Asymmetry 2009, 20, 712--717


;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0383P)²+0.3395P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3288
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0275
_refine_ls_R_factor_gt           0.0271
_refine_ls_wR_factor_ref         0.0691
_refine_ls_wR_factor_gt          0.0688
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 1414 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
 The Friedel pair coverage of the experiment is almost complete 
 (94%). Analysis of the absolute structure using likelihood methods
 (Hooft, Straver & Spek, 2008) was performed using PLATON
 (Spek, 2009). The resulting value was y=0.00(3)
;
_refine_ls_abs_structure_Flack   0.01(3)
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.17
_refine_diff_density_rms         0.037

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.018 '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'

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 0.13800(13) 0.41614(14) 0.93085(6) 0.0388(3) Uani 1 1 d . . . . .
F2 F 0.10954(14) 0.59440(12) 0.87778(8) 0.0420(3) Uani 1 1 d . . . . .
F3 F -0.05591(12) 0.46123(12) 0.87722(7) 0.0330(3) Uani 1 1 d . . . . .
O1 O -0.0714(2) 0.62363(17) 0.75387(11) 0.0523(5) Uani 1 1 d . . . . .
O2 O 0.05413(18) 0.67017(12) 0.65201(8) 0.0329(4) Uani 1 1 d . . . . .
O3 O 0.50411(14) 0.30622(13) 0.77393(7) 0.0272(3) Uani 1 1 d . . . . .
N1 N 0.20702(15) 0.45017(14) 0.66303(8) 0.0170(3) Uani 1 1 d . . . . .
C1 C 0.0170(2) 0.59102(19) 0.70942(11) 0.0278(4) Uani 1 1 d . . . . .
C2 C 0.08372(18) 0.46377(17) 0.71219(10) 0.0192(4) Uani 1 1 d . . . . .
H2 H 0.013996 0.402588 0.693237 0.023 Uiso 1 1 calc R . . . .
C3 C 0.13632(19) 0.41925(16) 0.79393(10) 0.0189(4) Uani 1 1 d . . . . .
H3 H 0.115761 0.328922 0.796818 0.023 Uiso 1 1 calc R . . . .
C4 C 0.29541(18) 0.43115(16) 0.78950(10) 0.0194(4) Uani 1 1 d . . . . .
H4 H 0.332827 0.478517 0.835383 0.023 Uiso 1 1 calc R . . . .
C5 C 0.35765(19) 0.30257(18) 0.78487(12) 0.0229(4) Uani 1 1 d . . . . .
H5A H 0.336412 0.257188 0.834083 0.028 Uiso 1 1 calc R . . . .
H5B H 0.315055 0.257157 0.74043 0.028 Uiso 1 1 calc R . . . .
C6 C 0.5457(2) 0.37725(17) 0.71109(11) 0.0222(4) Uani 1 1 d . . . . .
C7 C 0.6770(2) 0.35366(19) 0.68146(12) 0.0288(4) Uani 1 1 d . . . . .
H7 H 0.732533 0.291207 0.70463 0.035 Uiso 1 1 calc R . . . .
C8 C 0.7263(2) 0.42112(19) 0.61838(12) 0.0289(4) Uani 1 1 d . . . . .
H8 H 0.814562 0.402857 0.597007 0.035 Uiso 1 1 calc R . . . .
C9 C 0.6479(2) 0.51527(19) 0.58610(12) 0.0264(4) Uani 1 1 d . . . . .
H9 H 0.682148 0.562061 0.542935 0.032 Uiso 1 1 calc R . . . .
C10 C 0.51941(19) 0.54041(17) 0.61734(11) 0.0226(4) Uani 1 1 d . . . . .
H10 H 0.467381 0.607135 0.59646 0.027 Uiso 1 1 calc R . . . .
C11 C 0.46382(18) 0.47026(16) 0.67889(10) 0.0194(4) Uani 1 1 d . . . . .
C12 C 0.32236(18) 0.49800(16) 0.71166(10) 0.0180(4) Uani 1 1 d . . . . .
H12 H 0.31165 0.589012 0.719286 0.022 Uiso 1 1 calc R . . . .
C13 C 0.19111(19) 0.50622(16) 0.58561(10) 0.0187(4) Uani 1 1 d . . . . .
H13 H 0.281963 0.500742 0.557939 0.022 Uiso 1 1 calc R . . . .
C14 C 0.08375(18) 0.44688(18) 0.53307(10) 0.0212(4) Uani 1 1 d . . . . .
C15 C 0.0557(2) 0.32270(18) 0.52187(11) 0.0256(4) Uani 1 1 d . . . . .
H15 H 0.103016 0.261526 0.551504 0.031 Uiso 1 1 calc R . . . .
C16 C -0.0431(2) 0.2895(2) 0.46642(12) 0.0332(5) Uani 1 1 d . . . . .
H16 H -0.063562 0.204721 0.45804 0.04 Uiso 1 1 calc R . . . .
C17 C -0.1123(2) 0.3792(2) 0.42309(12) 0.0362(5) Uani 1 1 d . . . . .
H17 H -0.179791 0.355002 0.385515 0.043 Uiso 1 1 calc R . . . .
C18 C -0.0840(2) 0.5033(2) 0.43408(11) 0.0323(5) Uani 1 1 d . . . . .
H18 H -0.131302 0.564372 0.404332 0.039 Uiso 1 1 calc R . . . .
C19 C 0.01510(19) 0.53694(18) 0.48954(10) 0.0248(4) Uani 1 1 d . . . . .
C20 C 0.0680(2) 0.66352(19) 0.51052(12) 0.0292(5) Uani 1 1 d . . . . .
H20A H -0.009099 0.722007 0.51867 0.035 Uiso 1 1 calc R . . . .
H20B H 0.129166 0.695991 0.46861 0.035 Uiso 1 1 calc R . . . .
C21 C 0.1476(2) 0.64291(18) 0.58687(11) 0.0247(4) Uani 1 1 d . . . . .
H21 H 0.230454 0.697728 0.589034 0.03 Uiso 1 1 calc R . . . .
C22 C 0.0796(2) 0.47542(18) 0.86827(11) 0.0264(4) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C22 1.363(2) . ?
F2 C22 1.331(2) . ?
F3 C22 1.332(2) . ?
O1 C1 1.195(3) . ?
O2 C1 1.346(2) . ?
O2 C21 1.459(2) . ?
O3 C5 1.433(2) . ?
O3 C6 1.374(2) . ?
N1 C2 1.465(2) . ?
N1 C12 1.483(2) . ?
N1 C13 1.454(2) . ?
C1 C2 1.524(3) . ?
C2 H2 1 . ?
C2 C3 1.553(2) . ?
C3 H3 1 . ?
C3 C4 1.550(2) . ?
C3 C22 1.504(2) . ?
C4 H4 1 . ?
C4 C5 1.520(3) . ?
C4 C12 1.528(2) . ?
C5 H5A 0.99 . ?
C5 H5B 0.99 . ?
C6 C7 1.393(3) . ?
C6 C11 1.394(3) . ?
C7 H7 0.95 . ?
C7 C8 1.381(3) . ?
C8 H8 0.95 . ?
C8 C9 1.385(3) . ?
C9 H9 0.95 . ?
C9 C10 1.381(3) . ?
C10 H10 0.95 . ?
C10 C11 1.399(2) . ?
C11 C12 1.510(2) . ?
C12 H12 1 . ?
C13 H13 1 . ?
C13 C14 1.514(3) . ?
C13 C21 1.540(3) . ?
C14 C15 1.386(3) . ?
C14 C19 1.393(3) . ?
C15 H15 0.95 . ?
C15 C16 1.390(3) . ?
C16 H16 0.95 . ?
C16 C17 1.391(3) . ?
C17 H17 0.95 . ?
C17 C18 1.386(4) . ?
C18 H18 0.95 . ?
C18 C19 1.393(3) . ?
C19 C20 1.507(3) . ?
C20 H20A 0.99 . ?
C20 H20B 0.99 . ?
C20 C21 1.523(3) . ?
C21 H21 1 . ?

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
C1 O2 C21 125.76(14) . . ?
C6 O3 C5 113.98(14) . . ?
C2 N1 C12 105.34(13) . . ?
C13 N1 C2 112.62(14) . . ?
C13 N1 C12 115.82(14) . . ?
O1 C1 O2 117.35(18) . . ?
O1 C1 C2 123.57(18) . . ?
O2 C1 C2 119.02(16) . . ?
N1 C2 C1 114.85(15) . . ?
N1 C2 H2 107.6 . . ?
N1 C2 C3 102.01(14) . . ?
C1 C2 H2 107.6 . . ?
C1 C2 C3 116.61(15) . . ?
C3 C2 H2 107.6 . . ?
C2 C3 H3 106.4 . . ?
C4 C3 C2 104.94(14) . . ?
C4 C3 H3 106.4 . . ?
C22 C3 C2 120.12(15) . . ?
C22 C3 H3 106.4 . . ?
C22 C3 C4 111.76(15) . . ?
C3 C4 H4 111.5 . . ?
C5 C4 C3 108.75(15) . . ?
C5 C4 H4 111.5 . . ?
C5 C4 C12 108.78(14) . . ?
C12 C4 C3 104.57(14) . . ?
C12 C4 H4 111.5 . . ?
O3 C5 C4 112.02(16) . . ?
O3 C5 H5A 109.2 . . ?
O3 C5 H5B 109.2 . . ?
C4 C5 H5A 109.2 . . ?
C4 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
O3 C6 C7 116.42(17) . . ?
O3 C6 C11 122.76(17) . . ?
C7 C6 C11 120.81(18) . . ?
C6 C7 H7 120 . . ?
C8 C7 C6 119.95(19) . . ?
C8 C7 H7 120 . . ?
C7 C8 H8 119.8 . . ?
C7 C8 C9 120.35(18) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 H9 120.4 . . ?
C10 C9 C8 119.30(18) . . ?
C10 C9 H9 120.4 . . ?
C9 C10 H10 119.1 . . ?
C9 C10 C11 121.77(18) . . ?
C11 C10 H10 119.1 . . ?
C6 C11 C10 117.73(17) . . ?
C6 C11 C12 121.14(16) . . ?
C10 C11 C12 121.08(16) . . ?
N1 C12 C4 100.68(13) . . ?
N1 C12 C11 114.29(13) . . ?
N1 C12 H12 109.8 . . ?
C4 C12 H12 109.8 . . ?
C11 C12 C4 112.25(14) . . ?
C11 C12 H12 109.8 . . ?
N1 C13 H13 107.8 . . ?
N1 C13 C14 115.25(14) . . ?
N1 C13 C21 114.72(14) . . ?
C14 C13 H13 107.8 . . ?
C14 C13 C21 103.18(15) . . ?
C21 C13 H13 107.8 . . ?
C15 C14 C13 128.92(17) . . ?
C15 C14 C19 120.91(18) . . ?
C19 C14 C13 110.06(16) . . ?
C14 C15 H15 120.7 . . ?
C14 C15 C16 118.67(19) . . ?
C16 C15 H15 120.7 . . ?
C15 C16 H16 119.7 . . ?
C15 C16 C17 120.6(2) . . ?
C17 C16 H16 119.7 . . ?
C16 C17 H17 119.6 . . ?
C18 C17 C16 120.8(2) . . ?
C18 C17 H17 119.6 . . ?
C17 C18 H18 120.6 . . ?
C17 C18 C19 118.8(2) . . ?
C19 C18 H18 120.6 . . ?
C14 C19 C18 120.3(2) . . ?
C14 C19 C20 110.47(17) . . ?
C18 C19 C20 129.23(18) . . ?
C19 C20 H20A 111 . . ?
C19 C20 H20B 111 . . ?
C19 C20 C21 103.87(15) . . ?
H20A C20 H20B 109 . . ?
C21 C20 H20A 111 . . ?
C21 C20 H20B 111 . . ?
O2 C21 C13 112.05(15) . . ?
O2 C21 C20 107.37(16) . . ?
O2 C21 H21 110.6 . . ?
C13 C21 H21 110.6 . . ?
C20 C21 C13 105.55(16) . . ?
C20 C21 H21 110.6 . . ?
F1 C22 C3 108.04(15) . . ?
F2 C22 F1 105.77(16) . . ?
F2 C22 F3 108.24(16) . . ?
F2 C22 C3 114.45(16) . . ?
F3 C22 F1 105.47(15) . . ?
F3 C22 C3 114.17(17) . . ?

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 C1 C2 N1 -168.9(2) . . . . ?
O1 C1 C2 C3 -49.6(3) . . . . ?
O2 C1 C2 N1 14.2(3) . . . . ?
O2 C1 C2 C3 133.44(19) . . . . ?
O3 C6 C7 C8 -179.98(18) . . . . ?
O3 C6 C11 C10 177.10(16) . . . . ?
O3 C6 C11 C12 -0.3(3) . . . . ?
N1 C2 C3 C4 20.48(17) . . . . ?
N1 C2 C3 C22 147.24(16) . . . . ?
N1 C13 C14 C15 -41.3(3) . . . . ?
N1 C13 C14 C19 142.61(15) . . . . ?
N1 C13 C21 O2 -35.0(2) . . . . ?
N1 C13 C21 C20 -151.56(16) . . . . ?
C1 O2 C21 C13 5.4(3) . . . . ?
C1 O2 C21 C20 120.9(2) . . . . ?
C1 C2 C3 C4 -105.47(17) . . . . ?
C1 C2 C3 C22 21.3(2) . . . . ?
C2 N1 C12 C4 48.15(16) . . . . ?
C2 N1 C12 C11 168.68(14) . . . . ?
C2 N1 C13 C14 -65.34(19) . . . . ?
C2 N1 C13 C21 54.3(2) . . . . ?
C2 C3 C4 C5 -108.22(16) . . . . ?
C2 C3 C4 C12 7.85(18) . . . . ?
C2 C3 C22 F1 177.18(15) . . . . ?
C2 C3 C22 F2 -65.3(2) . . . . ?
C2 C3 C22 F3 60.2(2) . . . . ?
C3 C4 C5 O3 175.10(14) . . . . ?
C3 C4 C12 N1 -32.78(16) . . . . ?
C3 C4 C12 C11 -154.75(14) . . . . ?
C4 C3 C22 F1 -59.27(19) . . . . ?
C4 C3 C22 F2 58.2(2) . . . . ?
C4 C3 C22 F3 -176.25(16) . . . . ?
C5 O3 C6 C7 -159.65(17) . . . . ?
C5 O3 C6 C11 21.7(2) . . . . ?
C5 C4 C12 N1 83.27(16) . . . . ?
C5 C4 C12 C11 -38.69(19) . . . . ?
C6 O3 C5 C4 -53.1(2) . . . . ?
C6 C7 C8 C9 2.3(3) . . . . ?
C6 C11 C12 N1 -103.48(19) . . . . ?
C6 C11 C12 C4 10.4(2) . . . . ?
C7 C6 C11 C10 -1.5(3) . . . . ?
C7 C6 C11 C12 -178.86(17) . . . . ?
C7 C8 C9 C10 -0.4(3) . . . . ?
C8 C9 C10 C11 -2.5(3) . . . . ?
C9 C10 C11 C6 3.4(3) . . . . ?
C9 C10 C11 C12 -179.21(16) . . . . ?
C10 C11 C12 N1 79.2(2) . . . . ?
C10 C11 C12 C4 -166.95(16) . . . . ?
C11 C6 C7 C8 -1.3(3) . . . . ?
C12 N1 C2 C1 84.10(17) . . . . ?
C12 N1 C2 C3 -42.99(16) . . . . ?
C12 N1 C13 C14 173.32(14) . . . . ?
C12 N1 C13 C21 -67.0(2) . . . . ?
C12 C4 C5 O3 61.8(2) . . . . ?
C13 N1 C2 C1 -43.0(2) . . . . ?
C13 N1 C2 C3 -170.12(14) . . . . ?
C13 N1 C12 C4 173.31(13) . . . . ?
C13 N1 C12 C11 -66.16(19) . . . . ?
C13 C14 C15 C16 -176.05(17) . . . . ?
C13 C14 C19 C18 176.86(16) . . . . ?
C13 C14 C19 C20 -1.3(2) . . . . ?
C14 C13 C21 O2 91.16(18) . . . . ?
C14 C13 C21 C20 -25.39(18) . . . . ?
C14 C15 C16 C17 0.0(3) . . . . ?
C14 C19 C20 C21 -14.9(2) . . . . ?
C15 C14 C19 C18 0.4(3) . . . . ?
C15 C14 C19 C20 -177.81(17) . . . . ?
C15 C16 C17 C18 0.2(3) . . . . ?
C16 C17 C18 C19 -0.1(3) . . . . ?
C17 C18 C19 C14 -0.2(3) . . . . ?
C17 C18 C19 C20 177.6(2) . . . . ?
C18 C19 C20 C21 167.09(19) . . . . ?
C19 C14 C15 C16 -0.3(3) . . . . ?
C19 C20 C21 O2 -94.93(17) . . . . ?
C19 C20 C21 C13 24.76(19) . . . . ?
C21 O2 C1 O1 -172.5(2) . . . . ?
C21 O2 C1 C2 4.6(3) . . . . ?
C21 C13 C14 C15 -167.09(18) . . . . ?
C21 C13 C14 C19 16.78(18) . . . . ?
C22 C3 C4 C5 120.04(16) . . . . ?
C22 C3 C4 C12 -123.89(15) . . . . ?



# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
